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Title: Structural Types and Antimicrobial Application of Borneol, Isoborneol, and 2-Methylisoborneol Monoterpenoids, with a Focus on Borneol from Rosmarinus officinalis

Occurrence and Chemical Composition of Borneol, Isoborneol, and 2-Methylisoborneol in Plant and Microbial Sources

Occurrence and Distribution of Borneol, Isoborneol, and 2-Methylisoborneol in Plant and Microbial Sources

2-Methylisoborneol (2-MIB), a non-canonical monoterpene, is widely distributed across microbial and select plant sources, known for its musty/earthy odor that contributes to off-flavors in water and fish [1][2][3][4][5][6]. It is not toxic but accumulates in biota and trophic levels, driving customer complaints to water utilities globally due to low odor thresholds [4][6].

2-MIB Producers, Genes, and Production Characteristics

Producer Group	Specific Organism/Strain	Key Details	Citations
Cyanobacteria	Pseudanabaena sp. dqh15, Planktothricoides raciborskii CHAB 3331 (Chinese lakes)	Main odorous component; biosynthesis via mtf (SAM-dependent methyltransferase) and mic (terpene cyclase) genes; light-dependent transcription (low light: +30% mtf, +60% mic; high light: -30% mtf, -50% mic; darkness inhibits expression)	[7]
Cyanobacteria	Hapalosiphon strain MRB 220	Capable of 2-MIB production	[8]
Actinobacteria	Pseudonocardiaceae strains (tomb-isolated)	High 2-MIB production (8.60–429.67 ng/mL); linked to springtail attraction for dispersal	[9]
Actinobacteria	Kribbella setae	2-MIB production via KSE_70210-encoded 2-MIB synthase	[10]
Actinobacteria	Streptomyces species	Reservoir MIB producers (fills gap when cyanobacteria are absent); correlates with NH₃ (ρ=0.45, p<0.01) and MIB occurrences (ρ=0.42, p<0.01); maintains density until mid-June, declines with water stratification; resistant to copper via intracellular detention and efflux	[11]
Actinomycetes	Streptomycetes	2-MIB synthesis linked to aerial mycelium development/differentiation	[12]
Myxobacteria	—	2-MIB producers	[3]
Fungi	Fungal isolates	Produce 26–256 ng/L 2-MIB	[13]
Fungi	Penicillium polonicum	2-MIB production on Yeast Extract Sucrose and MEA media	[14]
Plants (Liverworts)	Lophocolea heterophylla, L. bidentata	Contributes to mossy odor alongside geosmin; Conocephalum conicum does not produce 2-MIB	[15]
Other Biological	AS5 microbial strain; Hy sample (19.2% relative abundance, LVI-GC/MS)	Detected in VOC profile; absent from Hy sample essential oil	[1][16]
Plants (Essential Oils)	Curcuma longa	2.92% 2-MIB in essential oil	[17]

2-MIB Concentrations in Various Matrices

Matrix	Concentration Range/Key Value	Context	Citations
Surface Water	Up to 80 ng/L; Pseudanabaena sp. dominant in June	—	[18]
Reservoirs (General)	Up to 196.0 ng/L; 82.4% wet season, 100% dry season samples positive; 46.2% exceed 15 ng/L OTC	—	[19]
Reservoirs (2013 Campaign)	Year maxima 99.1 ng/L (spring outbreak); B:D ratio 0.31; 14.2% exceed OTC	—	[20]
Fermentation Broths	>30 mg/L; maximum 150 mg/L at ~60 h	—	[21]
Lake Taihu (Extracellular)	Mean 146.6 ng/L (August, second highest T&O compound)	Influenced by water temperature and TP; positively correlated with cylindrospermopsins	[22]
Sediments	11.7–49.6 ng/g	Spatial heterogeneity; driven by total nitrogen and sediment organic matter	[23]

2-MIB Environmental and Treatment Dynamics
In northern/southern Chinese reservoirs, summer surface 2-MIB originates mainly from cyanobacteria, while winter/bottom water 2-MIB comes from actinomycetes [24]. Xikeng (XK) reservoir mic gene abundance reaches 5.42 × 10⁴ copies/L in winter, with 2-MIB synthase abundance mirroring mic gene patterns [24]. Actinobacteria (especially Streptomyces sp.) correlate with 2-MIB production in sediments [23].

2-MIB is poorly removed by standard drinking water treatment; cell lysis or filter backwash recirculation can increase potable water concentrations [25]. Filtration achieves 56.5–66.3% removal in some plants [19]. Concentrations as low as 15 ng/L induce fish off-flavors [2], with accumulation in adipose tissues via gill uptake [3][4]. It is synthesized by methylating a monoterpene precursor [12].

Borneol, a related monoterpenoid, is detected in diverse plant essential oils and exhibits significant antimicrobial activity.

Borneol Content in Plant Essential Oils

Plant Source	Borneol Content	Context	Citations
Lavandin-straw stems, lavender-straw flowers	Specific terpene component	—	[26]
Eucalyptus oils	Present	—	[27]
Taxodium distichum leaf oil	Appreciable amounts (not in Nigerian oil)	—	[28]
Micromeria cristata subsp. phrygia (Afyon)	26.9%	Main constituent; (1S)-(-)-borneol (100% enantiomeric purity) across all samples	[29]
Micromeria cristata subsp. phrygia (Isparta)	31.4%	Main constituent; linked to antimicrobial activity	[29][30]
Micromeria cristata subsp. phrygia (Kütahya)	39.3%	Main constituent	[29]
Shoots on PGR-free medium	20.30% (main constituent)	—	[30]
AAEO	58.7 mg/g (GC with standards)	—	[31]
Plant roots (unspecified)	Highest among vegetative organs	Richest in myrtenol	[32]
Diethyl ether fraction (F3)	Present alongside α-terpineol	—	[33]
Oil with n-hexadecanoic acid/thymol/linoleic acid	2.6%	—	[34]
Thymus maroccanus (post-flowering leaves)	Up to 16.3% (0.2–16.3% range)	—	[35]
Thyme oil (carvacrol-dominated)	1.44%	—	[36]
Satureja satureioides	12.4%	Linked to high antimicrobial activity	[37]
Artemisia genus	2.3–8.1%	Active against clinical microorganisms	[38]
Poldokhtar oil	7.1%	Relatively strong antimicrobial activity	[39]
Unspecified oil type III	2.6%	Active against B. cereus/S. aureus	[40]
Ageratina grandifolia	5.2%	—	[41]
Tetradenia macrophyllum	9.1%	—	[41]
Salvia officinalis	5 to 4.5%	Inhibits Gram-positive bacteria/C. albicans	[42]
Etlingera fimbriobracteata rhizome	8.1%	Strong antimicrobial activity against Gram-positive bacteria/fungi	[43]
Tanacetum parthenium leaves	2.9%	Good antimicrobial activity (except K. pneumoniae/P. aeruginosa/A. niger)	[44]
Tanacetum punctatum leaves	2.1%	Good antimicrobial activity (except K. pneumoniae/P. aeruginosa/A. niger)	[44]
Kythrean Sage oil	6.2%	—	[45]
Turkish Artemisia gypsicola (post-flowering, 8 pm)	Up to 22.62%	Strong antimicrobial activity against bacteria/yeast/fungi	[46]
Thymus species	0.7–4.7%	Antimicrobial effect against all tested strains	[47]
Borneol-rich essential oil (BEO)	19.9% ±0.4% / 18.3% ±0.3% (two methods)	Moderate antibacterial activity (S. aureus MIC/MBC: 7.00 mg/ml)	[48]
Teucrium polium (winter EOs)	8.24%	Fungicidal at 20 µl/ml; inhibits bacteria from 10 µl/ml	[49]
Teucrium arduini	5.4%	Antimicrobial against all tested bacteria/fungi	[50]
Unspecified plant oil	10.8%	Active against 10 microorganisms (MIC: 0.56–72.00 mg/mL)	[51]
Rosemary oil	Present	Weak pathogen activity; inhibits B. cinerea/Fusarium sp. at 1000 mg/ml	[52]
Xylopia hypolampra stem bark	7.8%	Weak inhibition against S. aureus/S. pyogenes/E. coli (MIC >500 µg/mL)	[53]
Artemisia aucheri seed	Present	Active against E. coli/S. aureus/L. monocytogenes	[54]

Borneol Antimicrobial Activity
Borneol itself has MIC values of 2.5±0.05 µg/mL (E. coli) to 25.0±0.11 µg/mL (P. aeruginosa) for bacteria and 3.0±0.35 µg/mL (C. albicans) to 4.5±0.65 µg/mL (A. fumigatus) for fungi, with MBC values of 2.5±0.08 µg/mL (E. coli) to 20.0±0.65 µg/mL (S. aureus) [55]. It can be isolated from Achillea millefolium oil via silica gel chromatography, with concentrations increasing under nano Zn oxide treatment [55].

Essential oils containing borneol exhibit varied antimicrobial effects:

M. cristata subsp. phrygia oils (Isparta sample) profoundly inhibit S. typhimurium; A/C oils strongly inhibit C. albicans (vs. ketoconazole) [29].
S. satureioides oil has MICs as low as 0.06% for B. subtilis [37].
A. gypsicola oils show inhibition zones up to 42.3 mm (fungi), 37.3 mm (Gram-positive), 35.7 mm (Gram-negative), with MICs 2.25–144 µg/mL [46]; bioautography links an Rf~0.3 zone (68.9% borneol/31.1% spathulenol) to S. aureus inhibition [56].
BEO damages S. aureus cell walls/membranes (TEM evidence) [48].
E. fimbriobracteata rhizome oil has MICs as low as 19.5 μg/mL (B. subtilis) and 2.4 μg/mL (S. cerevisiae) [43].
T. parthenium/T. punctatum oils inhibit B. subtilis/S. aureus (inhibition zones: 17.9–15.9 mm) [44].

Camphor and borneol are key antimicrobial compounds [57], though Eucalyptus oils (containing borneol) have weak activity [27].

Structural Types and Chemical Composition of Borneol, Isoborneol, and 2-Methylisoborneol Monoterpenoids

Borneol is a widespread constituent of plant essential oils (EOs), with consistent presence across species, cultivars, and geographic regions, often co-occurring with compounds like 1,8-cineole, camphor, and α-pinene. Its concentrations and associated EO components vary significantly by plant source, cultivar, and location, as detailed below:

Borneol Concentrations and Co-Occurring Compounds in Plant Essential Oils

Plant Source	Borneol Concentration	Key Co-Occurring Compounds	Citation(s)
Rosmarinus officinalis (general)	3.6–5.9%	1,8-cineole, camphor; monoterpenes (28.8–50.9%)	[58]
R. officinalis (cultivars: 'Corsican Blue', 'Majorca Pink', etc.)	Main component	α-pinene, camphene, 1,8-cineole, camphor, verbenone, isobornyl acetate, β-caryophyllene	[59]
R. officinalis (specific study 1)	10.39%	Camphor (18.26%), α-pinene (15.51%), 1,8-cineole (11.86%)	[60]
R. officinalis (specific study 2)	13.5%	Eucalyptol (28.7%), camphor (16.7%)	[61]
R. officinalis leaf EO	12.2%	Camphor (31.9%), 1,8-cineole (11.3%), myrcene (10.7%)	[62]
R. officinalis (Algerian provinces: Naâma, Béchar, Adrar)	0.3–21.0%	1,8-cineole (9.7–70.2%), camphor (0.3–31.0%)	[63]
Eucalyptus fimbriobracteata rhizome oil	8.1%	Decanal (34.4%), β-pinene (10%), 1,8-cineole (7%)	[41][43]
Callistemon ornifolia EO	2.9%	Camphor (27.3%), α-fenchol (15.5%), fenchone (4.4%) (oxygenated monoterpenes: 56.3%)	[64]
Cybistax urucurana stem bark EO	14.7%	Bornyl acetate (5.2%), o-cymene (3.2%), terpineol (2.8%), 1,8-cineole (1.8%)	[65]
Aloysia grandifolia oil	5.2%	Bornane carbon skeleton-type fraction (22.0%)	[41]
Tectona macrophyllum oil	9.1%	Bornane carbon skeleton-type fraction (29.6%)	[41]
Micromeria cristata subsp. phrygia (Afyon)	26.9%	— (enantiomerically pure (1S)-(-)-borneol)	[29]
M. cristata subsp. phrygia (Isparta)	31.4%	— (enantiomerically pure (1S)-(-)-borneol)	[29]
M. cristata subsp. phrygia (Kütahya)	39.3%	— (enantiomerically pure (1S)-(-)-borneol)	[29]
Unspecified plant source	2.6%	n-hexadecanoic acid (14.9%), thymol (9.5%), linoleic acid (8.0%)	[34]
Salvia officinalis (Kythrean Sage) EO	6.2%	1,8-cineole (51.0%), camphor (9.3%), α-pinene (5.8%), camphene (6.3%), β-pinene (5.4%)	[45]
Artemisia gypsicola (post-flowering, 8 pm)	22.62%	1,8-cineole, γ-terpinene, cis-4-thujanol, terpinen-4-ol, trans-verbenol, verbenone, menthol, menthone, camphor	[46]
A. gypsicola (pre-flowering, 6 am)	18.22%	Same as above	[46]
A. gypsicola (full flowering, 6 am)	14.98%	Same as above	[46]
Thymus species EOs	0.7–4.7%	Thymol (35.5–47.3%), p-cymene (13.9–23.8%), γ-terpinene (8.9–20.3%), carvacrol (3–5.6%)	[47]
Teucrium arduini EO	5.4%	Sesquiterpene hydrocarbons (68.5%: major class)	[50]
Unspecified plant EO	10.8%	Camphor (14.8%), eucalyptol (12.9%), β-pinene (12.8%), piperitone (10.2%)	[51]
Xylopia hypolampra stem bark EO	7.8%	Verbenone (20.2%), myrtenal, myrtenol (6.80%) (oxygenate terpenes: 73.9%)	[53]
Thymus polium (winter samples)	8.24%	Absent in autumn samples	[49]

Chemically, borneol in R. officinalis is defined as (2S)-1,7,7-trimethylbicyclo[2,2,1]heptan-2-ol [66], and its enantiomeric form varies by species—for example, M. cristata subsp. phrygia produces enantiomerically pure (1S)-(-)-borneol [29]. Borneol contributes to the antimicrobial activity of many EOs: R. officinalis EO showed strong activity against Staphylococcus aureus (inhibition zone >15 mm) [67] and Candida albicans [60], while R. officinalis oil exhibited weak activity against B. cinerea and Fusarium sp. (total inhibition of B. cinerea at 1000 mg/ml, 72% inhibition of Fusarium sp. at 1000 mg/ml) [52].

Borneol derivatives and related compounds also have distinct sources and properties. Bornyl acetate, a borneol derivative, is a major component in Conocephalum conicum chemotype 2 [15], present in Ailanthus mollissima aerial part EO (4.5%) and rhizome oil (5.3% as bornyl formate) [68], and is a major constituent (9.5%) of T. macrophyllum oil [41]. 2-methylisoborneol (MIB), a non-canonical monoterpene linked to microbial sources, was detected at 19.2% in a Hy sample [1]. Produced by microorganisms like Kribbella setae [10] and Streptomyces species (linked to differentiation) [69], MIB has a musty-earthy odor and causes off-flavors in water/fish at low concentrations (sensory threshold 0.1–0.7 ng g⁻¹ in fish muscle) [2]. Structurally, MIB is 1-R-exo-1,2,7,7-tetramethyl-bicyclo[2.2.1]heptan-2-ol [2] and acts as a TRPA1 antagonist [70]; its biosynthesis in Streptomyces griseus is regulated by growth environment [71]. Liverworts Lophocolea heterophylla and L. bidentata emit (−)-2-methylisoborneol and geosmin, causing a mossy odor [15].

The antimicrobial activity of borneol-containing EOs varies by strain and concentration: C. ornifolia EO (high oxygenated monoterpenes including borneol) is more potent against Gram-positive bacteria (MIC 0.40–3.25 mg/mL) [64]; C. urucurana stem bark oil (borneol-rich) has MIC 1.25 mg/mL against S. epidermidis and E. coli [65]; M. cristata subsp. phrygia EO inhibits Gram-negative/positive pathogens [30]; E. fimbriobracteata rhizome oil (8.1% borneol) has MIC as low as 2.4 μg/mL against Saccharomyces cerevisiae [43]; borneol-rich EO (BEO) shows moderate activity against S. aureus (MIC/MBC 7.00 mg ml⁻¹) and sensitivity in E. coli/S. typhimurium (no activity against P. aurantiogriseum/A. niger) [48], with a bactericidal mechanism targeting cell walls/membranes [48]. A. gypsicola volatile oils have strong antimicrobial activity (zones of inhibition: 42.3 mm for fungi, 37.3 mm for Gram-positive, 35.7 mm for Gram-negative; MIC 2.25–144 μg/ml) [46]; T. arduini EO has MIC 6.25–37.50 mg/mL (bacteria) and 7.81–25.00 mg/mL (fungi) [50]; the 10.8% borneol EO is active against 10 microorganisms (MIC 0.56–72.00 mg/mL) [51]; Thymus species EOs (0.7–4.7% borneol) have MIC 6.8–27.6 μg/mL [47]; winter T. polium EO (8.24% borneol) is fungicidal against P. expansum/F. graminearum/F. culmorum/A. ochraceus (20 µl/ml) and inhibits bacteria (10 µl/ml) [49]; A. aucheri seed EO (borneol-containing) acts against E. coli/S. aureus/L. monocytogenes [54]; X. hypolampra stem bark EO (7.8% borneol) shows weak inhibition (MIC >500 µg/mL) against S. aureus/S. pyogenes/E. coli [53]. Camphor and borneol are identified as key antimicrobial compounds [57].

Borneol from Rosmarinus officinalis: Occurrence, Extraction Methods, and Chemical Composition

Borneol is a naturally occurring chiral monoterpenoid present in the essential oils of multiple plant species, including Rosmarinus officinalis (rosemary) [72], existing as (+)-borneol and (-)-borneol isomers [72]. It typically acts as a minor to moderate constituent in rosemary essential oils, alongside dominant compounds such as 1,8-cineole, camphor, and α-pinene [73][74][75][76][77][78][79][80][81][82][83][84][85][86][87][88][89][90][91][92][93][94][95][96][97][98][99][100][101][102][103][104][105][106][107][108][109][110][111][112][113][114][115][116][117][118][119][58][120][121][122][123][124][125][126][127][128][59][129][130][131][132][133][134][135][136][60][61][62][63][66][137][52]. Isoborneol, another monoterpenoid in rosemary essential oils, has also been reported in various concentrations and contexts [138][139][85][87][140][88][141][111].

Variations in borneol content are driven by multiple factors, including bioclimatic parameters (e.g., BIO2, BIO4, BIO7, BIO8) [76], irrigation regimes [78], soil type [80], salinity stress [142], and stress from ivy invasion [86]. Seasonal changes influence borneol levels, with higher amounts in winter and autumn (peaking in February and November) in some regions [109], though concentrations were stable across months in a Serbian study [120]. Geographical origin and variety further contribute to variability, with differences observed between organic cultivars [107], regional populations (e.g., Adriatic/Ionian coasts [76], south Mediterranean Croatia [99], Tunisian populations [112][117], Algerian regions [63]), and specific varieties like R. officinalis Albiflorus vs. var. Gorizia [143].

Rosemary exhibits distinct chemotypes that include borneol or isoborneol. K-means analysis identified a '1,8-cineole and borneol' type [81], while a Sardinian chemotype was characterized as “α-pinene\borneol\bornyl acetate\verbenone” [111]. Tunisian populations included a chemotype with 1,8-cineole/camphor/α-pinene that contained borneol [116]. The Nikita Botanical Gardens (NBG) collection features three chemotypes: Spanish (cineole-camphor, 23.21–25.71% borneol), Tunisian-Moroccan (cineole-borneol, 13.3% borneol), and a dedicated borneol chemotype [136].

Extraction methods for rosemary essential oil (including borneol-containing fractions) vary, with hydrodistillation (HD) using a Clevenger-type apparatus as a common approach [76][144][139][111][113][116][119][120][132]. Other methods include steam distillation (SD) [98][143][107][111][115][130], microwave hydrodiffusion and gravity (MHG) [131], and supercritical fluid extraction (SFE) [84][125]. Post-harvest processing affects borneol retention: freeze-dried samples retain borneol better than frozen ones [145], while spray-drying increases borneol abundance compared to freeze-drying [146]. Glyceline pretreatment enhanced borneol content to 8.3% in distilled oil [114].

Analytical characterization of rosemary essential oils (including borneol and isoborneol) typically uses gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS), with identification based on mass spectral libraries (e.g., Wiley275, NIST/NBS, ADAMS-2007) and retention indices [76][77][144][79][139][90][91][92][98][100][103][104][105][106][107][108][110][111][113][125][130][131][132][133][134][136][67][60][61][62][63][66][137][147][148][52][149]. HS–SPME/GC–MS has also been used for borneol determination [150].

Borneol in rosemary essential oil is associated with biological activities: in silico docking showed it forms a hydrogen bond with acetylcholinesterase residue CYS 447 [92]; SC-CO2 oil with 18.79% borneol exhibited enhanced antimicrobial activity [93]; and it demonstrated antioxidant activity in DPPH (IC50 105.54 ± 3.44 mg) and TBARS (IC50 74.22 ± 2.01 μg) assays [107]. Molecular docking studies have also explored its antibacterial activity against cell wall, protein, and nucleic acid biosynthesis/repair enzymes [151].

Rosmarinus officinalis L. is native to the Mediterranean and cultivated in Europe as a spice and essential oil plant [136]. The NBG-developed cultivar 'Horizont' produces oil similar to Spanish chemotypes, with essential oil yields of 0.7% (May) and 0.8% (October) raw weight, and plantation longevity exceeding 20 years [136]. Yields reach 40–80 cwt ha⁻¹ for 3–5-year-old plants, with 60–65 kg ha⁻¹ of essential oil per season [136].

Reported Borneol Concentrations in Rosemary Essential Oils and Extracts

Source/Context	Borneol Concentration	Citation(s)
General rosemary essential oil sample	4.1% (with p-cymene 26.1%, thymol 37.4% as majors)	[73]
Some rosemary samples	1.4–4.3%	[74]
Adriatic/Ionian coast populations	Up to 21.4%	[76]
S. rosmarinus essential oil	3.66%	[83]
Hydrodistillation (HD)	7.2%	[84]
Supercritical fluid extraction (SFE)	9.2%	[84]
Six rosemary samples	1.4–16.2%	[85]
Ivy-invaded stress sample	41.57%	[86]
One essential oil profile	9.41%	[87]
Different extraction methods	2.28–9.8%	[88]
One analysis	11.7%	[89]
Major component	12%	[90]
SHSD extraction	3.7%	[91]
SHSDACD extraction	5.2%	[91]
SC-CO2 extracts	18.79%	[93]
Steam-distilled (collection period 1)	2.11%	[98]
Steam-distilled (collection period 2)	1.91%	[98]
South Mediterranean Croatia samples	Up to 24%	[99]
Commercially supplied oil	3.81%	[100]
TW irrigation regime	11.160%	[78]
SW irrigation regime	14.132%	[78]
Control (C) soil (L-borneol)	12.88%	[80]
Metal-contaminated (MR) soil (L-borneol)	7.89%	[80]
Glyceline-pretreated distillation	8.3%	[114]
French rosemary (Plavance region)	2.8%	[115]
Plain rosemary plants	7.88%	[103]
Mountainous rosemary plants	8.94%	[103]
Cultivated R. officinalis	2.2%	[104]
One GC-MS analysis	5.23%	[105]
Normal conditions (volatile release)	1.6%	[106]
1000 Gy γ-irradiation (volatile release)	4.8%	[106]
Organic cultivar (flowering aerial parts, EO A)	Maximal in hydroxylated derivatives	[107]
R. officinalis cv CIM-Hariyali (α-terpineol + borneol)	3.73–5.32%	[108]
Tunisian populations	2.63–12.61%	[112]
Dj. Abderahmane population (Tunisia)	25%	[117]
Korbous population (Tunisia)	14.63%	[117]
Sidi Aich mount, Gafsa (Tunisia)	9.37%	[119]
Commercial Slovakian oil	2%	[121]
100% aqueous extract-treated oil	7.20%	[122]
100% acetone extract-treated oil	8.80%	[122]
Supercritical fluid extraction (180 bar/50°C)	4.33%	[125]
Manufacturer-reported composition	2.33%	[127]
Steam-distilled (North Sardinia)	10.2%	[130]
MHG extraction	5.01%	[131]
HD extraction (comparison to MHG)	4.14%	[131]
Hydrodistilled (Algeria)	5.02%	[132]
NBG Spanish chemotype	23.21–25.71%	[136]
NBG Tunisian-Moroccan chemotype	13.3%	[136]
One GC/MS analysis (main monoterpene)	Not specified (main component)	[67]
One essential oil profile	10.39%	[60]
Another essential oil profile	13.5%	[61]
Leaf REO	12.2%	[62]
Algerian provinces (Naâma, Béchar, Adrar)	0.3–21.0%	[63]
RM extract	Main compound	[66]
Some plants (alongside 48% α-pinene)	27%	[137]
General rosemary oil (after eucalyptol)	Not specified (second main compound)	[52]

Reported Isoborneol Concentrations and Contexts in Rosemary

Context	Isoborneol Concentration/Detail	Citation(s)
Metal-contaminated (MR) soil-grown plants	2.20% (only detected here)	[80]
Combined TS2 + MF treatment (S1 salinity stress)	Reduced concentration	[142]
One report	7.16%	[138]
Another report	8.1%	[139]
One essential oil profile	3.13%	[87]
Different extraction methods	2.28–9.8%	[88]
Balady rosemary oil	Component present	[141]
May-harvested samples	More abundant	[85]
Rosemary flowers	Emitted in small amounts	[140]
Capo Caccia, Italy (MD site)	Characteristic component	[111]

Antimicrobial Applications of Borneol, Isoborneol, and 2-Methylisoborneol Monoterpenoids

Borneol occurs as a minor to major component in essential oils (EOs) from diverse plant sources, with its content and co-occurring constituents varying widely across species, extraction methods, and environmental conditions. The (−)-enantiomer predominates in borneol in certain EOs[152], and its production in Lamiaceae species (e.g., Rosmarinus officinalis) increases significantly under drought and salinity stress; salinity specifically elevates borneol content in R. officinalis EO[153]. Isoborneol, a related compound, is present in select EOs (e.g., Hedychium coccineum aerial part EO[154]) and volatile organic compounds (VOCs), with emissions increasing in chrysanthemum headspace after aphid infestation[155]. 2-Methylisoborneol is also identified in some sources, including Streptomyces strain cultures[156].

Borneol and Isoborneol Content in Plant Essential Oils

Plant Source	Borneol Content	Isoborneol Content	Major Co-Occurring Constituents	Citation
Thymus algeriensis	2.53%	—	Camphor (27.7%), α-pinene (20.5%)	[157]
Lavandula dentata	3.2 ± 0.5%	—	1,8-cineole (35.0 ± 1.9%), camphor (32.02 ± 0.5%)	[158]
Unspecified plants	1.4–6.5%	—	Camphor, 1,8-cineole	[74]
Rhododendron mucronulatum	27.74% (major)	—	—	[159]
Salvia officinalis (sage)	7.60%	—	trans-Thujone (37.95%), camphor (13.92%)	[160]
Myrtus communis	27.15% (major)	—	1,8-cineole (21.33%), α-pinene (11.08%)	[161]
Rosmarinus officinalis (source 1)	3.78%	—	Camphor (23.04%), 1,8-cineole (14.01%)	[77]
R. officinalis (source 2)	Not major	—	α-pinene (48.58%), 1,8-cineole (33.4%)	[161]
Zataria majdae	1.1%	—	—	[162]
Satureja veneris	5.8%	—	—	[163]
Tansy (borneol hybrids)	—	—	—	[164]
SlEO-3	Higher than other SlEO samples	—	—	[152]
Lavender EO (LA 2019)	15.7%	—	—	[165]
Lavender EO (LA 2020)	19.4%	—	—	[165]
Hedychium coccineum rhizome (HCCRO)	Unique component	—	—	[154]
Salsola vermiculata	33.77% (major alcoholic monoterpene)	—	—	[166]
Lavender EOs	1–17%	—	—	[167]
Salvia spp. (S. officinalis, S. reuterana)	Main metabolite	—	—	[153]
Thymus vulgaris	2.71%	—	—	[168]
Satureja subspicata	2.11%	—	—	[169]
Unspecified plant (fresh)	2.3%	—	—	[170]
Unspecified plant (dried)	3.1%	—	—	[170]
Unspecified plant	5.0%	—	—	[171]
Lavandula stoechas	2.92%	—	—	[172]
R. officinalis (main component)	—	—	—	[172]
Lavandin EO (cv. 'Alba', 'Sumiens')	High	—	—	[173]
Salvia officinalis (SOEO)	1.18%	—	—	[174]
T. camphoratus	8.5%	—	—	[175]
T. carnosus	29.0%	—	—	[175]
Salvia officinalis	8.15%	—	—	[176]
R. officinalis	9.41%	—	—	[87]
Salvia fruticosa	7.64%	27.17%	—	[177]
Thymus zygis (TZEO)	—	13.62%	—	[178]
H. coccineum aerial part (HCCAO)	—	Unique component	—	[154]
R. officinalis	—	7.16%	—	[138]
Camphor EO	—	8.1%	—	[179]
C. zedoaria EO	—	13.5%	—	[180]
Unspecified plant	—	11.18%	—	[181]
Unspecified plant	—	10.6%	—	[182]
Salvia leriifolia	—	1.5%	—	[183]
C. zedoaria oil	—	7%	—	[184]
Xylopia hypolampra stem bark (XHEO)	7.8%	—	Verbenone (20.2%)	[53]
Thymus satureioides	21.2%	—	Thymol (28.7%)	[149]
R. officinalis	—	—	1,8-cineole (50.3%)	[149]
Artemisia aucheri seed	—	—	Decane, ρ-cymene, 1,8-cineole, linalool, ρ-mentha-8-ol, triene, lavandulol, bornyl acetate, chrysanthenyl acetate, dehydro aromadenderene, caryophyllene oxide	[54]
R. officinalis (source 3)	12% (major)	—	Camphor (22%), α-pinene (17%), 1,8-cineole (16%)	[90]
R. officinalis (Boulemane, Morocco)	<3%	—	—	[92]
R. officinalis (supercritical CO₂ extract)	18.79% (highest)	—	—	[93]
R. officinalis (organic macerate, OM)	3.75% (lowest)	—	—	[93]
R. officinalis (IHBT/RMAc-2 accession)	Significantly higher	—	—	[185]
R. officinalis (steam distillation)	1.5–5.0%	—	—	[186]
R. officinalis (microwave-extracted, SFME)	Part of 28.6% oxygenated monoterpenes	—	—	[187]
R. officinalis (hydrodistilled, HD)	Part of 26.98% oxygenated monoterpenes	—	—	[187]
R. officinalis (Ro-A)	8%	—	1,8-cineole (19%)	[188]
R. officinalis (greenhouse)	—	—	1,8-cineole	[128]
R. officinalis clones (Nonza)	6% of total VOCs	—	—	[129]
R. officinalis clones (Pigette)	14% of total VOCs	—	—	[129]
R. officinalis (source 4)	8.4 mg/mL	—	1,8-cineole (148 mg/mL), camphor (40.0 mg/mL)	[133]
R. officinalis (source 5)	—	—	1,8-cineole, camphor, α-pinene, borneol, camphene	[135]
R. officinalis (source 6)	10.39%	—	Camphor (18.26%), α-pinene (15.51%), 1,8-cineole (11.86%)	[60]
R. officinalis (source 7)	13.5% (major)	—	Eucalyptol (28.7%), camphor (16.7%)	[61]
R. officinalis (source 8)	Main monoterpene	—	Limonene	[67]
Thymus vulgaris (high content)	76.42% (major)	—	—	[151]
Dodonaea viscosa	9.3%	—	—	[189]
Cupressus ornifolia	2.9%	—	—	[64]
Eucalyptus oils	Characteristic monoterpenoid	—	—	[27]
Micromeria cristata subsp. phrygia	26.9–39.3% (main)	—	—	[29]
2-Methylisoborneol	—	2.92%	—	[17]
C. urucurana stem bark	14.7% (main monoterpene)	—	—	[65]
M. cristata subsp. phrygia P. S. Davis	Major component	—	—	[30]
Lavandula angustifolia	8.29% (dominant)	—	—	[190]
Thymus satureioides (source 1)	27% (dominant)	—	—	[137]
EVS oil (thyme-derived)	2.38%	—	—	[191]
T. maroccanus (post-flowering leaves)	16.3%	—	—	[35]
T. maroccanus (range)	0.2–16.3%	—	—	[35]
Thyme EO	1.44%	—	—	[36]
S. satureioides	12.4% (main)	—	—	[37]
Artemisia genus	2.3–8.1%	—	—	[38]
Poldokhtar EO	7.1%	—	—	[39]
Oil type III (unspecified)	2.6%	—	—	[40]
Salvia officinalis (range)	4.5–5%	—	1,8-cineol (55–62%), camphor (8–10%)	[42]
Thymus satureioides (source 2)	34.26% (major)	—	—	[192]
Etlingera fimbriobracteata rhizome	8.1%	—	Decanal (34.4%), β-pinene (10%)	[43]
Tanacetum parthenium leaf	2.9%	—	—	[44]
Tanacetum punctatum leaf	2.1%	—	—	[44]
Achillea gypsicola (post-flowering, 8 pm)	22.62% (highest)	—	—	[46]
Thymus polium (winter)	8.24%	—	—	[49]
Thymus polium (autumn)	0%	—	—	[49]
Teucrium arduini	5.4%	—	—	[50]
Unspecified plant (source 2)	10.8% (main)	—	—	[51]
R. officinalis (source 9)	—	—	Eucalyptol, α-pinene	[52]
Borneol-rich EO (BEO, method 1)	19.9% ± 0.4%	—	—	[48]
Borneol-rich EO (BEO, method 2)	18.3% ± 0.3%	—	—	[48]

EOs containing borneol exhibit varying antimicrobial activities, with efficacy influenced by borneol content, co-occurring components, and target microorganisms. Gram-positive bacteria (e.g., Staphylococcus aureus) are generally more susceptible than Gram-negative bacteria (e.g., Escherichia coli), while yeasts (e.g., Candida albicans) are sensitive and Aspergillus species are less so[74]. Borneol itself inhibits S. aureus more effectively than E. coli and suppresses C. albicans[152], with pure borneol showing MIC values of 2.5–25.0 µg/mL against bacteria and 3.0–4.5 µg/mL against fungi[55]. Synergistic effects between borneol and other EO components often enhance antimicrobial potency; for example, Hedychium coccineum EOs with borneol may act synergistically despite borneol’s predicted low individual activity[154].

Environmental and extraction factors further modulate antimicrobial efficacy. R. officinalis EO with higher borneol content under salinity stress shows improved antibacterial activity[153], and supercritical CO₂-extracted rosemary EO (higher borneol) inhibits C. albicans, E. coli, and S. aureus more effectively than hydrodistilled oil[93]. Borneol is the most potent antimicrobial component in R. officinalis EO, followed by camphor and verbinone[187]. High-borneol EOs (e.g., Micromeria cristata subsp. phrygia, Thymus satureioides) often exhibit strong inhibitory effects against bacteria and fungi, with MIC values as low as 0.015% (v/v) for mycobacterial strains[192]. Borneol’s high water solubility also enhances bacterial cell membrane penetration, contributing to potency[178].

Carbamate derivatives of borneol improve bactericidal activity against E. carotovora[193], and borneol-rich lavandin EOs (cv. 'Abrialis', 'Sumiens') show anti-listerial activity with MIC values as low as 0.6 μL/mL[173]. Additionally, borneol contributes to neurotoxicity against Aphis citricola in tansy EOs[194], and isoborneol exhibits toxicity to stored-product pests like S. zeamais and T. castaneum[184]. Overall, borneol’s antimicrobial activity, combined with its role in EO synergism, underscores its significance in plant-derived antimicrobial agents.

Environmental and Biotic Factors Influencing Production of Target Monoterpenoids

Borneol, isoborneol, and 2-methylisoborneol (2-MIB) are monoterpenoids with variable occurrence across plant and microbial sources, though 2-MIB data is limited in the provided references. Borneol is a common constituent of plant essential oils (EOs), with concentrations and associated components varying by species, population, extraction method, region, and environmental factors. Isoborneol is less widely reported but shows concentration variations in response to season, lighting, and other treatments. 2-MIB is primarily produced by microbial sources, including cyanobacteria, Streptomyces strains, and fungi.

Borneol and Isoborneol Concentrations in Plant Essential Oils

Plant Species	Population/Variety/Stage	Borneol Concentration	Isoborneol Concentration	Key Associated Components/Treatments	Reference(s)
Thymus mastichina	Portugal	Present	—	Camphor, camphene, α-pinene; (–)-enantiomer dominant	[195]
Melissa officinalis	—	Part of 97.7% monoterpenoid fraction	—	1,8-cineole, camphor	[196]
Rosmarinus officinalis	Balkan populations	2.1–21.4%	—	Key component of 1,8-cineole/camphor/borneol chemotype (Dracona)	[76]
Lavandula angustifolia	—	1–17% of oxygenated monoterpenes	—	—	[167]
Lavandula angustifolia	TanL population	6.7%	—	—	[197]
Salvia spp. (S. officinalis, S. reuterana)	—	Among five main metabolites	—	Influenced by genetic differences	[153]
Unspecified species	Leaf distillates	15% of total EO	—	—	[198]
R. officinalis	Extraction method: hydrodistillation (HD)	7.2%	—	—	[84]
R. officinalis	Extraction method: supercritical fluid extraction (SFE)	9.2%	—	—	[84]
R. officinalis	Extraction method: steam distillation	Up to 16%	—	—	[84]
R. officinalis	Tunisian	9.37%	—	—	[84]
R. officinalis	Himalayan-grown	3.35%	—	—	[84]
R. officinalis	Algerian	5.11%	9.68%	—	[84]
R. officinalis	Accession IHBT/RMAc-2 vs. IHBT/RMAc-1	Significantly higher in IHBT/RMAc-2	—	—	[185]
R. officinalis	"Erect rosemary" variety	4.3–9.8%	—	—	[199]
R. officinalis	Stem: vegetative stage	15.8%	—	Among 13 components with stage-dependent differences (p < 0.05/p < 0.001)	[200]
R. officinalis	Stem: flowering stage	4.2%	—	Among 13 components with stage-dependent differences (p < 0.05/p < 0.001)	[200]
R. officinalis	Belgrade, Serbia (cultivated)	4.4–9.5%	—	Main constituent; stable seasonal concentrations	[120]
R. officinalis	Greek	Principal constituent	—	1,8-cineole, α-terpineol	[123]
R. officinalis	Greenhouses	Present	—	1,8-cineole	[128]
Thymus maroccanus	Leaves: post-flowering stage	16.3%	—	—	[35]
Salvia officinalis	—	Major component	—	1,8-cineol (55–62%), camphor (8–10%)	[42]
Unspecified plants	Untreated control	—	1.1 mg/plant	Minor constituent	[201]

2-Methylisoborneol (2-MIB) Producers

Microbial Group	Species/Strain	Source/Medium	Reference(s)
Non-heterocystous cyanobacteria	Pseudanabaena sp. dqh15	—	[202]
Non-heterocystous cyanobacteria	Planktothricoides raciborskii CHAB 3331	Chinese lakes	[7]
Non-heterocystous cyanobacteria	Pseudanabaena sp. strains	Lake Paldang, South Korea	[203]
Non-heterocystous cyanobacteria	Planktothricoides raciborskii NW-1	Nanwan Reservoir	[204]
Streptomyces strains	T-S1 (affiliated with S. zaomyceticus), T-S2 (affiliated with S. hirsutus)	Environmental samples	[205]
Streptomyces sp.	AMU11, AMU14	—	[206]
Streptomyces species	—	Eagle Creek Reservoir	[11]
Penicillium polonicum	—	Yeast Extract Sucrose and MEA media	[14]
Bacteroidota	MAG0848	—	[207]
Myxococcota	MAG0873	—	[207]
Anabaena sp.	FACHB-1384	—	[208]
Planktothrix sp.	FACHB-1374	—	[208]

Environmental and biotic factors strongly influence the production of these monoterpenoids. For R. officinalis, temperature-related bioclimatic parameters (BIO2, BIO4, BIO7, BIO8) are dominant drivers of EO composition, with camphor increasing and 1,8-cineole decreasing in colder conditions [76]. Salinity stress alters R. officinalis EO profiles, strongly increasing borneol content while decreasing α-pinene and 1,8-cineole [153]; similarly, NaCl stress in an unspecified species leads to a slight increase in borneol content at concentrations >50 mM [198]. In R. officinalis, salinity stress (S1, S2) reduces essential oil content, but combined treatments (e.g., TS2 + MF) can mitigate this, though isoborneol concentrations are reduced under such combined treatments [142]. Furthermore, 100 mM NaCl application slightly decreases borneol in R. officinalis EOs [209]. Drought stress increases borneol percentages in R. officinalis [210], and reducing water availability significantly increases borneol relative abundance by 38% in "erect rosemary" EOs [199]. Borneol production rises significantly in 91% of drought and salinity studies on Lamiaceae species [153].

Seasonality affects both borneol (significant variation in R. officinalis [210]; 1.4–16.2% across seasons, highest in January [85]) and isoborneol (highest in May R. officinalis samples [85]; highest in September, lowest in April [211]). In cultivated R. officinalis from Belgrade, borneol shows very stable concentrations during the season [120]. Fertilisation also impacts borneol levels in R. officinalis EOs [210]. Light intensity influences borneol content: reducing light from 100 to 50% decreases borneol by 44% in "erect rosemary" EOs [199]. For 2-MIB-producing cyanobacteria, low light increases transcription of 2-MIB biosynthesis genes (mtf and mic) by 30% and 60%, respectively, while high light decreases their transcription by 30% and 50% [7]; high light intensity (60 μmol photons s−1 m−2) is more conducive to 2-MIB production in P. raciborskii [204].

Biotic stress, such as fungal infection, increases borneol content in R. officinalis EOs [212], and stress from ivy (Hedera helix) invasion leads to higher borneol (41.57%) in R. officinalis samples [86]. Borneol is positively correlated with sunshine hours per day (r = 0.71) in R. officinalis [86]. Storage conditions influence borneol content in M. officinalis EOs: quantities increase with storage time at room temperature, while minimal alterations occur at 4 °C and −20 °C [196]; in H. webbii Z3 EO, isoborneol content increases during 4 years of storage [213]. Additionally, oil exposure to sunlight produces borneol (up to 12.1% yield), and UV light generates isoborneol (5.1% yield) [214]. Notably, borneol shows no significant differences with growth environment changes in one study [215], contrasting with other findings on stress and climatic effects.

Isoborneol also responds to treatments: it increases substantially in I-W Perseid plants [216], and its content is moderately significant (p ≤ 0.01) in response to Gallic acid rates [201]. For 2-MIB production, temperature plays a key role: in Pseudanabaena sp. strains PD34 and PD35, maximum 2-MIB concentrations occur at 25 °C [203]; in P. raciborskii, higher temperatures (25–33 °C) are favorable for synthesis and secretion [204]; in Streptomyces strains T-S1 and T-S2, optimal production occurs at 25 °C (least at 30°C and 35°C) [205]; in Nanwan Reservoir, 2-MIB is highest in summer [204], while another study reports maximum 2-MIB in November at 10.3–13.7 °C [217]. In Pseudanabaena sp. dqh15, 2-MIB production is tested at 10 °C, 25 °C, and 35 °C [202], and Anabaena sp. FACHB-1384 is sensitive to low temperatures (<20°C) [208].

The use of biostimulants has a significant (p ≤ 0.01) effect on borneol content in R. officinalis EOs, with the highest borneol content in Aminolforte at 0.75 L ha-1 (7.97%) and the lowest at 1.5 L ha-1 (5.5%) [218]. In 2-MIB-producing cyanobacteria, mtf and mic gene expression is inhibited in darkness at 25°C [7], and 2-MIB yields per cell and per mic DNA copy increase with culture temperature [203]. In Nanwan Reservoir, 2-MIB content correlates positively with total phosphorus (TP), water temperature (WT), pH, and chlorophyll a (Chl a) but negatively with total nitrogen (TN), dissolved oxygen (DO), Secchi depth (SD), dissolved inorganic nitrogen (DDN), and nitrate (NO3−) [204]. In the Nakdong River, 2-MIB is highest in June, associated with dominant Pseudanabaena sp. [18].

Nutrient availability influences 2-MIB production: in an Alabama drinking water reservoir, MIB was higher with both nutrients added [219]; in Lake Taihu, 2-MIB was influenced by water temperature and TP [22]; in two Chinese reservoirs, 2-MIB synthase abundance was inhibited by TN, with temperature affecting Actinomycetes in Jinpen Reservoir and DO in Xikeng Reservoir [24]; in sediment, TN and organic matter drive 2-MIB spatial heterogeneity [23]. In P. polonicum, 2-MIB was higher at 93% RH [14]. In Eagle Creek Reservoir, Streptomyces species correlated positively with NH3 (ρ = 0.45, p < 0.01) and MIB occurrences (ρ = 0.42, p < 0.01) [11]. In Planktothrix sp. FACHB-1374, only 2-MIB productivity was reduced under P-limitation [208].

Antimicrobial and Bioactive Properties of Borneol and Isoborneol Monoterpenoids

Occurrence and Antimicrobial Activity Profiles of Borneol, Isoborneol, and 2-Methylisoborneol in Plant Essential Oils

Borneol is a widespread oxygenated monoterpenoid in plant essential oils (EOs), occurring in variable concentrations across species. Isoborneol, a related monoterpenoid, is also present in many EOs, and 2-methylisoborneol (2-MIB) is identified in select sources. The antimicrobial activity of EOs containing these compounds varies by composition, target microorganism, and borneol/isoborneol concentration, with synergistic effects often enhancing efficacy.

Borneol Concentrations in Plant Essential Oils

Plant Source	Borneol Concentration	Reference
Thymus algeriensis	2.53%	[157]
Lavandula dentata	3.2 ± 0.5%	[158]
Unspecified plant (most samples)	1.4–4.3%	[74]
Unspecified plant (one sample)	6.5%	[74]
Thymus sipyleus subsp. sipyleus var. davisianus	3.83%	[220]
Artemisia herba-alba	2.7%	[221]
Thuja canadensis (cone)	0.7%	[222]
CZEO (unspecified source)	2.23%	[223]
Satureja veneris	5.8%	[163]
Thymus riatarum	41.67% (dominant)	[224]
Unspecified plant (mature fruit)	2.64 ± 0.30%	[225]
Salvia officinalis (sage)	7.60%	[160]
Rosmarinus officinalis (Morocco)	10% (main component)	[226]
Thymus algeriensis (naturally grown)	8.1%	[227]
Thymus algeriensis (cultivated)	3.5%	[227]
Sage oil (Sag)	7.2%	[228]
Yarrow oil (Yar)	4.1%	[228]
Rosmarinus officinalis (leaf)	3.78%	[77]
Myrtle (M. communis L.)	27.15%	[161]
Lavender EO (LA 2019)	15.67%	[165]
Lavender EO (LA 2020)	19.35%	[165]
S. vermiculata	33.77%	[166]
Thymus vulgaris	2.71%	[168]
S. subspicata	2.11%	[169]
Daucus graveolens	18.7%	[229]
Origanum vulgare L.	6.52%	[230]
Lavandula virgata	3.1%	[231]
Lavandula stoechas	2.92%	[172]
Romanian lavandin	7.11%	[173]
Rosmarinus officinalis	8.72%	[232]
White thyme oil	32%	[233]
Artemisia herba-alba	6.1%	[234]
Salvia officinalis	8.15%	[176]
Thymus camphoratus	8.5%	[175]
Thymus carnosus	29.0% (rich)	[175]
C. morifolium	7.95%	[235]
S. officinalis	3.2%	[236]
T. satureioides (inoculated-AMP)	18.7%	[237]
Rosmarinus officinalis	11.7%	[89]
Rosmarinus officinalis	12%	[90]
R. officinalis (Argentina, WP and NP phenotypes)	0.4–15.4%	[238]
R. officinalis (Moroccan wild habitat)	15.46%	[239]
R. officinalis (Ro-A)	8%	[188]
R. officinalis (one sample)	2.7–2.8%	[240]
R. officinalis (one sample)	10.39%	[60]
R. officinalis (one sample)	13.5%	[61]
R. officinalis (domestication/extraction variation)	0.53–1.67%	[241]
Satureja cuneifolia (Sc-A)	~24%	[188]
Satureja cuneifolia (Sc-B)	19%	[188]
Satureja cuneifolia (Sc-C)	12.9%	[188]
Thymus vulgaris	76.42%	[151]
D. viscosa	9.3%	[189]
P. barbatus	20.7%	[242]
C. ornifolia	2.9%	[64]
Lavandula angustifolia	1.9%	[243]
Micromeria cristata subsp. phrygia (Afyon)	26.9% (main constituent)	[29]
Micromeria cristata subsp. phrygia (Isparta)	31.4% (main constituent)	[29]
Micromeria cristata subsp. phrygia (Kütahya)	39.3% (main constituent)	[29]
C. urucurana (stem barks)	14.7% (main monoterpene)	[65]
Unspecified plant	25.28% (major constituent)	[30]
Lavandula angustifolia	8.29% (dominant component)	[190]
Thymus maroccanus (post-flowering leaves)	16.3%	[35]
S. satureioides	12.4% (main constituent)	[37]
Artemisia spp. (A. annua, A. vulgares, A. diffusa)	2.3–8.1%	[38]
Unspecified plant	21.83% (major component)	[244]
Poldokhtar	7.1%	[39]
Unspecified plant (oil type III)	2.6%	[40]
S. officinalis	5 to 4.5%	[42]
T. satureioides	34.26%	[192]
E. fimbriobracteata (rhizome)	8.1%	[43]
T. parthenium	2.9%	[44]
T. punctatum	2.1%	[44]
A. gypsicola (post-flowering stage-8 pm)	22.62%	[46]
Thymus algeriensis	0.7–4.7%	[47]
Thymus polium (winter)	8.24%	[49]
Teucrium arduini	5.4%	[50]
Xylopia hypolampra (stem bark)	7.8%	[53]
Thymus satureioides	21.2%	[149]

Isoborneol Concentrations in Plant Essential Oils

Plant Source	Isoborneol Concentration	Reference
ETJA lavender oil	Not specified	[245]
Rosmarinus officinalis	7.16%	[138]
C. indicum	7.64%	[235]
T. zygis EO (TZEO)	13.62%	[178]
Camphor EO	8.1%	[179]
C. zedoaria	13.5%	[180]
Rosmarinus officinalis	3.13%	[87]
R. officinalis (fresh leaves, extraction-dependent)	2.28–9.8%	[88]
C. caesia (rhizome)	5.05%	[246]
C. zedoaria	7%	[184]
Unspecified plant	2.57%	[247]
Unspecified EO	8.1%	[248]
C. caesia (rhizome)	4.51%	[249]
R. officinalis	5.43%	[250]
A. santolina	13.12%	[251]
L. dentata (inoculated-AMP)	8.8%	[237]
Unspecified EO	2.334%	[252]
S. africana (Morocco)	6.1%	[253]
S. africana (Tunisia)	26.6%	[253]

2-Methylisoborneol (2-MIB) Occurrence

2-MIB is identified in Curcuma longa EO (2.92% [17]), as a volatile from bacterium WAC-288 [254], and as an abundant VOC in Streptomyces cultures [156].

EOs containing borneol exhibit diverse antimicrobial effects. For example, T. riatarum EO (41.67% borneol) has a broad antibacterial spectrum (MIC 3.75–7.5 mL/L [224]), while rosemary EO (10% borneol) targets Gram-positive bacteria and fungi (MIC 0.2–30 mg/mL [226]). CZEO (2.23% borneol) inhibits MRSA growth (53.83% at 0.4 g/L [223]), and myrtle EO (27.15% borneol) has MIC 0.5% (v/v) against S. typhimurium [161]. Lavender EO LA 2020 (19.35% borneol) shows greater bactericidal/fungicidal activity than LA 2019 (15.67% borneol [165]).

Isoborneol contributes to antimicrobial activity: it inhibits E. coli, S. aureus, and Mucor sp. [255], has virucidal effects on HSV-1 [235][256][257], and is a key compound in PJH oil (VIP>1 [258]). AMF-inoculated L. dentata EO (with isoborneol) shows improved antifungal activity against plant pathogens [237].

Rosemary EO antimicrobial activity is influenced by borneol content, extraction method, and origin: SFME-extracted R. officinalis EO has higher borneol and better activity [187]; R. officinalis EO from Serbia (RF) shows a 40.00 mm inhibition zone [259]; and Tunisian R. officinalis EO inhibits plant pathogen spore germination (85.99–100% at 6 mM [260]). Synergism between EO components (e.g., borneol with camphor [187]) often enhances efficacy.

Other notable effects include T. algeriensis EO (2.53% borneol) inhibiting wood-decay fungi [157], sage EO (7.60% borneol) targeting B. cereus and E. coli [160], and white thyme oil (32% borneol) eradicating biofilms [233]. Borneol’s high water solubility enhances bacterial membrane penetration [178], while isoborneol exhibits insect toxicity (LC50 36–95 mL/L for S. zeamais and T. castaneum [184]).

Chemical Structure-Dependent Antimicrobial Mechanisms of Borneol, Isoborneol, and 2-Methylisoborneol

Borneol is a bicyclic monoterpenoid alcohol whose structure enables easy oxidation to camphor, a related bicyclic monoterpenoid [261][262]. It is a key component of essential oils from sources like Rosmarinus officinalis, while its structural isomer isoborneol—distinguished by the steric orientation of its hydroxyl group—is also identified in essential oils, including those from rosemary [250][263]. Both compounds exhibit bioactivity, though their effects and mechanisms differ due to structural and stereochemical differences.

Content and Antimicrobial Activity of Borneol and Isoborneol

Compound	Source	Content	Antimicrobial Activity	Citations
Borneol	Rosmarinus officinalis essential oil	6.73–10.36% (relative); 45.80–92.45 mg/g (absolute)	Broad activity: antibacterial (Gram-positive Staphylococcus aureus; Gram-negative Escherichia coli) and antifungal (Candida albicans, Aspergillus niger)	[261][262]
Isoborneol	Rosmarinus officinalis essential oil	5.43% (relative)	Stereospecific antisporulating activity against Aspergillus flavus (minimum sporulation quenching concentration: 80 μg/mL; no effect on bacterial/fungal growth in all assays; no antisporulating activity observed for borneol)	[250][263][264]

The antimicrobial mechanisms of these monoterpenoids are tied to their structural features and microbial cell interactions. Borneol enhances membrane porosity in Listeria monocytogenes and Pseudomonas aeruginosa, supporting its bacteriostatic and antibiofilm activities [265]. Essential oils containing borneol disrupt the cell wall and cytoplasmic membrane of bacteria like S. aureus, causing blurred cell outlines, broken cell walls, and lysis [48]. For rosemary essential oil (which includes isoborneol), the antifungal mechanism involves ergosterol complexation—an effect evidenced by increased minimum inhibitory concentration (MIC) values in ergosterol’s presence [250]. The hydroxyl functional group is critical for activity, as alcohols are generally more active than corresponding aldehydes or ketones [261][195]. Hydrophobicity/lipophobicity also influences potency, as these molecules integrate into lipid bilayers, increasing membrane permeability and causing leakage of vital cell contents [261].

Docking studies provide molecular insights: borneol interacts with ILE78 (hydrophobic) and GLU50, ARG76 (hydrogen bonds) in target proteins, while isoborneol forms hydrogen bonds with ILE416, VAL463, GLY417 and hydrophobic interactions with ALA366 [263]. These structural interactions, combined with functional groups (e.g., hydroxyl) and steric orientation, underpin the distinct antimicrobial activities of borneol and isoborneol.

Extraction Methods and Environmental Stress Effects on Borneol Content in Rosmarinus officinalis

Borneol, a key oxygenated monoterpene in Rosmarinus officinalis essential oil (EO), exhibits wide variation in content driven by extraction methods, environmental factors, and genetic/harvest variables. Isoborneol, a related monoterpene, is also present in varying concentrations. Extraction techniques significantly influence borneol levels, with supercritical CO₂ (SC-CO₂) extraction yielding the highest reported values, while modified simultaneous hydrodistillation (MSHD) outperforms conventional hydrodistillation (HD). Additional extraction methods—including supercritical fluid extraction (SFE), supercritical fluid microwave extraction (SFME), hexane:acetone solvent extraction, and stomached maceration—produce distinct borneol profiles, with stomaching enhancing verbenone and camphor levels by 20–30 fold relative to chopped herb extracts [266]. Beyond extraction, wild R. officinalis (WR) EO has lower borneol content (0.53–1.67%) than some cultivated accessions, with microwave-assisted extraction (ME) differing from Clevenger hydrodistillation (CH) [241]. Environmental stressors like UV-B (transient increases) and salinity (strong increases from 4.39% to 16.8%) alter borneol levels, while water deficit affects production in Salvia spp. [78, 586, 173]. Borneol content also varies by accession (higher in IHBT/RMAc-2 vs. IHBT/RMAc-1), harvest stage (higher in flowering aerial parts), and clone (6% in Nonza vs. 14% in Pigette VOCs) [596, 651, 716]. Headspace analysis shows trace borneol/camphor in intact herbs, with chopping increasing detection but stomaching boosting verbenone/camphor ~20 fold [266].

Borneol and Isoborneol Concentrations in Rosmarinus officinalis Extracts by Method and Context

Component	Extraction Method/Context	Concentration	Citation
Borneol	Hydrodistillation (HD)	4.21%	[267]
Borneol	Supercritical CO₂ (SC-CO₂)	18.79%	[93]
Borneol	HD	7.47%	[268]
Borneol	Aerial part EO (unspecified method)	9.41%	[87]
Borneol	Unspecified method	11.7%	[89]
Borneol	Unspecified method	12%	[90]
Borneol	Supercritical fluid extraction (SFE)	20–24 g/kg	[269]
Borneol	Modified simultaneous hydrodistillation (MSHD)	6.09%	[267]
Borneol	Wild R. officinalis (WR) EO	0.53–1.67%	[241]
Borneol	Control plants (salinity study)	4.39%	[270]
Borneol	Salt-stressed plants	16.8%	[270]
Isoborneol	Across extraction methods	2.28–9.8%	[88]
Isoborneol	Aerial part EO (unspecified method)	3.13%	[87]
Isoborneol	Unspecified profile	5.43%	[250]

Borneol contributes to the functional properties of R. officinalis EO, including antimicrobial, antioxidant, and therapeutic effects. SC-CO₂-extracted EO (high borneol) shows enhanced antimicrobial activity: ~1.5-fold greater inhibition of Candida albicans and C. tropicalis, ~1.5–2.0-fold greater inhibition of Escherichia coli and Salmonella typhimurium, and ~2.5-fold greater inhibition of Bacillus subtilis and Staphylococcus aureus compared to HD oil [93]. Salinity-stressed extracts, with elevated borneol, exhibit stronger inhibition of Gram-positive bacteria (Micrococcus luteus, S. aureus, Clostridium perfringens) and C. albicans [270]. SFME-extracted EO outperforms HD oil against E. coli, S. aureus, and K. pneumoniae, with borneol identified as the most potent antimicrobial component followed by camphor and verbenone [187]. R. officinalis EO inhibits Gram-positive (S. aureus MTCC 96, B. subtilis) and some Gram-negative (S. typhi MTCC 733) bacteria, with MIC values of 0.23–7.5 mg ml⁻¹ [596, 618]. Isoborneol has virucidal activity against HSV-1 by inhibiting viral protein glycosylation [271].

In anti-listerial assays against Listeria innocua, borneol displayed lower activity (1–2 mm zone of inhibition, MIC 5 mg/ml) compared to verbenone (MIC 1 mg/ml), camphor (MIC 1 mg/ml), bornyl acetate, and caryophyllene, with effectiveness ordered: verbenone > camphor > bornyl acetate > caryophyllene > borneol [266]. Borneol also contributes to R. officinalis EO’s antioxidant activity (identified via random forest regression) and has individual antioxidant activity with IC₅₀ values of 105.54 ± 3.44 mg (DPPH) and 74.22 ± 2.01 μg (TBARS) [590, 651]. Traditionally used in Chinese medicine for analgesic, antipyretic, and resuscitative effects, borneol completed phase III trials for stable angina (2017) and acute ischemic stroke (2022) [153]. Additionally, steam-distilled R. officinalis EO (yield ~1%, major components: piperitone 23.65%, α-pinene 14.94%, limonene 14.89%, 1,8-cineole 7.43%) suppressed Aspergillus parasiticus growth and aflatoxin biosynthesis, with a fungistatic MIC of 1750 ppm and aflatoxin inhibition at 450 ppm [148].

Structural Analogues and Derivatives of Borneol and Isoborneol with Antimicrobial and Pest-Repellent Properties

Borneol and isoborneol are bicyclic monoterpenoids with well-documented antimicrobial, pest-repellent, and anti-inflammatory properties, as well as bioactive derivatives. Isoborneol is present in Rosmarinus officinalis essential oil at 3.98% [272], while borneol is a major volatile organic compound (VOC) in R. officinalis—detected in rosemary greenhouses [128] and accounting for 6% to 14% of total VOCs across different R. officinalis clones [129]. Both natural borneol (NB, 98.96% borneol) and synthetic borneol (SB, 61.39% borneol and 35.77% isoborneol) exhibit anti-inflammatory activity, reducing LPS-induced NO, TNF-α, and IL-6 levels in RAW 264.7 macrophages and attenuating endotoxic fever in rats [273].

Bioactivity of Borneol, Isoborneol, and Their Derivatives

Compound/Derivative	Target Organism/Pest	Activity Measure	Value	Citation(s)
Borneol (Fluka, 80% purity)	Ixodes ricinus nymphs	Repellency (field trial)	51% (outperformed MyggA®: 39%)	[274]
(+)-Borneol enantiomer	Ticks	Repellency (vs. control)	Significant (not different from (−)-borneol)	[274]
(−)-Borneol enantiomer	Ticks	Repellency (vs. control)	Significant (not different from (+)-borneol)	[274]
Isoborneol (1,000 ppm)	Reticulitermes santonensis, R. flavipes	Tunneling prevention	Effective in loamy sand/sand; reduced in sandy clay (evaporation)	[275]
Isoborneol	Odontotermes assamensis	Antitermitic mortality	90% at 2.5 mg/g	[272]
Borneol	Germplasm populations, R. officinalis varieties	Association with repellency	Negative correlation; positive with 'No_choice' repellency components	[276]
(−)-Borneol	Aedes aegypti larvae	Larvicidal LC₅₀	254.6 ppm	[277]
Isoborneol	Aedes aegypti larvae	Larvicidal LC₅₀	598 ppm	[278]
Borneol	Aedes aegypti larvae	Larvicidal LC₅₀	610 ppm	[278]
(−)-Bornyl chloroacetate	Aedes aegypti larvae	Larvicidal LC₅₀ (highest ester activity)	20.3 ppm	[277]
Isoborneol	Sitophilus zeamais (stored-product pest)	Toxicity LC₅₀ (air)	73–95 mL/L	[184]
Isoborneol	Tribolium castaneum (stored-product pest)	Toxicity LC₅₀ (air)	36–45 mL/L	[184]
Borneol	Sitophilus oryzae (stored-product pest)	Mortality (24 h)	100% at ≥10 ml/720 ml volume	[279]
Borneol	Rhyzopertha dominica (stored-product pest)	Mortality (24 h)	95% at ≥1 ml/720 ml volume	[279]
Borneol	Rhyzopertha dominica (stored-product pest)	Mortality (7 days)	95% at 0.1 ml/720 ml volume	[279]
Borneol-containing essential oil (BEO)	Mites	Miticidal mortality (24 h)	~80% at 0.50–0.70 mg ml⁻¹	[48]
BEO	Mites	Miticidal mortality (48 h)	>95% at 0.50–0.70 mg ml⁻¹	[48]
BEO	Dust mites	Repellency grade	B-grade (0.35 mg ml⁻¹); A-grade (0.50 mg ml⁻¹)	[48]
Borneol carbamate derivatives	Erwinia carotovora	Bactericidal activity	Enhanced vs. parent borneol	[193]
(+)- and (+)-isoborneol derivatives	Certain viruses	Inhibitory IC₅₀	Lower (greater inhibition) than (+)-borneol derivatives (more toxic)	[280]
(−)-Borneol esters	Aedes aegypti larvae	Correlation between Log P and larvicidal activity	Quadratic (r² = 0.70, includes chloroacetate)	[277]
BEO	Staphylococcus aureus	Antibacterial MIC/MBC	7.00 mg ml⁻¹	[48]
BEO	Escherichia coli, Salmonella typhimurium	Antibacterial sensitivity	More sensitive than S. aureus/B. subtilis	[48]

Derivatization of borneol and isoborneol has yielded compounds with improved biological activity. For example, borneol carbamate derivatives enhanced bactericidal activity against Erwinia carotovora compared to the parent compound [193], while (+)- and (+)-isoborneol derivatives showed greater viral inhibition (lower IC₅₀ values) than (+)-borneol derivatives, albeit with higher toxicity [280]. A quadratic correlation (r² = 0.70) between Log P and larvicidal activity was observed for (−)-borneol esters, including the highly potent (−)-bornyl chloroacetate [277]. Borneol-containing BEO exhibited moderate antibacterial activity against Staphylococcus aureus (MIC and MBC = 7.00 mg ml⁻¹) [48], with greater sensitivity in Escherichia coli and Salmonella typhimurium relative to S. aureus and Bacillus subtilis [48]. Transmission electron microscopy revealed the bactericidal mechanism of BEO involves disruption of the cell wall and cytoplasmic membrane, as evidenced by blurred cell outlines, broken cell walls, and lysis in S. aureus treated with 1× and 2× MIC of BEO [48].

Technical Limitations in Borneol and Isoborneol Application: Weak Activity and Inconsistent Efficacy Across Microbial Strains

Borneol is a constituent of essential oils from various plant sources, including Xylopia hypolampra stem bark (7.8% of the total oil) [53] and Rosmarinus officinalis (rosemary) oil, where it is a secondary component following eucalyptol [52]. The antimicrobial activity of borneol-containing essential oils is often weak, with inconsistent efficacy across microbial strains and application conditions, as summarized below:

Antimicrobial Activity and Efficacy of Borneol-Containing Essential Oils

Plant Source	Borneol Content	Target Microorganism(s)	Key Outcome	Citation
Xylopia hypolampra	7.8%	Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli	MIC values >500 µg/mL	[53]
Rosmarinus officinalis	Secondary component	Fusarium sp.	72% inhibition of radial growth at 1000 mg/ml	[52]
Unspecified plant source	5.8%	All tested microorganisms	MIC values 625–1250 μg/mL; activity up to 20,000-fold smaller than positive controls for Bacillus subtilis	[163]
Rosmarinus officinalis	Secondary component	Escherichia coli	Maximum inactivation of 1.23 log CFU/g alone; no synergistic effect with SC-CO₂ (0.1%, 0.5%, 1% v/w)	[281]

Further technical limitations are evident in the application of rosemary essential oil (with borneol) for E. coli inactivation: no synergistic effect was observed when combined with supercritical carbon dioxide (SC-CO₂) across all tested concentrations (0.1%, 0.5%, 1% v/w), unlike coriander essential oil [281]. These findings highlight key technical limitations of borneol-containing preparations, including weak inherent antimicrobial activity and inconsistent efficacy across microbial strains and application conditions.

Biosynthesis and Degradation Pathways of Borneol, Isoborneol, and 2-Methylisoborneol

Structural Characterization and Synthetic Pathways of Borneol, Isoborneol, and 2-Methylisoborneol Monoterpenoids

Synthetic pathways for borneol and isoborneol primarily use camphene as a key precursor, with catalytic and reaction conditions dictating product selectivity. Key outcomes of major camphene-based routes are summarized below:

Key Outcomes of Camphene-Based Borneol/Isoborneol Synthetic Routes

Reaction Type	Catalyst/Solvent System	Key Conditions	Main Product(s) & Yields/Selectivity	Citations
Oxidation	Al₄/₃SiW₁₂O₄₀, H₂O₂	1:2 camphene:H₂O₂, 0.4 mol% catalyst, 333 K; <313 K = no product, >333 K = oligomers	~81% camphene conversion, 46% borneol	[282]
Hydration	PW₄-SBA-15-SO₃H, aqueous acetone (1:1 V/V)	50 °C, 5 reuse cycles, variable catalyst loading	~90% isoborneol selectivity; conversion increases with loading (excess causes mass transfer limitations)	[283]
Esterification (with water)	Tartaric acid–boric acid	Tartaric acid:camphene ratio = 0.25	58.7% camphene conversion, 13.1% isoborneol (water shifts to parallel hydration)	[284]
Esterification (with additives)	Tartaric acid–boric acid + Ti/Zr sulfate	—	55.6% isoborneol (inhibits by-products, promotes isobornyl acetate hydrolysis)	[284]
Solvent-free hydration	Mandelic acid–boric acid	—	26.1% isoborneol (GC content), 55.9% selectivity; saponification yields 100% pure isoborneol	[284]
Acetoxylation	Phosphotungstic acid (PW)	Acetic acid solvent vs. solvent-free	Quantitative isobornyl acetate (acetic acid); ~30% yield (solvent-free)	[285]

Isomerization and interconversion between borneol and isoborneol are catalyzed by chemical and enzymatic systems. Co/TiO₂ selectively isomerizes isoborneol to borneol, achieving >62% borneol content with <0.5% camphor and suppressing dehydration to camphene (a side reaction favored by strongly acidic supports like Mordenite) [286]. Isoborneol dehydrates to camphene via the Wagner−Meerwein rearrangement with Re₂O₇ or H₂SO₄, while (−)-borneol requires 150 °C for camphene conversion; Re₂O₇ also oxidizes borneol to camphor [287]. Enzymatic kinetic resolution enables stereoselective synthesis: EstB from Burkholderia gladioli shows high enantioselectivity for rac-isobornyl butyrate, producing (+)-isoborneol with >98% ee, while EstC from Rhodococcus rhodochrous selectively hydrolyzes rac-bornyl butyrate to yield (−)-borneol with 97% ee (both enzymes prefer butyryl esters over acetates for higher selectivity) [288]. Salvia officinalis dehydrogenases SoBDH1 and SoBDH2 exhibit stereoselectivity for (+)-borneol (converting it but not (−)-borneol) and prefer (+)-isoborneol in racemic mixtures, with SoBDH1 showing outstanding selectivity (E > 200) [289].

Structural characterization of synthetic products relies on FT-IR, ¹H and ¹³C NMR for camphene oxidation products [282], and 1D/2D NMR, elemental analysis, and X-ray crystallography for functional isoborneol derivatives from camphor acylation and rearrangement [290]. Synthetic borneol brands (e.g., "Cheng Yi," "Qing Shan," "Xin Long") contain both borneol and isoborneol, while natural grades vary: common semi-synthetic grade has only (−)-isoborneol, and special grade is pure (+)-borneol [291].

Degradation pathways for these monoterpenoids include enzymatic oxidation: CYP101B1 oxidizes isobornyl acetate to 5-exo-isobornyl acetate and bornyl acetate to 9-hydroxybornyl acetate, with higher activity toward acetates than parent alcohols [292]. Isoborneol is oxidized almost quantitatively to camphor using Fe₃O₄@SiO₂/Ru(OH)ₓ [293]. Among lactic acid bacteria, only alpha-campholenal undergoes degradation, forming a tentative borneol isomer [294].

For 2-methylisoborneol (2-MIB), biosynthesis from geranyl diphosphate (GPP) involves geranyl diphosphate 2-methyltransferase and M IB synthase [295]. Enzymatic synthesis via 2-methylisoborneol synthase (MIBS) converts 2-methylgeranyl diphosphate (2-MeGPP) to (−)-2-MIB (89%) as the major product, alongside 2-methylenebornane (10%), 1-methylcamphene (<1%), and 2-methyl-2-bornene (<1%) [296]. 2-MeGPP can be generated in engineered yeast via Pseudanabaena limnetica GPP methyltransferase (PlGPP MT), with subsequent PlMIBS expression confirming 2-MIB production via degradation product detection [8 49]. MIBS also accepts 2-methylneryl diphosphate ( 2-Me

N PP) as a substrate, yielding (−)-2-MIB (17%), 2-methylenebornane (2 6%), 2-meth

yllimonene (39%), and 2

Biosynthetic Mechanisms and Gene Cluster Regulation of Borneol (Focus on Rosmarinus officinalis), Isoborneol, and 2-Methylisoborneol

Borneol, a bicyclic monoterpenoid, is biosynthesized via bornyl diphosphate synthase (BPPS) from the terpene synthase b (TPS-b) clade [297]. For instance, Artemisia argyi’s AarTPS89 produces (+)-borneol as a single product from geranyl diphosphate (GPP) in vitro [298]. In Lauraceae species, BPPS enzymes drive borneol chemotype formation; phylogenetic analysis divides Lauraceae TPS-b into B-I to B-V clades, with B-III to B-V correlating with borneol synthesis efficiency [297]. Additionally, (+)-bornyl diphosphate synthase forms bornyl diphosphate, which can be hydrolyzed to borneol [299].

Borneol Modification Enzymes and Substrate Specificities Across Plant Species

Organism	Enzyme(s)	Substrate(s)	Product(s)	Key Observations	Citations
Artemisia argyi	AarBDH4, AarBDH5	(+)-borneol, NAD+	(+)-camphor	—	[298]
Cuminum sativum	Borneol dehydrogenase	Borneol	Camphor	—	[300]
Limonium variety LM-3	— (suppressed BDH)	Borneol	— (reduced camphor)	Higher borneol accumulation linked to suppressed dehydrogenation to camphor	[301]
Salvia rosmarinus	SrBDH1, SrBDH2	Endo/exo-borneol (SrBDH1); borneol (SrBDH2)	Camphor	SrBDH1 has enantiospecificity (E>200); SrBDH2 acts on borneol	[302], [303], [289]
Salvia officinalis	SoBDH2	(+)-borneol (not (−)-borneol)	Camphor	CryoEM structure reveals Ser156-Lys169-Tyr173 catalytic motif and key interactions	[304], [302]
Alpinia villosum	WvBAT3, WvBAT4	(−)-borneol, (+)-borneol	Bornyl acetate	Accept both borneol enantiomers	[305]
Alpinia villosum	WvBAT1–8	Isoborneol	Isobornyl acetate	Convert isoborneol instead of borneol	[305]
Alpinia villosum	Wv_032842	— (gene association)	— (bornyl acetate)	Key gene linked to differential bornyl acetate content between varieties	[306]

For 2-methylisoborneol (2-MIB), cyanobacterial strains like Pseudanabaena sp. dqh15 and Planktothricoides raciborskii CHAB 3331 produce 2-MIB via a SAM-dependent methyltransferase (mtf) and 2-MIB cyclase (mic) [7], with mic functionally annotated as a terpene cyclase [7]. Freshwater cyanobacterium Pseudanabaena foetida var. intermedia NIES-512 has a 2-MIB gene cluster (cnbA, mtf, mtc, cnbB), where mtf and mtc form a transcription unit; heterologous expression in E. coli showed both genes are essential for 2-MIB synthesis [307]. Homologous mtf-mtc operons exist in Pseudanabaena and Planktothricoides strains [308]. In Streptomyces, 2-MIB synthase (MIBSg from S. griseus) and related enzymes contribute to biosynthesis [309]; 2-MIB synthase (2-MIBS) catalyzes cyclization of 2-methylgeranyl pyrophosphate (2-MeGPP), a non-canonical isoprenoid substrate [310], [311]. Most 2-MIBS enzymes have a disordered proline/glycine/alanine-rich N-terminal domain and a C-terminal terpene cyclase domain [310], [311], [312]; the N-terminal domain of S. coelicolor 2MIBS acts as a gatekeeper limiting 2-MIB production and enhances solubility/stability [312]. Phylogenetic analysis of 2-MIBS homologs identifies three branches, with higher conservation in terpene cyclase domains than N-terminal cargo loading domains (CLDs); CLDs have conserved motifs like GPxGLGT, with some clusters having LPGPP [310], [311]. Actinobacterial 2-MIB clusters often include a SAM-dependent methyltransferase (GPP→2-MeGPP) and may associate with Family 2B encapsulin shell proteins (non-essential) [310], [313]. The Ikeda group identified monoterpene cyclase/SAM-methyltransferase transcription units in 7 actinomycetes, detecting 2-MIB production in 4 Streptomyces species; heterologous expression in S. avermitilis conferred 2-MIB synthesis [314]. S. coelicolor 2-MIB biosynthesis involves GPP→2-MeGPP (methyltransferase) then cyclization to 2-MIB (monoterpene cyclase, Mg²⁺-dependent)—opposite the typical “cyclization first, modification later” terpenoid pathway [314]. 2-MIB biosynthetic genes/enzymes are extensively characterized [315]. Cationic intermediates en route to 2-MIB produce homomonoterpene byproducts (e.g., 2-methyllinalool, 2-methyl-β-fenchol) [316]; feeding experiments with [methyl-²H₃]methionine and [1-¹³C]-1-deoxy-d-xylulose supported rearrangement of the 2-methylbornyl cation for 2-methyl-β-fenchol and 1-methylcamphene formation [316]. Micromonospora olivasterospora headspace extracts showed high ¹³C incorporation into 2-MIB and related compounds [316]; ¹³C NMR signals indicated 2-methylterpinyl cation cyclization to 2-methylbornyl cation via Re face attack, mediated by a cation–π interaction with F309 in 2-MIBS [316]. 2-MIB biosynthesis requires geranyl diphosphate 2-methyltransferase and MIB synthase [295]; five Streptomyces collinus Tü 365 terpene clusters include 2-MIB biosynthetic genes [317].

Environmental Regulation of 2-MIB Biosynthesis

Factor	Organism/System	Effect on Gene Expression/Concentration	Citations
Light	Pseudanabaena sp. dqh15; P. raciborskii CHAB 3331	Low light upregulates mtf/mic transcription; high light/darkness inhibits it	[7]
Temperature	Pseudanabaena foetida var. intermedia NIES-512	15 °C and 35 °C upregulate mtf/mtc expression	[318]
Seasonal temperature	Multiple reservoirs	Highest 2-MIB concentrations at 10.3–13.7 °C (cooler months)	[217], [319]
mibC gene copy number	Multiple reservoirs	Correlates with total/cell-bound 2-MIB (R²=0.656–0.987, p<0.01)	[320]
mic gene copy number	—	Strong positive linear correlation with 2-MIB concentration (R²=0.8478)	[321]
mibC gene expression	—	Peaks late summer–early winter; RNA levels precede 2-MIB increases by 2–4 weeks (r=0.879, p<0.001)	[322]
Chlorophyll a (Chl a)	—	Nonlinear correlation with 2-MIB yield (logarithmic-linear, R²=0.74, p<0.01); mic-chlG RNA correlation (R²=0.85, p<0.01)	[323]
Water turbidity (light spectra)	—	Red-shifted light spectra decrease MIB levels via photosynthetic pigment changes	[323]

Borneol degradation is exemplified by Pseudomonas sp. ATCC17453, which harbors a BDH on the CAM plasmid as part of the camphor degradation pathway; this BDH accepts (+)-, (−)-borneol, and (±)-isoborneol, and uniquely catalyzes camphor reduction to borneol [324]. Rhodococcus wratislaviensis DLC-cam has been described for its ability to transform 2-methylisoborneol [325].

Environmental Factors and Microbial Producers Influencing 2-Methylisoborneol Production

2-Methylisoborneol (2-MIB) is a notorious musty odorant in drinking water systems, produced by diverse microbial taxa including cyanobacteria, actinomycetes, and other bacterial phyla (Bacteroidota, Myxococcota) [742, 753, 770, 779, 786, 806, 1001]. Geosmin and 2-MIB are secondary bacterial metabolites causing earthy-musty taste and odour (T&O) in drinking water, with low odour thresholds that make them leading causes of global customer complaints to water companies [6].

2-MIB-Producing Microbial Taxa and Strains

Microbial Group	Strains/Taxa	Geographic Origin/Context	Citations
Cyanobacteria	Pseudanabaena sp. dqh15, Planktothricoides raciborskii CHAB 3331	Lakes in China	[7]
Cyanobacteria	Pseudanabaena sp. PD34, PD35	South Korea	[203]
Cyanobacteria	P. yagii (GIHE-NHR1)	Japan	[217]
Cyanobacteria	Pseudanabaena foetida var. intermedia NIES-512	Not specified	[318]
Actinobacteria	Streptomyces strains T-S1, T-S2	Not specified	[205]
Actinobacteria	Streptomyces sp.	Not specified	[23]
Other Bacterial Phyla	Bacteroidota (MAG0848), Myxococcota (MAG0873)	Potential producers	[207]

The biosynthesis of 2-MIB relies on two key genes: the S-adenosylmethionine (SAM)-dependent methyltransferase gene (mtf) and the 2-MIB cyclase gene (mic, also called mibC or mtc). In Pseudanabaena sp. dqh15, mtf (870 bp) and mic (1194 bp) are 95 bp apart; in Planktothricoides raciborskii CHAB 3331, mtf (864 bp) and mic (1170 bp) are 96 bp apart [7]. The mic genes of these strains share 43.3% and 44.8% DNA sequence identity with sco7700 (a known terpene cyclase gene) and are annotated as Terpene cyclase non-plant C1 [7]. In P. yagii GIHE-NHR1, 2-MIB biosynthesis genes lie between cyclic nucleotide binding protein genes (cnbA and B), with two MIB synthase motifs (DDYYADDTE and NDLLSVAKD) present [217]. The mibC gene, encoding a critical monoterpene cyclase, is a target for evaluating 2-MIB production potential [319].

Temperature Effects on 2-MIB Production and Gene Expression Across Producers

Producer Strain/Taxa	Key Temperature-Related Observations	Citations
Pseudanabaena sp. dqh15	Growth and MIB production vary with temperature (10°C, 25°C, 35°C)	[202]
Pseudanabaena sp. PD34, PD35	Maximum 2-MIB concentrations at 25°C (570 μg/L, 56 μg/L); yields per cell/copy increase with temperature, but mic expression is higher at low temperatures	[203]
P. foetida var. intermedia NIES-512	Highest 2-MIB concentrations/productivity at 35°C; mtf/mtc expression upregulated at 15°C and 35°C vs. 25°C	[318]
Streptomyces strains T-S1, T-S2	Optimal 2-MIB production at 25°C; reduced production at 30°C and 35°C	[205]
Field studies (P. yagii context)	2-MIB concentrations peak in November (up to 204 ng/L) at 10.3–13.7°C	[217]
Gong-ji Stream	Highest 2-MIB concentrations (49 ng/L) between August and November	[319]

Environmental factors significantly influence 2-MIB production and gene expression. Light intensity modulates mtf and mic transcription: low light increases transcription by 30% (mtf) and 60% (mic) within 3–12 h, while high light decreases it by 30% and 50%, respectively [7]. Darkness at 25°C for 72 h inhibits expression, reducing mRNA levels by 40–80% [7].

The abundance of 2-MIB biosynthesis genes correlates with 2-MIB concentrations. In Gong-ji Stream, mibC copy numbers (water column: 4.4 × 10⁷ copies/mL; sediment: 9.8 × 10⁴ copies/mL) show temporal patterns matching 2-MIB levels, with significant correlations between mibC copy number, gene expression, and 2-MIB concentrations (r = 0.644–0.749) [319]. In multiple reservoirs, mibC copies correlate with total and cell-bound 2-MIB (R² = 0.302–0.987) [320], and eRNA expression of mibC strongly correlates with 2-MIB levels (r = 0.879) and precedes increases by 2–4 weeks [322]. In Jinpen and Xikeng reservoirs, mic gene abundance peaks in winter (5.42 × 10⁴ copies/L in XK), with cyanobacteria producing 2-MIB in summer surface layers and actinomycetes in winter and bottom waters [24]. Sediment 2-MIB concentrations (11.7–49.6 ng/g) are driven by total nitrogen and organic matter, correlating with Streptomyces sp. [23].

2-MIB is produced by cyanobacteria during photosynthetic pigment biosynthesis [323]. Its yield correlates nonlinearly with chlorophyll a (Chl a) content (logarithmic-linear model, R² = 0.74, p < 0.01) [323], supported by a strong correlation between mic and chlG gene expression (R² = 0.85, p < 0.01) [323]. The model shows <2% of carbon flux is allocated to MIB biosynthesis vs. Chl a, indicating synergistic (not competitive) production [323]. Increased water turbidity, causing a red-shift in light spectra, alters photosynthetic pigments and decreases MIB levels [323]. Random Forest (RF) analyses accurately classify samples for high/low geosmin and 2-MIB concentrations, demonstrating the predictive power of the biological consortium [6].

Advanced Oxidation and Biodegradation Strategies for 2-Methylisoborneol Removal

2-Methylisoborneol (2-MIB) is a prevalent taste and odor (T&O) compound in water, with raw water concentrations during algal blooms reaching up to 40 ng/L in some water treatment plant (WTP) intakes [326] and 25 ng/L in Lake Manatee, Florida [327]. Meeting typical odor threshold concentrations (OTCs) of ~10 ng/L [327] requires effective 2-MIB removal, which can be achieved via biodegradation, advanced oxidation processes (AOPs), and adsorption.

Biodegradation strategies include bacterial isolates and bioflocs: a Lake Manatee isolate depleted 25 ng/L 2-MIB by 66% to below the OTC (9.6 ± 0.3 ng/L) with no residual odor [327]; bioflocs in sequencing granular reactors (SGRs) achieved 78.66–81.5% removal of 100–700 ng/L 2-MIB within 48 h (8.49% biological, remainder physical/chemical adsorption) [328]; anaerobic digestion sludge removed 2-MIB at 144.65 ng L⁻¹ day⁻¹ under nonaerated conditions, with bacterial isolates demonstrating removal rates of 1.0 × 10⁻⁶ to 1.1 × 10⁻³ ng h⁻¹ cell⁻¹ (aerobic) and 2.5 × 10⁻⁵ to 2.2 × 10⁻³ ng h⁻¹ cell⁻¹ (nonaerated) [329].

AOPs exhibit varying efficacy for 2-MIB removal, with key performance metrics summarized below:

2-MIB Removal Efficacy of Advanced Oxidation Processes (AOPs)

AOP Type	Initial 2-MIB Concentration	Removal Efficiency/Outcome	Key Mechanism/Notes	Citation
Sole ozonation	Not specified	29.1% removal in 30 min	N/A	[330]
HAO-catalyzed ozonation	Not specified	27.5% removal (minimal enhancement over sole ozonation)	Surface adsorption	[330]
RAO-catalyzed ozonation	Not specified	98.4% removal	Hydroxyl radical (•OH) oxidation	[330]
UV/chlorine	100 ng/L	>95% removal in 3 min	Dominant reactive species: •OH	[331]
UV-C photolysis alone	Not specified	>80% removal in 1 h	N/A	[332]
UV/chlorine (extended)	Not specified	Complete degradation in 1 h (chloroform byproducts formed)	N/A	[332]
Fe-N co-doped TiO₂ photocatalysis	Not specified	99.78% removal (0.001% Fe, 0.5% N doping; visible light 400–780 nm)	Reactive species: •OH, O₂•⁻, photogenerated holes (h⁺)	[333]
Photo-Fenton (UV/Fe(II)/H₂O₂)	Not specified	80.73% removal (outperformed UV, UV/H₂O₂, Fenton processes)	•OH-mediated dehydration (2-methylenebornane, 2-methyl-2-bornene) and ring-opening	[334]
UV-assisted photoelectrochemical	Not specified	95% removal in 25 min	Reactive species: •OH, Cl•, ClO•	[335]
O₃ + UV (15.84 mg/L O₃)	Not specified	Reduced 2-MIB below OTC in 30 min (improved over sole ozonation)	N/A	[336]
H₂O₂ (20 mg/L)	Not specified	16.0 ± 0.4% removal after 8 h (dose-dependent)	N/A	[337]

Adsorption is a common WTP barrier: virgin granular activated carbon (GAC) effectively removed 2-MIB, but breakthrough increased with bed age (14–20 × 10³ to 36 × 10³ bed volumes) [326]; used GAC removed 10–40% (25 cm depth) and ~65% (128 cm depth), with geosmin more readily adsorbed than 2-MIB [326]; aluminum (hydroxyl) oxides (HAO, RAO) adsorbed 2-MIB via surface hydroxyl groups, with HAO having a higher maximum capacity (0.9188 μg mg⁻¹) than RAO (0.8394 μg mg⁻¹) [330].

2-MIB biosynthesis involves two enzymes: geranyl diphosphate methyltransferase (GPPMT) converts geranyl diphosphate (GPP) to 2-methyl-GPP, and 2-methylisoborneol synthase (MIBS) cyclizes 2-methyl-GPP to 2-MIB (MIBS kcat/Km = 1.45×10³ M⁻¹s⁻¹) [338]. Degradation intermediates vary by process: UV/chlorine produces 2-methylenebornane, 2-methyl-2-bornene, endo-borneol, camphor, 3,5,5-trimethyl-2-cyclopenten-1-one, and 4-methyl-hept-2-ene [331]; Fe-N co-doped TiO₂ photocatalysis forms dehydration (M1, M2), demethylation (camphor, M3), and ring-opening (alcohols M4, M5; aldehydes M7, M9; ketones M6, M8) products [333]; photo-Fenton generates 2-methylenebornane, 2-methyl-2-bornene, camphor, 2-ethyl-1-hexanol, nonanal, and isooctyl alcohol [334].

Extraction, Detection, and Quantification Methods for Borneol, Isoborneol, and 2-Methylisoborneol

Structural Classification and Occurrence of Borneol, Isoborneol, and 2-Methylisoborneol Monoterpenoids

Borneol is a bicyclic monoterpenoid that co-occurs with structurally related compounds (e.g., camphor, bornyl acetate) in various plant essential oils (EOs), sharing the same bicyclic structure as camphor and being easily oxidizable to it [261]. It is a major or key component in numerous natural sources and commercial products, with its distribution, content, and related properties summarized below:

Borneol Distribution, Content, and Commercial Purity

Source	Borneol Content/Purity	Reference
Inula macrocephala EO	26.4%	[339]
Rhododendron mucronulatum EO	27.74%	[159]
Salvia dolomitica EO	5.86%	[340]
Tansy oil	1–3%	[341]
Melissa officinalis EO	Main monoterpenoid component (alongside 1,8-cineole, camphor, citronellal)	[196]
Spanish sage EO (corolla)	Highest content among plant organs	[342]
Fir honeydew honey	0.4–5.9% (aids source traceability)	[343]
Alpinia villosum	Key active ingredient (substrate for bornyl acetate/camphor biosynthesis)	[306]
Amber extracts	Detected	[344], [345]
Wood extracts	Detected	[346]
Phloem samples	Detected	[347]
Cannabis terpene mixtures	Detected	[348]
Certain volatile profiles	3.1–3.6%	[349]
Rosmarinus officinalis EO	One of seven predominant compounds (with α-pinene, camphene, 1,8-cineole, camphor, verbenone, bornyl acetate)	[111]
Lemon-lime carbonated beverages	Detected (contributes camphorous notes)	[350]
Commercial (+)-borneol (32b) standard	96.5% purity (3.5% isoborneol impurity)	[351]
Commercial analytical standard	≥95% purity (supplier: Sigma-Aldrich)	[352]

Isoborneol, an epimer of borneol, is similarly widely distributed across natural and synthetic sources, with key details consolidated below:

Isoborneol Distribution, Content, and Commercial Purity

Source	Isoborneol Content/Purity	Reference
Amber extracts	Detected	[344], [345]
CTLL ethanolic formulation	7.88%	[353]
Curcuma zedoaria EO	13.5%	[180]
Cannabis terpene mixtures	Detected	[348]
Sun-dried ‘Guiyan1’ samples	7.69 ± 1.39 μg g⁻¹	[354]
Hot air-dried ‘Guiyan1’ samples	11.78 ± 1.45 μg g⁻¹	[354]
Common grade natural borneol (semi-synthetic)	Present	[291]
Savory	Detected as a terpene	[355]
Lavandula angustifolia Mill. oil	3.61% relative abundance	[356]
Lemon-lime carbonated beverages	Detected (camphorous notes)	[350]
Commercial cola	Detected as a racemic mixture	[351]
Commercial isoborneol standard	98.7% purity (1.3% borneol impurity)	[351]
Certain plant samples	Potential chemical marker (with borneol, camphor, etc.)	[357]

2-Methylisoborneol (2-MIB), a non-canonical monoterpene, is primarily known for causing musty/earthy water odor alongside geosmin, produced by various microorganisms [1]. It is detected in Hy samples at 19.2% relative abundance via LVI-GC/MS [1], can be synthesized from camphor [309], and is biosynthesized from geranyl diphosphate via geranyl diphosphate 2-methyltransferase and MIB synthase [295]. Commercial 2-MIB standards (99.3% purity) are available from suppliers like Sigma-Aldrich [295], with GC-MS quantification showing a method detection limit (MDL) of 0.042 μg L⁻¹ and method quantification limit (MQL) of 0.126 μg L⁻¹ for direct hexane injection [295].

For analytical purposes, borneol is commonly quantified via gas chromatography–mass spectrometry (GC-MS); for example, the Agilent 7890B-5977B GC-MS system determined no significant borneol level differences between A. villosum varieties [306]. In M. officinalis EO, borneol content increases with room-temperature storage but remains stable at 4 °C and −20 °C [196]. Borneol can be identified via GC-MS by NIST library and authentic compound comparison [358], or via APCI-QTRAP MS through protonated borneol (m/z 155) dissociation patterns [359]. Classified as a volatile compound (boiling point ~160–220 °C) alongside camphor and eucalyptol [261], it is extracted and detected via methods like dichloromethane:methanol (1:1) sonication + GC-MS (DB-5MS column) for amber samples [344], hexane extraction (pentadecane internal standard) + GC-flame ionization detection (FID) for phloem samples [347], and headspace solid-phase microextraction (HS-SPME)-GC-MS for microbial terpene analysis [294]. In R. officinalis EO, borneol is quantified via GC-FID (HP-5 column) with the internal standard method and calibration curves [111].

Isoborneol is detected via GC-MS [344][353][354][180][348] and thermal desorption GC/MS [360], confirmed by mass spectral and retention time comparison to references [360]. Quantification uses selected ion monitoring (SIM) in GC-MS with m/z 95 [357]. Like borneol, it is analyzed in R. officinalis EO via GC-MS (HP-5MS column) using C9-C23 aliphatic hydrocarbon retention indices and NIST/EPA/NIH 2008 library matching [111]. Borneol recovery efficiency in wood samples ranges from 75–110% (average 93%) when spiked with known amounts [346]. Isoborneol’s poor water solubility requires methanol pre-dissolution for analysis [361], and its presence can be distinguished from methanol using chemical sensors [361].

Borneol Isolation and Quantification from Rosmarinus officinalis via Extraction and Analytical Techniques

Borneol is a constituent of Rosmarinus officinalis essential oils (EOs), with reported relative abundances varying widely across studies (Table 1). Isoborneol is also present in R. officinalis EOs, with relative abundances of 8.1% in a hydrodistilled sample [139] and 2.28–9.8% across EOs extracted via solvent-free microwave extraction (SFME), microwave-assisted hydrodistillation (MAHD), steam distillation (SD), and hydrodistillation (HD) [88]. 2-Methylisoborneol was not detected in the analyzed R. officinalis EO compositions.

Borneol Content in R. officinalis EOs by Extraction Method and Source

Extraction Method/Source	Borneol Content	Citation(s)
Hydrodistilled EO	4.1%	[73]
Whole aerial part EOs	1.7–2.5%	[79]
Leaf EOs	1.9–2.8%	[79]
Steam-distilled EO	Up to 8.72%	[232]
Supercritical fluid extraction (SFE) extract	20–24 g/kg extract	[269]
Hydrodistilled EO	12%	[90]
Simultaneous hydrodistillation-steam distillation (SHSD)	3.7%	[91]
SHSD with carbon dioxide (SHSDACD)	5.2%	[91]
Supercritical CO₂ (SC-CO₂) extracted oil	18.79%	[93]
Steam-distilled EO (two collection periods)	2.11% and 1.91%	[98]
Wild R. officinalis EO	Up to 24%	[99]
Commercial R. officinalis EO	3.81%	[100]
Cultivated R. officinalis EO	2.2%	[104]
GC-MS-analyzed EO	5.23%	[105]
Seasonal harvests (combined with α-terpineol)	3.73–5.32%	[108]
Hydrodistilled EO (Jordanian R. officinalis)	8.7%	[113]
Hydrodistilled EO (Tunisian R. officinalis)	9.37%	[119]
GC-analyzed EOs	3.6–5.9%	[58]
Seasonal samples (Serbian R. officinalis)	4.4–9.5%	[120]
Aqueous extract-treated R. officinalis EO	7.20%	[122]
Acetone extract-treated R. officinalis EO	8.80%	[122]
SC-CO₂-extracted rosemary oleoresin	4.33%	[125]
SC-CO₂ extract (first step)	4.6%	[362]
SC-CO₂ extract (second step)	8.28%	[362]
Steam-distilled EO (Sardinian R. officinalis)	10.2%	[130]
Hydrodistilled (HD) EO (Algerian R. officinalis)	4.14%	[131]
Microwave hydrodistillation (MHG) EO (Algerian R. officinalis)	5.01%	[131]
Microwave-assisted extraction (ME) and Clevenger hydrodistillation (CH) (wild and cultivated)	0.53–1.67%	[241]

Extraction methods for R. officinalis EOs containing borneol and isoborneol include hydrodistillation (typically 3–4 hours using a Clevenger-type apparatus) [363][232][139][364][365][108][113][119][132][241][148], with variations in sample size and duration: 50 g of dried aerial sections processed for 4 hours [364]; 500 g of ground Jordanian aerial parts for 4 hours [113]; 300 g of ground Tunisian aerial parts for 4 hours [119]; 100 g of dried Algerian aerial parts for 3 hours [132]; and 50 g of fresh herb for 90 minutes [266]. Other methods include simultaneous hydrodistillation-steam distillation (SHSD) [366][91], SHSDACD (yielding 2.8% v/w at 30 minutes vs. 2.0% v/w at 120 minutes for SHSD) [91], SFE (40 °C, 30 MPa, CO₂-to-rosemary ratio 2.5 g/g) [269], SC-CO₂ extraction (conditions: 300 bar/313 K [362]; 180 bar/50 °C, CO₂ flow rate 1 g/min [125]) [93][125][362][266], SFME, MAHD, and SD [88], MHG (extracting 5.01% borneol vs. 4.14% via HD) [131], ME (with high EO trait records except for limonene, camphor, and verbenone, which are better expressed in CH) [241], HUP-MHD (advantageous for separating rosemary oil and oxygenated components like borneol) [367], hexane:acetone extraction (70:30 ratio) [266], and stomached extraction with hexane:acetone (70:30 ratio) [266]. Steam distillation parameters include 15 kg/h steam at 50 kPa for 30 minutes per batch (30 mm twigs) [98] or 90 minutes after 4-hour maceration [148]. Solid-phase microextraction (SPME) with polydimethylsiloxane (PDMS) fiber is used for qualitative/quantitative analysis of borneol, showing a linear response and strong correlation with distillation data (correlation coefficient 0.8775) [368]. Headspace SPME (HS-SPME) combined with GC-MS [150] and HS-SPME with an Rt-β-DEXsm enantioselective column (for cultivar discrimination) [369] are also employed; MAE–HS-SPME aligns well with steam distillation for quality evaluation [370].

Analytical techniques for detecting and quantifying borneol and isoborneol include gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). GC-FID uses columns such as DB5 (60 m × 0.32 mm id) [363], HP-5 MS (30 m × 0.25 mm i.d.) [139], DB-5 (30 m×0.25 mm, 0.25 μm film) [148], and OPTIMA-5 (30 m × 0.25 mm; 0.25 μm) [113], with temperature programming (e.g., 50–250 °C at 4 °C/min [363], 60–250 °C at 3 °C/min [113]). GC-MS employs columns including TG-5MS (60 m × 0.25 mm × 0.25 µm) [232], DB-5 (30 m × 0.25 mm i.d.) [139][364][113][148], DB-5MS (10 m × 0.18 µm) [371], HP-5 (30 m × 0.25 mm × 0.25 µm) [365], DB-WAX UI (60 m × 0.25 mm × 0.5 µm) [98], and HP-5 MS (30 m × 0.32 mm I.D., 0.25 µm) [125], with identification via mass spectral libraries (NIST/EPA/NIH, Pherobase, NIST 14, Wiley 10, Chromessence, WILEY, NIST, ADAMS-2007) and authentic standards [232][139][371][364][365][98][113][125][148]. GC-MS conditions include injector temperatures of 200–250 °C, split ratios of 1:10 to 1:100, carrier gases (helium/hydrogen) at 1.0 mL/min, and temperature programming (e.g., 60–250 °C at 3 °C/min [364][113], 40–260 °C at 4 °C/min then 260–310 °C at 60 °C/min [365]). Retention indices (RI) calculated using n-alkane series (C6–C40 [365], C8–C24 [108], C8–C20 [364][113], C7–C25 [148]) aid identification [364][365][98][108][113][148]; two columns of opposed polarity resolve co-elution issues [137]. Bidimensional gas chromatography (MDGC) separates borneol and isoborneol enantiomers, with isoborneol showing enantiomeric ratios of 7.25 (−) and 9.68 (+) [372]. Borneol in R. officinalis has high optical purity of the minus form (over 82%) [368]; enantiomeric excess varies by source (larger in Spanish rosemary oil) and is only detected at >0.5% [373].

Quantification methods include external standard calibration [366] and internal standard addition prior to distillation [368]. SFE extracts report borneol as 20–24 g/kg [269]. In sage EO (a related herb), borneol was quantified at 12.70 mg/g via GC-FID [374]. Authentic standards (e.g., (+)-, (−)-, and (±)-isoborneol from Sigma-Aldrich) are used for peak identification [375][372][376][113][125][370][377]; stock solutions (5.0 mg mL⁻¹) are prepared in methanol [370] or ethyl acetate [377]. Relative area percentage (individual peak area/total peak area × 100) is common for quantification [364][90][365][98][104][105][108][113][119][58][120][122][130][131][132][148]. Calibration solutions range from 5.0 to 1000 μg mL⁻¹ [370] or 0.05–10 µg/mL [377], with calibration curves: Y = 7.86X + 0.53 (R² = 0.9997) [370] and Y = 25.01X – 0.20 (R² = 0.9990) [377]. Linear ranges are 0.05–10 mg g⁻¹ [370] or 0.05–10 µg/mL [377], with RSD values of 10.8% [370] or 5.6% [377] and recoveries of 94% [370] or 95% [377].

2-Methylisoborneol Production, Detection, and Fate in Aquatic and Aquaculture Systems

2-Methylisoborneol (MIB, [1R-exo]-1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol) is a non-canonical monoterpene responsible for musty and earthy odors in water, often produced by microorganisms [1][9]. Its production is linked to genes such as mibC (encoding the essential 2-MIB synthase) [319]; mibC sequences from Streptomyces griseus subsp. griseus (MIBSg) and Streptomyces coelicolor A3(2) (MIBSc) have been codon-optimized for E. coli expression [309]. Phylogenetic analysis of environmental mibC genes showed 100% similarity to Pseudanabaena yagii and 95.79% similarity to Pseudanabaena sp. dph15 [217]. The MIB-producing gene mic has also been detected in Planktothrix raciborskii NW-1 [204], and new MIB synthase sequences from 10 cyanobacterial strains showed 82–95% nucleotide similarity and 83.6% conserved protein sequences, forming a separate phylogenetic cluster from actinobacterial MIB synthases [378]. MIB biosynthesis occurs via conversion of geranyl diphosphate (the universal C10 monoterpene precursor) by geranyl diphosphate 2-methyltransferase and MIB synthase [295]. A Pseudanabaena species isolated from a biofilm sample was confirmed as a MIB producer [379].

Production conditions for MIB vary by organism, with key findings summarized below:

MIB Production Conditions and Concentrations by Organism/System

Organism/System	Key Conditions	MIB Concentration	Reference
P. raciborskii NW-1	Optimal growth: 33 °C, 10 μmol photons s⁻¹ m⁻²; high light (60 μmol photons s⁻¹ m⁻²)	Total: 1.87 ± 0.04 pg/cell; extracellular: 0.33 ± 0.05 pg/cell	[204]
Unspecified strains	Low temperatures (10.3–13.7 °C)	204 ng/L (November)	[217]
P. yagii	Lower temperatures	~24,000 ng/L (6 days); ~30,000 ng/L (9 days)	[217]
Pseudonocardiaceae	Not specified	8.60–429.67 ng/mL	[9]
RAS sludge (drum filter)	Not specified	Max production rate: 1.781 ng g⁻¹ h⁻¹	[12]
RAS sludge (trickling filter)	Not specified	Max production rate: 3.786 ng g⁻¹ h⁻¹	[12]
Streptomyces roseoflavus/S. thermocarboxydus (RAS)	Aerobic/anoxic conditions (higher production under aerobic)	Not specified	[12][380]

MIB production also occurs via methyl addition to a monoterpene precursor [69], with producers including actinomycetes (streptomycetes), fungi [69], and cyanobacteria (e.g., Oscillatoria and Planktothrix strains, which also produce geosmin) [378]. In recirculating aquaculture systems (RAS), Streptomyces is a main MIB producer [381][380], though the MIB-synthesis gene tpc was not detected in RAS units in one study [382]. RAS popularity is threatened by MIB and geosmin (GSM) accumulation, as their lipophilic nature and high bioaccumulation rate reduce fish product quality and marketability [383]. MIB production by streptomycetes coincides with aerial mycelium and spore development [69].

Detection of MIB (often alongside GSM) uses techniques like gas chromatography-mass spectrometry (GC-MS) with selected ion monitoring (SIM), targeting m/z 95, 108, and 135 (with m/z 95 as the most abundant fragment) [384][385][386][378]. Sample preparation methods and their performance are summarized below:

MIB Detection Methods and Performance Metrics

Method	Key Parameters	Detection Limit (LOD/MDL)	Reference
SPME (DVB/CAR/PDMS fibers)	Widely employed; most suitable fiber type	Optimized HS-SPME: 0.25 ng/L	[386][387][378][388]
Vacuum headspace SPME (Vac-HSSPME)	30-minute sampling time	Enhanced sensitivity (not specified)	[389]
HS-SPME (deionized water)	Not specified	0.81 ng/L	[390]
GC-MS (other methods)	Not specified	2.4 ng/L	[391]
Stir bar sorptive extraction (SBSE)	Linearity: 0.3–100 ng/L	~0.3 ng/L	[392]
Purge and trap GC-MS (PT-GC/MS)	Japanese Standard Drinking Water Examination Methods	1 ng/L; 1.0 ng/L	[393][394][395]
In-tube extraction (ITEX)	Not specified	0.03 µg/L	[396]
LC-APCI/MS (Agilent Zorbax Eclipse Plus C18 column)	Mobile phase: water/methanol; gradient flow	Not specified	[397]
SBSE-LC-APCI/MS (RAS)	PDMS stir bars (conditioned per protocol)	LOQ: 20 ng/kg; LOD: 6 ng/kg	[397]
SPME-GC-MS	Not specified	1 ng/L	[398]
SPME-GC-MS/MS	Not specified	Subnanogram levels	[398]
SBSE-GC-MS	Not specified	1 ng/L	[398]
Direct injection (hexane solution)	2 μL injection	MDL: 0.042 μg L⁻¹; MQL: 0.126 μg L⁻¹	[295]
GC-MS (improved temperature program)	40 °C (3 min) → 230 °C (10 °C/min, 1 min)	Separates MIB from IBMP	[399]
SPME-GC-MS (fish tissue, modified)	Microwave distillation with DHN internal standard	Not specified	[400]
SPME-GC-MS (fish fillets, modified)	Microwave N₂ purge	LOQ: 1 ng kg⁻¹	[382]
HS-SPME-GC/MS-QTOF (hybrid catfish)	50 min at 70 °C; CWR-PDMS fiber; 30% saturated NaCl	Not specified	[401]
HS-LPME-GC-MS	Optimized solvent/volume/stirring/ionic strength	1.0 ng/L; linear range: 5–1000 ng/L	[402]

MIB standards (purity ≥95% to >99%) are sourced from Sigma-Aldrich [389][403][387][392][390][404], WAKO Pure Chemicals Ltd. [395], Dr. Ehrenstorfer Gmbh [399], or synthesized [69]. Stock solutions (e.g., 100 mg/mL in methanol, 100 μg/mL in hexane) are stored dark at 4 °C [389][403][392][395], while 100 mg/L solutions are stored dark at −20 °C [399]. For fish tissue analysis, factors like 8-hour maximum pre-extraction delay [401], analytical recovery optimization [405], and stable isotope dilution method (SIDM) for recovery correction (106% recovery for trout) [405] are critical. Direct HS-SPME of biological matrices increases bias [405], and distillation yields higher GSM recoveries than direct HS-SPME (trout data) [405].

In aquatic systems, MIB concentrations vary temporally and spatially, with key observations summarized below:

MIB Concentrations in Aquatic Systems

System	Location/Compartment	Concentration	Reference
Nanwan Reservoir	Water	Max: 143.5 ng/L (August)	[204]
Nanwan Reservoir	Sediment	Max: 26.8 ng/g (December)	[204]
Gong-ji Stream	Water	Annual average: 17 ± 15 ng/L (0–49 ng/L); peaks August–November	[319]
Unspecified	Surface sediment	17.70–74.36 ng/kg	[386]
WTP intake	Water	Max: 40 ng/L	[326]
Alabama drinking water reservoir	Water	380 ng/L (summer 2013)	[219]
Wyaralong Reservoir	Surface water	Initial: 47.1 ng L⁻¹; 7-day: 6.9 ng L⁻¹	[394]
Wyaralong Reservoir	Bottom water	Initial: 14.5 ng L⁻¹; 7-day: 2.7 ng L⁻¹	[394]
WTP water	Water	6.73–19.61 ng/L (above OTC: 5–10 ng/L)	[399]
Production ponds	Water	3.2–28.5 ng/L	[406]
Depuration ponds	Water	1.2–10.6 ng/L	[406]
RAS tank water	Water	< LOD to 60.3 ng/L (13 weeks; higher with fewer PAA applications)	[381]
RAS drum filter	Water	Max: 260 ng L⁻¹	[12]
RAS trickling filter outlet	Water	Higher than geosmin	[12]
RAS 1 (nursery)	MBB/tank water	Detected; 4-day samples > 7-day samples (degradation)	[397]
RAS 2 (grow-out)	Water	Not detected (anaerobic treatment)	[397]
Soils	Not specified	10× higher than geosmin	[295]

MIB concentrations correlate with water quality parameters (positive: TP, WT, pH, Chl a; negative: TN, DO, SD, DDN, NO3⁻) [204] and mibC gene copy numbers (water: 4.4 × 10⁷ ± 14 × 10⁷ copies/mL; sediment: 9.8 × 10⁴ ± 12.9 × 10⁴ copies/mL; r = 0.644–0.749) [319]. They are higher with combined nutrient addition [219] and correlate with diatom (R² = 0.65) and cyanobacterial (R² = 0.48) biovolumes [219].

In aquaculture, MIB accumulates in fish tissues, with key findings below:

MIB Accumulation in Fish Tissues

Fish Type	Tissue/Product	Concentration	Reference
European whitefish	Fillet	0–32 ng/g; decreases over 16-day depuration	[385]
European whitefish	Neck	Highest levels; decreases over 16-day depuration	[385]
Rainbow trout	Fillet	< LOD to 10.2 ng/g; decreases with weekly PAA applications	[381]
Botargo	Not specified	42.7–95.2 μg/kg (exceeds sensory threshold: 0.1–0.7 μg/kg)	[403]
Unspecified fish	Not specified	4.8–19.7 µg/kg (fusty/mouldy off-odours)	[407]
Unspecified fish	Fillet	Significant positive correlation with tank water (some diets)	[408]
Unspecified fish	Grow-out tank fillets	8 ± 8 ng kg⁻¹	[379]
Unspecified fish	Depuration tank fillets	2 ± 2 ng kg⁻¹	[379]
Catfish byproducts	Not specified	Not detected (assay LOD > 0.01 ppb)	[400]
RAS fish	Flesh	Not detected	[382]
Marshy fish farm fish	Fillet	Highest MIB concentrations (higher than sediments)	[409]

Only the biological MIB form ([1R-exo]-1,2,7,7-tetramethyl-bicyclo-[2,2,1]-heptan-2-ol) exhibits muddy flavor [410]. Sensory thresholds include <0.25 μg/kg for geosmin and ~600 ng kg⁻¹ for MIB in fish flesh [382]. 'Muddy flavor' correlates with MIB in fish [406], though MIB did not correlate with water concentrations [406] and was not responsible for off-flavor in charr (levels below trout detection limit) [379].

The fate of MIB in water involves limited removal by conventional treatments (coagulation, sedimentation, filtration, chlorination) [411] and anthracite filters (8–17%) [412]. Key treatment performance is summarized below:

MIB Removal Efficacy by Water Treatment Methods

Treatment	Key Parameters	Removal Efficiency	Reference
Chlorine (2–10 mg/L)	14 days	5%–16% (no destruction)	[413]
Permanganate (2–10 mg/L)	14 days	5%–16% (no destruction); MnO₂ adsorption: 55.8%–67.5%	[413]
UV-TiO₂ reactor	6 hours	61%	[414]
Granular activated carbon (GAC)	Not specified	Effective; breakthrough increases with bed age	[326][415]
Powdered activated carbon (PAC)	10 mg/L dose (sedimentation)	~55% (natural water; lower than pure water due to NOM)	[415][404]
Ozonation + biological activated carbon (BAC)	22 °C	80–85% (BAC); 55% (ozone alone at 16 °C)	[416][412]
Ozonation + H₂O₂ (0.35 mg/mg H₂O₂/O₃)	16 °C	Improves ozone-only removal	[412]
Cellulose acetate (CA)	pH 7; 10 h pseudo-equilibrium	80.2% (74.2% after 4 regenerations)	[395]
Monoterpene-degrading bacteria (Pseudomonas/Rhodococcus)	Not specified	Produces hydroxylation products and 2-methylcamphene/2-methylenebornane	[380]
RAS digestion basins	Not specified	Reduced concentrations vs. inlet	[12]
Untreated sludge reactors	20 mg/l initial MIB	Complete depletion within 6 days (adsorption + biological)	[417]
Open-flow crude sludge reactors	150 g sludge	Effluent: 40% of influent	[417]
Open-flow crude sludge reactors	50 g sludge	Effluent: 60% of influent	[417]
Outgassed PAC (CZ10554, 550°C/4 h)	Not specified	Adsorption capacity equal to/better than CAAC	[418]

Chlorine slows MIB degradation (rate constants: 5.04 × 10⁻²–1.21 × 10⁻¹ day⁻¹ [no chlorine] vs. 9.79 × 10⁻⁴–1.95 × 10⁻² day⁻¹ [5–10 mg/L chlorine]) [413]. Sludge adsorption of MIB is reversible (42% released at 65°C) [417], with complete removal up to 1.5 mg/l [417]. PAC adsorption is lower than CAAC due to acidic functional groups; outgassing improves performance [418].

Cross-reactivity studies with MIB-BSA conjugates (10 mol MIB/BSA) showed 100% cross-reactivity for MIB, 19.9% for (-)-borneol, 19.6% for (±)-isoborneol, 4% for camphor, and 0% for geosmin [419]. Borneol-BSA (13 mol borneol/BSA) and isoborneol-BSA (15 mol isoborneol/BSA) conjugates were also tested [419]. In objectionable milk, endo-borneol, MIB, and α-terpineol were detected (not in controls); endo-borneol decreased ~5-fold and MIB increased ~4-fold over 14 days [420]. Recombined milk with these terpenoids was perceived as unclean [420], and spiked milk differed significantly from controls (P < 0.01) [420]. Borneol and isoborneol were excluded via retention indices in some analyses [421].

Antimicrobial and Bioactive Properties of Borneol-Containing Extracts from Rosmarinus officinalis

Borneol is a bicyclic monoterpene alcohol that oxidizes easily to camphor, a related bicyclic monoterpenoid[261]. It is present in the essential oils (EOs) of multiple plant species, with varying concentrations across taxa and extraction methods. Isoborneol, a structural isomer of borneol, is also identified in plant extracts, such as a sample analyzed by GC×GC TOFMS (0.99%)[422]. 2-Methylisoborneol is not explicitly mentioned in the provided references.

Borneol Concentrations in Plant Essential Oils

Plant Species	Borneol Concentration	Reference(s)
Thymus sipyleus subsp. sipyleus var. davisianus	3.83%	[220]
Salvia subspicata	2.11% (SD = 0.05)	[169]
Salvia officinalis	8.15%	[176]
Rosmarinus officinalis	8.72%	[232]
Rosmarinus officinalis	12%	[90]
Rosmarinus officinalis (SC-CO₂ extract)	18.79%	[93]
Rosmarinus officinalis	0.4–15.4%	[238]
Rosmarinus officinalis	13.3%	[423]
Rosmarinus officinalis	15.46%	[239]
Rosmarinus officinalis	8.8–10.4%	[424]
Rosmarinus officinalis	5.02%	[132]
Rosmarinus officinalis	0.53–1.67%	[241]
Lavandula angustifolia	1–17%	[167]

Extraction methods significantly influence borneol content. For S. subspicata, microwave-assisted hydrodistillation (MSHD) yields higher borneol (6.09%) than conventional hydrodistillation (HD) (4.21%)[267]. For R. officinalis, supercritical CO₂ (SC-CO₂) extraction produces the highest borneol content (18.79%) compared to other methods[93]; steam distillation of dried leaves yields 8.72% borneol[232]. Hydrodistillation is commonly used for R. officinalis EO extraction, with duration (2–4 h) and yield (0.084%[423], 1.2%[260], 1.8–3.3% v/w[424], 1.9%[425], 1.10–2.85%[241]) varying by plant material and conditions[238][239][260][424][425][132][241]. Microwave-assisted extraction (ME) shows taxon-specific differences: wild rosemary (WR) has higher borneol (1.67%) than cultivated rosemary (CR) (0.53%) under ME[241].

Antimicrobial Activity of Borneol-Containing Extracts and Isolated Borneol

Source	Borneol Content	Target Organism(s)	Activity Result	Reference(s)
T. sipyleus EO	3.83%	Staphylococcus aureus, Pseudomonas fluorescens, P. aeruginosa	Inhibits at 5 μl/ml (S. aureus, P. fluorescens); low activity at 25–50 μl/ml (P. aeruginosa)	[220]
R. officinalis EO	12%	L. monocytogenes ATCC7644, S. aureus STA47	Good inhibitory activity	[90]
R. officinalis SC-CO₂ extract	18.79%	B. subtilis, S. aureus, E. coli, S. typhimurium	~2.5-fold larger inhibition zones vs. HD oil (B. subtilis, S. aureus); ~1.5- and 2.0-fold larger zones (E. coli, S. typhimurium)	[93]
Isolated borneol	N/A	S. oryzae (stored-product pest)	100% mortality at 10 ml/720 ml (24 h); 95% mortality at 0.1 ml/720 ml (7 days)	[279]
S. officinalis EO	8.15%	Klebsiella pneumoniae, Salmonella paratyphi A, Enterococcus faecalis	MIC: 6.25 mg/ml (K. pneumoniae, S. paratyphi A); 12.50 mg/ml (E. faecalis)	[176]
R. officinalis EO	N/A (active)	Gram-positive bacteria (S. aureus, E. faecalis)	Active, MIC values not explicitly reported	[238]
Isolated borneol	N/A	L. innocua	MIC: 5 mg/ml	[266]

Detection and quantification of borneol rely on gas chromatography (GC) techniques, with GC-FID and GC-MS as common methods. Columns used include Rtx®-5 Restek (30 m × 0.25 mm i.d., 0.25 µm film thickness)[167], SE-52 (50 m × 0.25 mm × 1.0 µm)[170], TG-5MS (60 m × 0.25 mm × 0.25 µm)[232], HP-5 (30 m × 250 µm × 0.25 µm)[260], and DB-5 (30 m×0.25 mm, 0.25 μm)[148]. For R. officinalis, GC-FID-MS systems with dual columns (polyethylene glycol and 5% phenyl-95%-methyl silicone, both 60 m × 0.25 mm × 25 μm) enable simultaneous determination of retention indices (RI) on polar and non-polar columns and mass spectra[238]. Identification uses Kovats RI comparisons with n-alkane standards (C6–C24[238], C7–C25[148], C8–C24[260]) and mass spectral matching against libraries (NIST, Adams, Wiley, W9N11.L)[167][170][232][238][260][148]. Quantification employs normalized peak area calculations from FID chromatograms[170][238] or internal standards (e.g., geraniol)[238].

The antimicrobial activity of borneol-containing extracts is linked to structural and mechanistic factors. The hydroxyl functional group is critical for hydrogen bond formation, enhancing activity[261]. Terpenoids also disrupt cell membranes by altering fluidity and permeability[261]. Molecular modeling studies suggest borneol localizes at the phospholipid-water interface, orienting its polar group toward POPC polar heads and lipophilic chain toward the water layer, potentially entrapping lipid radicals via hydrogen donation[107].

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