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Title: Structural Classification and Chemical Characteristics of Borneol-Type Monoterpenoids: A Comprehensive Review of Their Molecular Architecture and Biosynthetic Origins
Natural Occurrence and Distribution of Borneol-Type Monoterpenoids in Plant Species
Structural Classification and Biosynthetic Pathways of Borneol-Type Monoterpenoids
Borneol is a bicyclic monoterpenoid naturally present in the essential oils (EOs) of various plant species, often alongside related compounds such as camphor, 1,8-cineole, and bornyl acetate [1][2]. Its occurrence and concentration vary across plant species, chemotypes, and regions, with some cases documenting it as a major constituent and others as a minor component. Regional variations are observed in EOs of certain plants: EOs of Rosmarinus officinalis (EORO) from Spain have high borneol concentrations, unlike those from Morocco and Tunisia, which are dominated by 1,8-cineole [1]. Specific chemotypes associated with borneol include the cineole-camphor-borneol chemotype found in Israel [3] and the germacrene-D + borneol + bornyl acetate chemotype identified in some plant accessions [2]. Structurally, borneol and camphor share the same biosynthetic pathway, with camphor biosynthesized from borneol via oxidation of its hydroxyl group [1][2]. The broader biosynthesis of terpenes, including borneol, occurs through two pathways—the Mevalonate pathway and the non-mevalonate (MEP/DOXP) pathway—which produce the precursors isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) in cellular organelles like chloroplasts, cytoplasm, and mitochondria [4].
Borneol Concentrations in Plant Essential Oils
| Plant Source/Extract Type | Borneol Concentration | Citations |
|---|---|---|
| Rosemary EO (key terpenoid component) | Not specified (key component) | [4][5] |
| Lavandula angustifolia L. EO (BMO) | 1–17% of total composition | [6] |
| Unspecified plant EO (study 1) | 13.6% | [7] |
| Unspecified plant EO (study 2) | 14.99% | [8] |
| Unspecified plant EO (study 3) | 13.5% | [9] |
| Unspecified plant EO (flowers) | Up to 44.8% | [10] |
| Unspecified plant EO (aerial parts) | 31.2% | [10] |
| Unspecified plant EO (individual) | 52.22% | [11] |
| Rhizome extract | 3.9% | [12] |
| Origanum EO (OEO) | 1.46% | [13] |
| Volatile extract | 2.67% | [14] |
| Dombeya buettneri stem EO | 4.2% | [15] |
| Salvia dolomitica EO | 4.41% | [16] |
| Unspecified plant EO (mean ± SD) | 1.97 ± 0.01% | [17] |
| Unspecified plant EO (range) | 2.0–3.0% | [18] |
| Tanacetum vulgare (tansy) flower/leaf extract | Not specified (detected) | [19] |
| Picea abies EO | 11.2% | [20] |
| Artemisia sieversiana aerial parts EO | 7.9% | [21] |
| Satureja aucheri var. canescens EO | 6.5% | [22] |
| Unspecified plant EO (concentration) | 6.32% | [18] |
Natural Occurrence and Quantitative Distribution of Borneol in Plant Essential Oils
Borneol-type monoterpenoids—including the alcohol borneol and its ester bornyl acetate—are widely distributed across diverse plant species and their essential oils (EOs). Borneol serves as a biosynthetic precursor to camphor via hydroxyl group oxidation [1], and its presence and concentration vary by plant species, tissue type, geographical origin, extraction method, and environmental factors (e.g., adelgid infestation, tree maturity [23]; melatonin treatment and mycorrhizal symbiosis [24]; pulsed electric field (PEF) treatment [25]). It is often classified as a minor, major, or dominant constituent in EOs, with some studies noting its occurrence only in specific cultivars (e.g., blueberry ‘Premier’ and ‘Legacy’ [26]) or plant parts (e.g., rhizomes [12], cones [27], or root oil [28]). Borneol is also associated with distinct chemotypes (e.g., cineole-thujone-borneol in Sinai plants, cineole-camphor-borneol in Israeli plants [3]) and is detected in specialized extracts like hydrolates [29] and honey [30].
Borneol Content in Plant Essential Oils and Extracts
| Plant Species/Extract Type | Borneol Content/Notes | Citation(s) |
|---|---|---|
| Unspecified plant (flower samples) | Detected alongside α-pinene, β-pinene, limonene | [31] |
| Unspecified plant (cone-like fruits EO) | 4.6% (borneol); 7.8% (bornyl acetate) | [32] |
| Artemisia absinthium EO | Present among mono- and sesquiterpene components (including 1,8-cineole, camphor, myrcene) | [33] |
| Lavandula angustifolia EO | 8.29% (dominant constituent) | [34] |
| Lavender EOs (various) | 1–17% (bicyclic monoterpene component) | [6] |
| Calceolaria laevipes EO | 4.07 ± 0.43% (volatile fraction); 3.21 ± 0.32 μg/g fresh weight (most abundant monoterpene) | [35] |
| Mentha suaveolens EOs (Moroccan populations) | Part of terpenic alcohol fraction (65–90% of total EO) | [36] |
| Thyme EO | 3.4% | [37] |
| Thymus serpyllum EO (2-HD) | 13.5% | [38] |
| White thyme oil | 32% | [39] |
| Thymus daenensis and T. vulgaris EOs | Major component | [40] |
| Plectranthus amboinicus EO | Minor compound | [41] |
| Eucalyptus EOs (Spain) | High concentration (unlike Morocco/Tunisia EOs, rich in 1,8-cineole) | [1] |
| Achillea distans, A. lingulata, A. millefolium EOs | Most abundant compound | [42] |
| Unspecified plant S (EO) | 23.7% (major compound in oxygenated monoterpene class, 44.5% of total oil) | [43] |
| Unspecified EO | One of eight compounds with normal distribution | [44] |
| Ginger EO (fresh vs. dried) | Fresh has higher concentration than dried | [45] |
| Unspecified EO | 0.32% (main oxygenated monoterpene component) | [46] |
| Unspecified EO | 13.6% (major constituent; oxygenated monoterpenes 68.2% of total) | [7] |
| Achillea clypeolata EO (Ivaylovgrad, Bulgaria) | 8.9% | [47] |
| Achillea clypeolata EO (Dobrostan, Bulgaria) | 22.6% | [47] |
| Rosemary EO | 3.81% | [48] |
| Rosemary leaf EO | 17.9% (main oxygenated monoterpene) | [49] |
| Moldavian balm EO (melatonin + mycorrhizal symbiosis) | 10.16% (peak concentration) | [24] |
| Unspecified EO (monoterpene fraction) | 2.66% | [50] |
| Unspecified EO | 14.99% (main compound) | [8] |
| Sinai plant EOs | Cineole-thujone-borneol chemotype | [3] |
| Israeli EO | Cineole-camphor-borneol chemotype | [3] |
| Blueberry cultivars | Present only in ‘Premier’ and ‘Legacy’ | [26] |
| Hemlock twig volatiles | Levels influenced by adelgid infestation and tree maturity | [23] |
| Lomatium scaberrima EO | ~2% | [51] |
| Unspecified plant (volatile oil) | Among 43 oxygenated monoterpenoids | [52] |
| Unspecified plant (rhizome extract) | 3.9% (major monoterpene); almost exclusive to rhizomes (with camphene, α-gurjunene) | [12] |
| Origanum EO (OEO) | 1.46 ± 0.07% | [13] |
| Artemisia alba EO (tincture) | Representative compound (with artemisia alcohol, camphor, davana ether) | [53] |
| Hesperozygis crenata leaf EO | 1.74–3.38% (annual average 2.34 ± 0.48%); varies with collection time/location | [54] |
| Unspecified plant (seed origins/seedlings) | Incidence very small | [55] |
| Thymus cariensis EO | 6.04% (major compound) | [56] |
| Thymus cilicicus EO | 16.97% (most abundant compound) | [56] |
| Unspecified sample (FIV) | 0.2% (highest proportion; with geranyl acetate) | [57] |
| Unspecified EO (GC-MS) | Detected alongside 1,8-cineole, bornyl acetate | [58] |
| Unspecified plant (leaf EO) | Appreciable amounts; not detected in Nigerian Taxodium distichum oil | [59] |
| Chamaecyparis obtusa f. formosana wood oil | 16% (major oxygenated monoterpene) | [60] |
| Salvia macrosiphonia EO | High in individual 1; traces in others | [61] |
| Origanum majorana EO | Main terpenoid component | [62] |
| Rosemary varieties | Negative correlation with whitefly preferences (’M’ group) | [63] |
| Thyme oil sample | 0.2% (lesser amount) | [64] |
| Unspecified plant (aerial parts, apolar fraction HS-SPME) | 6.1% (representative compound) | [65] |
| Eucalyptus citriodora oil | 2.48% | [66] |
| Salvia virgata EO | Up to 19.5% | [67] |
| Two unspecified samples | Minor compound (>1%; with α-thujene, α-pinene, trans-caryophyllene) | [68] |
| Field-grown lavender (Ellagance Purple) | 9% (dominant compound) | [69] |
| Field-grown lavender (Blue River) | 13% (dominant compound) | [69] |
| Field-grown lavender (Munstead) | 9% (dominant compound) | [69] |
| In vitro-propagated lavender (Ellagance Purple) | 32% (more abundant) | [69] |
| In vitro-propagated lavender (Blue River) | 26% (more abundant) | [69] |
| In vitro-propagated lavender (Munstead) | 13% (more abundant) | [69] |
| Unspecified AEO | 5.09% | [70] |
| Unspecified EO | 13.5% (major component; with eucalyptol 28.7%, camphor 16.7%) | [9] |
| Cinnamomum burmannii (hydrolysed) | 3.21 μg PI equiv./mL | [71] |
| Cinnamomum burmannii (native) | 2.42 μg PI equiv./mL | [71] |
| Cinnamomum verum | 0.15 μg PI equiv./mL (lower than C. burmannii) | [71] |
| Primorsky Ridge/Olkhon Island plant EOs | Main component (with 1,8-cineole, camphor, terpineol-4) | [72] |
| Thymus eriocalyx EO | 5.7% | [73] |
| Satureja montana EO | 3.1% | [74] |
| Unspecified volatile extract | 2.67% (dominated by R-pinene 23.73%, thymol methyl ether 17.32%) | [14] |
| Unspecified plant (flower EO) | 44.8% (major constituent) | [10] |
| Unspecified plant (aerial parts EO) | 31.2% (major constituent) | [10] |
| Dombeya buettneri stem oil | 4.2% | [15] |
| Rugosa rose primary hydrolate | Detected alongside other monoterpene alcohols | [75] |
| Salvia dolomitica EO | 5.86% | [16] |
| Tanacetum vulgare (flower extracts) | Major volatile compound | [19] |
| Tanacetum vulgare (leaf extracts) | Appreciable amounts | [19] |
| Picea abies EO | 11.2% (representative oxygenated monoterpene) | [20] |
| Juniperus x pfitzeriana, J. chinensis, P. abies EOs | Bornyl acetate (main component, (-)-enantiomer) | [20] |
| Unspecified EO | 2.3% (lower mean percentage) | [76] |
| Rosemary EO (common) | Main constituent (with camphene, α-pinene, 1,8-cineole) | [5] |
| Artemisia sieversiana aerial part EO | 7.9% (main component) | [21] |
| Vegetative profile (oxygenated monoterpenes 65.66%) | 6.32% | [18] |
| EO profile (oxygenated monoterpenes 70.42%) | 2.0–3.0% (relative abundance) | [18] |
| LI hydrolate | 24.4% (predominant component) | [29] |
| LO hydrolate | 21.8% (predominant component) | [29] |
| RO hydrolates (Serbia/Italy) | 10.1% in both | [29] |
| Unspecified plant (Chaharmahal and Bakhtiari population) | 16.13% (major component) | [77] |
| Abies nakaii EO | 6.82% (dominant monoterpene) | [78] |
| Eucalyptus citriodora (lemon eucalyptus) | Previously known constituent | [79] |
| Alpinia galanga | Slightly lower levels than A. calcarata | [80] |
| Unspecified plant (flowers) | 0.3% (minor component) | [81] |
| Unspecified plant (leaves) | 0.7% (minor component) | [81] |
| Satureja montana L. (SOLL) extracts | endo-borneol/l-borneol (principal volatile components; increased in PEF-treated extracts) | [25] |
| Artemisia subdigitata EO | 6.23% | [82] |
| Unspecified plant EO | One of six oxygenated monoterpenoids | [83] |
| Unspecified oil samples (FP) | 4.1% (third most important in oxygenated monoterpene fraction) | [84] |
| Unspecified oil samples (InV) | 4.6% (third most important in oxygenated monoterpene fraction) | [84] |
| Unspecified oil samples (MP) | 4.8% (third most important in oxygenated monoterpene fraction) | [84] |
| Unspecified plant (post-flowering EO) | Among monoterpene alcohols | [85] |
| P. artemisioides EO | 2.4% (borneol); 2% (bornyl acetate) | [86] |
| Unspecified EO | 1.9% (with other terpenes >1%) | [87] |
| Honey (bornane skeleton monoterpenes) | 5.0–10.9% | [30] |
| Unspecified oil samples (Pi) | 22.7% (major component) | [88] |
| Unspecified oil samples (Pr) | 24.8% (major component) | [88] |
| Rosemary EO | Up to 23.7% | [89] |
| Unspecified plant (cone extract) | Only detected in cones | [27] |
| P. incanum (aerial parts, South Carolina wild) | 8.2% of EO | [90] |
| Rosmarinus officinalis L. EO | 1.999% | [91] |
| Lavender, S. leriifolia, valerian EOs | Constituent | [92] |
| Unspecified EO | 4.66% | [93] |
| Unspecified plant (leaf EO) | 1.12% | [94] |
| Unspecified plant (fruit oil) | 2.74% (major oxygenated monoterpene) | [95] |
| S. macrochlamys EO | 13% (major constituent) | [96] |
| Hesperozygis crenata root oil (HCCRO) | Unique constituent (with p-cymene, α-terpineol; absent from aerial part oil [HCCAO]) | [28] |
| Lavender EO (SHSD) | 10.4% (main component) | [97] |
| Lavender EO (SHSDACD) | 10.4% (main component) | [97] |
| Rosemary EO (SHSD) | 3.7% | [97] |
| Rosemary EO (SHSDACD) | 5.2% | [97] |
| Coriander EO | 0.03–2.6% (overall EO content; with limonene, α-pinene) | [98] |
Variability of Borneol Content in Plant Species Across Geographic and Environmental Factors
Borneol, a bicyclic oxygenated monoterpene, is biosynthesized from camphor via hydroxyl group oxidation[1] and occurs as a minor or major component in the essential oils (EOs) or volatile profiles of diverse plant species across multiple genera. Its presence and concentration are influenced by geographic origin, environmental factors, storage conditions, extraction methods, and temporal variability.
Borneol Content in Plant Essential Oils and Volatile Profiles
| Plant Species | Borneol Content Range/Value | Citation(s) |
|---|---|---|
| Plectranthus amboinicus EO | Minor constituent | [41] |
| Ginger EO | Small amount | [45] |
| Artemisia clypeolata (Bulgarian Dobrostan) | Up to 22.6% | [47] |
| Inula graveolens EO | 3.7–41.9% | [99] |
| Rosmarinus officinalis (rosemary) EO | 17.9% (some samples) | [49] |
| Lavandula angustifolia EO | 1–17% | [6] |
| Dracocephalum moldavica (Moldavian balm) EO | Present | [24] |
| Tsuga spp. (hemlock) twig volatiles | Present | [23] |
| Hypericum crenata leaf EO | 1.74–3.38% | [54] |
| Salvia yangii in vitro shoot extracts | Present | [100] |
| Thymus eriocalyx EO | 5.7% | [73] |
| Plants of Primorsky Ridge and Olkhon Island EO | Present | [72] |
| Rosa rugosa (rugosa rose) primary hydrolate | Detected | [75] |
| Clinopodium distans EO | Present | [101] |
| Unspecified species (monoterpenes: 1,8-cineole, camphor) | Present | [102] |
| Satyrium macrosiphonia EO | Present | [103] |
| Houttuynia cordata volatile profile | Present | [104] |
Geographic origin significantly impacts borneol content: Rosmarinus officinalis EOs from Spain have higher concentrations than those from Morocco, Tunisia, or France[1]; A. clypeolata from Serbian Ozren and Rtanj has lower levels than Bulgarian Dobrostan samples[47]; a cineole-camphor-borneol chemotype of an unspecified species was observed in Israel[3]; and Sat. macrosiphonia samples from Poldokhtar (Lorestan Province, Southwest Iran) contain 16.60% borneol compared to 8.20% in Kabirkooh (Ilam Province, Southwest Iran)[103]. In an unspecified species, total monoterpene concentrations (including borneol) were higher at Camas than Cedar Gulch, with the largest differences in summer[102].
Environmental factors also modulate borneol levels: in Moldavian balm, concurrent melatonin treatment and mycorrhizal symbiosis with Glomus intraradices increased borneol by ~37% under drought stress[24]; in rosemary, 100 mM NaCl slightly decreased borneol while FeCl₃ increased it[49]; mature hemlock trees had significantly higher borneol than saplings in June and November[23]; S. yangii in vitro shoots had the highest borneol at 130 μmol m⁻² s⁻¹ light intensity[100]; an unspecified species showed a positive correlation between borneol and altitude (0.69 < r < 0.79, p < .05)[105]; and lower canopy RGB spectral control lighting (SCL) increased borneol compared to control SCL[106]. Water deficit stress increased borneol at 30% field capacity (FC) in an unspecified species, though GABA application at 30% FC reduced it[107]; fungal infection increased borneol in an unspecified species[108]; and Pseudomonas fluorescens inoculation decreased borneol in H. cordata seedlings by 54%[104].
Storage and extraction methods affect borneol content: C. distans herb stored under shade or field conditions saw borneol increase from 0.8% to 2.3%[101], and microwave-assisted hydrodistillation (MAHD) extracted more borneol from Sat. macrosiphonia than other methods[103]. Temporal variability is evident: I. graveolens borneol decreased from 32.5% to 16.8% between late August and late October[99]; H. crenata concentrations varied from 1.74% (November 2021, February 2022) to 3.38% (May 2022)[54]; and an unspecified species had higher quality patches (monoterpene percentage by DW < 0.92%) increase from 28% in summer to 98% in winter[102].
Chemical Characteristics of Borneol Derivatives and Their Co-Occurrence in Plant Extracts
Borneol is a bicyclic oxygenated monoterpene that co-occurs with related compounds—including bornyl acetate, camphor, 1,8-cineole, α-pinene, and camphene—in essential oils across diverse plant species and regions, with notable variations in content and chemotype [1][4][43][44][7][6][48][99][8][3][49][12][13][54][109][64][65][67][68][69][70][9][14][10][15][16][20]. Biosynthetically, camphor—another common co-occurring oxygenated monoterpene—is derived from borneol via hydroxyl group oxidation [1].
Borneol Content and Co-Occurring Compounds in Plant Essential Oils and Extracts
| Plant Source | Borneol Content | Co-Occurring Compounds | Citations |
|---|---|---|---|
| Spanish rosemary (Rosmarinus officinalis) oil | High concentration (contextual) | Camphor | [1][48] |
| Moroccan/Tunisian rosemary oil | Contextual (lower than Spanish) | 1,8-cineole (rich) | [1][48] |
| Lavandula angustifolia oil (general) | 1–17% | Bicyclic oxygenated monoterpenes | [6] |
| Lavandula angustifolia (field-grown varieties: Ellagance Purple, Blue River, Munstead) | 9–13% | — | [69] |
| Lavandula angustifolia (in vitro-propagated varieties) | 13–32% | — | [69] |
| Unspecified plant (S) essential oil | 23.7% (primary compound) | Bornyl acetate (6.5%) | [43] |
| Inula graveolens oil (seasonal variation) | 3.7–41.9% (decreases from 32.5% to 16.8% Aug–Oct) | Bornyl acetate (43.1–73.1%, increases from 38.9% to 49.0% Aug–Oct) | [99] |
| Israel sample (E18) | High (cineole-camphor-borneol chemotype) | Camphor (high), 1,8-cineole, thujone (low) | [3] |
| Unspecified plant (flowers) | 44.8% (major constituent) | Camphor, camphene, 1,8-cineole, germacrene D | [10] |
| Unspecified plant (aerial parts) | 31.2% (major constituent) | Camphor, camphene, 1,8-cineole, germacrene D | [10] |
| Rosemary leaves | 17.9% | — | [49] |
| Haplophyllum crenata leaves | 1.74–3.38% | — | [54] |
| Origanum essential oil | 1.46% | — | [13] |
| Unspecified plant rhizome extracts | 3.9% | — | [12] |
| Salvia virgata | Up to 19.5% | — | [67] |
| Thyme oil | 0.2% | — | [64] |
| Unspecified plant (apolar aerial fraction) | 6.1% | — | [65] |
| Eucalyptus citriodora oil | 2.48% | — | [66] |
| Two unspecified plant samples | >1% | — | [68] |
| AEO essential oil | 5.09% | — | [70] |
| Unspecified essential oil | 13.5% | — | [9] |
| Hydrolysed Cinnamomum burmannii | 3.21 μg PI equiv./mL | — | [71] |
| Native Cinnamomum burmannii | 2.42 μg PI equiv./mL | — | [71] |
| Volatile extract | 2.67% | — | [14] |
| Dombeya buettneri stem oil | 4.2% | — | [15] |
| Salvia dolomitica essential oil | 4.41% | — | [16] |
| Picea abies essential oil | 11.2% | Bornyl acetate (15.6%, main component) | [20] |
| Unspecified plant (vegetative essential oil) | 6.32% | 1,8-cineole (42.17%), p-cymene (14.05%), caryophyllene oxide (4.41%) | [18] |
| Unspecified plant (essential oil) | 2.0–3.0% | Linalool (27.70%), linalyl acetate (17.99%), 4-terpineol (5.30%) | [18] |
| Turnjujube (free form) | 9.49 μg·L⁻¹ (detected after 21 days storage) | — | [110] |
| Turnjujube (bound form) | 1636.44–4177.34 μg·L⁻¹ (all storage stages) | — | [110] |
| Unspecified plant population (Chemotype VI: OV10–OV17) | Traces–15.48% | Linalool (0.59–34.09%), germacrene D (3.03–26.30%), α-terpineol (1.07–20.12%), β-caryophyllene (1.01–14.58%) | [111] |
| Lavandula x intermedia | Characteristic component | Camphor, 1,8-cineol, linalool | [112] |
| Liberty Reach formulation | Component | 13 marijuana terpenes (α-pinene, β-myrcene, limonene, linalool, terpineol, β-caryophyllene, etc.) | [113] |
Bornyl acetate, a key derivative of borneol, co-occurs in several species: it is a medium-to-high amount component (0.5–10%) in an unspecified plant’s essential oil [109], the main component in P. abies, Juniperus x pfitzeriana, and J. chinensis essential oils (15.6% in P. abies) [20], and a main constituent (18.10%) in Salvia somalensis essential oil [16]. Borneol also appears in broader phytochemical profiles: B. balsamifera includes it alongside terpenoids, fatty acids, phenols, alcohols, aldehydes, ethers, ketones, pyridines, furans, and alkanes [114], and it is detected in all L. angustifolia leaf samples [112].
Structural Classification and Stereochemical Characteristics of Borneol and Its Derivatives
Structural Classification and Biosynthetic Pathways of Borneol-Type Monoterpenoids
Borneol is a bicyclic monoterpenoid with the chemical structure 1,7,7-trimethyl-endo-bicyclo [2.2.1] heptan-2-ol [115][116]. Classified as an oxygenated monoterpene, it is grouped with other bicyclic monoterpenes (e.g., thujene, α-pinene, camphene, Δ3-carene, bornyl acetate) that share the ability to undergo profound structural changes [117]. Borneol exists as a stereoisomer; the endo-isomer is a bioconversion product of both α-pinene and β-pinene [118], and L-borneol exhibits superior bacterial adhesion inhibition due to its C2 chiral center [119]. Clinically used Chinese medicines containing borneol include L-Borneolum (‘Ai Pian’), Borneolum (‘Tian Ran Bing Pian’), and synthetic borneol (‘He Cheng Bing Pian’), each with distinct stereochemical configurations [119]. Borneol (endo-isomer) and its exo-isomer isoborneol show similar abundance trends during the growth cycle of C. haritha, with isoborneol levels nearly double those of borneol [120]; isoborneol has also been identified in essential oils at levels up to 8.1% [121].
Key Chemical and Physical Properties of Borneol
| Property | Value | Reference(s) |
|---|---|---|
| Chemical structure | 1,7,7-trimethyl-endo-bicyclo [2.2.1] heptan-2-ol | [115][116] |
| Synonyms | Bicyclo(2.2.1)heptan-2-ol,1,7,7-trimethyl-endo-; Borneocamphor; dl-borneol; Bornyl alcohol; 2-Camphanol; D-Camphanol; Camphol; 2-Hydroxycamphane; 1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol | [116] |
| Molecular formula | C₁₀H₁₈O | [116] |
| Molecular weight | 154.25 | [116] |
| Boiling point | 212 °C | [116] |
| Water solubility (25 °C, calculated) | 1186 mg/l | [116] |
| Vapor pressure (20 °C, calculated) | 0.3 mmHg | [116] |
| Log Kow (calculated) | 2.85 | [116] |
Biosynthetically, borneol is part of plant terpenoid pathways, which rely on the cytoplasmic mevalonate (MVA) and plastidial 2-C-methyl-D-erythritol 4-phosphate (MEP) pathways—both producing isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) [4]. In C. burmanni, terpenoid biosynthesis-related genes include those encoding enzymes for carbon skeleton synthesis (Ko00900), monoterpenoid synthesis (Ko00902), and other terpenoid pathways [122]. Borneol is a bioconversion product of α-pinene [118] and shares a biosynthetic pathway with camphor; camphor is formed via oxidation of borneol’s hydroxyl group, making borneol a precursor to camphor [1][120]. The putative camphor biosynthesis pathway from IPP/DMAPP involves four enzymes: geranyl diphosphate synthase (gpps), bornyl diphosphate synthase (bpps), bornyl diphosphate diphosphatase (bppd), and borneol dehydrogenase (bdh) [123]. Tissue-specific analysis in O. gratissimum showed roots accumulated 57% borneol, while aerial tissues had high camphor levels (with no detectable borneol, likely due to high bdh expression driving rapid conversion to camphor) [123]. Roots also contained comparable borneol and camphor levels, suggesting low bdh expression [123]. Differential expression of gpps (the entry enzyme for monoterpene flux) and bdh regulates camphor partitioning across tissues [123].
Borneol Content in Plant Essential Oils and Substances
| Source | Borneol Content | Reference(s) |
|---|---|---|
| A. sieversiana aerial parts essential oil | 7.9% | [21] |
| C. libanotis essential oil | 6.3% | [124] |
| C. villosus essential oil | 2.5% | [124] |
| Rosemary hydrosol headspace | 3.7% | [125] |
| T. capitellatus essential oil | 10.1% (major oxygenated monoterpene) | [126] |
| Lahaul-Spiti essential oil | 10.94% (major constituent) | [127] |
| Rosmarinus leaves essential oil | 3.78% (minor component) | [128] |
| Unspecified essential oil sample | 4.0% (minor component) | [129] |
| Plant-based substance (with 1,8-cineole, terpinen-4-ol, (−)-α-bisabolol) | 0.19% (trace) | [130] |
Borneol is a main monoterpene in Rosmarinus [131] and can be found as an ether in nonpolar extracts [132]. It is a precursor to bornyl acetate, an oxygenated monoterpene with highly variable abundance (0.4% to 18.5%) across plant specimens [133]. In turnjujube, borneol occurs in both free and bound aroma forms: free borneol is detected at 9.49 μg·L⁻¹ after 21 days of storage, while bound borneol (1636.44–4177.34 μg·L⁻¹) exceeds all other bound oxygenated monoterpenes [110]. Borneol is also a potential precursor of mixed fatty acid esters in the ester fraction of the yellow coat [134] and is an oxygenated monoterpene component of conifer essential oils, alongside bornyl acetate and other monoterpenes [135].
Geographic Variation and Chemotype-Specific Distribution of Borneol
Borneol is a bicyclic monoterpenoid [1][117][2], with a structural framework that enables profound modifications—such as conversion to other bicyclic monoterpenes (e.g., α-pinene, camphene, Δ3-carene, bornyl acetate) in the presence of organic acids [117]. Camphor, another oxygenated monoterpene, is biosynthesized from borneol via hydroxyl group oxidation [1][2]. Geographic and species-specific variation in borneol content is widely documented, with environmental factors, chemotype, and extraction methods also influencing its presence and concentration, as summarized below.
Borneol Content Variation Across Plant Species, Regions, and Conditions
| Plant Species | Context/Region | Borneol Content/Key Finding |
|---|---|---|
| Rosmarinus officinalis (rosemary) | Biological fertilizer application | Increased content [136] |
| Origanum onites | PGPR inoculation | Altered biosynthesis [136] |
| Lavandula angustifolia (lavender) | Different lavender essential oils | 1% to 17% (major oxygenated bicyclic monoterpene) [6] |
| Artemisia frigida | Buryatian flora | Dominant monoterpenoid component [137] |
| Salvia macrosiphonia | Poldokhtar, Lorestan Province (Iran) | 16.60% [103] |
| Salvia macrosiphonia | Kabirkooh, Ilam Province (Iran) | 8.20% [103] |
| Cinnamomum burmannii (high D-borneol chemotype) | Chemotype comparison | 66.21% D-borneol (15 detected compounds; ~7x higher than low chemotype) [122] |
| Cinnamomum burmannii (low D-borneol chemotype) | Chemotype comparison | 55.99% D-borneol (13 detected compounds) [122] |
| Cinnamomum burmannii vs. C. verum | Hydrolysed and native essential oils | Higher borneol amounts in C. burmannii [71] |
| Salvia macrosiphonia | Extraction method comparison | Microwave-assisted hydrodistillation (MAHD) extracts more borneol than other methods [103] |
Hierarchical cluster analysis of essential oil samples from Croatia’s Dalmatian region identified Cluster C, characterized by the compound order: camphor > α-thujone > 1,8-cineole > camphene ≈ borneol [138].
Stereochemical Characteristics and Enantiomeric Analysis of Borneol
Borneol is a bicyclic monoterpenoid with clinical applications in Chinese medicine, where three main types are recognized: L-Borneolum (‘Ai Pian’), Borneolum (‘Tian Ran Bing Pian’), and synthetic borneol, each differing in stereochemical configurations [119]. The stereochemical characteristics of borneol extend to its enantiomeric distribution across plant species and essential oils, with specific enantiomeric profiles and separation methods reported in various studies. The stereochemical configuration of borneol also influences its biological activity; for example, L-borneol exhibits better inhibition of bacterial adhesion due to its C2 chiral centre [119].
Borneol Enantiomeric Profiles and Separation Methods Across Plant Species and Essential Oils
| Source | Enantiomeric Profile | Key Finding | Citation |
|---|---|---|---|
| Portuguese-grown plant essential oils | (–)-enantiomer | Most abundant enantiomer | [139] |
| 69 Salvia species accessions | (+)-borneol | Identified as the present enantiomer | [140] |
| Lavender essential oil | 76% enantiomeric excess (R enantiomer) | Potential chiral marker for oil authenticity | [141] |
| Chromatographic separation | Overlap on Rt-βDEXse column; well-separated on β-DEX 120 column (S then R elution) | Method for enantiomeric separation | [141] |
| Chamaecyparis verticillata essential oil | Scalemic mixture (57% (1S,2R,4S)-(−); 43% (1R,2S,4R)-(+)) | Differs from Rosmarinus officinalis ratio | [142] |
| Rosmarinus officinalis | 90:10 enantiomeric ratio | Reference ratio for comparison | [142] |
| Eucalyptus grandis essential oil | Part of eight enantiomeric monoterpene pairs | Enantiomeric excess determined alongside α-pinene and linalool | [143] |
Chemical Composition and Derivative Profiles of Borneol-Type Monoterpenoids in Plant Essential Oils
Borneol is a bicyclic, camphane-type oxygenated monoterpenoid (C10H18O, molecular weight 154.25) [103, 148] that occurs alongside derivatives like bornyl acetate and camphor in essential oils (EOs) of diverse plant species [29, 49]. Biosynthetically, camphor forms via oxidation of borneol’s hydroxyl group [1]. Its physical properties include a boiling point of 212 °C, water solubility of 1186 mg/l at 25 °C, and a log Kow of 2.85 [116]. Stereochemically, the (–)-enantiomer dominates in Thymus mastichina EO [139], while bornyl acetate (a borneol derivative) primarily exists as the (-)-enantiomer (99.65–100%) in EOs of J. x pfitzeriana, J. chinensis, and P. abies [20].
Borneol’s presence and concentration in EOs vary by plant species, part, extraction method, and storage conditions. It is a common constituent in Adenosma species [144], a key aroma compound in yuzu citrus oil [145], and a component of conifer EOs (classified as an oxygenated monoterpene alongside bornyl acetate) [135]. In turnjujube, it exists in free (9.49 μg·L−1 after 21 days of storage) and bound (1636.44–4177.34 μg·L−1) forms [110]. Extraction method influences yield: microwave-assisted hydrodistillation (MAHD) extracts more borneol from Satureja macrosiphonia than other methods [103], and steam distillation (SD) yields higher borneol and bornyl acetate content in Thymus algeriensis than hydrodistillation (HD) [146]. Borneol levels also decrease during flowering in an unspecified plant [147].
Borneol is often associated with other monoterpenoids in EOs (e.g., camphor, 1,8-cineole, thymol) [103, 107, 109, 164, 167, 168, 172, 177, 180, 185, 190, 191] and is included in hierarchical cluster analyses (e.g., clustered with camphor, α-thujone, 1,8-cineole, and camphene in Dalmatian EO samples) [138] and chemotype classifications (e.g., chemotypes defined by germacrene-D + borneol + bornyl acetate, or borneol + camphor) [2]. In chromatographic analysis, its elution order reflects its boiling point: less retained than menthol but more than 1,8-cineole [148]. Solid-state behavior includes forming a continuous solid solution with camphor in an orientationally disordered phase (SI) [149].
Borneol’s biological roles include positive association with mountain pine beetle (MPB) response but negative impacts on fungal growth, with higher concentrations in plant families least suitable to G. clavigera [150]. Its presence in EOs can stem from monoterpene hydrocarbon degradation [151], and it is a significant component in most of certain plant extracts [151]. Borneol can be isolated using solvent systems like HEMWat (5:2:5:2 v/v) and n-hexane/acetonitrile/MTBE (1:1:0.1 v/v) [152], while bornyl acetate’s structure can be confirmed via NMR spectroscopy [133].
Borneol Concentrations in Plant Essential Oils and Extracts
| Plant Source | Borneol Concentration | Citations |
|---|---|---|
| Unspecified cone-like fruit oil | 4.6% | [32] |
| Thymus algeriensis EOs | 11.16–17.13% | [146] |
| Artemisia absinthium leaf EO (Iran) | 25.99% | [153] |
| Lavender EOs | 1–17% | [6] |
| Wild oregano EO | Above 1% | [154] |
| Origanum vulgare EO | 1.46% | [13] |
| Thymus vulgaris EO | 2.22% | [152] |
| L. angustifolia EO | 7.39% | [155] |
| Unspecified plant EO | 32.97% | [156] |
| Dombeya buettneri stem EO | 4.2% | [15] |
| Salvia dolomitica EO | 4.41% | [16] |
| P. abies EO | 11.2% | [20] |
| A. sieversiana aerial parts EO | 7.9% | [21] |
| Unspecified plant EO | 6.3% | [157] |
| Oe and OeH EOs | 6.2–6.3% | [158] |
| Volatile extract | 2.67% | [14] |
| Unspecified plant flower EOs | Up to 44.8% | [10] |
| Unspecified plant aerial parts EOs | 31.2% | [10] |
| Unspecified plant EO | 1.97 ± 0.01% | [17] |
| Rosemary leaf EO | 3.78% | [128] |
| Satureja macrosiphonia EO (Poldokhtar, Iran) | 16.60% | [103] |
| Satureja macrosiphonia EO (Kabirkooh, Iran) | 8.20% | [103] |
| Unspecified plant EO | 11.9% | [159] |
| D. aromática EO | 1.0% | [160] |
Extraction, Quantification, and Analytical Methods for Borneol-Type Monoterpenoids
Borneol is a bicyclic oxygenated monoterpene that co-occurs with related monoterpenoids (e.g., camphor, camphene, 1,8-cineol, bornyl acetate) in essential oils from diverse plant species, including Thymus algeriensis[146], plants from the Republic of Buryatia[161], rosemary[162][48][131][128][97], Boswellia serrata[163], and lavender[6][141][164][97]. It is also present in other sources, such as H. crenata[54], T. cariensis[56], T. cilicicus[56], A. frigida[137], Oe and OeH essential oils[158], lavender varieties[69], AEO[70], Thymus vulgaris[152], and minor amounts in various samples[157][57][68][165][76]. Additionally, borneol is found in petroleum ether fractions[166], florence water[166], plant extracts in Haihun ink[167], lavandin[164], Eucalyptus grandis[143], Sat. macrosiphonia[103], and certain regional samples[168]. It can also be produced via biotransformation (e.g., α-pinene by P. brumalis[169]) and is present in earth oil, ethanolic extract[170], seed monoterpenoids[133], and as an enantiomeric mixture in several species[141][142][143].
Borneol content varies by plant matrix, extraction method, geographic origin, collection time, and habitat. For example, Thymus algeriensis shows borneol concentrations of 11.16–17.13% across aerial parts and leaves[146], while rosemary products yield 18.79% (SC-CO₂), 8.52% (HD), and 3.75% (OM)[162]. Lavender essential oils contain 1–17% borneol[6], with in vitro-grown varieties (13–32%) having higher levels than field-grown ones (9–13%)[69]. Borneol levels also differ by geographic origin (e.g., TCMs[171][172]) and habitat (e.g., A. frigida[137]), and seasonal variations are observed in H. crenata[54].
Extraction method efficiency for borneol depends on the plant matrix: steam distillation (SD) outperforms HD for Thymus algeriensis leaves[146], while microwave-assisted hydrodistillation (MAHD) is more effective for certain materials[103]. Comparable results are obtained via SD and MAE–HS-SPME[171]. For quantification, GC and GC-MS are common, using standards from Acros[173], Sigma Aldrich[6][152], or Fluka AG[174]. Headspace GC-FID has been used for sage-grouse gut contents[175], with calibration curves showing strong linearity (e.g., 0.05–10 mg g⁻¹, R²=0.999[171]; Y=24.03X-0.18, R²=0.9993[172]). Precision is supported by RSD values of 10.8%[171] and recovery rates of 94%[171]. Enantioselective chiral analysis has been applied to Salvia spp. and rosemary varieties[140], with separation on β-DEX 120 columns[141]. Lavender shows a 76% enantiomeric excess for the R enantiomer[141], while C. verticillata has a 57:43 ratio of (−) to (+) borneol[142], differing from R. officinalis[142]. NIR spectroscopy with PLS regression models can predict borneol content in lavandin with REP of 5–10%[164]. Pure borneol (98–100% purity) has been isolated using solvent systems[152], and deuterated borneol can be synthesized and quantified via GC-FID[142].
Borneol Concentrations in Plant Sources and Extraction Methods
| Plant Source/Matrix | Borneol Concentration/Content | Reference(s) |
|---|---|---|
| Thymus algeriensis (aerial parts/leaves) | 11.16%–17.13% (lower than camphor) | [146] |
| Rosemary (SC-CO₂ extraction) | 18.79% | [162] |
| Rosemary (hydrodistillation, HD) | 8.52% | [162] |
| Rosemary (organic solvent maceration, OM) | 3.75% | [162] |
| Lavender essential oils | 1–17% | [6] |
| Boswellia serrata bark oil | 1.78% | [163] |
| H. crenata leaf essential oils | 1.74%–3.38% (average: 2.34% ± 0.48%) | [54] |
| T. cariensis essential oil | 6.04% | [56] |
| T. cilicicus essential oil | 16.97% | [56] |
| A. frigida (Buryatian flora) | Dominant monoterpenoid | [137] |
| Oe essential oil | 6.2% (0.9 ± 0.60 mg/100 mL) | [158] |
| OeH essential oil | 6.3% (0.7 ± 0.35 mg/100 mL) | [158] |
| Lavender (field-grown varieties: Ellagance Purple, Blue River, Munstead) | 9%–13% | [69] |
| Lavender (in vitro-grown) | 13%–32% | [69] |
| AEO | 5.09% | [70] |
| Thymus vulgaris essential oil | 2.22% | [152] |
| Sample 1 | 2.3% | [76] |
| FIV | 0.2% | [57] |
| Source 1 | 6.3% | [157] |
| Monoterpene-rich fraction | 1.5% | [165] |
| Some samples | >1% | [68] |
| Lavandin essential oils | 3.80% | [164] |
| Eucalyptus grandis essential oil | 2.03% | [143] |
| Rosemary leaf essential oil | 3.78% | [128] |
| Rosemary volatile oil (SHSD) | 3.7% | [97] |
| Rosemary volatile oil (SHSDACD) | 5.2% | [97] |
| Sat. macrosiphonia (Poldokhtar) | 16.60% | [103] |
| Sat. macrosiphonia (Kabirkooh) | 8.20% | [103] |
| Punta Balestreri sample | 2.5% | [168] |
| Tonara 1 sample | 8.3% | [168] |
| α-pinene biotransformation (P. brumalis, 5 days) | 8.59% | [169] |
| Earth oil/ethanolic extract | 1.24% each | [170] |
| Sample 2 | 4.66% | [93] |
| Seed monoterpenoids (certain woods) | Trace to 0.9% | [133] |
Chemical Reactivity, Biosynthesis, and Metabolic Transformations of Borneol-Type Monoterpenoids
Borneol, a bicyclic monoterpenoid, is biosynthesized from geranyl pyrophosphate (GPP) via bornyl diphosphate synthase (BPPS) catalysis to bornyl diphosphate, followed by dephosphorylation [176]. BPPS enzymes have been identified in S. officinalis, Lavandula angustifolia, Lippia dulcis, Amomum villosum, and Cinnamomum burmanni [176]. Terpene biosynthesis in plants, including borneol, proceeds through the mevalonate (MVA) and non-mevalonate (MEP/DOXP) pathways, with isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) as precursors [4]. In C. burmanni, nov_miR_111 and nov_miR_251 negatively correlate with borneol content, while nov_miR_377 positively correlates, with these miRNAs predicted to regulate MVA and MEP pathway genes [177]. Inoculation with plant growth-promoting rhizobacteria (PGPR) species—P. fluorescens, P. putida, B. subtilis, and P. polymyxa—significantly affects borneol biosynthesis in Origanum onites [136].
In O. gratissimum, the putative camphor biosynthesis pathway from IPP/DMAPP involves four steps catalyzed by geranyl diphosphate synthase (gpps), BPPS, bornyl diphosphate diphosphatase (bppd), and borneol dehydrogenase (bdh) [123]. Tissue-specific distribution analysis shows roots accumulate 57% borneol, while aerial tissues prefer camphor [123]. Borneol is undetectable in aerial tissues, likely due to high bdh expression driving rapid conversion to camphor; roots contain equal amounts of borneol and camphor, indicating low bdh expression [123].
Engineered microbial systems have been developed for borneol production, with codon-optimized BPPS genes (AvBPPS, LdBPPS, SoBPPS) and GmNES synthesized for E. coli; strains ENB2 and ENB3 produced borneol, with ENB2 yielding 4.26 mg/L [178]. Site mutation of LdBPPS (LdtBPPSS488T) increased production to 10.27 mg/L, and NudJ overexpression further raised it to 28.26 mg/L [178]. Optimized conditions led to strain ENB57 producing 38.46 mg/L, with two-phase fermentation boosting this to 87.20 mg/L [178].
Borneol exhibits distinct chemical and enzymatic reactivity. Chemically, it can be oxidized to camphor using hydrogen peroxide; the catalyst K5CoIIIW12O40 achieves ~90% conversion and >90% selectivity under optimized conditions (2:1 H2O2:borneol molar ratio, 383 K, 2.5 mol% catalyst, 120 min) [179]. 2a-Ethynyl-2b-hydroxybornane (4a) is prepared by ethynylating (+)-camphor with the lithium acetylide–ethylenediamine complex and ethyne in benzene [180], and host compounds 2a are synthesized from 4a via Eglinton coupling with copper(II) acetate in pyridine/methanol at 93% yield [180]. Enzymatically, Lavandula angustifolia LiBDH converts borneol to camphor using NAD⁺ (not NADP⁺) as a cofactor, with substrate specificity for borneol (Km = 53.6 ± 14.9 μM, Vmax = 3.97 × 10⁻¹ pmol s⁻¹) and optimal activity at pH 8.0 and 32 °C [181]. The ADH2 enzyme also acts on (+)- and (–)-borneol, though with lower activity than substrates like (–)-cis-carveol [182].
Borneol undergoes metabolic transformations via microbial and enzymatic bioconversion. It is a bioconversion product of α-pinene and β-pinene in bacterial systems [118]. Fungal species Collybia velutipes, Trametes hirsuta, and Ganoderma applanatum metabolize borneol through hydroxylation, oxidation, and hydrolysis, producing 5-exo-hydroxyborneol, 6-exo-hydroxyborneol (not from G. applanatum), and camphor [183]. Engineered P. putida KT2440 harboring a synthetic operon lacking camD (a 5-hydroxy group dehydrogenase) and camR (a repressor) biotransforms (–)-borneol into enantiomerically pure 5-exo-hydroxyborneol, purified to >98% via recrystallization [184]. Borneol is also a biosynthetic precursor of camphor, formed by hydroxyl group oxidation [1][120].
In metabolic studies, (–)-borneol pre-treatment in mice increases propofol’s maximum concentration (Cmax) and area under the curve (AUC) while lowering the volume of distribution at steady state (Vss) [185]. Borneol at 200 μM inhibits microsomal glucuronidation of propofol, though 0.5 mM (–)-borneol does not affect CYP-catalyzed metabolism [185]. Under petroleum stress, S. salsa preferentially fixes heavier ¹³C on borneol, enriching residual fractions with heavier isotopes [186]. Borneol complexes are stable, retaining 96–98% residual flavor content after 23 days [187].
Biological Activities and Functional Properties of Borneol-Type Monoterpenoids
Borneol is a bicyclic, oxygenated monoterpene alcohol [188][156] that adheres to Lipinski’s rule-of-five [189]. It occurs in varying concentrations across plant essential oils, hydrolates, and unidentified sources, as summarized below:
Borneol Concentrations in Plant-Derived Oils and Hydrolates
| Source | Borneol Concentration | Citation |
|---|---|---|
| YL-thyme oil | 6.50% | [190] |
| JB-thyme oil | 5.61% | [190] |
| QY-thyme oil | 1.52% | [190] |
| LD-thyme oil | 1.38% | [190] |
| Lavender essential oil (LEO) | 19.3% | [188] |
| Eucalyptus citriodora oil | 2.48% | [66] |
| Unidentified essential oil | 32.97% (major component) | [156] |
| LI hydrolate (Serbia) | 24.4% | [29] |
| LO hydrolate (Serbia) | 21.8% | [29] |
| RO hydrolate (Serbia) | 10.1% | [29] |
| S. macrochlamys essential oil | 13% | [96] |
Borneol exhibits diverse biological activities, including antioxidant, antimicrobial, antiadhesion, anti-proliferative, antiviral, and penetration-enhancing effects. It shows a statistically significant positive correlation with DPPH radical scavenging activity [190], contributes to the free radical scavenging ability of ginger essential oil (GEO)-incorporated films [191], and has strong antioxidant activity [156]. While borneol has weak antimicrobial activity alone [192][193][194][195][196][96], it interacts synergistically with other monoterpenes: combinations with γ-terpinene or α-terpinene show synergistic effects against Candida albicans and Candida tropicalis [192], and it enhances the antibacterial activity of terpinen-4-ol and limonene by penetrating bacterial membranes and impairing efflux pump activity [156]. Camphor and borneol were identified as important antimicrobial compounds [197], though commercial (+)- and (-)-borneol standards had insignificant activity against three Colletotrichum species [96].
Additional biological effects include reducing bacterial attachment and biofilm formation (antiadhesion) [156], 28.5% anti-proliferative inhibition against bacteria [195], moderate preventive inhibition of nitric oxide (NO) production [198], and reduced proliferation and collagen matrix deposition in primary mouse oral fibroblasts [29]. Borneol also has potent antiviral activity against orthopoxvirus and influenza A virus [66].
In penetration enhancement, borneol improves 5-fluorouracil (5-FU) permeation into the stratum corneum (SC) bilayer [199]: at 15% concentration, it forms ceramide (CER) head group channels oriented toward the bilayer center, and CER aggregates persist longer than menthol (especially at >10% concentration), prolonging transient pore opening [199]. For etoposide (VP16) absorption, 1.2% borneol increases transport by 2.8-fold, raises Cmax by 6.1 times, and boosts relative bioavailability by 2.2 times compared to VP16 alone [200]. For blood-brain barrier (BBB) modulation, borneol enhances uptake of P-glycoprotein (P-gp) substrates (e.g., Rhodamine 123) by brain microvascular endothelial cells (BMECs) in a dose-dependent manner, increases in vitro permeability of digoxin and verapamil across the BBB, and transiently downregulates mdr1a mRNA and P-gp protein expression in BMECs [201].
Borneol is a molecular target of the transient receptor potential melastatin 8 (TRPM8) channel: it induces intracellular Ca²⁺ increases in hTRPM8-expressing cells (EC₅₀ = 65 µM), with AMTB (a TRPM8 antagonist) completely inhibiting borneol-induced currents [202]. Stereoisomers exhibit varying activities: (1S)-(+)-borneol has moderate insecticidal activity (0.58–1.29 mg/cm²), while endo-(1R)-(-)-borneol is weaker (1.82–5.70 mg/cm²), with (1S)-(+)-borneol being 2.3-fold more toxic [203]. All stereoisomeric borneols and isoborneols strongly inhibit morphine-3-glucuronide (M-3-G) formation by rat liver microsomes (RLM) (IC₅₀ ≈ 20 µM for (±) and (−) borneol) [204]; (±) borneol also inhibits M-3-G and M-6-G formation by human liver microsomes (HLM) [204]. At 200 μM, borneol inhibits microsomal glucuronidation of propofol [185], and pre-treatment with (−)-borneol in mice increases propofol’s Cmax and AUC while reducing its volume of distribution at steady state (Vss) [185]. Borneol also causes a dose-dependent decrease in St unit firing (spontaneous and mechanically evoked) [205]. However, at the concentration present in LEO (0.00097%), it is ineffective in modulating neutral lipid and free cholesterol accumulation in HepG2 cells [188]. Notably, bornyl acetate (with an ester group) has greater activity against most tested microorganisms than borneol [206].
References
[1] Borges, Raphaelle Sousa; Sanchez Ortiz, Brenda Lorena; Matias Pereira, Arlindo Cesar; Keita, Hady; Tavares Carvalho, Jose Carlos, Rosmarinus officinalis Essential oil: A review of its phytochemistry, anti-inflammatory activity, and mechanisms of action involved, 2018, JOURNAL OF ETHNOPHARMACOLOGY
[2] Rahimmalek, Mehdi; Tabatabaeb, Badraldin Ebrahim Sayed; Etemadi, Nematolah; Goli, Sayed Amir Hossein; Arzani, Ahmad; Zeinali, Hossein, Essential oil variation among and within six Achillea species transferred from different ecological regions in Iran to the field conditions, 2009, INDUSTRIAL CROPS AND PRODUCTS
[3] Mohsen, Haouari; Ali, Ferchichi, Essential Oil Composition of Artemisia herba-alba from Southern Tunisia, 2009, MOLECULES
[4] Cáceres, J.A.; Cuervo A, J.L.; Rodríguez C, J.L., Effect of organic fertilization on yield and quality of rosemary (Rosmarinus officinalis L.) essential oil, 2017, Agronomia Colombiana
[5] Presti, M.L.; Ragusa, S.; Trozzi, A.; Dugo, P.; Visinoni, F.; Fazio, A.; Dugo, G.; Mondello, L., A comparison between different techniques for the isolation of rosemary essential oil, 2005, Journal of Separation Science
[6] Caprari C, Fantasma F, Monaco P, Divino F, Iorizzi M, Ranalli G, Fasano F, Saviano G., Chemical Profiles, In Vitro Antioxidant and Antifungal Activity of Four Different Lavandula angustifolia L. EOs, 2023, Molecules
[7] Kavallieratos, Nickolas G.; Skourti, Anna; Nika, Erifili P.; Martonfi, Pavol; Spinozzi, Eleonora; Maggi, Filippo, Tanacetum vulgare essential oil as grain protectant against adults and larvae of four major stored-product insect pests, 2021, JOURNAL OF STORED PRODUCTS RESEARCH
[8] Khavarpour, M.; Vahdat, S.M.; Kazemi, S.; Moghadamnia, A.A.; Hasanzadeh, O.; Salimi, Z.; Rahmanpour, N., Chemical Composition, Antibacterial and Analgesic Activity of Lavandula stoechas Flowers from North of Iran, 2019, International Journal of Engineering, Transactions B: Applications
[9] Bencharif-Betina, S.; Benhamed, N.; Benabdallah, A.; Hamdi, H.; Benslama, A.; Negro, C.; Plavan, G.; Abd-Elkader, O.H.; De Bellis, L., A Multi-Approach Study of Phytochemicals and Their Effects on Oxidative Stress and Enzymatic Activity of Essential Oil and Crude Extracts of Rosmarinus officinalis, 2023, Separations
[10] Hamdi, H.; Boudjeniba, M.; Miara, M.D.; Biqiku, L.; Bramucci, M.; Lupidi, G.; Quassinti, L.; Vitali, L.A.; Maggi, F., Essential oil of Thymus munbyanus subsp. coloratus from Algeria: chemotypification and in vitro biological activities, 2017, Chemistry and Biodiversity
[11] Zhang T, Zheng Y, Fu C, Yang H, Liu X, Qiu F, Wang X, Wang Z., Chemical Variation and Environmental Influence on Essential Oil of Cinnamomum camphora, 2023, Molecules
[12] Doungchawee, Jeerapat; Kulsing, Chadin; Suekaew, Naruemon; Pombejra, Sarisa Na; Chavasiri, Warinthorn; Plabutong, Napasawan; Thammahong, Arsa; Khotavivattana, Tanatorn, Volatile Chemical Composition, Antibacterial and Antifungal Activities of Extracts from Different Parts of Globba schomburgkii Hook. f., 2019, CHEMISTRY & BIODIVERSITY
[13] Plata-Rueda, Angelica; Zanuncio, Jose Cola; Serrao, Jose Eduardo; Martinez, Luis Carlos, Origanum vulgare Essential Oil against Tenebrio molitor (Coleoptera: Tenebrionidae): Composition, Insecticidal Activity, and Behavioral Response, 2021, PLANTS-BASEL
[14] El-Ghorab, A.; Shaaban, H.A.; El-Massry, K.F.; Shibamoto, T., Chemical Composition of Volatile Extract and Biological Activities of Volatile and Less-Volatile Extracts of Juniper Berry (Juniperus drupacea L.) Fruit, 2008, Journal of Agricultural and Food Chemistry
[15] Idowu, D. O.; Aiyelaagbe, O. O.; Idowu, P. A., Chemical composition and biological activities of volatile oil of the stem of Dombeya buettneri K. Schum. (Sterculiaceae), 2023, SCIENTIFIC AFRICAN
[16] Najar B, Pistelli L, Venturi F, Ferroni G, Giovanelli S, Cervelli C, Bedini S, Conti B., Salvia Spp. Essential Oils against the Arboviruses Vector Aedes albopictus (Diptera: Culicidae): Bioactivity, Composition, and Sensorial Profile—Stage 1, 2020, Biology (Basel)
[17] Santamarina, M.P.; Ibáñez, M.D.; Marqués, M.; Roselló, J.; Giménez, S.; Blàzquez, M.A., Bioactivity of essential oils in phytopathogenic and post-harvest fungi control, 2017, Natural Product Research
[18] Giuliani, Claudia; Bottoni, Martina; Ascrizzi, Roberta; Milani, Fabrizia; Spada, Alberto; Papini, Alessio; Flamini, Guido; Fico, Gelsomina, Insight into micromorphology and phytochemistry of Lavandula angustifolia Mill. from Italy, 2023, SOUTH AFRICAN JOURNAL OF BOTANY
[19] Judzentiene, Asta; Budiene, Jurga; Stancelyte, Donata; Nedveckyte, Irena, Phytochemistry and Allelopathic Effects of Tanacetum vulgare L. (Tansy) Extracts on Lepidium sativum L. (Garden Pepper Cress) and Lactuca sativa L. (Lettuce), 2024, HORTICULTURAE
[20] Pavela, R.; Maggi, F.; Mazzara, E.; Torresi, J.; Cianfaglione, K.; Benelli, G.; Canale, A., Prolonged sublethal effects of essential oils from non-wood parts of nine conifers on key insect pests and vectors, 2021, Industrial Crops and Products
[21] Liu, Z.L.; Liu, Q.R.; Chu, S.S.; Jiang, G.H., Insecticidal Activity and Chemical Composition of the Essential Oils of Artemisia lavandulaefolia and Artemisia sieversiana from China, 2010, Chemistry and Biodiversity
[22] Musa Özcan, M.; Akgül, A.; Chalchat, J.C., Volatile Constituents of Essential Oils of Salvia aucheri Benth. var. canescens Boiss. et Heldr. and S. tomentosa Mill. Grown in Turkey, 2002, Journal of Essential Oil Research
[23] Pezet, Joshua; Elkinton, Joseph S., Hemlock Woolly Adelgid (Hemiptera: Adelgidae) Induces Twig Volatiles of Eastern Hemlock in a Forest Setting, 2014, ENVIRONMENTAL ENTOMOLOGY
[24] Asghari B, Hoseinzadeh M, Mafakheri S., Enhancing drought resistance in Dracocephalum moldavica L. through mycorrhizal fungal inoculation and melatonin foliar application, 2025, Sci Rep
[25] Athanasiadis V, Lakka A, Palaiogiannis D, Pappas VM, Bozinou E, Ntourtoglou G, Makris DP, Dourtoglou VG, Lalas SI., Pulsed Electric Field and Salvia officinalis L. Leaves: A Successful Combination for the Extraction of High Value Added Compounds, 2021, Foods
[26] Cheng, Ke; Peng, Bangzhu; Yuan, Fang, Volatile composition of eight blueberry cultivars and their relationship with sensory attributes, 2020, FLAVOUR AND FRAGRANCE JOURNAL
[27] Simoneit, Bernd R. T.; Otto, Angelika; Kusumoto, Norihisa; Basinger, James F., Biomarker compositions of Glyptostrobus and Metasequoia (Cupressaceae) fossils from the Eocene Buchanan Lake Formation, Axel Heiberg Island, Nunavut, Canada reflect diagenesis from terpenoids of their related extant species, 2016, REVIEW OF PALAEOBOTANY AND PALYNOLOGY
[28] Arya S, Kumar R, Prakash O, Kumar S, Mahawer SK, Chamoli S, Kumar P, Srivastava RM, de Oliveira MS., Chemical Composition and Biological Activities of Hedychium coccineum Buch.-Ham. ex Sm. Essential Oils from Kumaun Hills of Uttarakhand, 2022, Molecules
[29] Smiljanić K, Prodić I, Trifunovic S, Krstić Ristivojević M, Aćimović M, Stanković Jeremić J, Lončar B, Tešević V., Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts, 2023, Antioxidants (Basel)
[30] Jerkovic, Igor; Kus, Piotr Marek; Tuberoso, Carlo Ignazio Giovanni; Sarolic, Mladenka, Phytochemical and physical–chemical analysis of Polish willow (Salix spp.) honey: Identification of the marker compounds, 2013, FOOD CHEMISTRY
[31] Kostanda, Elizabeth; Khatib, Soliman, Biotic stress caused by Tetranychus urticae mites elevates the quantity of secondary metabolites, cannabinoids and terpenes, in Cannabis sativa L., 2022, INDUSTRIAL CROPS AND PRODUCTS
[32] Quassinti, L.; Maggi, F.; Ortolani, F.; Lupidi, G.; Petrelli, D.; Vitali, L.A.; Miano, A.; Bramucci, M., Exploring new applications of tulip tree (Liriodendron tulipifera L.): leaf essential oil as apoptotic agent for human glioblastoma, 2019, Environmental Science and Pollution Research
[33] Kļaviņa A, Keidāne D, Šukele R, Bandere D, Kovaļčuka L., Traditional Latvian herbal medicinal plants used to treat parasite infections of small ruminants: A review, 2021, Vet World
[34] Nafis, A.; Ouedrhiri, W.; Iriti, M.; Mezrioui, N.; Marraiki, N.; Elgorban, A. M.; Syed, A.; Hassani, L., Chemical composition and synergistic effect of three Moroccan lavender EOs with ciprofloxacin against foodborne bacteria: a promising approach to modulate antimicrobial resistance, 2021, LETTERS IN APPLIED MICROBIOLOGY
[35] Tava, Aldo; Biazzi, Elisa; Ronga, Domenico; Avato, Pinarosa, Identification of the Volatile Components of Galium verum L. and Cruciata leavipes Opiz from the Western Italian Alps, 2020, MOLECULES
[36] Oumzil, H.; Ghoulami, S.; Rhajaoui, M.; Ilidrissi, A.; Fkih-Tétouani, S.; Paid, M.; Benjouad, A., Antibacterial and Antifungal Activity of Essential Oils of Mentha suaveolens, 2002, Phytotherapy Research
[37] Torres Neto L, Monteiro MLG, Machado MAM, Galvan D, Conte Junior CA., An Optimization of Oregano, Thyme, and Lemongrass Essential Oil Blend to Simultaneous Inactivation of Relevant Foodborne Pathogens by Simplex–Centroid Mixture Design, 2022, Antibiotics (Basel)
[38] Ćavar Zeljković, S.; Maksimović́, M.; Vidic, D., The Essential Oil of Thymus aureopunctatus (Beck) K. Malý, 2009, Natural Product Communications
[39] Fernandes L, Ribeiro R, Costa R, Henriques M, Rodrigues ME., Essential Oils as a Good Weapon against Drug-Resistant Candida auris, 2022, Antibiotics (Basel)
[40] Abbasi, Shahrbanoo; Houshmand, Sadollah; Ghorbani, Samira, Gene expression and metabolite analyses of Thymus daenensis and T.vulgaris in the Trichome and leaf at two phenological stages, 2024, BIOCATALYSIS AND AGRICULTURAL BIOTECHNOLOGY
[41] Sabra, A.S.; Astatkie, T.; Alataway, A.; Mahmoud, A.A.; Gendy, A.S.H.; Said-Al Ahl, H.A.H.; Tkachenko, K.G., Response of biomass development, essential oil and composition of Plectranthus amboinicus (Lour.) Spreng to irrigation frequency and harvest time, 2018, Chemistry and Biodiversity
[42] Stojanović, J.P.; Stojanović, G.S.; Stojanović-Radić, Z.Z.; Zlatkovic̈, B.K.; Ickovski, J.D.; Zlatanović, I.G.; Jovanović, S.Č.; Mitić, Z.S., Essential Oils of Six Achillea Species: Chemical Profiles, Antimicrobial Potential and Toxicity toward Crustaceans, 2022, Chemistry and Biodiversity
[43] Maggio, Antonella; Riccobono, Luana; Spadaro, Vivienne; Campisi, Patrizia; Bruno, Maurizio; Senatore, Felice, Volatile Constituents of the Aerial Parts of Pulicaria sicula (L.) Moris Growing Wild in Sicily: Chemotaxonomic Volatile Markers of the Genus Pulicaria Gaertn., 2015, CHEMISTRY & BIODIVERSITY
[44] Nikolić, B.; Tešević, V.; Bajić, D.; Bojović, S.; Marin, P.D., NEEDLE ESSENTIAL OIL COMPOSITION OF Picea omorika VAR. vukomanii, 2008, Chemistry of Natural Compounds
[45] Del Carmen Beristain-Bauza, Silvia; Hernandez-Carranza, Paola; Soledad Cid-Perez, Teresa; Avila-Sosa, Raul; Israel Ruiz-Lopez, Irving; Enrique Ochoa-Velasco, Carlos, Antimicrobial Activity of Ginger (Zingiber Officinale) and Its Application in Food Products, 2019, FOOD REVIEWS INTERNATIONAL
[46] Rana, V.S.; Amparo Blázquez, M., Chemical composition of the volatile oil of Ageratum conyzoides aerial parts, 2003, International Journal of Aromatherapy
[47] Aćimović, M.; Semerdjieva, I.; Zheljazkov, V.D.; Rat, M.; Stanković Jeremić, J.; Lončar, B.; Vukic, V.; Radovanović, K.; Gavarić, N.; Pezo, L., Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm, 2023, Biochemical Systematics and Ecology
[48] Mato A, Agúndez J, Márquez-Álvarez C, Mayoral Á, Pérez-Pariente J., Modulation of the Activity of Gold Clusters Immobilized on Functionalized Mesoporous Materials in the Oxidation of Cyclohexene via the Functional Group. The Case of Aminopropyl Moiety, 2020, Molecules
[49] Tounekti, Taieb; Vadel, Ahmedou Mohammed; Ennajeh, Mustapha; Khemira, Habib; Munne-Bosch, Sergi, Ionic interactions and salinity affect monoterpene and phenolic diterpene composition in rosemary (Rosmarinus officinalis), 2011, JOURNAL OF PLANT NUTRITION AND SOIL SCIENCE
[50] Rossi, D.; Guerrini, A.; Paganetto, G.; Bernacchia, G.; Conforti, F.; Statti, G.; Maietti, S.; Poppi, I.; Tacchini, M.; Sacchetti, G., Croton lechleri Müll. Arg. (Euphorbiaceae) stem bark essential oil as possible mutagen-protective food ingredient against heterocyclic amines from cooked food, 2013, Food Chemistry
[51] Regnier, Thierry; du Plooy, Wilma; Combrinck, Sandra; Botha, Ben, Fungitoxicity of Lippia scaberrima essential oil and selected terpenoid components on two mango postharvest spoilage pathogens, 2008, POSTHARVEST BIOLOGY AND TECHNOLOGY
[52] John Zachariah, T.J.; Leela, N.K., Spices: Secondary Metabolites and Medicinal Properties, 2018, Indian Spices: The Leg., Production and Processing of India's Treasured Export
[53] Peron, G.; Baldan, V.; Sut, S.; Faggian, M.; Roccabruna, L.; Zanini, D.; Manzini, P.; Maggi, F.; Dall'Acqua, S., Phytochemical investigations on Artemisia alba Turra growing in the North-East of Italy, 2017, Natural Product Research
[54] de Lima MNN, Santos PVL, Jerônimo LB, Viana RM, da Silva JK, Setzer WN, Maia JGS, Figueiredo PLB., Seasonal influence on the essential oil chemical composition of Hyptis crenata Pohl ex Benth.: a valuable plant from Marajó, Brazil, 2024, Front Chem
[55] Semiz, Gurkan; Heijari, Juha; Isik, Kani; Holopainen, Jarmo K., Variation in needle terpenoids among Pinus sylvestris L. (Pinaceae) provenances from Turkey, 2007, BIOCHEMICAL SYSTEMATICS AND ECOLOGY
[56] Kucukaydin, Selcuk; Tel-Cayan, Gulsen; Duru, Mehmet Emin; Kesdek, Memis; Ozturk, Mehmet, Chemical composition and insecticidal activities of the essential oils and various extracts of two Thymus species: Thymus cariensis and Thymus cilicicus, 2020, TOXIN REVIEWS
[57] Erzen, Marjeta; Kosir, Iztok J.; Ocvirk, Miha; Kreft, Samo; Cerenak, Andreja, Metabolomic Analysis of Cannabinoid and Essential Oil Profiles in Different Hemp (Cannabis sativa L.) Phenotypes, 2021, PLANTS-BASEL
[58] Asghari, G.; Jalali, M.; Sadoughi, E., Antimicrobial activity and chemical composition of essential oil from the seeds of artemisia aucheri boiss, 2012, Jundishapur Journal of Natural Pharmaceutical Products
[59] Al-Sayed, Eman, Unearthing the chemical composition of Taxodium distichum (L.) Rich. leaf essential oil and its antimicrobial activity, 2018, INDUSTRIAL CROPS AND PRODUCTS
[60] Chien, T.-C.; Lo, S.-F.; Ho, C.-L., Chemical Composition and Anti-inflammatory Activity of Chamaecyparis obtusa f. formosana Wood Essential Oil from Taiwan, 2014, Natural Product Communications
[61] Ghorbanpour, Mansour; Hadian, Javad, Variation of the Phytochemical Constituents of Different Individual Plants in Satureja macrosiphonia Bornm (Labiatae) Growing Wild in Iran, 2017, JOURNAL OF ESSENTIAL OIL BEARING PLANTS
[62] Bouyahya, Abdelhakim; Chamkhi, Imane; Benali, Taoufiq; Guaouguaou, Fatima-Ezzahrae; Balahbib, Abdelaali; El Omari, Nasreddine; Taha, Douae; Belmehdi, Omar; Ghokhan, Zengin; El Menyiy, Naoual, Traditional use, phytochemistry, toxicology, and pharmacology of Origanum majorana L., 2020, JOURNAL OF ETHNOPHARMACOLOGY
[63] Sadeh, D.; Nitzan, N.; Shachter, A.; Ghanim, M.; Dudai, N., Rosemary–Whitefly Interaction: A Continuum of Repellency and Volatile Combinations, 2019, Journal of Economic Entomology
[64] Wu L, Huo X, Zhou X, Zhao D, He W, Liu S, Liu H, Feng T, Wang C., Acaricidal Activity and Synergistic Effect of Thyme Oil Constituents against Carmine Spider Mite (Tetranychus Cinnabarinus (Boisduval)), 2017, Molecules
[65] Bendif, Hamdi; Peron, Gregorio; Miara, Mohamed Djamel; Sut, Stefania; Dall'Acqua, Stefano; Flamini, Guido; Maggi, Filippo, Total phytochemical analysis of Thymus munbyanus subsp. coloratus from Algeria by HS-SPME-GC-MS, NMR and HPLC-MSn studies, 2020, JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
[66] El-Shiekh RA, Okba MM, Mandour AA, Kutkat O, Elshimy R, Nagaty HA, Ashour RM., Eucalyptus Oils Phytochemical Composition in Correlation with Their Newly Explored Anti-SARS-CoV-2 Potential: in Vitro and in Silico Approaches, 2024, Plant Foods Hum Nutr
[67] Köse, Y.B.; Işcan, G.; Göger, F.; Demirci, B., Phytochemical Composition and Evaluation of Antimicrobial Activities of Five Salvia Species, 2025, Processes
[68] Šojić B, Ikonić P, Kocić-Tanackov S, Peulić T, Teslić N, Županjac M, Lončarević I, Zeković Z, Popović M, Vidaković S, Pavlić B., Antibacterial Activity of Selected Essential Oils against Foodborne Pathogens and Their Application in Fresh Turkey Sausages, 2023, Antibiotics (Basel)
[69] Andrys, D.; Kulpa, D., In Vitro Propagation Affects the Composition of Narrow-Leaved Lavender Essential Oils, 2018, Acta Chromatographica
[70] Li, J.; Chen, H.; Guo, C.; Chen, Q.; Zhao, T.; Chen, X.; Du, Y.; Du, H.; Miao, Y.; Liu, D., Artemisia argyi essential oil exerts herbicidal activity by inhibiting photosynthesis and causing oxidative damage, 2023, Industrial Crops and Products
[71] Nunes, Claudia; Raposo, M. Filomena de J.; Petronilho, Silvia; Machado, Fernanda; Fulgencio, Rita; Helena Gomes, M.; Evtuguin, Dmitry, V; Rocha, Silvia M.; Coimbra, Manuel A., Cinnamomum burmannii decoction: A thickening and flavouring ingredient, 2021, LWT-FOOD SCIENCE AND TECHNOLOGY
[72] Zhigzhitzhapova, S. V.; Namzalov, B-Ts. B.; Radnaeva, L. D., Composition of Essential Oil of Artemisia gmelinii Web. ex Stechm. of Priolkhonian Flora (Lake Baikal), 2021, CONTEMPORARY PROBLEMS OF ECOLOGY
[73] Ebadollahi, Asgar; Naseri, Bahram; Abedi, Zahra; Setzer, William N., Chemical Profiles and Insecticidal Potential of Essential Oils Isolated from Four Thymus Species against Rhyzopertha dominica (F.), 2022, PLANTS-BASEL
[74] Sennato S, Trabalzini S, Fabiano MG, Truzzolillo D, Chauveau E, Bombelli C, Rinaldi F, Carafa M., Effect of Satureja montana Essential Oil on Model Lipid Membranes, 2024, Biomolecules
[75] Krajewska, A.; Kalemba, D., Composition of rugosa rose (Rosa rugosa thunb.) hydrolate according to the time of distillation, 2015, Phytochemistry Letters
[76] Kačániová M, Garzoli S, Ben Hsouna A, Bianchi A, Kluz MI, Elizondo-Luevano JH, Ban Z, Ben Saad R, Mnif W, Haščík P., The Potential of Thymus serpyllum Essential Oil as an Antibacterial Agent against Pseudomonas aeruginosa in the Preservation of Sous Vide Red Deer Meat, 2024, Foods
[77] Shahrivari S, Alizadeh S, Ghassemi-Golezani K, Aryakia E., A comprehensive study on essential oil compositions, antioxidant, anticholinesterase and antityrosinase activities of three Iranian Artemisia species, 2022, Sci Rep
[78] Liu, Jiayi; Hua, Juan; Qu, Bo; Guo, Xuanyue; Wang, Yangyang; Shao, Meini; Luo, Shihong, Insecticidal Terpenes From the Essential Oils of Artemisia nakaii and Their Inhibitory Effects on Acetylcholinesterase, 2021, FRONTIERS IN PLANT SCIENCE
[79] Han, Jun; Kim, Soon-Il; Choi, Byeoung-Ryeol; Lee, Sang-Guei; Ahn, Young-Joon, Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae, 2011, PEST MANAGEMENT SCIENCE
[80] Nampoothiri, S.V.; Nirmala Menon, A.N.; Esakkidurai, T.; Pitchumani, K., Essential Oil Composition of Alpinia calcarata and Alpinia galanga Rhizomes-A Comparative Study, 2016, Journal of Essential Oil-Bearing Plants
[81] Argentieri, M.P.; De Lucia, B.; Cristiano, G.; Avatoa, P., Compositional Analysis of Lavandula pinnata Essential Oils, 2016, Natural Product Communications
[82] Chu SS, Liu ZL, Du SS, Deng ZW., Chemical Composition and Insecticidal Activity Against Sitophilus zeamais of the Essential Oils Derived from Artemisia giraldii and Artemisia subdigitata, 2012, Molecules
[83] Staudt, M.; Lhoutellier, L., Monoterpene and sesquiterpene emissions from Quercus coccifera exhibit interacting responses to light and temperature, 2011, Biogeosciences
[84] Nogueira, JMF; Romano, A, Essential Oils from Micropropagated Plants of Lavandula viridis, 2002, PHYTOCHEMICAL ANALYSIS
[85] Chorianopoulos, N.; Evergetis, E.; Mallouchos, A.; Kalpoutzakis, E.; Nychas, G.-J.; Haroutounian, S.A., Characterization of the Essential Oil Volatiles of Satureja thymbra and Satureja parnassica: Influence of Harvesting Time and Antimicrobial Activity, 2006, Journal of Agricultural and Food Chemistry
[86] Ghoran, Salar Hafez; Azadi, Boshra; Hussain, Hidayat, Chemical composition and antimicrobial activities of Perovskia artemisioides Boiss. essential oil, 2016, NATURAL PRODUCT RESEARCH
[87] Dob, T.; Dahmane, D.; Benabdelkader, T.; Chelghoum, C., Composition and Antimicrobial Activity of the Essential Oil of Thymus fontanesii, 2006, PHARMACEUTICAL BIOLOGY
[88] Kremer, D.; Müller, I.D.; Stabentheiner, E.; Vitali, D.; Kopričanec, M.; Ruščić, M.; Kosalec, I.; Bezic̈, N.; Dunkic̈, V., Phytochemical and Micromorphological Traits of Endemic Micromeria pseudocroatica (Lamiaceae), 2012, Natural Product Communications
[89] Motelica, Ludmila; Vasile, Bogdan-Stefan; Ficai, Anton; Surdu, Adrian-Vasile; Ficai, Denisa; Oprea, Ovidiu-Cristian; Andronescu, Ecaterina; Mustatea, Gabriel; Ungureanu, Elena Loredana; Dobre, Alina Alexandra, Antibacterial Activity of Zinc Oxide Nanoparticles Loaded with Essential Oils, 2023, PHARMACEUTICS
[90] Lawson, Sims K.; Satyal, Prabodh; Setzer, William N., The Volatile Phytochemistry of Seven Native American Aromatic Medicinal Plants, 2021, PLANTS-BASEL
[91] Dolghi A, Coricovac D, Dinu S, Pinzaru I, Dehelean CA, Grosu C, Chioran D, Merghes PE, Sarau CA., Chemical and Antimicrobial Characterization of Mentha piperita L. and Rosmarinus officinalis L. Essential Oils and In Vitro Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells, 2022, Molecules
[92] Hosseini A, Mobasheri L, Rakhshandeh H, Rahimi VB, Najafi Z, Askari VR., Edible Herbal Medicines as an Alternative to Common Medication for Sleep Disorders: A Review Article, 2024, Curr Neuropharmacol
[93] Memon A, Kim BY, Kim SE, Pyao Y, Lee YG, Kang SC, Lee WK., Anti-Inflammatory Effect of Phytoncide in an Animal Model of Gastrointestinal Inflammation, 2021, Molecules
[94] Nagalakshmi, M.A.H.; Thangadurai, D.; Anuradha, T.; Pullaiah, T., Essential oil constituents of Melia dubia, a wild relative of Azadirachta indica growing in the Eastern Ghats of Peninsular India, 2001, Flavour and Fragrance Journal
[95] Abdel-Sattar, E.; Zaitoun, A.A.; Farag, M.A.; El-Gayed, S.H.; Harraz, F.M.H., Chemical composition, insecticidal and insect repellent activity of Schinus molle L. leaf and fruit essential oils against Trogoderma granarium and Tribolium castaneum, 2010, Natural Product Research
[96] Tabanca, N.; Demirci, B.; Başer, K.H.C.; Aytaç, Z.; Ekící, M.; Khan, S.I.; Jacob, M.R.; Wedge, D.E., Chemical Composition and Antifungal Activity of Salvia macrochlamys and Salvia recognita Essential Oils, 2006, Journal of Agricultural and Food Chemistry
[97] El-Kharraf S, El-Guendouz S, Abdellah F, El Hadrami EM, Machado AM, Tavares CS, Figueiredo AC, Miguel MG., Unassisted and Carbon Dioxide-Assisted Hydro- and Steam-Distillation: Modelling Kinetics, Energy Consumption and Chemical and Biological Activities of Volatile Oils, 2022, Pharmaceuticals (Basel)
[98] Nadeem, Muhammad; Anjum, Faqir Muhammad; Khan, Muhammad Issa; Tehseen, Saima; El-Ghorab, Ahmed; Sultan, Javed Iqbal, Nutritional and medicinal aspects of coriander (Coriandrum sativum L.): A review, 2013, BRITISH FOOD JOURNAL
[99] Blanc, M.-C.; Muselli, A.; Bradesi, P.; Casanova, J., Chemical composition and variability of the essential oil of Inula graveolens from Corsica, 2004, Flavour and Fragrance Journal
[100] Kozlowska, Weronika; Matkowski, Adam; Zielinska, Sylwia, Light Intensity and Temperature Effect on Salvia yangii (B. T. Drew) Metabolic Profile in vitro, 2022, FRONTIERS IN PLANT SCIENCE
[101] Chauhan, A.; Verma, R.S.; Chandra Padalia, R.C.; Upadhyay, R.K.; Bahl, J.R., Post harvest storage effect on essential oil content and composition of Cymbopogon distans (Nees ex Steud.) Wats., 2016, Journal of Essential Oil Research
[102] Olsoy, Peter J.; Forbey, Jennifer S.; Shipley, Lisa A.; Rachlow, Janet L.; Robb, Brecken C.; Nobler, Jordan D.; Thornton, Daniel H., Mapping foodscapes and sagebrush morphotypes with unmanned aerial systems for multiple herbivores, 2020, LANDSCAPE ECOLOGY
[103] Damyeh, Maral Seidi; Niakousari, Mehrdad; Saharkhiz, Mohammad Jamal; Golmakani, Mohammad Taghi, EVALUATING THE EFFECT OF ESSENTIAL OIL EXTRACTION METHOD FROM SATUREJA MACROSIPHONIA ON ITS BIOLOGICAL ACTIVITIES: OHMIC- AND MICROWAVE-ASSISTED HYDRODISTILLATION, 2016, JOURNAL OF FOOD PROCESSING AND PRESERVATION
[104] Wang K, Yang Z, Luo S, Quan W., Endophytic Pseudomonas fluorescens promotes changes in the phenotype and secondary metabolite profile of Houttuynia cordata Thunb., 2024, Sci Rep
[105] Younsi, Faten; Rahali, Najoua; Mehdi, Sameh; Boussaid, Mohamed; Messaoud, Chokri, Relationship between chemotypic and genetic diversity of natural populations of Artemisia herba-alba Asso growing wild in Tunisia, 2018, PHYTOCHEMISTRY
[106] Hawley, Dave; Graham, Thomas; Stasiak, Michael; Dixon, Mike, Improving Cannabis Bud Quality and Yield with Subcanopy Lighting, 2018, HORTSCIENCE
[107] Nasiri, Ehsan; Shekari, Fariborz; Abbasi, Amin; Morshedloo, Mohammad Reza; Ghorbanpour, Mansour, Exogenous γ-aminobutyric acid mitigates drought-induced impairments in Thymus daenensis Celak by regulating physiological traits, antioxidant enzymes and essential oil constituents, 2025, BMC PLANT BIOLOGY
[108] Elansary HO, El-Ansary DO, Al-Mana FA., 5-Aminolevulinic Acid and Soil Fertility Enhance the Resistance of Rosemary to Alternaria dauci and Rhizoctonia solani and Modulate Plant Biochemistry, 2019, Plants (Basel)
[109] Nikolic, Biljana; Ristic, Mihailo; Bojovic, Srdjan; Matevski, Vlado; Krivosej, Zoran; Marin, Petar D., Essential-Oil Composition of the Needles Collected from Natural Populations of Macedonian Pine (Pinus peuce Griseb.) from the Scardo-Pindic Mountain System, 2014, CHEMISTRY & BIODIVERSITY
[110] Yu AN, Yang YN, Yang Y, Liang M, Zheng FP, Sun BG., Free and Bound Aroma Compounds of Turnjujube (Hovenia acerba Lindl.) during Low Temperature Storage, 2020, Foods
[111] Verma, Ram S.; Padalia, Rajendra C.; Chauhan, Amit; Verma, Rajesh K.; Yadav, Ajai K.; Singh, Hemendra P., Chemical Diversity in Indian Oregano (Origanum vulgare L.), 2010, CHEMISTRY & BIODIVERSITY
[112] Guitton, Yann; Nicole, Florence; Moja, Sandrine; Valot, Nadine; Legrand, Sylvain; Jullien, Frederic; Legendre, Laurent, Differential accumulation of volatile terpene and terpene synthase mRNAs during lavender (Lavandula angustifolia and L. x intermedia) inflorescence development, 2010, PHYSIOLOGIA PLANTARUM
[113] Peace, Michelle R.; Stone, Joseph W.; Poklis, Justin L.; Turner, Joseph B. M.; Poklis, Alphonse, Analysis of a Commercial Marijuana e-Cigarette Formulation, 2016, JOURNAL OF ANALYTICAL TOXICOLOGY
[114] Widhiantara, I. Gede; Jawi, I. Made, Phytochemical composition and health properties of Sembung plant (Blumea balsamifera): A review, 2021, VETERINARY WORLD
[115] Lucini, E.I.; Zunino, M.P.; López, M.L.; Zygadlo, J.A., Effect of Monoterpenes on Lipid Composition and Sclerotial Development of Sclerotium cepivorum Berk., 2006, Journal of Phytopathology
[116] Bhatia, S.P.; Letizia, C.S.; Api, A.M., Fragrance material review on borneol, 2008, Food and Chemical Toxicology
[117] Tikhonova, I., V, The Possibility of Studying the Processes of Interconversion of Volatile Compounds of Needles on the Basis of Static Data, 2022, BIOLOGY BULLETIN
[118] Yoo, SK; Day, DF; Cadwallader, KR, Bioconversion of α- and β-pinene by Pseudomonas sp. strain PIN, 2001, PROCESS BIOCHEMISTRY
[119] Ma, R.; Lu, D.; Wang, J.; Xie, Q.; Guo, J., Comparison of pharmacological activity and safety of different stereochemical configurations of borneol: L-borneol, D-borneol, and synthetic borneol, 2023, Biomedicine and Pharmacotherapy
[120] Baby, S.; Raj, G.; Thaha, A.R.M.; Dan, M., Volatile chemistry of a plant: monosesquiterpenoid pattern in the growth cycle of Curcuma haritha, 2010, Flavour and Fragrance Journal
[121] Caputo, L.; Trotta, M.; Romaniello, A.; de Feo, V., Chemical Composition and Phytotoxic Activity of Rosmarinus officinalis Essential Oil, 2018, Natural Product Communications
[122] Guo, Siyuan; Liang, Jiahao; Deng, Zhiwei; Lu, Ziqing; Fu, Minghui; Su, Jianyu, Full-Length Transcriptome Sequencing Combined with RNA-Seq to Analyze Genes Related to Terpenoid Biosynthesis in Cinnamomum burmannii, 2022, CURRENT ISSUES IN MOLECULAR BIOLOGY
[123] Singh, Priyanka; Kalunke, Raviraj M.; Shukla, Anurag; Tzfadia, Oren; Thulasiram, Hirekodathakallu, V; Giri, Ashok P., Biosynthesis and tissue-specific partitioning of camphor and eugenol in Ocimum kilimandscharicum, 2020, PHYTOCHEMISTRY
[124] Loizzo, M.R.; Ben Jemia, M.; Senatore, F.; Bruno, M.; Menichini, F.; Tundis, R., Chemistry and functional properties in prevention of neurodegenerative disorders of five Cistus species essential oils, 2013, Food and Chemical Toxicology
[125] Politi M, Ferrante C, Menghini L, Angelini P, Flores GA, Muscatello B, Braca A, De Leo M., Hydrosols from Rosmarinus officinalis, Salvia officinalis, and Cupressus sempervirens: Phytochemical Analysis and Bioactivity Evaluation, 2022, Plants (Basel)
[126] Machado, M.; Dinis, A. M.; Santos-Rosa, M.; Alves, V.; Salgueiro, L.; Cavaleiro, C.; Sousa, M. C., Activity of Thymus capitellatus volatile extract, 1,8-cineole and borneol against Leishmania species, 2014, VETERINARY PARASITOLOGY
[127] Jaitak, V.; Singh, B.; Kaul, V.K., Variability of volatile constituents in Artemisia maritima in western Himalaya, 2008, Natural Product Research
[128] Tawfeeq, A.A.; Mahdi, M.F.; Abaas, I.S.; Alwan, A.H., ISOLATION, QUANTIFICATION, AND IDENTIFICATION OF ROSMARINIC ACID, GAS CHROMATOGRAPHY-MASS SPECTROMETRY ANALYSIS OF ESSENTIAL OIL, CYTOTOXIC EFFECT, AND ANTIMICROBIAL INVESTIGATION OF ROSMARINUS OFFICINALIS LEAVES, 2018, Asian Journal of Pharmaceutical and Clinical Research
[129] Eftekhar, F.; Nariman, F.; Yousefzadi, M.; Hadian, J.; Nejad Ebrahimi, S.N., Anti-Helicobacter pylori activity and Essential Oil Composition of Thymus caramanicus from Iran, 2009, Natural Product Communications
[130] Filatov, Viktor A.; Ilin, Egor A.; Kulyak, Olesya Yu.; Kalenikova, Elena I., Development and Validation of a Gas Chromatography–Mass Spectrometry Method for the Analysis of the Novel Plant-Based Substance with Antimicrobial Activity, 2023, ANTIBIOTICS-BASEL
[131] Diken, M.E.; Kardas, B.Y., Inhibitory effect on acetylcholinesterase and toxicity analysis of some medicinal plants, 2022, International Journal of Secondary Metabolite
[132] Simoh, S.; Zainal, A., Chemical profiling of Curcuma aeruginosa Roxb. rhizome using different techniques of solvent extraction, 2015, Asian Pacific Journal of Tropical Biomedicine
[133] Wajs-Bonikowska, A.; Olejnik, K.; Bonikowski, R.; Banaszczak, P., Composition of Essential Oils from Seeds of Abies koreana, 2013, Natural Product Communications
[134] Charrie-Duhaut, Armelle; Connan, Jacques; Darnell, Mike; Spangenberg, Jorge; Szymczyk, Ewa; Bissada, Adry; Albrecht, Pierre, Molecular and isotopic characterization of organic samples from the wreck of the Saint-Etienne merchant ship (XVIIIth century): Identification of pitch, fat, hair and sulfur, 2009, ORGANIC GEOCHEMISTRY
[135] Bhardwaj, K.; Islam, M.T.; Jayasena, V.; Sharma, B.; Sharma, S.; Sharma, P.; Kuča, K.; Bhardwaj, P., Review on essential oils, chemical composition, extraction, and utilization of some conifers in Northwestern Himalayas, 2020, Phytotherapy Research
[136] Cakmakci, Ramazan; Mosber, Goltay; Milton, Ada Hazal; Alaturk, Firat; Ali, Baboo, The Effect of Auxin and Auxin-Producing Bacteria on the Growth, Essential Oil Yield, and Composition in Medicinal and Aromatic Plants, 2020, CURRENT MICROBIOLOGY
[137] Zhigzhitzhapova, Svetlana V.; Dylenova, Elena P.; Goncharova, Danaya B.; Zhigzhitzhapov, Bato V.; Emelyanova, Elena A.; Polonova, Anastasiya V.; Tykheev, Zhargal A.; Bazarsadueva, Selmeg V.; Taraskina, Anna S.; Pintaeva, Evgeniya T.; Taraskin, Vasiliy V., Functional Activity of the Antioxidant System of Artemisia Genus Plants in the Republic of Buryatia (Russia) and Its Significance in Plant Adaptation, 2024, PLANTS-BASEL
[138] Jakovljević M, Jokić S, Molnar M, Jašić M, Babić J, Jukić H, Banjari I., Bioactive Profile of Various Salvia officinalis L. Preparations, 2019, Plants (Basel)
[139] Cutillas AB, Carrasco A, Martinez-Gutierrez R, Tomas V, Tudela J., Thymus mastichina L. essential oils from Murcia (Spain): Composition and antioxidant, antienzymatic and antimicrobial bioactivities, 2018, PLoS One
[140] Larkov, O.; Mayer, A.M.; Ravid, U., Chiral monoterpenes as "enantiotaxonomy" indicators for the genera Origanum, Salvia, and Rosmarinus, 2010, Israel Journal of Plant Sciences
[141] Krupcik, Jan; Gorovenko, Roman; Spanik, Ivan; Armstrong, Daniel W.; Sandra, Pat, Enantioselective comprehensive two-dimensional gas chromatography of lavender essential oil, 2017, JOURNAL OF SEPARATION SCIENCE
[142] Gorman, Claire; Murray, Anne F.; Dein, Melissa; Munafo Jr, John P., Characterization of Key Odorants in Cumberland Rosemary, Conradina verticillata, 2022, JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
[143] Naspi, Cecilia; Costa, Agustin A.; Lucia, Alejandro; Audino, Paola G.; Masuh, Hector M., Enantiomeric Ratio Changes of Terpenes in Essential Oils from Hybrid Eucalyptus grandis × E. tereticornis and its Pure Species, 2018, JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
[144] Wang, Chen; Zhang, Hongxia; Liu, Qing; Qi, Jinfeng; Zhuang, Huifu; Gou, Yi; Wang, Hongbin; Wang, Yuhua, A review of the aromatic genus Adenosma: Geographical distribution, traditional uses, phytochemistry and biological activities, 2021, JOURNAL OF ETHNOPHARMACOLOGY
[145] Lan Phi, N.T., GAS CHROMATOGRAPHY–OLFACTOMETRY AND AROMA-ACTIVE COMPONENTS IN CITRUS ESSENTIAL OILS, 2010, Citrus Essent. Oils: Flavor and Fragrance
[146] Ouakouak, Hamza; Benarfa, Adel; Messaoudi, Mohammed; Begaa, Samir; Sawicka, Barbara; Benchikha, Naima; Simal-Gandara, Jesus, Biological Properties of Essential Oils from Thymus algeriensis Boiss, 2021, PLANTS-BASEL
[147] Mastelic, J; Jerkovic, I; Kustrak, D, Aromatic Compounds of Micromeria juliana (L.) Bentham ex Reichenb. from Croatia, 2005, JOURNAL OF ESSENTIAL OIL RESEARCH
[148] Boneva, S., GAS CHROMATOGRAPHIC BEHAVIOR OF THE DIAGNOSTIC COMPONENTS OF SOME ESSENTIAL OILS, 2007, CHEMISTRY OF NATURAL COMPOUNDS
[149] Martins, Monia A. R.; Silva, Liliana P.; Schaeffer, Nicolas; Abranches, Dinis O.; Maximo, Guilherme J.; Pinho, Simao P.; Coutinho, Joao A. P., Greener Terpene-Terpene Eutectic Mixtures as Hydrophobic Solvents, 2019, ACS SUSTAINABLE CHEMISTRY & ENGINEERING
[150] Ullah, A.; Klutsch, J.G.; Erbilgin, N., Production of complementary defense metabolites reflects a co-evolutionary arms race between a host plant and a mutualistic bark beetle-fungal complex, 2021, Plant, Cell and Environment
[151] Vladic, Jelena; Kovacevic, Strahinja; Aladic, Krunoslav; Jokic, Stela; Radman, Sanja; Podunavac-Kuzmanovic, Sanja; Duarte, Ana Rita C.; Jerkovic, Igor, Innovative Strategy for Aroma Stabilization Using Green Solvents: Supercritical CO2 Extracts of Satureja montana Dispersed in Deep Eutectic Solvents, 2023, BIOMOLECULES
[152] Skalicka-Wozniak, Krystyna; Walasek, Magdalena; Aljarba, Tariq M.; Stapleton, Paul; Gibbons, Simon; Xiao, Jianbo; Luszczki, Jarogniew J., The anticonvulsant and anti-plasmid conjugation potential of Thymus vulgaris chemistry: An in vivo murine and in vitro study, 2018, FOOD AND CHEMICAL TOXICOLOGY
[153] Taherkhani, M., Mutagenic and antimutagenic activities of Artemisia absinthium volatile oil by the bacterial reverse mutation assay in Salmonella typhimurium strains TA98 and TA100, 2014, Asian Pacific Journal of Tropical Disease
[154] Kostic, Marina; Ivanov, Marija; Markovic, Tatjana; Sankovic Babic, Snezana; Barros, Lillian; Calhelha, Ricardo; Sokovic, Marina; Ciric, Ana, An in vitro study of the origanum minutiflorum O. Schwarz & P. H. Davis and Coriandrum sativum L. essential oils as chronic tonsillitis therapeutics: antibacterial, antibiofilm, antioxidant, and cytotoxic activities, 2022, JOURNAL OF ESSENTIAL OIL RESEARCH
[155] Ranaldi, Roberta; Rugnini, Lorenza; Gabriele, Francesco; Spreti, Nicoletta; Casieri, Cinzia; Di Marco, Gabriele; Gismondi, Angelo; Bruno, Laura, Plant essential oils suspended into hydrogel: Development of an easy-to-use protocol for the restoration of stone cultural heritage, 2022, INTERNATIONAL BIODETERIORATION & BIODEGRADATION
[156] Marinas IC, Oprea E, Gaboreanu DM, Gradisteanu Pircalabioru G, Buleandra M, Nagoda E, Badea IA, Chifiriuc MC., Chemical and Biological Studies of Achillea setacea Herba Essential Oil—First Report on Some Antimicrobial and Antipathogenic Features, 2023, Antibiotics (Basel)
[157] Thin, Dau B.; Dai, Do N.; Ogunwande, Isiaka A., The Leaves and Rhizomes Essential Oils of Alpinia oblongifolia Hayata, 2018, JOURNAL OF ESSENTIAL OIL BEARING PLANTS
[158] Smigielski, Krzysztof B.; Prusinowska, Renata; Krosowiak, Krzysztof; Sikora, Magdalena, Comparison of qualitative and quantitative chemical composition of hydrolate and essential oils of lavender (Lavandula angustifolia), 2014, JOURNAL OF ESSENTIAL OIL RESEARCH
[159] Simić, N.; Palić, R.; Ranđelović, V., Composition and antibacterial activity of Achillea clypeolata essential oil, 2005, Flavour and Fragrance Journal
[160] Kim, S.-I.; Na, Y.-E.; Yoon, S.T.; Lee, J.-K.; Oh, Y.J., Nematicidal and ovicidal activities of Dryobalanops aromática and Mentha haplocalyx var. piperascens-derived materials and their formulations against Meloidogyne incognita second-stage juveniles and eggs, 2014, Nematology
[161] Zhigzhitzhapova, Svetlana V.; Randalova, Tuyana E.; Radnaeva, Larisa D.; Dylenova, Elena P.; Chen, Shilong; Zhang, Faqi, Chemical Composition of Essentials Oils of Artemisia frigida Willd. (Asteraceae) Grown in the North and Central Asia, 2018, JOURNAL OF ESSENTIAL OIL BEARING PLANTS
[162] Soltan MM, Mahfouz S, Motawe FH, Karam EA, El-Hagrassi A., In sight on olive oil maceration and supercritical CO2 in extracting rosemary essential oil, 2024, Sci Rep
[163] Kasali, AA; Adio, AM; Oyedeji, AO; Eshilokun, AO; Adefenwa, M, Volatile constituents of Boswellia serrata Roxb. (Burseraceae) bark, 2002, FLAVOUR AND FRAGRANCE JOURNAL
[164] Lafhal, Sofia; Vanloot, Pierre; Bombarda, Isabelle; Kister, Jacky; Dupuy, Nathalie, Chemometric analysis of French lavender and lavandin essential oils by near infrared spectroscopy, 2016, INDUSTRIAL CROPS AND PRODUCTS
[165] Formisano, C.; Senatore, F.; Bruno, M.; Bellone, G., Chemical composition and antimicrobial activity of the essential oil of Phlomis ferruginea Ten. (Lamiaceae) growing wild in Southern Italy, 2006, Flavour and Fragrance Journal
[166] Hurskainen, T.V.; Terentyev, V.I.; Skripova, N.N.; Korolyova, A.A.; Kutchin, A.V., The Study of the Chemical Composition of Pine Cedar Extract, 2015, Russian Journal of Bioorganic Chemistry
[167] Ren, M.; Guan, L.; Wang, N.; Xu, C.; Cui, Y.; He, D.; Wang, C.; Yang, Y., Investigation of the manufacture development of early Chinese ink in the Western Han dynasty, 2022, Archaeometry
[168] Usai, M; Atzei, A; Pintore, G; Casanova, L, Composition and variability of the essential oil of Sardinian Thymus herba-barona Loisel, 2003, FLAVOUR AND FRAGRANCE JOURNAL
[169] Lee, Su-Yeon; Kim, Seon-Hong; Hong, Chang-Young; Park, Se-Yeong; Choi, In-Gyu, Biotransformation of (-)-α-pinene and geraniol to α-terpineol and p-menthane-3,8-diol by the white rot fungus, Polyporus brumalis, 2015, JOURNAL OF MICROBIOLOGY
[170] Hodisan, Sorin; Pop Maghiar, Ramona; Groze, Alina; Ganea, Mariana; Stanasel, Oana, CARACTERISATION OF ORIGANUM VULGARE EXTRACTS, 2023, STUDIA UNIVERSITATIS BABES-BOLYAI CHEMIA
[171] Deng, C.; Mao, Y.; Yao, N.; Zhang, X., Development of microwave-assisted extraction followed by headspace solid-phase microextraction and gas chromatography–mass spectrometry for quantification of camphor and borneol in Flos Chrysanthemi Indici, 2006, Analytica Chimica Acta
[172] Ye, Q.; Deng, C., Determination of Camphor and Borneol in Traditional Chinese Medicines by Microwave-assisted Extraction and Gas Chromatography with Flame Ionization Detector, 2008, Analytical Letters
[173] Lin, C.-Y.; Chang, T.-C.; Chen, Y.-H.; Chen, Y.-J.; Cheng, S.-S.; Chang, S.-T., Monitoring the dynamic emission of biogenic volatile organic compounds from Cryptomeria japonica by enclosure measurement, 2015, Atmospheric Environment
[174] Michałowicz, J.; Duda, R.O.W., ANALYSIS OF CHLOROPHENOLS, CHLOROCATECHOLS, CHLORINATED METHOXYPHENOLS AND MONOTERPENES IN COMMUNAL SEWAGE OF ŁÓDŹ AND IN THE NER RIVER IN 1999–2000, 2005, Water, Air, and Soil Pollution
[175] Kohl, K.D.; Pitman, E.; Robb, B.C.; Connelly, J.W.; Dearing, M.; Forbey, J.S., Monoterpenes as inhibitors of digestive enzymes and counter-adaptations in a specialist avian herbivore, 2015, Journal of Comparative Physiology B: Biochemical, Systemic, and Environmental Physiology
[176] Li, R.; Wang, J.; Han, Y.; Dai, Z., Compound Danshen Yeast 1.0, 2024, Science of Traditional Chinese Medicine
[177] Hou, Chen; He, Boxiang; Xie, Peiwu; Wang, Yingli; Liang, Dongcheng; Lian, Huiming; Zhang, Qian; Cai, Yanling, Disentangling the Potential Functions of miRNAs in the Synthesis of Terpenoids during the Development of Cinnamomum burmannii Leaves, 2023, FORESTS
[178] Lei, Dengwei; Qiu, Zetian; Wu, Jihua; Qiao, Bin; Qiao, Jianjun; Zhao, Guang-Rong, Combining Metabolic and Monoterpene Synthase Engineering for de Novo Production of Monoterpene Alcohols in Escherichia coli, 2021, ACS SYNTHETIC BIOLOGY
[179] da Silva, Marcio Jose; Andrade, Pedro Henrique da Silva; Silva, Tiago Almeida; Diniz, Mariana Beatriz Teixeira; Ferreira, Sukarno Olavo; da Silva, Rene Chagas; de Araujo, Eduardo Nery Duarte, Evaluation of the Activity of Potassium Dodecatungstate Salts in Alcohol Oxidation Reactions: Cobalt(II), Cobalt(III), or Silicon(IV) as the Heteroatom, 2024, CATALYSIS LETTERS
[180] Weber, E.; Korkas, P.P.; Czugler, M.; Seichter, W., Synthesis and Crystalline Inclusion Behavior of New Dumb-Bell-Shaped Hosts, 2004, Supramolecular Chemistry
[181] Sarker, L.S.; Galata, M.; Demissie, Z.A.; Mahmoud, S.S., Molecular cloning and functional characterization of borneol dehydrogenase from the glandular trichomes of Lavandula x intermedia, 2012, Archives of Biochemistry and Biophysics
[182] Polichuk, D.R.; Zhang, Y.; Reed, D.W.; Schmidt, J.F.; Covello, P.S., A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua, 2010, Phytochemistry
[183] Nano, G.M.; Binello, A.; Cravotto, G.; Bianco, M.A., Biotransformation of (−)-bornyl acetate using submerged cultures of Collybia velutipes, Trametes hirsuta and Ganoderma applanatum, 2005, Journal of Chemical Technology and Biotechnology
[184] Roth, Steffen; Funk, Irina; Hofer, Michael; Sieber, Volker, Chemoenzymatic Synthesis of a Novel Borneol-Based Polyester, 2017, CHEMSUSCHEM
[185] Lin, Alison Li; Shangari, Nandita; Chan, Tom S.; Remirez, Diadelas; O'Brien, Peter J., Herbal monoterpene alcohols inhibit propofol metabolism and prolong anesthesia time, 2006, LIFE SCIENCES
[186] Dong, Xu; Liu, Yu; Fan, Junwen; Wang, Guoguang; Fan, Weijia; Wang, Haixia, Systematic characterization of the influence of petroleum spill on terpene metabolism in Suaeda salsa (L.) Pall from coastal wetland: Implication by compound-specific stable isotope, 2024, ENVIRONMENTAL POLLUTION
[187] Fenyvesi, E.; Zemlényi, C.; Orgoványi, J.; Oláh, E.; Szente, L., Can conversion mixture substitute beta-cyclodextrin in encapsulation of essential oils and their components?, 2016, Journal of Inclusion Phenomena and Macrocyclic Chemistry
[188] Martella, Noemi; Colardo, Mayra; Sergio, William; Petraroia, Michele; Varone, Michela; Pensabene, Daniele; Russo, Miriam; Di Bartolomeo, Sabrina; Ranalli, Giancarlo; Saviano, Gabriella; Segatto, Marco, Lavender Essential Oil Modulates Hepatic Cholesterol Metabolism in HepG2 Cells, 2023, CURRENT ISSUES IN MOLECULAR BIOLOGY
[189] Istifli, Erman Salih; Tepe, Arzuhan Sihoglu; Sarikurkcu, Cengiz; Tepe, Bektas, Interaction of certain monoterpenoid hydrocarbons with the receptor binding domain of 2019 novel coronavirus (2019-nCoV), transmembrane serine protease 2 (TMPRSS2), cathepsin B, and cathepsin L (CatB/L) and their pharmacokinetic properties, 2020, TURKISH JOURNAL OF BIOLOGY
[190] He T, Li X, Wang X, Xu X, Yan X, Li X, Sun S, Dong Y, Ren X, Liu X, Wang Y, Sui H, Xia Q, She G., Chemical composition and anti-oxidant potential on essential oils of Thymus quinquecostatus Celak. from Loess Plateau in China, regulating Nrf2/Keap1 signaling pathway in zebrafish, 2020, Sci Rep
[191] Khan S, Abdo AAA, Shu Y, Zhang Z, Liang T., The Extraction and Impact of Essential Oils on Bioactive Films and Food Preservation, with Emphasis on Antioxidant and Antibacterial Activities—A Review, 2023, Foods
[192] Ahmad A, van Vuuren S, Viljoen A., Unravelling the Complex Antimicrobial Interactions of Essential Oils — The Case of Thymus vulgaris (Thyme), 2014, Molecules
[193] Nakatsu Xc, T.; Lupo, A.T.; Chinn, J.W.; Kang, R.K.L., BIOLOGICAL ACTIVITY OF ESSENTIAL OILS AND THEIR CONSTITUENTS, 2000, Studies in Natural Products Chemistry
[194] Das, Sourav; Gazdag, Zoltan; Szente, Lajos; Meggyes, Matyas; Horvath, Gyorgyi; Lemli, Beata; Kunsagi-Mate, Sandor; Kuzma, Monika; Koszegi, Tamas, Antioxidant and antimicrobial properties of randomly methylated β cyclodextrin - captured essential oils, 2019, FOOD CHEMISTRY
[195] Ephrem, Elissa; Najjar, Amal; Charcosset, Catherine; Greige-Gerges, Helene, Selection of nerolidol among a series of terpenic and phenolic compounds for its potent activity against Lactobacillus fermentum ATCC 9338, 2019, PROCESS BIOCHEMISTRY
[196] Cheng, S.-S.; Lin, C.-Y.; Gu, H.-J.; Chang, S.-T., Antifungal Activities and Chemical Composition of Wood and Leaf Essential Oils from Cunninghamia konishii, 2011, Journal of Wood Chemistry and Technology
[197] Zhao, T.; Fan, G.; Tai, Y.; Shu, X.; Tian, F.; Zou, S.; Wu, Q., Chemical characterization, antioxidant, antimicrobial, enzyme inhibitory and cytotoxic activities of Illicium lanceolatum essential oils, 2024, Arabian Journal of Chemistry
[198] Gharred, N.; Ali, L.M.A.; Bettache, N.; Dridi-Dhaouadi, S.; Morère, A.; Menut, C., In Vitro Anti-inflammatory Activity of Three Inula Species Essential Oils in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages, 2023, Chemistry Africa
[199] Wang, Ran; Wu, Zhimin; Yang, Shufang; Guo, Shujuan; Dai, Xingxing; Qiao, Yanjiang; Shi, Xinyuan, A Molecular Interpretation on the Different Penetration Enhancement Effect of Borneol and Menthol towards 5-Fluorouracil, 2018, INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
[200] Zhang, T.; Shen, Q.; Pan, W., LC Determination of the Intestinal Absorption of Etoposide in Vitro and in Rat Plasma, 2010, Chromatographia
[201] Fan X, Chai L, Zhang H, Wang Y, Zhang B, Gao X., Borneol Depresses P-Glycoprotein Function by a NF-κB Signaling Mediated Mechanism in a Blood Brain Barrier in Vitro Model, 2015, Int J Mol Sci
[202] Wang S, Zhang D, Hu J, Jia Q, Xu W, Su D, Song H, Xu Z, Cui J, Zhou M, Yang J, Xiao J., A clinical and mechanistic study of topical borneol‐induced analgesia, 2017, EMBO Mol Med
[203] Jung, W.-C.; Jang, Y.-S.U.; Hieu, T.T.; Lee, C.-K.; Ahn, Y.-J., Toxicity of Myristica fragrans Seed Compounds Against Blattella germanica (Dictyoptera: Blattellidae), 2007, Journal of Medical Entomology
[204] Ishii, Y.; Iida, N.; Miyauchi, Y.; Mackenzie, P.I.; Yamada, H., Inhibition of Morphine Glucuronidation in the Liver Microsomes of Rats and Humans by Monoterpenoid Alcohols, 2012, Biological and Pharmaceutical Bulletin
[205] Cahusac PMB, Veermalla A., Effects of camphor and related compounds on slowly adapting mechanoreceptors in the rat sinus hair follicle, 2022, IBRO Neurosci Rep
[206] Saad, N.Y.; MULLER, C.D.; Lobstein, A., Major bioactivities and mechanism of action of essential oils and their components, 2013, Flavour and Fragrance Journal