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| 1.19 | The title is: Borneol: Antimicrobial and Antibacterial Applications and Mechanistic Insights |
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Title: Borneol: Antimicrobial and Antibacterial Applications and Mechanistic Insights
不同植物精油中龙脑的含量分布及抗菌活性特征
不同植物精油中龙脑的含量分布及影响因素
不同植物精油中龙脑的含量分布及影响因素
龙脑（borneol）作为一种具有抗菌活性的含氧单萜类化合物，广泛存在于多种植物精油中，其含量因植物种类、品种、提取方法、生长阶段、采收时间及环境处理等因素存在显著差异。
一、不同植物精油中龙脑的含量分布
多种植物精油中已检测到龙脑成分，且含量差异较大，具体分布如下表所示：
主要植物精油中龙脑的含量分布
| 植物种类/部位/处理 | 龙脑含量（%） | 备注 | 参考文献 |
|---|---|---|---|
| 欧蓍草（Achillea millefolium L.） | 12.4 | 精油主要成分之一 | [1] |
| 百里香属T. satureioides | 0 < % < 27.7 | 含量范围 | [2] |
| 百里香属T. pallidus | 1.4 < % < 25.6 | 含量范围 | [2] |
| 百里香属T. satureioides Coss | 21.56 | 精油成分 | [3] |
| 百里香属T. satureioides Coss水提取物（HE） | 25.04 | 高于精油（21.56%） | [3] |
| H. chrysotricha | 32.7 | 精油主要成分之一 | [4] |
| 薰衣草（Lavandula sp.） | 5.34 | 中等含量成分 | [5] |
| 苍耳（Xanthium strumarium） | 11.6 | 精油主要成分之一 | [6] |
| 长梗南五味子（Kadsura longipedunculata） | 6.05 | 精油成分 | [6] |
| 菊蒿（Achillea odorata subsp. pectinata） | 11.33 | 主要含氧单萜成分 | [7] |
| 欧蓍草（Achillea coarctata）茎精油 | 7.4 | 茎部位含量 | [8] |
| 欧洲艾蒿（Artemisia herba-alba） | 3.3 | 精油成分 | [9] |
| 桉属植物EO 3 | 5.80（(+)-龙脑） | 可能与环境相关 | [10] |
| 薄荷属Satureja macrosiphonia（Poldokhtar地区） | 16.60 | 采集地点差异 | [11] |
| 薄荷属Satureja macrosiphonia（Kabirkooh地区） | 8.20 | 采集地点差异 | [11] |
| 百里香属Thymus satureioides | 18.1 | 精油成分 | [12] |
| 精油分馏组分（RF=0.4） | 10.52 | 分馏富集 | [13] |
| 樟科植物（可能为肉桂或类似） | 2.67 | 精油成分 | [13] |
| 某植物水溶胶 | 20.4 | 是精油中（5.0%）的4倍 | [14] |
| 蒿属Artemisia chamaemelifolia（Kandovan种群开花前） | 13.50 | 生长阶段差异 | [15] |
| 普通艾蒿（Artemisia vulgaris）叶精油 | 8.06 | 叶部位含量 | [16] |
| 益智A11、A12品种 | 无显著差异 | 合成乙酸龙脑酯和樟脑的前体 | [17] |
| 迷迭香（Rosmarinus officinalis）超临界CO₂提取 | 18.79 | 提取方法差异（高于HD的8.52%、OM的3.75%） | [18] |
| 迷迭香（Rosmarinus officinalis） | 10.39 | 精油成分 | [19] |
| 迷迭香（Rosmarinus officinalis） | 7.7 | 精油成分 | [20] |
| 墨西哥刺木（Poliomintha barbatus） | 20.7 | 第二大成分 | [21] |
| 薰衣草（Lavandula angustifolia） | 8.29 | 与桉叶素、樟脑共同为主要成分 | [22] |
| 薰衣草（Lavandula angustifolia）叶状茎精油 | 13.0–19.7 | 部位含量范围 | [23] |
| 薰衣草（L. angustifolia） | 4.2 | 品种差异（低于杂交品种lavandin的6.1%） | [24] |
| 薰衣草花精油（某批次） | 0.41 | 批次差异 | [25] |
| 薰衣草（LA）2019年 | 15.67 | 年份差异（2020年为19.35%） | [26] |
| 柠檬桉（Corymbia citriodora） | 22.6（内型龙脑） | 精油成分 | [27] |
| 桉属植物 | 2.9 | 精油成分 | [28] |
| 百里香属Thymus satureioides | 34.26 | 主要成分之一 | [29] |
| 百里香属Thymus satureioides | 21.2 | 精油成分 | [30] |
| 摩洛哥百里香（T. maroccanus） | 0.2~16.3 | 盛花期后叶片达16.3% | [31] |
| 百里香属 | 1.44 | 精油成分 | [32] |
| 百里香属Thymus algeriensis | 23.48 | 精油成分 | [33] |
| 百里香属不同部位 | 0.7–4.7 | 部位含量范围 | [34] |
| 百里香属T. satureioides | 25.10 | 精油成分 | [35] |
| 伊朗杂交薰衣草（L. x intermedia） | 17.11–26.14 | 含量范围 | [24] |
| 犹太蒿（Artemisia judaica） | 5.72（内型龙脑） | 精油成分 | [36] |
| 蒿属植物 | 2.3~8.1 | 含量范围 | [37] |
| 土耳其A. gypsicola（花后全株） | 22.62 | 生长阶段差异 | [38] |
| 蒿属植物 | 6.1 | 精油成分 | [39] |
| Artemisia aucheri种子 | 检测到 | 种子精油成分 | [40] |
| Artemisia aragonensis | 13.20 | 精油成分 | [41] |
| 牛至（Origanum vulgare subsp. glandulosum）营养生长早期 | 2.38 | 生长阶段差异（晚期和花期未检测到） | [42] |
| 牛至精油OEO1 | 1.35 | 不同OEOs中最高（0.26–1.35%） | [43] |
| 药用鼠尾草（S. officinalis） | 7.6 | 与反式侧柏酮、樟脑共同为主要成分 | [44] |
| 百里香属Thymus satureioides | 合计43.9%（与α-松油醇） | 主要成分组合 | [45] |
| 牛至（Origanum vulgare L.） | 6.52 | 与香芹酚、邻伞花烃共同为主要成分 | [46] |
| 蒿属植物（可能为Artemisia sp.） | 6.2 | 樟脑烷衍生物合计占30.0% | [47] |
| Teucrium argyrophyllum var. argyrophyllum花 | 12.0 | 部位差异（茎为15.0%） | [48] |
| Teucrium argyrophyllum var. argyrophyllum茎 | 15.0 | 部位差异（花为12.0%） | [48] |
| 薄荷属/类似植物 | 2.11 | 精油成分 | [49] |
| 蒿属/类似植物 | 2.34 | 精油成分 | [50] |
| 樟科/类似植物 | 6.9 | 与樟脑、桉叶素共同为主要成分 | [51] |
| 牛至属/类似植物 | 3.1 | 精油成分 | [52] |
| 樟科/类似植物 | 15.0 | 与桉叶素、甲基丁香酚共同为主要成分 | [53] |
| 菊科/类似植物 | 2.11 | 精油成分 | [49] |
| 唇形科/类似植物 | 26.2 | 与乙酸龙脑酯、莰烯共同为主要成分 | [54] |
| 唇形科/类似植物（Cobar Peneplain生物区） | 31.7 | 环境差异 | [55] |
| 菊科/类似植物 | 花期降低 | 生长阶段差异 | [56] |
| 马郁兰相关精油 | 1.9 | 精油成分 | [57] |
| Marrubium cristata subsp. phrygia | 26.9、31.4、39.3 | 所有样品均为主要成分 | [58] |
| 艾纳香（Artemisia argyi） | 58.7 mg/g | 精油含量（单位：mg/g） | [59] |
| Cupressus ornifolia | 2.9 | 精油成分 | [28] |
| Poldokhtar精油 | 7.1 | 精油成分 | [60] |
| A. grandifolia | 5.2 | 精油成分 | [61] |
| T. macrophyllum | 9.1 | 精油成分 | [61] |
| 药用鼠尾草（S. officinalis）海拔100 m | 5.0 | 海拔差异（500 m为4.5%） | [62] |
| E. fimbriobracteata | 8.1 | 精油成分 | [63] |
| T. parthenium叶片 | 2.9 | 叶片精油成分 | [64] |
| T. punctatum叶片 | 2.1 | 叶片精油成分 | [64] |
| S. veneris | 6.2 | 精油成分 | [65] |
| S. pachystachys | 含龙脑成分 | 与spathulenol共同形成抑菌带 | [66] |
| 精油分馏组分IV | 62.3 | 分馏富集（含量最高） | [67] |
| Thymus polium冬季样品 | 8.24 | 季节差异（秋季未检测到） | [68] |
| Teucrium arduini地上部干物质 | 5.4 | 精油成分 | [69] |
| 某植物精油 | 10.8 | 精油成分 | [70] |
| Xylopia hypolampra茎皮 | 7.8 | 茎皮精油成分 | [71] |
| Gori和Jord品种 | 0.6–14.6 | 品种含量范围 | [72] |
| Satureja bachtiarica Bunge | 13.4 | 精油成分 | [73] |
| 某植物精油 | 主要含樟脑、龙脑等 | 检测到51种挥发性成分 | [74] |
| 精油SlEO-3 | 较高 | 含量较高 | [75] |
二、龙脑含量的影响因素
龙脑含量受多种因素综合调控，具体如下：
- 植物种类与品种：不同植物及品种的龙脑含量差异显著，如H. chrysotricha精油中龙脑含量高达32.7%[4]，而薰衣草精油中仅为5.34%[5]；益智A11和A12品种的龙脑含量无显著差异[17]。
- 植物部位与处理：同一植物不同部位含量不同，如Teucrium argyrophyllum var. argyrophyllum花精油龙脑含量为12.0%，茎精油为15.0%[48]；分馏处理可富集龙脑，如某精油分馏组分IV中龙脑含量达62.3%[67]。
- 提取方法：不同方法提取的龙脑含量差异显著，如迷迭香精油中超临界CO₂提取法的龙脑含量（18.79%）高于水蒸气蒸馏法（8.52%）和有机溶剂法（3.75%）[18]；微波辅助水蒸气蒸馏法（MAHD）提取的Satureja macrosiphonia精油龙脑含量高于其他方法[11]。
- 生长阶段与采收时间：植物生长阶段影响龙脑积累，如Artemisia chamaemelifolia Kandovan种群开花前龙脑含量最高（13.50%）[15]，牛至营养生长晚期和花期未检测到显著龙脑含量[42]。
- 环境与地理因素：地理环境导致含量差异，如Satureja macrosiphonia精油中龙脑含量在Poldokhtar地区为16.60%，Kabirkooh地区为8.20%[11]；Cobar Peneplain生物区采集的唇形科植物精油龙脑含量高达31.7%[55]。
- 对映体组成：龙脑的对映体组成随季节略有变化，某植物精油中(S)-型为主要对映体[14]。
三、龙脑含量与抗菌活性的关联
龙脑是植物精油抗菌活性的重要贡献者，其含量与抗菌活性存在一定关联：
- 欧蓍草花部精油因龙脑含量更高，抗菌和抗真菌活性强于叶片[1]；
- 百里香属T. satureioides和T. pallidus精油中龙脑含量变化显著影响抗菌活性[2]，T. satureioides Coss水提取物（龙脑25.04%）对革兰氏阳性和阴性菌株均有强抗菌作用[3]；
- H. chrysotricha精油（龙脑32.7%）对革兰氏阳性菌具有强抑制作用，且与链霉素具有协同抗菌潜力[4]；
- 苍耳精油（龙脑11.6%）对金黄色葡萄球菌等的MIC值低至0.5±0.1 µg/mL[6]；
- 含高龙脑的精油（如26.2%、31.7%）可通过损伤细菌细胞膜、细胞壁等发挥抗菌作用，MIC值低至5 mg/mL[54][55]；
- 龙脑与其他成分（如α-松油醇、樟脑）协同可增强抗菌活性，如Thymus satureioides精油中两者合计占43.9%，对多种细菌的MIC值为2–4 µL/mL[45]。
综上，龙脑在植物精油中的含量分布受多因素调控，且其含量与精油抗菌活性密切相关，为龙脑的开发利用提供了理论基础。
龙脑对革兰氏阳性菌和革兰氏阴性菌的抗菌活性特征
龙脑：抗菌应用及机制解析——不同植物精油中龙脑的含量分布及抗菌活性特征
一、不同植物精油中龙脑的含量分布
龙脑作为含氧单萜类化合物，广泛存在于多种植物精油中，其含量因植物种类、产地、部位、生长阶段及提取方法而异。不同科属植物精油中龙脑的含量分布及相关特征如下表所示：
不同科属植物精油中龙脑的含量分布及特征
| 科属分类 | 植物种类 | 龙脑含量/特征 | 参考文献 |
|---|---|---|---|
| 唇形科 | Thymus satureioides | Tata和Azrou产地种群含量最高，分别为41.3%、31.7%；其他种群含量为21.2%、25.10%、27%、18.1%、34.26% | [76][77][30][35][12][29] |
| Thymus maroccanus | 0.2%~16.3%，花后期叶片含量达16.3% | [31] | |
| Thymus leptobotrys | 2.7% | [67] | |
| 普通百里香 | 1.44% | [32] | |
| Thymus属某植物 | 0.7%~4.7% | [34] | |
| Thymus polium | 冬季采收含量为8.24%，秋季未检测到 | [68] | |
| Lavandula angustifolia | 8.29%（第三大优势成分）；叶状茎精油13.0%~19.7%；LA 2019/2020为15.67%/19.35%；与杂薰衣草精油含量分别为4.2%/6.1% | [22][23][26][24] | |
| 薰衣草栽培品种（‘Alba’等） | 含量高于L. angustifolia | [78] | |
| Satureja lavandulifolia | 1%~8% | [79] | |
| Rosmarinus officinalis | 26.48%（首要成分）；10.39% | [80][19] | |
| Rosmarinus beesianus | 15.0%（第二大主要成分，仅次于1,8-桉叶素47.6%） | [53] | |
| Salvia officinalis | 5%~4.5%（100m海拔含量高于500m）；7.6%（第三丰富成分） | [62][44] | |
| Salvia veneris | 6.2% | [65] | |
| Satureja pachystachys | 活性组分中占68.9% | [66] | |
| Satureja montana | 主要成分之一（与γ-松油醇、香芹酚共为主要成分） | [81] | |
| Satureja macrosiphonia | 主要含氧单萜之一，微波辅助水蒸馏（MAHD）法含量高于传统水蒸馏（HD）法 | [11] | |
| Teucrium arduini | 地上部分干燥材料精油含量为5.4% | [69] | |
| Teucrium argyrophyllum var. argyrophyllum | 花精油12.0%，茎精油15.0%，均为主要成分之一 | [48] | |
| 菊科 | Artemisia judaica | endo-龙脑含量5.72%（主要成分之一） | [36] |
| Artemisia属多种植物（A. annua等） | 2.3%~8.1% | [37] | |
| Artemisia gypsicola | 花后期含量达22.62% | [38] | |
| Artemisia属某植物（类型III） | 2.6% | [82] | |
| Artemisia属某植物 | 6.1%；10.8%；13.20% | [39][70][41] | |
| Achillea millefolium | 印度德里种群含量12.4%（主要成分之一）；可通过柱层析分离得到 | [1][83] | |
| Achillea coarctata | 茎精油含量7.4%（主要成分之一） | [8] | |
| Artemisia vulgaris | 叶精油含量8.06%（主要成分之一） | [16] | |
| Artemisia canescens | 6.9%（主要成分之一） | [51] | |
| Tanacetum parthenium | 2.9%，开花期含量较前期降低 | [64][56] | |
| 其他科属 | Combretum spp.（使君子科） | 叶提取物中相对丰富，与桉叶素等抗菌单萜共存 | [84] |
| Curcuma wenyujin（姜科） | PJH精油典型成分之一 | [85] | |
| Satureja satureioides | 12.4%（第三大优势成分） | [86] | |
| Xylopia hypolampra（番荔枝科） | 茎皮精油含量7.8% | [71] | |
| Xanthium strumarium（菊科） | 11.6%（主要成分之一） | [6] | |
| Helenium chrysotricha（菊科） | 优势成分，含量高达32.7% | [4] | |
| 茄属植物（SlEO-3） | 含量较高，以(-)-对映异构体为主 | [75] | |
| Origanum vulgare L.（唇形科） | 6.52%（第二大主要成分，仅次于香芹酚50.26%） | [46] |
二、龙脑对革兰氏阳性菌和革兰氏阴性菌的抗菌活性特征
龙脑的抗菌活性具有菌株选择性，且常与精油中其他成分协同发挥作用，其对革兰氏阳性菌的敏感性显著高于革兰氏阴性菌。
革兰氏阳性菌的敏感性：龙脑对革兰氏阳性菌抑制活性较强，纯龙脑的MIC为0.05~3.2 mg/ml[87]。含龙脑的精油对多种革兰氏阳性菌表现出显著抑制作用，如Thymus satureioides精油对S. aureus的MIC为0.25%[86]，对M. luteus和B. cereus的抑菌圈直径大于20 mm[12]；Satureja pachystachys精油对S. aureus的MIC为1.25 mg/mL[66]；Artemisia gypsicola精油对革兰氏阳性菌的抑菌圈直径达37.3 mm[38]；Xanthium strumarium精油对S. aureus的MIC为0.5±0.1 μg/mL[6]。此外，龙脑与其他成分的协同作用可增强抗菌活性，如迷迭香精油中龙脑与樟脑、马鞭草酮协同抑制无害李斯特菌[88]，温郁金PJH精油中龙脑与桉叶素、樟脑协同提升抗菌活性[85]。
革兰氏阴性菌的抑制活性：龙脑对革兰氏阴性菌的活性相对较弱，但仍具有一定作用。纯龙脑对K. pneumoniae的MIC为0.47 mg/L[89]；含龙脑的精油如Achillea millefolium分离龙脑对E. coli的MBC为2.5±0.08 μg/mL[83]，Xanthium strumarium精油对K. pneumoniae的MIC为4.8±0.0 μg/mL[6]。部分研究显示龙脑与其他成分协同可增强对革兰氏阴性菌的活性，如Artemisia属提取物中富含龙脑的YSF组分对H. pylori的MIC为0.08 mg/mL，强于YE组分的0.14 mg/mL[90]。
协同作用与机制：龙脑的抗菌活性常依赖与其他成分的协同，如Satureja lavandulifolia精油中龙脑与桉叶素、樟脑协同[79]，Satureja pachystachys精油中龙脑与spathulenol协同[66]。其抗菌机制可能与形成氢键的能力有关[41]，且被偏最小二乘法（PLS）模型确定为与精油抗菌活性相关的重要化合物（VIP>1）[85]。此外，季节、采收部位及提取方法等因素会通过影响龙脑含量调控精油抗菌效力，如Thymus polium冬季精油龙脑含量高且抗菌活性强于秋季[68]，Achillea millefolium花部精油龙脑含量高于叶部且抗菌活性更强[1]，Satureja macrosiphonia MAHD法提取精油龙脑含量更高且抗菌活性更强[11]。
三、小结
龙脑广泛存在于唇形科、菊科等多科属植物精油中，含量差异显著（0.2%~41.3%），且对革兰氏阳性菌的抑制活性强于革兰氏阴性菌。作为精油抗菌活性的关键贡献者，龙脑不仅自身具有抗菌活性，还常与其他成分协同增强效力，其含量受植物种类、生长阶段、提取方法等因素调控，进而影响精油的抗菌效力。此外，龙脑对真菌（如白色念珠菌）和酵母菌也具有抑制活性[91][75]，且在耐药菌株（如MRSA、ESBL阳性菌）感染防治中展现出潜力[84]，为其在食品防腐、临床抗感染等领域的应用提供了理论依据。
龙脑在精油抗菌作用中的协同效应与独立贡献
龙脑：抗菌及抑菌应用与机制研究——不同植物精油中龙脑的含量分布及抗菌活性特征——龙脑在精油抗菌作用中的协同效应与独立贡献
龙脑作为含氧单萜类化合物，广泛存在于多种植物精油中，其含量因植物种类、提取部位、产地及萃取方法而异，且含量差异可能直接影响精油的抗菌活性特征[76][92][18][93][57][28][33][94][23][25][95][54][1][4]。不同植物精油中龙脑的含量分布如下：
不同植物精油中龙脑的含量分布
| 植物种类/精油类型 | 龙脑含量 | 补充说明 | 参考文献 |
|---|---|---|---|
| 百里香属植物（Thymus satureioides）精油 | 0.3%–41.3% | Tata产地（41.3%）、Azrou产地（31.7%），为仅次于香芹酚的主要成分 | [76] |
| 四翅崖柏（Tetraclinis articulate）精油 | 14.83% | 第三丰富的单萜衍生物，仅次于樟脑（28.48%）和乙酸龙脑酯（18.91%） | [92] |
| 迷迭香精油（超临界CO₂萃取物） | 18.79% | 含量最高 | [18] |
| 迷迭香精油（有机溶剂萃取物OM） | 3.75% | 含量最低 | [18] |
| 粘叶鱼藤（D. viscosa）叶精油 | 9.3% | 第二丰富的成分 | [93] |
| Algerian百里香（T. algeriensis）精油 | 23.48% | 与芳樟醇、莰烯等共同构成主要成分 | [33] |
| C. urucurana茎皮精油 | 14.7% | — | [94] |
| 樟科植物（C. ornifolia）精油 | 2.9% | — | [28] |
| 桉树精油 | 检出 | — | [96] |
| 薰衣草相关精油（LVO） | 1.9% | 含量较低 | [57] |
| 薰衣草花精油 | 0.41% | — | [25] |
| Lavandula angustifolia叶状茎精油 | 13.0–19.7% | — | [23] |
| 鼠尾草属植物精油 | 2.12–18.38% | — | [95] |
| 某未明确植物精油 | 26.2% | — | [54] |
| 千叶蓍（A. millefolium L.）精油 | 12.4% | 主要成分为桧烯（17.5%）、1,8-桉叶素（13%）、龙脑（12.4%）等 | [1] |
| H. chrysotricha精油 | 32.7% | 最主要成分，其次为芳樟醇（7.5%）、甲酸异龙脑酯（5.4%）和α-松油醇（4.8%） | [4] |
此外，植物部位差异也会影响龙脑含量及抗菌活性：千叶蓍花部精油因樟脑、龙脑和α-杜松醇含量更高，其抗菌和抗真菌活性强于叶部精油[1]。
龙脑的抗菌活性已得到多项研究证实，其对革兰氏阳性菌、革兰氏阴性菌及真菌的抑制作用机制包括：作为亲脂性化合物插入细菌细胞膜，改变膜通透性导致细胞内容物泄漏[76][92]；与异亮氨酰-tRNA合成酶（PDB ID: 1JZQ）结合，干扰细菌蛋白质生物合成[97]；在某些精油体系中诱导微生物细胞内活性氧（ROS）过量产生[91]。具体活性特征如下：对单核细胞增生李斯特菌（L. innocua）的抑菌圈为1–2 mm，最低抑菌浓度（MIC）为5 mg/ml[88]；仅对金黄色葡萄球菌（S. aureus）、粪肠球菌（E. faecalis）等革兰氏阳性菌有活性，对革兰氏阴性菌无明显抑制作用[98]；亚抑菌浓度下可抑制细菌黏附能力及毒力因子表达[99]。含量较高的龙脑往往与更强的抗菌活性相关，例如H. chrysotricha精油因高含量龙脑对革兰氏阳性菌表现出强烈抑制作用[4]；化学计量学分析指出，S. kitaibelii精油11月样品的抗菌活性主要由龙脑、匙叶桉油烯醇、石竹烯氧化物和柠檬烯共同贡献，且比例对活性至关重要[100]。
龙脑在精油抗菌作用中常与其他成分协同发挥功效：百里香精油的抗菌活性与香芹酚、百里酚、龙脑等的协同作用相关[76]；四翅崖柏精油的抗菌活性归因于樟脑、乙酸龙脑酯、α-蒎烯和龙脑的共同作用[92]；C. ornifolia精油中龙脑与樟脑、α-葑醇等含氧单萜协同增强抑制效果[28]；D. viscosa叶精油中龙脑与乙酸龙脑酯等协同，对多种微生物的MIC范围为0.101 mg/mL至3.25 mg/mL[93]；T. algeriensis精油中龙脑与香芹酚协同，对革兰氏阳性菌的MIC < 0.5 µL/mL，对革兰氏阴性菌的MIC为1 µL/mL[33]；龙脑与芳樟醇共同对精油混合物的抗菌效果负责[101]；Lavandula angustifolia精油中龙脑与其他成分对金黄色葡萄球菌的协同作用指数（FICI）低至0.076[23]；薰衣草精油中龙脑等成分与恩诺沙星联用的协同作用占比达82.35%[25]；H. chrysotricha精油与链霉素具有协同抗菌潜力[4]。这些协同作用可能与龙脑与其他萜类、醇类成分共同破坏细胞膜结构、干扰细胞代谢通路有关[91][102]。
然而，龙脑的抗菌活性强度受含量及精油整体组成影响：纯化合物测试中，龙脑对金黄色葡萄球菌的抑制效果与水芹烯、樟脑相当[99]，但弱于香芹酚、莰烯[103]；迷迭香精油抗李斯特菌活性筛选中，龙脑抑制效果弱于马鞭草酮、樟脑、乙酸龙脑酯[88]；当龙脑含量较低时（如LVO中1.9%），对整体抗菌活性的贡献相对有限[57]；部分精油中因龙脑浓度低，直接贡献较小[98]。
综上，龙脑作为植物精油中的常见活性成分，通过直接破坏细胞膜、干扰蛋白质合成等机制发挥抗菌作用，并与其他萜类、酚类成分协同增强精油整体抗菌活性。其含量分布的多样性及抗菌机制的复杂性，为植物精油在食品防腐、临床抗感染等领域的应用提供了理论依据。
龙脑抗菌作用的潜在机制（膜破坏与分子相互作用）
龙脑：抗菌应用及机制研究进展
一、不同植物精油中龙脑的含量分布
龙脑作为含氧单萜类化合物，广泛存在于多种植物精油中，其含量因植物种类及产地而异。百里香属（Thymus）植物精油中龙脑为重要次要或主要成分，其他植物精油中也存在不同程度分布。主要植物精油的龙脑含量如下：
不同植物精油中的龙脑含量分布
| 植物精油（来源） | 龙脑含量 | 备注 | 参考文献 |
|---|---|---|---|
| 普通百里香样品精油 | 0.3%~41.3% | - | [76] |
| 摩洛哥Tata产Thymus satureioides精油 | 41.3% | 主要成分（仅次于香芹酚） | [76] |
| 摩洛哥Azrou产Thymus satureioides精油 | 31.7% | 主要成分（仅次于香芹酚） | [76] |
| Thymus vulgaris精油 | 76.42% | 最主要成分 | [97] |
| Artemisia aragonensis精油 | 13.20% | - | [41] |
| EOBD（植物未明确）精油 | 11.07% | - | [104] |
| I. graveolens精油 | 26.2% | 与乙酸龙脑酯（43.3%）为主要成分 | [54] |
| CbEO（植物未明确）精油 | 较低 | 或与抗菌活性不足相关 | [91] |
二、龙脑的抗菌活性特征
龙脑是植物精油发挥抗菌活性的重要分子。百里香属植物精油的抗菌活性与酚类、萜类化合物（含龙脑、香芹酚、百里酚等）密切相关[76]；Artemisia aragonensis精油中的龙脑被认为是其对革兰氏阳性菌（如B. subtilis、S. aureus）和革兰氏阴性菌（如E. coli）发挥显著抗菌作用的关键成分之一[41]。
龙脑单独或协同其他成分对耐药菌及真菌有效：EOBD精油中龙脑（11.07%）与芳樟醇、桉树脑等协同，对耐抗生素S. aureus（抑菌圈直径36.40±1.70 mm，MIC 10.78±1.28 μg/mL）和P. aeruginosa表现良好抗菌活性，对C. albicans的抑菌圈直径达36.79±1.35 mm，MIC为15.32±1.47 μg/mL[104]；CbEO中的龙脑也具有抗念珠菌和抗真菌活性[91]。此外，龙脑在亚抑菌浓度（MIC/2）下仍能抑制细菌对惰性底物的黏附，并降低可溶性毒力因子表达[99]。
三、龙脑抗菌作用的潜在机制
龙脑的抗菌机制主要涉及细胞膜破坏和分子相互作用：细胞膜破坏是核心机制，I. graveolens精油（含26.2%龙脑）处理S. aureus后，透射电镜显示细菌细胞膜内陷、细胞壁增厚、细胞质密度降低聚集，最终导致细胞死亡[54]，这可能与其脂溶性特征相关——脂溶性分子易穿透细胞壁和细胞膜，改变多糖、脂肪酸及磷脂结构，破坏膜通透性[104]。分子相互作用方面，龙脑可通过形成氢键增强对革兰氏阳性菌的活性[41]，还可能诱导微生物细胞内活性氧（ROS）过量产生[91]；分子对接研究显示，包括龙脑相关倍半萜（如β-石竹烯）在内的萜类成分对异亮氨酰-tRNA合成酶（PDB ID: 1JZQ）结合亲和力较高（-6.8~-7.0 kcal/mol），可能通过抑制细菌蛋白质合成关键酶发挥作用[97]。
综上所述，龙脑在多种植物精油中广泛分布，含量差异显著影响精油抗菌活性；其抗菌机制涉及细胞膜破坏、氢键形成及酶活性抑制等层面，为新型抗菌剂开发提供了重要理论依据。
龙脑与其他成分的协同抗菌作用及影响因素
龙脑与其他成分的协同抗菌作用及影响因素
龙脑（borneol）是一种广泛存在于多种植物精油中的双环单萜醇，单独使用时抗菌活性较弱（如对大肠杆菌的最低抑菌浓度（MIC）为0.5 μl/ml[105]，对多种细菌仅表现出弱抑制作用[106]），但与其他抗菌成分或抗生素组合时可产生显著协同效应，其机制可能与破坏细菌细胞膜、抑制外排泵活性有关——龙脑可穿透细菌膜并降低外排泵功能，从而提升低浓度强抗菌成分（如萜品烯-4-醇、柠檬烯、蒎烯、香芹酮、丁子香酚）的作用效果[107]。
不同植物精油中龙脑的相对含量
| 植物精油来源 | 龙脑相对含量 | 文献来源 |
|---|---|---|
| A. setacea | 32.97% | [107] |
| H. chrysotricha | 32.7% | [4] |
| M. communis L. | 27.15% | [108] |
| D. graveolens | 18.7% | [109] |
| L. angustifolia | 13.0–19.7% | [23] |
| T. satureioides | 未明确具体含量 | [110] |
| S. kitaibelii | 主要成分之一 | [100] |
一、龙脑与单萜类成分的协同作用
龙脑与单萜类化合物的协同作用主要通过破坏细菌细胞膜结构、促进龙脑或其他成分进入细胞实现。例如，γ-萜品烯和α-萜品烯可破坏细胞膜脂质双分子层导致脂质泄漏，从而增强龙脑的抗菌效果[106]；T. satureioides精油中的龙脑通过与香芹酚、百里香酚的协同效应，显著增强对细菌的生长抑制[110]；S. kitaibelii精油中龙脑与柠檬烯、斯巴醇、石竹烯氧化物的比例是影响其11月采收样品抗菌活性的关键因素[100]。
二、龙脑与抗生素的协同作用
龙脑所在的精油与抗生素组合时也常表现出协同效应。例如，D. graveolens精油（含18.7%龙脑）与氯霉素组合时，60.0%的测试组合表现出协同作用，对奇异变形杆菌（P. mirabilis ATCC 12453）的抑制效果最显著[109]；H. chrysotricha精油（含32.7%龙脑）与链霉素组合时显示出协同潜力[4]；L. angustifolia精油（含13.0–19.7%龙脑）与恩诺沙星组合时，82.35%的测试案例表现出强协同作用（FICI=0.155–0.375）[25]。
三、协同作用的影响因素
- 成分比例：协同效应依赖于龙脑与其他成分的比例。例如，γ-萜品烯或α-萜品烯在与龙脑的协同组合中需占较高比例[106]；L. angustifolia精油与恩诺沙星的协同作用中，两者浓度需调整至特定范围（如1/4 MIC的恩诺沙星与1/4 MIC的精油组合）[25]。
- 细菌种类：协同作用具有菌种特异性。例如，L. angustifolia精油中的龙脑协同作用对金黄色葡萄球菌（S. aureus）菌株更显著，对甲氧西林耐药金黄色葡萄球菌（MRSA）的协同作用FICI低至0.076[23]；T. vulgaris L.与M. communis L.精油（含27.15%龙脑）的组合对鼠伤寒沙门氏菌（S. typhimurium）表现出协同效应（FICI=0.498）[108]；D. graveolens精油与氯霉素的协同作用对P. mirabilis ATCC 12453效果最佳[109]。
- 精油整体组成：精油中多种成分的协同作用可能增强龙脑的效果。例如，S. kitaibelii精油中龙脑、柠檬烯、斯巴醇、石竹烯氧化物的相互比例是其抗菌活性的关键[100]；A. setacea精油中龙脑与桉叶素（14.94%）、樟脑（10.13%）等成分的协同作用可能是其抗菌活性的基础[107]；D. graveolens精油中龙脑与乙酸龙脑酯（21.7%）等成分的组合也参与协同抗菌[109]。
四、龙脑协同抗菌的应用潜力
龙脑的协同抗菌特性使其在抗菌材料开发中具有应用价值。例如，基于龙脑的聚合物涂层可通过水解释放龙脑，与樟脑协同发挥防污抗菌作用[111]；含龙脑的精油与抗生素组合可降低耐药菌的MIC——如薰衣草精油（含0.41%龙脑）与恩诺沙星组合对多重耐药菌的MIC显著降低[25]；H. chrysotricha精油（含32.7%龙脑）与链霉素的协同作用可增强对革兰氏阳性菌的抑制[4]。这些研究表明，龙脑通过与其他成分的协同作用可有效提升抗菌效率，为耐药菌控制和天然抗菌剂开发提供了新方向。
说明
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龙脑抗菌活性的作用机制及相关分子基础
龙脑：抗菌应用及作用机制研究进展
龙脑（borneol）是百里香属（Thymus）、鼠尾草属（Salvia）、迷迭香属（Rosmarinus）等植物精油中的核心活性成分，其含量因植物种类与产地存在显著差异。
不同植物精油中龙脑的含量分布
| 植物种类 | 龙脑含量 | 参考文献 |
|---|---|---|
| Thymus satureioides（不同产地） | 31.7%~41.3% | [76] |
| T. vulgaris（普通百里香） | 76.42% | [97] |
| Artemisia aragonensis | 13.20% | [41] |
| Rhynchostylis gigantea 变种EOBD | 11.07% | [104] |
| Rosmarinus beesianus | 15.0% | [112] |
这些精油的抗菌活性被认为与龙脑等萜类化合物密切相关[76][97]。
抗菌与抗真菌活性
龙脑对革兰氏阳性菌、革兰氏阴性菌及真菌均具有抑制作用：在纯化合物测试中，其对金黄色葡萄球菌（S. aureus）、铜绿假单胞菌（P. aeruginosa）的抑制效果与香芹烯、樟脑相当[99]；对肺炎链球菌（S. pneumoniae）敏感性较强，但对化脓性链球菌（S. pyogenes）相对耐药[113]；同时可抑制白色念珠菌（C. albicans）、热带念珠菌（C. tropicalis）及红色毛癣菌（T. rubrum）、犬小孢子菌（M. canis）等皮肤癣菌[114][113][104]。值得注意的是，龙脑在亚抑菌浓度（MIC/2）下即可抑制细菌对惰性基质的黏附，并下调可溶性毒力因子表达[99]。
龙脑的抗菌活性受浓度及协同作用调控：0.005%浓度下对白色念珠菌生物膜形成的抑制率超80%[114]，但精油中龙脑浓度较低时可能减弱整体抗菌活性[91]；与γ-松油烯或α-松油烯联用时，对白色念珠菌和热带念珠菌表现出协同抑制作用[106]。此外，龙脑衍生物也具有抗菌活性，如通过ZnBr₂催化和微波辅助Ferrier反应制备的2,3-不饱和葡萄糖苷衍生物（6b），处理金黄色葡萄球菌悬浮液10小时后浊度降低58%，显示缓慢溶菌效果[115]。
作用机制
龙脑的抗菌机制以直接干扰细菌结构与功能为主：作为脂溶性化合物，其可穿透细胞膜脂多糖层，改变膜结构与通透性，导致细胞内离子梯度紊乱及关键分子泄漏，最终引起细胞死亡[104][116][112]（如与柠檬醛联用时可增加李斯特菌和铜绿假单胞菌细胞膜孔隙率[117]）；同时可通过分子对接与细菌关键酶（如异亮氨酰-tRNA合成酶）结合，干扰蛋白质合成等代谢过程[97]。
针对细菌酪氨酸-tRNA合成酶（TyrRS）的分子对接显示，龙脑（CID 64685）可与TyrRS的甘氨酸（GLY 47）和丙氨酸（ALA 51）残基形成氢键，稳定复合物结构并影响酶催化活性，干扰氨基酸酰化过程[118]；其衍生物6b的溶菌活性进一步支持细胞膜破坏机制[115]。抗真菌机制可能涉及线粒体呼吸抑制及膜通透性改变[104]，同时（-）-龙脑可激活人中性粒细胞、调控炎症反应，通过宿主免疫间接发挥抗菌作用[113]。
分子靶点与结构基础
龙脑的作用靶点涉及多种蛋白质：分子对接显示其与人类碳酸酐酶I、II、IV（结合概率36%）及瞬时受体电位阳离子通道M8亚型（TRPM8，结合概率31%）具有较高亲和力[119]，但与抗菌机制的关联需进一步研究。在抗菌相关靶点中，龙脑与细菌TyrRS的氢键作用具有结构特异性，其羟基位置等结构特征与其靶点结合能力密切相关，且结合模式与樟脑、α-蒎烯等其他萜类化合物不同[118]。
综上，龙脑通过直接破坏细胞膜、抑制酶活性及调节宿主免疫等多途径发挥抗菌作用，其衍生物活性及与细菌TyrRS的分子相互作用为新型天然抗菌剂开发提供了理论基础。
龙脑在不同应用场景中的抗菌性能表现
龙脑在不同应用场景中的抗菌性能表现
龙脑作为多种植物精油的核心成分，其抗菌活性受含量、协同成分、作用对象及应用场景的综合调控，在细菌/真菌抑制、生物膜防控、尘螨驱杀及食品防腐等领域均展现出潜在价值。以下通过整合不同植物精油中龙脑的含量及其对应的抗菌指标，系统呈现其活性特征：
不同植物精油中龙脑含量与抗菌活性对比
| 植物精油来源 | 龙脑含量 | 抗菌/抗真菌对象 | 主要活性指标（MIC/MBC/MFC等） | 参考文献 |
|---|---|---|---|---|
| P. barbatus | 20.7% | 多数微生物 | MIC：0.137–0.55 mg/mL；MBC/MFC均为MIC的1倍 | [21] |
| T. algeriensis | 23.48% | 革兰氏阳性菌（S. aureus、L. monocytogenes EGD-e）、革兰氏阴性菌（S. enteritidis、E. coli） | 革兰氏阳性菌MIC < 0.5 µL/mL、MBC 0.5 µL/mL；革兰氏阴性菌MIC 1–2 µL/mL、MBC更高 | [33] |
| 迷迭香（R. officinalis） | 10.39% | 白色念珠菌 | 强抗真菌活性 | [19] |
| Thymus satureioides | 21.2% | 微生物 | MIC低至0.15 mg/mL；抑菌圈直径30.3 ± 0.02 mm | [30] |
| R. beesianus | 15.0% | S. aureus、Enterococcus faecalis、B. subtilis等 | MIC：3.13–6.25 mg/mL；MBC：6.25–12.50 mg/mL | [112] |
| A. judaica | 5.72%（endo-borneol） | S. aureus、E. coli、C. albicans | MIC：0.5、1.0、1.0 μL/disc | [36] |
| T. maroccanus（花期后叶片） | 16.3% | 念珠菌、细菌 | 念珠菌MIC：0.12–0.25 mg/mL；细菌MIC：1.18–2.37 mg/mL（中等活性） | [31] |
| X. hypolampra茎皮 | 7.8% | S. aureus、S. pyogenes、E. coli | MIC均>500 µg/mL（活性较弱） | [71] |
| Achillea odorata subsp. pectinata | 11.33% | B. subtilis | 抑菌圈直径31 ± 1 mm | [7] |
| O. vulgare subsp. glandulosum（早期营养期） | 2.38% | E. coli、S. typhimurium、P. aeruginosa、B. subtilis | MIC：E. coli/S. typhimurium 250 μg/mL；P. aeruginosa/B. subtilis 125 μg/mL | [42] |
| LA 2020 | 19.35% | 真菌菌丝体 | 15 µL用量可完全抑制体外生长 | [26] |
龙脑的抗菌活性还与植物提取阶段、部位及协同成分密切相关。例如，O. vulgare subsp. glandulosum精油的龙脑含量随物候期变化（早期营养期2.38%，花期未检出），但整体仍保持较高抗菌活性[42]；部分植物根精油因龙脑含量较高，对S. aureus、B. cereus等的抑菌效果优于其他部位[120]。龙脑与百里酚、香芹酚等成分协同可增强活性，如T. maroccanus精油中龙脑与百里酚（27.8%）共存时，念珠菌抑制活性显著提升[31]；迷迭香精油（龙脑23.7%）与ZnO纳米颗粒复合后，抑菌圈较单独使用时显著增大[121]。
在特定场景中，龙脑相关制剂表现出针对性效果：食品防腐领域，E. globulus、S. hortensis和M. communis精油对E. coli O157:H7和S. aureus的MIC为0.05–0.22%（v/v），其中S. hortensis精油对肉类中E. coli的抑制效果最佳，储存7天后可降低70.74%[122]；长效抗菌方面，IBOMA基聚合物涂层可水解释放龙脑，通过自更新及与樟脑的协同作用抑制细菌附着[111]；单独使用时，1.0–2.0%浓度的龙脑可抑制S. aureus等5种细菌，MFC为1.5–2.0%[123]。
除抗菌外，龙脑还具有显著抗尘螨活性：0.35 mg/mL龙脑精油（BEO）的尘螨驱避率达90.05±2.13%，0.70 mg/mL浓度处理48 h后死亡率>95%，机制可能为神经肌肉毒性导致尘螨脱水[124]。
综上，龙脑的多场景活性为天然抗菌剂开发提供了方向，尤其在食品防腐、化妆品及医药领域具有应用潜力[164, 195, 225]。
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