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| 0.0 | The research start at: 2026-09-21 09:57:24 (UTC+8) |
| 1.2 | The title is: 基于冰片结构类型的单萜类化合物研究 |
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Title: 基于冰片结构类型的单萜类化合物研究
冰片结构类型单萜在植物中的分布与含量特征
基于冰片结构的单萜类化合物在不同科属植物中的分布特征
基于冰片结构的单萜类化合物在不同科属植物中分布广泛，不同科属植物的精油、提取物或挥发性成分中均检测到冰片（或其衍生物l-乙酸冰片酯），其含量因物种、栽培品种、生态型、器官及生长阶段等因素存在差异。
不同科属植物中冰片（及l-乙酸冰片酯）的含量分布
| 科属 | 物种/样品 | 成分及含量 | 来源/备注 | 文献 |
|---|---|---|---|---|
| 柏科（Cupressaceae） | 台湾扁柏（C. obtusa）叶精油 | l-乙酸冰片酯（9.58–9.81%） | - | [1] |
| 唇形科（Lamiaceae） | Rosmarinus eriocalyx精油 | 冰片（12.19%） | - | [2] |
| 唇形科（Lamiaceae） | Thymus quinquecostatus和T. vulgaris不同栽培品种精油 | 冰片（0.41–5.91%） | - | [3] |
| 唇形科（Lamiaceae） | 百里香属植物精油 | 冰片 | 主要存在于开花期后样品中 | [4] |
| 唇形科（Lamiaceae） | Origanum tyttanthum Gontsch.精油 | 冰片（1.0–2.3%） | - | [5] |
| 唇形科（Lamiaceae） | 牛至精油（OEO） | 冰片（1.46±0.07%） | - | [6] |
| 唇形科（Lamiaceae） | 迷迭香（Rosmarinus officinalis）精油 | 冰片（11.07%） | - | [7] |
| 唇形科（Lamiaceae） | T. daenensis不同生态型精油 | 冰片（0.01–4.04%） | - | [8] |
| 唇形科（Lamiaceae） | 牛至属某植物精油 | 冰片（4.0%） | - | [9] |
| 唇形科（Lamiaceae） | 迷迭香精油 | 冰片（3.81%） | - | [10] |
| 唇形科（Lamiaceae） | 迷迭香（Rosmarinus）无性系（Esselte、Nonza、Pigette、Sudbery Blue、Voltz Splindler）VOC | 冰片（6% Nonza–14% Pigette） | 所有无性系均含冰片 | [11] |
| 唇形科（Lamiaceae） | T. macrophyllum精油 | 冰片（9.1%） | - | [12] |
| 唇形科（Lamiaceae） | T. satureioides和T. broussonetii精油 | 冰片（8.1–20.1%） | - | [13] |
| 唇形科（Lamiaceae） | 某百里香属植物精油 | 冰片（11.6%） | - | [14] |
| 唇形科（Lamiaceae） | 墨西哥牛至精油、百里香精油 | 冰片 | - | [15] |
| 唇形科（Lamiaceae） | Ac-AN精油、Lepechinia属植物精油 | 冰片 | - | [16]、[17] |
| 菊科（Asteraceae） | 艾属某植物精油 | 冰片（3.99%） | - | [18] |
| 菊科（Asteraceae） | 菊蒿属（Tanacetum）T. persicum花序精油 | 冰片、乙酸冰片酯（主要成分） | - | [19] |
| 菊科（Asteraceae） | Tanacetum polycephalum叶和花精油 | 冰片 | - | [19] |
| 菊科（Asteraceae） | 艾属某植物精油 | 冰片（13.20%） | - | [20] |
| 菊科（Asteraceae） | 蓍草属（Achillea）A. distans、A. lingulata、A. millefolium精油 | 冰片（最丰富成分） | - | [21] |
| 菊科（Asteraceae） | 蓍草（A. millefolium L.）花精油 | 冰片（12.4%） | 花部含量高于叶部 | [22] |
| 菊科（Asteraceae） | 蓍草（A. millefolium）精油 | 冰片（5.26%） | - | [23] |
| 菊科（Asteraceae） | 所有菊花（Chrysanthemum）精油、日本菊（Chrysanthemum japonense var. debile）精油 | 冰片（双环单萜成分） | 所有样品均检测到 | [24] |
| 松科（Pinaceae） | 冷杉属（Abies）木材、松柏类植物精油 | 冰片（含氧单萜成分） | - | [25]、[26] |
| 松科（Pinaceae） | 松属（Pinus）HH提取物及顶空成分 | 冰片（提取物：1.8–3.1%；顶空：8.3–11.9%） | - | [27] |
| 松科（Pinaceae） | 黑云杉水溶胶、balsam冷杉水溶胶 | 冰片（黑云杉：约14%；冷杉：6.4%） | - | [28] |
| 樟科（Lauraceae） | 某植物精油 | 冰片（2.09%） | - | [29] |
| 姜科（Zingiberaceae） | 某植物精油 | 冰片（4.78%） | 分离鉴定出冰片（2） | [30] |
| 姜科（Zingiberaceae） | 某植物精油 | 冰片（2.2%） | - | [31] |
| 姜科（Zingiberaceae） | 姜黄（C. longa）叶水蒸馏精油 | 冰片（0.3%） | - | [32] |
| 伞形科（Apiaceae） | 某植物精油 | 冰片（5.71%） | - | [33] |
| 其他科属 | 某植物精油 | 冰片（3.94%） | 气相色谱/质谱法鉴定 | [34] |
| 其他科属 | 缬草属（Valeriana）植物精油 | 冰片 | 所有样品均检测到，变异系数低（0.56–0.75） | [35] |
| 其他科属 | 鼠尾草（Salvia officinalis）精油 | 冰片（8.3%） | - | [36] |
| 其他科属 | 薰衣草（Lavandula angustifolia）精油 | 冰片（8.29%） | - | [37] |
| 其他科属 | 薰衣草精油（SL、CL） | 冰片（SL：6.3%；CL：4.0%） | - | [38] |
| 其他科属 | 混合精油（55% S. rosmarinus + 45% C. atlantica） | 冰片（3.01±1.21%） | - | [39] |
| 其他科属 | 某植物精油 | 冰片（3.56±1.41%） | - | [39] |
| 其他科属 | Lahaul-Spiti地区样品精油 | 冰片（10.94%） | 地理分布影响含量 | [40] |
| 其他科属 | 白 thyme 油 | 冰片（32%） | - | [41] |
| 其他科属 | 某植物样品 | 冰片（23.88–54.89%） | 部分样品为冰片型 | [42] |
| 其他科属 | 波兰柳树蜂蜜顶空成分 | 冰片（5.0–10.9%） | - | [43] |
| 其他科属 | 某植物叶片、花朵（B-5样品） | 冰片（叶片：0.20–8.50%；花朵：12.45%） | 花朵B-5样品含量最高 | [44] |
| 其他科属 | 某植物精油 | 冰片（21.8%） | - | [45] |
| 其他科属 | 某植物精油 | 冰片（14.99%） | - | [46] |
| 其他科属 | 某植物精油 | 冰片（主要含氧单萜成分） | - | [47]、[48] |
| 其他科属 | 某植物精油极性组分（LLD） | 冰片（8.5%） | - | [49] |
| 其他科属 | 某植物根茎提取物 | 冰片（3.9%） | - | [50] |
| 其他科属 | 某植物精油NO.1、NO.5样品、O2样品 | 冰片 | - | [24]、[51] |
| 其他科属 | 某植物精油、其浸提物挥发性成分 | 冰片 | - | [52] |
| 其他科属 | 西班牙集群2植物 | 冰片（与芳樟醇为主要化学特征） | - | [53] |
| 其他科属 | 某植物精油 | 冰片（5.58%、5.4%、1.9%、1.8%、1.3%、1.1%） | - | [54]、[55]、[56]、[57]、[58]、[59] |
| 其他科属 | 某植物精油 | 冰片（主要成分之一） | - | [60] |
| 其他科属 | 某植物精油 | 冰片（新增鉴定成分） | - | [61] |
此外，牛至属（Origanum）的Oregano species富含冰片等双环单萜[62]，部分植物精油中冰片含量存在地理差异[40]，且部分样品因冰片含量较高被划分为冰片型[42]。
冰片结构单萜在植物不同器官、物候期及地理环境中的含量变异规律
冰片结构类型单萜的含量受植物器官、物候期及地理环境的多重因素影响，具体差异如下：
不同因素对冰片结构类型单萜含量的影响
| 影响因素 | 植物种类/部位 | 具体表现 | 文献 |
|---|---|---|---|
| 植物器官 | Artemisia annua叶片 | 出芽期冰片含量最高 | [63] |
| 植物器官 | Thymus maroccanus叶片 | 花后期含较高冰片（16.3%） | [64] |
| 植物器官 | 1年生枝条针叶 vs 当年生枝条针叶 | 1年生枝条针叶冰片含量比当年生高48% | [65] |
| 植物器官 | Portuguese myrtle叶片 vs 未成熟浆果 | 叶片单萜含量花期（7月）达峰值，未成熟浆果酯类含量更高 | [66] |
| 植物器官 | Pittosporum maliformis花瓣和萼片 vs 生殖器官 | 花瓣和萼片中萜类最丰富，生殖器官中脂肪酸及其衍生物最丰富 | [67] |
| 植物器官 | 某植物叶、花、根、种子等所有器官 | 均含冰片结构类型单萜，其中冰片含量12.96%，乙酸龙脑酯含量26.18% | [68] |
| 物候期 | Cinnamomum haritha | 发芽/叶片发育期（2007年4-7月）冰片（内消旋体）和异冰片（外消旋体）含量最高，随休眠期下降，异冰片含量始终约为冰片的两倍 | [69] |
| 物候期 | Thymus armeniacus | 开花期100%阶段冰片含量显著高于50%阶段 | [70] |
| 物候期 | Thymus citriodorus | 冰片等成分在不同物候期存在变化 | [70] |
| 物候期 | Helleborus hircinum subsp. majus未成熟果实（8月）vs 成熟果实（10月） | 未成熟果实含氧单萜占54.46%，成熟果实烃类单萜占58.71% | [71] |
| 物候期 | Lavandula多数品种（除'Munstead'） | 芳樟醇含量从盛花期到花期末显著增加，芳樟酯含量显著下降 | [72] |
| 物候期 | 某些单萜醇（芳樟醇、冰片、萜品-4-醇） | 主要存在于开花后的精油中 | [4] |
| 物候期 | Portuguese myrtle叶片 | 单萜含量花期（7月）达峰值，5月最低 | [66] |
| 物候期/季节 | C. monspeliensis | 乙酸龙脑酯排放速率夏季显著高于其他季节 | [73] |
| 地理环境 | Achillea vulgaris不同国家来源 | 精油中单萜含量存在差异 | [74] |
| 地理环境 | Pinus属植物Quesnel位点（最北端） | 冰片等萜类含量显著高于其他位点 | [75] |
| 地理环境 | Satureja cuneifolia土耳其Sogut山（高海拔，8月花期）vs 意大利半岛东部（低海拔，12个野生位点） | 土耳其位点冰片含量2.5%；意大利位点冰片含量1.2-41.1%，为最主要化学型 | [76] |
| 地理环境 | Thymus vulgaris摩洛哥 vs 法国精油 | 摩洛哥精油冰片含量31.04%，法国精油未以冰片为主要成分 | [70] |
| 地理环境（温湿度） | Thymus transcaucasicus | 25℃时冰片和α-萜品醇含量增加，50%湿度时冰片含量达峰值 | [70] |
| 地理环境（基质） | C. monspeliensis硅质基质 vs 钙质基质 | 总萜烯排放速率硅质基质（5.28±1.96 μg g⁻¹ h⁻¹）显著高于钙质基质（0.78±0.16 μg g⁻¹ h⁻¹） | [73] |
上述结果表明，冰片结构类型单萜的分布与积累具有明显的时空特异性：器官层面，叶片、花瓣等营养/生殖器官的萜类组成存在分化；物候期层面，花期前后的含量变化与植物生长节律高度相关；地理环境层面，温度、湿度、海拔、基质类型及地域差异均会显著调控其含量或排放特征。这些因素的综合作用，共同决定了冰片结构单萜在植物体内的动态分布模式。
冰片结构单萜与相关单萜类化合物的共存模式及化学型关联
冰片结构类型单萜（如樟脑、冰片、异冰片、乙酸龙脑酯等）广泛分布于多种植物的挥发油或挥发性成分中，其含量特征及与其他单萜的共存模式因植物种类、生长阶段、产地及提取方法而异。不同植物及种群中冰片与樟脑的含量存在显著差异，具体数据如下：
不同植物及种群中冰片与樟脑的含量分布
| 植物种类/种群 | 冰片含量 | 樟脑含量 | 参考来源 |
|---|---|---|---|
| 松树Balgazyn种群针叶 | 仅2棵树检出（罕见） | - | [77] |
| 印度喜马拉雅地区迷迭香（水蒸气蒸馏法） | 3.35% | - | [78] |
| 阿尔及利亚迷迭香 | 5.11% | - | [78] |
| 西班牙迷迭香 | 4.8% | - | [20] |
| 波兰迷迭香（水蒸气蒸馏法） | 7.2% | - | [78] |
| 波兰迷迭香（超临界流体萃取法） | 9.2% | - | [78] |
| 西班牙迷迭香 | 3.81% | 20.91% | [10] |
| 百里香不同栽培品种 | 0.41%–5.91% | - | [3] |
| 摩洛哥百里香（花期后叶片） | 16.3% | - | [64] |
| 达能百里香不同生态型 | 0.01%–4.04% | - | [8] |
| 摩洛哥T. riatarum | 主要成分 | - | [70] |
| 摩洛哥Thymus vulgaris | 31.04% | - | [70] |
| 巴西某植物（A specimen） | 21.8% | - | [45] |
| 土耳其Sogut山Satureja cuneifolia | 2.5% | - | [76] |
| 意大利东部低海拔Satureja cuneifolia | 1.2%–41.1% | - | [76] |
| 艾蒿属Artemisia afra | 13.20% | 46.2% | [20]、[79] |
| 缬草属植物 | 所有样本均检出（变异系数0.56–0.75） | - | [35] |
| Cinnamomum haritha（内消旋冰片） | 异冰片含量约为其2倍 | 发芽/叶片发育阶段最高（35.3%），休眠期最低（15.3%） | [69] |
| 波兰柳树蜂蜜顶空成分 | 5.0%–10.9% | - | [43] |
| Cupressus septentrionale落叶 | - | 10.80% | [80] |
| 迷迭香 | - | 1.66%–24.82% | [78] |
| 百里香 | 检出 | 检出 | [81] |
| 菊花 | 检出（部分样本23.88%–54.89%） | 检出 | [24]、[42] |
冰片结构类型单萜常与其他单萜类化合物共存，形成特定化学型关联，反映植物体内单萜生物合成途径的联系及环境调控作用。在松树针叶中，冰片与β-侧柏烯、β-水芹烯、Δ3-蒈烯等同属罕见化合物组[77]，乙酸龙脑酯与柠檬烯、异松油烯等单萜及部分倍半萜存在中等程度关联（rβ=0.50–0.66）[77]。迷迭香中，冰片与樟脑、1,8-桉叶素、α-蒎烯等共同构成主要成分，不同产地和提取方法形成不同化学型[78]；西班牙迷迭香属α-蒎烯/1,8-桉叶素/樟脑化学型[81]，其挥发油中冰片与上述成分共存[10]。
百里香属植物中，摩洛哥百里香花期后叶片挥发油中冰片与百里酚、α-蒎烯、对伞花烃构成特征成分，形成独特化学型[64]；意大利东部Satureja cuneifolia中冰片为最主要化学型，芳樟醇和α-蒎烯仅部分样本高含量[76]；西班牙Thymus vulgaris存在樟脑骨架化学型及富含1,8-桉叶素、樟脑和冰片的化学型[70]；摩洛哥Thymus vulgaris中冰片与α-松油醇、香芹酚共存[70]。
Cinnamomum haritha中，冰片、异冰片与樟脑、1,8-桉叶素等含量变化趋势相似，且冰片是樟脑的生物合成前体[69]。缬草属植物中，乙酸龙脑酯为主要成分（2.9%–33.7%），与α-葑烯、缬草醇等共存[35]。艾蒿属Artemisia afra中，冰片与樟脑、1,8-桉叶素、青蒿酮等构成主要成分[20]。菊花中，冰片与α-蒎烯、β-蒎烯、樟脑、异冰片等共存[24]，且与α-蒎烯、β-蒎烯、樟脑、乙酸龙脑酯、柠檬烯呈正相关[42]，部分样本为冰片型化学型[42]。西班牙部分植物种群中，冰片与芳樟醇、顺式-水芹烯水合物共存形成特定化学型[53]。
提取方法与环境因子对植物中冰片结构单萜含量的影响
冰片结构类型单萜的分布、提取效率及含量受植物种类、提取方法、环境因子与处理措施的多重影响，其变化规律可通过系统性分析进一步明确。
不同植物中冰片结构单萜的分布特征
| 植物种类 | 分布情况 | 文献来源 |
|---|---|---|
| 迷迭香（Rosmarinus officinalis） | 精油中含冰片，含量因提取方法和环境因子而异 | [82][78] |
| 摩洛哥产Thymus riatarum | 精油以冰片为主要成分 | [70] |
| 法国产Thymus vulgaris | 精油中冰片含量为31.04% | [70] |
| Achillea thracica | 离体培养植株和迁地适应植株中检测到1,8-桉叶素等相关单萜 | [83] |
| Eucalyptus salubris | 精油经MAE、UAE等现代提取技术处理后含有冰片 | [84] |
提取方法对冰片结构单萜含量的影响
| 提取方法 | 研究对象 | 冰片含量/提取效果 | 文献来源 |
|---|---|---|---|
| 微波辅助提取（MW）2-4 | - | 可提取出冰片和γ-松油醇，其他方法无法提取 | [85] |
| 超临界流体微波萃取（SFME） | 迷迭香精油 | 冰片等含氧单萜含量为28.6%，高于水蒸馏法（HD）的26.98% | [82] |
| 水蒸馏法（HD） | 迷迭香精油 | 冰片含量为7.2% | [78] |
| 超临界流体萃取（SFE） | 迷迭香精油 | 冰片含量为9.2% | [78] |
| 分子蒸馏法 | 迷迭香精油 | 冰片含量为16%，高于水蒸气蒸馏法的4.5% | [78] |
| 超临界CO₂（SC-CO₂）萃取 | - | 压力与CO₂流速的交互作用对冰片含量有显著影响（p=0.0192）；最优条件（10 MPa、41℃、2.3 kg/h）下提取量为66.22 mg CE/100 g，30 MPa、50℃、3 kg/h条件下提升至92.82 mg CE/100 g | [86] |
环境因子与处理措施对冰片含量的影响
| 影响因素/处理措施 | 研究对象 | 冰片含量变化 | 文献来源 |
|---|---|---|---|
| γ辐照处理 | 迷迭香 | 含量随剂量增加而升高，1000 Gy时较对照（0 Gy）增加134% | [87] |
| s-UV-B处理90天 | 植物精油 | 含量显著增加342.9% | [88] |
| 锌（Zn）浓度升高 | - | 含氧单萜比例上升，冰片含量随Zn浓度增加而增加 | [89] |
| 氮（N）浓度 | 迷迭香精油 | 150 mg/L时含量达最大值11.55%，200 mg/L时降至9.10% | [90] |
| 生物刺激剂处理 | PR植株精油 | T2样品的冰片含量降低 | [91] |
| EMS诱变处理 | 普罗旺斯植株 | Provence EMS-B的冰片含量（21.01%）显著高于Provence EMS-A（3.55%） | [92] |
| 温度与湿度 | Thymus transcaucasicus | 25℃条件下含量增加，50%湿度时达到峰值 | [70] |
| 生物胁迫（真菌感染） | 植物 | 含量显著高于对照；非胁迫条件下施用5-氨基乙酰丙酸（ALA）可提升含量，真菌感染时较高剂量ALA能进一步增强含量 | [93] |
| 土壤类型 | C. monspeliensis | 硅质基质上的冰片释放量显著高于钙质基质 | [73] |
| 季节变化 | C. monspeliensis | 夏季冰片释放量显著高于其他季节 | [73] |
上述分析表明，冰片结构单萜的含量与分布是植物种类、提取技术及外部环境共同作用的结果。不同提取方法的效率差异为工业化生产提供了技术参考，而环境因子与处理措施的调控效应则为定向提高冰片含量的农业实践提供了理论依据。
冰片结构单萜的对映体组成及特定生态功能关联
在某些植物中，冰片对映体组成呈现显著的偏向性，这一特征表明(1S)-(−)-冰片可能作为姜科植物来源鉴定的重要标志物之一[94]。不同植物部位及姜科特定物种的冰片对映体分布模式如下表所示：
不同植物部位及姜科物种的冰片对映体组成
| 植物材料 | (1S)-(−)-冰片对映体过量值（ee） | 对映体分布特征 | 参考文献 |
|---|---|---|---|
| 根茎油 | 82.6% | (1S)-(−)-冰片含量显著高于(1R)-(+)-冰片 | [94] |
| 茎油 | >99% | (1S)-(−)-冰片含量显著高于(1R)-(+)-冰片 | [94] |
| 姜科植物Zingiber roseum的根茎油 | — | 与上述根茎油、茎油类似的对映体分布模式 | [94] |
冰片结构类型单萜的分析方法与结构表征
冰片结构型单萜在植物中的分布特征与含量分析
在植物中，冰片结构型单萜的分布具有物种和器官特异性，其含量与植物种类、器官、采收时期及处理方式密切相关，且鉴定方法以色谱技术为主。
不同植物中冰片结构型单萜的分布及含量
| 植物/样品 | 部位/处理 | 关键成分及含量 | 文献 |
|---|---|---|---|
| H. hircinum subsp. majus | 未成熟果实（8月采收） | 含氧单萜占54.46% | [71] |
| H. hircinum subsp. majus | 成熟果实（10月采收） | 单萜烃占58.71% | [71] |
| C. obtusa | 精油 | l-乙酸冰片酯含量为9.58–9.81% | [1] |
| Rosmarinus eriocalyx | 精油 | 樟脑（25.12%）、冰片（12.19%）、桉树脑（14.58%）、薄荷烯（9.31%） | [2] |
| 迷迭香 | 精油 | 冰片含量为11.07% | [7] |
| 迷迭香 | EVA膜洗脱精油 | 检测到冰片 | [95] |
| 迷迭香（α-蒎烯/桉树脑/樟脑化学型） | - | 气相色谱检测到冰片 | [81] |
| Mentha longifolia（L.）L.（HV1化学型） | 部分样品 | 冰片作为单萜醇类成分存在 | [96] |
| 百里香 | 精油 | 检测到冰片 | [81][97][15] |
| 百里香 | 提取物F2组分 | 冰片含量较其他组分增加约2倍 | [98] |
| A. calcarata | 根茎精油 | 检测到冰片 | [99] |
| 普罗旺斯植物 | EMS处理精油 | 冰片含量达21.01% | [92] |
| 松属植物 | 针叶 | 检测到冰片 | [77] |
| R. eriocalyx | 精油 | 检测到冰片 | [2] |
| 某些植物 | 开花期后精油 | 检测到冰片 | [4] |
| 特定植物 | 精油 | 冰片含量为2.09% | [29][34][55] |
| I. viscosa | 根排放谱 | 冰片含量达11.55% | [100] |
| K. galanga | 根茎油 | 冰片含量为1.0–2.7% | [101] |
| 未明确植物 | 新鲜样品 | 冰片含量为2.3% | [102] |
| 未明确植物 | 干燥样品 | 冰片含量为3.1% | [102] |
| 含1,8-桉叶素、樟脑等成分的植物 | 精油 | 检测到冰片 | [52] |
| 罗勒（O. basilicum） | - | 检测到冰片 | [103] |
分析方法方面，气相色谱-质谱联用（GC-MS）是鉴定冰片结构型单萜的主要手段[29][95][99][2][33][4][34][7][55][81][100][101][103]，部分研究结合气相色谱-火焰离子化检测器（GC-FID）进行定量分析[1][96]，另有研究采用顶空气相色谱（GC）结合外标法对冰片等单萜类化合物定量[104]；鉴定过程中常通过与商业标准品（如Fluka或Wako Pure Chemicals Industries, Ltd.提供的冰片标准品）的保留时间和质谱数据对比确认冰片存在[81][97]。
冰片结构型单萜的提取方法优化与分离技术
不同提取技术对冰片结构类型单萜的提取效率存在显著差异，各技术在提取效果、工艺参数及方法性能上呈现出不同特征。
不同提取技术对冰片及相关单萜的提取效果与性能参数
| 提取技术 | 关键发现 | 文献来源 |
|---|---|---|
| 微波辅助提取（MW） | 方法2–4可提取γ-萜品醇和冰片，方法1和3无法提取；方法2和4的氧合单萜提取量显著高于方法1和3 | [85] |
| 超快速微波辅助提取（SFME） | 氧合单萜（冰片、樟脑、萜品-4-醇等）含量为28.6%，高于传统水蒸馏（HD）的26.98% | [82] |
| 超临界CO₂萃取（SC-CO₂） | 压力与CO₂流速交互作用对冰片提取量有显著影响（p=0.0192）；优化条件下，10 MPa/41°C/2.3 kg/h时提取量为66.22 mg CE/100 g，30 MPa/50°C/3 kg/h时提升至92.82 mg CE/100 g | [86] |
| 固相微萃取（SPME） | 使用CAR/PDMS纤维可同时提取冰片等目标化合物；检测限5.3–48.2 ng/mL，定量限17.7–160.7 ng/mL，线性相关系数>0.9935，回收率93.03–100.5%，日内精密度RSD 1.1–15.3%，日间精密度RSD 7.2–15.5% | [105] |
此外，在提取后的分离过程中，通过特定分离方法可实现冰片的富集，例如在F2组分中，冰片的含量较原提取物增加约2倍[98]。
冰片及其衍生物的手性分离与构型表征
冰片及其衍生物的手性分离与构型表征方法多样，常用气相色谱-质谱联用（GC-MS）结合手性色谱柱实现对映体分离。不同来源的冰片对映体组成存在显著差异，构型表征可通过多种手段验证，环境因素对其对映体比例的影响规律仍需进一步研究。
不同来源冰片的对映体组成与相关分析方法
| 来源类型 | 具体来源/样品 | 对映体组成及特征 | 分析方法 | 文献引用 |
|---|---|---|---|---|
| 手性分离方法 | β-DEX 120手性色谱柱（30 m × 0.25 mm ID） | 可用于冰片的对映体分离 | GC-MS结合手性色谱柱 | [106] |
| 手性分离方法 | CPGC-MS技术 | 有效分离冰片及其杂质（如樟脑、异冰片）的对映体 | 手性气相色谱-质谱联用 | [107] |
| 天然产物分析 | 天然乙酸龙脑酯皂化所得冰片 | 仅检测到与(-)-冰片标准品保留时间一致的单一峰 | CPGC-MS | [107] |
| 天然产物分析 | Pinus属植物叶精油 | (-)-冰片为主要对映体 | 手性GC-MS | [108] |
| 药物制剂 | Rowachol | 对映体纯的(-)-冰片 | - | [106] |
| 药物制剂 | Terpinex、Terpichol、Uroterp | (+)-冰片显著过量 | - | [106] |
| 药物制剂 | Rowatinex | 冰片接近外消旋体 | - | [106] |
| 植物来源 | Baccharis tridentata（无论性别） | 专一合成(-)-冰片及(-)-乙酸龙脑酯 | - | [107] |
| 植物来源 | 日本鲜姜 | (1R,2S,4R)-(+)-冰片含量高于(1S,2R,4S)-(-)-冰片 | - | [109] |
| 植物来源 | Zingiber roseum根茎油 | (1S)-(-)-冰片过量，ee值为82.6% | - | [94] |
| 植物来源 | Zingiber roseum茎油 | (1S)-(-)-冰片过量，ee值>99% | - | [94] |
构型表征手段方面，CPGC-MS结合对映体标准品的保留时间对比是常用方法[107][108]；圆二色谱（CD）分析可进一步确认构型，例如天然乙酸龙脑酯的CD光谱在237 nm处出现最小值（-0.64），其皂化所得冰片的CD光谱在233 nm处出现最小值（-0.59），与文献报道一致，证实其为左旋对映体[107]；光学旋转测量也可辅助构型确定[107]。环境因素可能影响对映体比例，如高温和强降水条件下，某些单萜类化合物（如α-蒎烯）的对映体比例会发生变化[110]，但冰片对映体比例受环境影响的具体规律仍需进一步研究。
冰片结构型单萜的结构鉴定与分析方法应用
在冰片结构型单萜的结构鉴定与分析中，气相色谱（GC）及其联用技术是核心手段，辅以核磁共振（NMR）、傅里叶变换红外光谱（FTIR）及保留指数（LRI）等技术，共同支撑定性、定量与结构解析。不同分析方法在植物精油、实际样品中的应用及性能存在差异，具体数据如下：
不同分析方法在冰片检测中的应用及结果
| 分析方法 | 应用对象 | 关键结果 | 文献 |
|---|---|---|---|
| GC/MS | 迷迭香精油 | 冰片含量11.07% | [7] |
| GC-MS | 迷迭香精油 | 冰片含量3.81% | [10] |
| GC | 百里香精油 | 成功鉴定冰片 | [81] |
| 顶空气相色谱（GC）+外部标准品 | 单萜类化合物 | 通过保留时间比对和峰面积计算实现冰片的定性与定量 | [104] |
| GC/FID | 某精油 | 冰片含量达15.3 mg/mL | [111] |
| GC/MS | T. satureioides精油 | 冰片为主要成分之一，占比18.1% | [112] |
| GC/MS | C. longa叶精油 | 冰片含量为0.3% | [32] |
| DI-SPME结合GC-MS | herbal tea样品 | 线性相关系数>0.9935，回收率93.03%-100.5%，LOD 5.3-48.2 ng/mL，LOQ 17.7-160.7 ng/mL，日内精密度1.1%-15.3%，日间精密度7.2%-15.5% | [105] |
标准品制备与结构确证方面，可通过购买Sigma-Aldrich、Fluka等品牌的市售冰片（纯度≥90%或99%）[113][105][97]，或采用有机无溶剂法、柱色谱法分离制备单萜纯异构体（如α-和β-侧柏酮），并结合GC/MS、¹H NMR、¹³C NMR进行结构确证[114]。结构表征技术中，FTIR可用于定位分析，如缬草根切片中1737 cm⁻¹处吸收信号归属于乙酸冰片酯，FTIR成像可观察其在油体中的分布[115]；NMR技术可解析合成冰片衍生物的质子信号（如冰片基1-金刚烷基甲酸酯的甲基质子δ 0.80-0.97 ppm、酯基相连氢质子δ 4.55-4.93 ppm）[116]，含冰片的复合物分子则通过¹H NMR、¹³C NMR、红外光谱（IR）及元素分析验证结构与纯度[117]。此外，保留指数（LRI）与质谱数据比对可用于中性组分中冰片的鉴定[118]。上述技术的协同应用为冰片结构型单萜的研究提供了可靠支撑。
冰片结构类型单萜的生物合成与调控机制
冰片的生物合成涉及单萜环化、水解及脱氢等多步酶促反应，并受基因表达与环境因子的调控。单萜合成以香叶基二磷酸（GPP）为起始底物，经环化酶催化生成关键中间体；水解过程则通过两步酶促反应将中间体转化为冰片；脱氢酶的立体选择性催化进一步参与代谢调控。
不同物种中冰片生物合成关键酶的特征与功能
| 物种 | 酶名称 | 核心功能 | 关键特征/副产物 | 参考文献 |
|---|---|---|---|---|
| 鼠尾草（Salvia officinalis） | （+）-冰片基二磷酸合酶（SoBPPS） | 催化GPP环化生成（+）-冰片基二磷酸（BPP） | 二聚体形式，活性位点含I类环化酶特征序列DDXXD和（N,D）DXX(S,T)XXXE，需结合3个Mg²⁺和焦磷酸基团转变构象 | [119] |
| 薰衣草（Lavandula angustifolia） | LaBPPS | 催化GPP环化生成BPP | 与SoBPPS序列一致性50%，副产物包括α-蒎烯、β-蒎烯、莰烯和芳樟醇 | [119] |
| 华重楼（W. villosa） | Nudix水解酶WvNUDX24 | 特异性催化BPP水解生成冰片基磷酸（BP） | R84、S96、P98和G99为催化活性关键残基 | [120] |
| 鼠尾草（Salvia officinalis） | SoBDH1、SoBDH2 | 对（+）-冰片具有选择性催化活性 | SoBDH2：Kₘ=0.16±0.033 mM，kcat/Kₘ=1871.1 M⁻¹ min⁻¹，最适pH 9.5、温度60℃，偏好NAD⁺ | [121] |
| 酵母 | ADH2 | 对（+）-冰片和（-）-冰片均有脱氢酶活性 | 活性低于对（-）-顺式香芹醇和（-）-青蒿醇的催化活性 | [122] |
生物合成过程的调控机制可分为基因表达调控与环境因子调控两类。基因表达层面，赤霉素（GA）处理能显著提高鼠尾草幼叶中（+）-冰片基二磷酸合酶（BS）的转录本水平（为对照组的5倍），并促进冰片和樟脑积累（处理组含量达6.0-7.6 mg/g，对照组仅1.0 mg/g）；而赤霉素合成抑制剂（DAM）处理则产生相反效果[123]。此外，关键合成基因的表达具有组织和时间特异性，如冰片化学型植物中，（+）-新薄荷醇脱氢酶（E1.1.1.208）在7月表达量最高，对应冰片释放速率也达到峰值[124]。环境因子方面，氮素施加量增加会降低植物中冰片浓度[125]；s-UV-B处理90天后，冰片含量显著增加（达342.9%）[88]；细胞分裂素（如6-BA和KT）处理则可显著促进鱼腥草中冰片的积累[126]。
冰片结构类型单萜的生物活性与应用特性
冰片作为单萜类化合物，具有多种生物活性与应用特性，其相关研究覆盖毒理学、细胞毒性、抗菌活性、血脑屏障（BBB）通透性调节、抗惊厥活性、离子通道调节、抗炎与神经保护、酶抑制、药物渗透促进、抗寄生虫活性、昆虫活性、抗氧化、抗真菌生物膜、抗肿瘤及其他特性（如化感活性、蓝藻抑制、香气特性等）。以下为各领域关键研究结果的整合：
冰片在不同生物活性领域的关键研究结果
| 生物活性领域 | 具体研究结果 | 参考文献 |
|---|---|---|
| 毒理学 | Santolina油中冰片含量为8.37%，单一成分毒性低于精油及全混合物；去除冰片导致混合物毒性显著降低 | [127] |
| 细胞毒性 | 对HDF-Tert细胞系具有较低细胞毒性；与栀子苷联用（27.8、55.6、111.2 µg·mL−1）未显著降低HNECs活力 | [128]、[129] |
| 抗菌活性 | 与phellandrene、camphor、nerolidol抗菌效果相同；可能与Cupressus sempervirens精油对金黄色葡萄球菌和肠炎沙门氏菌的酶抑制作用相关；单独使用未表现明显抗菌活性；是迷迭香提取物潜在抗菌活性贡献成分之一 | [130]、[131]、[132]、[133] |
| 血脑屏障通透性调节 | 激活腺苷受体降低bEnd.3细胞ZO-1表达，上调A1AR和A2AAR；与PUE、TMP联用时分别提高其脑AUC0-12 1.34倍、1.30倍；修饰纳米粒（Lf-BNPs）促进16HBE细胞摄取，提高脑内递送效率；增加动物下丘脑5-HT含量提高BBB通透性；修饰银杏内酯脂质体提升其BBB通透性；调节氨基酸神经递质促进BBB开放；功能化纳米颗粒增强阿霉素等药物脑内递送 | [134]、[135]、[136]、[137]、[138] |
| 抗惊厥活性 | 含冰片核的萜类衍生物在PTZ诱导癫痫模型中3小时和24小时均有抗惊厥活性；(–)-冰片（50、100、200 mg/kg，ip）降低PTZ诱导小鼠阵挛性惊厥发生率、延长潜伏期，预防MES诱导的强直性惊厥 | [139]、[140] |
| 离子通道调节 | (+)-borneol对TRPV3的激活作用为樟脑的150%；(+)-和(–)-冰片在低浓度GABA条件下是a1b2g2L GABAA受体正调节剂，增强作用具有对映体差异；(+)-冰片在该受体上的GABA响应与戊巴比妥等相当或强于神经甾体5a-pregnan-3a-ol-20-one | [141]、[140] |
| 抗炎与神经保护 | ROS响应性冰片聚合物纳米粒抑制BV2小胶质细胞M1极化，降低脑梗死体积等；超临界鼠尾草提取物中的冰片降低THP-1/M细胞促炎因子分泌；通过调节分子机制协同或干扰抗炎通路改善病理状态；乳酸杆菌发酵大麻籽后冰片含量增加 | [142]、[143]、[144]、[145] |
| 酶抑制 | 对氨肽酶N（APN）具有浓度依赖性抑制作用，高浓度时可将其活性降低至原有活性的32–78% | [146] |
| 药物渗透促进 | 浓度依赖性增加栀子苷在MDCK和MDCK-MDR1细胞中的双向通量（机制与降低TJ蛋白、破坏肌动蛋白有关）；在HNECs模型中增加栀子苷Papp、降低TEER等；增强PPL·HCl皮肤渗透；与薄荷醇混合物增强氟康唑离体角膜通透性；BN-SBE-β-CD与MN、ITP联用增强大鼠皮肤渗透量 | [147]、[129]、[148]、[149]、[138] |
| 抗寄生虫活性 | 500 mg/L浓度下抑制南方根结线虫卵孵化和J2幼虫 mobility（抑制率均>90%）；某些含冰片的酯类化合物具有抗原生动物活性 | [150]、[118] |
| 昆虫活性 | 与麝香草酚二元组合对棉铃虫幼虫具有协同急性毒性；对某些昆虫为产卵引诱剂；对二斑叶螨具有显著驱避活性 | [151]、[152]、[153] |
| 抗氧化 | 降低Fos+38°C处理下BeL化学型植物中的O2–·和H2O2含量，缓解氧化应激 | [154] |
| 抗真菌生物膜 | 0.005%浓度下抑制白色念珠菌生物膜形成达80%以上 | [155] |
| 抗肿瘤 | 增强BDC对HepG2细胞的抗癌作用，机制包括增加细胞摄取、抑制ABCB1、诱导ROS介导的DNA损伤和G2/M期阻滞 | [156] |
| 其他特性 | 与1,8-桉叶素等共同为某些精油生物活性主要贡献成分；在两种植物品种中与α-蒎烯等为共有成分；100%抑制某些生物生长（蒸气压浓度<1 ppm时仍>50%抑制率）；1.2 mM浓度完全抑制铜绿微囊藻生长（机制涉及光合效率降低等）；具有草药/清凉香气特征 | [157]、[143]、[158]、[97]、[159]、[160] |
上述研究结果显示，冰片的生物活性具有多向性：在毒理学中表现出相对较低的单一成分毒性，却可能是混合物毒性的关键贡献者；在抗菌活性方面存在矛盾结论，提示其作用可能依赖于与其他成分的协同效应；在血脑屏障调节与药物递送领域，冰片通过直接作用于细胞通路或修饰纳米载体，显著提升药物脑内暴露量，展现出脑靶向应用潜力；抗惊厥、离子通道调节及抗炎神经保护等活性，则为其在神经系统疾病治疗中的应用提供了实验依据。此外，冰片在药物渗透促进、抗寄生虫、昆虫调控等领域的特性，也为其在医药、农业等多领域的开发提供了支撑。
冰片结构类型单萜的理化性质与转化规律
冰片作为双环单萜醇，具有辛辣的樟脑样气味和类似薄荷的灼烧味[161]，其在不同体系中的转化规律呈现多样化特征。此外，冰片与乙酸龙脑酯在竹姜油中共存，且单萜类的热稳定性弱于倍半萜，受热易发生骨架降解[162]。
不同体系中冰片的转化规律及特征
| 体系/反应类型 | 关键特征与结果 | 文献 |
|---|---|---|
| 松节油的SnCl₄·5H₂O催化反应 | 作为含杂原子的单体产物之一生成，且仅以双环化合物形式存在 | [163] |
| 蓝莓酒发酵过程 | 主要以糖苷结合态存在，游离态浓度增长远慢于总浓度，发酵结束时游离态占比低于10%，推测其糖苷更耐酸水解 | [161] |
| 钨交换羟基磷灰石（W/HAP）催化下的过氧化氢氧化反应 | 被高效氧化为樟脑，转化率近99%且选择性达100%，反应动力学符合一级反应，活化能为44.23 kJ mol⁻¹ | [164] |
| 大气OH氧化反应 | 生成二次有机气溶胶（SOA）的最大质量产率为0.33±0.06，平均氧碳比（O:C）为0.60±0.25，SOA产物分布与樟脑类似 | [165] |
| 体内代谢 | 樟脑可通过细胞色素P450（CYP450）羟基化转化为冰片 | [166] |
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