倍半萜
倍半萜是含三个异戊二烯单位的萜类化合物，一般通式为CH，大多遵循异戊二烯规则。这类化合物在自然界中分布广泛，在木兰目、芸香目、山茱萸目及菊目植物中最丰富。倍半萜多以含有氧原子的衍生物形式存在于挥发油中，如醇、酮和内酯等，是高沸点部分的主要组成部分，并具有较强的香气和生物活性，广泛应用于医药、食品和化妆品工业。
从数量和结构骨架类型来看，倍半萜类化合物是萜类化合物中最丰富的。它们通常根据碳环数进行分类，包括无环、单环、双环、三环及四环等多种类型；此外也可按环的大小分类，如五元环、六元环、七元环乃至十一元大环。按倍半萜结构中的含氧基团进行分类，则有助于理解其理化性质和生理活性，例如倍半萜醇、醛、内酯等。
以下是一些常见的倍半萜类化合物：
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金合欢醇（farnesol）是一种开链型倍半萜，广泛存在于香茅草、橙花及玫瑰的挥发油中。它为无色油状液体，具有独特的香气和保幼激素活性，可抑制昆虫变态和成熟。
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杜鹃酮（germacrone），又称大牻牛儿酮，存在于兴安杜鹃叶的挥发油中，是一种十元环单环倍半萜。其熔点为56～57℃，兴安杜鹃挥发油具有止咳、祛痰和平喘作用，可用于治疗慢性支气管炎，而杜鹃酮是其中的重要成分。
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愈创木奥（guaiazulene）是一种存在于蒺藜科植物愈创木和老鹳草挥发油中的倍半萜。它为蓝色针状结晶，熔点为31℃，具有抗炎作用，并能促进烫伤或灼伤创面的愈合，是国产烫伤膏的主要成分之一。
图1所示为愈创木奥的结构式。
| 中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
|---|---|---|---|---|
| —— | [(2Z)-6-(acetyloxymethyl)-10,11-dihydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl] 2-methylprop-2-enoate | 76248-63-0 | C21H26O9 |
|
| —— | Leptocarpin | 13323-48-3 | C20H26O6 |
|
| —— | ilicic acid | 4586-68-9 | C15H24O3 |
|
| —— | palustrol | 5986-49-2 | C15H26O |
|
| —— | Annuionone C | 155418-97-6 | C13H20O3 |
|
| —— | humulene-1,2-monoepoxide | 19888-34-7 | C15H24O |
|
| —— | (1S,2S,5S,8R,9R)-2,9-diacetoxyclovane | 2649-68-5 | C19H30O4 |
|
| —— | Clovandiol | 2649-64-1 | C15H26O2 |
|
| —— | 2β,9β-dihydroxymethoxyclovane | 2649-64-1 | C15H26O2 |
|
| —— | Ilic-saeure | 4586-68-9 | C15H24O3 |
|
| —— | 11,13-dihydrodehydroleucodin | 17946-87-1 | C16H22O3 |
|
| —— | achillin | 5181-80-6 | C15H18O3 |
|
| —— | Eupatoriopicrine | 6856-01-5 | C20H26O6 |
|
| —— | [(3aR,4R,6Z,8S,10Z,11aR)-8-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-2-(hydroxymethyl)but-2-enoate | 38456-39-2 | C20H26O6 |
|
| —— | [(1S,2E,8R,10R,11R)-6-(acetyloxymethyl)-10,11-dihydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl] 2-methylprop-2-enoate | 76248-63-0 | C21H26O9 |
|
| —— | Chlorantholide C | 1372558-35-4 | C15H18O3 |
|
| —— | tagitinin F | 59979-57-6 | C19H24O6 |
|
| —— | Petasilide | 18455-98-6 | C22H30O6 |
|
| —— | Acetoxyparthenolide | 41059-80-7 | C17H22O5 |
|
| —— | (3aR,4R,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one | 6750-25-0 | C15H20O3 |
|
| —— | (3aR,4S,6Z,10Z,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one | 6750-25-0 | C15H20O3 |
|
| —— | 10Hβ-9-oxoageraphorone | 105181-06-4 | C15H22O2 |
|
| —— | Uvedalin | 24694-79-9 | C23H28O9 |
|
| —— | Zederone | 7727-79-9 | C15H18O3 |
|
| —— | (3-acetyloxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl) (E)-3-methylsulfanylprop-2-enoate | 18456-03-6 | C21H28O6S |
|
| —— | (5Z)-5-Methyl-9-methylidene-2-propan-2-ylcyclodec-5-en-1-one | 25645-19-6 | C15H24O |
|
| —— | vomifoliol | 23526-45-6 | C13H20O3 |
|
| —— | humulene epoxide II | 19888-34-7 | C15H24O |
|
| —— | (6Z)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one | 92691-35-5 | C15H22O2 |
|
| —— | [1-(1-acetyloxyethyl)-4-methylidene-2-oxo-7-propan-2-yl-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate | 104012-37-5 | C23H34O5 |
|
| —— | Roseosid | 54835-70-0 | C19H30O8 |
|
| —— | (6S,9S)-vomifoliol | 189351-15-3 | C13H20O3 |
|
| —— | (E)-6,9-dihydroxymegastigma-4,7-dien-3-one 9-O-β-D-glucopyranoside | 54835-70-0 | C19H30O8 |
|
| —— | megastigmane | 276870-26-9 | C13H24O4 |
|
| —— | dihydrovomifoliol | 22841-42-5 | C13H22O3 |
|
| —— | 8β-hydroxyparthenolide acetate | 41059-80-7 | C17H22O5 |
|
| —— | (1R,3aR,4R,7aS)-3a-methyl-1-(2-methylallyl)-7-methyleneoctahydro-1H-inden-4-ol | 70389-96-7 | C15H24O |
|
| —— | 4-hydroxy-11(13)-eudesmen-12-oic acid | 4586-68-9 | C15H24O3 |
|
| —— | blumenol B | 36151-01-6 | C13H22O3 |
|
| —— | Macrocarpal E | 142628-54-4 | C28H40O6 |
|
| —— | Titrotundine | 56377-67-4 | C19H28O6 |
|
| —— | 2-(4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid | 3650-43-9 | C15H22O2 |
|
| —— | 2,4,6-Trihydroxy-5-[1-[4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]-3-methylbutyl]benzene-1,3-dicarbaldehyde | 179388-54-6 | C28H42O7 |
|
| —— | 2,4,6-Trihydroxy-5-[1-[6-(2-hydroxypropan-2-yl)-8a-methyl-4-methylidene-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]-3-methylbutyl]benzene-1,3-dicarbaldehyde | 179388-53-5 | C28H40O6 |
|
| —— | Macrocarpal N | 172617-99-1 | C28H38O7 |
|
| —— | Corianin | 35481-77-7 | C15H18O6 |
|
| —— | 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde | 142628-53-3 | C28H38O5 |
|
| —— | 2-[2-(8-Hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)propan-2-yloxy]-6-methyloxane-3,4,5-triol | 349112-30-7 | C21H38O6 |
|
| —— | 6-Hydroxy-5a-methyl-3,9-dimethylidenedecahydronaphtho[1,2-b]furan-2(3h)-one | 28254-53-7 | C15H20O3 |
|
| —— | 4,4,8-trimethyltricyclo[6.3.1.0(1,5)]dodecane-2,9-diol | 2649-64-1 | C15H26O2 |
|
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