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:
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。
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。
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 |
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大果桉醛A | macrocarpal A | 132951-90-7 | C28H40O6 |
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圆叶肿柄菊素F | tagitinin F | 59979-57-6 | C19H24O6 |
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圆叶肿柄菊素A | [(1S,2S,4R,8S,9R,11R,12R)-1,12-dihydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradecan-9-yl] 2-methylpropanoate | 59979-61-2 | C19H28O7 |
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喘诺木烯内酯 | (+)-reynosin | 28254-53-7 | C15H20O3 |
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吐叶醇 | blumenol A | 23526-45-6 | C13H20O3 |
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可布酮 | kobusone | 24173-71-5 | C14H22O2 |
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去甲蕨素C | trans-Norpterosin C | 64890-70-6 | C13H16O3 |
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去乙酰锯齿泽兰内酯 | deacetyleupaserrin | 38456-39-2 | C20H26O6 |
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去乙酰氧母菊素 | leucodin | 17946-87-1 | C15H18O3 |
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千年健醇A | homalomenol A | 145400-03-9 | C15H26O2 |
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冬青醇 | 4α-hydroxy-4β-methyldihydrocostol | 72715-02-7 | C15H26O2 |
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冬青叶豚草酸 | ilicic acid | 4586-68-9 | C15H24O3 |
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二氢菜豆酸 | dihydrophaseic acid | 41756-77-8 | C15H22O5 |
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二乙酸丁香三环烷二醇酯 | Clovandioldiacetat | 2649-68-5 | C19H30O4 |
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丁香三环烷二醇 | clovanediol | 2649-64-1 | C15H26O2 |
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beta-莎草醇 | β-rotunol | 24405-57-0 | C15H22O2 |
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beta-木香酸 | β-costic acid | 3650-43-9 | C15H22O2 |
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[2R-[2ALPHA(S*),5ALPHA(R*)]]-2-(1,2-二羟基-1-甲基乙基)-6,10-二甲基螺[4.5]癸-6-烯-8-酮 | (1'S,2R,5S,10R)-2-(1′,2′-dihydroxy-1'-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one | 62623-86-3 | C15H24O3 |
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S-蜂斗菜螺内酯 | bakkenolide D | 18456-03-6 | C21H28O6S |
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Oplopanone; 10alpha-羟基日本刺参萜-4-酮 | oplopanone | 1911-78-0 | C15H26O2 |
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Oplodiol; (1S,4R,4aR,8aR)-1,2,3,4,4a,5,8,8a-八氢-1,4a-二甲基-7-(1-甲基乙基)-1,4-二羟基萘 | 1β,4β-dihydroxy-trans-eudesm-7-ene | 13902-62-0 | C15H26O2 |
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CorchoionosideC;(6S,9S)-长寿花糖甙 | corchoionoside C | 185414-25-9 | C19H30O8 |
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9-酮泽兰素 | 9-oxo-10,11-dehydroageraphorone | 79491-71-7 | C15H20O2 |
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9-表布卢姆醇 B | blumenol B | 22841-42-5 | C13H22O3 |
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9-氧代橙花叔醇 | 3S-(+)-9-oxonerolidol | 58865-88-6 | C15H24O2 |
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6,8-环-1,4-桉叶烷二醇 | 5α,7α(H)-6,8-cycloeudesma-1β,4β-diol | 213769-80-3 | C15H26O2 |
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5BETA-羟基木香酸 | 5β-hydroxycostic acid | 132185-84-3 | C15H22O3 |
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4,5-二氢布卢门醇A | 4,5-dihydroblumenol A | 155418-97-6 | C13H22O3 |
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4,10-香木兰烷二醇 | 4β,10α-aromadendranediol | 70051-38-6 | C15H26O2 |
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1BETA,6ALPHA-二羟基-4(14)-桉叶烯 | voleneol | 70389-88-7 | C15H26O2 |
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11(13)-去氢腋生依瓦菊素 | 11,13-Dehydroeriolin | 87441-73-4 | C15H20O4 |
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1,5,8-三甲基萘并[2,1-B]呋喃 | 1,5,8-Trimethylnaphtho<2,1-b>furan | 20013-76-7 | C15H14O |
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1,4,7-桉叶烷三醇 | (-)-1β,4β,7α-trihydroxyeudesmane | 145400-02-8 | C15H28O3 |
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(4S,5S)-(+)-吉马酮 4,5-环氧化物 | (4S,5S)-germacrone 4,5-epoxide | 92691-35-5 | C15H22O2 |
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(3R,3aR,7S,8aS)-3,3a,4,7,8,8a-六氢-6-(2-羟基乙基)-3,7-二甲基-2H-环庚烯并[b]呋喃-2-酮 | diversifolide | 1093207-99-8 | C13H20O3 |
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(3E)-4-[(3R,4S)-3,4-二羟基-2,6,6-三甲基-1-环己烯-1-基]-3-丁烯-2-酮 | cis-3,4-Dihydroxy-beta-ionone | 875666-39-0 | C13H20O3 |
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(2S,5E)-5-甲基-9-亚甲基-2-异丙基-5-环癸烯-1-酮 | Preisocalamendiol | 25645-19-6 | C15H24O |
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(2R,4aR,5R,8aS)-十氢-5-羟基-alpha,alpha,4a-三甲基-8-亚甲基-2-萘甲醇 | 4(15)-eudesmene-1β,11-diol | 83217-89-4 | C15H26O2 |
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(2R)-2-羟基-2-甲基-3-氧代丁酸(3AR,4R,6AR,8S,9AR,9BR)-8-(BETA-D-吡喃葡萄糖基氧基)十二氢-3,6,9-三(亚甲基)-2-氧代并[4,5-B]呋喃-4-基酯 | 8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C | 93395-31-4 | C26H34O12 |
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(2R)-2,3-二氢-6-(2-羟基乙基)-2,5,7-三甲基-1H-茚-1-酮 | 2(R)-pterosin B | 34175-96-7 | C14H18O2 |
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(1aR-(1aR*,3S*,4Z,5aR*,8aR*,9R*(Z),10aR*))-1a,2,3,5a,7,8,8a,9,10,10a-十氢-3-羟基-4,10a-二甲基-8-亚甲基-7-氧代环氧乙烷并(5,6)环癸(1,2-b)呋喃-9-基2-甲基-2-丁酸酯 | (1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate | 13323-48-3 | C20H26O6 |
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(1R-顺式)-5-甲基-ALPHA-亚甲基-4-(3-氧代丁基)-3-环庚烯-1-乙酸 | 4-oxo-bedfordia acid | 68799-38-2 | C15H22O3 |
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(-)-表蓝桉醇 | epiglobulol | 88728-58-9 | C15H26O |
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(-)-蓝桉醇 | globulol | 489-41-8 | C15H26O |
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(-)-地芰普内酯 | (+/-) loliolide | 5989-02-6 | C11H16O3 |
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—— | Germacra-3,9,11(13)-triene-12,15-dioic acid, 5,6,8-trihydroxy-, 12,8-lactone, methyl ester, 5-acetate 2-chloro-3-hydroxy-2-methylbutyrate | 24694-80-2 | C23H29ClO9 |
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—— | arteanniun L | 207446-89-7 | C15H22O3 |
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—— | (2S)-4-[(1R)-2,6,6-Trimethyl-4-oxo-2-cyclohexen-1-yl]-2-butanyl β -D-glucopyranoside | 62512-23-6 | C19H32O7 |
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—— | (5a<i>R</i>,6<i>R</i>)-5<i>t</i>-acetoxy-7<i>c</i>,8<i>c</i>-epoxy-8a-hydroxy-9<i>anti</i>-isopropenyl-5a-methyl-(5a<i>r</i>,8a<i>c</i>)-hexahydro-spiro[1<i>c</i>,4<i>c</i>-methano-cyclopent[<i>d</i>]oxepin-6,2'-oxiran]-2-one | 2749-28-2 | C17H20O7 |
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—— | Torilolonacetat | 20482-21-7 | C17H26O4 |
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