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甾体化合物

甾体化合物是一类重要的生物活性分子,具有独特的碳环结构和立体异构特征。它们广泛存在于自然界中,尤其是在植物、动物以及微生物体内,是医药化学领域的一个重要研究对象。

结构特点

甾体的基本结构包括一个由17个碳原子组成的环状骨架(C-17),通常含有四个共轭的六元环系统:A环、B环、C环和D环。这一结构通过不同的侧链修饰形成了多种化学性质各异的甾体化合物,例如胆固醇、孕甾酮等。

分类

根据其分子中碳原子数量的不同,甾体可以进一步分为不同的类别:

  • 固醇(Sterols):包括胆固醇、羊毛脂甾醇等。
  • 甾烷(Steranes):具有与固醇相似结构的化合物,在古代生物遗迹中广泛存在。
  • 皂苷(Saponins):含有甾体母核和糖基,能够形成泡沫,是许多植物次生代谢产物的重要成分。
生物功能

甾体化合物在生物体内扮演着多种角色:

  1. 激素:如性激素(雌激素、孕激素)、皮质醇等。
  2. 细胞信号传导:通过与受体结合调节细胞内信号通路,影响基因表达及细胞行为。
  3. 膜结构成分:胆固醇是动物细胞膜脂质双层的重要组成之一。
医药应用

由于甾体化合物独特的生物活性,在医药化工领域得到了广泛应用:

  • 合成药物:包括激素类药物、抗炎药等。
  • 抗癌药物研发:部分甾体衍生物被发现具有抑制癌细胞生长的作用,成为新药研究的重要方向之一。
研究方法

对甾体化合物的研究通常涉及多种分析技术和化学反应:

  • 光谱学技术(如NMR、UV)用于结构鉴定。
  • 色谱法(HPLC、GC)进行分离纯化。
  • 合成方法:通过有机合成途径制备不同类型的甾体衍生物。

总的来说,甾体化合物因其广泛的生理活性和潜在的医疗价值,在化学化工及生物医药领域占据重要地位。

中文名称 英文名称 CAS号 化学式 结构式图片
—— Androst-7-ene-6,17-dione, 2,3,14-trihydroxy-, (2beta,3beta,5beta)- 19466-41-2 C19H26O5
Androst-7-ene-6,17-dione, 2,3,14-trihydroxy-, (2beta,3beta,5beta)-
—— 5b-Cholest-7-en-6-one, 2beta,3beta,11alpha,14,20,22-hexahydroxy-, (22R)- 23044-80-6 C27H44O7
5b-Cholest-7-en-6-one, 2beta,3beta,11alpha,14,20,22-hexahydroxy-, (22R)-
—— Estra-4.9.11-trien-3.17-dion 4642-95-9 C18H20O2
Estra-4.9.11-trien-3.17-dion
—— 3,17-Dioxo-oestra-4,9,11-trien 4642-95-9 C18H20O2
3,17-Dioxo-oestra-4,9,11-trien
—— 4-Stigmasten-3-one 1058-61-3 C29H48O
4-Stigmasten-3-one
—— (1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione 95975-55-6 C22H30O3
(1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione
—— 7-Oxositosterol 145163-97-9 C29H48O2
7-Oxositosterol
—— Androst-5-ene-3,17-diol, 3-acetate 17-benzoate, (3beta,17beta)- 5953-63-9 C28H36O4
Androst-5-ene-3,17-diol, 3-acetate 17-benzoate, (3beta,17beta)-
—— 7β,17α-Dimethyl-17-hydroxyandrost-4-en-3-on 1605-89-6 C21H32O2
7β,17α-Dimethyl-17-hydroxyandrost-4-en-3-on
—— 7α,17α-Dimethyltestosteron 1605-89-6 C21H32O2
7α,17α-Dimethyltestosteron
—— Calusterone 1605-89-6 C21H32O2
Calusterone
—— (1S,2S,4S,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol 126-17-0 C27H43NO2
(1S,2S,4S,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol
—— Stigmastan-3-ol, (3a,5b,24S)- 83-45-4 C29H52O
Stigmastan-3-ol, (3a,5b,24S)-
—— 4-Androsten-3-on-17β-carbonsaeure-methylester 2681-55-2 C21H30O3
4-Androsten-3-on-17β-carbonsaeure-methylester
—— Cholesteryl-cinnamat 1990-11-0 C36H52O2
Cholesteryl-cinnamat
—— 3-Oxo-bis-nor-4-cholen-22-al 903-30-0 C22H32O2
3-Oxo-bis-nor-4-cholen-22-al
—— 24-methylcholesta-7,22E-diene-3β,5α,6β-triol 516-37-0 C28H46O3
24-methylcholesta-7,22E-diene-3β,5α,6β-triol
—— Poriferasterol monoglucoside 19716-26-8 C35H58O6
Poriferasterol monoglucoside
—— (2S,4S,5'R,6R,7S,9S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol 126-17-0 C27H43NO2
(2S,4S,5'R,6R,7S,9S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol
—— 3-Desoxydehydroepiandrosteron 25824-80-0 C19H28O
3-Desoxydehydroepiandrosteron
—— Ergosta-7,22-dien-3-one 32507-77-0 C28H44O
Ergosta-7,22-dien-3-one
—— Glycodeoxycholsaeure 360-65-6 C26H43NO5
Glycodeoxycholsaeure
—— deoxycholylglycine 360-65-6 C26H43NO5
deoxycholylglycine
—— Glykodeoxycholsaeure 360-65-6 C26H43NO5
Glykodeoxycholsaeure
—— 17α-Methyl-5β-androstan-3β,17β-diol 641-82-7 C20H34O2
17α-Methyl-5β-androstan-3β,17β-diol
—— 18-Methyl-11-methylen-Δ<sup>4</sup>-estren-3,17-dion 54024-17-8 C20H26O2
18-Methyl-11-methylen-Δ<sup>4</sup>-estren-3,17-dion
—— Chondrillasterolacetat 4651-46-1 C31H50O2
Chondrillasterolacetat
—— β-anhydroepidigitoxigenin 1901-24-2 C23H32O3
β-anhydroepidigitoxigenin
—— β-Anhydro-digitoxigenin 1901-24-2 C23H32O3
β-Anhydro-digitoxigenin
—— (2β,3β,5β,17β)-2,3,14-Trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methy lbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]androst-7-en-6-one 22798-96-5 C30H48O7
(2β,3β,5β,17β)-2,3,14-Trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methy lbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]androst-7-en-6-one
—— 3α,5-cyclo-5α-ergosta-6,8(14),22-triene 24352-51-0 C28H42
3α,5-cyclo-5α-ergosta-6,8(14),22-triene
—— Ergosterol-peroxid 2061-64-5 C28H44O3
Ergosterol-peroxid
—— 25-Hydroxytachysterol 3 39932-44-0 C27H44O2
25-Hydroxytachysterol 3
—— (6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one 36450-01-8 C29H46O2
(6beta,22E)-6-Hydroxystigmasta-4,22-dien-3-one
—— Purapuridine;Solancarpidine;Solasodin 126-17-0 C27H43NO2
Purapuridine;Solancarpidine;Solasodin
—— (1S,2S,4S,6R,7S,8R,9S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol 126-17-0 C27H43NO2
(1S,2S,4S,6R,7S,8R,9S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol
—— (2S,7S,8R,9S,12S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol 126-17-0 C27H43NO2
(2S,7S,8R,9S,12S,13R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-ol
—— 25-Hydroxycholest-5-en-3-ol 2140-46-7 C27H46O2
25-Hydroxycholest-5-en-3-ol
—— 2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol 39932-44-0 C27H44O2
2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol
—— beta-Sitostenone 1058-61-3 C29H48O
beta-Sitostenone
—— (3beta)-9,19-Cyclolanost-24-en-3-yl 4-hydroxy-3-methoxycinnamate 21238-33-5 C40H58O4
(3beta)-9,19-Cyclolanost-24-en-3-yl 4-hydroxy-3-methoxycinnamate
—— Solasod-5-en-3 beta-ol 126-17-0 C27H43NO2
Solasod-5-en-3 beta-ol
—— 24α<sub>F</sub><i>H</i>-stigmastene-(4)-diol-(3β.6β) 75500-83-3 C29H50O2
24α<sub>F</sub><i>H</i>-stigmastene-(4)-diol-(3β.6β)
—— Δ<sup>4</sup>-Stigmastenon-(3) 1058-61-3 C29H48O
Δ<sup>4</sup>-Stigmastenon-(3)
—— (8S,9S,10R,13R,14S,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one 1058-61-3 C29H48O
(8S,9S,10R,13R,14S,17R)-17-[(2R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
—— alpha-Spinasterol 3-glucoside 1745-36-4 C35H58O6
alpha-Spinasterol 3-glucoside
—— rubrosterone 19466-41-2 C19H26O5
rubrosterone
—— 3β-acetoxy-(8α)-pregna-5,16-dien-20-one 979-02-2 C23H32O3
3β-acetoxy-(8α)-pregna-5,16-dien-20-one
—— β-stigmasterol 3β-glucoside 19716-26-8 C35H58O6
β-stigmasterol 3β-glucoside
—— (22E,24S)-stigmasta-5,22-dien-3β,7α-diol 64998-19-2 C29H48O2
(22E,24S)-stigmasta-5,22-dien-3β,7α-diol