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黄酮类化合物

黄酮类化合物 定义与结构特征

黄酮类化合物是一大类天然存在的有机化合物,属于酚类衍生物。它们的分子结构通常包含两个苯环(A和B环)和一个三碳环(C环),形成一个基本骨架。该骨架由多个亚结构组成,包括黄烷醇、黄酮、黄酮醇等。

生物来源

黄酮类化合物广泛存在于植物界中,常见于许多蔬菜、水果及中药中。例如,在大豆、柑橘、茶叶和甘草中都可以找到它们的身影。

化学性质 亲水性与溶解度

由于其分子结构中含有多个酚羟基,因此具有一定的亲水性和良好的溶解性,这使得黄酮类化合物在药物设计中扮演重要角色。

稳定性与光敏性

大多数黄酮类化合物相对稳定,在适宜条件下不易发生降解。但某些类型的黄酮对光照比较敏感,容易被氧化,导致颜色变化。

生理活性与药用价值

黄酮类化合物因其丰富的生理活性而备受关注,主要包括:

  • 抗氧化作用:可有效清除体内自由基,保护细胞免受损伤。
  • 抗炎效应:有助于减轻炎症反应,缓解症状。
  • 心血管保护:可能通过多种机制改善心脑血管健康。
  • 抗癌潜力:研究表明某些黄酮类物质具有抑制肿瘤生长的能力。
应用领域 食品工业

作为一种天然色素和抗氧化剂,被广泛应用于食品加工中以提高其保质期及营养价值。

化妆品行业

利用其良好的生物相容性和抗衰老特性,在化妆品配方中应用广泛。

药物开发

由于黄酮类化合物展现出广泛的药理活性,已成为新药研发的重要候选目标之一。

中文名称 英文名称 CAS号 化学式 结构式图片
—— tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 25711-50-6 C63H68O21
tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
—— (2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-formyl-6-hydroxyflavan 848047-64-3 C51H44O8
(2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-formyl-6-hydroxyflavan
—— ent-catechin 3',4',5,7-tetra-O-methyl ether 104263-86-7 C19H22O6
ent-catechin 3',4',5,7-tetra-O-methyl ether
—— [4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin 12798-58-2 C30H26O12
[4,6]-2,3-trans-3,4-trans-(+)-catechin-(+)-catechin
—— (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',5',7-pentahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-6-yl>flavan 10572-94-8 C30H26O12
(2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',5',7-pentahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-6-yl>flavan
—— tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 3888-39-9 C42H46O14
tetra-O-methyl-3-O-acetyl-(-)-epicatechin-(4β,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin
—— <4,6:4,8>-2,3-trans-3,4-trans:2'',3''-trans-3'',4''-cis-bi-<(-)-robinetinidol>-(+)-catechin dodecamethyl ether triacetate 85820-28-6 C63H68O21
<4,6:4,8>-2,3-trans-3,4-trans:2'',3''-trans-3'',4''-cis-bi-<(-)-robinetinidol>-(+)-catechin dodecamethyl ether triacetate
—— octa-O-methyl-di-O-acetyl-bis-(+)-catechin 3888-39-9 C42H46O14
octa-O-methyl-di-O-acetyl-bis-(+)-catechin
—— (2R,3S)-4-(3-hydroxy-5,7-dimethoxychroman-2-yl)benzene-1,2-diol 94102-41-7 C17H18O6
(2R,3S)-4-(3-hydroxy-5,7-dimethoxychroman-2-yl)benzene-1,2-diol
—— catechin-7-O-sulfate 1123761-39-6 C15H14O9S
catechin-7-O-sulfate
—— 8-bromo-3,5,7,3',4'-penta-O-benzyl-(+)-catechin 89385-19-3 C50H43BrO6
8-bromo-3,5,7,3',4'-penta-O-benzyl-(+)-catechin
—— (+)-catechin 4',5-disulfate 141180-79-2 C15H14O12S2
(+)-catechin 4',5-disulfate
—— (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5,7-dimethoxychroman-3-ol 300346-49-0 C30H26O6
(2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5,7-dimethoxychroman-3-ol
—— acetic acid 3,5-diacetoxy-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)chroman-7-yl ester 89329-08-8 C34H28O9
acetic acid 3,5-diacetoxy-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)chroman-7-yl ester
—— 3-O-(4-hydroxy-3,5-dimethoxybenzoyl)catechin 1166820-78-5 C24H22O10
3-O-(4-hydroxy-3,5-dimethoxybenzoyl)catechin
—— <4,8:4,6>-all-trans-tri-<(+)-catechin> 88244-65-9 C45H38O18
<4,8:4,6>-all-trans-tri-<(+)-catechin>
—— catechin-(4α->8)-ent-epicatechin 88314-66-3 C30H26O12
catechin-(4α->8)-ent-epicatechin
—— (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5-methoxychroman-3,7-diol 300346-47-8 C29H24O6
(2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-5-methoxychroman-3,7-diol
—— <4,6:4,8>-all-trans-bi-<(-)-robinetinidol>-(+)-catechin dodecamethyl ether triacetate —— C63H68O21
<4,6:4,8>-all-trans-bi-<(-)-robinetinidol>-(+)-catechin dodecamethyl ether triacetate
—— Trifluoro-acetic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yl ester 882867-41-6 C45H37F3O7
Trifluoro-acetic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yl ester
—— (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-4-(2-hydroxyethoxy)-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol 679797-90-1 C45H42O8
(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-4-(2-hydroxyethoxy)-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
—— (-)-robinetinidol-(4β,8)-(+)-catechin 78185-18-9 C30H26O12
(-)-robinetinidol-(4β,8)-(+)-catechin
—— <4,8:4,8:4,8>-all-trans-tetra-<(+)-catechin> 88244-66-0 C60H50O24
<4,8:4,8:4,8>-all-trans-tetra-<(+)-catechin>
—— (2R,3S)-2,3-trans-6-<(2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxyflavan-4-yl>-8-<(2R,3S,4R)-2,3-trans-3,4-cis-3,3',-4',7-tetrahydroxyflavan-4-yl>-3,3',4',5,7-pentahydroxyflavan 81600-44-4 C45H38O16
(2R,3S)-2,3-trans-6-<(2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxyflavan-4-yl>-8-<(2R,3S,4R)-2,3-trans-3,4-cis-3,3',-4',7-tetrahydroxyflavan-4-yl>-3,3',4',5,7-pentahydroxyflavan
—— (2R,3S)-3,3',4',5,7-pentamethoxyflavan 51154-08-6 C20H24O6
(2R,3S)-3,3',4',5,7-pentamethoxyflavan
—— (+)-catechine 7-O-β-D-xylopyranoside 42830-48-8 C20H22O10
(+)-catechine 7-O-β-D-xylopyranoside
—— 5,7-dihydroxy-3,4'-dimethoxyflavylium chloride 13544-51-9 C17H15O5*Cl
5,7-dihydroxy-3,4'-dimethoxyflavylium chloride
—— 3',4'-Dimethoxyflavylium 60264-81-5 C17H15O3
3',4'-Dimethoxyflavylium
—— 1608504-19-3 C22H23FO7
—— (2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan 1352123-18-2 C59H53BrO9
(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan
—— <4,8>-3,4-trans-(+)-fisetinidol-(+)-catechin 78306-05-5 C30H26O11
<4,8>-3,4-trans-(+)-fisetinidol-(+)-catechin
—— gambirflavan D4 1107651-50-2 C30H28O12
gambirflavan D4
—— 3',4',5,7-tetramethyldihydroquercetin —— C19H20O7
3',4',5,7-tetramethyldihydroquercetin
—— (2S,3R,4S,2'R,3'S)-2,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,7,3',5',7'-pentaol 88269-46-9 C30H26O11
(2S,3R,4S,2'R,3'S)-2,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,7,3',5',7'-pentaol
—— (2<i>R</i>)-2<i>r</i>-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3<i>t</i>-(toluene-4-sulfonyloxy)-chroman 120640-46-2 C26H28O8S
(2<i>R</i>)-2<i>r</i>-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3<i>t</i>-(toluene-4-sulfonyloxy)-chroman
—— (2R,3S,8R,9S,10S)-10-(2,4-Dihydroxy-phenyl)-8-(3,4-dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol —— C31H28O11
(2R,3S,8R,9S,10S)-10-(2,4-Dihydroxy-phenyl)-8-(3,4-dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol
—— (+)-leucorobinetinidin 4382-45-0 C15H14O7
(+)-leucorobinetinidin
—— 3,3',4',5,6,7-hexa-O-benzyl-elephantorrhizol 848047-73-4 C57H50O8
3,3',4',5,6,7-hexa-O-benzyl-elephantorrhizol
—— 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin 51196-37-3 C30H26O12
3,4-cis-(+)-catechin-(4β->8)-(+)-catechin
—— [3-(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl)propan-2-ol-1α->6-(+)catechin] 76236-92-5 C30H28O12
[3-(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl)propan-2-ol-1α->6-(+)catechin]
—— 3’,4’,5,7-tetra-O-benzyl-8-bromoepicatechin-(4β8)-3’,4’,5,7-tetra-O-benzylepicatechin 923565-06-4 C86H73BrO12
3’,4’,5,7-tetra-O-benzyl-8-bromoepicatechin-(4β8)-3’,4’,5,7-tetra-O-benzylepicatechin
—— epioritin-4α-ol 577-30-0 C15H14O6
epioritin-4α-ol
—— (+)-catechin 8-C-β-D-glucopyranoside 103215-50-5 C25H32O11
(+)-catechin 8-C-β-D-glucopyranoside
—— (+)-epicatechin-<4α->8>-(+)-epicatechin 82262-98-4 C30H26O12
(+)-epicatechin-<4α->8>-(+)-epicatechin
—— 6,8-di-C-benzyl-5,7,3',4'-tetra-O-benzyl-(+)-catechin 1007091-02-2 C57H50O6
6,8-di-C-benzyl-5,7,3',4'-tetra-O-benzyl-(+)-catechin
—— 3',4',5,7-tetra-O-benzyl-8-bromocatechin-4α,8-(3',4',5,7-tetra-O-benzylepicatechin) 923565-05-3 C86H73BrO12
3',4',5,7-tetra-O-benzyl-8-bromocatechin-4α,8-(3',4',5,7-tetra-O-benzylepicatechin)
—— ent-epifisetinidol-4β-ol 2958-11-4 C15H14O6
ent-epifisetinidol-4β-ol
—— (2R,3S,4S)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2''-ethoxy-ethoxy)-flavan 1352123-17-1 C54H51BrO8
(2R,3S,4S)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2''-ethoxy-ethoxy)-flavan
—— 1608504-20-6 C22H24O8
—— (+)-(2R,3S,4S)-3,4-dihydroxy-5,7,3',4'-tetramethoxyflavan 35499-74-2 C19H22O7
(+)-(2R,3S,4S)-3,4-dihydroxy-5,7,3',4'-tetramethoxyflavan