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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
—— (5Z)-3-[(4-chlorophenyl)methyl]-5-[[4-(4-oxochromen-2-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione —— C26H16ClNO4S
(5Z)-3-[(4-chlorophenyl)methyl]-5-[[4-(4-oxochromen-2-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
—— N-[(Z)-(2-phenylchroman-4-ylidene)amino]aniline —— C21H18N2O
N-[(Z)-(2-phenylchroman-4-ylidene)amino]aniline
—— 5-Hydroxy-2-[2-hydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one —— C31H34O11
5-Hydroxy-2-[2-hydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
—— 5,7-Dihydroxy-2-(2,3,4-trimethoxyphenyl)chromen-4-one —— C18H16O7
5,7-Dihydroxy-2-(2,3,4-trimethoxyphenyl)chromen-4-one
—— 5-Hydroxy-2-[4-hydroxy-2-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one —— C31H34O11
5-Hydroxy-2-[4-hydroxy-2-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
—— N'-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-N-(1-phenylethyl)oxamide —— C25H23N3O3
N'-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-N-(1-phenylethyl)oxamide
—— [3,4,5-triacetyloxy-6-[[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]carbamothioylamino]oxan-2-yl]methyl acetate —— C30H33N3O10S
[3,4,5-triacetyloxy-6-[[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]carbamothioylamino]oxan-2-yl]methyl acetate
—— 1-methyl-3-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]thiourea —— C17H17N3OS
1-methyl-3-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]thiourea
—— 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(2-hydroxyethoxy)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C29H34O17
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(2-hydroxyethoxy)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— 2,3-Dihydrogossypetin 40525-53-9 C15H12O8
2,3-Dihydrogossypetin
—— 6-[7-Hydroxy-2-(4-hydroxyphenyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-5-(hydroxymethyl)oxane-2,3,4-triol;chloride —— C27H31ClO15
6-[7-Hydroxy-2-(4-hydroxyphenyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-5-(hydroxymethyl)oxane-2,3,4-triol;chloride
—— 2-(4-Hydroxy-3-methoxyphenyl)-8-methoxy-2,3-dihydrochromen-4-one —— C17H16O5
2-(4-Hydroxy-3-methoxyphenyl)-8-methoxy-2,3-dihydrochromen-4-one
—— Prunus inhibitor A —— C30H24O10
Prunus inhibitor A
—— 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-5-one —— C15H10O6
2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-5-one
—— [3,4,5-trihydroxy-6-[[2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate —— C30H28O11
[3,4,5-trihydroxy-6-[[2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
—— Eupalin 29617-75-2 C23H24O11
Eupalin
—— [(Z)-[(2S)-2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea —— C18H15ClFN3O3S
[(Z)-[(2S)-2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea
—— 7-[(2-Chlorophenyl)methoxy]-5-hydroxy-2-phenylchromen-4-one —— C22H15ClO4
7-[(2-Chlorophenyl)methoxy]-5-hydroxy-2-phenylchromen-4-one
—— (5-hydroxy-4-oxo-2-phenylchromen-7-yl) (2R)-2-(phenylmethoxycarbonylamino)propanoate —— C26H21NO7
(5-hydroxy-4-oxo-2-phenylchromen-7-yl) (2R)-2-(phenylmethoxycarbonylamino)propanoate
—— [(Z)-[(2R)-2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea —— C18H15ClFN3O3S
[(Z)-[(2R)-2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea
—— [(Z)-[(2S)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea —— C18H16FN3O3S
[(Z)-[(2S)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea
—— 1-tert-butyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl) (2S)-pyrrolidine-1,2-dicarboxylate —— C25H25NO7
1-tert-butyl 2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl) (2S)-pyrrolidine-1,2-dicarboxylate
—— 1-O-tert-butyl 2-O-(5-hydroxy-4-oxo-2-phenylchromen-7-yl) (2R)-pyrrolidine-1,2-dicarboxylate —— C25H25NO7
1-O-tert-butyl 2-O-(5-hydroxy-4-oxo-2-phenylchromen-7-yl) (2R)-pyrrolidine-1,2-dicarboxylate
—— (E)-[2-(4-methoxyphenyl)-6-methylchromen-4-ylidene]-(2-phenylethyl)azanium —— C25H24NO2+
(E)-[2-(4-methoxyphenyl)-6-methylchromen-4-ylidene]-(2-phenylethyl)azanium
—— (E)-(4-hydroxyphenyl)-[2-(4-methoxyphenyl)-6-methylchromen-4-ylidene]azanium —— C23H20NO3+
(E)-(4-hydroxyphenyl)-[2-(4-methoxyphenyl)-6-methylchromen-4-ylidene]azanium
—— 2-methoxy-4-[(4E)-4-[[(2R)-oxolan-2-yl]methylimino]chromen-2-yl]phenol —— C21H21NO4
2-methoxy-4-[(4E)-4-[[(2R)-oxolan-2-yl]methylimino]chromen-2-yl]phenol
—— (E)-[6-chloro-2-(3,4-dimethoxyphenyl)chromen-4-ylidene]-[2-(diethylamino)ethyl]azanium —— C23H28ClN2O3+
(E)-[6-chloro-2-(3,4-dimethoxyphenyl)chromen-4-ylidene]-[2-(diethylamino)ethyl]azanium
—— 2-methoxy-4-[(4E)-4-[[(2S)-oxolan-2-yl]methylimino]chromen-2-yl]phenol —— C21H21NO4
2-methoxy-4-[(4E)-4-[[(2S)-oxolan-2-yl]methylimino]chromen-2-yl]phenol
—— 7-[(4-Chlorophenyl)methoxy]-5-hydroxy-2-phenylchromen-4-one —— C22H15ClO4
7-[(4-Chlorophenyl)methoxy]-5-hydroxy-2-phenylchromen-4-one
—— 5-hydroxy-7-[(4-nitrobenzyl)oxy]-2-phenyl-4H-chromen-4-one —— C22H15NO6
5-hydroxy-7-[(4-nitrobenzyl)oxy]-2-phenyl-4H-chromen-4-one
—— benzyl 2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetate —— C24H18O6
benzyl 2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetate
—— Tert-butyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate —— C21H20O6
Tert-butyl 2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyacetate
—— 7-[2-[(4S)-2,2-dimethyloxan-4-yl]-2-oxoethoxy]-5-hydroxy-2-phenylchromen-4-one —— C24H24O6
7-[2-[(4S)-2,2-dimethyloxan-4-yl]-2-oxoethoxy]-5-hydroxy-2-phenylchromen-4-one
—— 7-[2-[(4R)-2,2-dimethyloxan-4-yl]-2-oxoethoxy]-5-hydroxy-2-phenylchromen-4-one —— C24H24O6
7-[2-[(4R)-2,2-dimethyloxan-4-yl]-2-oxoethoxy]-5-hydroxy-2-phenylchromen-4-one
—— ethyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutanoate —— C21H20O6
ethyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutanoate
—— ethyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate —— C20H18O6
ethyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate
—— ethyl (2R)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate —— C20H18O6
ethyl (2R)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate
—— (NZ)-N-[6-fluoro-2-(4-methoxyphenyl)chromen-4-ylidene]hydroxylamine —— C16H12FNO3
(NZ)-N-[6-fluoro-2-(4-methoxyphenyl)chromen-4-ylidene]hydroxylamine
—— (NZ)-N-[2-(4-methoxyphenyl)-6-nitrochromen-4-ylidene]hydroxylamine —— C16H12N2O5
(NZ)-N-[2-(4-methoxyphenyl)-6-nitrochromen-4-ylidene]hydroxylamine
—— 1-methyl-N-[(Z)-[(2S)-2-phenyl-2,3-dihydrochromen-4-ylidene]amino]pyrrole-2-carboxamide —— C21H19N3O2
1-methyl-N-[(Z)-[(2S)-2-phenyl-2,3-dihydrochromen-4-ylidene]amino]pyrrole-2-carboxamide
—— 5-hydroxy-7-[(2R)-3-oxobutan-2-yl]oxy-2-phenylchromen-4-one —— C19H16O5
5-hydroxy-7-[(2R)-3-oxobutan-2-yl]oxy-2-phenylchromen-4-one
—— 5-hydroxy-7-[(2S)-3-oxobutan-2-yl]oxy-2-phenylchromen-4-one —— C19H16O5
5-hydroxy-7-[(2S)-3-oxobutan-2-yl]oxy-2-phenylchromen-4-one
—— (NZ)-N-[(2S)-2-(4-chlorophenyl)-2,3-dihydrochromen-4-ylidene]hydroxylamine —— C15H12ClNO2
(NZ)-N-[(2S)-2-(4-chlorophenyl)-2,3-dihydrochromen-4-ylidene]hydroxylamine
—— (NZ)-N-[6-ethyl-2-(4-methoxyphenyl)chromen-4-ylidene]hydroxylamine —— C18H17NO3
(NZ)-N-[6-ethyl-2-(4-methoxyphenyl)chromen-4-ylidene]hydroxylamine
—— (E)-2-(4-methoxyphenyl)-6-methyl-N-(2-methylpropyl)chromen-4-imine —— C21H23NO2
(E)-2-(4-methoxyphenyl)-6-methyl-N-(2-methylpropyl)chromen-4-imine
—— (NZ)-N-[(2R)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-methoxy-2,3-dihydrochromen-4-ylidene]hydroxylamine —— C18H17NO5
(NZ)-N-[(2R)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-methoxy-2,3-dihydrochromen-4-ylidene]hydroxylamine
—— (NZ)-N-[(2S)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-methoxy-2,3-dihydrochromen-4-ylidene]hydroxylamine —— C18H17NO5
(NZ)-N-[(2S)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-methoxy-2,3-dihydrochromen-4-ylidene]hydroxylamine
—— methyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate —— C19H16O6
methyl (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate
—— methyl (2R)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate —— C19H16O6
methyl (2R)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoate
—— (2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoic acid —— C18H14O6
(2S)-2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxypropanoic acid