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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
—— (2R)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O11
(2R)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C23H24O13
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C21H20O13
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— (2R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O11
(2R)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 2-phenyl-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C21H20O8
2-phenyl-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O10
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— (2S)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O11
(2S)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— (2S,3R,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C21H21O11+
(2S,3R,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C23H24O13
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— Cyanidin 3-O-alpha-L-galactoside —— C21H21O11+
Cyanidin 3-O-alpha-L-galactoside
—— (2R,3S,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C21H21O11+
(2R,3S,4R,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— (11R)-7,15-dihydroxy-19,19-dimethyl-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,14,16(21),17-octaen-13-one —— C25H22O6
(11R)-7,15-dihydroxy-19,19-dimethyl-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,14,16(21),17-octaen-13-one
—— (11S)-7,15-dihydroxy-19,19-dimethyl-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,14,16(21),17-octaen-13-one —— C25H22O6
(11S)-7,15-dihydroxy-19,19-dimethyl-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),5,7,14,16(21),17-octaen-13-one
—— 5-[2-(4-Methoxyphenyl)chromen-4-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H13NO3S2
5-[2-(4-Methoxyphenyl)chromen-4-ylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (2S,3R)-3-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one —— C16H14O4
(2S,3R)-3-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
—— (2S)-7,8-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one —— C17H16O4
(2S)-7,8-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
—— (11S)-6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-enyl)-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,15,17,21-octaen-13-one —— C30H30O7
(11S)-6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-enyl)-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,15,17,21-octaen-13-one
—— (11R)-6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-enyl)-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,15,17,21-octaen-13-one —— C30H30O7
(11R)-6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-enyl)-11-(2-methylprop-1-enyl)-2,10,20-trioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4,6,8,15,17,21-octaen-13-one
—— 2-(3-bromophenoxy)-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]acetamide —— C23H19BrN2O3
2-(3-bromophenoxy)-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]acetamide
—— 4-[2-(4-Methoxyphenyl)chromen-4-ylidene]-2-phenyl-1,3-oxazol-5-one —— C25H17NO4
4-[2-(4-Methoxyphenyl)chromen-4-ylidene]-2-phenyl-1,3-oxazol-5-one
—— 2-[3-[3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C27H31O17+
2-[3-[3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— N,N-diethyl-5-nitro-2-[(2E)-2-[(2R)-2-phenyl-2,3-dihydrochromen-4-ylidene]hydrazinyl]benzenesulfonamide —— C25H26N4O5S
N,N-diethyl-5-nitro-2-[(2E)-2-[(2R)-2-phenyl-2,3-dihydrochromen-4-ylidene]hydrazinyl]benzenesulfonamide
—— 2-[3,4-dihydroxy-5-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one —— C21H20O12
2-[3,4-dihydroxy-5-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one
—— 2-[3,4-dihydroxy-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one —— C21H20O12
2-[3,4-dihydroxy-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one
—— 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-7-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C23H24O12
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-7-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 2-[3,4-dihydroxy-5-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one —— C21H20O12
2-[3,4-dihydroxy-5-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one
—— 2-[3,4-dihydroxy-5-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one —— C21H20O12
2-[3,4-dihydroxy-5-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-5,7-dihydroxychromen-4-one
—— 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-7-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C23H24O12
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-7-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— ethyl (2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylate —— C23H24O11
ethyl (2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylate
—— ethyl (2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylate —— C23H24O11
ethyl (2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2S)-5-hydroxy-2-(2-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylate
—— 2-nitro-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-4-(trifluoromethyl)aniline —— C22H16F3N3O3
2-nitro-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-4-(trifluoromethyl)aniline
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one —— C22H22O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one —— C22H22O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one
—— (2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid —— C21H18O10
(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one —— C22H22O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one
—— (2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid —— C21H18O10
(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one —— C22H22O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]chromen-4-one
—— (2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid —— C21H18O10
(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
—— 8-(6-Fluoro-4-oxo-chroman-2-yl)-4H-benzo[1,3]dioxine-6-carboxylic acid —— C18H13FO6
8-(6-Fluoro-4-oxo-chroman-2-yl)-4H-benzo[1,3]dioxine-6-carboxylic acid
—— N-(4-chlorophenyl)-3-nitro-4-[2-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydrazinyl]benzenesulfonamide —— C27H21ClN4O5S
N-(4-chlorophenyl)-3-nitro-4-[2-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydrazinyl]benzenesulfonamide
—— 4-[2-(3-Iodo-4,5-dimethoxyphenyl)chromen-4-ylidene]-2-methyl-1,3-oxazol-5-one —— C21H16INO5
4-[2-(3-Iodo-4,5-dimethoxyphenyl)chromen-4-ylidene]-2-methyl-1,3-oxazol-5-one
—— 6-bromo-2-(3,4-dimethoxyphenyl)-8-methoxy-3-nitro-2H-chromene —— C18H16BrNO6
6-bromo-2-(3,4-dimethoxyphenyl)-8-methoxy-3-nitro-2H-chromene
—— 2-(3,4-dihydroxyphenyl)-3,4,5-trihydroxy-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-7-one —— C21H20O13
2-(3,4-dihydroxyphenyl)-3,4,5-trihydroxy-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-7-one
—— N-[4-(3,4-dimethoxyphenyl)-5-methyl-1,3-thiazol-2-yl]-2-(4-methoxyphenyl)-6-propoxychromen-4-imine —— C31H30N2O5S
N-[4-(3,4-dimethoxyphenyl)-5-methyl-1,3-thiazol-2-yl]-2-(4-methoxyphenyl)-6-propoxychromen-4-imine
—— 2-(3-methoxy-4-phenylmethoxyphenyl)-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)chromen-4-imine —— C33H26N2O3S
2-(3-methoxy-4-phenylmethoxyphenyl)-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)chromen-4-imine
—— 11-(4-fluorophenyl)-9-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C25H19FN4O
11-(4-fluorophenyl)-9-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C21H20O10
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C21H20O10
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 4-nitro-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzamide —— C22H17N3O4
4-nitro-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzamide
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C27H30O16
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one