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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
—— 1-(4-fluorophenyl)-3-[(Z)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]thiourea —— C22H18FN3OS
1-(4-fluorophenyl)-3-[(Z)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]thiourea
—— Hydroxy-[[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]methyl]-oxophosphanium —— C16H12O9P+
Hydroxy-[[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]methyl]-oxophosphanium
—— 6-[1-(5,7-Dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydrochromen-8-yl)-3-methylbutyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione —— C31H36O7
6-[1-(5,7-Dihydroxy-6-methyl-4-oxo-2-phenyl-2,3-dihydrochromen-8-yl)-3-methylbutyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione
—— 5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R,2S,3R,4R)-1,2,3,4-tetrahydroxypentyl]oxan-2-yl]oxychromen-4-one —— C26H30O14
5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R,2S,3R,4R)-1,2,3,4-tetrahydroxypentyl]oxan-2-yl]oxychromen-4-one
—— 3-[(2'R)-2-amino-2'-(2,3-difluorophenyl)-3'-methyl-5-oxospiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile —— C25H18F2N4O2
3-[(2'R)-2-amino-2'-(2,3-difluorophenyl)-3'-methyl-5-oxospiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile
—— 3,6-Diamino-2-(3-methoxyphenyl)chromen-4-one —— C16H14N2O3
3,6-Diamino-2-(3-methoxyphenyl)chromen-4-one
—— N-[6-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]pyridin-2-yl]methanesulfonamide —— C21H20N2O4S
N-[6-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]pyridin-2-yl]methanesulfonamide
—— (2s)-5,2'-Dihydroxy-7,5'-dimethoxyflavanone —— C17H16O6
(2s)-5,2'-Dihydroxy-7,5'-dimethoxyflavanone
—— 3-Ethoxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-5,7-diol —— C19H19O7+
3-Ethoxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-5,7-diol
—— 5-[(2S,4S)-3,4-dihydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,2,3-triol —— C17H18O8
5-[(2S,4S)-3,4-dihydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-2-yl]benzene-1,2,3-triol
—— methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-3,4-dihydro-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-methyl-2H-chromene-3-carboxylate —— C69H58O17
methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-3,4-dihydro-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-methyl-2H-chromene-3-carboxylate
—— (E)-1-[4-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one —— C28H34O15
(E)-1-[4-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
—— Flavan-3,3,4-triol —— C15H14O4
Flavan-3,3,4-triol
—— N-(6-bromo-2-phenyl-2H-chromen-4-yl)-2-methylpropane-2-sulfinamide —— C19H20BrNO2S
N-(6-bromo-2-phenyl-2H-chromen-4-yl)-2-methylpropane-2-sulfinamide
—— [5-(3,7-Dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-methylphosphinic acid —— C16H13O8P
[5-(3,7-Dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-methylphosphinic acid
—— 3',4',5'-trimethoxyflav-2-ene —— C18H18O4
3',4',5'-trimethoxyflav-2-ene
—— 2-(4-ethoxy-3-hydroxy-5-methylphenyl)-8-[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol —— C33H32O11
2-(4-ethoxy-3-hydroxy-5-methylphenyl)-8-[3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
—— (5R,7S,8R)-8-[[4-(3,4-dihydro-2H-chromen-2-yl)benzoyl]amino]-N-hydroxy-1-oxaspiro[4.4]nonane-7-carboxamide —— C25H28N2O5
(5R,7S,8R)-8-[[4-(3,4-dihydro-2H-chromen-2-yl)benzoyl]amino]-N-hydroxy-1-oxaspiro[4.4]nonane-7-carboxamide
—— 5-[1-[3-bromo-4-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]ethenyl]-4-hydroxy-3H-1,3-thiazol-2-one —— C32H28BrNO10S
5-[1-[3-bromo-4-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]ethenyl]-4-hydroxy-3H-1,3-thiazol-2-one
—— 2-(2,3-Dihydroxy-4-methylphenyl)-3-hydroxychromen-4-one;ethane —— C20H24O5
2-(2,3-Dihydroxy-4-methylphenyl)-3-hydroxychromen-4-one;ethane
—— 8-Amino-2-(3-chloro-4-fluorophenyl)-3-methoxy-6-methylchromen-4-one —— C17H13ClFNO3
8-Amino-2-(3-chloro-4-fluorophenyl)-3-methoxy-6-methylchromen-4-one
—— [(1S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-[(2R)-7-hydroxy-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]chromen-2-yl]methanesulfonic acid —— C39H45NO8S
[(1S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]-[(2R)-7-hydroxy-3-(4-hydroxyphenyl)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]chromen-2-yl]methanesulfonic acid
—— (4Z)-4-[2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-2-phenyl-1,3-oxazol-5(4H)-one —— C25H17NO4
(4Z)-4-[2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-2-phenyl-1,3-oxazol-5(4H)-one
—— (2R)-8-(3,7-dimethylocta-2,6-dienyl)-5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one —— C26H30O4
(2R)-8-(3,7-dimethylocta-2,6-dienyl)-5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
—— 6-Bromo-3,3-diphenylbenzo[f]chromene;ethane —— C29H29BrO
6-Bromo-3,3-diphenylbenzo[f]chromene;ethane
—— Ethane;3-methoxy-2-phenylchromen-4-one —— C24H36O3
Ethane;3-methoxy-2-phenylchromen-4-one
—— 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-6-methyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C24H26O11
5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-6-methyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 5-Hydroxy-3-(13-hydroxytridecyl)-7-methoxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one —— C29H38O8
5-Hydroxy-3-(13-hydroxytridecyl)-7-methoxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one
—— (3aS,4R,9bR)-8-[tert-butyl(dimethyl)silyl]oxy-4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-2-one;(3aS,4R,9bR)-8-methyl-2-methylidene-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromene —— C81H110O9Si4
(3aS,4R,9bR)-8-[tert-butyl(dimethyl)silyl]oxy-4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-2-one;(3aS,4R,9bR)-8-methyl-2-methylidene-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromene
—— (E)-2-(3-methoxy-4-phenylmethoxyphenyl)-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)chromen-4-imine —— C33H26N2O3S
(E)-2-(3-methoxy-4-phenylmethoxyphenyl)-N-(5-methyl-4-phenyl-1,3-thiazol-2-yl)chromen-4-imine
—— 1-[2,6-dihydroxy-4-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one —— C28H34O15
1-[2,6-dihydroxy-4-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
—— 3-Bromo-10,11-dimethoxy-5,5-bis(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene —— C38H33BrO5
3-Bromo-10,11-dimethoxy-5,5-bis(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene
—— (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]oxane-3,4,5-triol —— C21H24O8
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]oxane-3,4,5-triol
—— [(3S,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-[4-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate —— C36H36O18
[(3S,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-[4-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
—— 3-Methyl-7-(2-methylprop-2-enoxy)-2-phenyl-8-[3-(3,4,5-trimethoxyphenyl)prop-1-enyl]chromen-4-one —— C32H32O6
3-Methyl-7-(2-methylprop-2-enoxy)-2-phenyl-8-[3-(3,4,5-trimethoxyphenyl)prop-1-enyl]chromen-4-one
—— 3-Ethenyl-2-phenyl-3,4-dihydrochromen-2-ol —— C17H16O2
3-Ethenyl-2-phenyl-3,4-dihydrochromen-2-ol
—— (5-Hydroxy-4-oxo-2-phenylchromen-7-yl) 4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoate —— C28H25NO7S
(5-Hydroxy-4-oxo-2-phenylchromen-7-yl) 4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoate
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one —— C21H20O13
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one
—— 4-(4-methoxyphenyl)-N-[(4E)-2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-5-methyl-1,3-thiazol-2-amine —— C27H22N2O3S
4-(4-methoxyphenyl)-N-[(4E)-2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-5-methyl-1,3-thiazol-2-amine
—— [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-6-[3-(3,4-dihydroxyphenyl)prop-2-enoxymethyl]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate —— C49H53O25+
[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-6-[3-(3,4-dihydroxyphenyl)prop-2-enoxymethyl]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate
—— methyl 2-(1,3-benzodioxol-5-yl)-4-chloro-6-methyl-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylate —— C45H37ClO11
methyl 2-(1,3-benzodioxol-5-yl)-4-chloro-6-methyl-2H-chromene-3-carboxylate;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylate
—— 2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-oxo-4H-chromen-4-yl]-5,7-dihydroxy-4H-chromen-3-one —— C30H22O12
2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-oxo-4H-chromen-4-yl]-5,7-dihydroxy-4H-chromen-3-one
—— 8-(4-Butylphenyl)-9-hydroxy-2-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-2-phenylbenzo[h]chromene-4-carboxamide —— C47H45N3O4
8-(4-Butylphenyl)-9-hydroxy-2-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-2-phenylbenzo[h]chromene-4-carboxamide
—— 3-[6-[(3,4-Dihydroxy-6-methyloxan-2-yl)oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one —— C27H30O15
3-[6-[(3,4-Dihydroxy-6-methyloxan-2-yl)oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-(3-hydroxy-3-methylbutyl)chromen-4-one —— C20H20O8
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-(3-hydroxy-3-methylbutyl)chromen-4-one
—— (3Z)-3-(1H-indol-3-ylmethylidene)-2-phenylchromen-4-one —— C24H17NO2
(3Z)-3-(1H-indol-3-ylmethylidene)-2-phenylchromen-4-one
—— 3,5-Dimethoxy-2-(3-nitrophenyl)chromen-4-one —— C17H13NO6
3,5-Dimethoxy-2-(3-nitrophenyl)chromen-4-one
—— 2'-(cyclohexylmethyl)-2'-phenylspiro[1H-imidazole-4,4'-3H-chromene]-5-one —— C24H26N2O2
2'-(cyclohexylmethyl)-2'-phenylspiro[1H-imidazole-4,4'-3H-chromene]-5-one
—— 6-(4-Acetyl-phenoxy)-5,7,4'-trihydroxy-flavon —— C23H16O7
6-(4-Acetyl-phenoxy)-5,7,4'-trihydroxy-flavon
—— N-[(4E)-2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-5-methyl-4-(thiophen-2-yl)-1,3-thiazol-2-amine —— C24H18N2O2S2
N-[(4E)-2-(4-methoxyphenyl)-4H-chromen-4-ylidene]-5-methyl-4-(thiophen-2-yl)-1,3-thiazol-2-amine