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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
—— [7-Hydroxy-2-(4-hydroxyphenyl)-6-octadec-9-enoyl-3-octadec-9-enoyloxy-4-oxochromen-5-yl] octadec-9-enoate —— C69H106O9
[7-Hydroxy-2-(4-hydroxyphenyl)-6-octadec-9-enoyl-3-octadec-9-enoyloxy-4-oxochromen-5-yl] octadec-9-enoate
—— 9-(3-chlorophenyl)-11-(4-chlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C24H16Cl2N4O
9-(3-chlorophenyl)-11-(4-chlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— (6R)-2-cyclopropyl-3-methyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-6,7-diol —— C20H20N2O3
(6R)-2-cyclopropyl-3-methyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-6,7-diol
—— (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-4-oxo-5-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carbonyl]oxychromen-7-yl]oxyoxane-2-carboxylic acid —— C42H34O21
(2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-4-oxo-5-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carbonyl]oxychromen-7-yl]oxyoxane-2-carboxylic acid
—— 2-(4-Hydroxyphenyl)-7-[[5-(2-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one —— C25H18N2O5
2-(4-Hydroxyphenyl)-7-[[5-(2-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one
—— (2S)-5-hydroxy-2-[2-(7-hydroxy-3,7-dimethyloct-2-enyl)-3,4-dimethoxyphenyl]-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one —— C33H44O7
(2S)-5-hydroxy-2-[2-(7-hydroxy-3,7-dimethyloct-2-enyl)-3,4-dimethoxyphenyl]-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
—— 9-(5-bromo-2-methoxyphenyl)-4-chloro-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C26H20BrClN4O2
9-(5-bromo-2-methoxyphenyl)-4-chloro-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 5,7-Dimethoxy-2'-flavonyl 4-toluenesulfonate —— C24H20O7S
5,7-Dimethoxy-2'-flavonyl 4-toluenesulfonate
—— 7-decyl-2-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-one —— C25H32O6
7-decyl-2-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-one
—— 1-O-[2-[5-[[3-[3-[2-[4-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methoxy]-4-oxobutanoyl]oxyethoxy]propyl-dimethylsilyl]-2-methylbutan-2-yl]oxy-dimethylsilyl]-4,4,5-trimethylhexoxy]ethyl] 4-O-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methyl] butanedioate —— C91H112O17Si2
1-O-[2-[5-[[3-[3-[2-[4-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methoxy]-4-oxobutanoyl]oxyethoxy]propyl-dimethylsilyl]-2-methylbutan-2-yl]oxy-dimethylsilyl]-4,4,5-trimethylhexoxy]ethyl] 4-O-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methyl] butanedioate
—— 6-butyl-4-hydroxy-2-phenyl-4H-chromen-3-one —— C19H20O3
6-butyl-4-hydroxy-2-phenyl-4H-chromen-3-one
—— 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one —— C28H32O18
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
—— N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridin-2-amine —— C20H17N3O
N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridin-2-amine
—— 2-(4-hydroxy-3-methylphenyl)-5-methyl-3,4-dihydro-2H-chromene-3,7-diol —— C17H18O4
2-(4-hydroxy-3-methylphenyl)-5-methyl-3,4-dihydro-2H-chromene-3,7-diol
—— [7-Methyl-5-[4-(3-piperidin-1-ylpropoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate —— C36H41NO5
[7-Methyl-5-[4-(3-piperidin-1-ylpropoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate
—— 5,7-Dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-2-(2-methylphenyl)chromen-4-one;ethane —— C24H29NO5
5,7-Dihydroxy-8-(3-hydroxy-1-methylpiperidin-4-yl)-2-(2-methylphenyl)chromen-4-one;ethane
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2R,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C27H30O16
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2R,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— 2-(4-ethoxy-3-methoxyphenyl)-8-methoxy-3-nitro-2H-chromene —— C19H19NO6
2-(4-ethoxy-3-methoxyphenyl)-8-methoxy-3-nitro-2H-chromene
—— 5-[3,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl]peroxy-3,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C30H18O12
5-[3,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl]peroxy-3,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— 3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one —— C21H22O9
3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
—— 4-chloro-6-(7-chloro-6-hydroxy-1,2,3,9a-tetrahydro-3aH-spiro[cyclopenta[b]chromene-9,1'-cyclopentan]-3a-yl)benzene-1,3-diol —— C22H22Cl2O4
4-chloro-6-(7-chloro-6-hydroxy-1,2,3,9a-tetrahydro-3aH-spiro[cyclopenta[b]chromene-9,1'-cyclopentan]-3a-yl)benzene-1,3-diol
—— 3-[2-Hydroxy-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-8-yl]propanoic acid —— C32H33NO6
3-[2-Hydroxy-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-8-yl]propanoic acid
—— 4-chloro-9-(3,4-dimethoxyphenyl)-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C27H23ClN4O3
4-chloro-9-(3,4-dimethoxyphenyl)-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 9-(3,4-dimethoxyphenyl)-11-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C26H21FN4O3
9-(3,4-dimethoxyphenyl)-11-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 5-methoxy-2-(6'-methoxy-1',3',4',9a'-tetrahydrospiro[cyclohexane-1,9'-xanthen]-4a'(2'H)-yl)phenyl thiophene-2-carboxylate —— C31H34O5S
5-methoxy-2-(6'-methoxy-1',3',4',9a'-tetrahydrospiro[cyclohexane-1,9'-xanthen]-4a'(2'H)-yl)phenyl thiophene-2-carboxylate
—— (2S,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol —— C30H26O12
(2S,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
—— (2S,3S,4S)-2-[[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydrochromene-3,4,5,7-tetrol —— C30H26O14
(2S,3S,4S)-2-[[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-2-(3,4,5-trihydroxyphenyl)-3,4-dihydrochromene-3,4,5,7-tetrol
—— 4-methyl-3-(4-nitrosophenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-3,4-dihydro-2H-chromen-7-ol —— C29H32N2O4
4-methyl-3-(4-nitrosophenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-3,4-dihydro-2H-chromen-7-ol
—— 3-(2'-Amino-1'-methyl-5'-oxo-2-phenylspiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl)benzaldehyde —— C25H21N3O3
3-(2'-Amino-1'-methyl-5'-oxo-2-phenylspiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl)benzaldehyde
—— 3-bromo-4-[5,7-dihydroxy-8-[(2S,3R)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-4-oxochromen-2-yl]-N-hydroxybenzamide —— C22H21BrN2O7
3-bromo-4-[5,7-dihydroxy-8-[(2S,3R)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-4-oxochromen-2-yl]-N-hydroxybenzamide
—— (2R,3S)-2-(3,4-dihydroxyphenyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydrochromene-3,5,7-triol —— C21H24O12
(2R,3S)-2-(3,4-dihydroxyphenyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydrochromene-3,5,7-triol
—— [(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexyl] 2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxyacetate —— C23H22O14
[(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexyl] 2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxyacetate
—— (5,7-dihydroxy-2-phenyl-2H-chromen-4-yl)oxysulfamic acid —— C15H13NO7S
(5,7-dihydroxy-2-phenyl-2H-chromen-4-yl)oxysulfamic acid
—— Ethane;5-hydroxy-2-(4-methylphenyl)chromen-4-one —— C20H24O3
Ethane;5-hydroxy-2-(4-methylphenyl)chromen-4-one
—— 2-(2,6-dimethylocta-2,6-dien-3-yl)-2-phenyl-3H-chromen-4-one —— C25H28O2
2-(2,6-dimethylocta-2,6-dien-3-yl)-2-phenyl-3H-chromen-4-one
—— 1-[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydrochromen-2-yl]pentadecan-1-one —— C30H42O7
1-[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydrochromen-2-yl]pentadecan-1-one
—— 2-phenyl-2,3-bis[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H-chromen-4-one —— C27H32O12
2-phenyl-2,3-bis[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3H-chromen-4-one
—— ethyl (2S)-2-[[2-[5-(3,4-dimethoxyphenyl)-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl]acetyl]amino]-2-[(4-methylphenyl)sulfonylamino]acetate;ethyl 3-[[4-[2-[2-(3,4-dimethoxyphenyl)-4-oxochromen-3-yl]oxyethoxy]benzoyl]amino]-2-[(4-methylphenyl)sulfonylamino]propanoate —— C68H74N8O19S2
ethyl (2S)-2-[[2-[5-(3,4-dimethoxyphenyl)-1-methyl-7-oxo-3-propylpyrazolo[4,3-d]pyrimidin-6-yl]acetyl]amino]-2-[(4-methylphenyl)sulfonylamino]acetate;ethyl 3-[[4-[2-[2-(3,4-dimethoxyphenyl)-4-oxochromen-3-yl]oxyethoxy]benzoyl]amino]-2-[(4-methylphenyl)sulfonylamino]propanoate
—— 3,3-dimethyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazol-3-ium-5-carboxylic acid —— C19H19N2O3+
3,3-dimethyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazol-3-ium-5-carboxylic acid
—— 8-Methylflavan-3-ol —— C16H16O2
8-Methylflavan-3-ol
—— (6-Butanoyl-3-butanoyloxy-7-hydroxy-4-oxo-2-phenylchromen-5-yl) butanoate —— C27H28O8
(6-Butanoyl-3-butanoyloxy-7-hydroxy-4-oxo-2-phenylchromen-5-yl) butanoate
—— 2-(3,4-Dihydroxyphenyl)-5-hydroperoxy-7-hydroxy-3-[(4-oxo-2-phenyl-2,3-dihydrochromen-3-yl)peroxy]chromen-4-one —— C30H20O11
2-(3,4-Dihydroxyphenyl)-5-hydroperoxy-7-hydroxy-3-[(4-oxo-2-phenyl-2,3-dihydrochromen-3-yl)peroxy]chromen-4-one
—— 4-[2-[3-(3,4-dichlorophenyl)-4-[methyl-(4-oxo-2-phenylchromene-3-carbonyl)amino]butyl]piperidin-1-yl]-N,N-dimethylpiperidine-4-carboxamide —— C40H46Cl2N4O4
4-[2-[3-(3,4-dichlorophenyl)-4-[methyl-(4-oxo-2-phenylchromene-3-carbonyl)amino]butyl]piperidin-1-yl]-N,N-dimethylpiperidine-4-carboxamide
—— 2-(4-Hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one —— C24H17N3O5
2-(4-Hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one
—— (2R)-4-hydroxy-2-phenyl-4H-chromen-3-one —— C15H12O3
(2R)-4-hydroxy-2-phenyl-4H-chromen-3-one
—— 2'-Amino-6-(3-amino-5-methylphenyl)-3'-methyl-2-phenylspiro[2,3-dihydrochromene-4,5'-imidazole]-4'-one —— C25H24N4O2
2'-Amino-6-(3-amino-5-methylphenyl)-3'-methyl-2-phenylspiro[2,3-dihydrochromene-4,5'-imidazole]-4'-one
—— 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one —— C27H30O16
2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— N-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-N-pyridin-3-ylpropanamide —— C23H22N2O3
N-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-N-pyridin-3-ylpropanamide
—— 2-(3-Acetylphenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one —— C27H16F4N2O5
2-(3-Acetylphenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one
—— 2-Phenyl-5-sulfanylchromen-4-one —— C15H10O2S
2-Phenyl-5-sulfanylchromen-4-one