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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
—— 2'-amino-3'-methyl-6-(3-methylcycloocta-1,5,7-trien-1-yl)-2-phenylspiro[2,3-dihydrochromene-4,6'-5H-pyrimidine]-4'-one —— C28H29N3O2
2'-amino-3'-methyl-6-(3-methylcycloocta-1,5,7-trien-1-yl)-2-phenylspiro[2,3-dihydrochromene-4,6'-5H-pyrimidine]-4'-one
—— Carbamoyl 8-methoxy-2,3-dimethyl-8-(2-methylphenyl)-6,7-dihydropyrano[2,3-e]benzimidazole-5-carboxylate —— C22H23N3O5
Carbamoyl 8-methoxy-2,3-dimethyl-8-(2-methylphenyl)-6,7-dihydropyrano[2,3-e]benzimidazole-5-carboxylate
—— (2'R,4S)-2-amino-6'-bromo-2'-phenyl-2'-propylspiro[1H-imidazole-4,4'-3H-chromene]-5-one —— C20H20BrN3O2
(2'R,4S)-2-amino-6'-bromo-2'-phenyl-2'-propylspiro[1H-imidazole-4,4'-3H-chromene]-5-one
—— 2-[4-Methyl-3-(2-methylpropoxy)phenyl]-3-phenylmethoxychromen-4-one —— C27H26O4
2-[4-Methyl-3-(2-methylpropoxy)phenyl]-3-phenylmethoxychromen-4-one
—— 2-acetyl-5-[5-formyl-7-methoxy-8-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-4-oxochromen-2-yl]benzene-1,3-dicarbaldehyde —— C27H23NO7
2-acetyl-5-[5-formyl-7-methoxy-8-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-4-oxochromen-2-yl]benzene-1,3-dicarbaldehyde
—— 2-[3-[Ethoxy(methyl)phosphoryl]peroxy-4-hydroxyphenyl]-3,7-dihydroxychromen-4-one —— C18H17O9P
2-[3-[Ethoxy(methyl)phosphoryl]peroxy-4-hydroxyphenyl]-3,7-dihydroxychromen-4-one
—— [11-[4-(2-Piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate —— C34H37NO5
[11-[4-(2-Piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate
—— (2S)-5,7-dihydroxy-2-[3-(3-hydroxy-3-methylbut-1-enyl)-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one —— C26H30O6
(2S)-5,7-dihydroxy-2-[3-(3-hydroxy-3-methylbut-1-enyl)-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
—— (6,7-dihydroxy-4-oxo-2-phenylchromen-5-yl) (2S,3S,4S,5R)-3,4,5-trihydroxy-6-sulfooxyoxane-2-carboxylate —— C21H18O14S
(6,7-dihydroxy-4-oxo-2-phenylchromen-5-yl) (2S,3S,4S,5R)-3,4,5-trihydroxy-6-sulfooxyoxane-2-carboxylate
—— 2-[3-[[Ethoxy(hexoxy)phosphoryl]methoxy]-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one —— C24H29O10P
2-[3-[[Ethoxy(hexoxy)phosphoryl]methoxy]-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one
—— (3R,4S,5S,6R)-2-[3-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C28H33O16+
(3R,4S,5S,6R)-2-[3-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— 4,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-3-one —— C17H16O7
4,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-3-one
—— 4-bromo-3-[5,7-dihydroxy-8-[(2S,3R)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-4-oxochromen-2-yl]benzoic acid —— C22H20BrNO7
4-bromo-3-[5,7-dihydroxy-8-[(2S,3R)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-4-oxochromen-2-yl]benzoic acid
—— 1-[2,3-dimethyl-8-(2-methylphenyl)-7,8-dihydro-6H-pyrano[2,3-e]benzimidazol-5-yl]pyrrolidin-2-one —— C23H25N3O2
1-[2,3-dimethyl-8-(2-methylphenyl)-7,8-dihydro-6H-pyrano[2,3-e]benzimidazol-5-yl]pyrrolidin-2-one
—— N-[3-[8-(methanesulfonamido)-1-methoxy-6H-benzo[c]chromen-6-yl]phenyl]propanamide —— C24H24N2O5S
N-[3-[8-(methanesulfonamido)-1-methoxy-6H-benzo[c]chromen-6-yl]phenyl]propanamide
—— [7-Hydroxy-2-(4-hydroxyphenyl)-6-octadecanoyl-3-octadecanoyloxy-4-oxochromen-5-yl] octadecanoate —— C69H112O9
[7-Hydroxy-2-(4-hydroxyphenyl)-6-octadecanoyl-3-octadecanoyloxy-4-oxochromen-5-yl] octadecanoate
—— 6-Brom-2-o-chlorphenyl-3-nitro-Δ<sup>3</sup>-chromen 57665-66-4 C15H9BrClNO3
6-Brom-2-o-chlorphenyl-3-nitro-Δ<sup>3</sup>-chromen
—— [(3S,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate —— C36H36O18
[(3S,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
—— 2-[[(2-acetamidoacetyl)-[6-[(4-oxo-2-phenyl-2,3-dihydrochromen-7-yl)oxy]pyridin-3-yl]amino]-acetylamino]-N-[6-[(4-oxo-2-phenyl-2,3-dihydrochromen-6-yl)oxy]pyridin-3-yl]acetamide —— C48H40N6O10
2-[[(2-acetamidoacetyl)-[6-[(4-oxo-2-phenyl-2,3-dihydrochromen-7-yl)oxy]pyridin-3-yl]amino]-acetylamino]-N-[6-[(4-oxo-2-phenyl-2,3-dihydrochromen-6-yl)oxy]pyridin-3-yl]acetamide
—— (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)-2-(difluoromethylidene)-8-methyl-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromene;[difluoromethyl(phenyl)phosphoryl]benzene —— C64H75F4O6PSi2
(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)-2-(difluoromethylidene)-8-methyl-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromene;[difluoromethyl(phenyl)phosphoryl]benzene
—— 6-bromo-2-(3-methoxy-4-propoxyphenyl)-3-nitro-2H-chromene —— C19H18BrNO5
6-bromo-2-(3-methoxy-4-propoxyphenyl)-3-nitro-2H-chromene
—— (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[(2S,4S,5R)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene —— C70H66O10
(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[(2S,4S,5R)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene
—— 6-(3-Ethylphenyl)-4-methylidene-2-phenyl-2,3-dihydrochromene —— C24H22O
6-(3-Ethylphenyl)-4-methylidene-2-phenyl-2,3-dihydrochromene
—— methyl 2-[(1R,5R,13R)-5,13-bis(3,4-dihydroxyphenyl)-18-nitro-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15(20),16,18-hexaen-1-yl]acetate —— C33H27NO11
methyl 2-[(1R,5R,13R)-5,13-bis(3,4-dihydroxyphenyl)-18-nitro-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15(20),16,18-hexaen-1-yl]acetate
—— 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylic acid;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylate —— C51H42O12
2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylic acid;methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-methyl-2H-chromene-3-carboxylate
—— 5-[1-[2-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]ethenyl]-4-hydroxy-3H-1,3-thiazol-2-one —— C32H29NO10S
5-[1-[2-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]ethenyl]-4-hydroxy-3H-1,3-thiazol-2-one
—— 4-(4-acetylphenoxy)butyl prop-2-enoate;(2S,3S)-2-(3,4-dimethylphenyl)-3,5,7-trimethyl-3,4-dihydro-2H-chromene;6-[4-[4-(2-methyloctanoyl)benzoyl]phenoxy]hexyl prop-2-enoate —— C81H100O14
4-(4-acetylphenoxy)butyl prop-2-enoate;(2S,3S)-2-(3,4-dimethylphenyl)-3,5,7-trimethyl-3,4-dihydro-2H-chromene;6-[4-[4-(2-methyloctanoyl)benzoyl]phenoxy]hexyl prop-2-enoate
—— N-[[3-[8-(methanesulfonamido)-1-methoxy-6H-benzo[c]chromen-6-yl]phenyl]methyl]benzenesulfonamide —— C28H26N2O6S2
N-[[3-[8-(methanesulfonamido)-1-methoxy-6H-benzo[c]chromen-6-yl]phenyl]methyl]benzenesulfonamide
—— 2-[5-(3,7-Dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]acetaldehyde —— C17H12O7
2-[5-(3,7-Dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]acetaldehyde
—— 2'-Amino-6-methyl-2-phenyl-3'-propylspiro[2,3-dihydrochromene-4,5'-imidazole]-4'-one —— C21H23N3O2
2'-Amino-6-methyl-2-phenyl-3'-propylspiro[2,3-dihydrochromene-4,5'-imidazole]-4'-one
—— 2,2-dimethylpropane;2-(3-hydroxy-4-methylphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol —— C26H40O5
2,2-dimethylpropane;2-(3-hydroxy-4-methylphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— Ethane;3-methyl-2-phenylchromenylium —— C24H37O+
Ethane;3-methyl-2-phenylchromenylium
—— Cyclohexyl 2-[2-(4-methoxyphenyl)-4-oxochromen-6-yl]oxypropanoate —— C25H26O6
Cyclohexyl 2-[2-(4-methoxyphenyl)-4-oxochromen-6-yl]oxypropanoate
—— Carbamoyl 8-methoxy-2,3-dimethyl-8-phenyl-6,7-dihydropyrano[2,3-e]benzimidazole-5-carboxylate —— C21H21N3O5
Carbamoyl 8-methoxy-2,3-dimethyl-8-phenyl-6,7-dihydropyrano[2,3-e]benzimidazole-5-carboxylate
—— (2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-(2-methylbut-3-en-2-yl)-2,3-dihydrochromen-4-one —— C20H20O6
(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-(2-methylbut-3-en-2-yl)-2,3-dihydrochromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-3-ethyl-5,7-dihydroperoxy-6-hydroxychromen-4-one —— C17H14O9
2-(3,4-Dihydroxyphenyl)-3-ethyl-5,7-dihydroperoxy-6-hydroxychromen-4-one
—— 6-hydroxy-2-phenyl-5,7-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one —— C27H30O15
6-hydroxy-2-phenyl-5,7-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
—— (2S,3S,4S,5R)-6-[4-[3-(2,4-dihydroxy-6-sulfooxyphenyl)-3-oxopropyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid —— C21H22O14S
(2S,3S,4S,5R)-6-[4-[3-(2,4-dihydroxy-6-sulfooxyphenyl)-3-oxopropyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
—— (5-Ethoxy-3-hydroxy-4-oxo-2-phenylchromen-7-yl)oxymethyl-methylphosphinic acid —— C19H19O7P
(5-Ethoxy-3-hydroxy-4-oxo-2-phenylchromen-7-yl)oxymethyl-methylphosphinic acid
—— 7-[3,4-dihydroxy-6-(hydroxymethyl)-5-[(4R)-3,7,11,15-tetramethylhexadec-2-en-4-yl]oxyoxan-2-yl]oxy-2-(3,4-dimethoxyphenyl)-3,5-dihydroxychromen-4-one —— C43H62O12
7-[3,4-dihydroxy-6-(hydroxymethyl)-5-[(4R)-3,7,11,15-tetramethylhexadec-2-en-4-yl]oxyoxan-2-yl]oxy-2-(3,4-dimethoxyphenyl)-3,5-dihydroxychromen-4-one
—— Ethane;3-methyl-2-(4-methylphenyl)chromen-4-one —— C19H20O2
Ethane;3-methyl-2-(4-methylphenyl)chromen-4-one
—— 3-[2-Hydroxy-11-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-8-yl]propanoic acid —— C32H33NO6
3-[2-Hydroxy-11-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-8-yl]propanoic acid
—— 8-[[Hydroxy(1,3-thiazol-4-yl)methyl]amino]-2-phenylchromen-4-one —— C19H14N2O3S
8-[[Hydroxy(1,3-thiazol-4-yl)methyl]amino]-2-phenylchromen-4-one
—— (2S)-2-[2-(3,7-dimethylocta-2,6-dienyl)-3,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C25H28O6
(2S)-2-[2-(3,7-dimethylocta-2,6-dienyl)-3,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— [7-Hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl] hydrogen sulfate —— C15H10O8S
[7-Hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl] hydrogen sulfate
—— [3-(4-hydroxy-3-methoxyphenyl)-6-(4,5,7-trihydroxy-3-oxo-4H-chromen-2-yl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 2-ethoxybenzoate —— C34H30O12
[3-(4-hydroxy-3-methoxyphenyl)-6-(4,5,7-trihydroxy-3-oxo-4H-chromen-2-yl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 2-ethoxybenzoate
—— 2-ethyl-3-methyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxylic acid —— C20H20N2O3
2-ethyl-3-methyl-8-phenyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxylic acid
—— 2-(2-Chlorophenyl)-8-[[hydroxy-(2-methylpyrazol-3-yl)methyl]amino]chromen-4-one —— C20H16ClN3O3
2-(2-Chlorophenyl)-8-[[hydroxy-(2-methylpyrazol-3-yl)methyl]amino]chromen-4-one
—— 8-[4-Methyl-3-(4-oxochromen-2-yl)cyclohepta-1,3,6-trien-1-yl]-2-phenylchromen-4-one —— C32H22O4
8-[4-Methyl-3-(4-oxochromen-2-yl)cyclohepta-1,3,6-trien-1-yl]-2-phenylchromen-4-one
—— 5,5-Bis(4-methoxyphenyl)-18-morpholin-4-yl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaen-21-one —— C38H31NO5
5,5-Bis(4-methoxyphenyl)-18-morpholin-4-yl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaen-21-one