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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-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S)-3-hydroxy-1-methylpiperidin-2-yl]chromen-4-one —— C21H20ClNO5
2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S)-3-hydroxy-1-methylpiperidin-2-yl]chromen-4-one
—— [(3S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate —— C30H27O13+
[(3S,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
—— 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-sulfanyloxychromen-4-one —— C15H10O7S
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-sulfanyloxychromen-4-one
—— [2-(2-chlorophenyl)-5-hydroxy-8-[(3R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl] N-octadeca-9,12-dienylcarbamate —— C40H53ClN2O6
[2-(2-chlorophenyl)-5-hydroxy-8-[(3R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl] N-octadeca-9,12-dienylcarbamate
—— [5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-3-yl] 3,5-dihydroxy-4-methylbenzoate;2,2-dimethylpropane —— C38H54O11
[5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-3-yl] 3,5-dihydroxy-4-methylbenzoate;2,2-dimethylpropane
—— 5,7-dihydroxy-6-[(2R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-2-(4-hydroxyphenyl)chromen-4-one —— C27H28O13
5,7-dihydroxy-6-[(2R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-2-(4-hydroxyphenyl)chromen-4-one
—— 2-(3-formylphenyl)-7-methoxy-8-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-4-oxochromene-5-carbaldehyde —— C24H21NO5
2-(3-formylphenyl)-7-methoxy-8-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-4-oxochromene-5-carbaldehyde
—— ethane;(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-3,4-dihydro-2H-chromene-5,7-diol —— C21H30O6
ethane;(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-3,4-dihydro-2H-chromene-5,7-diol
—— 2,3',6-trimethyl-2'-methylsulfanyl-2-phenylspiro[3H-chromene-4,5'-imidazole]-4'-one —— C21H22N2O2S
2,3',6-trimethyl-2'-methylsulfanyl-2-phenylspiro[3H-chromene-4,5'-imidazole]-4'-one
—— methyl ({(4E)-2-(4-methoxyphenyl)-4-[(5-methyl-4-phenyl-1,3-thiazol-2-yl)imino]-4H-chromen-6-yl}oxy)acetate —— C29H24N2O5S
methyl ({(4E)-2-(4-methoxyphenyl)-4-[(5-methyl-4-phenyl-1,3-thiazol-2-yl)imino]-4H-chromen-6-yl}oxy)acetate
—— [3,6-Diacetyl-5-acetyloxy-2-(3,4-dihydroxyphenyl)-4-oxochromen-7-yl] acetate —— C23H18O10
[3,6-Diacetyl-5-acetyloxy-2-(3,4-dihydroxyphenyl)-4-oxochromen-7-yl] acetate
—— (2Z)-2-[2-(6-bromo-4H-1,3-benzodioxin-8-yl)-6-methoxy-2,3-dihydro-4H-chromen-4-ylidene]hydrazinecarbothioamide —— C19H18BrN3O4S
(2Z)-2-[2-(6-bromo-4H-1,3-benzodioxin-8-yl)-6-methoxy-2,3-dihydro-4H-chromen-4-ylidene]hydrazinecarbothioamide
—— 7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethyl-5-sulfanylchromen-4-one —— C19H18O6S
7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethyl-5-sulfanylchromen-4-one
—— 6-Ethyl-5-fluoro-16-methyl-10-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,5,7,11,13,16-hexaene-4,18-dione —— C24H17FO5
6-Ethyl-5-fluoro-16-methyl-10-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,5,7,11,13,16-hexaene-4,18-dione
—— 2-[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydrochromen-2-yl]-2-oxoacetic acid —— C17H14O9
2-[2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydrochromen-2-yl]-2-oxoacetic acid
—— [11-methyl-11-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5H-chromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate —— C34H37NO5
[11-methyl-11-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5H-chromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate
—— 2-(4-hydroxyphenyl)-5,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2,3-dihydrochromen-4-one —— C27H32O15
2-(4-hydroxyphenyl)-5,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-2,3-dihydrochromen-4-one
—— 2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one —— C21H20O10
2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one
—— 5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6-(3-phenylprop-2-enyl)chromen-4-one —— C26H22O7
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6-(3-phenylprop-2-enyl)chromen-4-one
—— 3-Hydrazinyl-2-phenylchromen-4-one —— C15H12N2O2
3-Hydrazinyl-2-phenylchromen-4-one
—— methyl 2-[(1S,5R,13S)-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-[(1S,5R,13S)-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
—— 3-Bromo-2-(4-methylsulfanylphenyl)chromen-4-one;ethane —— C20H23BrO2S
3-Bromo-2-(4-methylsulfanylphenyl)chromen-4-one;ethane
—— 6-ethyl-7-hydroxy-3-(1-methyl-1H-benzimidazol-2-yl)-2-(4-nitrophenyl)-4H-chromen-4-one —— C25H19N3O5
6-ethyl-7-hydroxy-3-(1-methyl-1H-benzimidazol-2-yl)-2-(4-nitrophenyl)-4H-chromen-4-one
—— 8,3'-Dimethoxy-5,4'-dihydroxyflavone —— C17H14O6
8,3'-Dimethoxy-5,4'-dihydroxyflavone
—— (2S)-2-phenyl-3,4-dihydrochromen-2-ol —— C15H14O2
(2S)-2-phenyl-3,4-dihydrochromen-2-ol
—— 2-(3,4-dihydro-2H-1,5-benzodioxepin-7-yl)-7-hydroxychromen-4-one —— C18H14O5
2-(3,4-dihydro-2H-1,5-benzodioxepin-7-yl)-7-hydroxychromen-4-one
—— 5-Hydroxy-2-[3-hydroxy-4-methoxy-2-(2-methylprop-2-enyl)phenyl]-6,8-bis(2-methylprop-2-enyl)chromen-4-one —— C28H30O5
5-Hydroxy-2-[3-hydroxy-4-methoxy-2-(2-methylprop-2-enyl)phenyl]-6,8-bis(2-methylprop-2-enyl)chromen-4-one
—— [5-methyl-5-[4-(2-piperidin-1-ylethoxy)phenyl]-11H-chromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate —— C35H39NO5
[5-methyl-5-[4-(2-piperidin-1-ylethoxy)phenyl]-11H-chromeno[4,3-c]chromen-2-yl] 2,2-dimethylpropanoate
—— 3-[(2'R)-2-amino-3',5'-dimethyl-5-oxo-2'-phenylspiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile —— C26H22N4O2
3-[(2'R)-2-amino-3',5'-dimethyl-5-oxo-2'-phenylspiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile
—— 2-(4-Hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one —— C25H15F3N2O5
2-(4-Hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one
—— (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-methoxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]oxane-2-carboxylic acid —— C22H20O13
(2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-methoxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]oxane-2-carboxylic acid
—— (3aR,4S,9bS)-8-methyl-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-2-one;trimethyl(trifluoromethyl)silane —— C24H29F3O2Si
(3aR,4S,9bS)-8-methyl-4-(4-methylphenyl)-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-2-one;trimethyl(trifluoromethyl)silane
—— (3Z)-2-phenyl-3-(thiophen-2-ylmethylidene)chromen-4-one —— C20H14O2S
(3Z)-2-phenyl-3-(thiophen-2-ylmethylidene)chromen-4-one
—— 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one —— C21H20O11
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— (2R)-2-(3,4-dimethoxyphenyl)-4,5-dihydroxy-7-methoxy-4H-chromen-3-one —— C18H18O7
(2R)-2-(3,4-dimethoxyphenyl)-4,5-dihydroxy-7-methoxy-4H-chromen-3-one
—— 8-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C26H28O16
8-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 3,7-Dihydroxy-2-phenyl-5-propoxychromen-4-one —— C18H16O5
3,7-Dihydroxy-2-phenyl-5-propoxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one —— C26H28O15
2-(3,4-dihydroxyphenyl)-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
—— 3-[(2'R)-2-amino-2'-(2-fluorophenyl)-3'-methyl-5-oxospiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile —— C25H19FN4O2
3-[(2'R)-2-amino-2'-(2-fluorophenyl)-3'-methyl-5-oxospiro[1H-imidazole-4,4'-2,3-dihydrochromene]-6'-yl]benzonitrile
—— Ethoxy-[[7-hydroxy-2-(3-hydroxy-4-methylphenyl)-4-oxochromen-3-yl]oxymethyl]phosphinic acid —— C19H19O8P
Ethoxy-[[7-hydroxy-2-(3-hydroxy-4-methylphenyl)-4-oxochromen-3-yl]oxymethyl]phosphinic acid
—— 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(2S,5S)-5-methylpyrrolidin-2-yl]chromen-4-one —— C20H19NO7
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(2S,5S)-5-methylpyrrolidin-2-yl]chromen-4-one
—— 5-hydroxy-3,6-dimethoxy-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one —— C23H24O15
5-hydroxy-3,6-dimethoxy-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
—— N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzenesulfonamide —— C21H18N2O3S
N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzenesulfonamide
—— [4-(3-hydroxy-3,4-dihydro-2H-chromen-2-yl)phenyl]methanediol —— C16H16O4
[4-(3-hydroxy-3,4-dihydro-2H-chromen-2-yl)phenyl]methanediol
—— [(2S,3S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-6-methyloxan-4-yl] 3-(4-hydroxyphenyl)prop-2-enoate —— C39H32O14
[(2S,3S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-6-methyloxan-4-yl] 3-(4-hydroxyphenyl)prop-2-enoate
—— [5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-4-oxochromen-7-yl] (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate —— C22H20O11
[5-hydroxy-2-(4-hydroxyphenyl)-3-methyl-4-oxochromen-7-yl] (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
—— 6-Butyl-16-methyl-10-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,5,7,11,13,16-hexaene-4,18-dione —— C26H22O5
6-Butyl-16-methyl-10-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,5,7,11,13,16-hexaene-4,18-dione
—— 7-Decyl-2-(3-hydroxy-4,5-dimethylphenyl)-3-methylchromen-4-one —— C28H36O3
7-Decyl-2-(3-hydroxy-4,5-dimethylphenyl)-3-methylchromen-4-one
—— (E)-2-cyano-N-(4-methylphenyl)-3-(2-phenyl-2H-chromen-3-yl)prop-2-enamide —— C26H20N2O2
(E)-2-cyano-N-(4-methylphenyl)-3-(2-phenyl-2H-chromen-3-yl)prop-2-enamide
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3R,4S,5S,6S)-3,4,5-trihydroxy-6-[2-hydroxy-2-(3,4,5-trihydroxyphenyl)acetyl]oxan-2-yl]oxychromen-4-one —— C28H24O15
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3R,4S,5S,6S)-3,4,5-trihydroxy-6-[2-hydroxy-2-(3,4,5-trihydroxyphenyl)acetyl]oxan-2-yl]oxychromen-4-one