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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
—— 3-(1H-indol-3-ylmethylidene)-2-phenylchromen-4-one —— C24H17NO2
3-(1H-indol-3-ylmethylidene)-2-phenylchromen-4-one
—— 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(2-phenylethenyl)-2,3-dihydrochromen-4-one —— C23H18O5
5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(2-phenylethenyl)-2,3-dihydrochromen-4-one
—— [2-Hydroxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]methyl-methylphosphinous acid —— C17H15O8P
[2-Hydroxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]methyl-methylphosphinous acid
—— 5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-diiodochromen-4-one —— C17H12I2O7
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-diiodochromen-4-one
—— 2-(2-Chloro-5-fluorophenyl)-8-[[hydroxy(1,3-thiazol-4-yl)methyl]amino]chromen-4-one —— C19H12ClFN2O3S
2-(2-Chloro-5-fluorophenyl)-8-[[hydroxy(1,3-thiazol-4-yl)methyl]amino]chromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[3,4,5-trihydroxy-6-[2-(3,4,5-trihydroxy-6-methyloxan-2-yl)ethyl]oxan-2-yl]oxychromen-4-one —— C28H32O15
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[3,4,5-trihydroxy-6-[2-(3,4,5-trihydroxy-6-methyloxan-2-yl)ethyl]oxan-2-yl]oxychromen-4-one
—— [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] methyl sulfate —— C16H16O9S
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] methyl sulfate
—— 3-Non-2-enyl-2-(2,4,5-trimethoxyphenyl)chromen-4-one —— C27H32O5
3-Non-2-enyl-2-(2,4,5-trimethoxyphenyl)chromen-4-one
—— 7-Methoxy-2-(3,4,5-trimethoxyphenyl)chromenylium —— C19H19O5+
7-Methoxy-2-(3,4,5-trimethoxyphenyl)chromenylium
—— (2S)-7-[(1R,2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(1R,2R,3R,4S,5R)-2,3,4-trihydroxy-5-methylcyclohexyl]oxycyclohexyl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one —— C29H36O12
(2S)-7-[(1R,2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(1R,2R,3R,4S,5R)-2,3,4-trihydroxy-5-methylcyclohexyl]oxycyclohexyl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
—— ethane;(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol —— C18H22O6
ethane;(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2-(2,3-Dimethoxyphenyl)-7-hydroxy-3,5,6,8-tetramethoxychromen-4-one —— C21H22O9
2-(2,3-Dimethoxyphenyl)-7-hydroxy-3,5,6,8-tetramethoxychromen-4-one
—— 2-amino-1-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3-sulfanylpropan-1-one —— C18H19NO7S
2-amino-1-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3-sulfanylpropan-1-one
—— 2,2-Dimethylpropane;3,5,7-trihydroxy-2-(3-hydroxy-4-methylphenyl)chromen-4-one —— C26H36O6
2,2-Dimethylpropane;3,5,7-trihydroxy-2-(3-hydroxy-4-methylphenyl)chromen-4-one
—— 7-[[(1S,4R,5S)-4,8-dihydroxy-7-oxo-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-5,6-dihydroxy-2-phenylchromen-4-one —— C21H16O10
7-[[(1S,4R,5S)-4,8-dihydroxy-7-oxo-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-5,6-dihydroxy-2-phenylchromen-4-one
—— 2-(3-Methoxyphenyl)-6-methyl-2'-sulfanylidenespiro[2,3-dihydrochromene-4,5'-imidazolidine]-4'-one —— C19H18N2O3S
2-(3-Methoxyphenyl)-6-methyl-2'-sulfanylidenespiro[2,3-dihydrochromene-4,5'-imidazolidine]-4'-one
—— 2-(3,4-Dihydroxyphenyl)-3-[[ethoxy(prop-2-enoxy)phosphoryl]methoxy]-7-hydroxy-5-methylchromen-4-one —— C22H23O9P
2-(3,4-Dihydroxyphenyl)-3-[[ethoxy(prop-2-enoxy)phosphoryl]methoxy]-7-hydroxy-5-methylchromen-4-one
—— 2-(3-Hydroxy-4-methylphenyl)-3,7-dimethylchromen-4-one —— C18H16O3
2-(3-Hydroxy-4-methylphenyl)-3,7-dimethylchromen-4-one
—— [2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] pentanoate —— C20H18O8
[2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] pentanoate
—— [(3S,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate —— C31H28O13
[(3S,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
—— 3-methyl-N-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-N-pyridin-3-ylbutanamide —— C25H26N2O3
3-methyl-N-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-N-pyridin-3-ylbutanamide
—— 3-Bromo-5,7-dihydroxy-2-phenylchromen-4-one —— C15H9BrO4
3-Bromo-5,7-dihydroxy-2-phenylchromen-4-one
—— (2S)-2-[3,4-dihydroxy-5-(7-hydroxy-3,7-dimethyloct-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C25H30O7
(2S)-2-[3,4-dihydroxy-5-(7-hydroxy-3,7-dimethyloct-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— (2R,3R,4S)-4-[2,6-dihydroxy-4-[2-(4-hydroxyphenyl)ethenyl]phenyl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol —— C29H24O9
(2R,3R,4S)-4-[2,6-dihydroxy-4-[2-(4-hydroxyphenyl)ethenyl]phenyl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2-phenyl-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R,2S,3R,4R)-1,2,3,4-tetrahydroxypentyl]oxan-2-yl]oxychromen-4-one —— C25H28O11
2-phenyl-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R,2S,3R,4R)-1,2,3,4-tetrahydroxypentyl]oxan-2-yl]oxychromen-4-one
—— [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate —— C24H20O9
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
—— 5-[1-[3-chloro-4-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]but-1-enyl]-4-hydroxy-3H-1,3-thiazol-2-one —— C34H32ClNO10S
5-[1-[3-chloro-4-[2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyethoxy]phenyl]but-1-enyl]-4-hydroxy-3H-1,3-thiazol-2-one
—— 2-phenyl-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O8
2-phenyl-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxan-2-yl]oxychromen-4-one —— C27H30O15
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxan-2-yl]oxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O11
2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 5-hydroxy-2-[3-hydroxy-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,7-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one —— C33H40O22
5-hydroxy-2-[3-hydroxy-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,7-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
—— Ethyl 2-[[2-(1,3-benzodioxol-5-yl)-6-methyl-4-oxo-2,3-dihydrochromen-3-yl]oxycarbonylamino]acetate —— C22H21NO8
Ethyl 2-[[2-(1,3-benzodioxol-5-yl)-6-methyl-4-oxo-2,3-dihydrochromen-3-yl]oxycarbonylamino]acetate
—— N-butyl-3-(2'-ethyl-1'-methyl-5'-oxo-2-phenylspiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl)benzamide —— C31H33N3O3
N-butyl-3-(2'-ethyl-1'-methyl-5'-oxo-2-phenylspiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl)benzamide
—— methyl 2-[(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]-4-methylbenzenesulfonate —— C18H20O5S
methyl 2-[(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]-4-methylbenzenesulfonate
—— (2S)-2-[3,4-dihydroxy-2-(7-hydroxy-3,7-dimethyloct-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C25H30O7
(2S)-2-[3,4-dihydroxy-2-(7-hydroxy-3,7-dimethyloct-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— [2-(3,4-Dihydroxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxymethylphosphonous acid —— C16H13O8P
[2-(3,4-Dihydroxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxymethylphosphonous acid
—— 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one —— C29H34O19
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-bis[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-3-[[ethoxy(methyl)phosphoryl]methoxy]chromen-4-one —— C19H19O7P
2-(3,4-Dihydroxyphenyl)-3-[[ethoxy(methyl)phosphoryl]methoxy]chromen-4-one
—— [3-[(2R)-2'-amino-2-methyl-2-phenylspiro[3H-chromene-4,4'-imidazole]-6-yl]phenyl]methanol —— C25H23N3O2
[3-[(2R)-2'-amino-2-methyl-2-phenylspiro[3H-chromene-4,4'-imidazole]-6-yl]phenyl]methanol
—— 3-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxolan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C26H28O14
3-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxolan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— (2R,3S)-2-(3,4-dihydroxyphenyl)-2-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxan-2-yl]-3,4-dihydrochromene-3,5,7-triol —— C27H34O16
(2R,3S)-2-(3,4-dihydroxyphenyl)-2-[(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxan-2-yl]-3,4-dihydrochromene-3,5,7-triol
—— 2,3,5,6,7-pentahydroxy-2-(4-hydroxyphenyl)-3H-chromen-4-one —— C15H12O8
2,3,5,6,7-pentahydroxy-2-(4-hydroxyphenyl)-3H-chromen-4-one
—— 3-Chloro-3-methyl-2-(3-methyl-4-phenylmethoxyphenyl)-8-prop-2-enyl-2,4-dihydrochromen-4-ol —— C27H27ClO3
3-Chloro-3-methyl-2-(3-methyl-4-phenylmethoxyphenyl)-8-prop-2-enyl-2,4-dihydrochromen-4-ol
—— [2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate —— C28H28O15
[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
—— 2-(3,4-Dihydroxyphenyl)-3-methoxychromenylium-5,7-diol —— C16H13O6+
2-(3,4-Dihydroxyphenyl)-3-methoxychromenylium-5,7-diol
—— 2-(3,4-Dimethoxyphenyl)-3,5-dihydroxy-7-(3,4,5-trihydroxyoxan-2-yl)oxychromen-4-one —— C22H22O11
2-(3,4-Dimethoxyphenyl)-3,5-dihydroxy-7-(3,4,5-trihydroxyoxan-2-yl)oxychromen-4-one
—— 3-[2-[4-(1,1-difluoroprop-2-enoxy)phenyl]-4'-methyl-5'-propylspiro[2,3-dihydrochromene-4,2'-5H-1,3-oxazole]-6-yl]benzonitrile —— C31H28F2N2O3
3-[2-[4-(1,1-difluoroprop-2-enoxy)phenyl]-4'-methyl-5'-propylspiro[2,3-dihydrochromene-4,2'-5H-1,3-oxazole]-6-yl]benzonitrile
—— 2-(3-Benzylphenyl)chromenylium-7-ol —— C22H17O2+
2-(3-Benzylphenyl)chromenylium-7-ol
—— 2-(4-Acetylphenyl)-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one —— C18H16O5
2-(4-Acetylphenyl)-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one
—— [2,2-Bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methyl 12-[2-[13-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methoxy]-2,3-dimethyl-13-oxotridecoxy]propan-2-yl-dimethylsilyl]oxy-11,11,12-trimethyltridecanoate —— C94H120O12Si
[2,2-Bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methyl 12-[2-[13-[[2,2-bis(4-methoxyphenyl)-6-methylbenzo[h]chromen-5-yl]methoxy]-2,3-dimethyl-13-oxotridecoxy]propan-2-yl-dimethylsilyl]oxy-11,11,12-trimethyltridecanoate