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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
—— 8-<3-{4-[2-methoxy-5-(2,2,2-trifluoroethoxy)-phenyl]-1-piperazinyl}-propylcarbamoyl>-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran 335087-58-6 C33H34F3N3O5
8-<3-{4-[2-methoxy-5-(2,2,2-trifluoroethoxy)-phenyl]-1-piperazinyl}-propylcarbamoyl>-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran
—— [(2S,3R,4S,5R,6R)-3-(2-ethoxyacetyl)oxy-5-hydroxy-2-[3-hydroxy-2-[3-(4-methoxyphenyl)propanoyl]phenoxy]-6-(hydroxymethyl)oxan-4-yl] 2-ethoxyacetate —— C30H38O13
[(2S,3R,4S,5R,6R)-3-(2-ethoxyacetyl)oxy-5-hydroxy-2-[3-hydroxy-2-[3-(4-methoxyphenyl)propanoyl]phenoxy]-6-(hydroxymethyl)oxan-4-yl] 2-ethoxyacetate
—— [2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] nonadecanoate —— C34H46O8
[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] nonadecanoate
—— 2-phenyl-3-[3-[4-[(5S)-2-pyridin-3-yl-1,3-thiazolidine-5-carbonyl]piperazin-1-yl]propoxy]chromen-4-one —— C31H32N4O4S
2-phenyl-3-[3-[4-[(5S)-2-pyridin-3-yl-1,3-thiazolidine-5-carbonyl]piperazin-1-yl]propoxy]chromen-4-one
—— sideroxylonal B —— C26H28O10
sideroxylonal B
—— 10-Methoxy-2,2,4-trimethyl-5-[3-(methylsulfinylmethoxy)phenyl]-1,5-dihydrochromeno[3,4-f]quinoline —— C28H29NO4S
10-Methoxy-2,2,4-trimethyl-5-[3-(methylsulfinylmethoxy)phenyl]-1,5-dihydrochromeno[3,4-f]quinoline
—— 2-(4-Methylsulfonylphenyl)-3-(1,3-thiazol-2-yl)chromen-4-one —— C19H13NO4S2
2-(4-Methylsulfonylphenyl)-3-(1,3-thiazol-2-yl)chromen-4-one
—— 7-carboxymethoxy-5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4H-1-benzo-pyran-4-one —— C21H20O8
7-carboxymethoxy-5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4H-1-benzo-pyran-4-one
—— 8-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-4-one —— C17H14O6
8-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-4-one
—— 7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C27H30O14
7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— (2R,3S,10R)-10-(3,4-dihydroxyphenyl)-3,5-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one —— C24H20O10
(2R,3S,10R)-10-(3,4-dihydroxyphenyl)-3,5-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one
—— N-cyclopropyl-3-methyl-N-[(2S)-3-methylbutan-2-yl]-4-oxo-2-phenylchromene-8-carboxamide —— C25H27NO3
N-cyclopropyl-3-methyl-N-[(2S)-3-methylbutan-2-yl]-4-oxo-2-phenylchromene-8-carboxamide
—— N-[(3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide —— C30H28N2O3
N-[(3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
—— 4-(7-hydroxy-4-methyl-3,4-dihydro-2H-chromen-2-yl)benzene-1,3-diol —— C16H16O4
4-(7-hydroxy-4-methyl-3,4-dihydro-2H-chromen-2-yl)benzene-1,3-diol
—— 5,7,3′,4′,-pentahydroxyflavone —— C15H10O6
5,7,3′,4′,-pentahydroxyflavone
—— 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one;(Z)-1-N'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine —— C28H32N4O10S
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one;(Z)-1-N'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
—— 3-(4-hydroxyphenyl)-4-methyl-2-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-2H-chromene-7-ol —— C28H29NO4
3-(4-hydroxyphenyl)-4-methyl-2-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-2H-chromene-7-ol
—— (2S,3S)-7-Hydroxy-3-(4-hydroxy-phenyl)-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-chroman-4-one —— C28H29NO5
(2S,3S)-7-Hydroxy-3-(4-hydroxy-phenyl)-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-chroman-4-one
—— N-[(2R)-1-(furan-2-yl)propan-2-yl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide —— C24H21NO4
N-[(2R)-1-(furan-2-yl)propan-2-yl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
—— (2S)-7-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one —— C28H34O15
(2S)-7-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
—— (2S)-7-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one —— C28H34O15
(2S)-7-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
—— (2S)-1-(3-methyl-4-oxo-2-phenylchromene-8-carbonyl)-N-(1,3-thiazol-2-yl)pyrrolidine-2-carboxamide —— C25H21N3O4S
(2S)-1-(3-methyl-4-oxo-2-phenylchromene-8-carbonyl)-N-(1,3-thiazol-2-yl)pyrrolidine-2-carboxamide
—— (NE)-N-[6,8-dichloro-2-(3,4-dimethoxyphenyl)chromen-4-ylidene]hydroxylamine —— C17H13Cl2NO4
(NE)-N-[6,8-dichloro-2-(3,4-dimethoxyphenyl)chromen-4-ylidene]hydroxylamine
—— N-[(E)-[6,8-dichloro-2-(4-methoxyphenyl)chromen-4-ylidene]amino]aniline —— C22H16Cl2N2O2
N-[(E)-[6,8-dichloro-2-(4-methoxyphenyl)chromen-4-ylidene]amino]aniline
—— N-[(1R)-1-(2,4-dimethoxyphenyl)ethyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide —— C27H25NO5
N-[(1R)-1-(2,4-dimethoxyphenyl)ethyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
—— N-[(1S)-1-(2,4-dimethoxyphenyl)ethyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide —— C27H25NO5
N-[(1S)-1-(2,4-dimethoxyphenyl)ethyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5R,6R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one —— C27H28O14
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5R,6R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-8-[(2R,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one —— C25H26O13
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-8-[(2R,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one —— C27H28O14
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-8-[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one —— C25H26O13
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-8-[(2S,3S,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5R,6S)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one —— C27H28O14
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5R,6S)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5S,6R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one —— C27H28O14
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,5S,6R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one
—— (2E)-2-{[2-(3,4-dimethoxyphenyl)-4-phenyl-4H-chromen-3-yl]methylidene}-1,1-diphenylhydrazine —— C36H30N2O3
(2E)-2-{[2-(3,4-dimethoxyphenyl)-4-phenyl-4H-chromen-3-yl]methylidene}-1,1-diphenylhydrazine
—— N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridine-2-carboxamide —— C21H17N3O2
N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridine-2-carboxamide
—— (4E)-6,8-dichloro-N-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-imine —— C15H11Cl2NO2
(4E)-6,8-dichloro-N-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-imine
—— 2-(4-Chloro-phenyl)-chroman-4-one oxime 71906-97-3 C15H12ClNO2
2-(4-Chloro-phenyl)-chroman-4-one oxime
—— (E)-6-methoxy-2-phenyl-N-(1,3,4-thiadiazol-2-yl)chromen-4-imine —— C18H13N3O2S
(E)-6-methoxy-2-phenyl-N-(1,3,4-thiadiazol-2-yl)chromen-4-imine
—— (E)-6-methoxy-2-(4-methoxyphenyl)-N-(6-nitro-1,3-benzothiazol-2-yl)chromen-4-imine —— C24H17N3O5S
(E)-6-methoxy-2-(4-methoxyphenyl)-N-(6-nitro-1,3-benzothiazol-2-yl)chromen-4-imine
—— (E)-6-chloro-2-(4-methoxyphenyl)-N-(1,3-thiazol-2-yl)chromen-4-imine —— C19H13ClN2O2S
(E)-6-chloro-2-(4-methoxyphenyl)-N-(1,3-thiazol-2-yl)chromen-4-imine
—— ethyl 2-[(E)-(6-methoxy-2-phenylchromen-4-ylidene)amino]-4-methyl-1,3-thiazole-5-carboxylate —— C23H20N2O4S
ethyl 2-[(E)-(6-methoxy-2-phenylchromen-4-ylidene)amino]-4-methyl-1,3-thiazole-5-carboxylate
—— 2-[(E)-[2-(3,4-dimethoxyphenyl)-6-methoxychromen-4-ylidene]amino]-N,N,4-trimethyl-1,3-thiazole-5-carboxamide —— C25H25N3O5S
2-[(E)-[2-(3,4-dimethoxyphenyl)-6-methoxychromen-4-ylidene]amino]-N,N,4-trimethyl-1,3-thiazole-5-carboxamide
—— methyl 2-[(E)-[6-methoxy-2-(4-methoxyphenyl)chromen-4-ylidene]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate —— C27H25NO5S
methyl 2-[(E)-[6-methoxy-2-(4-methoxyphenyl)chromen-4-ylidene]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
—— N-[(Z)-[2-(3,4-dimethoxyphenyl)chromen-4-ylidene]amino]-1H-benzimidazol-2-amine —— C24H20N4O3
N-[(Z)-[2-(3,4-dimethoxyphenyl)chromen-4-ylidene]amino]-1H-benzimidazol-2-amine
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one —— C27H30O15
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one —— C27H30O15
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one —— C26H28O14
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— (2S)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O11
(2S)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one —— C27H30O15
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
—— 7-[(2R,3R,4R,5S,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C26H28O14
7-[(2R,3R,4R,5S,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— 7-[(2S,3R,4R,5S,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C26H28O14
7-[(2S,3R,4R,5S,6S)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one