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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
—— [(2S,5R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-[3-(4-hydroxy-3-methylphenyl)prop-2-enoyloxymethyl]oxan-4-yl] 3-(4-hydroxyphenyl)prop-2-enoate —— C40H34O15
[(2S,5R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-[3-(4-hydroxy-3-methylphenyl)prop-2-enoyloxymethyl]oxan-4-yl] 3-(4-hydroxyphenyl)prop-2-enoate
—— [2-(2,4-Dihydroxyphenyl)-6-dodecanoyl-3,5-di(dodecanoyloxy)-4-oxochromen-7-yl] dodecanoate —— C63H98O11
[2-(2,4-Dihydroxyphenyl)-6-dodecanoyl-3,5-di(dodecanoyloxy)-4-oxochromen-7-yl] dodecanoate
—— (2S)-2-[2-(3,7-dimethyl-7-phenylsulfanyloct-2-enyl)-3,4-dimethoxyphenyl]-6-(3-hydroxy-3-phenylsulfanylbutyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one —— C45H54O7S2
(2S)-2-[2-(3,7-dimethyl-7-phenylsulfanyloct-2-enyl)-3,4-dimethoxyphenyl]-6-(3-hydroxy-3-phenylsulfanylbutyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-3-ethoxychromen-4-one —— C17H14O5
2-(3,4-Dihydroxyphenyl)-3-ethoxychromen-4-one
—— N-[6-[[(2S)-2-[3-(5-nitropyridin-2-yl)oxyphenyl]-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]pyrrolidine-2-carboxamide —— C30H27N5O6
N-[6-[[(2S)-2-[3-(5-nitropyridin-2-yl)oxyphenyl]-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]pyrrolidine-2-carboxamide
—— 4-(4-Ethoxyphenyl)-6-methoxy-3,3-dimethyl-2-phenyl-2,4-dihydrochromene —— C26H28O3
4-(4-Ethoxyphenyl)-6-methoxy-3,3-dimethyl-2-phenyl-2,4-dihydrochromene
—— 2'-amino-6-bromo-3'-methyl-2-phenylspiro[2,3-dihydrochromene-4,5'-4H-imidazole]-4'-ol —— C18H18BrN3O2
2'-amino-6-bromo-3'-methyl-2-phenylspiro[2,3-dihydrochromene-4,5'-4H-imidazole]-4'-ol
—— 3,5-Dihydroxy-7-propoxy-2-(3-propylphenyl)chromen-4-one —— C21H22O5
3,5-Dihydroxy-7-propoxy-2-(3-propylphenyl)chromen-4-one
—— 8-[3-(3-Methoxyphenyl)prop-1-enyl]-3-methyl-7-(3-methylbut-2-enoxy)-2-phenylchromen-4-one —— C31H30O4
8-[3-(3-Methoxyphenyl)prop-1-enyl]-3-methyl-7-(3-methylbut-2-enoxy)-2-phenylchromen-4-one
—— Ethoxy-[[2-(3-hydroxy-4-methylphenyl)-4-oxochromen-3-yl]oxymethyl]phosphinic acid —— C19H19O7P
Ethoxy-[[2-(3-hydroxy-4-methylphenyl)-4-oxochromen-3-yl]oxymethyl]phosphinic acid
—— 4-methyl-3-(4-nitrosophenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2H-chromen-7-ol —— C29H30N2O4
4-methyl-3-(4-nitrosophenyl)-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2H-chromen-7-ol
—— 3a-Nitro-3,4-diphenyl-2,3,4,9b-tetrahydrochromeno[3,4-c]pyrrole-1,1-dicarboxylic acid —— C25H20N2O7
3a-Nitro-3,4-diphenyl-2,3,4,9b-tetrahydrochromeno[3,4-c]pyrrole-1,1-dicarboxylic acid
—— N-[2-ethyl-3-(pyrrolidin-1-ylmethyl)phenyl]-4-oxo-2-[3-(trifluoromethyl)phenyl]chromene-8-carboxamide —— C30H27F3N2O3
N-[2-ethyl-3-(pyrrolidin-1-ylmethyl)phenyl]-4-oxo-2-[3-(trifluoromethyl)phenyl]chromene-8-carboxamide
—— [(2R,3R)-2,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)-3,4-dihydrochromen-3-yl] 3,4,5-trihydroxybenzoate —— C22H18O11
[(2R,3R)-2,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)-3,4-dihydrochromen-3-yl] 3,4,5-trihydroxybenzoate
—— 2-methyl-2-phenyl-6-[4-(trifluoromethyl)phenyl]spiro[3H-chromene-4,4'-imidazole] —— C25H19F3N2O
2-methyl-2-phenyl-6-[4-(trifluoromethyl)phenyl]spiro[3H-chromene-4,4'-imidazole]
—— 2-[3,4-bis(phenylmethoxy)phenyl]-3,5-dihydroxy-7-phenylmethoxychromen-4-one;6-methylsulfonyl-2-phenyl-1H-benzimidazole —— C50H40N2O9S
2-[3,4-bis(phenylmethoxy)phenyl]-3,5-dihydroxy-7-phenylmethoxychromen-4-one;6-methylsulfonyl-2-phenyl-1H-benzimidazole
—— Hydroxymethoxyflavone —— C16H12O4
Hydroxymethoxyflavone
—— 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3-(13-hydroxytridecyl)-7-methoxychromen-4-one —— C29H38O7
2-(3,4-Dihydroxyphenyl)-5-hydroxy-3-(13-hydroxytridecyl)-7-methoxychromen-4-one
—— 2-(4-Hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-5-yl)methoxy]chromen-4-one —— C25H17NO5
2-(4-Hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-5-yl)methoxy]chromen-4-one
—— 4-(4-acetylphenoxy)butyl prop-2-enoate;(2S,3S)-2-(3,4-dimethylphenyl)-3,5,7-trimethyl-3,4-dihydro-2H-chromene —— C35H42O5
4-(4-acetylphenoxy)butyl prop-2-enoate;(2S,3S)-2-(3,4-dimethylphenyl)-3,5,7-trimethyl-3,4-dihydro-2H-chromene
—— (5S)-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-ol —— C29H29NO4
(5S)-5-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-ol
—— N-[6-[[(2S)-2-(3-hydroxyphenyl)-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]-3-methylbutanamide —— C25H26N2O4
N-[6-[[(2S)-2-(3-hydroxyphenyl)-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]-3-methylbutanamide
—— 3-[2-(2,3-Difluorophenyl)-2'-ethenyl-1'-methyl-5'-oxospiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl]benzonitrile —— C27H19F2N3O2
3-[2-(2,3-Difluorophenyl)-2'-ethenyl-1'-methyl-5'-oxospiro[2,3-dihydrochromene-4,4'-imidazole]-6-yl]benzonitrile
—— 3',4',5,7-tetramethylpropolin G —— C34H44O6
3',4',5,7-tetramethylpropolin G
—— [2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxy-3,4-dihydro-2H-chromen-5-yl] 3,4,5-trihydroxybenzoate —— C23H20O10
[2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxy-3,4-dihydro-2H-chromen-5-yl] 3,4,5-trihydroxybenzoate
—— Hydroxytrimethoxyflavone —— C18H16O6
Hydroxytrimethoxyflavone
—— 10,11-Dimethoxy-5,5-bis(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-3-carboxylic acid —— C39H34O7
10,11-Dimethoxy-5,5-bis(4-methoxyphenyl)-21,21-dimethyl-6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-3-carboxylic acid
—— 9-(2-Phenylchromenylium-3-yl)undecan-5-ol —— C26H33O2+
9-(2-Phenylchromenylium-3-yl)undecan-5-ol
—— (2R,3R)-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,3R)-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
—— 2-(2,6-Difluorophenyl)-8-[[hydroxy(1,3-thiazol-4-yl)methyl]amino]chromen-4-one —— C19H12F2N2O3S
2-(2,6-Difluorophenyl)-8-[[hydroxy(1,3-thiazol-4-yl)methyl]amino]chromen-4-one
—— 5,7-dihydroxy-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one —— C21H20O13
5,7-dihydroxy-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
—— 7-Ethyl-6-(2-fluoropyridin-3-yl)-2-phenyl-2,3-dihydrochromen-4-one —— C22H18FNO2
7-Ethyl-6-(2-fluoropyridin-3-yl)-2-phenyl-2,3-dihydrochromen-4-one
—— N-[6-[[(2R)-2-phenyl-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]pyrrolidine-2-carboxamide —— C25H25N3O3
N-[6-[[(2R)-2-phenyl-3,4-dihydro-2H-chromen-6-yl]oxy]pyridin-3-yl]pyrrolidine-2-carboxamide
—— 5,7-Dimethoxy-2-(4-methoxyphenyl)-8-[4-(1-nitrosoethyl)phenoxy]chromen-4-one —— C26H23NO7
5,7-Dimethoxy-2-(4-methoxyphenyl)-8-[4-(1-nitrosoethyl)phenoxy]chromen-4-one
—— 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one —— C26H28O12
2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxychromen-4-one
—— 2-amino-2'-(3-fluorophenyl)-6'-methylspiro[1H-imidazole-4,4'-2,3-dihydrochromene]-5-one —— C18H16FN3O2
2-amino-2'-(3-fluorophenyl)-6'-methylspiro[1H-imidazole-4,4'-2,3-dihydrochromene]-5-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one —— C21H20O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(2R,5S)-5-methylpyrrolidin-2-yl]chromen-4-one —— C20H19NO7
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(2R,5S)-5-methylpyrrolidin-2-yl]chromen-4-one
—— 2-Methyl-8-phenyl-3,6,7,8-tetrahydropyrano[2,3-e]benzimidazole-5-carboxylic acid —— C18H16N2O3
2-Methyl-8-phenyl-3,6,7,8-tetrahydropyrano[2,3-e]benzimidazole-5-carboxylic acid
—— 2-[(2-Phenyl-3,4-dihydrochromen-2-yl)oxy]aniline —— C21H19NO2
2-[(2-Phenyl-3,4-dihydrochromen-2-yl)oxy]aniline
—— 6,8-Bis(ethoxymethyl)-5-hydroxy-7-methoxy-2-phenylchromen-4-one —— C22H24O6
6,8-Bis(ethoxymethyl)-5-hydroxy-7-methoxy-2-phenylchromen-4-one
—— Trimethoxy flavanone —— C18H18O5
Trimethoxy flavanone
—— 2,5-Dichloro-4-(9,9,11,23,25,25-hexamethyl-2-oxa-8,26-diazaheptacyclo[16.12.0.03,16.04,13.07,12.021,30.022,27]triaconta-1(18),4(13),5,7(12),14,16,19,21(30),22(27),28-decaen-17-yl)benzene-1,3-dicarboxylic acid —— C41H38Cl2N2O5
2,5-Dichloro-4-(9,9,11,23,25,25-hexamethyl-2-oxa-8,26-diazaheptacyclo[16.12.0.03,16.04,13.07,12.021,30.022,27]triaconta-1(18),4(13),5,7(12),14,16,19,21(30),22(27),28-decaen-17-yl)benzene-1,3-dicarboxylic acid
—— 2-[3-[[[Ethyl(methyl)amino]methoxy-methylphosphoryl]methoxy]-4-hydroxyphenyl]-3,5-dihydroxy-7-methylchromen-4-one —— C22H26NO8P
2-[3-[[[Ethyl(methyl)amino]methoxy-methylphosphoryl]methoxy]-4-hydroxyphenyl]-3,5-dihydroxy-7-methylchromen-4-one
—— 8-Benzyloxy-4-(4-benzyloxy-phenyl)-2-butylidene-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromene —— C36H36O3
8-Benzyloxy-4-(4-benzyloxy-phenyl)-2-butylidene-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromene
—— 3-methyl-4-oxo-2-phenyl-N-(2-pyridin-2-ylethyl)chromene-8-carboxamide —— C24H20N2O3
3-methyl-4-oxo-2-phenyl-N-(2-pyridin-2-ylethyl)chromene-8-carboxamide
—— 5,7-dihydroxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one —— C21H20O13
5,7-dihydroxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
—— (E)-3-(4-methoxy-5-oxo-7-phenylfuro[3,2-g]chromen-9-yl)prop-2-enal —— C21H14O5
(E)-3-(4-methoxy-5-oxo-7-phenylfuro[3,2-g]chromen-9-yl)prop-2-enal
—— (E)-3-[4-methoxy-7-(4-methoxyphenyl)-5-oxofuro[3,2-g]chromen-9-yl]prop-2-enal —— C22H16O6
(E)-3-[4-methoxy-7-(4-methoxyphenyl)-5-oxofuro[3,2-g]chromen-9-yl]prop-2-enal
—— brachydin B —— C33H30O7
brachydin B