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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
—— N-(2,3-dimethylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide —— C25H21NO5
N-(2,3-dimethylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide
—— N-(3-chlorophenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide 853749-62-9 C23H16ClNO5
N-(3-chlorophenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide
—— N-(2-ethylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide —— C25H21NO5
N-(2-ethylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide
—— N-(3-chloro-2-methylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide —— C24H18ClNO5
N-(3-chloro-2-methylphenyl)-2-[(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]acetamide
—— 7-{6-[4,5-Dihydroxy-6-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-chromen-4-one —— C35H44O20
7-{6-[4,5-Dihydroxy-6-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-chromen-4-one
—— 7-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-chromen-4-one —— C35H44O21
7-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-chromen-4-one
—— 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one —— C29H34O16
5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-3-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
—— 3',4',5,7-tetrahydroxy-3-methoxyflavone-7-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside 125206-11-3 C28H32O16
3',4',5,7-tetrahydroxy-3-methoxyflavone-7-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside
—— Robustaflavone & 3TC —— C38H29N3O13S
Robustaflavone & 3TC
—— Robustaflavone & PCV —— C40H33N5O13
Robustaflavone & PCV
—— Thalassiolin B 518057-59-5 C22H22O14S
Thalassiolin B
—— Thalassiolin C 518057-56-2 C21H20O13S
Thalassiolin C
—— Thalassiolin A 207683-70-3 C21H20O14S
Thalassiolin A
—— delphinidin 3-neohesperidoside —— C27H31O16
delphinidin 3-neohesperidoside
—— (2R,3R,4S,5S,6R)-3-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxychromenylium-7-yl]oxy-6-(hydroxymethyl)oxane-2,4,5-triol —— C21H21O11+
(2R,3R,4S,5S,6R)-3-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxychromenylium-7-yl]oxy-6-(hydroxymethyl)oxane-2,4,5-triol
—— (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C27H31O16+
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— Cyanidin 3,5-digalactoside —— C27H31O16+
Cyanidin 3,5-digalactoside
—— (2S,3R,4S,5R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxyoxane-3,4,5-triol —— C20H19O9+
(2S,3R,4S,5R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxyoxane-3,4,5-triol
—— 5,7-Dihydroxy-2-(4-methoxyphenyl)chromenylium-4-carboxylic acid —— C17H13O6+
5,7-Dihydroxy-2-(4-methoxyphenyl)chromenylium-4-carboxylic acid
—— [(2S,3R,4S,5R)-6-[[(2R,3S,4S,5R)-6-[2-(3,4-dihydroxy-5-methoxyphenyl)-7-hydroxy-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate —— C43H49O23+
[(2S,3R,4S,5R)-6-[[(2R,3S,4S,5R)-6-[2-(3,4-dihydroxy-5-methoxyphenyl)-7-hydroxy-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate
—— 2,4-Bis(4-methoxyphenyl)chromenylium-5,7-diol —— C23H19O5+
2,4-Bis(4-methoxyphenyl)chromenylium-5,7-diol
—— 2-[2,4-Bis(phenylmethoxy)phenyl]-3-methoxychromenylium-7-ol —— C30H25O5+
2-[2,4-Bis(phenylmethoxy)phenyl]-3-methoxychromenylium-7-ol
—— 7-[(2S,3R,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-[(2S,3R,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
—— quercetin-3-O-butyrate —— C19H16O8
quercetin-3-O-butyrate
—— Dodecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester —— C27H32O8
Dodecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester
—— Tetradecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester —— C29H36O8
Tetradecanoic acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl ester
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylpalmitate —— C31H40O8
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-ylpalmitate
—— 3-O-decanoylquercetin —— C25H28O8
3-O-decanoylquercetin
—— 7-(4-Chlorobutoxy)-2-(3,4-dibenzyloxyphenyl)-5-hydroxy-3-methoxy-chromen-4-one —— C34H31ClO7
7-(4-Chlorobutoxy)-2-(3,4-dibenzyloxyphenyl)-5-hydroxy-3-methoxy-chromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-7-[2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-3-methoxy-4-oxo-chromen-7-yl]oxyethoxy]-5-hydroxy-3-methoxy-chromen-4-one —— C34H26O14
2-(3,4-Dihydroxyphenyl)-7-[2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-3-methoxy-4-oxo-chromen-7-yl]oxyethoxy]-5-hydroxy-3-methoxy-chromen-4-one
—— 2-(3,4-Dibenzyloxyphenyl)-5-hydroxy-7-(6-hydroxyhexoxy)-3-methoxy-chromen-4-one —— C36H36O8
2-(3,4-Dibenzyloxyphenyl)-5-hydroxy-7-(6-hydroxyhexoxy)-3-methoxy-chromen-4-one
—— 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-(6-hydroxyhexoxy)-3-methoxy-chromen-4-one —— C22H24O8
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-(6-hydroxyhexoxy)-3-methoxy-chromen-4-one
—— 8-(1,1-Dimethylpropyl)-3,5,7-trihydroxy-2-[8-hydroxy-2,2-dimethyl-5-(3-methylbut-2-enyl)chroman-6-yl]chromen-4-one —— C30H36O7
8-(1,1-Dimethylpropyl)-3,5,7-trihydroxy-2-[8-hydroxy-2,2-dimethyl-5-(3-methylbut-2-enyl)chroman-6-yl]chromen-4-one
—— wikstrol A —— C30H22O10
wikstrol A
—— [(2S,3R,4S,5S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chromen-3-yl]peroxy-4,5-dihydroxy-tetrahydropyran-3-yl] 3,4,5-trihydroxybenzoate —— C27H22O16
[(2S,3R,4S,5S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chromen-3-yl]peroxy-4,5-dihydroxy-tetrahydropyran-3-yl] 3,4,5-trihydroxybenzoate
—— 5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one —— C21H20O10
5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
—— 5-hydroxy-2-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one —— C31H34O11
5-hydroxy-2-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-8,8-dimethyl-3-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
—— 5,7-Dihydroxy-2-[4-hydroxy-3-methoxy-5-(3-methylbut-2-enyl)phenyl]chromen-4-one —— C21H20O6
5,7-Dihydroxy-2-[4-hydroxy-3-methoxy-5-(3-methylbut-2-enyl)phenyl]chromen-4-one
—— 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione; 3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C25H23N5O10
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione; 3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)chromen-4-one; (3,4,5-trihydroxy-6-phenethyloxy-tetrahydropyran-2-yl)methyl 3,4,5-trihydroxybenzoate —— C36H34O16
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)chromen-4-one; (3,4,5-trihydroxy-6-phenethyloxy-tetrahydropyran-2-yl)methyl 3,4,5-trihydroxybenzoate
—— 2-(2,2-Dimethylchroman-6-yl)-5,7-dihydroxy-chromen-4-one —— C20H18O5
2-(2,2-Dimethylchroman-6-yl)-5,7-dihydroxy-chromen-4-one
—— 6-acetyl-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-8-yl]-1,4,8-trihydroxyxanthen-9-one —— C36H28O17
6-acetyl-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-8-yl]-1,4,8-trihydroxyxanthen-9-one
—— (2R,3R)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one —— C21H22O10
(2R,3R)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
—— (2S)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-(2,5-dihydroxyphenyl)-5-hydroxy-chroman-4-one —— C21H22O10
(2S)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-(2,5-dihydroxyphenyl)-5-hydroxy-chroman-4-one
—— (2R,3R)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-chroman-4-one —— C21H22O11
(2R,3R)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-chroman-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one —— C21H20O12
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3S,4R,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]chromen-4-one
—— quercetin-3-O-(2''-O-galloyl)-β-D-glucopyranoside 69624-79-9 C28H24O16
quercetin-3-O-(2''-O-galloyl)-β-D-glucopyranoside
—— [5-[5,7-Dihydroxy-4-oxo-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-2-yl]-2-hydroxyphenyl] hydrogen sulfate —— C27H30O19S
[5-[5,7-Dihydroxy-4-oxo-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-2-yl]-2-hydroxyphenyl] hydrogen sulfate
—— dorsmanin C —— C30H32O7
dorsmanin C
—— 5,7-dihydroxy-2-[3-[(E)-3-hydroxy-3-methylbut-1-enyl]-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one —— C26H30O6
5,7-dihydroxy-2-[3-[(E)-3-hydroxy-3-methylbut-1-enyl]-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one