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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
—— 5-hydroxy-3,6-dimethoxy-2-[3-methoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one —— C24H26O12
5-hydroxy-3,6-dimethoxy-2-[3-methoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
—— [(2S,3R,4S,5R,6R)-6-(acetyloxymethyl)-2-[2,3-dihydroxy-5-(3,5,7-trihydroxychromenylium-2-yl)phenoxy]-4,5-dihydroxyoxan-3-yl] 3,4,5-trihydroxybenzoate —— C30H27O17+
[(2S,3R,4S,5R,6R)-6-(acetyloxymethyl)-2-[2,3-dihydroxy-5-(3,5,7-trihydroxychromenylium-2-yl)phenoxy]-4,5-dihydroxyoxan-3-yl] 3,4,5-trihydroxybenzoate
—— (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(1R,2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol —— C34H43O19+
(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(1R,2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
—— acetylpectolinarin —— C31H36O16
acetylpectolinarin
—— (2S,3R,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid —— C22H20O12
(2S,3R,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
—— [(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate —— C39H32O14
[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one —— C26H28O15
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— [(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate;chloride —— C42H47ClO24
[(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate;chloride
—— [(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl]oxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate —— C29H32O15
[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-5-yl]oxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate
—— Baeckea frutescens 5 —— C30H32O6
Baeckea frutescens 5
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one —— C27H30O15
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-4-methylbenzenesulfonamide —— C22H16ClNO5S
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-4-methylbenzenesulfonamide
—— 2-chloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide 958745-66-9 C22H13Cl2NO4
2-chloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide
—— 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one —— C21H20O11
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— Baeckea frutescens 4 —— C30H32O6
Baeckea frutescens 4
—— Vicinin 2 90456-53-4 C27H30O17
Vicinin 2
—— 6,8-Diamino-2-(2-chlorophenyl)-5-hydroxychromen-4-one —— C15H11ClN2O3
6,8-Diamino-2-(2-chlorophenyl)-5-hydroxychromen-4-one
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-2-methylbenzamide —— C23H16ClNO4
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-2-methylbenzamide
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]methanesulfonamide —— C16H12ClNO5S
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]methanesulfonamide
—— 4-bromo-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide —— C22H13BrClNO4
4-bromo-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide
—— anisole;N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]acetamide —— C24H20ClNO5
anisole;N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]acetamide
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]acetamide —— C17H12ClNO4
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]acetamide
—— 3-chloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide —— C22H13Cl2NO4
3-chloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]benzamide
—— 2-(2-Chlorophenyl)-5-hydroxychromen-4-one;nitromethane —— C16H12ClNO5
2-(2-Chlorophenyl)-5-hydroxychromen-4-one;nitromethane
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]benzamide —— C22H14ClNO4
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]benzamide
—— 8-Bromo-2-(2-chlorophenyl)-5-methoxychromen-4-one —— C16H10BrClO3
8-Bromo-2-(2-chlorophenyl)-5-methoxychromen-4-one
—— 5-Methoxy-2,8-diphenylchromen-4-one —— C22H16O3
5-Methoxy-2,8-diphenylchromen-4-one
—— 2-(2-Chlorophenyl)-5-hydroxy-8-morpholin-4-ylchromen-4-one —— C19H16ClNO4
2-(2-Chlorophenyl)-5-hydroxy-8-morpholin-4-ylchromen-4-one
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-3-methylbenzamide —— C23H16ClNO4
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-3-methylbenzamide
—— 8-Bromo-2-(2-chlorophenyl)-5-hydroxychromen-4-one —— C15H8BrClO3
8-Bromo-2-(2-chlorophenyl)-5-hydroxychromen-4-one
—— 2-(1,3-benzodioxol-5-yl)-3-hydroxy-7-methyl-4H-chromen-4-one —— C17H12O5
2-(1,3-benzodioxol-5-yl)-3-hydroxy-7-methyl-4H-chromen-4-one
—— 7-chloro-2-(4-ethoxy-3-methoxyphenyl)-3-hydroxy-4H-chromen-4-one —— C18H15ClO5
7-chloro-2-(4-ethoxy-3-methoxyphenyl)-3-hydroxy-4H-chromen-4-one
—— 2-(3,5-dimethylpyrazol-1-yl)-N-[(Z)-[(2S)-2-phenyl-2,3-dihydrochromen-4-ylidene]amino]acetamide —— C22H22N4O2
2-(3,5-dimethylpyrazol-1-yl)-N-[(Z)-[(2S)-2-phenyl-2,3-dihydrochromen-4-ylidene]amino]acetamide
—— 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one —— C26H28O16
3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
—— (1R,5R,6R,13S,21S)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol —— C30H24O12
(1R,5R,6R,13S,21S)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
—— Malonylapiin —— C29H30O17
Malonylapiin
—— (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one —— C34H44O18
(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one
—— 6-(4,5-dihydro-1H-imidazol-2-yl)-2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]chromen-4-one —— C21H18N4O2
6-(4,5-dihydro-1H-imidazol-2-yl)-2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]chromen-4-one
—— 2-[4-[6-(6-carbamimidoyl-1H-benzimidazol-2-yl)-4-oxo-chromen-2-yl]phenyl]-3H-benzimidazole-5-carboxamidine —— C31H22N8O2
2-[4-[6-(6-carbamimidoyl-1H-benzimidazol-2-yl)-4-oxo-chromen-2-yl]phenyl]-3H-benzimidazole-5-carboxamidine
—— N-isopropyl-2-[4-[6-[6-(N-isopropylcarbamimidoyl)-1H-benzimidazol-2-yl]-4-oxo-chromen-2-yl]phenyl]-3H-benzimidazole-5-carboxamidine —— C37H34N8O2
N-isopropyl-2-[4-[6-[6-(N-isopropylcarbamimidoyl)-1H-benzimidazol-2-yl]-4-oxo-chromen-2-yl]phenyl]-3H-benzimidazole-5-carboxamidine
—— N-isopropyl-2-[4-(7-methoxy-4-oxo-chromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine —— C27H24N4O3
N-isopropyl-2-[4-(7-methoxy-4-oxo-chromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine
—— N-butyl-2-(4-oxo-2-phenyl-chromen-6-yl)-3H-benzimidazole-5-carboxamidine —— C27H24N4O2
N-butyl-2-(4-oxo-2-phenyl-chromen-6-yl)-3H-benzimidazole-5-carboxamidine
—— 3-Methoxy-2-phenyl-thieno[2,3-h]chromen-4-one —— C18H12O3S
3-Methoxy-2-phenyl-thieno[2,3-h]chromen-4-one
—— 2-[4-(4-oxochromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine —— C23H16N4O2
2-[4-(4-oxochromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine
—— N-isopropyl-2-[4-(N-isopropylcarbamimidoyl)phenyl]-4-oxo-chromene-6-carboxamidine —— C23H26N4O2
N-isopropyl-2-[4-(N-isopropylcarbamimidoyl)phenyl]-4-oxo-chromene-6-carboxamidine
—— 2-(4-oxo-2-phenyl-chromen-6-yl)-3H-benzimidazole-5-carboxamidine —— C23H16N4O2
2-(4-oxo-2-phenyl-chromen-6-yl)-3H-benzimidazole-5-carboxamidine
—— N-isopropyl-2-[4-(4-oxochromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine —— C26H22N4O2
N-isopropyl-2-[4-(4-oxochromen-2-yl)phenyl]-3H-benzimidazole-5-carboxamidine
—— 2-[4-(4,5-Dihydrooxazol-2-yl)phenyl]-3-methoxy-chromen-4-one —— C19H15NO4
2-[4-(4,5-Dihydrooxazol-2-yl)phenyl]-3-methoxy-chromen-4-one
—— 4-(6-Chloro-4-oxo-chroman-2-yl)benzoic acid —— C16H11ClO4
4-(6-Chloro-4-oxo-chroman-2-yl)benzoic acid
—— 4-(4-Oxochroman-2-yl)benzoic acid —— C16H12O4
4-(4-Oxochroman-2-yl)benzoic acid