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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
—— methyl 2-[2-(4-chlorophenyl)-6-methyl-4-oxochromen-8-yl]butanoate 213622-47-0 C21H19ClO4
methyl 2-[2-(4-chlorophenyl)-6-methyl-4-oxochromen-8-yl]butanoate
—— tert-butyl (R)-3-hydroxy-3-[(S)-6-methyl-2-phenyl-2H-chromen-3-yl]propanoate 1101850-49-0 C23H26O4
tert-butyl (R)-3-hydroxy-3-[(S)-6-methyl-2-phenyl-2H-chromen-3-yl]propanoate
—— (2R,3S)-2,3-trans-3-acetoxy-6-<(2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-8-<(2S,3R,4R)-2,3-trans-3,4-trans-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-3',4',5,7-tetramethoxyflavan 88269-43-6 C61H64O19
(2R,3S)-2,3-trans-3-acetoxy-6-<(2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-8-<(2S,3R,4R)-2,3-trans-3,4-trans-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-3',4',5,7-tetramethoxyflavan
—— (2R,3S)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylcatechin 1390643-79-4 C42H46O6Si
(2R,3S)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylcatechin
—— 1-(4-fluorophenyl)-3-(4-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one 1089663-32-0 C21H21FO7
1-(4-fluorophenyl)-3-(4-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one
—— 1268520-49-5 C23H16Cl2O4
—— 5,7-bis(phenylmethoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-one 701284-21-1 C32H30O7
5,7-bis(phenylmethoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-one
—— 5-hydroxy-4'-N,N-diacetylaminoflavone 1257513-94-2 C19H15NO5
5-hydroxy-4'-N,N-diacetylaminoflavone
—— diethyl 2-[(4-oxo-2-phenyl-4H-chromen-7-ylamino)-methylene]malonate 1492929-07-3 C23H21NO6
diethyl 2-[(4-oxo-2-phenyl-4H-chromen-7-ylamino)-methylene]malonate
—— 534569-46-5 C17H17N3O2
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trimethoxybenzoate 217661-75-1 C42H49O24
[(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trimethoxybenzoate
—— 4-Ureido-flavan 94459-62-8 C16H16N2O2
4-Ureido-flavan
—— (<i>S</i>)-5,7-dihydroxy-2-phenyl-chroman-4-one-(2,4-dinitro-phenylhydrazone) 113060-61-0 C21H16N4O7
(<i>S</i>)-5,7-dihydroxy-2-phenyl-chroman-4-one-(2,4-dinitro-phenylhydrazone)
—— Acetic acid 8-[5-(5-acetoxy-7-methoxy-4-oxo-chroman-2-yl)-2-methoxy-phenyl]-2-(3-acetoxy-4-methoxy-phenyl)-7-methoxy-4-oxo-chroman-5-yl ester 90332-25-5 C40H36O14
Acetic acid 8-[5-(5-acetoxy-7-methoxy-4-oxo-chroman-2-yl)-2-methoxy-phenyl]-2-(3-acetoxy-4-methoxy-phenyl)-7-methoxy-4-oxo-chroman-5-yl ester
—— (2R)-caesalflavan B 1255922-09-8 C17H18O4
(2R)-caesalflavan B
—— 78536-13-7 C57H64O32
—— 3-(4-hydroxyphenyl)-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-4-(trinuoromethyl)-2H-chromen-6-ol 1352307-87-9 C30H30F3NO4
3-(4-hydroxyphenyl)-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-4-(trinuoromethyl)-2H-chromen-6-ol
—— 3-hydroxy-2-phenyl-pyrano[3,2-c]quinolin-4-one 98348-51-7 C18H11NO3
3-hydroxy-2-phenyl-pyrano[3,2-c]quinolin-4-one
—— 2',4',6'-Trimethoxy-6-nitroflavon 59496-01-4 C18H15NO7
2',4',6'-Trimethoxy-6-nitroflavon
—— 2-(2-amino-3-methoxyphenyl)-8-(3-tert-butoxycarbonylaminopropyl)-6-chlorochromone 1621457-87-1 C24H27ClN2O5
2-(2-amino-3-methoxyphenyl)-8-(3-tert-butoxycarbonylaminopropyl)-6-chlorochromone
—— 6-hydroxy-2-[3-(pyridin-2-yloxy)phenyl]chroman-4-one 728934-97-2 C20H15NO4
6-hydroxy-2-[3-(pyridin-2-yloxy)phenyl]chroman-4-one
—— 6-hydroxy-2-(3-benzyloxyphenyl)chroman-4-one 728934-93-8 C22H18O4
6-hydroxy-2-(3-benzyloxyphenyl)chroman-4-one
—— 2-phenyl-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol 896121-51-0 C29H26O4
2-phenyl-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
—— 1400900-16-4 C31H26ClNO3S
—— 7-hydroxy-8-(1',2'-dimethylallyl)flavone 77609-95-1 C20H18O3
7-hydroxy-8-(1',2'-dimethylallyl)flavone
—— 5-(4-chlorophenyl)-2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline 239066-99-0 C26H24ClNO2
5-(4-chlorophenyl)-2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline
—— 6-acetoxy-2-(2,3-diacetoxy-phenyl)-chromen-4-one 110144-71-3 C21H16O8
6-acetoxy-2-(2,3-diacetoxy-phenyl)-chromen-4-one
—— N-[3-(pyrrolidin-1-yl)propyl]flavone-8-carboxamide 92606-61-6 C23H24N2O3
N-[3-(pyrrolidin-1-yl)propyl]flavone-8-carboxamide
—— (+)-3,5,7,4'-tetra-O-acetylcatechin 1209469-09-9 C23H22O10
(+)-3,5,7,4'-tetra-O-acetylcatechin
—— 6-chloro-3-methoxy-8-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one 132020-79-2 C24H19ClO4
6-chloro-3-methoxy-8-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one
—— 3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-piperidino)ethoxy]-phenyl]dibenzo[b,d]pyran 713520-58-2 C38H55NO4Si2
3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-piperidino)ethoxy]-phenyl]dibenzo[b,d]pyran
—— hexahydrotanariflavanone B 1178898-28-6 C30H40O6
hexahydrotanariflavanone B
—— (2R,3S)-2,3-trans-3-acetoxy-6,8-bis-<(2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-3',4',5,7-tetramethoxyflavan 88269-44-7 C61H64O19
(2R,3S)-2,3-trans-3-acetoxy-6,8-bis-<(2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-3',4',7-trimethoxyflavan-4-yl>-3',4',5,7-tetramethoxyflavan
—— 2',4'-dimethoxy-3-methylflavone-8-carboxylic acid N,N-diethylamide 90102-07-1 C23H25NO5
2',4'-dimethoxy-3-methylflavone-8-carboxylic acid N,N-diethylamide
—— 2-(3-benzyloxyphenyl)chroman-4,6-diol 728935-01-1 C22H20O4
2-(3-benzyloxyphenyl)chroman-4,6-diol
—— 534569-40-9 C16H15N3O3
—— (2R,3R)-5,7,3'-tri-O-benzyl-3-acetylepicatechin 1390643-90-9 C38H34O7
(2R,3R)-5,7,3'-tri-O-benzyl-3-acetylepicatechin
—— 3'-O-Allyl-7-O-(N,N-Dimethylaminocarbonylmethyl)diosmetin 205524-25-0 C23H23NO7
3'-O-Allyl-7-O-(N,N-Dimethylaminocarbonylmethyl)diosmetin
—— 3,8-dibromo-7-butoxy-2-(3,4-dimethoxyphenyl)-6-nitrochromen-4-one 139589-42-7 C21H19Br2NO7
3,8-dibromo-7-butoxy-2-(3,4-dimethoxyphenyl)-6-nitrochromen-4-one
—— 4',7-di-O-benzylquercetin-3-yl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-acetyl-3-O-benzoyl-β-D-glucopyranoside 862583-25-3 C73H62O22
4',7-di-O-benzylquercetin-3-yl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-acetyl-3-O-benzoyl-β-D-glucopyranoside
—— 5,8-diacetoxy-2-(3,4-dimethoxy-phenyl)-7-methoxy-chromen-4-one 89456-47-3 C22H20O9
5,8-diacetoxy-2-(3,4-dimethoxy-phenyl)-7-methoxy-chromen-4-one
—— 6-Rutinosido-aureusidin 103444-29-7 C27H30O15
6-Rutinosido-aureusidin
—— N-[4-(6-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide 153255-70-0 C18H14N2O5
N-[4-(6-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide
—— 7-((3-bromobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate 1254040-77-1 C26H19BrO7
7-((3-bromobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate
—— 8-Butyryl-6-methyl-2-phenyl-chromen-4-one 213622-37-8 C20H18O3
8-Butyryl-6-methyl-2-phenyl-chromen-4-one
—— 3,7,4'-triacetoxy catechin 1071725-95-5 C21H20O9
3,7,4'-triacetoxy catechin
—— 3-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one 103392-99-0 C17H14O6
3-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one
—— (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one 126655-06-9 C22H16O9
(2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one
—— 9-bromo-4-methoxy-7-phenyl-5H-furo[3,2-g]chromen-5-one 1616883-45-4 C18H11BrO4
9-bromo-4-methoxy-7-phenyl-5H-furo[3,2-g]chromen-5-one
—— 2-phenyl-3-phenylsulphonyl-6-methylchromone 87127-66-0 C22H16O4S
2-phenyl-3-phenylsulphonyl-6-methylchromone