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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
—— Sanggenone H —— C20H18O6
Sanggenone H
—— methyl (2S)-1-[2-[4-(5,7-dimethoxy-4-oxochromen-2-yl)phenoxy]ethyl]pyrrolidine-2-carboxylate —— C25H27NO7
methyl (2S)-1-[2-[4-(5,7-dimethoxy-4-oxochromen-2-yl)phenoxy]ethyl]pyrrolidine-2-carboxylate
—— 5,7-Dimethoxy-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]chromen-4-one;hydrochloride —— C23H26ClNO5
5,7-Dimethoxy-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]chromen-4-one;hydrochloride
—— 2-[4-(2-Hydroxy-3-piperidin-1-ylpropoxy)phenyl]-5,7-dimethoxychromen-4-one;hydrochloride —— C25H30ClNO6
2-[4-(2-Hydroxy-3-piperidin-1-ylpropoxy)phenyl]-5,7-dimethoxychromen-4-one;hydrochloride
—— 3-[[1-[2-(4-Chlorophenyl)-6-(4-fluorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one —— C36H28ClFIN3O5
3-[[1-[2-(4-Chlorophenyl)-6-(4-fluorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one
—— 3-[[1-[2-(4-Chlorophenyl)-6-phenyloxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one —— C36H29ClIN3O5
3-[[1-[2-(4-Chlorophenyl)-6-phenyloxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one
—— 3-[[1-[2,6-Bis(4-bromophenyl)oxan-4-yl]triazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one —— C36H29Br2N3O5
3-[[1-[2,6-Bis(4-bromophenyl)oxan-4-yl]triazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one
—— 3-[[1-[2-(4-Bromophenyl)-6-(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one —— C36H28BrClIN3O4
3-[[1-[2-(4-Bromophenyl)-6-(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one
—— 3-[[5-Iodo-1-[2-phenyl-6-(3,4,5-trimethoxyphenyl)oxan-4-yl]triazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one —— C39H36IN3O7
3-[[5-Iodo-1-[2-phenyl-6-(3,4,5-trimethoxyphenyl)oxan-4-yl]triazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one
—— 3-[[1-[2,6-Bis(4-bromophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one —— C35H25Br2ClIN3O4
3-[[1-[2,6-Bis(4-bromophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one
—— 2-(4-Chlorophenyl)-3-[[1-(2,6-diphenyloxan-4-yl)-5-iodotriazol-4-yl]methoxy]chromen-4-one —— C35H27ClIN3O4
2-(4-Chlorophenyl)-3-[[1-(2,6-diphenyloxan-4-yl)-5-iodotriazol-4-yl]methoxy]chromen-4-one
—— 3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one —— C36H28Cl2IN3O4
3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methylphenyl)chromen-4-one
—— 2-(4-Methoxyphenyl)-3-[[1-[2-(4-methoxyphenyl)-6-phenyloxan-4-yl]triazol-4-yl]methoxy]chromen-4-one —— C37H33N3O6
2-(4-Methoxyphenyl)-3-[[1-[2-(4-methoxyphenyl)-6-phenyloxan-4-yl]triazol-4-yl]methoxy]chromen-4-one
—— 3-[[1-[2-(4-Bromophenyl)-6-(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one —— C35H25BrCl2IN3O4
3-[[1-[2-(4-Bromophenyl)-6-(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one
—— 2-(4-Chlorophenyl)-3-[[1-[2-(4-methoxyphenyl)-6-phenyloxan-4-yl]triazol-4-yl]methoxy]chromen-4-one —— C36H30ClN3O5
2-(4-Chlorophenyl)-3-[[1-[2-(4-methoxyphenyl)-6-phenyloxan-4-yl]triazol-4-yl]methoxy]chromen-4-one
—— 3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one —— C35H25Cl3IN3O4
3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-chlorophenyl)chromen-4-one
—— 3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one —— C36H28Cl2IN3O5
3-[[1-[2,6-Bis(4-chlorophenyl)oxan-4-yl]-5-iodotriazol-4-yl]methoxy]-2-(4-methoxyphenyl)chromen-4-one
—— 5-Amino-1-cyclopropyl-6,8-difluoro-7-[4-[2-(5-hydroxy-4-oxo-2-phenyl-chromen-7-yl)oxyethyl]-3,5-dimethyl-piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid —— C36H34F2N4O7
5-Amino-1-cyclopropyl-6,8-difluoro-7-[4-[2-(5-hydroxy-4-oxo-2-phenyl-chromen-7-yl)oxyethyl]-3,5-dimethyl-piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
—— 1-cyclopropyl-7-[4-[2-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]ethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid —— C34H33N3O8
1-cyclopropyl-7-[4-[2-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]ethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
—— 1-ethyl-7-[4-[2-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]ethyl]piperazin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid —— C32H32N4O8
1-ethyl-7-[4-[2-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]ethyl]piperazin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
—— 5-Amino-6-fluoro-1-(4-fluorophenyl)-7-[4-[2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid —— C37H30F2N4O7
5-Amino-6-fluoro-1-(4-fluorophenyl)-7-[4-[2-(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxyethyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
—— [6-bromo-2-(4-chlorophenyl)-4-oxo-2,3-dihydrochromen-3-yl] N,N-diethylcarbamodithioate —— C20H19BrClNO2S2
[6-bromo-2-(4-chlorophenyl)-4-oxo-2,3-dihydrochromen-3-yl] N,N-diethylcarbamodithioate
—— 8-(4-(2-fluorophenyl)piperazine-1-carbonyl)-3-methyl-2-phenyl-4H-chromen-4-one —— C27H23FN2O3
8-(4-(2-fluorophenyl)piperazine-1-carbonyl)-3-methyl-2-phenyl-4H-chromen-4-one
—— N-(5-ethyl-1,3,4-thiadiazol-2-yl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide —— C21H17N3O3S
N-(5-ethyl-1,3,4-thiadiazol-2-yl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
—— 3-methyl-4-oxo-2-phenyl-N-(pyridin-2-ylmethyl)-4H-chromene-8-carboxamide —— C23H18N2O3
3-methyl-4-oxo-2-phenyl-N-(pyridin-2-ylmethyl)-4H-chromene-8-carboxamide
—— [2-[3,4-di(hexadecanoyloxy)-5-hydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate —— C54H78O13
[2-[3,4-di(hexadecanoyloxy)-5-hydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
—— pelargonidin 3-O-(3",6"-O-dimalonyl-beta-glucopyranoside —— C27H22O16-2
pelargonidin 3-O-(3",6"-O-dimalonyl-beta-glucopyranoside
—— 3-[[(2R,3R,4S,5R,6S)-4-(2-carboxyacetyl)oxy-3,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid —— C27H24O16
3-[[(2R,3R,4S,5R,6S)-4-(2-carboxyacetyl)oxy-3,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid
—— 3-O-(6-O-(trans-p-coumaryl)-2-O-(2-O-(trans-sinapyl)-β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(6-O-(malonyl)-β-D-glucopyranoside) —— C55H57O29
3-O-(6-O-(trans-p-coumaryl)-2-O-(2-O-(trans-sinapyl)-β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(6-O-(malonyl)-β-D-glucopyranoside)
—— isorhamnetin 3-O-(4"-O-p-coumaroyl)-glucoside —— C31H28O14
isorhamnetin 3-O-(4"-O-p-coumaroyl)-glucoside
—— isorhamnetin 3-O-(3"-O-p-coumaroyl, 6"-O-feruloyl)-glucoside —— C41H36O17
isorhamnetin 3-O-(3"-O-p-coumaroyl, 6"-O-feruloyl)-glucoside
—— 3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoate —— C24H21O14-
3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoate
—— [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methoxycarbonyl]phenoxy]oxan-2-yl]methyl 4-hydroxybenzoate —— C53H58O30
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methoxycarbonyl]phenoxy]oxan-2-yl]methyl 4-hydroxybenzoate
—— Platyconin —— C63H72O37
Platyconin
—— 3-oxo-3-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[5-hydroxy-2-[4-hydroxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid —— C45H48O27
3-oxo-3-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[5-hydroxy-2-[4-hydroxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid
—— 3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C27H30O16
3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C22H21O13-
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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 (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate —— C42H46O23
[(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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 (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
—— 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-6-methoxy-4-oxochromen-5-olate —— C16H11O8-
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-6-methoxy-4-oxochromen-5-olate
—— (2R)-4-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-hydroxy-4-oxobutanoic acid —— C25H24O15
(2R)-4-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-hydroxy-4-oxobutanoic acid
—— kaempferol 3-O-beta-D-glucosyl-(1->2)-glucoside —— C27H29O16-
kaempferol 3-O-beta-D-glucosyl-(1->2)-glucoside
—— cyanidin O-O-[6-O-(6-O-feruloyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside] —— C42H45O23-
cyanidin O-O-[6-O-(6-O-feruloyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside]
—— 3-oxo-3-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[5-hydroxy-2-[4-hydroxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoate —— C45H47O27-
3-oxo-3-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[5-hydroxy-2-[4-hydroxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoate
—— 2,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3H-chromen-5-olate —— C15H11O6-
2,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3H-chromen-5-olate
—— cyanidin 3-O-glucoside-7-O-(6-O-(p-hydroxybenzoyl)-glucoside) —— C34H34O18
cyanidin 3-O-glucoside-7-O-(6-O-(p-hydroxybenzoyl)-glucoside)
—— [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-7-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-5-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate —— C36H36O18
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-7-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-5-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
—— Petunidin(1-) —— C16H11O7-
Petunidin(1-)
—— quercetin 3-O-(3"-O-p-coumaroyl, 6"-O-feruloyl)-glucoside —— C40H34O17
quercetin 3-O-(3"-O-p-coumaroyl, 6"-O-feruloyl)-glucoside
—— Gossypetin 3',8-dimethyl ether —— C17H13O8-
Gossypetin 3',8-dimethyl ether
—— 3',4',5'-Pentahydroxyflavanone —— C15H11O7-
3',4',5'-Pentahydroxyflavanone