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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,3R)-5,7-dihydroxy-3-[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-8-yl]-2-(4-hydroxyphenyl)chroman-4-one —— C36H32O15
(2S,3R)-5,7-dihydroxy-3-[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-8-yl]-2-(4-hydroxyphenyl)chroman-4-one
—— 6-Jod-flavonol 1222-13-5 C15H9IO3
6-Jod-flavonol
—— (2S,3R)-3-[(2S)-5,7-dimethoxy-2-(4-methoxyphenyl)-4-oxo-chroman-8-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chroman-4-one —— C36H34O10
(2S,3R)-3-[(2S)-5,7-dimethoxy-2-(4-methoxyphenyl)-4-oxo-chroman-8-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chroman-4-one
—— 8-Iod-4'-methoxy-flavonol 1230-12-2 C16H11IO4
8-Iod-4'-methoxy-flavonol
—— 3-Bromo-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one —— C20H19BrO7
3-Bromo-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
—— 8-[(2S,3R)-5,7-dimethoxy-2-(4-methoxyphenyl)-4-oxo-chroman-3-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one —— C36H32O10
8-[(2S,3R)-5,7-dimethoxy-2-(4-methoxyphenyl)-4-oxo-chroman-3-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
—— 3-[5,7-Dimethoxy-2-(4-methoxyphenyl)-4-oxo-chromen-3-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one —— C36H30O10
3-[5,7-Dimethoxy-2-(4-methoxyphenyl)-4-oxo-chromen-3-yl]-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
—— 3-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one —— C36H32O16
3-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
—— 2-(3-iodophenyl)-4H-chromen-4-one 1026-41-1 C15H9IO2
2-(3-iodophenyl)-4H-chromen-4-one
—— 8-Fluor-flavonol 2647-25-8 C15H9FO3
8-Fluor-flavonol
—— 7-Hydroxy-3',4'-methylenedioxyflavan —— C16H14O4
7-Hydroxy-3',4'-methylenedioxyflavan
—— (2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chroman-4-one —— C22H24O11
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chroman-4-one
—— 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-chroman-4-one —— C19H20O7
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-chroman-4-one
—— 8-[(Dimethylamino)methyl]-7-methoxy-3-methyl-2-phenyl-2,3-dihydrochromen-4-one —— C20H23NO3
8-[(Dimethylamino)methyl]-7-methoxy-3-methyl-2-phenyl-2,3-dihydrochromen-4-one
—— 3,5,7-Trihydroxy-2-(3,4,5-trimethoxyphenyl)chroman-4-one —— C18H18O8
3,5,7-Trihydroxy-2-(3,4,5-trimethoxyphenyl)chroman-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3S,4S,5S)-4,5,6-trihydroxyoxan-3-yl]oxy-2,3-dihydrochromen-4-one —— C20H20O11
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3S,4S,5S)-4,5,6-trihydroxyoxan-3-yl]oxy-2,3-dihydrochromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3R,4R,5S)-3,4,5,6-tetrahydroxytetrahydropyran-2-yl]methoxy]chroman-4-one —— C21H22O12
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(3R,4R,5S)-3,4,5,6-tetrahydroxytetrahydropyran-2-yl]methoxy]chroman-4-one
—— 2-(4-Oxo-2-phenyl-chroman-8-yl)acetic acid —— C17H14O4
2-(4-Oxo-2-phenyl-chroman-8-yl)acetic acid
—— cadmium(2+);5-hydroxy-2-(3-hydroxy-4-oxidophenyl)-7-oxo-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-olate —— C27H28CdO16
cadmium(2+);5-hydroxy-2-(3-hydroxy-4-oxidophenyl)-7-oxo-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-olate
—— [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate —— C30H28O12
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
—— (2S,3R,5S,6R)-2-[7-hydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromenylium-5-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol —— C29H35O17+
(2S,3R,5S,6R)-2-[7-hydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromenylium-5-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
—— [2-(3,4-Disulfooxyphenyl)-3,5-disulfooxy-chroman-7-yl] hydrogen sulfate —— C15H9K5O21S5
[2-(3,4-Disulfooxyphenyl)-3,5-disulfooxy-chroman-7-yl] hydrogen sulfate
—— [2-(3,4-disulfooxyphenyl)-3,5-disulfooxy-3,4-dihydro-2H-chromen-7-yl] hydrogen sulfate —— C15H14O21S5
[2-(3,4-disulfooxyphenyl)-3,5-disulfooxy-3,4-dihydro-2H-chromen-7-yl] hydrogen sulfate
—— (4R,6S)-6-(4-chlorophenyl)-4,5-diphenyl-3,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-1,7,9(16),12,14-pentaen-11-one —— C32H21ClO3
(4R,6S)-6-(4-chlorophenyl)-4,5-diphenyl-3,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-1,7,9(16),12,14-pentaen-11-one
—— (3R,9R,10R)-10-(2,4-Dihydroxy-phenyl)-8-(3,4-dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol —— C31H28O11
(3R,9R,10R)-10-(2,4-Dihydroxy-phenyl)-8-(3,4-dihydroxy-phenyl)-2-(3-hydroxy-4-methoxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol
—— (2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5-dihydroxy-7-methoxy-8-(3-methylbut-2-enyl)chroman-4-one —— C33H42O7
(2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5-dihydroxy-7-methoxy-8-(3-methylbut-2-enyl)chroman-4-one
—— (2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5,7-trimethoxy-8-(3-methylbut-2-enyl)chroman-4-one —— C35H46O7
(2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5,7-trimethoxy-8-(3-methylbut-2-enyl)chroman-4-one
—— 2-[3,4-dihydroxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,4,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-5-one —— C30H34O7
2-[3,4-dihydroxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,4,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-5-one
—— (2R,3R)-3,5-dihydroxy-2-[3-hydroxy-4-methoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-7-methoxy-8-(3-methylbut-2-enyl)chroman-4-one —— C32H40O7
(2R,3R)-3,5-dihydroxy-2-[3-hydroxy-4-methoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-7-methoxy-8-(3-methylbut-2-enyl)chroman-4-one
—— (2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3-hydroxy-5,7-dimethoxy-8-(3-methylbut-2-enyl)chroman-4-one —— C34H44O7
(2R,3R)-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3-hydroxy-5,7-dimethoxy-8-(3-methylbut-2-enyl)chroman-4-one
—— 3-Benzyloxy-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-5,7-dimethoxy-8-(3-methylbut-2-enyl)chroman-4-one —— C41H50O7
3-Benzyloxy-2-[3,4-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-5,7-dimethoxy-8-(3-methylbut-2-enyl)chroman-4-one
—— (2R)-7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one —— C27H32O14
(2R)-7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
—— 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2,3-dihydrochromen-4-one —— C21H22ClNO5
2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2,3-dihydrochromen-4-one
—— (2S)-2-phenyl-3,4-dihydro-2H-chromene-4,7-diol —— C15H14O3
(2S)-2-phenyl-3,4-dihydro-2H-chromene-4,7-diol
—— Bisdemalonylsalvianin 168753-26-2 C36H37O18+
Bisdemalonylsalvianin
—— Pelargonidin 3-O-rutinoside 56054-42-3 C27H31O14+
Pelargonidin 3-O-rutinoside
—— 3-[[(2R,3R,4S,5R,6S)-4-(2-carboxyacetyl)oxy-6-[3-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromenylium-5-yl]oxy-3,5-dihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid —— C42H41O24+
3-[[(2R,3R,4S,5R,6S)-4-(2-carboxyacetyl)oxy-6-[3-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromenylium-5-yl]oxy-3,5-dihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
—— 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid —— C24H22O13
3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid
—— pelargonidin 3-O-rutinoside betaine —— C27H30O14
pelargonidin 3-O-rutinoside betaine
—— 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-oxopropanoic acid —— C24H22O14
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-oxopropanoic acid
—— 4'''-Demalonylsalvianin 168753-27-3 C39H39O21+
4'''-Demalonylsalvianin
—— 2-(3,4-dihydroxy-5-methoxyphenyl)-3,4,5-trihydroxychromen-7-one —— C16H12O8
2-(3,4-dihydroxy-5-methoxyphenyl)-3,4,5-trihydroxychromen-7-one
—— malvidin 3-O-beta-D-glucoside betaine —— C23H24O12
malvidin 3-O-beta-D-glucoside betaine
—— 2-[3-[[(2R,3R,4S,5R,6S)-5-[(2S,3R,4S,5S,6R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[7-[(2S,3R,4S,5S,6R)-6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-3-oxopropanoyl]oxy-3-hydroxybutanedioic acid —— C58H58O36
2-[3-[[(2R,3R,4S,5R,6S)-5-[(2S,3R,4S,5S,6R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[7-[(2S,3R,4S,5S,6R)-6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-3-oxopropanoyl]oxy-3-hydroxybutanedioic acid
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyran-1-ium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside —— C30H27O13+
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyran-1-ium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
—— pelargonidin-3-O-beta-D-glucoside —— C21H20O10
pelargonidin-3-O-beta-D-glucoside
—— shisonin —— C36H37O18
shisonin
—— 8-(3,7-dimethylocta-2,6-dienyl)-4,7-dihydroxy-2-phenylchromen-5-one —— C25H26O4
8-(3,7-dimethylocta-2,6-dienyl)-4,7-dihydroxy-2-phenylchromen-5-one
—— 4,7-dihydroxy-3-methoxy-8-(2-methylbut-3-en-2-yl)-2-phenylchromen-5-one —— C21H20O5
4,7-dihydroxy-3-methoxy-8-(2-methylbut-3-en-2-yl)-2-phenylchromen-5-one
—— 3,4,7-trihydroxy-2-(4-methoxyphenyl)-8-(2-methylbut-3-en-2-yl)chromen-5-one —— C21H20O6
3,4,7-trihydroxy-2-(4-methoxyphenyl)-8-(2-methylbut-3-en-2-yl)chromen-5-one