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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-(1,3-benzodioxol-5-yl)-4-butoxy-6-methoxy-2H-chromene-3-carboxylate 1027561-01-8 C23H24O7
methyl 2-(1,3-benzodioxol-5-yl)-4-butoxy-6-methoxy-2H-chromene-3-carboxylate
—— methyl 2-(1,3-benzodioxol-5-yl)-6-methoxy-4-(4-methoxyphenyl)-2H-chromene-3-carboxylate 1028292-12-7 C26H22O7
methyl 2-(1,3-benzodioxol-5-yl)-6-methoxy-4-(4-methoxyphenyl)-2H-chromene-3-carboxylate
—— methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-propan-2-yl-2H-chromene-3-carboxylate 1026418-59-6 C28H26O6
methyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-6-propan-2-yl-2H-chromene-3-carboxylate
—— 2,2-diphenyl-2H-12H-pyrano[2,3-a]xanthene 335434-57-6 C28H20O2
2,2-diphenyl-2H-12H-pyrano[2,3-a]xanthene
—— 2-(3-hydroxy-4-methoxyphenyl)chroman-4-one 1621-70-1 C16H14O4
2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
—— 6-bromo-2-(4-bromophenyl)-3,4-dihydro-2H-chromene 80151-04-8 C15H12Br2O
6-bromo-2-(4-bromophenyl)-3,4-dihydro-2H-chromene
—— 3-(4-bromophenyl)-3-phenyl-3H-naphtho[2,1-b]pyran 1187363-44-5 C25H17BrO
3-(4-bromophenyl)-3-phenyl-3H-naphtho[2,1-b]pyran
—— 7-(3-Chloropropoxy)-2-phenylchromen-4-one 154542-00-4 C18H15ClO3
7-(3-Chloropropoxy)-2-phenylchromen-4-one
—— 7-{3-[(3-Hydroxy-benzyl)-methyl-amino]-propoxy}-2-phenyl-chromen-4-one 213891-15-7 C26H25NO4
7-{3-[(3-Hydroxy-benzyl)-methyl-amino]-propoxy}-2-phenyl-chromen-4-one
—— 7,8,4'-Trimethoxyflav-3-en 16984-93-3 C18H18O4
7,8,4'-Trimethoxyflav-3-en
—— 5,7-dimethoxy-2-(4-(1-methylpiperidin-4-yloxy)phenyl)chromen-4-one 1612891-72-1 C23H25NO5
5,7-dimethoxy-2-(4-(1-methylpiperidin-4-yloxy)phenyl)chromen-4-one
—— 5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene 859871-18-4 C36H30O4
5,7-bis(phenylmethoxy)-2-(4-phenylmethoxyphenyl)-2H-chromene
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-isobutyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 1266714-95-7 C24H26O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-isobutyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
—— (+)-ponapensin 1393487-60-9 C32H35NO8
(+)-ponapensin
—— 5,7,4'-tri-O-benzyl-3-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)kaempferol 1246814-36-7 C70H54O15
5,7,4'-tri-O-benzyl-3-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)kaempferol
—— 4',7-di-O-benzyl-5-deoxykaempferol 132020-70-3 C29H22O5
4',7-di-O-benzyl-5-deoxykaempferol
—— (2S,3R,4R,5R,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-propyltetrahydro-2H-pyran-3,5-diyl diacetate 1266714-89-9 C27H28O12
(2S,3R,4R,5R,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-propyltetrahydro-2H-pyran-3,5-diyl diacetate
—— (2S,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-propyltetrahydro-2H-pyran-3-yl acetate 1266714-93-5 C25H26O11
(2S,3R,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-propyltetrahydro-2H-pyran-3-yl acetate
—— 5,7,4'-tri-O-benzyl-3-O-(3'',6''-di-O-allyl-2'',4''-di-O-benzoyl-β-D-glucopyranosyl)kaempferol 1246814-29-8 C62H54O13
5,7,4'-tri-O-benzyl-3-O-(3'',6''-di-O-allyl-2'',4''-di-O-benzoyl-β-D-glucopyranosyl)kaempferol
—— (2S,3R,4R,5S,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-6-propyltetrahydro-2H-pyran-3,4,5-triyl triacetate 1266714-91-3 C29H30O13
(2S,3R,4R,5S,6S)-2-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-6-propyltetrahydro-2H-pyran-3,4,5-triyl triacetate
—— 5,7,4'-tri-O-benzyl-3-O-(3'',4'',6''-tri-O-benzyl-2''-O-benzoyl-β-D-glucopyranosyl)kaempferol 1246814-37-8 C70H60O12
5,7,4'-tri-O-benzyl-3-O-(3'',4'',6''-tri-O-benzyl-2''-O-benzoyl-β-D-glucopyranosyl)kaempferol
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-propyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 1266714-90-2 C23H24O10
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-propyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
—— (2S,3S,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-2-propyltetrahydro-2H-pyran-3,4-diyl diacetate 1266714-94-6 C27H28O12
(2S,3S,4S,5R,6S)-6-((5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)-5-hydroxy-2-propyltetrahydro-2H-pyran-3,4-diyl diacetate
—— 5,7,4'-tri-O-benzyl-3-O-(2'',4''-di-O-benzoyl-3''-O-benzyl-α-L-rhamnopyranosyl)kaempferol 1246814-38-9 C63H52O12
5,7,4'-tri-O-benzyl-3-O-(2'',4''-di-O-benzoyl-3''-O-benzyl-α-L-rhamnopyranosyl)kaempferol
—— 3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 1012306-94-3 C22H22O10
3-(((2S,3R,4R,5R,6S)-6-ethyl-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
—— 5,7,4'-tri-O-benzyl-3-O-(2'',3'',5''-tri-O-benzoyl-β-D-ribofuranosyl)kaempferol 1246814-39-0 C62H48O13
5,7,4'-tri-O-benzyl-3-O-(2'',3'',5''-tri-O-benzoyl-β-D-ribofuranosyl)kaempferol
—— 4-oxo-2-phenyl-4<i>H</i>-chromene-7-carboxylic acid 14221-75-1 C16H10O4
4-oxo-2-phenyl-4<i>H</i>-chromene-7-carboxylic acid
—— methyl 2-(1,3-benzodioxol-5-yl)-7-propoxy-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate 1026714-86-2 C22H19F3O9S
methyl 2-(1,3-benzodioxol-5-yl)-7-propoxy-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate
—— methyl 2-(1,3-benzodioxol-5-yl)-6-propan-2-yl-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate 1027039-02-6 C22H19F3O8S
methyl 2-(1,3-benzodioxol-5-yl)-6-propan-2-yl-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate
—— methyl 2-(1,3-benzodioxol-5-yl)-6-methoxy-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate 1028288-79-0 C20H15F3O9S
methyl 2-(1,3-benzodioxol-5-yl)-6-methoxy-4-(trifluoromethylsulfonyloxy)-2H-chromene-3-carboxylate
—— (2S)-5,6,7-Trimethoxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one 78548-22-8 C18H18O5
(2S)-5,6,7-Trimethoxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
—— 2-(3-methoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 66848-80-4 C17H12O5
2-(3-methoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— 7,8-Dihydroxy-4'-methoxy-flavon 65894-01-1 C16H12O5
7,8-Dihydroxy-4'-methoxy-flavon
—— 9-Methylfuro<2,3-h>flavone 65679-20-1 C18H12O3
9-Methylfuro<2,3-h>flavone
—— 3,6-Dichloro-2-(4-fluorophenyl)chromen-4-one 1260668-00-5 C15H7Cl2FO2
3,6-Dichloro-2-(4-fluorophenyl)chromen-4-one
—— (+)-Fustin 4382-36-9 C15H12O6
(+)-Fustin
—— 2-(3,4-bis(methoxymethoxy)phenyl)-6-amino-3-hydroxy-4H-chromen-4-one 1609456-24-7 C19H19NO7
2-(3,4-bis(methoxymethoxy)phenyl)-6-amino-3-hydroxy-4H-chromen-4-one
—— 6,8-dibromo-3-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 260063-34-1 C15H8Br2O5
6,8-dibromo-3-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one
—— 6-amino-3-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 260063-29-4 C15H11NO5
6-amino-3-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one
—— (+/-)-fustin tetraacetate 104435-37-2 C23H20O10
(+/-)-fustin tetraacetate
—— 6",6"-dimethyl-4",5"-dihydropyrano(2",3":7,6)-5,3',4'-trihydroxyflavanone 132339-92-5 C20H20O6
6",6"-dimethyl-4",5"-dihydropyrano(2",3":7,6)-5,3',4'-trihydroxyflavanone
—— 6",6"-dimethyl-4",5"-dihydropyrano(2",3":7,8)-5,3',4'-trihydroxyflavanone 132339-94-7 C20H20O6
6",6"-dimethyl-4",5"-dihydropyrano(2",3":7,8)-5,3',4'-trihydroxyflavanone
—— 6-bromo-4-oxo-2-phenyl-4H-chromen-3-yl trifluoromethanesulfonate 1446340-52-8 C16H8BrF3O5S
6-bromo-4-oxo-2-phenyl-4H-chromen-3-yl trifluoromethanesulfonate
—— 3-bromo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one 215999-44-3 C16H11BrO4S
3-bromo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one
—— 2-(4'-Fluorophenyl)-3-methyl-5,7-dimethoxy-4H-1-benzopyran-4-one 132313-28-1 C18H15FO4
2-(4'-Fluorophenyl)-3-methyl-5,7-dimethoxy-4H-1-benzopyran-4-one
—— 2-(4'-Fluorophenyl)-3-methyl-5,7-dihydroxy-4H-1-benzopyran-4-one 132313-29-2 C16H11FO4
2-(4'-Fluorophenyl)-3-methyl-5,7-dihydroxy-4H-1-benzopyran-4-one
—— 2-(4-benzyloxyphenyl)-3-hydroxy-4H-chromen-4-one 102468-65-5 C22H16O4
2-(4-benzyloxyphenyl)-3-hydroxy-4H-chromen-4-one
—— 2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethyl-4H-chromen-4-one 1081315-34-5 C18H16O4
2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethyl-4H-chromen-4-one
—— 2-phenyl-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one 99874-96-1 C18H12N2O2
2-phenyl-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one
—— trans-2-phenyl-3-(1H-imidazol-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one 85928-46-7 C18H14N2O2
trans-2-phenyl-3-(1H-imidazol-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one