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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
—— 2-[[6-[5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 55169-25-0 C27H31O17+
2-[[6-[5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— 4-(4-oxo-4H-chromen-2-yl)benzoic acid 20093-91-8 C16H10O4
4-(4-oxo-4H-chromen-2-yl)benzoic acid
—— 2-(naphthalen-2-yl)-4H-chromen-4-one 113486-36-5 C19H12O2
2-(naphthalen-2-yl)-4H-chromen-4-one
—— 5-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one 744209-76-5 C15H10O6
5-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
—— 8-(2,2'-bithien-5-yl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran 583886-86-6 C33H22OS2
8-(2,2'-bithien-5-yl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran
—— 8-([2,2'-bithiophen]-5-ylethynyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran 316127-65-8 C35H22OS2
8-([2,2'-bithiophen]-5-ylethynyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-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-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one —— C26H28O14
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one
—— (2S,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one —— C26H30O7
(2S,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
—— 5-hydroxy-2-[4-hydroxy-3-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one 52187-80-1 C27H30O16
5-hydroxy-2-[4-hydroxy-3-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one 38965-51-4 C21H22O11
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 3',4'-dimethoxy-7-(2,3-epoxypropoxy)flavone 883242-59-9 C20H18O6
3',4'-dimethoxy-7-(2,3-epoxypropoxy)flavone
—— 3',4'-dibenzyloxy-6-(2,3-epoxypropoxy)flavone 883242-56-6 C32H26O6
3',4'-dibenzyloxy-6-(2,3-epoxypropoxy)flavone
—— 3',4'-dihydroxy-6-[3-(tert-butylamino)-2-hydroxy-propoxy]flavone 883242-78-2 C22H25NO6
3',4'-dihydroxy-6-[3-(tert-butylamino)-2-hydroxy-propoxy]flavone
—— 3',4'-dibenzyloxy-7-(2,3-epoxypropoxy)flavone 883242-55-5 C32H26O6
3',4'-dibenzyloxy-7-(2,3-epoxypropoxy)flavone
—— 3',4'-dibenzyloxy-6-hydroxyflavone 883242-52-2 C29H22O5
3',4'-dibenzyloxy-6-hydroxyflavone
—— 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,5S)-3,4,5-trihydroxy-6-[[(2R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C27H30O14
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,5S)-3,4,5-trihydroxy-6-[[(2R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— 3',4'-dibenzyloxy-6-[3-(tert-butylamino)-2-hydroxypropoxy]flavone 883242-65-7 C36H37NO6
3',4'-dibenzyloxy-6-[3-(tert-butylamino)-2-hydroxypropoxy]flavone
—— 3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin —— C42H47O23
3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin
—— cyanidin-3-glucoside —— C21H21O11*Cl
cyanidin-3-glucoside
—— 3',4'-dihydroxy-7-dimethoxyflavylium chloride 89475-36-5 C16H13O4*Cl
3',4'-dihydroxy-7-dimethoxyflavylium chloride
—— 2-(4-fluorophenyl)chroman-6-ol 488849-58-7 C15H13FO2
2-(4-fluorophenyl)chroman-6-ol
—— 5-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine Hydrochloride 488847-34-3 C22H21NO3*ClH
5-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine Hydrochloride
—— 5-butyl-10-(4-methoxyphenyl)-10-phenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 1267600-37-2 C32H27NO4
5-butyl-10-(4-methoxyphenyl)-10-phenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
—— 10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 1267600-38-3 C34H23NO4
10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
—— 4'-(4''-bromophenyl)flavone 1417919-69-7 C21H13BrO2
4'-(4''-bromophenyl)flavone
—— 2-([1,1'-biphenyl]-4-yl)-4H-chromen-4-one 41255-19-0 C21H14O2
2-([1,1'-biphenyl]-4-yl)-4H-chromen-4-one
—— 2-phenyl-3-(thiophen-3-yl)-4H-chromen-4-one 1363396-06-8 C19H12O2S
2-phenyl-3-(thiophen-3-yl)-4H-chromen-4-one
—— 2-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 1417919-67-5 C21H13FO2
2-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one
—— 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 869559-78-4 C21H13ClO2
2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one
—— 2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)ethyl 4-methoxybenzoate 1393734-53-6 C29H28O10
2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)ethyl 4-methoxybenzoate
—— 2,2,5-triphenyl-6-carboethoxy-2H-naphtho[1,2-b]pyran 402564-14-1 C34H26O3
2,2,5-triphenyl-6-carboethoxy-2H-naphtho[1,2-b]pyran
—— N(3-{1-methoxy-8-[(methylsulfonyl)amino]-6H-benzo[c]chromen-6-yl}phenyl)-N-methylbenzenesulfonamide 373622-64-1 C28H26N2O6S2
N(3-{1-methoxy-8-[(methylsulfonyl)amino]-6H-benzo[c]chromen-6-yl}phenyl)-N-methylbenzenesulfonamide
—— N-[2-(3,4-dihydroxyphenyl)-3-hydroxy-4-oxo-4H-chromen-6-yl]acetamide 260063-64-7 C17H13NO6
N-[2-(3,4-dihydroxyphenyl)-3-hydroxy-4-oxo-4H-chromen-6-yl]acetamide
—— 4-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide 1219444-71-9 C22H13F3N2O3
4-oxo-N-(pyridin-3-yl)-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxamide
—— 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid 1219446-69-1 C17H9F3O4
4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid
—— 2-(3,4-dihydroxyphenyl)-6-fluoro-3-hydroxy-4H-chromen-4-one 260063-31-8 C15H9FO5
2-(3,4-dihydroxyphenyl)-6-fluoro-3-hydroxy-4H-chromen-4-one
—— (8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid 1046469-25-3 C20H20N2O3
(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid
—— (8S)-N-ethyl-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide 1224893-48-4 C22H25N3O2
(8S)-N-ethyl-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide
—— 2-(4''-[2'''-piperidinoethoxy]phenyl)-3-(4'-tetrahydropyranyloxyphenyl)-7-tetrahydropyranyloxy-2,3-dihydro-4H-1-benzopyran-4-one 151533-32-3 C38H45NO7
2-(4''-[2'''-piperidinoethoxy]phenyl)-3-(4'-tetrahydropyranyloxyphenyl)-7-tetrahydropyranyloxy-2,3-dihydro-4H-1-benzopyran-4-one
—— Morusin-diacetat 62596-31-0 C29H28O8
Morusin-diacetat
—— Flavanon-oxim-acetat 93316-32-6 C17H15NO3
Flavanon-oxim-acetat
—— 4-(aminomethyl)-2-phenyl-4-chromanol 292836-15-8 C16H17NO2
4-(aminomethyl)-2-phenyl-4-chromanol
—— 3',4'-dibenzyloxy-7-hydroxy-flavone 307520-98-5 C29H22O5
3',4'-dibenzyloxy-7-hydroxy-flavone
—— 7-(2-bromo-ethoxy)-3',4'-dibenzyloxy-flavone 883242-80-6 C31H25BrO5
7-(2-bromo-ethoxy)-3',4'-dibenzyloxy-flavone
—— 3'-hydroxy-5,6,7-trimethoxyflavone 408337-42-8 C18H16O6
3'-hydroxy-5,6,7-trimethoxyflavone
—— 7-(2-bromo-ethoxy)-3',5'-dibenzyloxy-flavone 883242-79-3 C31H25BrO5
7-(2-bromo-ethoxy)-3',5'-dibenzyloxy-flavone
—— 4,5-dihydroxy-2-(3,5,7-trihydroxy-4-oxo-4<i>H</i>-chromen-2-yl)-benzenesulfonic acid 25001-18-7 C15H10O10S
4,5-dihydroxy-2-(3,5,7-trihydroxy-4-oxo-4<i>H</i>-chromen-2-yl)-benzenesulfonic acid
—— 2-(4-(tert-butyl)phenyl)chroman-4-one 77038-30-3 C19H20O2
2-(4-(tert-butyl)phenyl)chroman-4-one
—— 3'-(N,N-Dimethylcarbamoyloxy)flavone 405216-85-5 C18H15NO4
3'-(N,N-Dimethylcarbamoyloxy)flavone