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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
—— 6-chloro-3-(1-naphthylmethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one 887860-39-1 C27H19ClO4
6-chloro-3-(1-naphthylmethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one
—— 6-chloro-3-(1-naphthylmethoxy)-2-phenyl-4H-chromen-4-one 877292-62-1 C26H17ClO3
6-chloro-3-(1-naphthylmethoxy)-2-phenyl-4H-chromen-4-one
—— 6-chloro-3-(1-naphthylmethoxy)-2-(4-methylphenyl)-4H-chromen-4-one 877273-52-4 C27H19ClO3
6-chloro-3-(1-naphthylmethoxy)-2-(4-methylphenyl)-4H-chromen-4-one
—— 4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 1-methyl-2-(1-piperidinyl)ethyl ester, hydrochloride, hydrate 86433-61-6 C25H28ClNO4
4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 1-methyl-2-(1-piperidinyl)ethyl ester, hydrochloride, hydrate
—— N-methyl-3-piperidyl 3-methylflavone-8-carboxylate hydrochloride —— C23H23NO4*ClH
N-methyl-3-piperidyl 3-methylflavone-8-carboxylate hydrochloride
—— hydron;[(1R,2S)-2-piperidin-1-ylcyclohexyl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;chloride —— C28H32ClNO4
hydron;[(1R,2S)-2-piperidin-1-ylcyclohexyl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;chloride
—— 4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-hydroxy-3-(1-piperidinyl)propyl ester, hydrochloride 86433-58-1 C25H28ClNO5
4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-hydroxy-3-(1-piperidinyl)propyl ester, hydrochloride
—— naringenin 4'-O-β-D-glucuronide 1237479-04-7 C21H20O11
naringenin 4'-O-β-D-glucuronide
—— hydron;(1-phenyl-2-piperidin-1-ylethyl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;chloride —— C30H30ClNO4
hydron;(1-phenyl-2-piperidin-1-ylethyl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;chloride
—— 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-6-(1-piperidinylmethyl)-, (S)- 183051-61-8 C21H23NO4
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-6-(1-piperidinylmethyl)-, (S)-
—— 2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-butyric acid 173469-88-0 C26H22O5
2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-butyric acid
—— 2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-butyric acid methyl ester 173469-86-8 C27H23ClO5
2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-butyric acid methyl ester
—— methyl 2-(3-methyl-2-phenylchromon-6-yl)butanoate 173469-71-1 C21H20O4
methyl 2-(3-methyl-2-phenylchromon-6-yl)butanoate
—— 2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-butyric acid methyl ester 173469-84-6 C27H24O5
2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-butyric acid methyl ester
—— 2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-butyric acid 173469-90-4 C26H21ClO5
2-[3-Benzyloxy-2-(4-chloro-phenyl)-4-oxo-4H-chromen-6-yl]-butyric acid
—— Wushanicariin 115516-53-5 C27H30O11
Wushanicariin
—— (S)-2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one 38965-51-4 C21H22O11
(S)-2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-4H-1-benzopyran-4-one
—— 6-Methoxy-2-(4-nitrophenyl)-2H-1-benzopyran 887406-88-4 C16H13NO4
6-Methoxy-2-(4-nitrophenyl)-2H-1-benzopyran
—— Fragarin 574-57-2 C21H22O11
Fragarin
—— 8-fluoro-2-phenyl-4H-chromen-4-one 2558-21-6 C15H9FO2
8-fluoro-2-phenyl-4H-chromen-4-one
—— 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside —— C27H30O14
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
—— 2-(3,4-bis-trimethylsilanyloxy-phenyl)-3-hydroxy-5,7-bis-trimethylsilanyloxy-chromen-4-one 78599-47-0 C27H42O7Si4
2-(3,4-bis-trimethylsilanyloxy-phenyl)-3-hydroxy-5,7-bis-trimethylsilanyloxy-chromen-4-one
—— Malvidin 3-arabinoside 679429-95-9 C22H23ClO11
Malvidin 3-arabinoside
—— 7-[(2S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one —— C28H34O15
7-[(2S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
—— hesperetin 7-O-β-D-glucopyranoside 906320-94-3 C22H24O11
hesperetin 7-O-β-D-glucopyranoside
—— Rhodionidin 94696-40-9 C27H30O16
Rhodionidin
—— 6-(tert-butyl)-2-phenyl-4H-chromen-4-one 13448-23-2 C19H18O2
6-(tert-butyl)-2-phenyl-4H-chromen-4-one
—— eriodictyol 7-neohesperidoside 13241-32-2 C27H32O15
eriodictyol 7-neohesperidoside
—— (2S,2''S)-tetrahydroamentoflavone 48236-96-0 C30H22O10
(2S,2''S)-tetrahydroamentoflavone
—— Flavopiridol hydrochloride hydrate —— C21H23Cl2NO6
Flavopiridol hydrochloride hydrate
—— Primulin 30113-37-2 C23H25O12+
Primulin
—— Grape Seed P.E. —— C32H30O11
Grape Seed P.E.
—— 3-Ethyl-8-(ethylaminomethyl)-7-hydroxy-2-phenylchromen-4-one;hydrochloride 67238-77-1 C20H22ClNO3
3-Ethyl-8-(ethylaminomethyl)-7-hydroxy-2-phenylchromen-4-one;hydrochloride
—— 3-Ethyl-7-hydroxy-8-(methylaminomethyl)-2-phenylchromen-4-one;hydrochloride 67238-79-3 C19H20ClNO3
3-Ethyl-7-hydroxy-8-(methylaminomethyl)-2-phenylchromen-4-one;hydrochloride
—— 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, sodium salt 22519-99-9 C27H30NaO16+
3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, sodium salt
—— Di-O-(beta-hydroxyethyl)rutoside 26854-07-9 C31H40O19
Di-O-(beta-hydroxyethyl)rutoside
—— 8,8''-Methylenebis(6-((diethylamino)methyl)rutin 17307-03-8 C65H82N2O32
8,8''-Methylenebis(6-((diethylamino)methyl)rutin
—— 4H-1-Benzopyran-4-one-3-[[6-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy hydrogen sulfat e sodium salt —— C27H32O20S
4H-1-Benzopyran-4-one-3-[[6-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy hydrogen sulfat e sodium salt
—— (3R)-3-phenyl-2,3-dihydrobenzo[f]chromen-1-one 1413433-51-8 C19H14O2
(3R)-3-phenyl-2,3-dihydrobenzo[f]chromen-1-one
—— alpha-naphthoflavanone 1413433-55-2 C19H14O2
alpha-naphthoflavanone
—— 2-[7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 16727-30-3 C29H35O17+
2-[7-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— (2S,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methyl-2,3-dihydrochromen-4-one 132147-69-4 C16H14O5
(2S,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methyl-2,3-dihydrochromen-4-one
—— 1,3,3',5'-Tetrabromophlorhizin 86158-06-7 C21H20Br4O10
1,3,3',5'-Tetrabromophlorhizin
—— Benzeneacetic acid, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-trans)- 71627-91-3 C23H20O7
Benzeneacetic acid, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-trans)-
—— 8,14-Methano-4H,14H-1-benzopyrano(7,8-d)(1,3)benzodioxocin-4-one, 2,8-bis(3,4-dihydroxyphenyl)-11-(beta-D-glucopyranosyloxy)-2,3-dihydro-5,13-dihydroxy-, (2R,8R,14R)- 176739-79-0 C36H32O16
8,14-Methano-4H,14H-1-benzopyrano(7,8-d)(1,3)benzodioxocin-4-one, 2,8-bis(3,4-dihydroxyphenyl)-11-(beta-D-glucopyranosyloxy)-2,3-dihydro-5,13-dihydroxy-, (2R,8R,14R)-
—— Minimiflorin 98621-33-1 C25H26O5
Minimiflorin
—— Dioflorin 204127-54-8 C21H22O6
Dioflorin
—— Dehydrodicatechin A 31551-50-5 C30H24O12
Dehydrodicatechin A
—— 3-((O-(6-Deoxymannosyl)glucosyl)oxy)-3',4',5,5',7-pentahydroxyflavylium chloride 29732-48-7 C27H31ClO16
3-((O-(6-Deoxymannosyl)glucosyl)oxy)-3',4',5,5',7-pentahydroxyflavylium chloride
—— 6-Chloro-2-(2,4-dichlorophenyl)chroman-4-one 70460-48-9 C15H9Cl3O2
6-Chloro-2-(2,4-dichlorophenyl)chroman-4-one