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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
—— (+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one citrate —— C6H8O7*C21H18Cl2FNO5
(+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one citrate
—— (2S)-5-hydroxy-7-methoxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one —— C21H22O4
(2S)-5-hydroxy-7-methoxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
—— pinocembrin 8-C-β-D-glucoside —— C21H22O9
pinocembrin 8-C-β-D-glucoside
—— (S)-5,7-dihydroxy-6,8-di((1-morpholino)-methyl)-flavanone —— C25H30N2O6
(S)-5,7-dihydroxy-6,8-di((1-morpholino)-methyl)-flavanone
—— 5-hydroxy-7-methoxyflavan —— C16H16O3
5-hydroxy-7-methoxyflavan
—— (2S)-8-formyl-5,7-dihydroxyflavanone —— C16H12O5
(2S)-8-formyl-5,7-dihydroxyflavanone
—— (2S)-6-formyl-5,7-dihydroxyflavanone —— C16H12O5
(2S)-6-formyl-5,7-dihydroxyflavanone
—— (2R)-8-formyl-5,7-dihydroxyflavanone —— C16H12O5
(2R)-8-formyl-5,7-dihydroxyflavanone
—— 6-C,7-O-diprenylpinocembrin —— C25H28O4
6-C,7-O-diprenylpinocembrin
—— (2R)-6-formyl-5,7-dihydroxyflavanone —— C16H12O5
(2R)-6-formyl-5,7-dihydroxyflavanone
—— 7-ethoxy-2-(3,4-diethoxy-phenyl)-5-hydroxy-chromen-4-one —— C21H22O6
7-ethoxy-2-(3,4-diethoxy-phenyl)-5-hydroxy-chromen-4-one
—— cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt —— C2F3O2*C21H21O11
cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt
—— 4'-tert-butyl-5-hydroxyflavanone —— C19H20O3
4'-tert-butyl-5-hydroxyflavanone
—— 3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy}phenyl)-2H-chromen-7-ol —— C29H31NO4
3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy}phenyl)-2H-chromen-7-ol
—— EM-776 —— C39H47NO6
EM-776
—— 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-(3-hydroxypropylamino)-4H-1-benzopyran-4-one —— C23H23F3N2O4
6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-(3-hydroxypropylamino)-4H-1-benzopyran-4-one
—— 3-benzyloxy-7-octyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one —— C33H38O6
3-benzyloxy-7-octyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
—— 7-ethoxy-5-hydroxy-2-(4-methoxy-phenyl)-chroman-4-one —— C18H18O5
7-ethoxy-5-hydroxy-2-(4-methoxy-phenyl)-chroman-4-one
—— 1-benzyl-4-(((2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)-phenyl)chroman-3-yloxy)methyl)-1H-1,2,3-triazole —— C53H47N3O6
1-benzyl-4-(((2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)-phenyl)chroman-3-yloxy)methyl)-1H-1,2,3-triazole
—— (2S,3R)-taxifolin 3-β-D-glucopyranoside —— C21H22O12
(2S,3R)-taxifolin 3-β-D-glucopyranoside
—— taxifolin 3-O-β-D-galactopyranosyl (1<*>6)-O-β-D-glucopyranoside —— C27H32O17
taxifolin 3-O-β-D-galactopyranosyl (1<*>6)-O-β-D-glucopyranoside
—— (2R,3R)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-2-(3,4-dihydroxyphenyl)chroman-5,7-diol —— C25H23N3O6
(2R,3R)-3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-2-(3,4-dihydroxyphenyl)chroman-5,7-diol
—— cis-dihydroquercetin 3-acetate —— C17H14O8
cis-dihydroquercetin 3-acetate
—— (6R,6aS,11bS)-6-(3,4-dimethoxyphenyl)-1,3,9,11-tetramethoxy-6a,11b-dihydro-6H-[1]benzofuro[2,3-c]chromene —— C27H28O8
(6R,6aS,11bS)-6-(3,4-dimethoxyphenyl)-1,3,9,11-tetramethoxy-6a,11b-dihydro-6H-[1]benzofuro[2,3-c]chromene
—— dihydroquercetin 7-acetate —— C17H14O8
dihydroquercetin 7-acetate
—— 3,3',4',7-tetra-O-tert-butyldimethylsilyltaxifolin —— C39H68O7Si4
3,3',4',7-tetra-O-tert-butyldimethylsilyltaxifolin
—— procyanidin trimer —— C45H38O18
procyanidin trimer
—— taxifolin 3'-O-sulfate —— C15H12O10S
taxifolin 3'-O-sulfate
—— (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochroman-7-yl cinnamate —— C24H18O8
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochroman-7-yl cinnamate
—— 3,3',4',5,7-penta-O-tert-butyldimethylsilyltaxifolin —— C45H82O7Si5
3,3',4',5,7-penta-O-tert-butyldimethylsilyltaxifolin
—— (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochroman-7-yl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate —— C25H20O10
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochroman-7-yl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
—— taxifolin 4'-O-β-D-glucopyranoside —— C21H22O12
taxifolin 4'-O-β-D-glucopyranoside
—— taxifolin 3'-O-β-D-(6''-O-phenylacetyl)-glucopyranoside —— C29H28O13
taxifolin 3'-O-β-D-(6''-O-phenylacetyl)-glucopyranoside
—— isoglucodistylin —— C21H22O12
isoglucodistylin
—— (+)-taxifolin-3-O-β-D-apio-D-furanoside —— C20H20O11
(+)-taxifolin-3-O-β-D-apio-D-furanoside
—— (+)-taxifolin 3-O-α-L-arabinofuranoside —— C20H20O11
(+)-taxifolin 3-O-α-L-arabinofuranoside
—— 2-[4-(4-bromobutoxy)-phenyl]-4H-1-benzopyran-4-one —— C19H17BrO3
2-[4-(4-bromobutoxy)-phenyl]-4H-1-benzopyran-4-one
—— 4'-(4-(benzyl(ethyl)amino)butoxy)-5,6,7-trimethoxyflavone —— C31H35NO6
4'-(4-(benzyl(ethyl)amino)butoxy)-5,6,7-trimethoxyflavone
—— 4'-(3-(benzyl(ethyl)amino)propoxy)-5,6,7-trimethoxyflavone —— C30H33NO6
4'-(3-(benzyl(ethyl)amino)propoxy)-5,6,7-trimethoxyflavone
—— 4'-(6-(benzyl(ethyl)amino)hexyloxy)-5,6,7-trimethoxyflavone —— C33H39NO6
4'-(6-(benzyl(ethyl)amino)hexyloxy)-5,6,7-trimethoxyflavone
—— 3'-(3-(benzyl(ethyl)amino)ethoxy)-5,6,7-trimethoxyflavone —— C29H31NO6
3'-(3-(benzyl(ethyl)amino)ethoxy)-5,6,7-trimethoxyflavone
—— 3'-(3-(benzyl(ethyl)amino)propoxy)-5,6,7-trimethoxyflavone —— C30H33NO6
3'-(3-(benzyl(ethyl)amino)propoxy)-5,6,7-trimethoxyflavone
—— 3'-(4-(benzyl(ethyl)amino)butoxy)-5,6,7-trimethoxyflavone —— C31H35NO6
3'-(4-(benzyl(ethyl)amino)butoxy)-5,6,7-trimethoxyflavone
—— 3'-(6-(benzyl(ethyl)amino)hexyloxy)-5,6,7-trimethoxyflavone —— C33H39NO6
3'-(6-(benzyl(ethyl)amino)hexyloxy)-5,6,7-trimethoxyflavone
—— (2S,3R)-2-amino-9-methoxy-3-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-benzo[f]chromen-8-nitrile —— C21H15F3N2O2
(2S,3R)-2-amino-9-methoxy-3-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-benzo[f]chromen-8-nitrile
—— 5-(5-bromopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one —— C25H26BrF3N2O3
5-(5-bromopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one
—— 7-(4-cyanobutoxy)-2-phenyl-4H-1-benzopyran-4-one —— C20H17NO3
7-(4-cyanobutoxy)-2-phenyl-4H-1-benzopyran-4-one
—— 3-O-((2-acetoxy)benzoyl)-3',4',7-tris(-O-hydroxyethyl)quercetin —— C30H28O13
3-O-((2-acetoxy)benzoyl)-3',4',7-tris(-O-hydroxyethyl)quercetin
—— 2-phenyl-2H-benzo[h]chromene —— C19H14O
2-phenyl-2H-benzo[h]chromene
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl benzoate —— C27H22O8
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl benzoate