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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
—— 7-O-[β-D-Glcp-O-β-D-Glcp]2-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)-epigallocatechin]-(4β-8)-3-O-galloyl-(-)-epigallocatechin —— C112H106O64
7-O-[β-D-Glcp-O-β-D-Glcp]2-3-O-galloyl-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)-epigallocatechin]-(4β-8)-3-O-galloyl-(-)-epigallocatechin
—— myricatin —— C22H15O15S*K
myricatin
—— gallocatechin-(4α->8)-catechin —— C37H30O16
gallocatechin-(4α->8)-catechin
—— quercetin-3-O-rutinoside 207671-50-9 C27H30O16*3H2O
quercetin-3-O-rutinoside
—— scutellarin arginine salt —— C6H14N4O2*C21H18O12
scutellarin arginine salt
—— 4'-chloro-6-methoxyflavanone —— C16H13ClO3
4'-chloro-6-methoxyflavanone
—— 2-(4-isopropylphenyl)chroman-4-one —— C18H18O2
2-(4-isopropylphenyl)chroman-4-one
—— (3S,4S)-4-[(2S)-3,4-dihydro-7-hydroxy-4-oxo-2-phenyl-2H-1-benzopyran-8-yl]tetrahydro-2,2-dimethyl-3-furanyl (2E)-3-phenyl-2-propenoate —— C30H28O6
(3S,4S)-4-[(2S)-3,4-dihydro-7-hydroxy-4-oxo-2-phenyl-2H-1-benzopyran-8-yl]tetrahydro-2,2-dimethyl-3-furanyl (2E)-3-phenyl-2-propenoate
—— apigenin-7-galacturonic acid methyl ester —— C22H20O11
apigenin-7-galacturonic acid methyl ester
—— luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide> —— C27H26O18
luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide>
—— kaempferol 3-glucuronide-7-glucoside —— C27H28O17
kaempferol 3-glucuronide-7-glucoside
—— quercetin 3-O-β-glucopyranoside uronic acid 7-O-β-glucopyranoside —— C27H28O18
quercetin 3-O-β-glucopyranoside uronic acid 7-O-β-glucopyranoside
—— quercetin 3-glucuronide-3'-sulphate —— C21H17O16S*K
quercetin 3-glucuronide-3'-sulphate
—— Rhamnetin 3-glucuronide —— C22H20O13
Rhamnetin 3-glucuronide
—— cyanidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside] —— C64H67O41
cyanidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside]
—— delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside] —— C64H67O42
delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside]
—— delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside] —— C57H61O34
delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside]
—— delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside] —— C58H59O36
delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(2-O-(tartaryl)malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]
—— delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside] —— C60H63O37
delphinidin 3-O-[2-O-(2-(trans-caffeoyl)-β-D-glucopyranosyl)-6-O-(malonyl)-β-D-galactopyranoside]-7-O-[6-O-(trans-caffeoyl)-β-D-glucopyranoside]-3'-O-[β-D-glucuronopyranoside]
—— 3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-7-(3,7,11-trimethyl-dodecyl)-chromen-4-one —— C30H40O6
3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-7-(3,7,11-trimethyl-dodecyl)-chromen-4-one
—— (-)-epicatechin —— C15H14O6
(-)-epicatechin
—— luteolin-7-O-(2″-O-caffeoyl)-β-D-glucopyranoside —— C30H26O14
luteolin-7-O-(2″-O-caffeoyl)-β-D-glucopyranoside
—— 3-[N-(4-carboxybenzyl)amino]methylidene-flavanone —— C24H19NO4
3-[N-(4-carboxybenzyl)amino]methylidene-flavanone
—— 3-hydroxymethylidene-flavanone —— C16H12O3
3-hydroxymethylidene-flavanone
—— (2R,3R)-3,5,7,3',5'-pentahydroxyflavan —— C15H14O6
(2R,3R)-3,5,7,3',5'-pentahydroxyflavan
—— delphinidin 3-O-[6-O-malonyl-β-D-glucopyranoside]-7-O-[6-O-(4-O-(6-O-(4-O-(β-D-glucopyranosyl)-trans-caffeoyl)-β-D-glucopyranosyl)-trans-caffeoyl)-β-D-glucopyranoside] —— C60H65O36
delphinidin 3-O-[6-O-malonyl-β-D-glucopyranoside]-7-O-[6-O-(4-O-(6-O-(4-O-(β-D-glucopyranosyl)-trans-caffeoyl)-β-D-glucopyranosyl)-trans-caffeoyl)-β-D-glucopyranoside]
—— delphinidin 3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside —— C27H31O17
delphinidin 3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside
—— delphinidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside] —— C65H67O35
delphinidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside]
—— cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside] —— C65H67O34
cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside]
—— quercetin 3-<6-caffeyl-β-D-glucopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside> —— C42H46O25
quercetin 3-<6-caffeyl-β-D-glucopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside>
—— kaempferol 3-O-[(6-O-E-caffeoyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside —— C42H44O25
kaempferol 3-O-[(6-O-E-caffeoyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside
—— (2R,3R)-3-hydroxy-6-methoxy-2-(3-methoxyphenyl)chroman-4-one —— C17H16O5
(2R,3R)-3-hydroxy-6-methoxy-2-(3-methoxyphenyl)chroman-4-one
—— (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl stearate —— C40H56O13
(6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl stearate
—— 3-O-(N,N-diethylamino)butyl-3',4'-dimethoxyflavonol —— C25H31NO5
3-O-(N,N-diethylamino)butyl-3',4'-dimethoxyflavonol
—— 3-(3-(diethylamino-1-yl)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromene-4-one —— C27H35NO8
3-(3-(diethylamino-1-yl)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromene-4-one
—— (+)-trans-2-(2-chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one —— C23H24ClNO5
(+)-trans-2-(2-chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one
—— 3,5,7-trihydroxy-2-[8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one —— C25H22O11
3,5,7-trihydroxy-2-[8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
—— (+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one —— C21H18Cl2FNO5
(+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one
—— (+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one tartarate —— C4H6O6*C21H18Cl2FNO5
(+)-trans-2-(2,4-dichloro-5-fluorophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one tartarate
—— 3,7-bis{[8-(diethylamino)octyl]oxy}-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one —— C45H70N2O6
3,7-bis{[8-(diethylamino)octyl]oxy}-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
—— 3,7-bis[2-(diethylamino)ethoxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one —— C33H46N2O6
3,7-bis[2-(diethylamino)ethoxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
—— 4,4'-{2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]diethoxy}bis(4-oxobutanoic acid) —— C33H36O14
4,4'-{2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]diethoxy}bis(4-oxobutanoic acid)
—— 4-[(3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy]butyric acid —— C25H26O8
4-[(3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy]butyric acid
—— 2-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]acetic acid —— C23H22O8
2-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]acetic acid
—— 4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dibutyric acid —— C29H32O10
4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dibutyric acid
—— 4-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]butyric acid —— C25H26O8
4-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]butyric acid
—— 4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dicrotonic acid —— C29H28O10
4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dicrotonic acid
—— 4,4'-{3,3'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropoxy}bis(4-oxobutanoic acid) —— C35H40O14
4,4'-{3,3'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropoxy}bis(4-oxobutanoic acid)
—— 4-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]crotonic acid —— C25H24O8
4-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]crotonic acid
—— 2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropionic acid —— C27H28O10
2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dipropionic acid