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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
—— dibenzyl (4-((2R,3R)-5,7-bis(((benzyloxy)carbonyl)oxy)-3-hydroxychroman-2-yl)-1,2-phenylene)bis(carbonate) —— C47H38O14
dibenzyl (4-((2R,3R)-5,7-bis(((benzyloxy)carbonyl)oxy)-3-hydroxychroman-2-yl)-1,2-phenylene)bis(carbonate)
—— 6-Cyanomethyl-2-(p-chlorophenyl)chromone —— C17H10ClNO2
6-Cyanomethyl-2-(p-chlorophenyl)chromone
—— 2-(4-chlorophenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one —— C16H11ClO5
2-(4-chlorophenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-one
—— 2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-6,8-dimethyl-chroman-4-one —— C18H16O6
2-benzo[1,3]dioxol-5-yl-5,7-dihydroxy-6,8-dimethyl-chroman-4-one
—— 3',4'-dimethoxy-7,8-dimethylflavone —— C19H18O4
3',4'-dimethoxy-7,8-dimethylflavone
—— Herbacetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid —— C33H40O22
Herbacetin-3-β-D-(2-O-β-D-glucopyranosidoglucopyranosid)-8-β-D-glucopyranosid
—— herbacetin 3-O-α-L-rhamnopyranoside 8-O-β-D-glucopyranoside —— C27H30O16
herbacetin 3-O-α-L-rhamnopyranoside 8-O-β-D-glucopyranoside
—— [5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-6-yl]-acetic acid —— C20H18O7
[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-6-yl]-acetic acid
—— 1-N-benzylspiro[3.3<sup>1</sup>]flavan-4<sup>1</sup>-one-4-(4-chlorophenyl)pyrrolidine —— C31H26ClNO2
1-N-benzylspiro[3.3<sup>1</sup>]flavan-4<sup>1</sup>-one-4-(4-chlorophenyl)pyrrolidine
—— 1-N-benzylspiro[3.3<sup>1</sup>]flavan-4<sup>1</sup>-one-4-(4-methoxyphenyl)pyrrolidine —— C32H29NO3
1-N-benzylspiro[3.3<sup>1</sup>]flavan-4<sup>1</sup>-one-4-(4-methoxyphenyl)pyrrolidine
—— quercetin 3-O-β-D-(3-O-acetyl)glucopyranosyl-7-O-α-L-rhamnopyranoside —— C29H32O17
quercetin 3-O-β-D-(3-O-acetyl)glucopyranosyl-7-O-α-L-rhamnopyranoside
—— quercetin 3-O-β-D-glucopyranosyl-7-O-α-L-(3-O-isobutyryl)rhamnopyranoside —— C31H36O17
quercetin 3-O-β-D-glucopyranosyl-7-O-α-L-(3-O-isobutyryl)rhamnopyranoside
—— 5R*-(+)-2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethanol —— C37H50O6Si2
5R*-(+)-2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethanol
—— 2-(4-(2-((S)-2-(fluoromethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C29H30FNO4
2-(4-(2-((S)-2-(fluoromethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— (3R)-1-(2-(4-(6-hydroxy-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-2-yl)phenoxy)ethyl)pyrrolidine-3-carbonitrile —— C29H28N2O4
(3R)-1-(2-(4-(6-hydroxy-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-2-yl)phenoxy)ethyl)pyrrolidine-3-carbonitrile
—— 2-(4-(2-(4-(fluoromethyl)piperidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C30H32FNO4
2-(4-(2-(4-(fluoromethyl)piperidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— 2-(4-((S)-2-(3-(fluoromethyl)azetidin-1-yl)propoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C29H30FNO4
2-(4-((S)-2-(3-(fluoromethyl)azetidin-1-yl)propoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— 3-(3-hydroxyphenyl)-2-(4-(2-((R)-3-(methoxymethyl)pyrrolidin-1-yl)ethoxy)phenyl)-4-methyl-2H-chromen-6-ol —— C30H33NO5
3-(3-hydroxyphenyl)-2-(4-(2-((R)-3-(methoxymethyl)pyrrolidin-1-yl)ethoxy)phenyl)-4-methyl-2H-chromen-6-ol
—— 2-(4-(2-((R)-3-(difluoromethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C29H29F2NO4
2-(4-(2-((R)-3-(difluoromethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— 2-(4-(2-((R)-3-(fluoroinethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C29H30FNO4
2-(4-(2-((R)-3-(fluoroinethyl)pyrrolidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— (R)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C28H28FNO4
(R)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— (S)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol hydrochloride —— C28H28FNO4*ClH
(S)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol hydrochloride
—— (±)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol —— C28H28FNO4
(±)-2-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— 4'-O-[β-D-apiosyl(1->2)-β-D-glucopyranosyl]-5-hydroxyl-7-O-sinapylflavanone —— C37H40O18
4'-O-[β-D-apiosyl(1->2)-β-D-glucopyranosyl]-5-hydroxyl-7-O-sinapylflavanone
—— 8-hydroxyliquiritigenin —— C15H12O5
8-hydroxyliquiritigenin
—— (2S)-(-)-7,8-dihydroxylflavanone-4'-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside —— C26H30O14
(2S)-(-)-7,8-dihydroxylflavanone-4'-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside
—— variabiloside F —— C36H36O18
variabiloside F
—— variabiloside B —— C42H46O23
variabiloside B
—— kaempferol 3-(4"-cis-p-coumaroyl)robinobioside —— C36H36O17
kaempferol 3-(4"-cis-p-coumaroyl)robinobioside
—— variabiloside D —— C42H46O22
variabiloside D
—— quercetin-3-O-(6''-O-E-p-feruloyl)-β-D-glucopyranoside —— C31H28O15
quercetin-3-O-(6''-O-E-p-feruloyl)-β-D-glucopyranoside
—— ((2R,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl benzoate —— C28H24O13
((2R,3S,4S,5R,6S)-6-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl benzoate
—— isoquercitrin 4'-O-sulfate —— C21H20O15S
isoquercitrin 4'-O-sulfate
—— phlomisflavoside A —— C26H28O16
phlomisflavoside A
—— ethyl-9-chloro-2-methyl-5-(4-methoxy phenyl)-5H-chromene[3,4-c]pyridine-1-carboxylate —— C23H20ClNO4
ethyl-9-chloro-2-methyl-5-(4-methoxy phenyl)-5H-chromene[3,4-c]pyridine-1-carboxylate
—— 4,6-dichloro-2-(4-methoxy phenyl)-2H-3-chromene carbaldehyde —— C17H12Cl2O3
4,6-dichloro-2-(4-methoxy phenyl)-2H-3-chromene carbaldehyde
—— 4,8-dichloro-2-(4-chloro phenyl)-2H-3-chromenecarbaldehyde —— C16H9Cl3O2
4,8-dichloro-2-(4-chloro phenyl)-2H-3-chromenecarbaldehyde
—— ethyl-9-chloro-2-methyl-5-(3,4-dimethoxy phenyl)-5H-chromene[3,4-c]pyridine-1-carboxylate —— C24H22ClNO5
ethyl-9-chloro-2-methyl-5-(3,4-dimethoxy phenyl)-5H-chromene[3,4-c]pyridine-1-carboxylate
—— 3,3-diphenyl-9,10,12,13,15,16,18,19,21,22-decahydro-3H-[1,4,10,13]tetraoxa[7,16]dithiacyclooctadeca[2′,3′:4,5]benzo[f]chromene —— C35H36O5S2
3,3-diphenyl-9,10,12,13,15,16,18,19,21,22-decahydro-3H-[1,4,10,13]tetraoxa[7,16]dithiacyclooctadeca[2′,3′:4,5]benzo[f]chromene
—— 7-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one —— C16H9F3O3
7-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one
—— 2,3-dihydroquercetin 7-(diethylamido)butylthionophosphate —— C23H30NO8PS
2,3-dihydroquercetin 7-(diethylamido)butylthionophosphate
—— 7-(N,N-diethylamino)-4’-hydroxyflavylium —— C19H20NO2
7-(N,N-diethylamino)-4’-hydroxyflavylium
—— 6-(4-methoxyphenyl)-6H-benzo[c]chromene —— C20H16O2
6-(4-methoxyphenyl)-6H-benzo[c]chromene
—— 2,3-trans-[(+/-)3-O-(3,4,5-trimethoxybenzoyl) epigallocatechin] —— C25H24O11
2,3-trans-[(+/-)3-O-(3,4,5-trimethoxybenzoyl) epigallocatechin]
—— genkwanin 4'-O-α-L-(arabinopyranosyl-(1->6)-β-D-galactopyranoside) —— C27H30O14
genkwanin 4'-O-α-L-(arabinopyranosyl-(1->6)-β-D-galactopyranoside)
—— rutin —— C27H32O16
rutin
—— isorhamnetin-3-O-α-L-arabinoside-7-O-β-D-glucoside —— C27H30O16
isorhamnetin-3-O-α-L-arabinoside-7-O-β-D-glucoside
—— myricetin 3-O-α-L-(6''-galloylarabinofuranoside) —— C27H22O16
myricetin 3-O-α-L-(6''-galloylarabinofuranoside)
—— myricetin 3-O-α-L-(2''-galloylarabinofuranoside) —— C27H22O16
myricetin 3-O-α-L-(2''-galloylarabinofuranoside)
—— 3-(4-(4-(4-fluorobenzoyl)piperazine-1-yl)butoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromene-4-one —— C35H39FN2O9
3-(4-(4-(4-fluorobenzoyl)piperazine-1-yl)butoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromene-4-one