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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-(3,4,5-tris(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one 1389320-67-5 C36H28O7
2-(3,4,5-tris(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one
—— [4,8]-2,3-trans-3,4-trans:2,3-trans-deca-O-acetyl-bi-(+)-catechin 21179-22-6 C50H46O22
[4,8]-2,3-trans-3,4-trans:2,3-trans-deca-O-acetyl-bi-(+)-catechin
—— 8-(p-hydroxybenzyl)-(+)-catechin 82246-02-4 C22H20O7
8-(p-hydroxybenzyl)-(+)-catechin
—— 1466397-28-3 C29H22O6
—— (5R)-5-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol 554431-52-6 C27H27NO5
(5R)-5-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol
—— Kaempferol-3-O-(6-O-β-D-glucopyranosyl)-β-D-galactopyranosid 73803-52-8 C27H30O16
Kaempferol-3-O-(6-O-β-D-glucopyranosyl)-β-D-galactopyranosid
—— 3-(Arabinopyranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium 324533-66-6 C20H19O10+
3-(Arabinopyranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium
—— (2R,3S)-6-hydroxy-5,7,3',4'-tetra-O-methylflavan-3-ol 69119-45-5 C19H22O7
(2R,3S)-6-hydroxy-5,7,3',4'-tetra-O-methylflavan-3-ol
—— 65597-49-1 C24H30O11
—— (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-7-(((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 1374991-36-2 C65H56O24
(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-7-(((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
—— 3(3-acetylaminobenzylidene)-flavanone 99111-33-8 C24H19NO3
3(3-acetylaminobenzylidene)-flavanone
—— (R)-2-(4-ethylphenyl)chroman-4-one 1438763-28-0 C17H16O2
(R)-2-(4-ethylphenyl)chroman-4-one
—— (2<i>R</i>)-5,7-Diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-3<i>t</i>-(3,4,5-tris-benzyloxy-benzoyloxy)-chroman 20728-96-5 C51H44O14
(2<i>R</i>)-5,7-Diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-3<i>t</i>-(3,4,5-tris-benzyloxy-benzoyloxy)-chroman
—— 6,8-bis(o-hydroxybenzyl)-(+)-catechin 82894-94-8 C29H26O8
6,8-bis(o-hydroxybenzyl)-(+)-catechin
—— 2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid 246181-58-8 C32H28O14
2,2-bis[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]acetic acid
—— 1403356-81-9 C17H15ClO3
—— (2R,3S)-2-(3,4-bis(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychromane-5,7-diyl bis(2-nitrobenzenesulfonate) 1186527-26-3 C39H26N4O22S4
(2R,3S)-2-(3,4-bis(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychromane-5,7-diyl bis(2-nitrobenzenesulfonate)
—— acetate of (+)-catechin 116935-88-7 C17H16O7
acetate of (+)-catechin
—— 4''-methyl-5''-phenylfuro<2'',3'':7,8>flavone 57309-10-1 C24H16O3
4''-methyl-5''-phenylfuro<2'',3'':7,8>flavone
—— 1508303-76-1 C17H10O4*C63H112O35
—— 8-bromomethyl-2-phenyl-4H-1-benzopyran-4-one 87165-52-4 C16H11BrO2
8-bromomethyl-2-phenyl-4H-1-benzopyran-4-one
—— 3-O-acetyl-6-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 69119-43-3 C21H23BrO7
3-O-acetyl-6-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
—— (2S,3R,4R,2'R,3'S)-2,2'-Bis-(3,4-dimethoxy-phenyl)-7,5',7'-trimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol 78185-23-6 C37H40O11
(2S,3R,4R,2'R,3'S)-2,2'-Bis-(3,4-dimethoxy-phenyl)-7,5',7'-trimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol
—— malvidin-3-glucoside-(O)-catechin 1399679-45-8 C38H38O18
malvidin-3-glucoside-(O)-catechin
—— Acetic acid (S)-2-(4-acetoxy-phenyl)-6-((E)-3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-4-oxo-chroman-7-yl ester 96917-33-8 C29H32O7
Acetic acid (S)-2-(4-acetoxy-phenyl)-6-((E)-3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-4-oxo-chroman-7-yl ester
—— N-((2R,3R)-5,7-Dimethoxy-4-oxo-2-phenyl-chroman-3-yl)-acetamide 37884-34-7 C19H19NO5
N-((2R,3R)-5,7-Dimethoxy-4-oxo-2-phenyl-chroman-3-yl)-acetamide
—— 3-[(Hexyl-methyl-amino)-methyl]-6-methyl-2-phenyl-chroman-4-one; hydriodide 34097-70-6 C24H31NO2*HI
3-[(Hexyl-methyl-amino)-methyl]-6-methyl-2-phenyl-chroman-4-one; hydriodide
—— ethyl 3-((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)propanoate 1312298-15-9 C20H22O8
ethyl 3-((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)propanoate
—— (2R)-2r-[3,4-bis-(toluene-4-sulfonyloxy)-phenyl]-3t,5,7-tris-(toluene-4-sulfonyloxy)-chroman 120036-98-8 C50H44O16S5
(2R)-2r-[3,4-bis-(toluene-4-sulfonyloxy)-phenyl]-3t,5,7-tris-(toluene-4-sulfonyloxy)-chroman
—— (2R)-2r-(3,4-dimethoxy-phenyl)-3c-methanesulfonyloxy-5,7-dimethoxy-chroman 102169-05-1 C20H24O8S
(2R)-2r-(3,4-dimethoxy-phenyl)-3c-methanesulfonyloxy-5,7-dimethoxy-chroman
—— 3,7-bisbenzyloxy-2-(3-hydroxy-4-methoxyphenyl)-5-hydroxychromen-4-one 498548-16-6 C30H24O7
3,7-bisbenzyloxy-2-(3-hydroxy-4-methoxyphenyl)-5-hydroxychromen-4-one
—— (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(allyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate 1374991-30-6 C54H54O14Si
(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(allyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate
—— (2R,3S)-2-(2,2-dihydroxy-2l4-benzo[d][1,3,2]dioxathiol-5-yl)-8-(hydroxy(4-hydroxy-3-methoxyphenyl)methyl)chromane-3,5,7-triol 1235292-23-5 C23H22O11S
(2R,3S)-2-(2,2-dihydroxy-2l4-benzo[d][1,3,2]dioxathiol-5-yl)-8-(hydroxy(4-hydroxy-3-methoxyphenyl)methyl)chromane-3,5,7-triol
—— 7-((3-chlorobenzyl)oxy)-2-(3,4-diacetoxyphenyl)-4-oxo-4H-chromene-3,5-diyl diacetate 1187652-48-7 C30H23ClO11
7-((3-chlorobenzyl)oxy)-2-(3,4-diacetoxyphenyl)-4-oxo-4H-chromene-3,5-diyl diacetate
—— 11-[4-(2-azepan-1-yl-ethoxy)-phenyl]-8-(2,2-dimethyl-propionyloxy)-11-methyl-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester 554431-09-3 C41H49NO7
11-[4-(2-azepan-1-yl-ethoxy)-phenyl]-8-(2,2-dimethyl-propionyloxy)-11-methyl-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester
—— 2-hydroxy-3,3-dimethoxyflavanone 76182-88-2 C17H16O5
2-hydroxy-3,3-dimethoxyflavanone
—— 5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-3-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4H-chromen-4-one 1443276-32-1 C26H28O7
5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-3-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4H-chromen-4-one
—— 8-methyl-2-phenyl-2H-chromene 67859-04-5 C16H14O
8-methyl-2-phenyl-2H-chromene
—— (2R,3S)-2,3-trans-3-acetoxy-5-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl>-3',4',7,8-tetramethoxyflavan 89444-62-2 C42H46O14
(2R,3S)-2,3-trans-3-acetoxy-5-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl>-3',4',7,8-tetramethoxyflavan
—— (2R,3S,11S,12R)-2,12-bis(3,4-dihydroxyphenyl)-14-(5-(hydroxymethyl)furan-2-yl)-3,4,11,12-tetrahydro-2H,10H,14H-dipyrano[2,3-a:3',2'-j]xanthene-3,5,9,11-tetraol 324011-53-2 C36H30O13
(2R,3S,11S,12R)-2,12-bis(3,4-dihydroxyphenyl)-14-(5-(hydroxymethyl)furan-2-yl)-3,4,11,12-tetrahydro-2H,10H,14H-dipyrano[2,3-a:3',2'-j]xanthene-3,5,9,11-tetraol
—— (2R,8R)-8-(4,5-dihydroxy-2-((2R)-3,5,7-trihydroxychroman-2-yl)phenyl)-2-((2R)-2-((2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-4,5-dihydroxyphenyl)chromane-3,5,7-triol 1193688-42-4 C45H38O18
(2R,8R)-8-(4,5-dihydroxy-2-((2R)-3,5,7-trihydroxychroman-2-yl)phenyl)-2-((2R)-2-((2R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-4,5-dihydroxyphenyl)chromane-3,5,7-triol
—— phenyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate 1607814-70-9 C22H14O4
phenyl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
—— 3-[(naphthalen-2-yl)carbonyl]-2-phenyl-4H-chromen-4-one 1415385-07-7 C26H16O3
3-[(naphthalen-2-yl)carbonyl]-2-phenyl-4H-chromen-4-one
—— 4-methylene-2-phenylchromane 42931-13-5 C16H14O
4-methylene-2-phenylchromane
—— (-)-robinetinidol-(4β,8)-(+)-catechin octa-O-methyl 78185-19-0 C38H42O12
(-)-robinetinidol-(4β,8)-(+)-catechin octa-O-methyl
—— (2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1r,4R)-4-((tert-butyldimethylsilyl)oxy)cyclohexane-1-carboxylate 1608504-15-9 C56H62O8Si
(2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1r,4R)-4-((tert-butyldimethylsilyl)oxy)cyclohexane-1-carboxylate
—— 8-(o-hydroxybenzyl)-(+)-catechin 82246-00-2 C22H20O7
8-(o-hydroxybenzyl)-(+)-catechin
—— 3'-O-(CO-Ala-Asp-OH)-quercetin 1138406-36-6 C23H20N2O13
3'-O-(CO-Ala-Asp-OH)-quercetin
—— apigenin 7-O-glucosyl(3'->6'')luteolin 7''-O-glucoside 1343452-88-9 C42H38O21
apigenin 7-O-glucosyl(3'->6'')luteolin 7''-O-glucoside
—— 2-[4-(4-chlorobutoxy)-phenyl]-7-(tetrahydropyran-2-yloxy)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-2,3-dihydro-4H-1-benzopyran-4-one 361391-09-5 C35H39ClO7
2-[4-(4-chlorobutoxy)-phenyl]-7-(tetrahydropyran-2-yloxy)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-2,3-dihydro-4H-1-benzopyran-4-one