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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
—— 5-(N-Acetyl)amino-2-{4-[N-acetyl-N-(2-methoxyethyl)]amino}phenyl-4H-benzopyran-4-one 130599-89-2 C22H22N2O5
5-(N-Acetyl)amino-2-{4-[N-acetyl-N-(2-methoxyethyl)]amino}phenyl-4H-benzopyran-4-one
—— 2-[2-(2,6-difluorophenyl)chroman-6-yloxy]-5-nitropyridine 728934-53-0 C20H14F2N2O4
2-[2-(2,6-difluorophenyl)chroman-6-yloxy]-5-nitropyridine
—— 6,8-Dichloro-3-methyl-2-phenyl-3-pyrrolidin-1-ylmethyl-chroman-4-one 90486-54-7 C21H21Cl2NO2
6,8-Dichloro-3-methyl-2-phenyl-3-pyrrolidin-1-ylmethyl-chroman-4-one
—— 2-(1,3-benzodioxol-5-yl)-8-bromo-3-methoxy-6-methyl-4H-chromen-4-one 934374-16-0 C18H13BrO5
2-(1,3-benzodioxol-5-yl)-8-bromo-3-methoxy-6-methyl-4H-chromen-4-one
—— 3-[4-methoxy-7-(4-methoxyphenyl)-5-oxo-5H-furo[3,2-g]chromen-9-yl]acrylaldehyde 1616883-64-7 C22H16O6
3-[4-methoxy-7-(4-methoxyphenyl)-5-oxo-5H-furo[3,2-g]chromen-9-yl]acrylaldehyde
—— 7-Methoxy-3,3',4',5-tetraacetoxyflavanon 100595-94-6 C24H22O11
7-Methoxy-3,3',4',5-tetraacetoxyflavanon
—— 3-benzyloxy-3-bromo-2,4'-dimethoxyflavan-4-one 88187-13-7 C24H21BrO5
3-benzyloxy-3-bromo-2,4'-dimethoxyflavan-4-one
—— (2R,6S)-5-methylene-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[b]oxocine 1616761-37-5 C19H16O
(2R,6S)-5-methylene-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[b]oxocine
—— 6-chloro-2-(3-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-4-yl)-7-methyl-4H-chromen-4-one 1253513-73-3 C25H15Cl2FN2O2
6-chloro-2-(3-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-4-yl)-7-methyl-4H-chromen-4-one
—— 5-(2-cyclohexen-1-yl)-2,5-dihydro-9,10-dimethoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline 239067-99-3 C27H31NO3
5-(2-cyclohexen-1-yl)-2,5-dihydro-9,10-dimethoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline
—— 3.6-Dimethyl-flavon-carbonsaeure-(8)-<2-piperidino-ethylester> 95822-25-6 C25H27NO4
3.6-Dimethyl-flavon-carbonsaeure-(8)-<2-piperidino-ethylester>
—— (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-6-yl>-3',4',7-trimethoxyflavan 88269-40-3 C41H44O13
(2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-6-yl>-3',4',7-trimethoxyflavan
—— 7-benzyloxy-6-n-pentyloxy flavanone 203191-60-0 C27H28O4
7-benzyloxy-6-n-pentyloxy flavanone
—— jeediflavanone heptaacetate 90332-26-6 C44H36O18
jeediflavanone heptaacetate
—— Sakuranetin 5-O-β-D-xylopyranoside 128502-83-0 C21H22O9
Sakuranetin 5-O-β-D-xylopyranoside
—— 103215-53-8 C114H122O36
—— 2'-chloro-5-hydroxy-7-methoxyflavanone 1042741-39-8 C16H13ClO4
2'-chloro-5-hydroxy-7-methoxyflavanone
—— 5-amino-3,3-di(4'-fluorophenyl)naphtho[2,1-b]pyrane 859850-01-4 C25H17F2NO
5-amino-3,3-di(4'-fluorophenyl)naphtho[2,1-b]pyrane
—— 3,7,3'-triacetoxy epicatechin 1071725-97-7 C21H20O9
3,7,3'-triacetoxy epicatechin
—— lucenin I 35927-39-0 C26H28O15
lucenin I
—— penta-O-acetyl-(-)-epicatechin-(4β,2)-tri-O-acetylphloroglucinol 874999-30-1 C37H34O17
penta-O-acetyl-(-)-epicatechin-(4β,2)-tri-O-acetylphloroglucinol
—— 4-((2R,3S,4R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol 1242246-47-4 C49H42O8
4-((2R,3S,4R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol
—— 6,7-Methylendioxy-flavan 63194-71-8 C16H14O3
6,7-Methylendioxy-flavan
—— 5,7-dihydroxy-3',4'-dimethoxy-6-n-pentyloxy flavone 203190-91-4 C22H24O7
5,7-dihydroxy-3',4'-dimethoxy-6-n-pentyloxy flavone
—— 5-((2S,3R)-3-hydroxy-5,7-bis(2-nitrophenylsulfonyloxy)chroman-2-yl)benzene-1,2,3-triyl tris(2-nitrobenzenesulfonate) 1186527-23-0 C45H29N5O27S5
5-((2S,3R)-3-hydroxy-5,7-bis(2-nitrophenylsulfonyloxy)chroman-2-yl)benzene-1,2,3-triyl tris(2-nitrobenzenesulfonate)
—— 1343513-58-5 C16H9BrClNO4
—— 4-(4-Methylphenyl)-4-(4-phenoxyphenyl)-3-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),5,8,10,12,15,17,19-nonaene 1194840-23-7 C40H30O2
4-(4-Methylphenyl)-4-(4-phenoxyphenyl)-3-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),5,8,10,12,15,17,19-nonaene
—— 6-chloro-3-hydroxy-2-phenyl-pyrano[3,2-h]quinolin-4-one 21357-31-3 C18H10ClNO3
6-chloro-3-hydroxy-2-phenyl-pyrano[3,2-h]quinolin-4-one
—— 2-(2,5-diacetoxy-phenyl)-7-methoxy-chromen-4-one 109805-37-0 C20H16O7
2-(2,5-diacetoxy-phenyl)-7-methoxy-chromen-4-one
—— Acetic acid 2,3-dimethoxy-5-(3,5,6,7,8-pentamethoxy-4-oxo-4H-chromen-2-yl)-phenyl ester 82669-02-1 C24H26O11
Acetic acid 2,3-dimethoxy-5-(3,5,6,7,8-pentamethoxy-4-oxo-4H-chromen-2-yl)-phenyl ester
—— 1453812-76-4 C15H9FO3
—— 6-Hydroxymethyl-5,7-dimethoxy-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one 101395-10-2 C20H20O6
6-Hydroxymethyl-5,7-dimethoxy-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one
—— 3-Dimethylaminomethyl-2-p-tolyl-chroman-4-one; hydrochloride 77038-28-9 C19H21NO2*ClH
3-Dimethylaminomethyl-2-p-tolyl-chroman-4-one; hydrochloride
—— 240487-88-1 C37H38O12
—— 5S-[3-(2-piperidin-1-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol 1157856-84-2 C30H31NO5
5S-[3-(2-piperidin-1-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol
—— 5-benzyloxy-7-carboxymethyloxy-3',4'-dimethoxy flavone 203191-31-5 C26H22O8
5-benzyloxy-7-carboxymethyloxy-3',4'-dimethoxy flavone
—— 5-fluoro-3-(3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol 1352307-83-5 C30H32FNO4
5-fluoro-3-(3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol
—— 5-Amino-2-[4-bis(2-hydroxyethyl)amino]phenyl-4H-benzopyran-4-one 130599-63-2 C19H20N2O4
5-Amino-2-[4-bis(2-hydroxyethyl)amino]phenyl-4H-benzopyran-4-one
—— 3,4'-dihydroxyflavylium chloride 15402-05-8 C15H11O3*Cl
3,4'-dihydroxyflavylium chloride
—— (2S,1'R)-4-chloro-2-(4'-chlorophenyl)-3-(1'-hydroxypropyl)-2H-chromene 1440429-59-3 C18H16Cl2O2
(2S,1'R)-4-chloro-2-(4'-chlorophenyl)-3-(1'-hydroxypropyl)-2H-chromene
—— Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-b-D-glucopyranoside 185027-87-6 C43H49O23+
Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-b-D-glucopyranoside
—— 8-chloro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 1441771-97-6 C18H15ClO6
8-chloro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
—— 1204484-92-3 C64H58N4O8
—— 2-phenyl-2H-chromene-6-carbonitrile 1384984-04-6 C16H11NO
2-phenyl-2H-chromene-6-carbonitrile
—— 3-(4-bromophenyl)sulfonyl-6-methyl-2-(4-nitrophenyl)chromen-4-one 87127-96-6 C22H14BrNO6S
3-(4-bromophenyl)sulfonyl-6-methyl-2-(4-nitrophenyl)chromen-4-one
—— 2-(4-Chloro-phenyl)-3,6-dinitro-chromen-4-one 143468-30-8 C15H7ClN2O6
2-(4-Chloro-phenyl)-3,6-dinitro-chromen-4-one
—— 4'-acetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan 1253227-74-5 C31H34O14
4'-acetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5,7-dihydroxyflavan
—— 2-(1,3-benzodioxol-5-yl)-3-methoxy-6-methyl-8-(1-piperidinyl)-4H-chromen-4-one 934374-18-2 C23H23NO5
2-(1,3-benzodioxol-5-yl)-3-methoxy-6-methyl-8-(1-piperidinyl)-4H-chromen-4-one
—— 4'-Hydroxy-7-methoxy-flavylium 46992-91-0 C16H13O3
4'-Hydroxy-7-methoxy-flavylium
—— 5R-(+)-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-8-ol 554431-43-5 C27H27NO4
5R-(+)-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-8-ol