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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-hydroxy-2-(4-hydroxyphenyl)-6-(methylamino)-4-oxo-4H-chromen-8-yl]-1λ6-isothiazolidin-1,1-dione 372103-16-7 C19H18N2O6S
2-[3-hydroxy-2-(4-hydroxyphenyl)-6-(methylamino)-4-oxo-4H-chromen-8-yl]-1λ6-isothiazolidin-1,1-dione
—— 4H-1-Benzopyran-4-one, 8-bromo-2-(4-methoxyphenyl)-6-methyl-,oxime 140885-81-0 C17H14BrNO3
4H-1-Benzopyran-4-one, 8-bromo-2-(4-methoxyphenyl)-6-methyl-,oxime
—— 4-(aminomethyl)-2-(4-methoxyphenyl)-2-methyl-3,4-dihydro-2H-chromen-4-ol 1313611-43-6 C18H21NO3
4-(aminomethyl)-2-(4-methoxyphenyl)-2-methyl-3,4-dihydro-2H-chromen-4-ol
—— 1262589-81-0 C46H40F2N4O3
—— 3'-nitro-3,5,6,7,8,4'-hexamethoxy-flavone 1266729-11-6 C21H21NO10
3'-nitro-3,5,6,7,8,4'-hexamethoxy-flavone
—— 3',5'-diiodo-calycopterin 1266729-15-0 C19H16I2O8
3',5'-diiodo-calycopterin
—— 2-amino-8-ethoxycarbonyl-5-oxo-4-phenyl-6-(2,4,6-tribromophenyl)-4H-pyrano[2,3-d]pyridazine-3-carboxylic acid 126837-75-0 C23H16Br3N3O6
2-amino-8-ethoxycarbonyl-5-oxo-4-phenyl-6-(2,4,6-tribromophenyl)-4H-pyrano[2,3-d]pyridazine-3-carboxylic acid
—— 8-acetylamino-6-methyl-2-(3-nitro-phenyl)-chroman-4-one 101732-25-6 C18H16N2O5
8-acetylamino-6-methyl-2-(3-nitro-phenyl)-chroman-4-one
—— 7-[3-(4-benzyl-piperazin-1-yl)-propoxy]-2-phenyl-chromen-4-one 39576-87-9 C29H30N2O3
7-[3-(4-benzyl-piperazin-1-yl)-propoxy]-2-phenyl-chromen-4-one
—— 6-acetyl-5,7-dihydroxy-3',4',5'-trimethoxyflavone 84212-53-3 C20H18O8
6-acetyl-5,7-dihydroxy-3',4',5'-trimethoxyflavone
—— 7-Methoxy-4'-<2-piperidino-ethoxy>-flavon 95441-67-1 C23H25NO4
7-Methoxy-4'-<2-piperidino-ethoxy>-flavon
—— (<i>S</i>)-7-acetoxy-2-phenyl-5-(tetra-<i>O</i>-acetyl-ξ-D-glucopyranosyloxy)-chroman-4-one 122472-94-0 C31H32O14
(<i>S</i>)-7-acetoxy-2-phenyl-5-(tetra-<i>O</i>-acetyl-ξ-D-glucopyranosyloxy)-chroman-4-one
—— 7-(3-methylbut-2-enyloxy)-8-acetyl-3-methylflavone 329913-59-9 C23H22O4
7-(3-methylbut-2-enyloxy)-8-acetyl-3-methylflavone
—— 5-allyloxy-3',4'-methylenedioxy-7-tosyloxyflavone 79339-32-5 C26H20O8S
5-allyloxy-3',4'-methylenedioxy-7-tosyloxyflavone
—— Selinondiacetat 39953-45-2 C24H24O7
Selinondiacetat
—— 7-O-(2-Oxobutyl)-3'-O-cyclopentyldiosmetin 205524-05-6 C25H26O7
7-O-(2-Oxobutyl)-3'-O-cyclopentyldiosmetin
—— 8-(D-Glucofuranosyl)-5,7,4'-trimethoxyflavanon 119529-75-8 C24H28O10
8-(D-Glucofuranosyl)-5,7,4'-trimethoxyflavanon
—— (-)-hydnocarpin-7-O-β-D-glucoside 1309133-19-4 C31H30O14
(-)-hydnocarpin-7-O-β-D-glucoside
—— (2RS,4R)-6',6'-difluoro-6-nitro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine 1415109-17-9 C19H17F2N3O4
(2RS,4R)-6',6'-difluoro-6-nitro-2-phenyl-6',7'-dihydro-2'H-spiro[chroman-4,5'-[1,4]oxazepin]-3'-amine
—— 6-Benzoyl-2'-methoxy-8-methyl-flavanon 95957-54-3 C24H20O4
6-Benzoyl-2'-methoxy-8-methyl-flavanon
—— 5,7,5',7'-tetramethoxy-2,2'-bis-(4-methoxy-phenyl)-2,3,2',3'-tetrahydro-[8,8']bichromenyl-4,4'-dione 66788-75-8 C36H34O10
5,7,5',7'-tetramethoxy-2,2'-bis-(4-methoxy-phenyl)-2,3,2',3'-tetrahydro-[8,8']bichromenyl-4,4'-dione
—— 4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone 943827-57-4 C53H54O22S
4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone
—— 1-phenyl-3-(4-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one 1089663-26-2 C21H22O7
1-phenyl-3-(4-(((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one
—— 3-(6-hydroxy-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-3-yl)benzonitrile hydrochloride 1443992-64-0 C31H32N2O3*ClH
3-(6-hydroxy-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-3-yl)benzonitrile hydrochloride
—— 1,28-bis[4-((5-hydroxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19,22,25,28-decaoxaoctacosane 916330-91-1 C52H62O20
1,28-bis[4-((5-hydroxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19,22,25,28-decaoxaoctacosane
—— 1391062-81-9 C27H22O11
—— 5,7-bis(benzyloxy)-2-(7-benzyloxy-2,2-dimethyl-6-chromanyl)-4-chromanone 96909-27-2 C41H38O6
5,7-bis(benzyloxy)-2-(7-benzyloxy-2,2-dimethyl-6-chromanyl)-4-chromanone
—— 2-(3,5-difluorophenyl)chroman-4,6-diol 488847-96-7 C15H12F2O3
2-(3,5-difluorophenyl)chroman-4,6-diol
—— 2-benzo[1,3]dioxol-5-yl-7-hydroxy-8-nitro-chromen-4-one 132752-66-0 C16H9NO7
2-benzo[1,3]dioxol-5-yl-7-hydroxy-8-nitro-chromen-4-one
—— 2-(2,3-dimethoxy-phenyl)-6,7,8-trimethoxy-chroman-4-one 111797-37-6 C20H22O7
2-(2,3-dimethoxy-phenyl)-6,7,8-trimethoxy-chroman-4-one
—— 6-bromo-7-methoxy-2-(4-methoxy-phenyl)-chroman-4-one 108979-12-0 C17H15BrO4
6-bromo-7-methoxy-2-(4-methoxy-phenyl)-chroman-4-one
—— 2-[(4-imidazol-1-yl)-phenyl]-3-benzyloxy-6-[(1-iminopropyl-3-methoxy)amino]-4H-1-benzopyran-4-one 1187016-38-1 C29H26N4O4
2-[(4-imidazol-1-yl)-phenyl]-3-benzyloxy-6-[(1-iminopropyl-3-methoxy)amino]-4H-1-benzopyran-4-one
—— 2-(3-fluoro-phenyl)-chroman-6-ol 488847-67-2 C15H13FO2
2-(3-fluoro-phenyl)-chroman-6-ol
—— 6-benzoyl-8-chloro-2-phenyl-chroman-4-one 102662-11-3 C22H15ClO3
6-benzoyl-8-chloro-2-phenyl-chroman-4-one
—— (+/-)-7-Methoxy-cis-3,4-diacetoxy-trans-2,3-flavan 94683-57-5 C20H20O6
(+/-)-7-Methoxy-cis-3,4-diacetoxy-trans-2,3-flavan
—— 6-benzoyl-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one 102665-02-1 C24H18O4
6-benzoyl-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one
—— 2-(2-fluorophenyl)chroman-4,6-diol 488848-34-6 C15H13FO3
2-(2-fluorophenyl)chroman-4,6-diol
—— 2-(4-β-D-glucopyranosyloxy-phenyl)-5-hydroxy-chromen-4-one 112046-90-9 C21H20O9
2-(4-β-D-glucopyranosyloxy-phenyl)-5-hydroxy-chromen-4-one
—— 4-Deuteroflavan 55539-54-3 C15H14O
4-Deuteroflavan
—— 6-chloro-3-methoxymethoxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran 1250865-51-0 C18H15ClO5
6-chloro-3-methoxymethoxy-2-(4'-methoxyphenyl)-4-oxo-4H-1-benzopyran
—— 3',4'-dimethoxy-6-methylflavone azine 101553-60-0 C36H32N2O6
3',4'-dimethoxy-6-methylflavone azine
—— 1-(2-{4-[2-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-piperidine 554431-59-3 C35H43NO4Si
1-(2-{4-[2-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-piperidine
—— 2',7-Diacetoxy-3-methylflavon 56595-68-7 C20H16O6
2',7-Diacetoxy-3-methylflavon
—— 1609067-47-1 C35H42N4O10
—— 4',7-di-O-benzylquercetin-3-O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-(1<*>2)-3,4-di-O-acetyl-β-D-xylopyranoside 159030-06-5 C52H52O22
4',7-di-O-benzylquercetin-3-O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-(1<*>2)-3,4-di-O-acetyl-β-D-xylopyranoside
—— isoquercitrin 2'',3'',6''-triacetate 959833-95-5 C27H26O15
isoquercitrin 2'',3'',6''-triacetate
—— 7-methoxy-4-methyl-2,4-diphenyl-4H-chromen-8-ol 1384833-40-2 C23H20O3
7-methoxy-4-methyl-2,4-diphenyl-4H-chromen-8-ol
—— 4-[(2S,3S)-2,3,7-Trimethoxy-2-(4-nitro-phenyl)-4-oxo-chroman-3-ylamino]-benzaldehyde 139936-72-4 C25H22N2O8
4-[(2S,3S)-2,3,7-Trimethoxy-2-(4-nitro-phenyl)-4-oxo-chroman-3-ylamino]-benzaldehyde
—— 2'-Dimethylamino-5'-nitroflavon 57476-52-5 C17H14N2O4
2'-Dimethylamino-5'-nitroflavon
—— 4-Methoxy-3-nitro-2-phenyl-2H-chromene 92856-28-5 C16H13NO4
4-Methoxy-3-nitro-2-phenyl-2H-chromene