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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
—— (3R,4S,5S,6R)-2-[[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-yl]peroxy]-6-(hydroxymethyl)oxane-3,4,5-triol —— C21H22O11
(3R,4S,5S,6R)-2-[[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-yl]peroxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— 11-(3-bromo-4-methoxyphenyl)-9-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C25H18BrFN4O2
11-(3-bromo-4-methoxyphenyl)-9-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 11-(2,4-dichlorophenyl)-9-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C25H18Cl2N4O2
11-(2,4-dichlorophenyl)-9-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 7-Hydroxy-3-methyl-2-(2-methyl-2-oxo-1,3,2lambda5-benzodioxaphosphol-5-yl)chromen-4-one —— C17H13O6P
7-Hydroxy-3-methyl-2-(2-methyl-2-oxo-1,3,2lambda5-benzodioxaphosphol-5-yl)chromen-4-one
—— 9-(2,3-dimethoxyphenyl)-11-(4-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C27H24N4O4
9-(2,3-dimethoxyphenyl)-11-(4-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— (2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxy-2,3-dihydrochromen-4-one —— C21H22O13
(2S)-2-(3,5-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]peroxy-2,3-dihydrochromen-4-one
—— 2-(4-Methylphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one —— C26H17F3N2O4
2-(4-Methylphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one
—— 4-(2-methylphenyl)-2-phenyl-3,4-dihydro-2H-chromene —— C22H20O
4-(2-methylphenyl)-2-phenyl-3,4-dihydro-2H-chromene
—— (2R,3S)-2-(3,4-dihydroxyphenyl)-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-3,4-dihydro-2H-chromene-3,5,7-triol —— C21H24O11
(2R,3S)-2-(3,4-dihydroxyphenyl)-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2,3-Dimethyl-6'-phenoxy-2'-phenylspiro[1,2,4-oxadiazole-5,4'-2,3-dihydrochromene] —— C24H22N2O3
2,3-Dimethyl-6'-phenoxy-2'-phenylspiro[1,2,4-oxadiazole-5,4'-2,3-dihydrochromene]
—— 4-[[2-(4-Methoxyphenyl)-6-methylchromen-4-ylidene]methyl]-1-methylpyridin-1-ium —— C24H22NO2+
4-[[2-(4-Methoxyphenyl)-6-methylchromen-4-ylidene]methyl]-1-methylpyridin-1-ium
—— methyl 4-(4-methyl-11-thiophen-2-yl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaen-9-yl)benzoate —— C25H20N4O3S
methyl 4-(4-methyl-11-thiophen-2-yl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaen-9-yl)benzoate
—— 2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylic acid —— C22H20O10
2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylic acid
—— 2-(3,4-Dimethoxyphenyl)-5,7-dimethyl-3-(1-oxo-1-phenylpropan-2-yl)oxychromen-4-one —— C28H26O6
2-(3,4-Dimethoxyphenyl)-5,7-dimethyl-3-(1-oxo-1-phenylpropan-2-yl)oxychromen-4-one
—— 2-(2-Chloro-3-fluorophenyl)-8-[[hydroxy(pyrazin-2-yl)methyl]amino]chromen-4-one —— C20H13ClFN3O3
2-(2-Chloro-3-fluorophenyl)-8-[[hydroxy(pyrazin-2-yl)methyl]amino]chromen-4-one
—— 4-(2,2-difluoro-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-4-yl)phenol —— C18H16F2O2
4-(2,2-difluoro-3,3a,4,9b-tetrahydro-1H-cyclopenta[c]chromen-4-yl)phenol
—— 2-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene —— C17H15BrO3
2-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene
—— 1,1-Dichloro-7a-methyl-7-(2-methylphenyl)-1a-phenyl-1,1a,7,7a-tetrahydrocyclopropa[b]chromene —— C24H20Cl2O
1,1-Dichloro-7a-methyl-7-(2-methylphenyl)-1a-phenyl-1,1a,7,7a-tetrahydrocyclopropa[b]chromene
—— (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl)phenoxy]oxane-2-carboxylic acid —— C21H22O12
(2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl)phenoxy]oxane-2-carboxylic acid
—— [6-Bromo-2-(4-methoxyphenyl)chromen-4-ylidene]-(4-pyrrolidin-1-ylphenyl)azanium —— C26H24BrN2O2+
[6-Bromo-2-(4-methoxyphenyl)chromen-4-ylidene]-(4-pyrrolidin-1-ylphenyl)azanium
—— N-cyclohexyl-4,4-bis[4-(diethylamino)-2,5-dimethoxyphenyl]-N-ethylchromeno[4,3-d][1,3]thiazol-2-amine;4-[4-[4-(dimethylamino)-2-methoxyphenyl]-2,8-dimethylchromeno[4,3-d][1,3]thiazol-4-yl]-3-methoxy-N,N-dimethylaniline;4-[9-[4-(dimethylamino)phenyl]-4-methyl-8-oxa-16,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(17),2(7),3,5,10,12,14-heptaen-9-yl]-N,N-dimethylaniline;4-[4-[4-(dimethylamino)phenyl]-2-morpholin-4-ylchromeno[4,3-d][1,3]thiazol-4-yl]-N,N-dimethylaniline —— C133H151N15O11S3
N-cyclohexyl-4,4-bis[4-(diethylamino)-2,5-dimethoxyphenyl]-N-ethylchromeno[4,3-d][1,3]thiazol-2-amine;4-[4-[4-(dimethylamino)-2-methoxyphenyl]-2,8-dimethylchromeno[4,3-d][1,3]thiazol-4-yl]-3-methoxy-N,N-dimethylaniline;4-[9-[4-(dimethylamino)phenyl]-4-methyl-8-oxa-16,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(17),2(7),3,5,10,12,14-heptaen-9-yl]-N,N-dimethylaniline;4-[4-[4-(dimethylamino)phenyl]-2-morpholin-4-ylchromeno[4,3-d][1,3]thiazol-4-yl]-N,N-dimethylaniline
—— N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridine-2-carboxamide —— C21H17N3O2
N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]pyridine-2-carboxamide
—— 2-(3,4-Dihydroxyphenyl)-6-[(2,2-dimethyl-6-methylidenecyclohexyl)methyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C25H28O6
2-(3,4-Dihydroxyphenyl)-6-[(2,2-dimethyl-6-methylidenecyclohexyl)methyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— [2-(3,4-Dihydroxyphenyl)-2,3,4,4-tetra(hexanoyl)-5,7-dihydroxychromen-3-yl] hexanoate —— C45H64O11
[2-(3,4-Dihydroxyphenyl)-2,3,4,4-tetra(hexanoyl)-5,7-dihydroxychromen-3-yl] hexanoate
—— [2-(4-Methoxyphenyl)-6-methylchromen-4-ylidene]-phenylazanium —— C23H20NO2+
[2-(4-Methoxyphenyl)-6-methylchromen-4-ylidene]-phenylazanium
—— 1-O-benzyl 6-O-(4-oxo-2-phenyl-5-phenylmethoxychromen-3-yl) hexanedioate —— C35H30O7
1-O-benzyl 6-O-(4-oxo-2-phenyl-5-phenylmethoxychromen-3-yl) hexanedioate
—— 6-[7-Hydroxy-3,3,5,8-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-4-yl]-3,3,4,5,8-pentamethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-7-ol;8-[7-hydroxy-3,3,5,8-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-4-yl]-3,3,4,5-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-7-ol —— C89H110O8
6-[7-Hydroxy-3,3,5,8-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-4-yl]-3,3,4,5,8-pentamethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-7-ol;8-[7-hydroxy-3,3,5,8-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-4-yl]-3,3,4,5-tetramethyl-2-(3,4,5-trimethylphenyl)-2,4-dihydrochromen-7-ol
—— (6,7-Dimethyl-4-oxo-2-phenylchromen-3-yl) 1-(4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylate —— C29H25NO6
(6,7-Dimethyl-4-oxo-2-phenylchromen-3-yl) 1-(4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylate
—— [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] octadec-9-enoate —— C33H46O7
[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] octadec-9-enoate
—— Ethane;3-methyl-2-phenyl-2,3-dihydrochromen-4-one —— C20H26O2
Ethane;3-methyl-2-phenyl-2,3-dihydrochromen-4-one
—— 2-[2-(4-Tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoic acid —— C23H24O5
2-[2-(4-Tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoic acid
—— Ethyl 2-[2-(4-tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate —— C25H28O5
Ethyl 2-[2-(4-tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate
—— 2-[2-(4-Tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate —— C23H23O5-
2-[2-(4-Tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate
—— Methyl 2-[2-(4-tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate —— C24H26O5
Methyl 2-[2-(4-tert-butylphenyl)-6-methyl-4-oxochromen-3-yl]oxypropanoate
—— (11S)-11-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-ol —— C29H29NO4
(11S)-11-[4-(2-piperidin-1-ylethoxy)phenyl]-5,11-dihydrochromeno[4,3-c]chromen-2-ol
—— 6-Methoxy-2-(2,3,4,5-tetrahydro-1,6-benzodioxocin-8-yl)chromen-4-one —— C20H18O5
6-Methoxy-2-(2,3,4,5-tetrahydro-1,6-benzodioxocin-8-yl)chromen-4-one
—— 3-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C25H26O13
3-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxymethyl]oxan-2-yl]oxychromen-4-one —— C28H32O16
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxymethyl]oxan-2-yl]oxychromen-4-one
—— 2-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2H-chromene —— C16H13F3O
2-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2H-chromene
—— 2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-3-phosphanyloxychromen-4-one —— C15H11O7P
2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-3-phosphanyloxychromen-4-one
—— 2,4-dimethyl-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzamide —— C24H22N2O2
2,4-dimethyl-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzamide
—— 2-azido-N-{6-[2-(4-fluorophenyl)chroman-6-yloxy]pyridin-3-yl}-acetamide 728936-58-1 C22H18FN5O3
2-azido-N-{6-[2-(4-fluorophenyl)chroman-6-yloxy]pyridin-3-yl}-acetamide
—— 6-(2-hydroxy-2-methylbutyl)-2'-(7-hydroxy-3,7-dimethyloct-2-enyl)-3',4',5,7-tetramethoxyflavanone —— C34H48O8
6-(2-hydroxy-2-methylbutyl)-2'-(7-hydroxy-3,7-dimethyloct-2-enyl)-3',4',5,7-tetramethoxyflavanone
—— 2-(3,4-dihydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one —— C21H20O10
2-(3,4-dihydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
—— 2-(3,4-dihydroxyphenyl)-3-[(2S,4S,5S)-3,4-dihydroxy-5-[(2R,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxychromen-4-one —— C33H40O21
2-(3,4-dihydroxyphenyl)-3-[(2S,4S,5S)-3,4-dihydroxy-5-[(2R,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxychromen-4-one
—— (2s)-7,2'-Dihydroxy-5-methoxyflavanone —— C16H14O5
(2s)-7,2'-Dihydroxy-5-methoxyflavanone
—— (2S)-2-(3,4-dihydroxyphenyl)-4,5,7-trihydroxy-4H-chromen-3-one —— C15H12O7
(2S)-2-(3,4-dihydroxyphenyl)-4,5,7-trihydroxy-4H-chromen-3-one
—— 9-(2,4-dimethoxyphenyl)-11-(4-propan-2-ylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C29H28N4O3
9-(2,4-dimethoxyphenyl)-11-(4-propan-2-ylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R,3R,4S,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)oxan-4-yl]chromen-4-one —— C21H20O11
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R,3R,4S,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)oxan-4-yl]chromen-4-one
—— 3-Ethoxy-2-(3-hydroxy-4-methylphenyl)-2,3-dihydrochromen-4-one —— C18H18O4
3-Ethoxy-2-(3-hydroxy-4-methylphenyl)-2,3-dihydrochromen-4-one