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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-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one —— C23H24O11
5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-3-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— (2S,3S,4R,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C23H25O12+
(2S,3S,4R,5S,6S)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— N-[(E)-[2-(4-methoxyphenyl)-7-methylchromen-4-ylidene]amino]-1H-benzimidazol-2-amine —— C24H20N4O2
N-[(E)-[2-(4-methoxyphenyl)-7-methylchromen-4-ylidene]amino]-1H-benzimidazol-2-amine
—— (2R,3E)-3-[(2-nitrophenyl)methylidene]-2-phenylchromen-4-one —— C22H15NO4
(2R,3E)-3-[(2-nitrophenyl)methylidene]-2-phenylchromen-4-one
—— (3aR,4R,9bR)-4-(4-methoxyphenyl)-2-methyl-3a-nitro-4,9b-dihydro-1H-chromeno[4,3-d][1,2]oxazole —— C18H18N2O5
(3aR,4R,9bR)-4-(4-methoxyphenyl)-2-methyl-3a-nitro-4,9b-dihydro-1H-chromeno[4,3-d][1,2]oxazole
—— (2R)-7-hydroxy-2-phenyl-5-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one —— C21H22O9
(2R)-7-hydroxy-2-phenyl-5-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
—— 7-[(2R,3R,4R,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one —— C27H30O14
7-[(2R,3R,4R,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— [(2S,3S,4R,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate —— C30H26O14
[(2S,3S,4R,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
—— 4-methyl-2-[(2Z)-2-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydrazinyl]-1H-pyrimidin-6-one —— C20H18N4O2
4-methyl-2-[(2Z)-2-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydrazinyl]-1H-pyrimidin-6-one
—— N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-2-(trifluoromethyl)aniline —— C22H17F3N2O
N-[(E)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-2-(trifluoromethyl)aniline
—— [(2'R,6R)-4,4-dimethyl-2'-phenyl-2-sulfanylidenespiro[1,3-diazinane-6,4'-2,3-dihydrochromene]-7'-yl] 2-nitrobenzenesulfonate —— C26H25N3O6S2
[(2'R,6R)-4,4-dimethyl-2'-phenyl-2-sulfanylidenespiro[1,3-diazinane-6,4'-2,3-dihydrochromene]-7'-yl] 2-nitrobenzenesulfonate
—— (5Z)-3-(oxolan-2-ylmethyl)-5-[(2-phenyl-2H-chromen-3-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C24H21NO3S2
(5Z)-3-(oxolan-2-ylmethyl)-5-[(2-phenyl-2H-chromen-3-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (9R,11S)-9-(3-bromo-4-methoxyphenyl)-11-(2,4-dichlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C25H17BrCl2N4O2
(9R,11S)-9-(3-bromo-4-methoxyphenyl)-11-(2,4-dichlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (9R,11R)-9-(3-bromo-4-methoxyphenyl)-11-(2,4-dichlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C25H17BrCl2N4O2
(9R,11R)-9-(3-bromo-4-methoxyphenyl)-11-(2,4-dichlorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (9S,11S)-9-(3-bromo-4-methoxyphenyl)-11-(3,4-dimethoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C27H23BrN4O4
(9S,11S)-9-(3-bromo-4-methoxyphenyl)-11-(3,4-dimethoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (9R,11R)-11-(4-chlorophenyl)-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 —— C25H19ClN4O2
(9R,11R)-11-(4-chlorophenyl)-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
—— (9R,11R)-9-(4-bromophenyl)-11-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C25H19BrN4O2
(9R,11R)-9-(4-bromophenyl)-11-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— methyl 4-[(9R,11R)-11-(3-bromo-4-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaen-9-yl]benzoate —— C27H21BrN4O4
methyl 4-[(9R,11R)-11-(3-bromo-4-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaen-9-yl]benzoate
—— (9R,11R)-9-(3-chlorophenyl)-4-methyl-11-phenyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C25H19ClN4O
(9R,11R)-9-(3-chlorophenyl)-4-methyl-11-phenyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— (9R,11R)-9-(4-ethylphenyl)-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C27H24N4O
(9R,11R)-9-(4-ethylphenyl)-11-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (9R,11S)-4-chloro-11-(2-fluorophenyl)-9-(3-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C24H15ClF2N4O
(9R,11S)-4-chloro-11-(2-fluorophenyl)-9-(3-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (2R)-7,8-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one —— C17H16O4
(2R)-7,8-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
—— (9R,11R)-11-(3-bromo-4-methoxyphenyl)-9-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C26H21BrN4O3
(9R,11R)-11-(3-bromo-4-methoxyphenyl)-9-(3-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (9R,11S)-4-chloro-9-(3-chlorophenyl)-11-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene —— C24H15Cl2FN4O
(9R,11S)-4-chloro-9-(3-chlorophenyl)-11-(2-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,13,15-hexaene
—— (2R)-2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-2,3-dihydrochromen-4-one —— C19H20O7
(2R)-2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-2,3-dihydrochromen-4-one
—— (S)-6-bromo-3-nitro-2-phenyl-2H-chromene —— C15H10BrNO3
(S)-6-bromo-3-nitro-2-phenyl-2H-chromene
—— 9,11-bis(4-methoxyphenyl)-14-methyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C27H24N4O3
9,11-bis(4-methoxyphenyl)-14-methyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 4-chloro-9,11-bis(2-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C26H21ClN4O3
4-chloro-9,11-bis(2-methoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 9-(4-ethylphenyl)-11-(4-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C26H21FN4O
9-(4-ethylphenyl)-11-(4-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 6-Amino-2-(2-chlorophenyl)-5-hydroxychromen-4-one —— C15H10ClNO3
6-Amino-2-(2-chlorophenyl)-5-hydroxychromen-4-one
—— 11-(2-fluorophenyl)-9-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C26H21FN4OS
11-(2-fluorophenyl)-9-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 3,5-dichloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]-2-hydroxybenzenesulfonamide —— C21H12Cl3NO6S
3,5-dichloro-N-[2-(2-chlorophenyl)-5-hydroxy-4-oxo-4H-chromen-8-yl]-2-hydroxybenzenesulfonamide
—— 4-chloro-11-(2-fluorophenyl)-9-(4-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C24H15ClF2N4O
4-chloro-11-(2-fluorophenyl)-9-(4-fluorophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 11-(3-bromo-4-methoxyphenyl)-9-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C26H21BrN4O2
11-(3-bromo-4-methoxyphenyl)-9-(4-methylphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-4-methylbenzamide —— C23H16ClNO4
N-[2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-8-yl]-4-methylbenzamide
—— 8-(4-Fluorophenyl)-5-methoxy-2-phenylchromen-4-one —— C22H15FO3
8-(4-Fluorophenyl)-5-methoxy-2-phenylchromen-4-one
—— 2-(2-Chlorophenyl)-5-ethoxychromen-4-one —— C17H13ClO3
2-(2-Chlorophenyl)-5-ethoxychromen-4-one
—— [2-(2-Chlorophenyl)-8-[(2,6-dichlorobenzoyl)amino]-5-hydroxy-4-oxochromen-7-yl] 2,6-dichlorobenzoate —— C29H14Cl5NO6
[2-(2-Chlorophenyl)-8-[(2,6-dichlorobenzoyl)amino]-5-hydroxy-4-oxochromen-7-yl] 2,6-dichlorobenzoate
—— 9-(2,4-dimethoxyphenyl)-4-methyl-11-pyridin-3-yl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C26H23N5O3
9-(2,4-dimethoxyphenyl)-4-methyl-11-pyridin-3-yl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 4-(4-chloro-11-phenyl-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)-N,N-dimethylaniline —— C26H22ClN5O
4-(4-chloro-11-phenyl-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)-N,N-dimethylaniline
—— 4-chloro-11-(4-methylphenyl)-14-methylsulfanyl-9-phenyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C26H21ClN4OS
4-chloro-11-(4-methylphenyl)-14-methylsulfanyl-9-phenyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— N-[(2R,4S)-2-phenyl-3,4-dihydro-2H-chromen-4-yl]benzamide —— C22H19NO2
N-[(2R,4S)-2-phenyl-3,4-dihydro-2H-chromen-4-yl]benzamide
—— N-[(2R,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl]methanesulfonamide —— C16H15NO4S
N-[(2R,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl]methanesulfonamide
—— 2-[(2S,4R)-2-phenyl-3,4-dihydro-2H-chromen-4-yl]isoindole-1,3-dione —— C23H17NO3
2-[(2S,4R)-2-phenyl-3,4-dihydro-2H-chromen-4-yl]isoindole-1,3-dione
—— N-[(2S,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl]methanesulfonamide —— C16H15NO4S
N-[(2S,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl]methanesulfonamide
—— (2S,3S)-3-hydroxy-2,3,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one —— C19H20O7
(2S,3S)-3-hydroxy-2,3,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
—— (2R,3S)-3-hydroxy-2,3-dimethoxy-2-(4-methylphenyl)chromen-4-one —— C18H18O5
(2R,3S)-3-hydroxy-2,3-dimethoxy-2-(4-methylphenyl)chromen-4-one
—— (2R,3S)-3-hydroxy-2,3,7-trimethoxy-2-phenylchromen-4-one —— C18H18O6
(2R,3S)-3-hydroxy-2,3,7-trimethoxy-2-phenylchromen-4-one
—— (2R,3S)-2,3-diethoxy-3-hydroxy-2-phenylchromen-4-one —— C19H20O5
(2R,3S)-2,3-diethoxy-3-hydroxy-2-phenylchromen-4-one
—— (2S,3S)-3-hydroxy-2,3,7-trimethoxy-2-phenylchromen-4-one —— C18H18O6
(2S,3S)-3-hydroxy-2,3,7-trimethoxy-2-phenylchromen-4-one