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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
—— N-[1-(3,5-dimethylpyrazolidin-4-yl)ethyl]-2-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-1,3-thiazole-5-carboxamide —— C26H30N4O3S
N-[1-(3,5-dimethylpyrazolidin-4-yl)ethyl]-2-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-1,3-thiazole-5-carboxamide
—— 5-(Acetyloxy)-2-[7-(acetyloxy)-6-chloro-2,4,4-trimethyl-3,4-dihydro-2H-chromen-2-YL]-4-chlorophenyl acetate —— C24H24Cl2O7
5-(Acetyloxy)-2-[7-(acetyloxy)-6-chloro-2,4,4-trimethyl-3,4-dihydro-2H-chromen-2-YL]-4-chlorophenyl acetate
—— Kaempferid, TMS —— C25H36O6Si3
Kaempferid, TMS
—— Alpinon, TMS —— C20H24O5Si
Alpinon, TMS
—— Pinobanksin-3-propanoate, bis-TMS —— C24H32O6Si2
Pinobanksin-3-propanoate, bis-TMS
—— Pinobanksin-3-isobutanoate, bis-TMS —— C25H34O6Si2
Pinobanksin-3-isobutanoate, bis-TMS
—— [[2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea —— C18H15ClFN3O3S
[[2-(6-chloro-4H-1,3-benzodioxin-8-yl)-6-fluoro-2,3-dihydrochromen-4-ylidene]amino]thiourea
—— [2-(3-Bromo-4-methoxyphenyl)-4-oxochromen-3-yl] 2-(1,3-dioxoisoindol-2-yl)propanoate —— C27H18BrNO7
[2-(3-Bromo-4-methoxyphenyl)-4-oxochromen-3-yl] 2-(1,3-dioxoisoindol-2-yl)propanoate
—— 4-chloro-9-(4-chlorophenyl)-11-(4-methoxyphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C26H20Cl2N4O2S
4-chloro-9-(4-chlorophenyl)-11-(4-methoxyphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(3R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C27H30O14
5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(3R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— (S)-[(2R,3S)-2,3-trans-3-Acetoxy-8-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',5,7-tetramethoxyflavan] —— C42H46O14
(S)-[(2R,3S)-2,3-trans-3-Acetoxy-8-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',5,7-tetramethoxyflavan]
—— 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)- —— C28H32O15
4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
—— (R)-[(2R,3S)-2,3-trans-3-Acetoxy-8-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',5,7-tetramethoxyflavan] —— C42H46O14
(R)-[(2R,3S)-2,3-trans-3-Acetoxy-8-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',5,7-tetramethoxyflavan]
—— (2R,3S)-2,3-trans-3-Acetoxy-6-[(2R,3S,4S)-2,3-trans-3,4-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-4-yl]-3',4',5,7-tetramethoxyflavan —— C42H46O14
(2R,3S)-2,3-trans-3-Acetoxy-6-[(2R,3S,4S)-2,3-trans-3,4-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-4-yl]-3',4',5,7-tetramethoxyflavan
—— Isorhamnetin (4TMS) —— C28H44O7Si4
Isorhamnetin (4TMS)
—— [6-Methyl-2-(4-methylphenyl)-4-oxochromen-3-yl] 2-(2,4-dichlorophenoxy)propanoate —— C26H20Cl2O5
[6-Methyl-2-(4-methylphenyl)-4-oxochromen-3-yl] 2-(2,4-dichlorophenoxy)propanoate
—— 2-(1H-benzimidazol-2-yl)-2-[2-(3,4-dimethoxyphenyl)-6-methylchromen-4-ylidene]acetonitrile —— C27H21N3O3
2-(1H-benzimidazol-2-yl)-2-[2-(3,4-dimethoxyphenyl)-6-methylchromen-4-ylidene]acetonitrile
—— (+/-)-Naringenin, O,O',O''-tri(heptafluorobutyryl)- —— C27H9F21O8
(+/-)-Naringenin, O,O',O''-tri(heptafluorobutyryl)-
—— 4H-1-Benzopyran-4-one, 5-(acetyloxy)-2-[3-(acetyloxy)-4-methoxyphenyl]-7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]- —— C32H36O17
4H-1-Benzopyran-4-one, 5-(acetyloxy)-2-[3-(acetyloxy)-4-methoxyphenyl]-7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-
—— 4'-Hydroxyflavanone, tert.-butyldimethylsilyl ether —— C21H26O3Si
4'-Hydroxyflavanone, tert.-butyldimethylsilyl ether
—— N,N-dimethyl-2,4-diphenyl-2H-chromen-2-amine —— C23H21NO
N,N-dimethyl-2,4-diphenyl-2H-chromen-2-amine
—— 1-Dodecyl-3-(4-methoxyphenyl)benzo[f]chromen-4-ium —— C32H39O2+
1-Dodecyl-3-(4-methoxyphenyl)benzo[f]chromen-4-ium
—— 6-Hydroxyflavone-beta-D-glucoside, tetra(trifluoroacetyl)- —— C29H16F12O12
6-Hydroxyflavone-beta-D-glucoside, tetra(trifluoroacetyl)-
—— 2-(3,4-Di(n-butyl)oxyphenyl)-2,3-dihydro-5,7-di(n-butyl)oxy-4H-1-benzopyran-4-one —— C31H44O6
2-(3,4-Di(n-butyl)oxyphenyl)-2,3-dihydro-5,7-di(n-butyl)oxy-4H-1-benzopyran-4-one
—— 2-(2-acetoxy-phenyl)-chroman-4-one —— C17H14O4
2-(2-acetoxy-phenyl)-chroman-4-one
—— [2,6'-Bi-2H-1-benzopyran]-4(3H)-one, 3',4'-dihydro-3,5,7-trihydroxy-5'-methoxy-2',2'-dimethyl-, (2S-trans)- —— C21H22O7
[2,6'-Bi-2H-1-benzopyran]-4(3H)-one, 3',4'-dihydro-3,5,7-trihydroxy-5'-methoxy-2',2'-dimethyl-, (2S-trans)-
—— 4-(2-phenyl-2H-chromen-2-yl)morpholine —— C19H19NO2
4-(2-phenyl-2H-chromen-2-yl)morpholine
—— 2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5,7-di(n-propyl)oxy-4H-1-benzopyran-4-one —— C27H36O6
2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5,7-di(n-propyl)oxy-4H-1-benzopyran-4-one
—— 9-(3-fluorophenyl)-4-methyl-11-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C27H23FN4OS
9-(3-fluorophenyl)-4-methyl-11-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— 2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxy-3,5-dimethoxyphenyl)-, cis-(+/-)- —— C17H18O7
2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxy-3,5-dimethoxyphenyl)-, cis-(+/-)-
—— 9-(4-chlorophenyl)-4-methyl-11-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene —— C27H23ClN4OS
9-(4-chlorophenyl)-4-methyl-11-(4-methylphenyl)-14-methylsulfanyl-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2(7),3,5,14,16-hexaene
—— [2-(2-Chlorophenyl)-5,7-dimethyl-4-oxochromen-3-yl] 3-(3,4-dimethoxyphenyl)prop-2-enoate —— C28H23ClO6
[2-(2-Chlorophenyl)-5,7-dimethyl-4-oxochromen-3-yl] 3-(3,4-dimethoxyphenyl)prop-2-enoate
—— 9-(4-chloro-3-fluorophenyl)-11-(3,4-dimethoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C26H20ClFN4O3
9-(4-chloro-3-fluorophenyl)-11-(3,4-dimethoxyphenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene
—— 5,4'-Dihydroxy-7-methoxyflavanone, trimethylsilyl ether —— C19H22O5Si
5,4'-Dihydroxy-7-methoxyflavanone, trimethylsilyl ether
—— (+/-)-Naringenin, O,O'-bis(trimethylsilyl)- —— C21H28O5Si2
(+/-)-Naringenin, O,O'-bis(trimethylsilyl)-
—— 2-[[6-[[2-(3,4-Dihydroxyphenyl)-7-hydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-1-ium-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol —— C33H43O20+
2-[[6-[[2-(3,4-Dihydroxyphenyl)-7-hydroxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-1-ium-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
—— 9-(3,4-dimethoxyphenyl)-11-(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 —— C28H26N4O3S
9-(3,4-dimethoxyphenyl)-11-(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
—— 11-(4-bromophenyl)-4-fluoro-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 —— C24H16BrFN4O
11-(4-bromophenyl)-4-fluoro-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
—— 9-(2-ethoxyphenyl)-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 —— C26H23N5O2
9-(2-ethoxyphenyl)-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
—— 1-[[2-(3,4-Dimethoxyphenyl)-6-ethoxychromen-4-ylidene]amino]propan-2-ol —— C22H25NO5
1-[[2-(3,4-Dimethoxyphenyl)-6-ethoxychromen-4-ylidene]amino]propan-2-ol
—— 3'-O-methylepicatechin —— C16H16O6
3'-O-methylepicatechin
—— 11-(3-bromo-4-methoxyphenyl)-9-(3-bromophenyl)-8-oxa-12,13,15,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,14,16-hexaene —— C25H18Br2N4O2
11-(3-bromo-4-methoxyphenyl)-9-(3-bromophenyl)-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-Di(isopropyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(isopropyl)oxy-4H-1-benzopyran-4-one —— C24H30O6
2-(3,4-Di(isopropyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(isopropyl)oxy-4H-1-benzopyran-4-one
—— 2-(3,4-Di(2-methylpropyl)oxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one —— C23H28O6
2-(3,4-Di(2-methylpropyl)oxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
—— (2R,3S)-2,3-trans-3-Acetoxy-6-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',7,8-tetramethoxyflavan —— C42H46O14
(2R,3S)-2,3-trans-3-Acetoxy-6-[(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl]-3',4',7,8-tetramethoxyflavan
—— 2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(n-propyl)oxy-4H-1-benzopyran-4-one —— C24H30O6
2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(n-propyl)oxy-4H-1-benzopyran-4-one
—— 5-Hydroxy-7-methoxyflavanone, trifluoroacetate —— C18H13F3O5
5-Hydroxy-7-methoxyflavanone, trifluoroacetate
—— 2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one —— C21H24O6
2-(3,4-Di(n-propyl)oxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
—— 2-(3,4-Di(n-butyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(n-butyl)oxy-4H-1-benzopyran-4-one —— C27H36O6
2-(3,4-Di(n-butyl)oxyphenyl)-2,3-dihydro-5-hydroxy,7-(n-butyl)oxy-4H-1-benzopyran-4-one
—— 5-Hydroxy-7-methoxyflavanone, heptafluorobutyrate —— C20H13F7O5
5-Hydroxy-7-methoxyflavanone, heptafluorobutyrate