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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
—— 5,6,4'-Trihydroxy-8,3'-dimethoxyflavone —— C17H14O7
5,6,4'-Trihydroxy-8,3'-dimethoxyflavone
—— 5-O-Methylleridol —— C19H20O5
5-O-Methylleridol
—— 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,3-dihydrochromen-4-one —— C27H32O15
2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,3-dihydrochromen-4-one
—— 11-(1,3-dihydroxypropan-2-yloxy)-2-(4-hydroxy-3-methoxyphenyl)-5-(2-imidazol-1-ylethyl)-3,4,5,6-tetrahydro-2H-naphtho[2,1-f]chromene-3,8-diol —— C32H34N2O8
11-(1,3-dihydroxypropan-2-yloxy)-2-(4-hydroxy-3-methoxyphenyl)-5-(2-imidazol-1-ylethyl)-3,4,5,6-tetrahydro-2H-naphtho[2,1-f]chromene-3,8-diol
—— 8-Prenylquercetin 143724-75-8 C20H18O7
8-Prenylquercetin
—— Arteanoflavone —— C19H18O8
Arteanoflavone
—— 3-[3,5-Dihydroxy-6-methyl-4-(3,4,5,6-tetrahydroxyoxan-2-yl)oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one —— C27H32O16
3-[3,5-Dihydroxy-6-methyl-4-(3,4,5,6-tetrahydroxyoxan-2-yl)oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
—— Agestricin C 123768-58-1 C19H20O7
Agestricin C
—— 2-(4-hydroxy-3-methoxyphenyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3,4-dihydro-2H-chromene-4,5,7-triol —— C22H26O11
2-(4-hydroxy-3-methoxyphenyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3,4-dihydro-2H-chromene-4,5,7-triol
—— 5,7-dihydroxy-2-phenyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)chromen-4-one —— C26H28O13
5,7-dihydroxy-2-phenyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-(3,4,5-trihydroxyoxan-2-yl)chromen-4-one
—— 2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol 69912-75-0 C16H16O6
2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2-[4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C26H30O14
2-[4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— [5,7-diacetyloxy-2-[4,5-diacetyloxy-2-[3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-4-[3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromen-8-yl]phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate —— C75H68O33
[5,7-diacetyloxy-2-[4,5-diacetyloxy-2-[3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-4-[3,5,7-triacetyloxy-2-(3,4-diacetyloxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromen-8-yl]phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate
—— 5,7,3',4'-Tetrahydroxy-3-methoxy-8,5'-diprenylflavone —— C26H28O7
5,7,3',4'-Tetrahydroxy-3-methoxy-8,5'-diprenylflavone
—— 2-[[2-(3,4-dihydroxy-5-methoxyphenyl)-4-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol —— C24H30O12
2-[[2-(3,4-dihydroxy-5-methoxyphenyl)-4-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol
—— 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one —— C29H34O16
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
—— 6-(3,7-Dimethylocta-2,6-dienyl)-5,7-dihydroxy-2-phenylchromen-4-one —— C25H26O4
6-(3,7-Dimethylocta-2,6-dienyl)-5,7-dihydroxy-2-phenylchromen-4-one
—— [2-(3-Acetyloxy-4-methoxyphenyl)-5-methoxy-4-oxochromen-7-yl] acetate —— C21H18O8
[2-(3-Acetyloxy-4-methoxyphenyl)-5-methoxy-4-oxochromen-7-yl] acetate
—— 2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5-dihydroxy-3,4-dihydro-2H-pyrano[2,3-h]chromen-8-one —— C48H38O19
2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5-dihydroxy-3,4-dihydro-2H-pyrano[2,3-h]chromen-8-one
—— 6-[6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[[5-(3-methylbutyl)-1H-pyrrol-3-yl]methyl]-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid —— C37H41NO18
6-[6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-6-[[5-(3-methylbutyl)-1H-pyrrol-3-yl]methyl]-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
—— 2-[3,4-dihydroxy-2,5-bis(2-hydroxyethylsulfanyl)phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol —— C19H22O8S2
2-[3,4-dihydroxy-2,5-bis(2-hydroxyethylsulfanyl)phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
—— 5-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]pyrrolidin-2-one —— C19H19NO7
5-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]pyrrolidin-2-one
—— N-(2-(4-ethoxyphenyl)-4-oxo-4H-chromen-7-yl)isonicotinamide —— C23H18N2O4
N-(2-(4-ethoxyphenyl)-4-oxo-4H-chromen-7-yl)isonicotinamide
—— 2-(2,5-Dihydroxy-3,4-dimethoxy-phenyl)-5,7-dihydroxy-6-methoxy-chromen-4-one —— C18H16O9
2-(2,5-Dihydroxy-3,4-dimethoxy-phenyl)-5,7-dihydroxy-6-methoxy-chromen-4-one
—— Gossypetin 3,5,7,8,3'-pentamethyl ether —— C20H20O8
Gossypetin 3,5,7,8,3'-pentamethyl ether
—— 2-(4-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxy-6,8-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one —— C29H36O14
2-(4-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-5-hydroxy-7-methoxy-6,8-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one
—— 3,7-Dihydroxy-2-[4-hydroxy-3-[[3-(methylaminomethyl)phenyl]methyl]phenyl]-5-(3-hydroxypropoxy)chromen-4-one —— C27H27NO7
3,7-Dihydroxy-2-[4-hydroxy-3-[[3-(methylaminomethyl)phenyl]methyl]phenyl]-5-(3-hydroxypropoxy)chromen-4-one
—— 5,7-Dihydroxy-2-[7-hydroxy-2-(2-hydroxy-6-methylhept-5-en-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-3-methoxychromen-4-one —— C26H28O8
5,7-Dihydroxy-2-[7-hydroxy-2-(2-hydroxy-6-methylhept-5-en-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-3-methoxychromen-4-one
—— 5-Hydroxy-2-(2-hydroxy-3,4,5-trimethoxy-phenyl)-7-methoxy-chromen-4-one —— C19H18O8
5-Hydroxy-2-(2-hydroxy-3,4,5-trimethoxy-phenyl)-7-methoxy-chromen-4-one
—— 5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol —— C60H48O24
5,13-bis(3,4-dihydroxyphenyl)-7-[2-(3,4-dihydroxyphenyl)-4-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
—— 10-(Benzo[d][1,3]dioxol-5-yl)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-9,10-dihydropyrano[2,3-f]chromene-4,8-dione —— C26H18O9
10-(Benzo[d][1,3]dioxol-5-yl)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-9,10-dihydropyrano[2,3-f]chromene-4,8-dione
—— 1,3-dimethyl-2,4,6-trioxospiro(perhydropyrimidino-5)-3'-(2-phenylchromane) —— C20H18N2O4
1,3-dimethyl-2,4,6-trioxospiro(perhydropyrimidino-5)-3'-(2-phenylchromane)
—— Apigenin 5-O-beta-D-glucopyranoside; Apigenin 5-O-beta-D-glucoside; Apigenin 5-glucoside; Apigenin 5-beta-D-glucopyranoside —— C21H20O10
Apigenin 5-O-beta-D-glucopyranoside; Apigenin 5-O-beta-D-glucoside; Apigenin 5-glucoside; Apigenin 5-beta-D-glucopyranoside
—— methyl 3-(5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl)-3-(7-methoxy-1,3-benzodioxol-5-yl)propanoate —— C27H22O9
methyl 3-(5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl)-3-(7-methoxy-1,3-benzodioxol-5-yl)propanoate
—— 6-Hydroxy-7-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3-one —— C25H28O11
6-Hydroxy-7-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3-one
—— 5,17,23-tris(3,4-dihydroxyphenyl)-19-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,6,16,22,24-pentaoxaoctacyclo[21.7.1.15,13.02,21.03,14.07,12.015,20.025,30]dotriaconta-2,7,9,11,14,20,25,27,29-nonaene-9,11,18,27,29,31,32-heptol —— C60H46O24
5,17,23-tris(3,4-dihydroxyphenyl)-19-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,6,16,22,24-pentaoxaoctacyclo[21.7.1.15,13.02,21.03,14.07,12.015,20.025,30]dotriaconta-2,7,9,11,14,20,25,27,29-nonaene-9,11,18,27,29,31,32-heptol
—— [6-[3,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-7-yl]oxy-6-methyloxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate —— C42H46O23
[6-[3,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-7-yl]oxy-6-methyloxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
—— 5-Hydroxy-8-(4-hydroxyphenyl)-7-methoxy-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one —— C26H28O6
5-Hydroxy-8-(4-hydroxyphenyl)-7-methoxy-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
—— 5-Hydroxy-2-(4-hydroxyphenyl)-10-(6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)-9,10-dihydropyrano[2,3-f]chromene-4,8-dione —— C28H19NO8
5-Hydroxy-2-(4-hydroxyphenyl)-10-(6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)-9,10-dihydropyrano[2,3-f]chromene-4,8-dione
—— 5,7-dihydroxy-8-(1-(8-methoxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methylpiperazin-1-yl)-3-oxopropyl)-2-phenyl-4H-chromen-4-one —— C32H32N2O8
5,7-dihydroxy-8-(1-(8-methoxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methylpiperazin-1-yl)-3-oxopropyl)-2-phenyl-4H-chromen-4-one
—— 2-(2-Fluorophenyl)-6-methoxychroman-4-one —— C16H13FO3
2-(2-Fluorophenyl)-6-methoxychroman-4-one
—— 3-Methylquercetin 7-[galactosyl-(1->4)-glucoside] —— C28H32O17
3-Methylquercetin 7-[galactosyl-(1->4)-glucoside]
—— [4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate —— C36H36O18
[4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
—— methyl 3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-3-(2,4,5-trihydroxyphenyl)propanoate —— C25H24O11
methyl 3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-3-(2,4,5-trihydroxyphenyl)propanoate
—— N-[2-(4-tert-butylphenyl)-4-oxo-4H-chromen-6-yl]-4-chlorobenzamide —— C26H22ClNO3
N-[2-(4-tert-butylphenyl)-4-oxo-4H-chromen-6-yl]-4-chlorobenzamide
—— 2-[3-[6-(2,4-Dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one —— C35H30O11
2-[3-[6-(2,4-Dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
—— 2-[3-[2-[(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)methyl]-3-(hydroxymethyl)cyclohexyl]oxy-4-hydroxyphenyl]-11-methoxy-9-(2-methylpropyl)-5-pentyl-3,4,5,6-tetrahydro-2H-naphtho[2,1-f]chromene-3,8-diol —— C45H61N3O7
2-[3-[2-[(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)methyl]-3-(hydroxymethyl)cyclohexyl]oxy-4-hydroxyphenyl]-11-methoxy-9-(2-methylpropyl)-5-pentyl-3,4,5,6-tetrahydro-2H-naphtho[2,1-f]chromene-3,8-diol
—— 2-[2-[[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-2H-chromen-3-yl]peroxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol —— C34H44O21
2-[2-[[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy-2H-chromen-3-yl]peroxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— [6-[2-[2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate —— C29H32O18
[6-[2-[2-(3,4-Dihydroxyphenyl)-5,6-dihydroxy-4-oxochromen-7-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
—— 3-[6-[[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one —— C26H28O16
3-[6-[[3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one