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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-(3,4-dihydroxy-phenyl)-8-dimethylaminomethyl-3,5,7-trihydroxy-chromen-4-one 30987-76-9 C18H17NO7
2-(3,4-dihydroxy-phenyl)-8-dimethylaminomethyl-3,5,7-trihydroxy-chromen-4-one
—— 6-hydroxyluteolin 5,7,4'-trimethyl ether 25782-20-1 C18H16O7
6-hydroxyluteolin 5,7,4'-trimethyl ether
—— 6-hydroxyluteolin 5,7,3'-trimethyl ether 25782-21-2 C18H16O7
6-hydroxyluteolin 5,7,3'-trimethyl ether
—— 6,8-C-diglucosylapigenin 29702-25-8 C21H20O10
6,8-C-diglucosylapigenin
—— 6-[(4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one 1233717-59-3 C28H24O10
6-[(4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— [(4aR,6S,7R,8S,8aS)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] hydrogen sulfate 1233717-60-6 C28H24O13S
[(4aR,6S,7R,8S,8aS)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] hydrogen sulfate
—— isovitexin 2"-O-sulfate 1173925-23-9 C21H20O13S
isovitexin 2"-O-sulfate
—— Saponaretin 29702-25-8 C21H20O10
Saponaretin
—— tertra-O-acetyleriodictyol 10210-16-9 C23H20O10
tertra-O-acetyleriodictyol
—— rac-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-1-benzopyran-6-ol 63233-39-6 C18H20O2
rac-3,4-dihydro-5,7,8-trimethyl-2-phenyl-2H-1-benzopyran-6-ol
—— apigenin 6-C-glucoside-8-C-arabinoside 51938-32-0 C26H28O14
apigenin 6-C-glucoside-8-C-arabinoside
—— Shaftoside 51938-32-0 C26H28O14
Shaftoside
—— 2,5,7-Trihydroxy-4'-methoxyflavanon 58124-20-2 C16H14O6
2,5,7-Trihydroxy-4'-methoxyflavanon
—— isocytisoside 4328-19-2 C22H22O10
isocytisoside
—— [(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-2-methyl-4-(pyrrolidine-1-carbonyloxy)oxan-3-yl] pyrrolidine-1-carboxylate 1374854-15-5 C31H34N2O12
[(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-2-methyl-4-(pyrrolidine-1-carbonyloxy)oxan-3-yl] pyrrolidine-1-carboxylate
—— (2S,3R,4S,5S,6R)-2-[2-[(2S)-8-(2-hydroxyethyl)-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 1329043-47-1 C25H32O10
(2S,3R,4S,5S,6R)-2-[2-[(2S)-8-(2-hydroxyethyl)-7-methoxy-3,4-dihydro-2H-chromen-2-yl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— quercetin 4'-O-(6-O-oleuropeoyl)-α-D-glucopyranoside 1187303-39-4 C31H34O14
quercetin 4'-O-(6-O-oleuropeoyl)-α-D-glucopyranoside
—— 5,7,4'-trihydroxy-6-C-(β-D-xylopyranosyl)flavone 83162-83-8 C20H18O9
5,7,4'-trihydroxy-6-C-(β-D-xylopyranosyl)flavone
—— 5,7,4'-trihydroxy-6-C-(β-D-xylopyranosyl)flavone 38642-54-5 C20H18O9
5,7,4'-trihydroxy-6-C-(β-D-xylopyranosyl)flavone
—— hesperetin-7-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl 1554106-34-1 C28H34O16
hesperetin-7-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl
—— Acetic 5-hydroxy-2-(4-hydroxy-phenyl)-4-oxo-chroman-7-yl ester 128373-95-5 C17H14O6
Acetic 5-hydroxy-2-(4-hydroxy-phenyl)-4-oxo-chroman-7-yl ester
—— 7-acetoxy-2-(4-acetoxy-phenyl)-chroman-5-ol 66312-99-0 C19H18O6
7-acetoxy-2-(4-acetoxy-phenyl)-chroman-5-ol
—— 6,8-difluoro-2-(3,5-difluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one 180595-86-2 C25H24F4N2O4
6,8-difluoro-2-(3,5-difluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one
—— 5,7-dihydroxy-3-(2-methylbenzyloxy)-2-phenyl-4H-chromen-4-one 1256264-53-5 C23H18O5
5,7-dihydroxy-3-(2-methylbenzyloxy)-2-phenyl-4H-chromen-4-one
—— 3-methyl-2-(o-tolyl)-4H-chromen-4-one 1233712-96-3 C17H14O2
3-methyl-2-(o-tolyl)-4H-chromen-4-one
—— 5,7-dihydroxy-2-(4'-methoxyphenyl)benzopyrilium chloride 1090-74-0 C16H13O4*Cl
5,7-dihydroxy-2-(4'-methoxyphenyl)benzopyrilium chloride
—— [5-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl] benzoate 73197-00-9 C23H16O6
[5-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl] benzoate
—— 7-Ethoxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one 1052063-32-7 C18H16O5
7-Ethoxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one
—— 5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone 20633-93-6 C28H32O14
5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone
—— [7-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-5-yl] 4-methoxybenzoate 1052063-33-8 C24H18O7
[7-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-5-yl] 4-methoxybenzoate
—— [5-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl] 4-methoxybenzoate 1052063-34-9 C24H18O7
[5-Hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl] 4-methoxybenzoate
—— Pulchellidin —— C16H13O7+
Pulchellidin
—— swertisin-5-O-β-D-glucoside 73051-75-9 C28H32O15
swertisin-5-O-β-D-glucoside
—— Europinidin —— C17H15O7+
Europinidin
—— dimethyl-3,8 diphenyl-2,9 tetrahydro-3,4,7,8 benzo<1,2-b:6,5-b'>dipyranne 80067-77-2 C26H26O2
dimethyl-3,8 diphenyl-2,9 tetrahydro-3,4,7,8 benzo<1,2-b:6,5-b'>dipyranne
—— 5,7-dimethoxy-2-(4-(2-morpholin-4-ylethoxy)phenyl)chromen-4-one 1612891-73-2 C23H25NO6
5,7-dimethoxy-2-(4-(2-morpholin-4-ylethoxy)phenyl)chromen-4-one
—— 2-[8-allyl-3-nitro-4-oxo-4H-1-benzopyran-2-yl]benzoic acid benzyl ester 596108-57-5 C26H19NO6
2-[8-allyl-3-nitro-4-oxo-4H-1-benzopyran-2-yl]benzoic acid benzyl ester
—— 6-[6-(Diethylamino)hexoxy]-2-phenyl-4H-1-benzopyran-4-one hydrochloride 139653-06-8 C25H31NO3*ClH
6-[6-(Diethylamino)hexoxy]-2-phenyl-4H-1-benzopyran-4-one hydrochloride
—— 2-[4-[2-(1-piperidino)-ethoxy]phenyl]-3-[4-hydroxyphenyl]-7-hydroxy-2H-1-benzopyran 130064-36-7 C28H29NO4
2-[4-[2-(1-piperidino)-ethoxy]phenyl]-3-[4-hydroxyphenyl]-7-hydroxy-2H-1-benzopyran
—— 6-bromo-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 91830-42-1 C17H11BrO4
6-bromo-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid
—— epicatechin-(4β->8,2β->O->7)-epiafzelechin-(4α->8)-epicatechin 130918-29-5 C45H36O17
epicatechin-(4β->8,2β->O->7)-epiafzelechin-(4α->8)-epicatechin
—— 6-<<6-<4-(2-hydroxyethyl)piperidyl>hexyl>oxy>flavone 139652-70-3 C28H35NO4
6-<<6-<4-(2-hydroxyethyl)piperidyl>hexyl>oxy>flavone
—— (E)-7-methoxy-2-(4-methoxyphenyl)-4-(4-methoxystyryl)-2-methylchroman 1346937-00-5 C27H28O4
(E)-7-methoxy-2-(4-methoxyphenyl)-4-(4-methoxystyryl)-2-methylchroman
—— epicatechin-(4β->8,2β->O->7)-epiafzelechin 130918-33-1 C30H24O11
epicatechin-(4β->8,2β->O->7)-epiafzelechin
—— 3-(difluoromethoxy)-2-phenyl-4H-chromen-4-one 1454765-36-6 C16H10F2O3
3-(difluoromethoxy)-2-phenyl-4H-chromen-4-one
—— 2-(4-chlorophenyl)-5,7-dihydroxy-3-methoxy-8-(3-methylbut-2-enyl)-4H-chromen-4-one 1192136-10-9 C21H19ClO5
2-(4-chlorophenyl)-5,7-dihydroxy-3-methoxy-8-(3-methylbut-2-enyl)-4H-chromen-4-one
—— 2-(4-chlorophenyl)-5-hydroxy-3-methoxy-7-(methoxymethoxy)-8-(3-methylbut-2-enyl)-4H-chromen-4-one 1192136-09-6 C23H23ClO6
2-(4-chlorophenyl)-5-hydroxy-3-methoxy-7-(methoxymethoxy)-8-(3-methylbut-2-enyl)-4H-chromen-4-one
—— (6S,6aR,10aR)-7-amino-6-(4-methoxyphenyl)-10-methyl-6a-nitro-9-phenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 1438276-59-5 C28H23N3O4
(6S,6aR,10aR)-7-amino-6-(4-methoxyphenyl)-10-methyl-6a-nitro-9-phenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile
—— (6S,6aR,10aR)-7-amino-2-chloro-10-methyl-6a-nitro-6,9-diphenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 1438276-61-9 C27H20ClN3O3
(6S,6aR,10aR)-7-amino-2-chloro-10-methyl-6a-nitro-6,9-diphenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile
—— (6S,6aR,10aR)-2-chloro-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 1438276-79-9 C27H20ClN3O3
(6S,6aR,10aR)-2-chloro-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile