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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
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-nitrophenyl)prop-2-enoate 217661-73-9 C41H44NO23
[(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-nitrophenyl)prop-2-enoate
—— 9-bromo-4-methoxy-7-(2-methoxyphenyl)-5H-furo[3,2-g]chromen-5-one 1616883-62-5 C19H13BrO5
9-bromo-4-methoxy-7-(2-methoxyphenyl)-5H-furo[3,2-g]chromen-5-one
—— 2-(3-methoxyphenyl)-2-methyl-2H-chromene 1393641-95-6 C17H16O2
2-(3-methoxyphenyl)-2-methyl-2H-chromene
—— 3-acetoxy-4-thioflavone 85726-14-3 C17H12O3S
3-acetoxy-4-thioflavone
—— ethyl 4-[2-oxo-1-(2-(4-oxo-2-phenyl-4H-chromen-7-yl)hydrazono)propyl]piperazine-1-carboxylate 1394154-27-8 C25H26N4O5
ethyl 4-[2-oxo-1-(2-(4-oxo-2-phenyl-4H-chromen-7-yl)hydrazono)propyl]piperazine-1-carboxylate
—— 7-O-β-D-galactoside flavone 1209000-35-0 C21H20O8
7-O-β-D-galactoside flavone
—— N-(4-fluorophenyl)-2-(4-oxo-2-phenyl-4H-chromen-6-yloxy)acetamide 1070399-67-5 C23H16FNO4
N-(4-fluorophenyl)-2-(4-oxo-2-phenyl-4H-chromen-6-yloxy)acetamide
—— 7-O-α-D-glucopyranosyl-3,8-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-methoxy-4H-1-benzopyran-4-one 956315-69-8 C23H24O13
7-O-α-D-glucopyranosyl-3,8-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-methoxy-4H-1-benzopyran-4-one
—— 3',4',5,7-tetramyristoyloxyflavone 1399385-17-1 C71H114O10
3',4',5,7-tetramyristoyloxyflavone
—— 3-O-(2-oxiranylmethyl)karanjonol 1244042-48-5 C20H14O5
3-O-(2-oxiranylmethyl)karanjonol
—— isoorientin 4'-O-glucoside 38950-96-8 C27H30O16
isoorientin 4'-O-glucoside
—— 8-(bromomethyl)-6-chloro-2-(2-chlorophenyl)-4H-chromen-4-one 1343513-60-9 C16H9BrCl2O2
8-(bromomethyl)-6-chloro-2-(2-chlorophenyl)-4H-chromen-4-one
—— 4'-methoxy-3',5,7-trihydroxy-8-(3,3-dimethylallyl)flavonol 3-O-α-L-rhamnopyranosyl(1->2)-α-L-rhamnopyranoside 1370593-62-6 C33H40O15
4'-methoxy-3',5,7-trihydroxy-8-(3,3-dimethylallyl)flavonol 3-O-α-L-rhamnopyranosyl(1->2)-α-L-rhamnopyranoside
—— 2-(4-Azidophenyl)-5,7-dihydroxy-3-phenylmethoxychromen-4-one 322405-77-6 C22H15N3O5
2-(4-Azidophenyl)-5,7-dihydroxy-3-phenylmethoxychromen-4-one
—— [3,8-dibromo-7-butoxy-2-(4-methoxyphenyl)-6-nitro-4-oxo-3H-chromen-2-yl] acetate 139589-33-6 C22H21Br2NO8
[3,8-dibromo-7-butoxy-2-(4-methoxyphenyl)-6-nitro-4-oxo-3H-chromen-2-yl] acetate
—— Methyl 2,6-dimethyl-5-nitro-4-(2-phenyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate 94420-28-7 C24H20N2O6
Methyl 2,6-dimethyl-5-nitro-4-(2-phenyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate
—— 7-(4-methoxy-phenyl)-3-methyl-furo[2,3-<i>f</i>]chromen-9-one 854703-41-6 C19H14O4
7-(4-methoxy-phenyl)-3-methyl-furo[2,3-<i>f</i>]chromen-9-one
—— 1352172-07-6 C41H28Br2N4O3
—— 7-methoxy-3-methyl-2-phenyl-8-(prop-2-en-1-yl)-4H-1-benzopyran-4-one 18651-22-4 C20H18O3
7-methoxy-3-methyl-2-phenyl-8-(prop-2-en-1-yl)-4H-1-benzopyran-4-one
—— trimethyl-[2-(4-oxo-2-phenyl-4<i>H</i>-chromen-7-yloxy)-ethyl]-ammonium; iodide 111141-85-6 C20H22NO3*I
trimethyl-[2-(4-oxo-2-phenyl-4<i>H</i>-chromen-7-yloxy)-ethyl]-ammonium; iodide
—— 2-(1,3-Benzodioxol-5-yl)-3-methoxy-6-methyl-8-pyrrolidin-1-ylchromen-4-one 934374-17-1 C22H21NO5
2-(1,3-Benzodioxol-5-yl)-3-methoxy-6-methyl-8-pyrrolidin-1-ylchromen-4-one
—— amorilin 4',5,7-trisethoxymethyl ether 130236-68-9 C39H54O8
amorilin 4',5,7-trisethoxymethyl ether
—— ethyl 7-ethyl-4,10-dioxo-2-phenyl-7,10-dihydro-4H-pyrano[2,3-f]quinoline-9-carboxylate 1492929-11-9 C23H19NO5
ethyl 7-ethyl-4,10-dioxo-2-phenyl-7,10-dihydro-4H-pyrano[2,3-f]quinoline-9-carboxylate
—— 8-allyl-2-(4-chlorophenyl)-7-hydroxy-5-methoxy-4-oxo-4H-chromene-6-carbaldehyde 1616883-79-4 C20H15ClO5
8-allyl-2-(4-chlorophenyl)-7-hydroxy-5-methoxy-4-oxo-4H-chromene-6-carbaldehyde
—— [4,8’]-2,3-trans-3.4-trans:2’,3’-trans-octabenzyloxy-(+)-catechin-3-(tribenzyloxy)gall 828249-33-8 C114H96O16
[4,8’]-2,3-trans-3.4-trans:2’,3’-trans-octabenzyloxy-(+)-catechin-3-(tribenzyloxy)gall
—— 3',4',5'-trimethoxy-3-methylflavone-8-carboxylic acid 90102-11-7 C20H18O7
3',4',5'-trimethoxy-3-methylflavone-8-carboxylic acid
—— 2-[2,4-Bis(2-phenoxyethoxy)phenyl]-3-hydroxychromen-4-one 1099682-05-9 C31H26O7
2-[2,4-Bis(2-phenoxyethoxy)phenyl]-3-hydroxychromen-4-one
—— 21,21-diphenyl-2,3,5,6,8,9,11,12,14,15-decahydro-21H-[1,4,7,10,13,16]hexaoxacyclooctadeca[2,3-h]chromene 1214883-16-5 C29H30O6
21,21-diphenyl-2,3,5,6,8,9,11,12,14,15-decahydro-21H-[1,4,7,10,13,16]hexaoxacyclooctadeca[2,3-h]chromene
—— 2,3,5,6,8,9,11,12,14,15-decahydro-21,21-diphenyl-21H-chromeno[7,8-b][1,4,7,10,13,16]hexaoxacyclooctadecyne 1214883-18-7 C31H34O7
2,3,5,6,8,9,11,12,14,15-decahydro-21,21-diphenyl-21H-chromeno[7,8-b][1,4,7,10,13,16]hexaoxacyclooctadecyne
—— kaempferol 3-O-α-Rha-(1->2)-β-Glc 32602-81-6 C27H30O15
kaempferol 3-O-α-Rha-(1->2)-β-Glc
—— (2R,3S)-2-(4-Chloro-phenyl)-3-hydroxy-6-methyl-chroman-4-one 139006-44-3 C16H13ClO3
(2R,3S)-2-(4-Chloro-phenyl)-3-hydroxy-6-methyl-chroman-4-one
—— (7R,8R)-7-acetoxy-2-methyl-8-phenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one 868634-07-5 C19H16N2O4
(7R,8R)-7-acetoxy-2-methyl-8-phenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one
—— 3,8-dibromo-7-butoxy-2-(4-chlorophenyl)-6-nitrochromen-4-one 139589-37-0 C19H14Br2ClNO5
3,8-dibromo-7-butoxy-2-(4-chlorophenyl)-6-nitrochromen-4-one
—— (4-(4-chlorophenylthio)-2,2-dimethyl-2H-chromen-3-yl)(4-methoxyphenyl)methanol 1343415-00-8 C25H23ClO3S
(4-(4-chlorophenylthio)-2,2-dimethyl-2H-chromen-3-yl)(4-methoxyphenyl)methanol
—— N-[2-nitro-4-(3,6,8-tribromo-7-methyl-4-oxochromen-2-yl)phenyl]acetamide 145665-87-8 C18H11Br3N2O5
N-[2-nitro-4-(3,6,8-tribromo-7-methyl-4-oxochromen-2-yl)phenyl]acetamide
—— 5,7-diethoxy-2-(3-ethoxy-4-methoxy-phenyl)-3,8-dimethoxy-chromen-4-one 20921-25-9 C24H28O8
5,7-diethoxy-2-(3-ethoxy-4-methoxy-phenyl)-3,8-dimethoxy-chromen-4-one
—— 7-methyl-2-phenyl-2H-chromene 1162693-00-6 C16H14O
7-methyl-2-phenyl-2H-chromene
—— N-{2-[4-(benzyloxy)-3-nitrophenyl]-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl}acetamide 372101-96-7 C25H20N2O7
N-{2-[4-(benzyloxy)-3-nitrophenyl]-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl}acetamide
—— 8-Brom-5-acetoxy-flavon 93261-74-6 C17H11BrO4
8-Brom-5-acetoxy-flavon
—— 6-[2-(2,6-difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine 728934-68-7 C20H16F2N2O2
6-[2-(2,6-difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine
—— 7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl 7-(2-(4-(hydroxymethyl)phenylamino)-2-oxoethylamino)-7-oxoheptanoate 1469894-75-4 C52H48N2O11
7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl 7-(2-(4-(hydroxymethyl)phenylamino)-2-oxoethylamino)-7-oxoheptanoate
—— 6-acetyl-7-hydroxy-2,3-trans-flavan-3-ol 90363-13-6 C17H16O4
6-acetyl-7-hydroxy-2,3-trans-flavan-3-ol
—— tert-butyl (2R,3S)-4-oxo-3-(3-oxobutyl)-2-phenylchroman-3-carboxylate 1315334-84-9 C24H26O5
tert-butyl (2R,3S)-4-oxo-3-(3-oxobutyl)-2-phenylchroman-3-carboxylate
—— Quercetin-7-pentylether 94683-83-7 C20H20O7
Quercetin-7-pentylether
—— apigenin 7-O-(3,4-di-O-acetyl)-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside 1345732-57-1 C31H34O16
apigenin 7-O-(3,4-di-O-acetyl)-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside
—— 2-(6-Methyl-4-oxo-2-phenylchromen-8-yl)acetonitrile 87626-73-1 C18H13NO2
2-(6-Methyl-4-oxo-2-phenylchromen-8-yl)acetonitrile
—— 8-bromo-7-butoxy-2-(2,4-dichlorophenyl)-6-nitrochromen-4-one 135878-80-7 C19H14BrCl2NO5
8-bromo-7-butoxy-2-(2,4-dichlorophenyl)-6-nitrochromen-4-one
—— 3-[4-methoxy-7-(2-methoxyphenyl)-5-oxo-5H-furo[3,2-g]chromen-9-yl]acrylaldehyde 1616883-65-8 C22H16O6
3-[4-methoxy-7-(2-methoxyphenyl)-5-oxo-5H-furo[3,2-g]chromen-9-yl]acrylaldehyde
—— 2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-8-(1-methyl-4-piperidinyl)-4H-chromen-4-one 372103-29-2 C24H26ClNO4
2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-8-(1-methyl-4-piperidinyl)-4H-chromen-4-one
—— cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-((E)-caffeoyl)-β-galactopyranoside] 1106838-62-3 C35H35O18
cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-((E)-caffeoyl)-β-galactopyranoside]