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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
—— crotonoylthermopsoside 123656-61-1 C26H26O12
crotonoylthermopsoside
—— 5,7,4'-trihydroxy-3'-methoxyflavone-4'-O-β-D-(2''-O-acetyl)glucopyranoside 1215845-89-8 C24H24O12
5,7,4'-trihydroxy-3'-methoxyflavone-4'-O-β-D-(2''-O-acetyl)glucopyranoside
—— lysidiside W 1340542-84-8 C32H36O15
lysidiside W
—— 4-O-[[2-[4-(dimethylamino)phenyl]-7,9-dimethoxy-2-phenylbenzo[h]chromen-5-yl]methyl] 1-O-[2-(2-methylprop-2-enoyloxy)ethyl] butanedioate 1260501-60-7 C40H41NO9
4-O-[[2-[4-(dimethylamino)phenyl]-7,9-dimethoxy-2-phenylbenzo[h]chromen-5-yl]methyl] 1-O-[2-(2-methylprop-2-enoyloxy)ethyl] butanedioate
—— vitisin A 388089-38-1 C26H25O14
vitisin A
—— 3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-glucopyranosyl-(1→5)-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside 1408247-33-5 C33H40O21
3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-glucopyranosyl-(1→5)-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside
—— quercetin 3-O-α-L-rhamnopyranosyl(1'''→6'')-β-D-galactopyranoside-7-O-β-D-glucopyranosyl(1'''''→2''''')-β-D-glucopyranoside 1609449-44-6 C39H50O26
quercetin 3-O-α-L-rhamnopyranosyl(1'''→6'')-β-D-galactopyranoside-7-O-β-D-glucopyranosyl(1'''''→2''''')-β-D-glucopyranoside
—— 3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside 1408247-30-2 C27H30O16
3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside
—— 3,5,3'-trihydroxy-7,4'-dimethoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside 1408247-28-8 C28H32O16
3,5,3'-trihydroxy-7,4'-dimethoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside
—— 3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-galactopyranoside 1408247-32-4 C27H30O16
3,5,3',4'-tetrahydroxy-7-methoxyflavone-3-O-β-D-apiofuranosyl-(1→2)-β-D-galactopyranoside
—— rhamnazin-3-O-β-D-apiosyl-(1→2)-β-D-[6''-(3-hydroxy-3-methylglutaric methyl ester)]glucoside 1414369-64-4 C35H42O20
rhamnazin-3-O-β-D-apiosyl-(1→2)-β-D-[6''-(3-hydroxy-3-methylglutaric methyl ester)]glucoside
—— Peracetylated-SL0101 72165-31-2 C33H32O16
Peracetylated-SL0101
—— 4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 143631-95-2 C23H18O11
4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate
—— kaempferol-3-O-rhamnoside 28978-08-7 C21H20O10
kaempferol-3-O-rhamnoside
—— naringenin-ethylidene-norfloxacin 1517965-11-5 C33H32FN3O8
naringenin-ethylidene-norfloxacin
—— chrysin-ethylidene-norfloxacin 1517965-09-1 C33H30FN3O7
chrysin-ethylidene-norfloxacin
—— apigenin-ethylidene-norfloxacin 1613083-67-2 C33H30FN3O8
apigenin-ethylidene-norfloxacin
—— 2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran 130378-73-3 C21H16O2
2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran
—— Epigallocatechin gallate 3-palmitate 948837-66-9 C38H48O12
Epigallocatechin gallate 3-palmitate
—— 5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol 896121-45-2 C50H44O7
5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol
—— (2R,3S)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3,4,5-trimethoxybenzoate 121844-32-4 C30H34O11
(2R,3S)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3,4,5-trimethoxybenzoate
—— [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)carbamothioyloxy]-4,5-dihydroxybenzoate 1093758-49-6 C43H29NO16S
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)carbamothioyloxy]-4,5-dihydroxybenzoate
—— [(8R,9R)-5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-8-(3,4,5-trihydroxyphenyl)-9,10-dihydro-8H-pyrano[2,3-h]chromen-9-yl] 3,4,5-trihydroxybenzoate 1173162-09-8 C32H32O11
[(8R,9R)-5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-8-(3,4,5-trihydroxyphenyl)-9,10-dihydro-8H-pyrano[2,3-h]chromen-9-yl] 3,4,5-trihydroxybenzoate
—— [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4,5-trihydroxybenzoate 1173162-13-4 C32H34O11
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4,5-trihydroxybenzoate
—— (2R,3R)-5,7-bis(benzyloxy)-2-(3,4,5-tris(benzyloxy)phenyl)chroman-3-ol 332386-74-0 C50H44O7
(2R,3R)-5,7-bis(benzyloxy)-2-(3,4,5-tris(benzyloxy)phenyl)chroman-3-ol
—— (2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,5-dihydroxy-4-methoxybenzoate 360059-39-8 C23H20O11
(2S,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,5-dihydroxy-4-methoxybenzoate
—— [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] pyridine-4-carboxylate 224441-64-9 C21H17NO8
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] pyridine-4-carboxylate
—— [(5R,14R,15R,21R)-5,9,9,21,25,25-hexamethyl-15-(3,4,5-trihydroxyphenyl)-10,16,26-trioxahexacyclo[16.8.0.02,11.03,8.012,17.019,24]hexacosa-1(18),2(11),12(17)-trien-14-yl] 3,4,5-trihydroxybenzoate 1173275-70-1 C42H50O11
[(5R,14R,15R,21R)-5,9,9,21,25,25-hexamethyl-15-(3,4,5-trihydroxyphenyl)-10,16,26-trioxahexacyclo[16.8.0.02,11.03,8.012,17.019,24]hexacosa-1(18),2(11),12(17)-trien-14-yl] 3,4,5-trihydroxybenzoate
—— [(1S,5R,6R,13S,16R)-9-hydroxy-16-(2-hydroxypropan-2-yl)-13-methyl-5-(3,4,5-trihydroxyphenyl)-4,12-dioxatetracyclo[11.3.1.02,11.03,8]heptadeca-2(11),3(8),9-trien-6-yl] 3,4,5-trihydroxybenzoate 1173162-08-7 C32H34O12
[(1S,5R,6R,13S,16R)-9-hydroxy-16-(2-hydroxypropan-2-yl)-13-methyl-5-(3,4,5-trihydroxyphenyl)-4,12-dioxatetracyclo[11.3.1.02,11.03,8]heptadeca-2(11),3(8),9-trien-6-yl] 3,4,5-trihydroxybenzoate
—— (-)-epigallocatechin 4-fluorobenzoate 1256160-11-8 C22H17FO8
(-)-epigallocatechin 4-fluorobenzoate
—— (-)-epigallocatechin gallate 4'-monosulfate 145643-86-3 C22H18O14S
(-)-epigallocatechin gallate 4'-monosulfate
—— [(2R,3R,11R)-5-hydroxy-8,8,11-trimethyl-2-(3,4,5-trihydroxyphenyl)-3,4,8a,9,10,11,12,12a-octahydro-2H-isochromeno[3,4-h]chromen-3-yl] 3,4,5-trihydroxybenzoate 1173162-10-1 C32H34O11
[(2R,3R,11R)-5-hydroxy-8,8,11-trimethyl-2-(3,4,5-trihydroxyphenyl)-3,4,8a,9,10,11,12,12a-octahydro-2H-isochromeno[3,4-h]chromen-3-yl] 3,4,5-trihydroxybenzoate
—— [(2R,3R)-8-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate 1173162-12-3 C32H34O11
[(2R,3R)-8-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
—— 5,7-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene 333796-78-4 C50H42O6
5,7-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene
—— EGCG-MOx-D6 1309591-69-2 C44H34O23
EGCG-MOx-D6
—— Epigallocatechin gallate 3'-palmitate 948837-65-8 C38H48O12
Epigallocatechin gallate 3'-palmitate
—— (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yI 3,4-difluorobenzoate 1256160-12-9 C22H16F2O8
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yI 3,4-difluorobenzoate
—— dehydrotheasinensin C 894417-13-1 C30H26O15
dehydrotheasinensin C
—— epicatechin 3-O-gallate-(4β->6)-epigallocatechin 3-O-gallate 126715-91-1 C44H34O21
epicatechin 3-O-gallate-(4β->6)-epigallocatechin 3-O-gallate
—— (-)-3-O-methyl-apigallocatechin-3-O-(3,5-O-dimethyl)-gallate 1046425-79-9 C25H24O11
(-)-3-O-methyl-apigallocatechin-3-O-(3,5-O-dimethyl)-gallate
—— Quercetin 3-O-[2''-O-(6'''-O-p-coumaroyl)-b-D-glucopyranosyl]-a-L-rhamnopyranoside 113447-39-5 C36H36O18
Quercetin 3-O-[2''-O-(6'''-O-p-coumaroyl)-b-D-glucopyranosyl]-a-L-rhamnopyranoside
—— (2R,3R)-8-(((2R,3R)-6-(((2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-8-yl)methyl)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate 1208862-37-6 C68H54O33
(2R,3R)-8-(((2R,3R)-6-(((2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-8-yl)methyl)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
—— (-)-(2R,3R)-5,7-dihydroxy-2-(3',5'-dihydroxy-4'-methoxyphenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate 298700-58-0 C24H22O11
(-)-(2R,3R)-5,7-dihydroxy-2-(3',5'-dihydroxy-4'-methoxyphenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate
—— (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3,4,5-trimethoxybenzoate 873936-01-7 C30H34O11
(2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3,4,5-trimethoxybenzoate
—— (2R,3R)-8-(((2R,3R)-8-(((2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate 1208862-36-5 C68H54O33
(2R,3R)-8-(((2R,3R)-8-(((2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-6-yl)methyl)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate
—— Epigallocatechin gallate 4-palmitate 355120-39-7 C38H48O12
Epigallocatechin gallate 4-palmitate
—— oolong homobisflavan-tetramer-1 1208862-34-3 C91H72O44
oolong homobisflavan-tetramer-1
—— EGCG-stearate 1310571-13-1 C94H154O15
EGCG-stearate
—— (2R,2'R,3R,3'R)-8,8'-(2R,2'R,3R,3'R)-8,8'-methylenebis(5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-8,6-diyl)bis(methylene)bis(5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-8,3-diyl) bis(3,4,5-trihydroxybenzoate) 1208862-35-4 C91H72O44
(2R,2'R,3R,3'R)-8,8'-(2R,2'R,3R,3'R)-8,8'-methylenebis(5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)chroman-8,6-diyl)bis(methylene)bis(5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-8,3-diyl) bis(3,4,5-trihydroxybenzoate)
—— oolong homobisflavan C 126716-06-1 C45H36O22
oolong homobisflavan C