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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
—— (2S,3R,4S)-2-(4-Hydroxy-phenyl)-4-methoxy-chroman-3,5-diol 101946-99-0 C16H16O5
(2S,3R,4S)-2-(4-Hydroxy-phenyl)-4-methoxy-chroman-3,5-diol
—— (2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1r,4R)-4-fluorocyclohexane-1-carboxylate 1608504-44-4 C50H47FO7
(2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl (1r,4R)-4-fluorocyclohexane-1-carboxylate
—— (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 109671-64-9 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
—— 3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 1313191-76-2 C57H52O16
3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one
—— 4-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester 728935-44-2 C31H35N3O5
4-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester
—— 7,2',4'-Trimethoxy-5'-benzoylflavon 33427-56-4 C25H20O6
7,2',4'-Trimethoxy-5'-benzoylflavon
—— ethyl 8-methyl-7-oxo-10-phenyl-7a,8,9,10-tetrahydronaphtho[1,2-b]chromene-9-carboxylate 135978-95-9 C27H24O4
ethyl 8-methyl-7-oxo-10-phenyl-7a,8,9,10-tetrahydronaphtho[1,2-b]chromene-9-carboxylate
—— 4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(2-((tert-butoxycarbonyl)amino)acetate) 1609067-52-8 C29H32N2O10
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(2-((tert-butoxycarbonyl)amino)acetate)
—— 2,2-dioxo-5-phenyl-5H-chromeno[3,4-e]oxathiazin-4-one 116215-63-5 C16H11NO5S
2,2-dioxo-5-phenyl-5H-chromeno[3,4-e]oxathiazin-4-one
—— methyl 4-oxo-2-phenyl-2,3-dihydrochromene-3-carboxylate 1417564-38-5 C17H14O4
methyl 4-oxo-2-phenyl-2,3-dihydrochromene-3-carboxylate
—— (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid butyl ester 27654-57-5 C21H20O5
(4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid butyl ester
—— 6-((4-methoxyphenyl)amino)-2-phenyl-4H-chromen-4-one 1644565-51-4 C22H17NO3
6-((4-methoxyphenyl)amino)-2-phenyl-4H-chromen-4-one
—— 8-Benzo[1,3]dioxol-5-yl-5,9-dimethoxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-10-one 89024-08-8 C23H22O7
8-Benzo[1,3]dioxol-5-yl-5,9-dimethoxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-10-one
—— 3-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]propanoic acid 89385-46-6 C18H18O8
3-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]propanoic acid
—— (2R,3S,4S,2'R,3'S)-2'-(3,4-Dimethoxy-phenyl)-7,5',7'-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol 15868-45-8 C38H42O12
(2R,3S,4S,2'R,3'S)-2'-(3,4-Dimethoxy-phenyl)-7,5',7'-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol
—— 6-iodotetra-O-methyl-(+)-catechin 117820-44-7 C19H21IO6
6-iodotetra-O-methyl-(+)-catechin
—— 5-hydroxy-3'-methoxy-4',7-di[(2-methoxyethoxy)methoxy]flavone 1456788-26-3 C24H28O10
5-hydroxy-3'-methoxy-4',7-di[(2-methoxyethoxy)methoxy]flavone
—— 2-[4-(N-morpholinyl)phenyl]-2-phenyl-5,6,7, 8-tetrahydro-5-oxo-phenanthro[9,10-b]pyran 252901-79-4 C33H29NO3
2-[4-(N-morpholinyl)phenyl]-2-phenyl-5,6,7, 8-tetrahydro-5-oxo-phenanthro[9,10-b]pyran
—— 5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10,11-bis(methylsulfanyl)-18-(trifluoromethyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaene-21,3'-cyclohexane] 1263318-51-9 C46H45F3O3S2
5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10,11-bis(methylsulfanyl)-18-(trifluoromethyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15(20),16,18-nonaene-21,3'-cyclohexane]
—— 4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]-10-yl]morpholine 1263318-31-5 C48H51NO4S
4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]-10-yl]morpholine
—— 7-Hydroxy-8-cinnamoylflavon 72758-01-1 C24H16O4
7-Hydroxy-8-cinnamoylflavon
—— (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 1313191-83-1 C43H40O16
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
—— 10-(2,4-Dimethoxyphenyl)-11-methoxy-1',1',5',5'-tetramethyl-5,5-bis(4-propoxyphenyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane] 1278524-10-9 C56H60O6
10-(2,4-Dimethoxyphenyl)-11-methoxy-1',1',5',5'-tetramethyl-5,5-bis(4-propoxyphenyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]
—— 3'-O-(CO-Met-OtBu)-quercetin 1138406-44-6 C25H27NO10S
3'-O-(CO-Met-OtBu)-quercetin
—— 4-methoxy-6-(4-methylphenyl)-6,12-methano-12H-dibenzo[d,g][1,3]dioxocin 1429327-16-1 C23H20O3
4-methoxy-6-(4-methylphenyl)-6,12-methano-12H-dibenzo[d,g][1,3]dioxocin
—— 3',4',6-Trichlorflavon 36768-58-8 C15H7Cl3O2
3',4',6-Trichlorflavon
—— prop-2-en-1-yl 4-oxo-2-phenyl-4H-chromene-3-carboxylate 1607814-67-4 C19H14O4
prop-2-en-1-yl 4-oxo-2-phenyl-4H-chromene-3-carboxylate
—— 6-chloro-2-(4-methylphenyl)-2H-chromene 1413850-54-0 C16H13ClO
6-chloro-2-(4-methylphenyl)-2H-chromene
—— [4,6-dimethoxy-1-(4-methoxyphenyl)-9,16-dioxo-8-(4-oxocyclohexa-2,5-dien-1-ylidene)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaen-12-yl] acetate 1164114-80-0 C33H24O9
[4,6-dimethoxy-1-(4-methoxyphenyl)-9,16-dioxo-8-(4-oxocyclohexa-2,5-dien-1-ylidene)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaen-12-yl] acetate
—— (2R*,3R*)-5,4'-dihydroxyflavanonol 86788-65-0 C15H12O5
(2R*,3R*)-5,4'-dihydroxyflavanonol
—— 4'-O-[CO-Glu(OtBu)-OtBu]-quercetin 1138406-16-2 C29H33NO12
4'-O-[CO-Glu(OtBu)-OtBu]-quercetin
—— 2-(4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one 1313191-84-2 C57H52O16
2-(4-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one
—— 3-O-benzyl-6,8-dibromo-3',4',5,7-tetra-O-methyl-(+)-catechin 69119-42-2 C26H26Br2O6
3-O-benzyl-6,8-dibromo-3',4',5,7-tetra-O-methyl-(+)-catechin
—— 5-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin 345319-78-0 C27H34O16
5-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin
—— 3,7-bis-benzyloxy-2-[4-benzyloxy-3-(3-(2,6-cis-dimethylmorpholin-4-yl)-2-hydroxy-propoxy)phenyl]-5-hydroxy-chromen-4-one 1383562-25-1 C45H45NO9
3,7-bis-benzyloxy-2-[4-benzyloxy-3-(3-(2,6-cis-dimethylmorpholin-4-yl)-2-hydroxy-propoxy)phenyl]-5-hydroxy-chromen-4-one
—— 3-(cis-4'-methoxyflavan-4β-yloxy)flavone 88233-68-5 C31H24O5
3-(cis-4'-methoxyflavan-4β-yloxy)flavone
—— 2-(3,4-Bis-benzyloxy-phenyl)-3-butyl-5,6,7-trimethoxy-chromen-4-one 134082-17-0 C36H36O7
2-(3,4-Bis-benzyloxy-phenyl)-3-butyl-5,6,7-trimethoxy-chromen-4-one
—— tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,6)-tetra-O-methyl-3-O-acetyl-(+)-taxifolin 117508-36-8 C41H42O14
tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,6)-tetra-O-methyl-3-O-acetyl-(+)-taxifolin
—— (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid propyl ester 27654-55-3 C20H18O5
(4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid propyl ester
—— 4,5,8,8,11,11,14,15-octamethyl-10,10-diphenyl-9-oxa-8,11-disilatricyclo[10.4.0.02,7]hexadeca-1(12),2(7),3,5,13,15-hexaene 114142-65-3 C33H38OSi2
4,5,8,8,11,11,14,15-octamethyl-10,10-diphenyl-9-oxa-8,11-disilatricyclo[10.4.0.02,7]hexadeca-1(12),2(7),3,5,13,15-hexaene
—— 7-((4-bromobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate 1254040-81-7 C26H19BrO7
7-((4-bromobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate
—— [3-hydroxy-6,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)-4-oxochromen-5-yl] 4-methylbenzenesulfonate 124910-00-5 C32H28O10S
[3-hydroxy-6,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)-4-oxochromen-5-yl] 4-methylbenzenesulfonate
—— 7-Hydroxy-2-methyl-isoflavanon 98090-19-8 C16H14O3
7-Hydroxy-2-methyl-isoflavanon
—— 1-{3-[4-amino-5-(2-phenyl-chroman-7-yl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-piperidin-4-ol 1309652-57-0 C31H35N5O2
1-{3-[4-amino-5-(2-phenyl-chroman-7-yl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-piperidin-4-ol
—— 3-methoxy-4-oxo-2-phenyl-4H-furo[2,3-h]chromene-8-carboxylic acid 109504-10-1 C19H12O6
3-methoxy-4-oxo-2-phenyl-4H-furo[2,3-h]chromene-8-carboxylic acid
—— (2R,3S,4S)-4-(phenylthio)-2-(3,4,5-trihydroxyphenyl)chromane-3,5,7-triol 402492-44-8 C21H18O7S
(2R,3S,4S)-4-(phenylthio)-2-(3,4,5-trihydroxyphenyl)chromane-3,5,7-triol
—— 4'-O-(CO-Ala-OtBu)-quercetin 1138406-08-2 C23H23NO10
4'-O-(CO-Ala-OtBu)-quercetin
—— 1453812-70-8 C15H9BrO3
—— 2,3-dihydro-2-(4-ethoxyphenyl)-4H-benzopyran-4-one oxime 71906-95-1 C17H17NO3
2,3-dihydro-2-(4-ethoxyphenyl)-4H-benzopyran-4-one oxime
—— 3'-O-(CO-Met-OH)-quercetin 1138406-37-7 C24H22N2O13
3'-O-(CO-Met-OH)-quercetin