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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
—— (R)-2-(4-fluorophenyl)chroman-4-one 1413433-48-3 C15H11FO2
(R)-2-(4-fluorophenyl)chroman-4-one
—— tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4β,6)-penta-O-methyl-3-O-acetyl-(+)-ampelopsin 117558-26-6 C42H44O15
tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4β,6)-penta-O-methyl-3-O-acetyl-(+)-ampelopsin
—— 2,4-Dimethyl-6-(2,6,8-trimethyl-2-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-4-yl)-phenol 76080-50-7 C25H27NO2
2,4-Dimethyl-6-(2,6,8-trimethyl-2-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-4-yl)-phenol
—— 2-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromen-4-one 955880-05-4 C21H21BO4
2-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromen-4-one
—— 8-(Bromomethyl)-2-(4-chlorophenyl)chromen-4-one 87165-57-9 C16H10BrClO2
8-(Bromomethyl)-2-(4-chlorophenyl)chromen-4-one
—— 2-(4-methoxyphenyl)-3-(phenylselanyl)-4H-chromen-4-one 1332698-03-9 C22H16O3Se
2-(4-methoxyphenyl)-3-(phenylselanyl)-4H-chromen-4-one
—— 5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-methylsulfanyl-11-(trifluoromethylsulfanyl)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] 1263318-03-1 C45H43F3O3S2
5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-methylsulfanyl-11-(trifluoromethylsulfanyl)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]
—— 7-allyloxy-3-methoxy-2-phenyl-chromen-4-one 15068-34-5 C19H16O4
7-allyloxy-3-methoxy-2-phenyl-chromen-4-one
—— 5,5''-Diacetoxy-4',4''',7,7''-tetra-O-methylcupressuflavon 63043-63-0 C38H30O12
5,5''-Diacetoxy-4',4''',7,7''-tetra-O-methylcupressuflavon
—— 1466397-29-4 C37H35NO10
—— 5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-(4'',6''-O-isopropylidene)glucosyl-4H-chromen-4-one 1246840-48-1 C51H44O12
5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-(4'',6''-O-isopropylidene)glucosyl-4H-chromen-4-one
—— 6,2',6'-Trihydroxy-flavon 24457-37-2 C15H10O5
6,2',6'-Trihydroxy-flavon
—— 1466397-25-0 C20H17NO10
—— 9-(4-oxo-4H-1-benzopyran-2-yl)-5-chlorotetrazolo[4,3-a]quinoline 1333215-86-3 C18H9ClN4O2
9-(4-oxo-4H-1-benzopyran-2-yl)-5-chlorotetrazolo[4,3-a]quinoline
—— trans-(2R,3S)-3-acetoxy-4'-hydroxyflavan 1196870-75-3 C17H16O4
trans-(2R,3S)-3-acetoxy-4'-hydroxyflavan
—— 4'-methoxy-7-hydroxy-3,6-diacetyl flavone 261167-23-1 C20H16O6
4'-methoxy-7-hydroxy-3,6-diacetyl flavone
—— acetic acid 5-acetoxy-7-hydroxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-3-yl ester 1258551-29-9 C32H22O9
acetic acid 5-acetoxy-7-hydroxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-3-yl ester
—— 5,5-Bis(4-methoxyphenyl)-10,11-bis(methylsulfanyl)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-21,2'-bicyclo[2.2.1]heptane] 1263318-49-5 C42H38O3S2
5,5-Bis(4-methoxyphenyl)-10,11-bis(methylsulfanyl)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-21,2'-bicyclo[2.2.1]heptane]
—— 5-(((2R,3S,4S,5R,6S)-3,4-Dihydroxy-6-(5-hydroxy-2-(4-hydroxyphenyl)-4-oxochroman-7-yl)-5-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-3-hydroxy-3-methyl-5-oxopentanoic Acid 1162664-58-5 C33H40O17
5-(((2R,3S,4S,5R,6S)-3,4-Dihydroxy-6-(5-hydroxy-2-(4-hydroxyphenyl)-4-oxochroman-7-yl)-5-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)-3-hydroxy-3-methyl-5-oxopentanoic Acid
—— 1-(7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl)10-methyl decanedioate 1469894-78-7 C47H46O10
1-(7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl)10-methyl decanedioate
—— 3'-O-[CO-Lys(Boc)-OtBu]-quercetin 1138406-40-2 C31H38N2O12
3'-O-[CO-Lys(Boc)-OtBu]-quercetin
—— 3-[(furan-2-yl)carbonyl]-2-phenyl-4H-chromen-4-one 65485-36-1 C20H12O4
3-[(furan-2-yl)carbonyl]-2-phenyl-4H-chromen-4-one
—— (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 1096656-85-7 C31H32O14
(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
—— 2,3-dihydro-2-(3-nitrophenyl)-4H-1-benzopyran-4-one 127089-55-8 C15H11NO4
2,3-dihydro-2-(3-nitrophenyl)-4H-1-benzopyran-4-one
—— rivularin 2'-O-β-D-glucopyranoside 118525-38-5 C24H26O12
rivularin 2'-O-β-D-glucopyranoside
—— Acetic acid (2S,3R,4S,5S)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester 742062-22-2 C39H32O14
Acetic acid (2S,3R,4S,5S)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester
—— 5-(allyloxy)-2-(3,4-diacetoxyphenyl)-4-oxo-4H-chromene-3,7-diyl diacetate 1000841-75-7 C26H22O11
5-(allyloxy)-2-(3,4-diacetoxyphenyl)-4-oxo-4H-chromene-3,7-diyl diacetate
—— 7-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]-chroman-4-one 39953-46-3 C33H42O15
7-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2-[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]-chroman-4-one
—— 3',5-dihydroxy-4'-methoxy-7-(2-methoxy-3-carbethoxyprop-2-enyloxy)flavanone 76799-50-3 C23H24O9
3',5-dihydroxy-4'-methoxy-7-(2-methoxy-3-carbethoxyprop-2-enyloxy)flavanone
—— 5,4'-bis(chloroacetamido)-7-methyl-6,8,3'-trifluoro-4H-1-benzopyran-4-one 468719-73-5 C20H13Cl2F3N2O4
5,4'-bis(chloroacetamido)-7-methyl-6,8,3'-trifluoro-4H-1-benzopyran-4-one
—— 31643-84-2 C37H32O10
—— monopotassium mono(5-hydroxy-2-(3-hydroxy-4-(sulfonatooxy)phenyl)-4-oxo-4H-chromene-3,7-diyl bis(sulfate)) 116097-14-4 C15H7O16S3*3K
monopotassium mono(5-hydroxy-2-(3-hydroxy-4-(sulfonatooxy)phenyl)-4-oxo-4H-chromene-3,7-diyl bis(sulfate))
—— 1-(2,6-dichlorophenyl)-3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one 1529772-94-8 C42H30Cl2N2O5
1-(2,6-dichlorophenyl)-3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one
—— 2,3-cis-3,4-cis-3',4',5,7-tetramethoxy-2-(2,3-trans-3',4',5,7-tetramethoxyflavan-3-yloxy)flavan-3,4-diol 95731-55-8 C38H42O13
2,3-cis-3,4-cis-3',4',5,7-tetramethoxy-2-(2,3-trans-3',4',5,7-tetramethoxyflavan-3-yloxy)flavan-3,4-diol
—— (S)-2-Phenyl-3-[1-phenyl-meth-(E)-ylidene]-chroman-4-one 19041-35-1 C22H16O2
(S)-2-Phenyl-3-[1-phenyl-meth-(E)-ylidene]-chroman-4-one
—— 2-(3,4-dilinoleoyloxyphenyl)-4-oxo-4H-chromene-3,5-dihydroxy-7-linoleate 1515926-71-2 C69H100O10
2-(3,4-dilinoleoyloxyphenyl)-4-oxo-4H-chromene-3,5-dihydroxy-7-linoleate
—— 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-((3-nitrobenzyl)oxy)-4H-chromen-4-one 1394914-36-3 C22H15NO9
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-((3-nitrobenzyl)oxy)-4H-chromen-4-one
—— 79907-46-3 C72H62O34
—— 6-Acetamido-3-methyl-3',4',5'-trimethoxyflavon 36773-34-9 C21H21NO6
6-Acetamido-3-methyl-3',4',5'-trimethoxyflavon
—— 7-Hydroxy-8-benzoylflavon-oxim 37042-37-8 C22H15NO4
7-Hydroxy-8-benzoylflavon-oxim
—— 1442655-87-9 C58H66N4O15S
—— 2-(3-(2-(benzyloxy)-5-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy)propyl)isoindoline-1,3-dione 1355333-74-2 C47H37NO9
2-(3-(2-(benzyloxy)-5-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy)propyl)isoindoline-1,3-dione
—— 8-bromo-5,7,3',4'-tetramethoxyflavanone 94303-57-8 C19H19BrO6
8-bromo-5,7,3',4'-tetramethoxyflavanone
—— 3,5-di-O-acetyl-7-O-allylkaempferol 1307876-13-6 C22H18O8
3,5-di-O-acetyl-7-O-allylkaempferol
—— 1-(3-chlorophenyl)-3-[[2-(4-oxo-2-phenylchromen-7-yl)oxyacetyl]amino]thiourea 113495-02-6 C24H18ClN3O4S
1-(3-chlorophenyl)-3-[[2-(4-oxo-2-phenylchromen-7-yl)oxyacetyl]amino]thiourea
—— (E)-3-cinnamoyl-2-phenyl-4H-chromen-4-one 1312417-25-6 C24H16O3
(E)-3-cinnamoyl-2-phenyl-4H-chromen-4-one
—— Dihydroflavanol-semicarbazon 94460-26-1 C16H15N3O3
Dihydroflavanol-semicarbazon
—— 7-[2-(4-methoxy-phenyl)-2-oxo-ethoxy]-2-phenyl-chromen-4-one 88856-45-5 C24H18O5
7-[2-(4-methoxy-phenyl)-2-oxo-ethoxy]-2-phenyl-chromen-4-one
—— 5,7-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-6-(3-methyl-but-2-enyl)-chromen-4-one 55929-03-8 C22H22O6
5,7-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-6-(3-methyl-but-2-enyl)-chromen-4-one
—— 1403357-07-2 C20H17ClO3