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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
—— 3,5,7,3',4'-pentamethoxyflav-3-ene 16820-97-6 C20H22O6
3,5,7,3',4'-pentamethoxyflav-3-ene
—— (2R,3S)-2-(2,2,4,4-tetraisopropylbenzo[f][1,3,5,2,4]trioxadisilepin-7-yl)chroman-3,5,7-triol 1304014-12-7 C27H40O7Si2
(2R,3S)-2-(2,2,4,4-tetraisopropylbenzo[f][1,3,5,2,4]trioxadisilepin-7-yl)chroman-3,5,7-triol
—— 3,3',4',7-tetra-O-cinnamoylpatuletin 1067670-15-8 C52H36O12
3,3',4',7-tetra-O-cinnamoylpatuletin
—— Dimethyl flavonyl-7-oxyfumarate 95094-99-8 C21H16O7
Dimethyl flavonyl-7-oxyfumarate
—— tri-tert-butyl ((2R,3S)-2-(3-fluoro-4-hydroxyphenyl)chromane-3,5,7-triyl) tricarbonate 1256550-78-3 C30H37FO11
tri-tert-butyl ((2R,3S)-2-(3-fluoro-4-hydroxyphenyl)chromane-3,5,7-triyl) tricarbonate
—— [3-[3-[4-[4-[[5-(3,7-Dihydroxy-5-methoxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]methyl]triazol-1-yl]butyl]-4-oxoquinazolin-2-yl]-5-hydroxyphenyl] acetate 1427579-83-6 C39H33N5O11
[3-[3-[4-[4-[[5-(3,7-Dihydroxy-5-methoxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]methyl]triazol-1-yl]butyl]-4-oxoquinazolin-2-yl]-5-hydroxyphenyl] acetate
—— 3-O-acetyl-6-iodo-3',4',5,7-tetra-O-methyl-(+)-catechin 104079-74-5 C21H23IO7
3-O-acetyl-6-iodo-3',4',5,7-tetra-O-methyl-(+)-catechin
—— 88204-07-3 C63H68O21
—— 1364301-33-6 C27H38O8S2
—— (Z)-3-(((2-methylbenzyl)amino)methylene)-2-(o-tolyl)chroman-4-one 1430097-97-4 C25H23NO2
(Z)-3-(((2-methylbenzyl)amino)methylene)-2-(o-tolyl)chroman-4-one
—— 8-methoxycarbonyl-3',4',5,7-tetra-O-methyl-(+)-catechin 69119-57-9 C21H24O8
8-methoxycarbonyl-3',4',5,7-tetra-O-methyl-(+)-catechin
—— (2R<sup>*</sup>,3S<sup>*</sup>,4S<sup>*</sup>)-5,4'-dimethoxyflavan-3,4-diol 86788-66-1 C17H18O5
(2R<sup>*</sup>,3S<sup>*</sup>,4S<sup>*</sup>)-5,4'-dimethoxyflavan-3,4-diol
—— 4'-benzyloxy-3-hydroxy-3',5,7,8-tetramethoxyflavone 116512-04-0 C26H24O8
4'-benzyloxy-3-hydroxy-3',5,7,8-tetramethoxyflavone
—— 2-(4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenyl)-6,8-dichloro-4H-chromen-4-one 1451740-19-4 C21H19Cl2N3O5
2-(4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenyl)-6,8-dichloro-4H-chromen-4-one
—— methyl 2-fluoro-5-((2S,4S)-2-(3-(((R)-1-(naphthalen-1-yl)ethyl)amino)propyl)chroman-4-yl)benzoate 1451372-82-9 C32H32FNO3
methyl 2-fluoro-5-((2S,4S)-2-(3-(((R)-1-(naphthalen-1-yl)ethyl)amino)propyl)chroman-4-yl)benzoate
—— 5,3',4'-tri-O-methyl-(+)-catechin 29127-26-2 C18H20O6
5,3',4'-tri-O-methyl-(+)-catechin
—— 1400698-22-7 C15H6Cl2F2O2
—— 7-(2-{1-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxopropylidene}hydrazinyl)-2-phenyl-4H-chromen-4-one 1394154-47-2 C28H25ClN4O3
7-(2-{1-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxopropylidene}hydrazinyl)-2-phenyl-4H-chromen-4-one
—— 6-fluoro-2-(4-(methylthio)phenyl)-4H-1-benzopyran-4-one 259681-74-8 C16H11FO2S
6-fluoro-2-(4-(methylthio)phenyl)-4H-1-benzopyran-4-one
—— 2-[(3S,4S)-4-[(2R,3S)-2-(3,4-Dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-6-yl]-5,6,7-trimethoxy-1-oxo-3-((1S,2R,3R)-1,2,3,4-tetrahydroxy-butyl)-isochroman-8-yl]-3,4,5-trimethoxy-benzoic acid methyl ester 97775-95-6 C46H54O20
2-[(3S,4S)-4-[(2R,3S)-2-(3,4-Dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-6-yl]-5,6,7-trimethoxy-1-oxo-3-((1S,2R,3R)-1,2,3,4-tetrahydroxy-butyl)-isochroman-8-yl]-3,4,5-trimethoxy-benzoic acid methyl ester
—— (2R,2'R,2''R,2'''R,3S,3'S,3''S,3'''S,4S,4'S,4''R)-2,2',2'',2'''-tetrakis(3,4-dimethoxyphenyl)-5,5',5'',5''',7,7',7'',7'''-octamethoxy-[4,8':4',8'':4'',8'''-quaterchromane]-3,3',3'',3'''-tetrayl tetraacetate 88204-08-4 C84H90O28
(2R,2'R,2''R,2'''R,3S,3'S,3''S,3'''S,4S,4'S,4''R)-2,2',2'',2'''-tetrakis(3,4-dimethoxyphenyl)-5,5',5'',5''',7,7',7'',7'''-octamethoxy-[4,8':4',8'':4'',8'''-quaterchromane]-3,3',3'',3'''-tetrayl tetraacetate
—— 1-benzyl-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzimidazol-2-amine 1338824-84-2 C29H24N4O
1-benzyl-N-[(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]benzimidazol-2-amine
—— (3R,4S,2'R,3'S)-2'-(3,4-Dihydroxy-phenyl)-3-(2-hydroxy-4-methoxy-phenyl)-7-methoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3',5',7'-triol 95568-70-0 C32H30O10
(3R,4S,2'R,3'S)-2'-(3,4-Dihydroxy-phenyl)-3-(2-hydroxy-4-methoxy-phenyl)-7-methoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3',5',7'-triol
—— 4'-Hydroxy-3',5,7-trimethoxy-flavyliumchlorid 89475-35-4 C18H17O5*Cl
4'-Hydroxy-3',5,7-trimethoxy-flavyliumchlorid
—— 3-O-benzyl-6-hydroxy-3',4',5,7-tetra-O-methyl-(+)-catechin 69119-44-4 C26H28O7
3-O-benzyl-6-hydroxy-3',4',5,7-tetra-O-methyl-(+)-catechin
—— 6-ethyl-4-methyl-8-naphthalen-1-yl-pyrano[2,3-<i>f</i>]chromene-2,10-dione 32922-32-0 C25H18O4
6-ethyl-4-methyl-8-naphthalen-1-yl-pyrano[2,3-<i>f</i>]chromene-2,10-dione
—— 3,5,7,3',4'-penta-O-benzyl-8-carboxycatechin 89385-96-6 C51H44O8
3,5,7,3',4'-penta-O-benzyl-8-carboxycatechin
—— 2-(4-O-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one 1313191-85-3 C49H44O12
2-(4-O-β-D-glucopyranosyloxy-3-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one
—— 3,5,7,3',4'-penta-O-methylcyanidin 47492-60-4 C20H21O6
3,5,7,3',4'-penta-O-methylcyanidin
—— 4-[(4-oxo-4H-1-benzopyran-2-phenyl-7-yl)oxy]butyric acid 301206-23-5 C19H16O5
4-[(4-oxo-4H-1-benzopyran-2-phenyl-7-yl)oxy]butyric acid
—— (2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',7-tetramethoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7-trimethoxyflavan-6-yl>flavan 78139-49-8 C39H42O11
(2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',7-tetramethoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7-trimethoxyflavan-6-yl>flavan
—— (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-ol 850816-18-1 C68H70O8
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-ol
—— (2R)-2r-(3,4-bis-methanesulfonyloxy-phenyl)-3t,5,7-tris-methanesulfonyloxy-chroman 111355-90-9 C20H24O16S5
(2R)-2r-(3,4-bis-methanesulfonyloxy-phenyl)-3t,5,7-tris-methanesulfonyloxy-chroman
—— 3'-methoxy-4',7-dihydroxyflavylium chloride 4082-07-9 C16H13O4*Cl
3'-methoxy-4',7-dihydroxyflavylium chloride
—— 4'-Hydroxy-3',7-dimethoxy-flavyliumchlorid 89475-34-3 C17H15O4*Cl
4'-Hydroxy-3',7-dimethoxy-flavyliumchlorid
—— 1312298-07-9 C25H22O8
—— 2,8-bis-(4-methoxy-phenyl)-pyrano[2,3-<i>f</i>]chromene-4,10-dione 72758-06-6 C26H18O6
2,8-bis-(4-methoxy-phenyl)-pyrano[2,3-<i>f</i>]chromene-4,10-dione
—— 5-methoxycarbonyl-3,3-(4,4'-difluorophenyl)-3H-naphtho[2,1-b]pyrane 853305-74-5 C27H18F2O3
5-methoxycarbonyl-3,3-(4,4'-difluorophenyl)-3H-naphtho[2,1-b]pyrane
—— 3'-<8-(3,4-dihydroxyphenyl)-7-hydroxy-2,4,9-trioxobicyclo-<3.3.1>nonan-6-yl>-4-(3,4-dihydroxyphenyl)-2',3,4',5,6',7-hexahydroxy flavan 113638-69-0 C36H30O15
3'-<8-(3,4-dihydroxyphenyl)-7-hydroxy-2,4,9-trioxobicyclo-<3.3.1>nonan-6-yl>-4-(3,4-dihydroxyphenyl)-2',3,4',5,6',7-hexahydroxy flavan
—— naringenin 7-O-(2-O-α-L-fucopyranosyl-β-D-galactopyranoside) 88294-40-0 C27H32O14
naringenin 7-O-(2-O-α-L-fucopyranosyl-β-D-galactopyranoside)
—— (2R,3S)-2-(3,4-dihydroxyphenyl)-6-(((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-6-yl)(4-hydroxy-3-methoxyphenyl)methyl)-8-(((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)(4-hydroxy-3-methoxyphenyl)methyl)chromane-3,5,7-triol 1007363-66-7 C61H54O22
(2R,3S)-2-(3,4-dihydroxyphenyl)-6-(((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-6-yl)(4-hydroxy-3-methoxyphenyl)methyl)-8-(((2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)(4-hydroxy-3-methoxyphenyl)methyl)chromane-3,5,7-triol
—— (2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-phenyloxoacetyloxy-chroman 115760-12-8 C27H26O8
(2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-phenyloxoacetyloxy-chroman
—— 3-(3,4-dihydroxy-phenyl)-2-(2,4,6-trihydroxy-benzyl)-2,3-dihydro-benzofuran-4,6-diol 100169-44-6 C21H18O8
3-(3,4-dihydroxy-phenyl)-2-(2,4,6-trihydroxy-benzyl)-2,3-dihydro-benzofuran-4,6-diol
—— (+-)-3t,4c-Bis-(4-nitro-benzoyloxy)-2r-phenyl-chroman 103165-66-8 C29H20N2O9
(+-)-3t,4c-Bis-(4-nitro-benzoyloxy)-2r-phenyl-chroman
—— 2-(3,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-8-methyl-chromen-4-one 116194-53-7 C19H18O6
2-(3,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-8-methyl-chromen-4-one
—— 4'-O-[CO-Lys(Boc)-OtBu]-quercetin 1138406-11-7 C31H38N2O12
4'-O-[CO-Lys(Boc)-OtBu]-quercetin
—— (R)-8-Allyl-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-one 919365-55-2 C46H40O6
(R)-8-Allyl-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-one
—— 2-(3,4-dimethoxyphenyl)-2-methylchromane 1449790-09-3 C18H20O3
2-(3,4-dimethoxyphenyl)-2-methylchromane
—— 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone 749256-78-8 C54H44O16
5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone
—— 2''-(Phenylflavano)(7,8:6'',5'')pyran-4''-on 72757-99-4 C24H18O4
2''-(Phenylflavano)(7,8:6'',5'')pyran-4''-on