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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
—— N-[2-(4-hydroxy-3-nitrophenyl)-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl]acetamide 372101-97-8 C18H14N2O7
N-[2-(4-hydroxy-3-nitrophenyl)-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl]acetamide
—— 2-<4-(t-Pyyrolidinoethoxy)benzoyl>-3-methyl-7-phenyl-5H-furo<3,2-g><1>benzopyran-5-one 108142-02-5 C31H27NO5
2-<4-(t-Pyyrolidinoethoxy)benzoyl>-3-methyl-7-phenyl-5H-furo<3,2-g><1>benzopyran-5-one
—— 2-[2-(2,4-dihydroxyphenyl)-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl]-1λ6-isothiazolidin-1,1-dione 372102-58-4 C19H17NO7S
2-[2-(2,4-dihydroxyphenyl)-3-hydroxy-6-methyl-4-oxo-4H-chromen-8-yl]-1λ6-isothiazolidin-1,1-dione
—— 6-Chloro-3-nitro-2-phenyl-chroman-4-ol 96090-17-4 C15H12ClNO4
6-Chloro-3-nitro-2-phenyl-chroman-4-ol
—— (8S)-8-(4-chloro-2-methylphenyl)-5-[(3-methoxyazetidin-1-yl)-carbonyl]-2,3-dimethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole 1046469-12-8 C24H26ClN3O3
(8S)-8-(4-chloro-2-methylphenyl)-5-[(3-methoxyazetidin-1-yl)-carbonyl]-2,3-dimethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole
—— 2,3-trans-3,4-cis-4-phenoxyflavan-3-ol 35094-94-1 C21H18O3
2,3-trans-3,4-cis-4-phenoxyflavan-3-ol
—— 7-(acetoxymethyl)-5-amino-2-[4-(azidoacetamido)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one 468719-75-7 C20H14F3N5O5
7-(acetoxymethyl)-5-amino-2-[4-(azidoacetamido)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one
—— (2<i>R</i>)-5,7-diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-3<i>t</i>-(tri-<i>O</i>-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one 121707-94-6 C35H36O18
(2<i>R</i>)-5,7-diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-3<i>t</i>-(tri-<i>O</i>-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one
—— 9,9-difluoro-2-methoxymethoxy-6-(4-methoxymethoxy-phenyl)-6A,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene 787622-12-2 C23H26F2O5
9,9-difluoro-2-methoxymethoxy-6-(4-methoxymethoxy-phenyl)-6A,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
—— (S)2,8-dimethoxy-5-{4-[2-(1-piperydinyl)ethoxy]phenyl}-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene 554431-76-4 C32H35NO5
(S)2,8-dimethoxy-5-{4-[2-(1-piperydinyl)ethoxy]phenyl}-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene
—— 3-(benzenesulfonyl)-2-(4-methoxyphenyl)-6-methylchromen-4-one 87127-73-9 C23H18O5S
3-(benzenesulfonyl)-2-(4-methoxyphenyl)-6-methylchromen-4-one
—— 6-acetoxy-2-(4-acetoxy-phenyl)-3-bromo-5,7-dimethoxy-chroman-4-one 102478-41-1 C21H19BrO8
6-acetoxy-2-(4-acetoxy-phenyl)-3-bromo-5,7-dimethoxy-chroman-4-one
—— 2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-propionic acid 141070-66-8 C25H20O5
2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-propionic acid
—— Epiafzelechin-(4β->8,2β->O->7)-ent-afzelechin 143289-81-0 C30H24O10
Epiafzelechin-(4β->8,2β->O->7)-ent-afzelechin
—— 2-Methoxy-5-methyl-2-phenylbenzofuran-2H-3-on 63514-70-5 C16H14O3
2-Methoxy-5-methyl-2-phenylbenzofuran-2H-3-on
—— butyl 2-(10-fluoro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate 1609940-29-5 C22H19FO5
butyl 2-(10-fluoro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate
—— 2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-propionic acid methyl ester 141070-58-8 C26H22O5
2-(3-Benzyloxy-4-oxo-2-phenyl-4H-chromen-6-yl)-propionic acid methyl ester
—— 6-methoxy-2-phenyl-8-(2,4,6-trinitro-anilino)-chromen-4-one 102661-77-8 C22H14N4O9
6-methoxy-2-phenyl-8-(2,4,6-trinitro-anilino)-chromen-4-one
—— 7-benzoyloxy-3-methyl-2-phenyl-chromen-4-one 858258-32-9 C23H16O4
7-benzoyloxy-3-methyl-2-phenyl-chromen-4-one
—— 2-[4-Bis(2-chloroethyl)amino]phenyl-5-(N-pivaloyl)amino-4H-benzopyran-4-one 130599-64-3 C24H26Cl2N2O3
2-[4-Bis(2-chloroethyl)amino]phenyl-5-(N-pivaloyl)amino-4H-benzopyran-4-one
—— 5,7-Diacetoxy-2-(4-methoxy-phenyl)-6,8-dimethyl-chroman 102662-99-7 C22H24O6
5,7-Diacetoxy-2-(4-methoxy-phenyl)-6,8-dimethyl-chroman
—— (S)-2-[3,4-Dimethoxy-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-5,7-dimethoxy-chroman-4-one 78335-37-2 C25H30O12
(S)-2-[3,4-Dimethoxy-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-5,7-dimethoxy-chroman-4-one
—— 1-(2,6-dihydroxy-4-methoxy-phenyl)-3-(4-β-D-glucopyranosyloxy-phenyl)-propan-1-one 30819-58-0 C22H26O10
1-(2,6-dihydroxy-4-methoxy-phenyl)-3-(4-β-D-glucopyranosyloxy-phenyl)-propan-1-one
—— 2-Methyl-butyric acid 3,6-dimethoxy-2-(4-methoxy-phenyl)-4,5,8-trioxo-5,8-dihydro-4H-chromen-7-yl ester 142609-06-1 C23H22O9
2-Methyl-butyric acid 3,6-dimethoxy-2-(4-methoxy-phenyl)-4,5,8-trioxo-5,8-dihydro-4H-chromen-7-yl ester
—— (2-phenyl-chroman-2-yl)-methanol 61844-22-2 C16H16O2
(2-phenyl-chroman-2-yl)-methanol
—— (1-difluoromethoxy-6-(3-chlorophenyl)-6H-dibenzo(b,d)pyran-8-yl)-N,N-dimethylthiourea 373631-95-9 C23H19ClF2N2O2S
(1-difluoromethoxy-6-(3-chlorophenyl)-6H-dibenzo(b,d)pyran-8-yl)-N,N-dimethylthiourea
—— 3-iodo-5,7-dimethoxy-2-phenyl-chroman-4-one 101441-50-3 C17H15IO4
3-iodo-5,7-dimethoxy-2-phenyl-chroman-4-one
—— (1-methoxy-6-phenyl-6H-dibenzo(b,d)pyran-8-yl)-(2-phenyl-E-ethenyl) sulfonamide 373621-46-6 C28H23NO4S
(1-methoxy-6-phenyl-6H-dibenzo(b,d)pyran-8-yl)-(2-phenyl-E-ethenyl) sulfonamide
—— (19R)-19-[4-(2-piperidin-1-ylethoxy)phenyl]-8,18-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2,4,6,12(17),13,15-heptaen-15-ol 1157856-93-3 C30H31NO4
(19R)-19-[4-(2-piperidin-1-ylethoxy)phenyl]-8,18-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2,4,6,12(17),13,15-heptaen-15-ol
—— Chrysoeriol 7-neohesperidoside 111133-90-5 C28H32O15
Chrysoeriol 7-neohesperidoside
—— rac-2-(6-chloropyridin-3-yl)-2H-chromene-3-carboxylic acid 1204755-07-6 C15H10ClNO3
rac-2-(6-chloropyridin-3-yl)-2H-chromene-3-carboxylic acid
—— 8-(4-hydroxyphenyl)-2,2-dimethyl-3,4,7,8-tetrahydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one 415921-45-8 C20H20O4
8-(4-hydroxyphenyl)-2,2-dimethyl-3,4,7,8-tetrahydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
—— 2',5-dihydroxy-3',5',6,7-tetramethoxyflavone 93092-13-8 C19H18O8
2',5-dihydroxy-3',5',6,7-tetramethoxyflavone
—— 7-β-D-glucopyranosyloxy-3-methyl-2-phenyl-chromen-4-one 122272-07-5 C22H22O8
7-β-D-glucopyranosyloxy-3-methyl-2-phenyl-chromen-4-one
—— 2-phenyl-chroman-6-ylamine 111383-07-4 C15H15NO
2-phenyl-chroman-6-ylamine
—— 6-hydroxy-3,7-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 858801-52-2 C20H20O8
6-hydroxy-3,7-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
—— 7-acetoxy-3-methoxy-2-phenyl-8-propyl-chromen-4-one 102474-08-8 C21H20O5
7-acetoxy-3-methoxy-2-phenyl-8-propyl-chromen-4-one
—— 2-(2-benzyl-4-methoxyphenyl)-4H-chromen-4-one 1307886-94-7 C23H18O3
2-(2-benzyl-4-methoxyphenyl)-4H-chromen-4-one
—— 8-(tert-butyl)-2-phenyl-2H-chromene 1532560-31-8 C19H20O
8-(tert-butyl)-2-phenyl-2H-chromene
—— 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-4-oxo-4H-chromen-7-yl isobutyrate 1201808-20-9 C32H24O7
2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-4-oxo-4H-chromen-7-yl isobutyrate
—— rac-2-(naphthalen-1-yl)-2H-chromene-3-carboxylic acid 1204754-81-3 C20H14O3
rac-2-(naphthalen-1-yl)-2H-chromene-3-carboxylic acid
—— dorsilurin H 1094298-40-4 C30H34O7
dorsilurin H
—— 7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-(2-trifluoromethoxybenzylamino)-4H-chromen-4-one 1094471-25-6 C38H30F3NO6
7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-(2-trifluoromethoxybenzylamino)-4H-chromen-4-one
—— 6-Hydroxy-2-(4-methoxy-phenyl)-3,7-dimethyl-chromen-4-one 98231-00-6 C18H16O4
6-Hydroxy-2-(4-methoxy-phenyl)-3,7-dimethyl-chromen-4-one
—— [3-hydroxy-6,7-dimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)-4-oxochromen-5-yl] 4-methylbenzenesulfonate 124910-01-6 C32H28O10S
[3-hydroxy-6,7-dimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)-4-oxochromen-5-yl] 4-methylbenzenesulfonate
—— 2-[2,4-dioxo-5-[[3-(4-oxochromen-2-yl)phenyl]methylidene]-1,3-thiazolidin-3-yl]acetic acid 1062051-91-5 C21H13NO6S
2-[2,4-dioxo-5-[[3-(4-oxochromen-2-yl)phenyl]methylidene]-1,3-thiazolidin-3-yl]acetic acid
—— Quercetin-3-O-β-L-arabofuranosid-7-O-β-D-glucopyranosid 23394-51-6 C26H28O16
Quercetin-3-O-β-L-arabofuranosid-7-O-β-D-glucopyranosid
—— Parkinsonin-B 6980-22-9 C23H24O11
Parkinsonin-B
—— Acetic acid (2R,3R,4R,2'R,3'S)-2'-(3,4-dimethoxy-phenyl)-3,7,8,5',7'-pentamethoxy-2-(4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3'-yl ester 78139-54-5 C40H44O12
Acetic acid (2R,3R,4R,2'R,3'S)-2'-(3,4-dimethoxy-phenyl)-3,7,8,5',7'-pentamethoxy-2-(4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3'-yl ester
—— Acetic acid 3,6,7,8-tetramethoxy-2-(7-methoxy-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-5-yl ester 82669-00-9 C23H22O11
Acetic acid 3,6,7,8-tetramethoxy-2-(7-methoxy-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-5-yl ester