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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
—— (S)-6-chloro-8-((2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one 1621457-93-9 C23H23ClN2O7
(S)-6-chloro-8-((2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one
—— (2R,3R,4S,2'R,3'S)-4-(3,4-Dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol 128428-27-3 C31H28O12
(2R,3R,4S,2'R,3'S)-4-(3,4-Dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol
—— 6-acetyl-7,8-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran 92215-47-9 C17H16O4
6-acetyl-7,8-dihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran
—— 2-phenyl-3-hydroxylamino-2H-1-benzopyran 112513-94-7 C15H15NO2
2-phenyl-3-hydroxylamino-2H-1-benzopyran
—— (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((3-(3-(3,4-dichlorophenyl)-3-oxoprop-1-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 1224255-76-8 C32H28Cl2O13
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((3-(3-(3,4-dichlorophenyl)-3-oxoprop-1-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
—— N-[4-(3-bromo-6-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide 145665-88-9 C18H13BrN2O5
N-[4-(3-bromo-6-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide
—— (2R,4R)-4-(4-Methoxy-phenyl)-2,4-dimethyl-chroman 64681-44-3 C18H20O2
(2R,4R)-4-(4-Methoxy-phenyl)-2,4-dimethyl-chroman
—— 4,4-diphenyl-4,4a-dihydro-2<i>H</i>-chromeno[3,2-<i>c</i>]pyridine-3,10-dione 70611-83-5 C24H17NO3
4,4-diphenyl-4,4a-dihydro-2<i>H</i>-chromeno[3,2-<i>c</i>]pyridine-3,10-dione
—— 3,4',7-Trimethoxy-5-hydroxy-6-formyl-flavon 108368-51-0 C19H16O7
3,4',7-Trimethoxy-5-hydroxy-6-formyl-flavon
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-chlorophenyl)prop-2-enoate 217661-71-7 C41H44ClO21
[(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-chlorophenyl)prop-2-enoate
—— broussoflavonol A triacetate 99217-71-7 C32H32O10
broussoflavonol A triacetate
—— 3,8-Dimethoxy-5,7,3',4'-tetraaethoxy-flav-4-on 4693-90-7 C25H30O8
3,8-Dimethoxy-5,7,3',4'-tetraaethoxy-flav-4-on
—— 2-(4-bromophenyl)-3-nitro-2H-chromene 1227402-03-0 C15H10BrNO3
2-(4-bromophenyl)-3-nitro-2H-chromene
—— 2-(3-hydroxyphenyl)chroman-6-ol 488849-14-5 C15H14O3
2-(3-hydroxyphenyl)chroman-6-ol
—— procyanidin B-3 4-O(E)-monomethyl ether 128428-19-3 C31H28O12
procyanidin B-3 4-O(E)-monomethyl ether
—— 4'-Benzyloxy-5-hydroxy-3',7-dimethoxy-flavon-3-O-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid 83332-33-6 C42H50O20
4'-Benzyloxy-5-hydroxy-3',7-dimethoxy-flavon-3-O-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid
—— (+/-)-6'-Phenylsulfonyl-catechin 14453-53-3 C21H18O8S
(+/-)-6'-Phenylsulfonyl-catechin
—— (<i>S</i>)-7-β-D-glucopyranosyloxy-5-methoxy-2-(4-methoxy-phenyl)-chroman-4-one 59942-61-9 C23H26O10
(<i>S</i>)-7-β-D-glucopyranosyloxy-5-methoxy-2-(4-methoxy-phenyl)-chroman-4-one
—— 6-chloro-2-phenyl-3,4-dihydro-2H-chromen-4-ol 97723-88-1 C15H13ClO2
6-chloro-2-phenyl-3,4-dihydro-2H-chromen-4-ol
—— 8-methacryloxyethoxy-[3-(4-ethoxyphenyl)-3-phenyl]-3H-naphtho[2,1-b]pyran 1610880-71-1 C33H30O5
8-methacryloxyethoxy-[3-(4-ethoxyphenyl)-3-phenyl]-3H-naphtho[2,1-b]pyran
—— Tetrahydrocolumbianactin 103629-89-6 C19H24O5
Tetrahydrocolumbianactin
—— 4-chloro-7-fluoro-3-formyl-flav-3-ene 98769-93-8 C16H10ClFO2
4-chloro-7-fluoro-3-formyl-flav-3-ene
—— Chrysin-7-glucosid-pentaacetat 122472-95-1 C31H30O14
Chrysin-7-glucosid-pentaacetat
—— 8-ethoxy-2-(3,4-dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one 743427-49-8 C22H24O8
8-ethoxy-2-(3,4-dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one
—— ethyl 4,10-dioxo-2-phenyl-7,10-dihydro-4H-pyrano-[2,3-f]quinoline-9-carboxylate 1492929-09-5 C21H15NO5
ethyl 4,10-dioxo-2-phenyl-7,10-dihydro-4H-pyrano-[2,3-f]quinoline-9-carboxylate
—— 1352172-08-7 C41H28Cl2N4O3
—— 2-[4-(benzyloxy)-3-nitrophenyl]-3-hydroxy-6-methyl-4H-chromen-4-one 372102-03-9 C23H17NO6
2-[4-(benzyloxy)-3-nitrophenyl]-3-hydroxy-6-methyl-4H-chromen-4-one
—— 5-Hydroxy-2',3,6-trimethoxy-flavon 1165-44-2 C18H16O6
5-Hydroxy-2',3,6-trimethoxy-flavon
—— 7-n-Butoxy-3',4'-methylendioxy-flavonol 59880-46-5 C20H18O6
7-n-Butoxy-3',4'-methylendioxy-flavonol
—— (2R,3R)-3-nitro-2-(4-phenylmethoxyphenyl)-3,4-dihydro-2H-chromene 81289-23-8 C22H19NO4
(2R,3R)-3-nitro-2-(4-phenylmethoxyphenyl)-3,4-dihydro-2H-chromene
—— 8-bromo-7-butoxy-2-(4-chlorophenyl)-6-nitrochromen-4-one 135878-79-4 C19H15BrClNO5
8-bromo-7-butoxy-2-(4-chlorophenyl)-6-nitrochromen-4-one
—— 2-phenyl-5-methoxy-6-methyl-7-hydroxybenzopyran hydrochloride 1447-85-4 C17H15O3*Cl
2-phenyl-5-methoxy-6-methyl-7-hydroxybenzopyran hydrochloride
—— 2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one 1429665-34-8 C16H9F3O3
2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one
—— 1616883-78-3 C21H18O6
—— 6-Fluoro-2-(4-hydroxy-phenyl)-chromen-4-one oxime 321976-79-8 C15H10FNO3
6-Fluoro-2-(4-hydroxy-phenyl)-chromen-4-one oxime
—— 6-bromo-2-(3,4-dimethoxy-phenyl)-3-hydroxy-benzo[<i>h</i>]chromen-4-one 111531-42-1 C21H15BrO5
6-bromo-2-(3,4-dimethoxy-phenyl)-3-hydroxy-benzo[<i>h</i>]chromen-4-one
—— 6-Fluor-8-brom-4'-dimethylamino-flavon 2838-87-1 C17H13BrFNO2
6-Fluor-8-brom-4'-dimethylamino-flavon
—— 3-(4-fluoro-3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yI)propoxy)phenyI)-2H-chromen-6-ol 1352308-20-3 C30H32FNO4
3-(4-fluoro-3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yI)propoxy)phenyI)-2H-chromen-6-ol
—— N-[4-(3-bromo-7-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide 147341-67-1 C18H13BrN2O5
N-[4-(3-bromo-7-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide
—— 3-bromo-8-methyl-6-nitro-2-phenyl-chromen-4-one 131866-09-6 C16H10BrNO4
3-bromo-8-methyl-6-nitro-2-phenyl-chromen-4-one
—— 3-hydroxy-6-benzyloxy-5,7,2',4',5'-pentamethoxyflavone 80496-77-1 C27H26O9
3-hydroxy-6-benzyloxy-5,7,2',4',5'-pentamethoxyflavone
—— (1-methoxy-6-(3-trifluoromethyl)phenyl-7-methyl-6H-dibenzo(b,d)pyran-8-yl)amine 328391-55-5 C22H18F3NO2
(1-methoxy-6-(3-trifluoromethyl)phenyl-7-methyl-6H-dibenzo(b,d)pyran-8-yl)amine
—— 2',3,3',5,7-pentahydroxy-4'-methoxyflavone 101909-70-0 C16H12O8
2',3,3',5,7-pentahydroxy-4'-methoxyflavone
—— (2S,3R,4S,5S,6R)-2-(((2R,3S)-3-hydroxy-7-methoxy-2-(4-methoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-5-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 105330-65-2 C29H38O16
(2S,3R,4S,5S,6R)-2-(((2R,3S)-3-hydroxy-7-methoxy-2-(4-methoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-5-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
—— 2-[2-(benzyloxy)-3,4-dimethoxyphenyl]-3-hydroxy-6-methyl-4H-chromen-4one 372102-25-5 C25H22O6
2-[2-(benzyloxy)-3,4-dimethoxyphenyl]-3-hydroxy-6-methyl-4H-chromen-4one
—— 3,6-Dimethoxy-flavon-2'-carbonsaeure-methylester 98783-10-9 C19H16O6
3,6-Dimethoxy-flavon-2'-carbonsaeure-methylester
—— 6,7,3',4'-Tetramethoxy-5-aethoxy-flavon 111796-46-4 C21H22O7
6,7,3',4'-Tetramethoxy-5-aethoxy-flavon
—— 5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-4H,8H-pyrano[2,3-f]chromen-4-one 50679-01-1 C25H24O4
5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-4H,8H-pyrano[2,3-f]chromen-4-one
—— 6-methyl-3-[(methoxymethyl)oxy]flavone 263153-67-9 C18H16O4
6-methyl-3-[(methoxymethyl)oxy]flavone
—— N-[4-(3-bromo-8-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide 145665-94-7 C18H13BrN2O5
N-[4-(3-bromo-8-methyl-4-oxochromen-2-yl)-2-nitrophenyl]acetamide