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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
—— Acetic acid (2R,3S,4S,2'R,3'R)-2,2'-bis-(3,4-dimethoxy-phenyl)-3,5,7,5',7'-pentamethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3'-yl ester 88204-06-2 C41H46O13
Acetic acid (2R,3S,4S,2'R,3'R)-2,2'-bis-(3,4-dimethoxy-phenyl)-3,5,7,5',7'-pentamethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3'-yl ester
—— 1421313-31-6 C39H38O7
—— 3-bromo-4'-methoxy-6-methylflavanone 72149-92-9 C17H15BrO3
3-bromo-4'-methoxy-6-methylflavanone
—— 2-(4-ethylphenyl)chroman-4,6-diol 488848-16-4 C17H18O3
2-(4-ethylphenyl)chroman-4,6-diol
—— 2-(3-bromo-phenyl)-chroman-4,6-diol 488848-08-4 C15H13BrO3
2-(3-bromo-phenyl)-chroman-4,6-diol
—— (2R,3S,10S)-7,8,9,13-tetramethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one 126655-09-2 C29H30O10
(2R,3S,10S)-7,8,9,13-tetramethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one
—— (+)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 773859-55-5 C64H54O9
(+)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
—— 1431847-41-4 C18H12O3
—— penta-O-acetyl-(-)-robinetinidol 17445-93-1 C25H24O11
penta-O-acetyl-(-)-robinetinidol
—— 6,7-difluoro-2,2-diphenyl-2H-chromene 1393641-97-8 C21H14F2O
6,7-difluoro-2,2-diphenyl-2H-chromene
—— 4-oxo-2-phenyl-5-p-tolyl-2,3,4,5-tetrahydrofuro[3,2-c]pyridine-7-carbaldehyde 1352009-84-7 C21H17NO3
4-oxo-2-phenyl-5-p-tolyl-2,3,4,5-tetrahydrofuro[3,2-c]pyridine-7-carbaldehyde
—— Acetic acid (S)-7-acetoxy-5-hydroxy-2'-methyl-2'-(4-methyl-pent-3-enyl)-4-oxo-3,4-dihydro-2H,2'H-[2,6']bichromenyl-5'-yl ester 92280-26-7 C29H30O8
Acetic acid (S)-7-acetoxy-5-hydroxy-2'-methyl-2'-(4-methyl-pent-3-enyl)-4-oxo-3,4-dihydro-2H,2'H-[2,6']bichromenyl-5'-yl ester
—— Neohuperidosyl-6-trihydroxy-4,4',6-auron 33078-57-8 C27H30O14
Neohuperidosyl-6-trihydroxy-4,4',6-auron
—— 5,7,3',4'-Tetra-O-benzyl-6-bromo-3-O-(tetrahydropyran-2-yl)catechin 1098231-50-5 C48H45BrO7
5,7,3',4'-Tetra-O-benzyl-6-bromo-3-O-(tetrahydropyran-2-yl)catechin
—— 4-hydroxy-4-[4-(5-iodopentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran 209324-97-0 C30H35IO7
4-hydroxy-4-[4-(5-iodopentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran
—— (2R,3R,4S,7S,8R)-4,8-Bis-(3,4-dihydroxy-phenyl)-2-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,5,7-triol 130878-03-4 C30H26O11
(2R,3R,4S,7S,8R)-4,8-Bis-(3,4-dihydroxy-phenyl)-2-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,5,7-triol
—— 7-Hydroxy-8-methyl-flavylium 46890-30-6 C16H13O2
7-Hydroxy-8-methyl-flavylium
—— (-)-fisetidinol-(4α,6)-(+)-catechin-O-methyl ether 119065-90-6 C31H28O11
(-)-fisetidinol-(4α,6)-(+)-catechin-O-methyl ether
—— 2-<4-Methoxy-phenyl>-6-benzoyl-chromon 95811-70-4 C23H16O4
2-<4-Methoxy-phenyl>-6-benzoyl-chromon
—— 7-Methoxy-8-methyliminomethyl-3-ethyl-flavon 88827-66-1 C20H19NO3
7-Methoxy-8-methyliminomethyl-3-ethyl-flavon
—— Acetylderivat von 6-Nitro-4'-hydroxy-flavonol 109469-06-9 C19H13NO8
Acetylderivat von 6-Nitro-4'-hydroxy-flavonol
—— 6-Nitro-3'-chlor-4'-methoxy-flavanon 101423-25-0 C16H12ClNO5
6-Nitro-3'-chlor-4'-methoxy-flavanon
—— 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromen-4-one 113558-11-5 C39H50O19
3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromen-4-one
—— 6-benzyloxy-5,7,3',4'-tetramethoxyflavone 25782-15-4 C26H24O7
6-benzyloxy-5,7,3',4'-tetramethoxyflavone
—— [(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 4-(trifluoromethyl)benzoate 217661-77-3 C40H42F3O21
[(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 4-(trifluoromethyl)benzoate
—— 3,3-di(4-diethylaminophenyl)-3H-naphtho[2,1-b]pyran 282731-94-6 C33H36N2O
3,3-di(4-diethylaminophenyl)-3H-naphtho[2,1-b]pyran
—— 2-methyl-4,4-diphenyl-4,4a-dihydro-2<i>H</i>-chromeno[3,2-<i>c</i>]pyridine-3,10-dione 70611-85-7 C25H19NO3
2-methyl-4,4-diphenyl-4,4a-dihydro-2<i>H</i>-chromeno[3,2-<i>c</i>]pyridine-3,10-dione
—— N-[2-nitro-4-(3,6,7,8-tetrabromo-4-oxochromen-2-yl)phenyl]acetamide 145665-93-6 C17H8Br4N2O5
N-[2-nitro-4-(3,6,7,8-tetrabromo-4-oxochromen-2-yl)phenyl]acetamide
—— (2S)-2-[2-[(E)-7-amino-3,7-dimethyloct-2-enyl]-3,4-dimethoxyphenyl]-6-(3-amino-3-methylbutyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one 1130021-54-3 C34H50N2O6
(2S)-2-[2-[(E)-7-amino-3,7-dimethyloct-2-enyl]-3,4-dimethoxyphenyl]-6-(3-amino-3-methylbutyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one
—— Isomelacacidin-4-p-tolylsulfon 131976-07-3 C22H20O8S
Isomelacacidin-4-p-tolylsulfon
—— 1514898-64-6 C29H22N2O4S
—— (2R,3S,4S)-3-Chloro-6-methyl-2-phenyl-chroman-4-ol 75595-43-6 C16H15ClO2
(2R,3S,4S)-3-Chloro-6-methyl-2-phenyl-chroman-4-ol
—— 3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-pyrrolidino)ethoxy]-phenyl]dibenzo[b,d]pyran 713520-69-5 C37H53NO4Si2
3,8-di(t-butyldimethylsilyloxy)-6-[4-[2-(1-pyrrolidino)ethoxy]-phenyl]dibenzo[b,d]pyran
—— ent-tetramethyl hopeahainol A 1228308-45-9 C32H24O8
ent-tetramethyl hopeahainol A
—— 5,4'-Diacetoxy-3,7,8-trimethoxy-flavon 10568-50-0 C22H20O9
5,4'-Diacetoxy-3,7,8-trimethoxy-flavon
—— 5,7,8,2'-Tetramethoxy-flavonol 96308-85-9 C19H18O7
5,7,8,2'-Tetramethoxy-flavonol
—— 3-Hydroxy-5.7.3'-trimethoxy-4'-methoxymethoxy-flavon 109979-43-3 C20H20O8
3-Hydroxy-5.7.3'-trimethoxy-4'-methoxymethoxy-flavon
—— 2',4'-Dibenzyloxy-5,7-dimethoxy-flavon 103271-47-2 C31H26O6
2',4'-Dibenzyloxy-5,7-dimethoxy-flavon
—— 3-(benzyloxy)-2-[4-(benzyloxy)-3-chlorophenyl]-6-methyl-8-nitro-4H-chromen-4-one 372102-44-8 C30H22ClNO6
3-(benzyloxy)-2-[4-(benzyloxy)-3-chlorophenyl]-6-methyl-8-nitro-4H-chromen-4-one
—— 6-[2-(5,7-Dimethoxy-4-oxo-4H-chromen-2-yl)-4,5-dimethoxy-phenyl]-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one 100288-27-5 C38H34O12
6-[2-(5,7-Dimethoxy-4-oxo-4H-chromen-2-yl)-4,5-dimethoxy-phenyl]-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one
—— 6-Bromo-3,3-dichloro-2-phenyl-chroman-4-ol 75595-35-6 C15H11BrCl2O2
6-Bromo-3,3-dichloro-2-phenyl-chroman-4-ol
—— Aglykon v. Erycitrin = Erycetin 26605-15-2 C20H12O9
Aglykon v. Erycitrin = Erycetin
—— (+/-)-3,6-Dihydroxy-5,7-dimethoxy-2-<2.3-dimethoxy-phenyl>-chromanon-(4) 109560-33-0 C19H20O8
(+/-)-3,6-Dihydroxy-5,7-dimethoxy-2-<2.3-dimethoxy-phenyl>-chromanon-(4)
—— 2-(3-acetoxy-phenyl)-5,7-dimethyl-chroman-4-one 109690-87-1 C19H18O4
2-(3-acetoxy-phenyl)-5,7-dimethyl-chroman-4-one
—— 5-acetoxy-3(3,4-dimethoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran 143099-02-9 C29H23FO5
5-acetoxy-3(3,4-dimethoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran
—— 9-allyl-7-(4-chlorophenyl)-4-hydroxy-5H-furo[3,2-g]chromen-5-one 1616883-72-7 C20H13ClO4
9-allyl-7-(4-chlorophenyl)-4-hydroxy-5H-furo[3,2-g]chromen-5-one
—— 1569601-75-7 C16H10BrClO2
—— (2R,3S)-3-Chloro-6-methyl-2-phenyl-chroman-4-one 75595-95-8 C16H13ClO2
(2R,3S)-3-Chloro-6-methyl-2-phenyl-chroman-4-one
—— 7-benzyloxy-2-hydroxy-5-methoxy-3-(4-methoxy-phenyl)-8-methyl-chroman-4-one 124140-77-8 C25H24O6
7-benzyloxy-2-hydroxy-5-methoxy-3-(4-methoxy-phenyl)-8-methyl-chroman-4-one
—— 7-Butyloxy-3-methyl-flavon 102158-95-2 C20H20O3
7-Butyloxy-3-methyl-flavon