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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
—— 4-{7-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2H-chromen-2-yl}-phenol 173676-52-3 C33H44O4Si2
4-{7-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2H-chromen-2-yl}-phenol
—— (+/-)-4',7-dibenzyloxy<2-2H>flavanone 95307-74-7 C29H24O4
(+/-)-4',7-dibenzyloxy<2-2H>flavanone
—— 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside 132203-74-8 C27H32O14
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
—— (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-[2,8']bichromenyl-3,5,7,3',5',7'-hexaol 128428-24-0 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-[2,8']bichromenyl-3,5,7,3',5',7'-hexaol
—— 3'-cyano-3-methylene flavanone 77038-33-6 C17H11NO2
3'-cyano-3-methylene flavanone
—— 7-(phenylamino)-2-phenyl-4H-chromen-4-one 1644565-42-3 C21H15NO2
7-(phenylamino)-2-phenyl-4H-chromen-4-one
—— 3-methyl-5,7,4′-trimethoxyflavone 22395-14-8 C19H18O5
3-methyl-5,7,4′-trimethoxyflavone
—— methyl 3-(((2-(4-(2-(2-hydroxyethoxy)ethoxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)methyl)benzoate 1451740-31-0 C28H26O8
methyl 3-(((2-(4-(2-(2-hydroxyethoxy)ethoxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)methyl)benzoate
—— 7-Hydroxy-5-methoxy-8-methyl-flavon 93322-11-3 C17H14O4
7-Hydroxy-5-methoxy-8-methyl-flavon
—— 127304-90-9 C2F3O2*C75H81O42
—— 2-(3-chloro-4-methoxyphenyl)-3-methoxy-8-[1-(2-methoxyethyl)-4-piperidinyl]-6-methyl-4H-chromen-4-one 741664-12-0 C26H30ClNO5
2-(3-chloro-4-methoxyphenyl)-3-methoxy-8-[1-(2-methoxyethyl)-4-piperidinyl]-6-methyl-4H-chromen-4-one
—— 3,4'-Dihydroxy-3'-methoxyflavon-6-carbonsaeure 93328-30-4 C17H12O7
3,4'-Dihydroxy-3'-methoxyflavon-6-carbonsaeure
—— 4-methoxy-6-(3-chlorophenyl)-6,12-methano-12H-dibenzo[d,g][1,3]dioxocin 1429327-11-6 C22H17ClO3
4-methoxy-6-(3-chlorophenyl)-6,12-methano-12H-dibenzo[d,g][1,3]dioxocin
—— 3-[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-8-yl]-propionic acid 873994-75-3 C21H20O7
3-[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-8-yl]-propionic acid
—— N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide 260064-10-6 C27H19F3N2O8S
N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide
—— 10,11,12,13-Tetrahydromorusin 64892-18-8 C25H28O6
10,11,12,13-Tetrahydromorusin
—— kaempferol 3,7-di-O-α-L-rhamnoside peracetate 85561-92-8 C43H46O22
kaempferol 3,7-di-O-α-L-rhamnoside peracetate
—— 3,5-Diacetoxy-4'-benzyloxy-3',7-dimethoxy-flavon 83332-31-4 C28H24O9
3,5-Diacetoxy-4'-benzyloxy-3',7-dimethoxy-flavon
—— N-{5-[8-(ureido)-3-hydroxy-6-methyl-4-oxo-4H-chromen-2-yl]-2-hydroxyphenyl}urea 372102-16-4 C18H16N4O6
N-{5-[8-(ureido)-3-hydroxy-6-methyl-4-oxo-4H-chromen-2-yl]-2-hydroxyphenyl}urea
—— methyl 2-(6-methyl-4-oxo-2-phenylchromen-8-yl)butanoate 213622-45-8 C21H20O4
methyl 2-(6-methyl-4-oxo-2-phenylchromen-8-yl)butanoate
—— (+/-)-cis-4',7-Dimethoxy-flavan-3-ol 98200-81-8 C17H18O4
(+/-)-cis-4',7-Dimethoxy-flavan-3-ol
—— N-(4-fluorobenzyl)-N-[3-(4-oxo-4H-benzopyrane-2-yl)benzyl]-3-phenylacrylamide 1018817-33-8 C32H24FNO3
N-(4-fluorobenzyl)-N-[3-(4-oxo-4H-benzopyrane-2-yl)benzyl]-3-phenylacrylamide
—— (2R,3R)-2-(3-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxyphenyl)chromane-3,5,7-triol 1226711-30-3 C27H34O16
(2R,3R)-2-(3-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxyphenyl)chromane-3,5,7-triol
—— 2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-8-(4-pyridinyl)-4H-chromen-4-one 372103-26-9 C23H18ClNO4
2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-8-(4-pyridinyl)-4H-chromen-4-one
—— 8-Amino-2-(1,3-benzodioxol-5-yl)-3-methoxy-6-methylchromen-4-one 934374-04-6 C18H15NO5
8-Amino-2-(1,3-benzodioxol-5-yl)-3-methoxy-6-methylchromen-4-one
—— Bichrysinyl-5,7,5''-7''-tetramethylaether 26505-97-5 C34H26O8
Bichrysinyl-5,7,5''-7''-tetramethylaether
—— 5,7-dimethoxy-2-(2-methoxymethoxy-phenyl)-chroman-4-one 110048-31-2 C19H20O6
5,7-dimethoxy-2-(2-methoxymethoxy-phenyl)-chroman-4-one
—— 7''-O-methyl amentoflavone pentaacetate 67882-15-9 C41H30O15
7''-O-methyl amentoflavone pentaacetate
—— 7-methoxy-6-nitro-2-phenyl-chromen-4-one 132318-83-3 C16H11NO5
7-methoxy-6-nitro-2-phenyl-chromen-4-one
—— (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2"-ethoxyethoxy)flavan 664351-41-1 C49H48O9
(2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2"-ethoxyethoxy)flavan
—— [(2R,3S)-7-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-chromen-3-yl] acetate 105330-64-1 C23H24O9
[(2R,3S)-7-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-chromen-3-yl] acetate
—— N',N'''-(((3H-benzo[f]chromene-3,3-diyl)bis(4,1-phenylene))bis(methaneylylidene))bis(2-methoxybenzohydrazide) 1352172-14-5 C43H34N4O5
N',N'''-(((3H-benzo[f]chromene-3,3-diyl)bis(4,1-phenylene))bis(methaneylylidene))bis(2-methoxybenzohydrazide)
—— 4'-Methoxy-flavan-4β-ol 1195611-56-3 C16H16O3
4'-Methoxy-flavan-4β-ol
—— N,N'-Di-flavanyl-(4)-harnstoff 96590-36-2 C31H28N2O3
N,N'-Di-flavanyl-(4)-harnstoff
—— 3,2',6'-Trihydroxy-4-methoxychalcone 2'-O-β-D-galactopyranoside 88087-11-0 C22H24O10
3,2',6'-Trihydroxy-4-methoxychalcone 2'-O-β-D-galactopyranoside
—— 3-Hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one 111391-57-2 C23H18O4
3-Hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one
—— 3-Jod-7-methyl-4'-methoxy-flavanon 81877-77-2 C17H15IO3
3-Jod-7-methyl-4'-methoxy-flavanon
—— [(S)-2-methyl-1-(6-{2-[3-(5-nitropyridin-2-yloxy)phenyl]chroman-6-yloxy}pyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester 728935-74-8 C35H37N5O8
[(S)-2-methyl-1-(6-{2-[3-(5-nitropyridin-2-yloxy)phenyl]chroman-6-yloxy}pyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester
—— [(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-(3,4,5-trimethoxyphenyl)prop-2-enoate 142506-22-7 C44H51O24
[(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-(3,4,5-trimethoxyphenyl)prop-2-enoate
—— 7-((4-fluorophenyl)amino)-2-phenyl-4H-chromen-4-one 1644565-48-9 C21H14FNO2
7-((4-fluorophenyl)amino)-2-phenyl-4H-chromen-4-one
—— 2,2-diphenyl-2H-benzo[b]furano[3,2-f]benzopyran 152365-44-1 C27H18O2
2,2-diphenyl-2H-benzo[b]furano[3,2-f]benzopyran
—— 3,'4'-Diacetoxy-flavan 95937-53-4 C19H18O5
3,'4'-Diacetoxy-flavan
—— 7-dimethylamino-6-methoxy-2-(4-(N-morpholinyl)phenyl)-2-phenyl-2H-benzofuro[3,2-h]benzo[f]chromene 404934-48-1 C38H34N2O4
7-dimethylamino-6-methoxy-2-(4-(N-morpholinyl)phenyl)-2-phenyl-2H-benzofuro[3,2-h]benzo[f]chromene
—— 1352172-15-6 C41H30N4O3
—— 2-[3-(pyridin-2-yloxy)phenyl]chroman-6-ol 728935-14-6 C20H17NO3
2-[3-(pyridin-2-yloxy)phenyl]chroman-6-ol
—— 2-Azido-3-methyl-2-phenyl-3-chromen 53486-65-0 C16H13N3O
2-Azido-3-methyl-2-phenyl-3-chromen
—— 2-(1,3-benzodioxol-5-yl)-8-bromo-7-butoxy-6-nitrochromen-4-one 135878-82-9 C20H16BrNO7
2-(1,3-benzodioxol-5-yl)-8-bromo-7-butoxy-6-nitrochromen-4-one
—— 3-Methoxy-6-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one 111391-69-6 C24H20O4
3-Methoxy-6-methyl-2-(4-phenylmethoxyphenyl)chromen-4-one
—— (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2-hydroxy-4,6-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol 1258979-23-5 C23H22O9
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2-hydroxy-4,6-dimethoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2-(1-(4-amino-3-(dimethylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one 1408085-80-2 C24H20F2N6O2
2-(1-(4-amino-3-(dimethylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one