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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-Methyl-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-7-(tetrahydro-pyran-2-yloxy)-chroman-4-one 690274-17-0 C28H35NO5
3-Methyl-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-7-(tetrahydro-pyran-2-yloxy)-chroman-4-one
—— 3,5-diacetoxy-2-(4-acetoxy-phenyl)-8-(3-methyl-but-2-enyl)-7-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 55394-99-5 C40H42O18
3,5-diacetoxy-2-(4-acetoxy-phenyl)-8-(3-methyl-but-2-enyl)-7-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyloxy)-chromen-4-one
—— (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan 476312-04-6 C46H42O8
(2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan
—— 6-acetylamino-2-(4-hydroxy-phenyl)-3-methyl-chroman-4-one 132593-97-6 C18H17NO4
6-acetylamino-2-(4-hydroxy-phenyl)-3-methyl-chroman-4-one
—— 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-6-methyl-chromen-4-one 115385-97-2 C26H22O12
3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-6-methyl-chromen-4-one
—— 7-Benzyloxycarbonylmethoxy-4-oxo-2-phenyl-4H-chromen 90247-86-2 C24H18O5
7-Benzyloxycarbonylmethoxy-4-oxo-2-phenyl-4H-chromen
—— 1609067-55-1 C31H36N2O10
—— 2,2-dimethyl-7-[3-(2,2,2-trifluoroethoxy)phenyl]-2H-chromene-3,4-dione 1393843-83-8 C19H15F3O4
2,2-dimethyl-7-[3-(2,2,2-trifluoroethoxy)phenyl]-2H-chromene-3,4-dione
—— 7,4'-bis(methoxymethoxy)-5-hydroxyflavanone 134955-31-0 C19H20O7
7,4'-bis(methoxymethoxy)-5-hydroxyflavanone
—— 1609067-54-0 C35H44N2O10
—— 8-acetylamino-2-phenyl-chroman-4-one 108973-51-9 C17H15NO3
8-acetylamino-2-phenyl-chroman-4-one
—— (m-tolyl)chroman-4-one 1315334-82-7 C16H14O2
(m-tolyl)chroman-4-one
—— 2-(2-bromo-3,4-dimethoxyphenyl)-3-hydroxy-6-methyl-4H-chromen-4-one 372102-28-8 C18H15BrO5
2-(2-bromo-3,4-dimethoxyphenyl)-3-hydroxy-6-methyl-4H-chromen-4-one
—— 4-methyl-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide 1467668-58-1 C25H23NO7S
4-methyl-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide
—— 4-bromo-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide 1467668-56-9 C24H20BrNO7S
4-bromo-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide
—— 3'-methoxy-3-methylene flavanone 77038-17-6 C17H14O3
3'-methoxy-3-methylene flavanone
—— 7-hydroxy-5-methoxy-2-(2-methoxyphenyl)-4-oxo-4H-chromene-6-carbaldehyde 1616883-75-0 C18H14O6
7-hydroxy-5-methoxy-2-(2-methoxyphenyl)-4-oxo-4H-chromene-6-carbaldehyde
—— 3'-bromo-3-methylene flavanone 77038-13-2 C16H11BrO2
3'-bromo-3-methylene flavanone
—— 1430210-15-3 C24H15NO3
—— 2-(3,4-Dimethoxy-phenyl)-6-hydroxy-3,7-dimethoxy-chromene-4,5,8-trione 61523-54-4 C19H16O9
2-(3,4-Dimethoxy-phenyl)-6-hydroxy-3,7-dimethoxy-chromene-4,5,8-trione
—— N-benzyl-N-[3-(4-oxo-4H-benzopyrane-2-yl)benzyl]-3-phenylacrylamide 1018817-32-7 C32H25NO3
N-benzyl-N-[3-(4-oxo-4H-benzopyrane-2-yl)benzyl]-3-phenylacrylamide
—— 3-methyl-7-(4-nitro-phenyl)-chromeno[6,5-<i>d</i>]isoxazol-9-one 49586-11-0 C17H10N2O5
3-methyl-7-(4-nitro-phenyl)-chromeno[6,5-<i>d</i>]isoxazol-9-one
—— 4-(2-phenylchroman-6-yloxy)pyridine 728937-39-1 C20H17NO2
4-(2-phenylchroman-6-yloxy)pyridine
—— {(S)-2-methyl-1-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]ethyl}carbamic acid tert-butyl ester 728935-56-6 C30H35N3O5
{(S)-2-methyl-1-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]ethyl}carbamic acid tert-butyl ester
—— 3-Acetoxy-7,3',4'-trimethoxyflavan 99950-73-9 C20H22O6
3-Acetoxy-7,3',4'-trimethoxyflavan
—— (+)-ent-Epicatechin-(4α,4)-resorcinol 155680-22-1 C21H18O8
(+)-ent-Epicatechin-(4α,4)-resorcinol
—— macaflavanone E 1075194-64-7 C30H34O6
macaflavanone E
—— morusin 67492-56-2 C25H26O6
morusin
—— 7-(2-hydroxy-ethyl)-3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione 1279088-51-5 C16H12INO4
7-(2-hydroxy-ethyl)-3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione
—— 6-Naphthalen-2-yl-2,2-diphenylchromene 933066-95-6 C31H22O
6-Naphthalen-2-yl-2,2-diphenylchromene
—— 7-((4-methoxyphenyl)amino)-2-phenyl-4H-chromen-4-one 1644565-44-5 C22H17NO3
7-((4-methoxyphenyl)amino)-2-phenyl-4H-chromen-4-one
—— 8-allyl-6-chloro-3-hydroxyflavone 901768-84-1 C18H13ClO3
8-allyl-6-chloro-3-hydroxyflavone
—— 1400900-13-1 C30H23ClFNO3S
—— 7-<N-(2-Hydroxy-ethyl)-N-methyl-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen 90115-68-7 C20H19NO5
7-<N-(2-Hydroxy-ethyl)-N-methyl-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen
—— prunin 6''-O-butyrate 1256627-50-5 C25H28O11
prunin 6''-O-butyrate
—— 6-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)chromane 946062-96-0 C19H22O5
6-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)chromane
—— [(2R,3S)-5-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-3-yl] acetate 20717-28-6 C23H24O9
[(2R,3S)-5-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-3-yl] acetate
—— 5-Amino-2-(4-amino-3-fluoro)phenyl-4H-benzopyran-4-one 130599-75-6 C15H11FN2O2
5-Amino-2-(4-amino-3-fluoro)phenyl-4H-benzopyran-4-one
—— (2R,2'R,3S,3'S,4S,4'S,5R,5'R,6S,6'S)-6,6'-((4-((2R,3S)-3-hydroxy-5,7-dimethoxychroman-2-yl)-1,2-phenylene)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol) 105330-67-4 C29H38O16
(2R,2'R,3S,3'S,4S,4'S,5R,5'R,6S,6'S)-6,6'-((4-((2R,3S)-3-hydroxy-5,7-dimethoxychroman-2-yl)-1,2-phenylene)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
—— (+/-)-3<i>t</i>,7-Diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-chroman 863-02-5 C23H22O9
(+/-)-3<i>t</i>,7-Diacetoxy-2<i>r</i>-(3,4-diacetoxy-phenyl)-chroman
—— (2S,3R,4S,5S,6R)-2-(((2R,3S)-3-hydroxy-5-methoxy-2-(4-methoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-7-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 105351-71-1 C29H38O16
(2S,3R,4S,5S,6R)-2-(((2R,3S)-3-hydroxy-5-methoxy-2-(4-methoxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-7-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
—— 2-benzo[1,3]dioxol-5-yl-5-hydroxy-6,7,8-trimethoxy-chromen-4-one 3151-84-6 C19H16O8
2-benzo[1,3]dioxol-5-yl-5-hydroxy-6,7,8-trimethoxy-chromen-4-one
—— N-{8-amino-3-(benzyloxy)-2-[4-(benzyloxy)-3-chlorophenyl]-4-oxo-4H-chromen-6-yl}acetamide 372102-98-2 C31H25ClN2O5
N-{8-amino-3-(benzyloxy)-2-[4-(benzyloxy)-3-chlorophenyl]-4-oxo-4H-chromen-6-yl}acetamide
—— 7,4'-dimethoxymethyl-5-O-geranylapigenin 134955-32-1 C29H34O7
7,4'-dimethoxymethyl-5-O-geranylapigenin
—— 9-bromo-2-phenyl-pyrano[3,2-c]quinolin-4-one 98706-80-0 C18H10BrNO2
9-bromo-2-phenyl-pyrano[3,2-c]quinolin-4-one
—— 2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-(tetrahydropyran-2-yloxy)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-2,3-dihydro-4H-1-benzopyran-4-one 361391-14-2 C33H35ClO6S
2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-(tetrahydropyran-2-yloxy)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-2,3-dihydro-4H-1-benzopyran-4-one
—— [(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-(trifluoromethyl)phenyl]prop-2-enoate 217661-72-8 C42H44F3O21
[(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-(trifluoromethyl)phenyl]prop-2-enoate
—— 3,8-dibromo-7-butoxy-6-nitro-2-(3,4,5-trimethoxyphenyl)chromen-4-one 139589-41-6 C22H21Br2NO8
3,8-dibromo-7-butoxy-6-nitro-2-(3,4,5-trimethoxyphenyl)chromen-4-one
—— 1-(2-(4-chlorophenyl)chroman-4-ylidene)-2-phenylhydrazine 1234138-44-3 C21H17ClN2O
1-(2-(4-chlorophenyl)chroman-4-ylidene)-2-phenylhydrazine
—— 2-(3-chloro-4-fluorophenyl)-6-hydroxychroman-4-one 728934-36-9 C15H10ClFO3
2-(3-chloro-4-fluorophenyl)-6-hydroxychroman-4-one