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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
—— methyl 3-(((2-(4-(2-(2-(2-(4-(4-(4-(6-methyl-4-oxo-4H-chromen-2-yl)phenoxy)butyl)-1H-1,2,3-triazol-1-yl)-ethoxy)ethoxy)ethoxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-methyl)benzoate 1451740-81-0 C52H49N3O11
methyl 3-(((2-(4-(2-(2-(2-(4-(4-(4-(6-methyl-4-oxo-4H-chromen-2-yl)phenoxy)butyl)-1H-1,2,3-triazol-1-yl)-ethoxy)ethoxy)ethoxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-methyl)benzoate
—— 3-hydroxy-2-(5-iodo-2-methoxyphenyl)-4H-chromen-4-one 1443430-19-0 C16H11IO4
3-hydroxy-2-(5-iodo-2-methoxyphenyl)-4H-chromen-4-one
—— naringenin 7-O-β-(6''-galloylglucopyranoside) 54835-98-2 C28H26O14
naringenin 7-O-β-(6''-galloylglucopyranoside)
—— 2-(5-chloro-2-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one 1443430-21-4 C17H13ClO4
2-(5-chloro-2-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one
—— 2-(4-chlorophenyl)-7-fluoro-4H-chromen-4-one 1427317-34-7 C15H8ClFO2
2-(4-chlorophenyl)-7-fluoro-4H-chromen-4-one
—— Naringenin-4a(2)-O-glucuronide 158196-35-1 C21H20O11
Naringenin-4a(2)-O-glucuronide
—— 7,3'-Di-O-glucosylluteolin 52187-80-1 C27H30O16
7,3'-Di-O-glucosylluteolin
—— Anthocyanidin, Malvidin-3-glucoside-chloride 7228-78-6 C23H25O12*Cl
Anthocyanidin, Malvidin-3-glucoside-chloride
—— (E)-5,7-dihydroxy-2-(4-hydroxy-2-methoxyphenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one 1443276-43-4 C26H28O6
(E)-5,7-dihydroxy-2-(4-hydroxy-2-methoxyphenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
—— 6,8-dichloro-2-(4-iodophenyl)-3-nitro-2H-chromene 1448552-59-7 C15H8Cl2INO3
6,8-dichloro-2-(4-iodophenyl)-3-nitro-2H-chromene
—— Ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-oxo-2,3-dihydrochromene-3-carboxylate 1448552-74-6 C18H13Cl2FO4
Ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-oxo-2,3-dihydrochromene-3-carboxylate
—— (2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one 959421-22-8 C21H22O6
(2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
—— 2,3-Dihydro-3-[(3-hydroxyphenyl)methylene]-2-phenyl-4H-1-benzopyran-4-one 67570-40-5 C22H16O3
2,3-Dihydro-3-[(3-hydroxyphenyl)methylene]-2-phenyl-4H-1-benzopyran-4-one
—— 4-Oxo-2-phenylchromen-3-olate;oxovanadium(2+) 1443102-25-7 C30H18O7V
4-Oxo-2-phenylchromen-3-olate;oxovanadium(2+)
—— isoscoparin 2''-O-glucoside 97605-25-9 C28H32O16
isoscoparin 2''-O-glucoside
—— 4',5,6,7,8-pentamethoxy-3-flavene 1443134-14-2 C20H22O6
4',5,6,7,8-pentamethoxy-3-flavene
—— 7-Bromo-2-(4-hydroxyphenyl)-4H-chromen-4-one 1194374-36-1 C15H9BrO3
7-Bromo-2-(4-hydroxyphenyl)-4H-chromen-4-one
—— 4-(3-Hydroxy-6-methoxy-4-oxo-4H-1-benzopyran-2-yl)benzoic acid 663605-25-2 C17H12O6
4-(3-Hydroxy-6-methoxy-4-oxo-4H-1-benzopyran-2-yl)benzoic acid
—— kaempferol 5-O-beta-D-glucopyranoside 34157-80-7 C21H20O11
kaempferol 5-O-beta-D-glucopyranoside
—— 3'-O-(beta-Hydroxyethyl)rutoside 125092-04-8 C29H34O17
3'-O-(beta-Hydroxyethyl)rutoside
—— 3',4',5-Tri-O-(beta-hydroxyethyl)rutoside 862126-97-4 C33H42O19
3',4',5-Tri-O-(beta-hydroxyethyl)rutoside
—— 3',4'-Di-O-(beta-hydroxyethyl)rutoside 862127-01-3 C31H38O18
3',4'-Di-O-(beta-hydroxyethyl)rutoside
—— 5,3'-Di-O-(beta-hydroxyethyl)rutoside 862127-05-7 C31H38O18
5,3'-Di-O-(beta-hydroxyethyl)rutoside
—— 5,4'-Di-O-(beta-hydroxyethyl)rutoside 862127-07-9 C31H38O18
5,4'-Di-O-(beta-hydroxyethyl)rutoside
—— 4'-O-(beta-Hydroxyethyl)rutoside 13190-92-6 C29H34O17
4'-O-(beta-Hydroxyethyl)rutoside
—— 3',7-Di-O-(beta-hydroxyethyl)rutoside 72352-99-9 C31H38O18
3',7-Di-O-(beta-hydroxyethyl)rutoside
—— Cyanidin 3-O-rhamnoside 38533-30-1 C21H21O10+
Cyanidin 3-O-rhamnoside
—— 1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde 1529772-97-1 C28H23NO5
1-[4-(5-Hydroxy-4-oxo-2-phenylchromen-7-yl)oxybutyl]indole-3-carbaldehyde
—— 2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one —— C33H42O19
2-[3,4-bis(2-hydroxyethoxy)phenyl]-5-hydroxy-7-(2-hydroxyethoxy)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— Delphinidin 3,5-di(6-O-malonylglucoside) 104078-09-3 C33H35O23+
Delphinidin 3,5-di(6-O-malonylglucoside)
—— Epigallocatechin gallate 4'-stearate 863725-78-4 C40H52O12
Epigallocatechin gallate 4'-stearate
—— 8-(Indolin-5-yl)chromeno[7,8-d]imidazol-6(3H)-one 1956355-04-6 C18H13N3O2
8-(Indolin-5-yl)chromeno[7,8-d]imidazol-6(3H)-one
—— 7-[3-[(4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one 26544-34-3 C26H28O14
7-[3-[(4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
—— (2E)-6-[3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4-methoxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one 66274-45-1 C28H32O16
(2E)-6-[3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4-methoxy-2-[(3,4,5-trihydroxyphenyl)methylidene]-1-benzofuran-3-one
—— 4'-Methoxy-3-<2-morpholino-aethoxy>-flavon 95130-80-6 C22H23NO5
4'-Methoxy-3-<2-morpholino-aethoxy>-flavon
—— Cyanidin 4'-glucoside 27459-77-4 C21H21O11+
Cyanidin 4'-glucoside
—— (2S)-2,3-Dihydro-5,7-dimethoxy-6-methyl-2-phenyl-4H-1-benzopyran-4-one 128508-16-7 C18H18O4
(2S)-2,3-Dihydro-5,7-dimethoxy-6-methyl-2-phenyl-4H-1-benzopyran-4-one
—— Limbrel 1206488-21-2 C36H32O17
Limbrel
—— Kaempferol 3-O-glucosyl-rhamnosyl-glucoside 136449-09-7 C33H40O20
Kaempferol 3-O-glucosyl-rhamnosyl-glucoside
—— aesculitannin B 114612-77-0 C45H36O18
aesculitannin B
—— epicatechin-5-O-β-D-glucuronide 223614-70-8 C21H22O12
epicatechin-5-O-β-D-glucuronide
—— 5-Acetoxy-3,7,8,3',4'-pentamethoxy-flavon 57528-78-6 C22H22O9
5-Acetoxy-3,7,8,3',4'-pentamethoxy-flavon
—— quercetin 3-O-<O-6'''-O-(p-coumaroyl)-β-D-glucopyranosyl-(1->4)-α-L-rhamnoside> 113447-39-5 C36H36O18
quercetin 3-O-<O-6'''-O-(p-coumaroyl)-β-D-glucopyranosyl-(1->4)-α-L-rhamnoside>
—— 2,2-Dimethyl-propionic acid 8-hydroxy-5S*(+)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester —— C34H37NO6
2,2-Dimethyl-propionic acid 8-hydroxy-5S*(+)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester
—— (2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol 88489-00-3 C15H13BrO6
(2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
—— Cyanidin 3-malonylglucoside 94977-38-5 C24H23O14+
Cyanidin 3-malonylglucoside
—— Tribuloside 22153-44-2 C30H26O13
Tribuloside
—— rel-(3aR,4S,9bS)-1,2,3,3a,4,9b-Hexahydro-4-phenylcyclopenta[c][1]benzopyran-8-ol 609806-61-3 C18H18O2
rel-(3aR,4S,9bS)-1,2,3,3a,4,9b-Hexahydro-4-phenylcyclopenta[c][1]benzopyran-8-ol
—— Kaempferol 3-glucuronoside 22688-78-4 C21H18O12
Kaempferol 3-glucuronoside
—— (2S)-5,7,2',4'-Tetrahydroxy-8-prenyl-5'-(1,1-dimethylallyl)flavanone 460345-17-9 C25H28O6
(2S)-5,7,2',4'-Tetrahydroxy-8-prenyl-5'-(1,1-dimethylallyl)flavanone