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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
—— (2R)-4-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-hydroxy-4-oxobutanoate —— C25H23O15-
(2R)-4-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-hydroxy-4-oxobutanoate
—— 2'-Hydroxy 3,6,7,4'-tetramethylquercetagetin —— C19H18O9
2'-Hydroxy 3,6,7,4'-tetramethylquercetagetin
—— (2R)-2-hydroxy-4-oxo-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxyoxan-2-yl]methoxy]butanoate —— C25H23O16-
(2R)-2-hydroxy-4-oxo-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxyoxan-2-yl]methoxy]butanoate
—— cyanidin O-O-[6-O-(6-O-4-hydroxycinnamoyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside] —— C41H43O22-
cyanidin O-O-[6-O-(6-O-4-hydroxycinnamoyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside]
—— isorhamnetin 3-O-(3"-O-p-coumaroyl)-glucoside —— C31H28O14
isorhamnetin 3-O-(3"-O-p-coumaroyl)-glucoside
—— 3,7,3',4'-tetramethylquercetin 2'-O-beta-D-glucoside —— C25H28O13
3,7,3',4'-tetramethylquercetin 2'-O-beta-D-glucoside
—— gossypetin 7-O-glucopyranoside —— C21H19O13-
gossypetin 7-O-glucopyranoside
—— 2'-Hydroxy 3,7,3',4'-tetramethylquercetin —— C19H18O8
2'-Hydroxy 3,7,3',4'-tetramethylquercetin
—— Panasenoide —— C27H29O16-
Panasenoide
—— apigeninidin 5-O-glucoside —— C21H20O9
apigeninidin 5-O-glucoside
—— Pinobanksin 7-glucoside —— C21H22O10
Pinobanksin 7-glucoside
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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-hydroxyphenyl)prop-2-enoate —— C41H44O22
[(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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-hydroxyphenyl)prop-2-enoate
—— 2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxychromen-7-one —— C32H38O20
2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxychromen-7-one
—— myricetin 3-O-gentiobioside —— C27H30O18
myricetin 3-O-gentiobioside
—— Carthamidin-7-methyl ether —— C16H14O6
Carthamidin-7-methyl ether
—— 4-(3-Hydroxy-7-methoxy-5-oxochromen-2-yl)-2-methoxyphenolate —— C17H13O6-
4-(3-Hydroxy-7-methoxy-5-oxochromen-2-yl)-2-methoxyphenolate
—— Campanin —— C66H72O37
Campanin
—— pelargonidin-3-O-(6"-O-malonyl-beta-D-glucoside) —— C24H21O13-
pelargonidin-3-O-(6"-O-malonyl-beta-D-glucoside)
—— Malvidin(1-) —— C17H13O7-
Malvidin(1-)
—— Quercetagetin 7-O-glucoside —— C21H19O13-
Quercetagetin 7-O-glucoside
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate —— C43H48O24
[(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxochromen-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-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
—— 3,3'-Dimethylmyricetin —— C17H13O8-
3,3'-Dimethylmyricetin
—— 2-(3-Benzoylphenyl)-3,5,7-trihydroxychromen-4-one —— C22H12O6-2
2-(3-Benzoylphenyl)-3,5,7-trihydroxychromen-4-one
—— 3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-7-one —— C27H30O15
3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-7-one
—— cyanidin O-O-[6-O-(6-O-sinapoyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside] —— C43H47O24-
cyanidin O-O-[6-O-(6-O-sinapoyl-beta-D-glucosyl)-2-O-beta-D-xylosyl-beta-D-galactoside]
—— quercetin 3-O-(4"-O-p-coumaroyl)-glucoside —— C30H26O14
quercetin 3-O-(4"-O-p-coumaroyl)-glucoside
—— [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methyl 4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate —— C46H54O28
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methyl 4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
—— Leschenaultia blue anthocyanin 1 —— C60H63O36-
Leschenaultia blue anthocyanin 1
—— [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate —— C30H26O13
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-oxochromen-3-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
—— 7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-5-one —— C33H40O21
7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-5-one
—— 2-(3,4-dihydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one —— C15H12O7
2-(3,4-dihydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
—— 2-Hydroxy-4-(3-hydroxy-5-methoxy-7-oxochromen-2-yl)-6-methoxyphenolate —— C17H13O7-
2-Hydroxy-4-(3-hydroxy-5-methoxy-7-oxochromen-2-yl)-6-methoxyphenolate
—— 3,6,7,2',4'-pentamethylquercetagetin 3'-O-beta-D-glucoside —— C26H30O14
3,6,7,2',4'-pentamethylquercetagetin 3'-O-beta-D-glucoside
—— 3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxychromen-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid —— C39H38O21
3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxychromen-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
—— isorhamnetin 3-O-(3",6"-O-di-p-coumaroyl)-glucoside —— C40H34O16
isorhamnetin 3-O-(3",6"-O-di-p-coumaroyl)-glucoside
—— cyanidin 3-O-glucoside-7-O-(6-O-(4-O-(glucosyl)-oxybenzoyl)-glucoside) —— C40H44O23
cyanidin 3-O-glucoside-7-O-(6-O-(4-O-(glucosyl)-oxybenzoyl)-glucoside)
—— 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid —— C60H64O36
3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxyoxan-2-yl]methoxy]propanoic acid
—— malvidin 3-O-rutinoside —— C30H36O15
malvidin 3-O-rutinoside
—— delphinidin 3-O-glucosyl-5-O-(caffeoylglucoside-3'-O-glucoside) —— C42H46O25
delphinidin 3-O-glucosyl-5-O-(caffeoylglucoside-3'-O-glucoside)
—— delphinidin 3,7-di O-beta-D-glucoside —— C27H30O17
delphinidin 3,7-di O-beta-D-glucoside
—— Rhamnosylisoorientin —— C27H29O15-
Rhamnosylisoorientin
—— 2-(3,4-Dihydroxyphenyl)-3,6,7-trihydroxy-4-oxochromen-5-olate —— C15H9O8-
2-(3,4-Dihydroxyphenyl)-3,6,7-trihydroxy-4-oxochromen-5-olate
—— 3',4'-Dimethylmyricetin —— C17H13O8-
3',4'-Dimethylmyricetin
—— [(2R,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-7-oxo-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-5-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate —— C36H36O17
[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)-7-oxo-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-5-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
—— 5,7,8,3',4'-Pentahydroxyflavone —— C15H9O7-
5,7,8,3',4'-Pentahydroxyflavone
—— isorhamnetin 3-O-(6"-O-feruloyl)-glucoside —— C32H30O15
isorhamnetin 3-O-(6"-O-feruloyl)-glucoside
—— quercetin 3-O-gentiobioside-7-O-rhamnoside —— C33H40O21
quercetin 3-O-gentiobioside-7-O-rhamnoside
—— 8-(1,1)-Dimethylallyl-kaempferide —— C21H18O6-2
8-(1,1)-Dimethylallyl-kaempferide
—— 3,6,7,4'-tetramethylquercetagetin 3'-O-beta-D-glucoside —— C25H28O13
3,6,7,4'-tetramethylquercetagetin 3'-O-beta-D-glucoside
—— pelargonidin 3-O-(6"-O-malyl-beta-D-glucoside) —— C25H23O14-
pelargonidin 3-O-(6"-O-malyl-beta-D-glucoside)