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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
—— 4H-1-Benzopyran-4-one, 6,8-di-I(2)-D-glucopyranosyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2R)- 81446-26-6 C27H32O15
4H-1-Benzopyran-4-one, 6,8-di-I(2)-D-glucopyranosyl-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2R)-
—— (2R,3R)-3-hydroxy-5-methoxy-6,7-methylenedioxy-flavanone 83532-20-1 C17H14O6
(2R,3R)-3-hydroxy-5-methoxy-6,7-methylenedioxy-flavanone
—— 5-hydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one 20056-21-7 C33H40O20
5-hydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
—— 7-O-(6-O-acetyl-β-allopyranosyl)-4'-O-(β-allopyranosyl)apigenin 95690-52-1 C29H32O16
7-O-(6-O-acetyl-β-allopyranosyl)-4'-O-(β-allopyranosyl)apigenin
—— 3-[(2-O-D-Apio-I(2)-D-furanosyl-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 99816-59-8 C26H28O15
3-[(2-O-D-Apio-I(2)-D-furanosyl-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
—— 8-Methoxy-3-phenyl-1H-naphtho[2,1-b]pyran-1-one 89504-54-1 C20H14O3
8-Methoxy-3-phenyl-1H-naphtho[2,1-b]pyran-1-one
—— [(2S,3R,4S,5R,6R)-3-acetyloxy-5-hydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-4-yl] acetate 84323-20-6 C25H24O12
[(2S,3R,4S,5R,6R)-3-acetyloxy-5-hydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-4-yl] acetate
—— Rubraflavone A 54510-13-3 C25H26O5
Rubraflavone A
—— 2-(2,6-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-1-benzopyran-4-one 61862-70-2 C20H20O7
2-(2,6-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-1-benzopyran-4-one
—— Rhamnazin-3-O-β-isorhamninosid-deca-O-acetat 52801-25-9 C55H64O30
Rhamnazin-3-O-β-isorhamninosid-deca-O-acetat
—— (2R,3R,4S)-2,3-cis-3,4-trans-4-ethoxy-3,3',4',7,8-pentahydroxyflavan 104806-83-9 C17H18O7
(2R,3R,4S)-2,3-cis-3,4-trans-4-ethoxy-3,3',4',7,8-pentahydroxyflavan
—— Patuletin 3-glucosyl-(1a6)[apiosyl(1a2)]glucoside 101021-30-1 C33H40O22
Patuletin 3-glucosyl-(1a6)[apiosyl(1a2)]glucoside
—— Rhamnocitrin-3-O-β-rhamninosid-deca-O-acetat 73519-13-8 C54H62O29
Rhamnocitrin-3-O-β-rhamninosid-deca-O-acetat
—— (-)-8'-O-β-D-glucopyranosyl-12a-hydroxyamorphigenin 68401-03-6 C29H32O13
(-)-8'-O-β-D-glucopyranosyl-12a-hydroxyamorphigenin
—— [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate 102231-39-0 C36H36O17
[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
—— Patuletin 3-O-I(2)-gentiobioside 101021-28-7 C28H32O18
Patuletin 3-O-I(2)-gentiobioside
—— 5,6,7,8,2',6'-hexamethoxyflavone 74670-18-1 C21H22O8
5,6,7,8,2',6'-hexamethoxyflavone
—— 8-Glucopyranosylprocyanidin B1 105371-28-6 C36H36O17
8-Glucopyranosylprocyanidin B1
—— 6-Glucopyranosylprocyanidin B1 105371-29-7 C36H36O17
6-Glucopyranosylprocyanidin B1
—— 3,4'-di-O-β-D-glucosyl-7-O-β-D-(2-O-feruloyl)glucosylkaempferol 108887-46-3 C43H48O24
3,4'-di-O-β-D-glucosyl-7-O-β-D-(2-O-feruloyl)glucosylkaempferol
—— (1R,5R,6S,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol 111466-35-4 C37H38O12
(1R,5R,6S,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol
—— 3-O-β-D-(2-O-feruloyl)glucosyl-7,4'-di-O-β-D-glucosylkaempferol 108887-47-4 C43H48O24
3-O-β-D-(2-O-feruloyl)glucosyl-7,4'-di-O-β-D-glucosylkaempferol
—— 3-O-β-sophorosyl-7-O-β-D-(6O-feruloyl)glucosylkaempferol 87891-34-7 C43H48O24
3-O-β-sophorosyl-7-O-β-D-(6O-feruloyl)glucosylkaempferol
—— 5,3'-di-O-methyl-(-)-epicatechin 97914-18-6 C17H18O6
5,3'-di-O-methyl-(-)-epicatechin
—— (2S,3R)-2-Naphthalen-1-yl-3,6-dinitro-chroman 112513-92-5 C19H14N2O5
(2S,3R)-2-Naphthalen-1-yl-3,6-dinitro-chroman
—— (2S,3S)-2-(3,4-Diethoxy-phenyl)-chroman-3-ylamine 112514-08-6 C19H23NO3
(2S,3S)-2-(3,4-Diethoxy-phenyl)-chroman-3-ylamine
—— (2S,3R)-6-Chloro-2-naphthalen-1-yl-3-nitro-chroman 112513-91-4 C19H14ClNO3
(2S,3R)-6-Chloro-2-naphthalen-1-yl-3-nitro-chroman
—— N-[(2S,3S)-2-(3,4-Diethoxy-phenyl)-chroman-3-yl]-hydroxylamine 112513-98-1 C19H23NO4
N-[(2S,3S)-2-(3,4-Diethoxy-phenyl)-chroman-3-yl]-hydroxylamine
—— 2-phenyl-3-amino-2H-1-benzopyran 112514-01-9 C15H15NO
2-phenyl-3-amino-2H-1-benzopyran
—— 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-[[2-O-[5-O-[(2E)-1-oxo-3-phenyl-2-propen-1-yl]-D-apio-beta-D-furanosyl]-beta-D-glucopyranosyl]oxy]-2-phenyl- 773899-29-9 C35H36O14
4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-[[2-O-[5-O-[(2E)-1-oxo-3-phenyl-2-propen-1-yl]-D-apio-beta-D-furanosyl]-beta-D-glucopyranosyl]oxy]-2-phenyl-
—— salcolin B 369390-51-2 C27H26O11
salcolin B
—— salcolin B 369390-52-3 C27H26O11
salcolin B
—— 4-(7-hydroxy-4-oxo-8-propyl-4H-1-benzopyran-2-yl)-benzoic acid 57161-95-2 C19H16O5
4-(7-hydroxy-4-oxo-8-propyl-4H-1-benzopyran-2-yl)-benzoic acid
—— 3-(4-Methoxyphenyl)-3-(2-methylphenyl)-3H-naphtho[2,1-b]pyran 138947-55-4 C27H22O2
3-(4-Methoxyphenyl)-3-(2-methylphenyl)-3H-naphtho[2,1-b]pyran
—— 3-(2,6-Difluorophenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran 138947-57-6 C26H18F2O2
3-(2,6-Difluorophenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran
—— 2-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one 134611-70-4 C17H13NO6
2-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one
—— 5,7,8-Trimethyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-2,6-diol 53713-18-1 C18H20O3
5,7,8-Trimethyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-2,6-diol
—— 4,5-dihydroxy-3,7-dimethoxyflavan 1227479-75-5 C17H18O5
4,5-dihydroxy-3,7-dimethoxyflavan
—— Muscadinin 25846-73-5 C28H33O17+
Muscadinin
—— Hexanamide, 2,6-diamino-N-(4-(5-amino-6,8-difluoro-7-methyl-4-oxo-4H-1-benzopyran-2-yl)-2-fluorophenyl)-, (2S)-, dimethanesulfonate 468719-53-1 C24H31F3N4O9S2
Hexanamide, 2,6-diamino-N-(4-(5-amino-6,8-difluoro-7-methyl-4-oxo-4H-1-benzopyran-2-yl)-2-fluorophenyl)-, (2S)-, dimethanesulfonate
—— 2,2-dimethyl-propionic acid 8-(2,2-dimethyl-propionyloxy)-11-methyl-11-[3-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester 554431-12-8 C40H47NO7
2,2-dimethyl-propionic acid 8-(2,2-dimethyl-propionyloxy)-11-methyl-11-[3-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester
—— 2,2-dimethyl-propionic acid 8-(2,2-dimethyl-propionyloxy)-11-methyl-11-[4-(3-piperidin-1-yl-propoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester 554431-11-7 C41H49NO7
2,2-dimethyl-propionic acid 8-(2,2-dimethyl-propionyloxy)-11-methyl-11-[4-(3-piperidin-1-yl-propoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromen-2-yl ester
—— Peonidin 3-lathyroside 155380-00-0 C27H31O15+
Peonidin 3-lathyroside
—— Malvidin 3-sophoroside 5-glucoside 61811-04-9 C35H45O22+
Malvidin 3-sophoroside 5-glucoside
—— Delphinidin 3-sophoroside-5-glucoside 36547-37-2 C33H41O22+
Delphinidin 3-sophoroside-5-glucoside
—— Cyanidin 3-(6''-(E)-p-coumarylsambubioside) 5-glucoside 163060-00-2 C41H45O22+
Cyanidin 3-(6''-(E)-p-coumarylsambubioside) 5-glucoside
—— 2-[2-[5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 55463-07-5 C29H35O17+
2-[2-[5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
—— Sambicyanin 33012-73-6 C26H29O15+
Sambicyanin
—— Delphinidin-3-O-sambubioside 53158-73-9 C26H29O16+
Delphinidin-3-O-sambubioside
—— 2-[4-[5,7-Dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-2-yl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 27459-78-5 C27H31O16+
2-[4-[5,7-Dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-2-yl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol