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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
—— 2-(3,4-Dimethoxyphenyl)-2-ethoxy-5,7-dimethoxyspiro[chromene-3,2'-oxirane]-4-one 131190-69-7 C22H24O8
2-(3,4-Dimethoxyphenyl)-2-ethoxy-5,7-dimethoxyspiro[chromene-3,2'-oxirane]-4-one
—— 8.8''-Biflavonyl 1062-38-0 C30H18O4
8.8''-Biflavonyl
—— Quercetin 3,7,4'-triglucoside 133563-23-2 C33H40O22
Quercetin 3,7,4'-triglucoside
—— 4'-O-methylhypolaetin 8-O-β-D-glucopyranoside 80756-87-2 C22H22O12
4'-O-methylhypolaetin 8-O-β-D-glucopyranoside
—— (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-8-[(2S,3R,4S)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol —— C60H50O23
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-8-[(2S,3R,4S)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
—— 2-benzo[1,3]dioxol-5-yl-5,7-dimethyl-chromen-4-one 109697-02-1 C18H14O4
2-benzo[1,3]dioxol-5-yl-5,7-dimethyl-chromen-4-one
—— 2H-1-Benzopyran-3,4-diol, 3,4-dihydro-2-(4-hydroxyphenyl)-, [2S-(2I+/-,3I(2),4I(2))]- 149747-10-4 C15H14O4
2H-1-Benzopyran-3,4-diol, 3,4-dihydro-2-(4-hydroxyphenyl)-, [2S-(2I+/-,3I(2),4I(2))]-
—— 7-[(3,4-Di-O-acetyl-I(2)-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 84323-21-7 C25H24O12
7-[(3,4-Di-O-acetyl-I(2)-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
—— (1R,5S,7R,13R,20R)-11-hydroxy-5,10,13,14,15-pentamethoxy-7,20-diphenyl-2,8,21-trioxapentacyclo[11.8.0.01,17.03,12.04,9]henicosa-3,9,11,14,17-pentaen-16-one —— C35H34O10
(1R,5S,7R,13R,20R)-11-hydroxy-5,10,13,14,15-pentamethoxy-7,20-diphenyl-2,8,21-trioxapentacyclo[11.8.0.01,17.03,12.04,9]henicosa-3,9,11,14,17-pentaen-16-one
—— 4H-1-Benzopyran-4-one, 3-[[6-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-I(2)-D-glucopyranosyl]oxy]-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)- 157407-85-7 C33H38O20
4H-1-Benzopyran-4-one, 3-[[6-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-I(2)-D-glucopyranosyl]oxy]-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
—— Semiaquilinoside 64271-11-0 C28H32O14
Semiaquilinoside
—— 3-[(3-O-I(2)-D-Glucopyranosyl-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one 171828-59-4 C28H32O17
3-[(3-O-I(2)-D-Glucopyranosyl-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
—— Cyanidin 3-O-beta-(3''-O-beta-D-glucosyl-glucoside) 53696-63-2 C27H31O16+
Cyanidin 3-O-beta-(3''-O-beta-D-glucosyl-glucoside)
—— (2S,3R)-3-Chloro-2-(4-methoxy-phenyl)-3-nitro-chroman-4-one 143468-40-0 C16H12ClNO5
(2S,3R)-3-Chloro-2-(4-methoxy-phenyl)-3-nitro-chroman-4-one
—— Patuletin 3-(2''-apiosyl-[2'''-feruloylgentiobioside]) 195206-61-2 C43H48O25
Patuletin 3-(2''-apiosyl-[2'''-feruloylgentiobioside])
—— 2-(3,4-Dihydroxyphenyl)-3-[[2-O-[2-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one 151649-67-1 C42H46O25
2-(3,4-Dihydroxyphenyl)-3-[[2-O-[2-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one
—— 6,8-Diprenyleriodictyol 151649-32-0 C25H28O6
6,8-Diprenyleriodictyol
—— 2-(3,4-Dihydroxyphenyl)-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-3-[[2-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one 151649-66-0 C43H48O25
2-(3,4-Dihydroxyphenyl)-7-(I(2)-D-glucopyranosyloxy)-5-hydroxy-3-[[2-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one
—— (2S)-2,3-Dihydro-5,7-dihydroxy-8-(3-methyl-2-buten-1-yl)-2-(2,4,6-trimethoxyphenyl)-4H-1-benzopyran-4-one 156127-36-5 C23H26O7
(2S)-2,3-Dihydro-5,7-dihydroxy-8-(3-methyl-2-buten-1-yl)-2-(2,4,6-trimethoxyphenyl)-4H-1-benzopyran-4-one
—— Eriodictin 480-35-3 C21H22O10
Eriodictin
—— 3-(4-methoxyphenyl)-3-(naphthalen-1-yl)-3H-benzo[f]chromene 1235387-71-9 C30H22O2
3-(4-methoxyphenyl)-3-(naphthalen-1-yl)-3H-benzo[f]chromene
—— (2R,3S)-2-(3-fluoro-4-hydroxyphenyl)chroman-3,5,7-triol 1256550-83-0 C15H13FO5
(2R,3S)-2-(3-fluoro-4-hydroxyphenyl)chroman-3,5,7-triol
—— N,N-dimethyl-4-(3-phenylbenzo[f]chromen-3-yl)naphthalen-1-amine 1296845-70-9 C31H25NO
N,N-dimethyl-4-(3-phenylbenzo[f]chromen-3-yl)naphthalen-1-amine
—— (2S,3R,4S,5S,6R)-2-[[11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-[1-[11-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-oxa-2-oxoniatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,9,11-hexaen-3-yl]ethylidene]-2,8-dioxatricyclo[7.3.1.05,13]trideca-1(12),3,5,9(13),10-pentaen-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 1311158-31-2 C52H51O24
(2S,3R,4S,5S,6R)-2-[[11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-[1-[11-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-oxa-2-oxoniatricyclo[7.3.1.05,13]trideca-1(13),2,4,6,9,11-hexaen-3-yl]ethylidene]-2,8-dioxatricyclo[7.3.1.05,13]trideca-1(12),3,5,9(13),10-pentaen-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— [(2R,3S)-2-[3,4-bis(2,2,2-trichloroethoxysulfonyloxy)phenyl]-3-hydroxy-5-(2,2,2-trichloroethoxysulfonyloxy)-3,4-dihydro-2H-chromen-7-yl] 2,2,2-trichloroethyl sulfate 1313434-36-4 C23H18Cl12O18S4
[(2R,3S)-2-[3,4-bis(2,2,2-trichloroethoxysulfonyloxy)phenyl]-3-hydroxy-5-(2,2,2-trichloroethoxysulfonyloxy)-3,4-dihydro-2H-chromen-7-yl] 2,2,2-trichloroethyl sulfate
—— 6,8-dichloro-2-phenyl-2H-chromene 1017832-15-3 C15H10Cl2O
6,8-dichloro-2-phenyl-2H-chromene
—— 6-Chloro-2-phenyl-3-prop-2-ynoxychromen-4-one 1037268-13-5 C18H11ClO3
6-Chloro-2-phenyl-3-prop-2-ynoxychromen-4-one
—— 9-chloro-5-ethynyl-5H-isochromeno[4,3-b]chromen-7-one 1037268-32-8 C18H9ClO3
9-chloro-5-ethynyl-5H-isochromeno[4,3-b]chromen-7-one
—— 5,7-di(benzyloxy)-3',4'-dimethoxyflavone 383368-93-2 C31H26O6
5,7-di(benzyloxy)-3',4'-dimethoxyflavone
—— Kaempferol 3-O-sophoroside 7-O-glucuronide 140163-56-0 C33H38O22
Kaempferol 3-O-sophoroside 7-O-glucuronide
—— bis(3,5,7,3',4'-Penta-O-benzyl-8-catechinyl)methane 1599460-40-8 C101H88O12
bis(3,5,7,3',4'-Penta-O-benzyl-8-catechinyl)methane
—— 5,7-dihydroxy-6-[(2S,3R,4R,6S)-4-hydroxy-6-methyl-5-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-2-(4-hydroxyphenyl)chromen-4-one —— C27H28O13
5,7-dihydroxy-6-[(2S,3R,4R,6S)-4-hydroxy-6-methyl-5-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-2-(4-hydroxyphenyl)chromen-4-one
—— Tricin 7-O-glucuronide 32769-02-1 C23H22O13
Tricin 7-O-glucuronide
—— 1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-phenyl- 31018-48-1 C21H24O9
1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-phenyl-
—— (1R,8S,9R,16R,18S,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.01,13.03,12.06,11.018,27.020,25]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one —— C30H24O12
(1R,8S,9R,16R,18S,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.01,13.03,12.06,11.018,27.020,25]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one
—— 4H-1-Benzopyran-4-one, 3-[(O-D-apio-I(2)-D-furanosyl-(1a2)-O-[6-deoxy-I+/--L-mannopyranosyl-(1a6)]-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)- 165605-18-5 C33H40O20
4H-1-Benzopyran-4-one, 3-[(O-D-apio-I(2)-D-furanosyl-(1a2)-O-[6-deoxy-I+/--L-mannopyranosyl-(1a6)]-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
—— 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[[O-6-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl-(1a2)-O-I(2)-D-galactopyranosyl-(1a2)-I(2)-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one 197294-29-4 C43H48O25
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[[O-6-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl-(1a2)-O-I(2)-D-galactopyranosyl-(1a2)-I(2)-D-glucopyranosyl]oxy]-4H-1-benzopyran-4-one
—— 3-[(O-I(2)-D-Glucopyranosyl-(1a2)-O-I(2)-D-galactopyranosyl-(1a2)-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 197250-98-9 C33H40O21
3-[(O-I(2)-D-Glucopyranosyl-(1a2)-O-I(2)-D-galactopyranosyl-(1a2)-I(2)-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
—— Petunidin 3-rutinoside 39824-84-5 C28H33O16+
Petunidin 3-rutinoside
—— Kaempferol 7-O-alpha-L-rhamnopyranoside-4'-O-beta-D-glucopyranoside 205876-37-5 C27H30O15
Kaempferol 7-O-alpha-L-rhamnopyranoside-4'-O-beta-D-glucopyranoside
—— [(2S)-2-phenyl-2H-chromen-4-yl] 2,2-dimethylpropanoate 1318697-95-8 C20H20O3
[(2S)-2-phenyl-2H-chromen-4-yl] 2,2-dimethylpropanoate
—— 4-(3-naphthalen-1-ylbenzo[f]chromen-3-yl)-N,N-diphenylaniline 1327154-59-5 C41H29NO
4-(3-naphthalen-1-ylbenzo[f]chromen-3-yl)-N,N-diphenylaniline
—— 5-Hydroxycastavinol 183607-17-2 C26H30O14
5-Hydroxycastavinol
—— (1S,5S,13R)-9,19-dimethoxy-18-methyl-5,13-diphenyl-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-17,21-diol —— C33H30O7
(1S,5S,13R)-9,19-dimethoxy-18-methyl-5,13-diphenyl-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-17,21-diol
—— Castavinol 183607-09-2 C26H30O13
Castavinol
—— 1-[(2S,5S,10R)-10-(I(2)-D-Glucopyranosyloxy)-4,5-dihydro-6,8-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-methyl-2,5-methano-1,3-benzodioxepin-4-yl]ethanone 183607-16-1 C27H32O14
1-[(2S,5S,10R)-10-(I(2)-D-Glucopyranosyloxy)-4,5-dihydro-6,8-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-methyl-2,5-methano-1,3-benzodioxepin-4-yl]ethanone
—— (2S)-2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6,8-dimethyl-4H-1-benzopyran-4-one 551-99-5 C18H18O5
(2S)-2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6,8-dimethyl-4H-1-benzopyran-4-one
—— 1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-5-(I(2)-D-glucopyranosyloxy)-7-hydroxy-3-[[2-O-[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]- 307318-06-5 C42H47O23+
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-5-(I(2)-D-glucopyranosyloxy)-7-hydroxy-3-[[2-O-[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-I(2)-D-glucopyranosyl]-I(2)-D-glucopyranosyl]oxy]-
—— 3-O-[3-[2-(3,5-ditert-butyl-4-hydroxyphenyl)-4-oxochromen-7-yl]oxypropyl] 1-O-methyl propanedioate 1103807-01-7 C30H36O8
3-O-[3-[2-(3,5-ditert-butyl-4-hydroxyphenyl)-4-oxochromen-7-yl]oxypropyl] 1-O-methyl propanedioate
—— 2-(2-bromophenyl)-2H-chromene 1253197-94-2 C15H11BrO
2-(2-bromophenyl)-2H-chromene