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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
—— naringenin-7-methylether-4'-O-α-L-rhamnopyranoside 87489-96-1 C22H24O9
naringenin-7-methylether-4'-O-α-L-rhamnopyranoside
—— 5,7,3',4'-tetra-O-octanoylcatechin 904705-95-9 C47H70O10
5,7,3',4'-tetra-O-octanoylcatechin
—— 3',4',5,7-tetra-O-benzyl-8-iodocatechin 923565-01-9 C43H37IO6
3',4',5,7-tetra-O-benzyl-8-iodocatechin
—— 6-acetoxy-3',4',5,7-tetra-O-methyl-(+)-catechin 69152-83-6 C21H24O8
6-acetoxy-3',4',5,7-tetra-O-methyl-(+)-catechin
—— 3,3,6-tribromo-2-phenyl-chroman-4-one 100914-58-7 C15H9Br3O2
3,3,6-tribromo-2-phenyl-chroman-4-one
—— 3-(4-Bromobutoxy)-2-phenylchromen-4-one 114050-93-0 C19H17BrO3
3-(4-Bromobutoxy)-2-phenylchromen-4-one
—— 2-phenyl-8-(prop-2-en-1-yl)-7-(prop-2-en-1-yloxy)-4H-1-benzopyran-4-one 691008-31-8 C21H18O3
2-phenyl-8-(prop-2-en-1-yl)-7-(prop-2-en-1-yloxy)-4H-1-benzopyran-4-one
—— 6-(p-acetoxybenzyl)-3,3',4',5,7-penta-O-acetyl-(+)-catechin 81424-99-9 C34H32O13
6-(p-acetoxybenzyl)-3,3',4',5,7-penta-O-acetyl-(+)-catechin
—— 2-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3,5-triol 1242246-44-1 C49H42O9
2-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3,5-triol
—— 10-Methoxy-5,5-bis(4-methoxyphenyl)-11-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,2'-bicyclo[2.2.1]heptane] 1263318-61-1 C42H38O4S
10-Methoxy-5,5-bis(4-methoxyphenyl)-11-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,2'-bicyclo[2.2.1]heptane]
—— 2-[5-(3-benzoyl-4-oxo-4H-chromen-2-yl)furan-2-ylthio]acetic acid ethyl ester 1325215-30-2 C24H18O6S
2-[5-(3-benzoyl-4-oxo-4H-chromen-2-yl)furan-2-ylthio]acetic acid ethyl ester
—— 7-(2-{1-[4-(2-fluorophenyl)piperazin-1-yl]-2-oxopropylidene}hydrazinyl)-2-phenyl-4H-chromen-4-one 1394154-41-6 C28H25FN4O3
7-(2-{1-[4-(2-fluorophenyl)piperazin-1-yl]-2-oxopropylidene}hydrazinyl)-2-phenyl-4H-chromen-4-one
—— 3'-hydroxy-5,7,5',7'-tetramethoxy-2,2'-bis-(4-methoxy-phenyl)-2,3,2',3'-tetrahydro-[3,8']bichromenyl-4,4'-dione 18913-20-7 C36H34O11
3'-hydroxy-5,7,5',7'-tetramethoxy-2,2'-bis-(4-methoxy-phenyl)-2,3,2',3'-tetrahydro-[3,8']bichromenyl-4,4'-dione
—— 7-Methoxy-2-phenyl-8-(1-phenyl-allyl)-chromen-4-one 132314-50-2 C25H20O3
7-Methoxy-2-phenyl-8-(1-phenyl-allyl)-chromen-4-one
—— 9-hydroxy-4,8-dimethyl-5-phenyl-5H-pyrano<4,3,2-de><1,3>benzodioxin 105048-54-2 C18H16O4
9-hydroxy-4,8-dimethyl-5-phenyl-5H-pyrano<4,3,2-de><1,3>benzodioxin
—— ent-Fisetinidol-(4β,8)-catechin hepta-O-methyl ether 57499-11-3 C37H40O11
ent-Fisetinidol-(4β,8)-catechin hepta-O-methyl ether
—— (-)-fisetinidol-(4β,6)-(-)-fisetinidol-(4α,6)-(-)-fisetinidol-(4α,6)-(+)-epifisetinidol 102042-31-9 C60H50O20
(-)-fisetinidol-(4β,6)-(-)-fisetinidol-(4α,6)-(-)-fisetinidol-(4α,6)-(+)-epifisetinidol
—— penta-O-octanoylcatechin 904705-94-8 C55H84O11
penta-O-octanoylcatechin
—— (2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol 128428-25-1 C30H26O12
(2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,6']bichromenyl-3,5,7,3',5',7'-hexaol
—— cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(β-glucopyranosyl)-trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 1104564-17-1 C77H85O42
cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(β-glucopyranosyl)-trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]
—— [(2S,3S,4R,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate 1374991-31-7 C46H36O15
[(2S,3S,4R,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
—— (2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,8']bichromenyl-3,5,7,3',5',7'-hexaol 128428-22-8 C30H26O12
(2R,3R,4S,2'R,3'S)-4,2'-Bis-(3,4-dihydroxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[2,8']bichromenyl-3,5,7,3',5',7'-hexaol
—— tris-(2-phenyl-2,3-dihydrobenzopyran) 1384189-42-7 C33H30O3
tris-(2-phenyl-2,3-dihydrobenzopyran)
—— 3,4'-dimethoxy-7-hydroxyflavylium chloride 1092-22-4 C17H15O4*Cl
3,4'-dimethoxy-7-hydroxyflavylium chloride
—— 2-(2-(4-aminophenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl)acetic acid 1389342-12-4 C17H13NO5
2-(2-(4-aminophenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl)acetic acid
—— 5-hydroxy-2-(4-methoxy-2-((4-methoxybenzyl)oxy)phenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one 1216959-08-8 C34H34O7
5-hydroxy-2-(4-methoxy-2-((4-methoxybenzyl)oxy)phenyl)-8,8-dimethyl-3-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
—— 3'-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin 1037072-20-0 C27H34O16
3'-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin
—— (2R,3S)-2,3-trans-3-acetoxy-8-<(2R,3S)-2,3-trans-3-acetoxy-4',5,7-trimethoxyflavan-3'O-yl>-3',4',5,7-tetramethoxyflavan 114546-95-1 C41H44O14
(2R,3S)-2,3-trans-3-acetoxy-8-<(2R,3S)-2,3-trans-3-acetoxy-4',5,7-trimethoxyflavan-3'O-yl>-3',4',5,7-tetramethoxyflavan
—— (2R,3S)-2,3-trans-3-acetoxy-6-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl>-3',4',7,8-tetramethoxyflavan 89467-19-6 C42H46O14
(2R,3S)-2,3-trans-3-acetoxy-6-<(2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan-5-yl>-3',4',7,8-tetramethoxyflavan
—— 1-(4H-Chromen-4-on-2-yl)-4-(5,7-dimethoxychroman-4-on-2-yl)-benzol 118092-51-6 C26H20O6
1-(4H-Chromen-4-on-2-yl)-4-(5,7-dimethoxychroman-4-on-2-yl)-benzol
—— 2-(4-nitro-phenyl)-chroman-3,4-dione-3-oxime 107916-52-9 C15H10N2O5
2-(4-nitro-phenyl)-chroman-3,4-dione-3-oxime
—— 4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-3-phenyl-2H-chromen-6-ol hydrochloride 1352307-40-4 C30H33NO3*ClH
4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-3-phenyl-2H-chromen-6-ol hydrochloride
—— (1'S,4R)-7-bromo-6'-chloro-N-(3,5-dimethoxyphenyl)-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine 1418758-89-0 C24H21BrClNO4
(1'S,4R)-7-bromo-6'-chloro-N-(3,5-dimethoxyphenyl)-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine
—— 2,3-trans-3,4-cis-3',4',7-trimethoxy-4-(2,4,6-trimethoxyphenyl)flavan-3-ol 78215-67-5 C27H30O8
2,3-trans-3,4-cis-3',4',7-trimethoxy-4-(2,4,6-trimethoxyphenyl)flavan-3-ol
—— 2-(4-(2-(azepan-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol trifluoroacetate 1352307-13-1 C2HF3O2*C30H33NO4
2-(4-(2-(azepan-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol trifluoroacetate
—— 3,5,6,7,3'-Pentamethoxy-4'-benzyloxy-flavon 1063-06-5 C27H26O8
3,5,6,7,3'-Pentamethoxy-4'-benzyloxy-flavon
—— 1-[2-(4-{(2S,3R,4S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-oxo-3,4-dihydro-2H-4λ<sup>4</sup>-benzo[1,4]oxathiin-2-yl}-phenoxy)-ethyl]-piperidine 1-oxide 688329-80-8 C39H57NO6SSi2
1-[2-(4-{(2S,3R,4S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-oxo-3,4-dihydro-2H-4λ<sup>4</sup>-benzo[1,4]oxathiin-2-yl}-phenoxy)-ethyl]-piperidine 1-oxide
—— 2-[4-(5-Oxo-2,5-dihydro-furan-3-yl)-phenyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one 37636-74-1 C25H22O10
2-[4-(5-Oxo-2,5-dihydro-furan-3-yl)-phenyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one
—— Heptamethyl-dihydro-dehydro-dicatechin A 36048-12-1 C37H40O12
Heptamethyl-dihydro-dehydro-dicatechin A
—— 7-((4-fluorobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-5,6-diyl diacetate 1345982-10-6 C26H19FO7
7-((4-fluorobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-5,6-diyl diacetate
—— 7-hydroxy-2-phenyl-chromen-4-one; sodium salt 96634-58-1 C15H9O3*Na
7-hydroxy-2-phenyl-chromen-4-one; sodium salt
—— 2,3-trans-7,8,4'-trimethoxyflavan-3,4-cis-diol 213592-97-3 C18H20O6
2,3-trans-7,8,4'-trimethoxyflavan-3,4-cis-diol
—— (+)-catechin-5-O-β-glucuronide 242807-38-1 C21H22O12
(+)-catechin-5-O-β-glucuronide
—— (8S)-8-(2-chloro-4-fluorophenyl)-2,3-dimethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid 1046469-34-4 C19H16ClFN2O3
(8S)-8-(2-chloro-4-fluorophenyl)-2,3-dimethyl-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid
—— (2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol) 205645-53-0 C32H30O12
(2R,2'R,3S,3'S)-8,8'-(ethane-1,1-diyl)bis(2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol)
—— 3,6-Dibromo-7,4'-dimethoxyflavanon 38493-23-1 C17H14Br2O4
3,6-Dibromo-7,4'-dimethoxyflavanon
—— Acetic acid (1S,3S,4R,5S,8S)-4-acetoxy-3-[5-acetoxy-2-(4-acetoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-7-oxo-2,6-dioxa-bicyclo[3.2.1]oct-8-yl ester 34340-18-6 C29H24O14
Acetic acid (1S,3S,4R,5S,8S)-4-acetoxy-3-[5-acetoxy-2-(4-acetoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-7-oxo-2,6-dioxa-bicyclo[3.2.1]oct-8-yl ester
—— 2,6-diacetoxy-3-formyl-4-(5-oxo-2-phenyl-4,5-dihydro-3<i>H</i>-naphtho[1,8-<i>bc</i>]furan-4-ylmethyl)-benzoic acid methyl ester 32855-69-9 C31H24O9
2,6-diacetoxy-3-formyl-4-(5-oxo-2-phenyl-4,5-dihydro-3<i>H</i>-naphtho[1,8-<i>bc</i>]furan-4-ylmethyl)-benzoic acid methyl ester
—— trifolin heptaacetate 11055-94-0 C35H34O18
trifolin heptaacetate
—— 4''-benzyl-5,6-benzoflavanone 81414-84-8 C26H20O2
4''-benzyl-5,6-benzoflavanone