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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
—— (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dibutyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran —— C24H30O6
(6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dibutyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran
—— tetra-O-benzyl (+)-catechin —— C43H38O6
tetra-O-benzyl (+)-catechin
—— (2R,3R)-2-(3,4-dihydroxyphenyl)-3-fluorochroman-5,7-diol —— C15H13FO5
(2R,3R)-2-(3,4-dihydroxyphenyl)-3-fluorochroman-5,7-diol
—— dehydrodicatechin A —— C30H24O12
dehydrodicatechin A
—— procyanidin B-3 3'-O-β-D-glucopyranoside —— C36H36O17
procyanidin B-3 3'-O-β-D-glucopyranoside
—— (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dipropyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran —— C22H26O6
(6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-dipropyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran
—— (6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-diethyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran —— C20H22O6
(6aS,12aR)-6a,12a-trans-2,3,8,10-tetrahydroxy-5,5-diethyl-5,6a,7,12a-tetrahydro-[1]benzopyrano[3,2-c][2]benzopyran
—— catechin-(4α-8)-epicatechin-(4β-8)-catechin —— C45H38O18
catechin-(4α-8)-epicatechin-(4β-8)-catechin
—— (+)-catechin-5-O-β-D-(2'-O-galloyl)-glucopyranoside —— C28H28O15
(+)-catechin-5-O-β-D-(2'-O-galloyl)-glucopyranoside
—— (-)-epicatechin-4β-dodecylsulfide —— C27H38O6S
(-)-epicatechin-4β-dodecylsulfide
—— PZ-5 —— C75H62O31
PZ-5
—— 3-O-(1-hydroxy-6-oxo-2-cyclohexene-1-carboxylic acid ester) of (+)-catechin —— C22H20O9
3-O-(1-hydroxy-6-oxo-2-cyclohexene-1-carboxylic acid ester) of (+)-catechin
—— phylloflavan —— C26H26O10
phylloflavan
—— isovitexin 7-O-glucoside 2''-O-rhamnoside —— C33H40O19
isovitexin 7-O-glucoside 2''-O-rhamnoside
—— isorhamnetin 3-O-[β-D-xylopyranosyl(1->3)-α-L-rhamnopyranosyl(1->6)]-β-D-galactopyranoside 7-O-α-L-rhamnopyranoside —— C39H50O24
isorhamnetin 3-O-[β-D-xylopyranosyl(1->3)-α-L-rhamnopyranosyl(1->6)]-β-D-galactopyranoside 7-O-α-L-rhamnopyranoside
—— myricetin 3-O-β-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->2)-α-L-rhamnopyranoside —— C33H40O22
myricetin 3-O-β-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->2)-α-L-rhamnopyranoside
—— 8-(β-lactosyl)naringenin —— C27H32O15
8-(β-lactosyl)naringenin
—— 7-[2-(1H-1-Imidazolyl)ethoxy]-2-phenyl-4-chromanone —— C20H18N2O3
7-[2-(1H-1-Imidazolyl)ethoxy]-2-phenyl-4-chromanone
—— (+/-)-cis-4-(benzo[d][1,3]dioxol-5-yl)-6-chloro-5,7-dimethyl-2-phenylchroman —— C24H21ClO3
(+/-)-cis-4-(benzo[d][1,3]dioxol-5-yl)-6-chloro-5,7-dimethyl-2-phenylchroman
—— 2'-(3,4-dihydroxyphenyl)-3',5',7'-trihydroxy-7-methoxy-2H,4'H-[6,8'-bibenzopyran]-2,4'-dione —— C25H16O10
2'-(3,4-dihydroxyphenyl)-3',5',7'-trihydroxy-7-methoxy-2H,4'H-[6,8'-bibenzopyran]-2,4'-dione
—— 2-(3-ethoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one —— C17H14O7
2-(3-ethoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
—— 5,5′-((1,4-phenylenebis(methylene))bis(oxy))bis(2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one) —— C38H26O14
5,5′-((1,4-phenylenebis(methylene))bis(oxy))bis(2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one)
—— 4'-O-n-hexadecyl-3,3',4',5,7-pentahydroxyflavone —— C31H42O7
4'-O-n-hexadecyl-3,3',4',5,7-pentahydroxyflavone
—— 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromene-4-selenone —— C19H18O6Se
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromene-4-selenone
—— 2-(3,4-diethoxyphenyl)-3,7-diethoxy-5-hydroxy-6-iodo-4H-chromen-4-one —— C23H25IO7
2-(3,4-diethoxyphenyl)-3,7-diethoxy-5-hydroxy-6-iodo-4H-chromen-4-one
—— (S)-2-((((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)carbonyl)amino)pentanedioic acid —— C21H17NO12
(S)-2-((((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)carbonyl)amino)pentanedioic acid
—— 3'-tert-butyloxycarbonyl-D-alanine tetraacetylquercetin ester —— C31H31NO14
3'-tert-butyloxycarbonyl-D-alanine tetraacetylquercetin ester
—— 3'-[cis-4-(tert-butyloxycarbonyl-amino)cyclohexanecarboxylic acid] tetraacetylquercetin ester —— C35H37NO14
3'-[cis-4-(tert-butyloxycarbonyl-amino)cyclohexanecarboxylic acid] tetraacetylquercetin ester
—— quercetin-5-O-sulphate —— C15H10O10S
quercetin-5-O-sulphate
—— 6-((benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one —— C24H21NO7
6-((benzyl(methyl)amino)methyl)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
—— 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one —— C15H10O7
3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one
—— 2-(3',4'-dihydroxyphenyl)-3,7-dihydroxy-4-oxo-4H-chromen-5-yl octanoate —— C23H24O8
2-(3',4'-dihydroxyphenyl)-3,7-dihydroxy-4-oxo-4H-chromen-5-yl octanoate
—— 7-O-n-dodecyl-3,3',4',5,7-pentahydroxyflavone —— C27H34O7
7-O-n-dodecyl-3,3',4',5,7-pentahydroxyflavone
—— 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-(morpholinomethyl)-4H-chromen-4-one —— C20H19NO8
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-(morpholinomethyl)-4H-chromen-4-one
—— 3′,4,5,7-tetrahydroxyflavone-3-yldocosa-4,7,10,13,16,19-hexaenoate —— C37H40O8
3′,4,5,7-tetrahydroxyflavone-3-yldocosa-4,7,10,13,16,19-hexaenoate
—— quercetin-3-O-hexanoate —— C21H20O8
quercetin-3-O-hexanoate
—— quercetin-3-O-heptanoate —— C22H22O8
quercetin-3-O-heptanoate
—— quercetin-3-O-nonanoate —— C24H26O8
quercetin-3-O-nonanoate
—— 7-O-glucuronosyl quercetin —— C21H18O13
7-O-glucuronosyl quercetin
—— quercetin-3'-O-glucuronide —— C21H18O13
quercetin-3'-O-glucuronide
—— quercetin 3-O-glucuronide —— C21H18O13
quercetin 3-O-glucuronide
—— quercetin-3'-glucuronide —— C21H18O13
quercetin-3'-glucuronide
—— 3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one —— C37H30O7
3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one
—— 2-(3',4'-dihydroxyphenyl)-5-hydroxy-3,7-di-(β-D-tetraacetylgalactosyl)-4H-chromen-4-one —— C43H46O25
2-(3',4'-dihydroxyphenyl)-5-hydroxy-3,7-di-(β-D-tetraacetylgalactosyl)-4H-chromen-4-one
—— 2-(3',4'-dihydroxyphenyl)-5,7-dihydroxy-3-β-L-fucosyl-4H-chromen-4-one —— C21H20O11
2-(3',4'-dihydroxyphenyl)-5,7-dihydroxy-3-β-L-fucosyl-4H-chromen-4-one
—— 3'-D-alanine tetraacetylquercetin ester hydrochloride —— C26H23NO12*ClH
3'-D-alanine tetraacetylquercetin ester hydrochloride
—— 3'-[cis-4-aminocyclohexanecarboxylic acid] tetraacetylquercetin ester hydrochloride —— C30H29NO12*ClH
3'-[cis-4-aminocyclohexanecarboxylic acid] tetraacetylquercetin ester hydrochloride
—— 8-(furfurylaminomethyl)quercetin —— C21H17NO8
8-(furfurylaminomethyl)quercetin
—— 8-(3-fluorobenzylaminomethyl)quercetin —— C23H18FNO7
8-(3-fluorobenzylaminomethyl)quercetin
—— orientin —— C21H20O12
orientin