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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
—— (S)-3-acetyl-5-(hydroxymethyl)-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-one 1402841-91-1 C21H17N3O5
(S)-3-acetyl-5-(hydroxymethyl)-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-one
—— 1a-(4-chlorophenyl)-1,7a-dihydrocyclopropa[b]chromen-7-one 128814-94-8 C16H11ClO2
1a-(4-chlorophenyl)-1,7a-dihydrocyclopropa[b]chromen-7-one
—— 2-(3-benzyl-4-methoxyphenyl)-4H-chromen-4-one 1307886-93-6 C23H18O3
2-(3-benzyl-4-methoxyphenyl)-4H-chromen-4-one
—— 119002-89-0 C56H62O24
—— {(R)-2-methyl-1-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]ethyl}carbamic acid tert-butyl ester 728935-58-8 C30H35N3O5
{(R)-2-methyl-1-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]ethyl}carbamic acid tert-butyl ester
—— (2R)-2-(4-fluorophenyl)-4,7-dimethyl-2H-chromene 1273579-05-7 C17H15FO
(2R)-2-(4-fluorophenyl)-4,7-dimethyl-2H-chromene
—— 7,3-di-O-acetyl-5,3',4'-tri-O-benzyl-(+)-catechin 1007091-05-5 C40H36O8
7,3-di-O-acetyl-5,3',4'-tri-O-benzyl-(+)-catechin
—— 3-(2-fluoro-3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol 1352307-82-4 C30H32FNO4
3-(2-fluoro-3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol
—— 4-benzyl-2-phenyl(1,1-dichlorocyclopropa)<b>chroman 81635-52-1 C23H18Cl2O
4-benzyl-2-phenyl(1,1-dichlorocyclopropa)<b>chroman
—— 5R-(+)-[4-(2-diisopropylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol 554431-49-1 C31H35NO5
5R-(+)-[4-(2-diisopropylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol
—— (2R,3R)-2-(3,4-bis(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychromane-5,7-diyl bis(2-nitrobenzenesulfonate) 1186527-20-7 C39H26N4O22S4
(2R,3R)-2-(3,4-bis(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychromane-5,7-diyl bis(2-nitrobenzenesulfonate)
—— 8-methoxy-5S-(-)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-2-ol 554431-77-5 C31H33NO5
8-methoxy-5S-(-)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-2-ol
—— (7R,8R)-7-acetoxy-2-methyl-8-phenyl-3-propenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one 868634-27-9 C22H20N2O4
(7R,8R)-7-acetoxy-2-methyl-8-phenyl-3-propenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one
—— 2'-Methoxy-6-cyano-flavon 63070-94-0 C17H11NO3
2'-Methoxy-6-cyano-flavon
—— 2-(4-fluorophenyl)-7-hydroxychroman-4-one 127590-85-6 C15H11FO3
2-(4-fluorophenyl)-7-hydroxychroman-4-one
—— laricytrin 3,7,3'-tri-O-D-glucoside 89345-42-6 C34H42O23
laricytrin 3,7,3'-tri-O-D-glucoside
—— (5S)-3-acetyl-5-((R)-1-hydroxyethyl)-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-one 1402841-92-2 C22H19N3O5
(5S)-3-acetyl-5-((R)-1-hydroxyethyl)-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-one
—— (+)-3,5,7,3'-tetra-O-acetylcatechin 1209469-08-8 C23H22O10
(+)-3,5,7,3'-tetra-O-acetylcatechin
—— (-)-fisetinidol-(4α,8)-(+)-catechin hepta-O-methyl 57499-11-3 C37H40O11
(-)-fisetinidol-(4α,8)-(+)-catechin hepta-O-methyl
—— 1'-allyl-6-chloro-8-(4,5-diphenyl-1,3-oxazol-2-yl)-3',3'-dimethylspiro[2H-1-benzopyran-2,2'-indoline] 1236035-52-1 C36H29ClN2O2
1'-allyl-6-chloro-8-(4,5-diphenyl-1,3-oxazol-2-yl)-3',3'-dimethylspiro[2H-1-benzopyran-2,2'-indoline]
—— methyl 2-phenyl-2H-chromene-3-carboxylate 1300740-55-9 C17H14O3
methyl 2-phenyl-2H-chromene-3-carboxylate
—— (5S)-5-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol 554431-53-7 C27H27NO5
(5S)-5-[4-(2-dimethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol
—— 8-bromo-3-iodo-7-methoxy-2-phenyl-chromen-4-one 1279087-72-7 C16H10BrIO3
8-bromo-3-iodo-7-methoxy-2-phenyl-chromen-4-one
—— (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((3-(3-(3-nitrophenyl)-3-oxoprop-1-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 1224255-78-0 C32H29NO15
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((3-(3-(3-nitrophenyl)-3-oxoprop-1-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
—— methyl 9,11-bis(ethylcarbonato)-6aα,12aα-dihydro-6-oxo-1-phenylspiro<naphthaceno<1,12-bc>furan-12(6H,7H)-2'-<1,3>-dithiolan>-10-carboxylate 78752-90-6 C35H30O10S2
methyl 9,11-bis(ethylcarbonato)-6aα,12aα-dihydro-6-oxo-1-phenylspiro<naphthaceno<1,12-bc>furan-12(6H,7H)-2'-<1,3>-dithiolan>-10-carboxylate
—— benzyl [4-[(2R,3S)-3-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-2-yl]-2-phenylmethoxycarbonyloxyphenyl] carbonate 130659-29-9 C33H30O10
benzyl [4-[(2R,3S)-3-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-2-yl]-2-phenylmethoxycarbonyloxyphenyl] carbonate
—— 3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propionaldehyde 1157856-62-6 C38H50O6Si2
3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propionaldehyde
—— (2R,3S,4S)-2,3-trans-3,4-cis-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol 125136-15-4 C21H18O8
(2R,3S,4S)-2,3-trans-3,4-cis-4-(2,4-Dihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol
—— 5-[3-(Hexopyranosyloxy)-5,7-dihydroxy-1-benzopyran-1-ium-2-yl]-2-hydroxyphenolate--hydrogen chloride (1/1) 128808-27-5 C21H21ClO11
5-[3-(Hexopyranosyloxy)-5,7-dihydroxy-1-benzopyran-1-ium-2-yl]-2-hydroxyphenolate--hydrogen chloride (1/1)
—— Procyanidin trimer EEC 490-46-0 C45H38O18
Procyanidin trimer EEC
—— ent-epicatechin pentaacetate 94035-79-7 C25H24O11
ent-epicatechin pentaacetate
—— 2-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]-(R)-pyrrolidine-1-carboxylic acid tert-butyl ester 728935-80-6 C30H33N3O5
2-[6-(2-phenylchroman-6-yloxy)pyridin-3-ylcarbamoyl]-(R)-pyrrolidine-1-carboxylic acid tert-butyl ester
—— 6,8-dibromo-2'-hydroxyflavanone 107943-76-0 C15H10Br2O3
6,8-dibromo-2'-hydroxyflavanone
—— 1096657-76-9 C22H22O9
—— 5-Amino-2-{4-[N-(2-chloroethyl)]amino}phenyl-4H-benzopyran-4-one 130599-82-5 C17H15ClN2O2
5-Amino-2-{4-[N-(2-chloroethyl)]amino}phenyl-4H-benzopyran-4-one
—— (7R,8R)-7-hydroxy-2-methyl-8-phenyl-3-propenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one 868634-15-5 C20H18N2O3
(7R,8R)-7-hydroxy-2-methyl-8-phenyl-3-propenyl-7,8-dihydro-3H-chromeno[7,8-d]imidazol-6-one
—— 13-Methyl-10-oxa-benzo[g]chrysen-9-one 71644-62-7 C22H14O2
13-Methyl-10-oxa-benzo[g]chrysen-9-one
—— 2-(2-fluorophenyl)-4-oxo-4H-chromene-3-carbonitrile 1384106-90-4 C16H8FNO2
2-(2-fluorophenyl)-4-oxo-4H-chromene-3-carbonitrile
—— (+)-guibourtinidol-(4α,6)-(-)-fisetinidol 116145-84-7 C30H26O9
(+)-guibourtinidol-(4α,6)-(-)-fisetinidol
—— 3-Hydroxy-phloretin-4'-β-D-glucosid-octaacetat 4311-03-9 C37H40O19
3-Hydroxy-phloretin-4'-β-D-glucosid-octaacetat
—— 5,7-dimethoxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-2-[4-(1H-tetrazol-5-yl)-phenyl]-4H-benzopyran-4-one 358739-57-8 C24H25N5O5
5,7-dimethoxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-2-[4-(1H-tetrazol-5-yl)-phenyl]-4H-benzopyran-4-one
—— 7-Brom-4'-methoxy-flavonol 51409-96-2 C16H11BrO4
7-Brom-4'-methoxy-flavonol
—— 1,13-bis[4'-(5-methoxy-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane 958458-03-2 C40H38O11
1,13-bis[4'-(5-methoxy-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane
—— 8-bromo-7-butoxy-2-(4-methylphenyl)-6-nitrochromen-4-one 135878-81-8 C20H18BrNO5
8-bromo-7-butoxy-2-(4-methylphenyl)-6-nitrochromen-4-one
—— 7-methoxy-2-(4-methoxy-phenyl)-5-methyl-chroman-4-one 109557-82-6 C18H18O4
7-methoxy-2-(4-methoxy-phenyl)-5-methyl-chroman-4-one
—— 7-methoxy-2-(4-methoxy-phenyl)-6-nitro-chromen-4-one 109090-80-4 C17H13NO6
7-methoxy-2-(4-methoxy-phenyl)-6-nitro-chromen-4-one
—— (2R,3S,4R)-2,3-trans-3,4-cis-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',7-tetraol 78174-80-8 C21H18O8
(2R,3S,4R)-2,3-trans-3,4-cis-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',7-tetraol
—— (2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',5,7-pentamethoxy-4-(2,4-dimethoxyphenyl)flavan 78284-45-4 C28H32O8
(2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',5,7-pentamethoxy-4-(2,4-dimethoxyphenyl)flavan
—— 7-benzyloxy-6-n-pentyloxy flavone 203191-54-2 C27H26O4
7-benzyloxy-6-n-pentyloxy flavone
—— 7-benzyloxy-3',4',5-trimethoxy-6-n-pentyloxy flavone 203191-43-9 C30H32O7
7-benzyloxy-3',4',5-trimethoxy-6-n-pentyloxy flavone