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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
—— (2R)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-one 1607010-91-2 C36H30O5
(2R)-2-(3-benzyloxyphenyl)-5,7-dibenzyloxy-chroman-3-one
—— 2-(2-<i>sec</i>-butoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 66848-77-9 C20H18O5
2-(2-<i>sec</i>-butoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— 1172118-65-8 C29H31N3O4
—— okanin 4'-O-(2"-O-caffeoyl-6"-O-p-coumaroyl-β-D-glucopyranoside) 142628-31-7 C39H34O16
okanin 4'-O-(2"-O-caffeoyl-6"-O-p-coumaroyl-β-D-glucopyranoside)
—— (1-methoxy-6-(3-chlorophenyl)-6H-dibenzo(b,d)pyran-8-yl)-N,N-dimethylthiourea 373630-59-2 C23H21ClN2O2S
(1-methoxy-6-(3-chlorophenyl)-6H-dibenzo(b,d)pyran-8-yl)-N,N-dimethylthiourea
—— 2-(2-Chloro-phenyl)-4-oxo-4H-chromene-6-carboxylic acid 66848-74-6 C16H9ClO4
2-(2-Chloro-phenyl)-4-oxo-4H-chromene-6-carboxylic acid
—— 2-(3,5-Diisopropoxy-phenyl)-5,7-diisopropoxy-chroman-4-one 216700-54-8 C27H36O6
2-(3,5-Diisopropoxy-phenyl)-5,7-diisopropoxy-chroman-4-one
—— 4-O-methylokanin 4'-O-(6"-O-acetyl-2"-O-caffeoyl-β-D-glucopyranoside) 142628-34-0 C33H32O15
4-O-methylokanin 4'-O-(6"-O-acetyl-2"-O-caffeoyl-β-D-glucopyranoside)
—— 4-chloro-5-ethoxy-3-methylidene-2-phenyl-1-benzoxepine 111861-96-2 C19H17ClO2
4-chloro-5-ethoxy-3-methylidene-2-phenyl-1-benzoxepine
—— 6,6''-Biflavonyloxymethan 40316-65-2 C31H20O6
6,6''-Biflavonyloxymethan
—— (E)-N-cyclohexyl-3-(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)acrylamide 1412411-05-2 C24H23NO5
(E)-N-cyclohexyl-3-(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)acrylamide
—— Acetic acid 2-[2,4-diacetoxy-5-((E)-3,7-dimethyl-octa-2,6-dienyl)-phenyl]-5-hydroxy-4-oxo-chroman-7-yl ester 68401-04-7 C31H34O9
Acetic acid 2-[2,4-diacetoxy-5-((E)-3,7-dimethyl-octa-2,6-dienyl)-phenyl]-5-hydroxy-4-oxo-chroman-7-yl ester
—— Morusin-triacetat 62596-32-1 C31H30O9
Morusin-triacetat
—— 7-acetoxy-6,3',4',5'-tetramethoxyflavone 75672-56-9 C21H20O8
7-acetoxy-6,3',4',5'-tetramethoxyflavone
—— (2<i>R</i>)-3<i>t</i>-acetoxy-2<i>r</i>-(3,4-bis-methanesulfonyloxy-phenyl)-5,7-bis-methanesulfonyloxy-chroman 115248-91-4 C21H24O15S4
(2<i>R</i>)-3<i>t</i>-acetoxy-2<i>r</i>-(3,4-bis-methanesulfonyloxy-phenyl)-5,7-bis-methanesulfonyloxy-chroman
—— 8-dimethylallylsteppogenin 152464-78-3 C20H20O6
8-dimethylallylsteppogenin
—— 3,6,8-Tribromo-2-(4-chloro-phenyl)-chroman-4-one 102260-68-4 C15H8Br3ClO2
3,6,8-Tribromo-2-(4-chloro-phenyl)-chroman-4-one
—— 6,8-Dibrom-5-acetoxy-flavon 93191-71-0 C17H10Br2O4
6,8-Dibrom-5-acetoxy-flavon
—— ent-epiafzelechin-(2α->7,4α->8)-epiafzelechin 7,12,5',12'-tetramethyl ether-3,5,3'-triacetate 142382-29-4 C40H38O13
ent-epiafzelechin-(2α->7,4α->8)-epiafzelechin 7,12,5',12'-tetramethyl ether-3,5,3'-triacetate
—— 3-hydroxypropyl 9-methoxy-2-(4-methoxyphenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate 1188494-61-2 C31H28O6
3-hydroxypropyl 9-methoxy-2-(4-methoxyphenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate
—— 6-chloro-2-(4-(phenylthio)phenyl)-4H-chromen-4-one 1360145-35-2 C21H13ClO2S
6-chloro-2-(4-(phenylthio)phenyl)-4H-chromen-4-one
—— 4-Methoxy-benzoic acid 2-{2-[5-(5,7-dimethoxy-4-oxo-4H-chromen-2-yl)-2-methoxy-phenyl]-acetyl}-3,5-dimethoxy-phenyl ester 63557-77-7 C36H32O11
4-Methoxy-benzoic acid 2-{2-[5-(5,7-dimethoxy-4-oxo-4H-chromen-2-yl)-2-methoxy-phenyl]-acetyl}-3,5-dimethoxy-phenyl ester
—— epiafzelechin-(4β->8,2β->O->7)-epicatechin-(4α->8)-epicatechin 130918-28-4 C45H36O17
epiafzelechin-(4β->8,2β->O->7)-epicatechin-(4α->8)-epicatechin
—— (1R,5R,6S,7S,13S,21R)-7-benzylsulfanyl-5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol 130918-32-0 C37H30O11S
(1R,5R,6S,7S,13S,21R)-7-benzylsulfanyl-5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
—— 4''-benzyloxy-3-α-hydroxybenzylflavone 119139-31-0 C29H22O4
4''-benzyloxy-3-α-hydroxybenzylflavone
—— 2-benzo[1,3]dioxol-5-yl-8-bromo-3-hydroxy-6-methyl-chromen-4-one 93261-76-8 C17H11BrO5
2-benzo[1,3]dioxol-5-yl-8-bromo-3-hydroxy-6-methyl-chromen-4-one
—— 2-(4-benzyloxy-phenyl)-3,5,7,8-tetramethoxy-chromen-4-one 6601-75-8 C26H24O7
2-(4-benzyloxy-phenyl)-3,5,7,8-tetramethoxy-chromen-4-one
—— 3-(4-methoxyphenyl)-2-nitro-3H-benzo[f]chromene 134272-37-0 C20H15NO4
3-(4-methoxyphenyl)-2-nitro-3H-benzo[f]chromene
—— 4',4'''-Dimethylcuppressuflavanone 115900-09-9 C32H26O10
4',4'''-Dimethylcuppressuflavanone
—— Z-3-(α-methylbenzylidene)-flavanone 138421-98-4 C23H18O2
Z-3-(α-methylbenzylidene)-flavanone
—— 6,8-Dibrom-5-hydroxy-3'-methoxy-7,4'-diacetoxy-flavanon 3162-20-7 C20H16Br2O8
6,8-Dibrom-5-hydroxy-3'-methoxy-7,4'-diacetoxy-flavanon
—— 3,7-Diacetoxyflavon 109688-06-4 C19H14O6
3,7-Diacetoxyflavon
—— 3-Methoxy-6-propionyl-2-p-tolyl-chromen-4-one 141070-47-5 C20H18O4
3-Methoxy-6-propionyl-2-p-tolyl-chromen-4-one
—— (2S,5''R)-5,7,4'-trihydroxy-8-(2-oxopyrrolidin-5-yl)flavanone 1023993-45-4 C19H17NO6
(2S,5''R)-5,7,4'-trihydroxy-8-(2-oxopyrrolidin-5-yl)flavanone
—— 3,8-Dibrom-4,5,7-trimethoxy-3-flaven 72397-33-2 C18H16Br2O4
3,8-Dibrom-4,5,7-trimethoxy-3-flaven
—— 3-Methyl-2-phenyl-6-((E)-3-p-tolyl-acryloyl)-chromen-4-one 144728-45-0 C26H20O3
3-Methyl-2-phenyl-6-((E)-3-p-tolyl-acryloyl)-chromen-4-one
—— 6-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-4'-aminoflavone 1147337-28-7 C21H23NO6
6-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-4'-aminoflavone
—— 3-ethoxy-2-(3-ethoxy-4-methoxy-phenyl)-5,7-dihydroxy-chromen-4-one 705932-27-0 C20H20O7
3-ethoxy-2-(3-ethoxy-4-methoxy-phenyl)-5,7-dihydroxy-chromen-4-one
—— 2-(2-ethoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 57009-18-4 C18H14O5
2-(2-ethoxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— epiafzelechin-(4β-8,2β-O-7)-ent-afzelechin tetramethyl ether 143901-40-0 C34H32O10
epiafzelechin-(4β-8,2β-O-7)-ent-afzelechin tetramethyl ether
—— 3-(4-butoxyphenyl)-3-(4-methoxyphenyl)-5-methoxy-7-fluoro-11-methoxy-13,13-dimethyl-3H,13H-indeno[2',1':3,4]naphtho[1,2-b]pyran 1380855-75-3 C41H39FO5
3-(4-butoxyphenyl)-3-(4-methoxyphenyl)-5-methoxy-7-fluoro-11-methoxy-13,13-dimethyl-3H,13H-indeno[2',1':3,4]naphtho[1,2-b]pyran
—— 4',6'-dihydroxy-2',3',5,6,7-pentamethoxyflavone 89328-94-9 C20H20O9
4',6'-dihydroxy-2',3',5,6,7-pentamethoxyflavone
—— Ethyl 2-[2'-(p-Chlorophenyl)-6'-chromonyl]-2-methylmalonate 60402-65-5 C23H21ClO6
Ethyl 2-[2'-(p-Chlorophenyl)-6'-chromonyl]-2-methylmalonate
—— (-)-robinetinidol-(4β,8)-(+)-catechin octa-O-methyl diacetate 78185-20-3 C42H46O14
(-)-robinetinidol-(4β,8)-(+)-catechin octa-O-methyl diacetate
—— 10-Methoxy-6,6-diphenylbenzo[c]chromen-1-amine 947409-66-7 C26H21NO2
10-Methoxy-6,6-diphenylbenzo[c]chromen-1-amine
—— 3-benzyl-2-phenyl-2H-chromene 1135951-75-5 C22H18O
3-benzyl-2-phenyl-2H-chromene
—— 8-Brom-5-hydroxy-3,7,3',4'-tetraacetoxy-flavon 3162-21-8 C23H17BrO11
8-Brom-5-hydroxy-3,7,3',4'-tetraacetoxy-flavon
—— 2-(4-chlorophenyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one 26207-73-8 C17H15ClO4
2-(4-chlorophenyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one
—— 5-Formyl-3,3',4',6,7-pentahydroxyflavon 67443-83-8 C16H10O8
5-Formyl-3,3',4',6,7-pentahydroxyflavon
—— 7-methoxy-5-methyl-2-(3,4-methylenedioxyphenyl)-4H-1-benzopyran-4-one 132886-92-1 C18H14O5
7-methoxy-5-methyl-2-(3,4-methylenedioxyphenyl)-4H-1-benzopyran-4-one