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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
—— 3',5-di-O-acetyl-3,4',7-tri-O-benzylquercetin 103389-61-3 C40H32O9
3',5-di-O-acetyl-3,4',7-tri-O-benzylquercetin
—— 4'-methyl-3'-nitroflavone 132318-85-5 C16H11NO4
4'-methyl-3'-nitroflavone
—— 2-(2-(p-tolyl)chroman-4-ylidene)hydrazine-1-carboxamide 534569-38-5 C17H17N3O2
2-(2-(p-tolyl)chroman-4-ylidene)hydrazine-1-carboxamide
—— 3-Brom-5-hydroxy-6-benzoyl-flavanon 61653-29-0 C22H15BrO4
3-Brom-5-hydroxy-6-benzoyl-flavanon
—— 5R-[3-(2-thiomorpholin-4-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-]naphthalene-2,8-diol 1157856-85-3 C29H29NO5S
5R-[3-(2-thiomorpholin-4-yl-ethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-]naphthalene-2,8-diol
—— {4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}acetic acid methyl ester 1056053-26-9 C38H50O7Si2
{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}acetic acid methyl ester
—— 7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-isobutylamino-4H-chromen-4-one 1094471-26-7 C34H33NO5
7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-isobutylamino-4H-chromen-4-one
—— 3-O-[(E)-4-(3-chloro-4-hydroxyphenyl)-2-oxobut-3-en-1-yl]kaempferol 1338577-32-4 C25H17ClO8
3-O-[(E)-4-(3-chloro-4-hydroxyphenyl)-2-oxobut-3-en-1-yl]kaempferol
—— 6-methyl-2-(4-(phenylthio)phenyl)-4H-chromen-4-one 1360145-37-4 C22H16O2S
6-methyl-2-(4-(phenylthio)phenyl)-4H-chromen-4-one
—— 7-[2-(1-morpholino-2-oxopropylidene)hydrazinyl]-2-phenyl-4H-chromen-4-one 1394154-33-6 C22H21N3O4
7-[2-(1-morpholino-2-oxopropylidene)hydrazinyl]-2-phenyl-4H-chromen-4-one
—— 7-Acetoxy-3-ethyl-flavanon 94303-03-4 C19H18O4
7-Acetoxy-3-ethyl-flavanon
—— Acetic acid 6-(3-acetoxy-4,5-dimethoxy-phenyl)-4,7-dimethoxy-8-oxo-8H-[1,3]dioxolo[4,5-g]chromen-9-yl ester 82668-98-2 C24H22O12
Acetic acid 6-(3-acetoxy-4,5-dimethoxy-phenyl)-4,7-dimethoxy-8-oxo-8H-[1,3]dioxolo[4,5-g]chromen-9-yl ester
—— 4'-chloro-7-(2-hydroxy-3-isopropylaminopropoxy) flavone hydrochloride 84858-27-5 C21H22ClNO4*ClH
4'-chloro-7-(2-hydroxy-3-isopropylaminopropoxy) flavone hydrochloride
—— 4'-Benzyloxy-3,5,7,8,2'-pentamethoxyflavone 110561-89-2 C27H26O8
4'-Benzyloxy-3,5,7,8,2'-pentamethoxyflavone
—— (E)-2-phenyl-4-styryl-2,3-dihydrofuro[3,2-c]pyridine 1401693-70-6 C21H17NO
(E)-2-phenyl-4-styryl-2,3-dihydrofuro[3,2-c]pyridine
—— 5,7,4'-triacetoxy-6-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-8-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)flavone 1253228-04-4 C43H44O22
5,7,4'-triacetoxy-6-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-8-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)flavone
—— butyl 2-(4-chloro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate 1609940-33-1 C22H19ClO5
butyl 2-(4-chloro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate
—— methyl 2-(5-((2R,3R,4S)-3,5,7-trihydroxy-4-(2-hydroxy-4,6-dimethoxyphenyl)chroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate 1258979-24-6 C27H26O11
methyl 2-(5-((2R,3R,4S)-3,5,7-trihydroxy-4-(2-hydroxy-4,6-dimethoxyphenyl)chroman-2-yl)benzo[d][1,3]dioxol-2-yl)acetate
—— 7-<N-Ethyl-N-(2-hydroxy-ethyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen 105792-69-6 C21H21NO5
7-<N-Ethyl-N-(2-hydroxy-ethyl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen
—— 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 1610737-88-6 C22H16O8S
2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate
—— 8-fluoro-2-phenyl-2H-chromene 1532560-34-1 C15H11FO
8-fluoro-2-phenyl-2H-chromene
—— 7-benzyloxy-5,8-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 1570-11-2 C24H20O7
7-benzyloxy-5,8-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one
—— 7-fluoro-3-iodo-2-phenyl-chromen-4-one 1279088-36-6 C15H8FIO2
7-fluoro-3-iodo-2-phenyl-chromen-4-one
—— (+-)-5,7-dihydroxy-3c(?)-methyl-2r-phenyl-chroman-4-one 108837-19-0 C16H14O4
(+-)-5,7-dihydroxy-3c(?)-methyl-2r-phenyl-chroman-4-one
—— Di-O-acetyl-citrifoliol 6821-23-4 C20H18O7
Di-O-acetyl-citrifoliol
—— 5,6-Diacetoxy-<6-phenyl-α-pyrono-3,4>3,2-benzofuran 4827-26-3 C21H14O7
5,6-Diacetoxy-<6-phenyl-α-pyrono-3,4>3,2-benzofuran
—— 2-(2,3,4-trimethoxy-phenyl)-2<i>H</i>-chromene 69630-83-7 C18H18O4
2-(2,3,4-trimethoxy-phenyl)-2<i>H</i>-chromene
—— 7-Chlor-6-nitro-flavon 92429-18-0 C15H8ClNO4
7-Chlor-6-nitro-flavon
—— Acetic acid 2-(4-acetoxy-2-methoxy-phenyl)-3,7,8-trimethoxy-4-oxo-4H-chromen-5-yl ester 110575-87-6 C23H22O10
Acetic acid 2-(4-acetoxy-2-methoxy-phenyl)-3,7,8-trimethoxy-4-oxo-4H-chromen-5-yl ester
—— 5,7,3'-trihydroxy-6-O-b-D-glucopyranosylflavone 1323905-15-2 C21H20O11
5,7,3'-trihydroxy-6-O-b-D-glucopyranosylflavone
—— 3-(4-methoxy-phenyl)-benzo[<i>f</i>]chromenylium; chloride 99729-14-3 C20H15O2*Cl
3-(4-methoxy-phenyl)-benzo[<i>f</i>]chromenylium; chloride
—— 6-Nitro-8-methyl-4'-methoxy-flavon 93325-65-6 C17H13NO5
6-Nitro-8-methyl-4'-methoxy-flavon
—— 3,5,7,4',2'',3'',4'',6''-octa-O-acetyl-(+)-catechin 3'-O-β-D-glucoside 1209469-12-4 C37H40O19
3,5,7,4',2'',3'',4'',6''-octa-O-acetyl-(+)-catechin 3'-O-β-D-glucoside
—— 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan 749256-77-7 C54H46O15
5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan
—— 3,5,7,4'-Quercetin-tetramethylether-3'-glucosid 102031-21-0 C25H28O12
3,5,7,4'-Quercetin-tetramethylether-3'-glucosid
—— 3-chloro-7-iodo-1-methyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one 1279089-85-8 C17H10ClIN2O2
3-chloro-7-iodo-1-methyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one
—— 2'-benzyloxy-3',5,5',6,7-pentamethoxyflavone 93092-11-6 C27H26O8
2'-benzyloxy-3',5,5',6,7-pentamethoxyflavone
—— 7-iodo-1-isopropyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one 1279089-46-1 C19H15IN2O2
7-iodo-1-isopropyl-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one
—— 7-(acetoxymethyl)-5-amino-2-[4-(chloroacetamido)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one 468719-68-8 C20H14ClF3N2O5
7-(acetoxymethyl)-5-amino-2-[4-(chloroacetamido)-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one
—— 5-acetoxy-2-(4-acetoxy-phenyl)-6-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyl)-7-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 73089-42-6 C47H50O25
5-acetoxy-2-(4-acetoxy-phenyl)-6-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyl)-7-(tetra-<i>O</i>-acetyl-β-D-glucopyranosyloxy)-chromen-4-one
—— 5,7-dimethoxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(3-methoxyphenyl)-4H-chromen-4-one 1128053-42-8 C24H25NO5
5,7-dimethoxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(3-methoxyphenyl)-4H-chromen-4-one
—— 1-[3-Methyl-7-(3-Methylbut-2-Enyloxy)Flavon-8-yl]-3-(2-Thienyl)-Propen-1-one 329913-52-2 C28H24O4S
1-[3-Methyl-7-(3-Methylbut-2-Enyloxy)Flavon-8-yl]-3-(2-Thienyl)-Propen-1-one
—— 4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-5,7-dihydroxyflavan 1253227-76-7 C28H30O12
4'-acetoxy-6-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-5,7-dihydroxyflavan
—— 3-ethyl-2-(((7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromen-6-yl)methylene)hydrazono)-1,3-thiazolidin-4-one 1260141-59-0 C22H19N3O5S
3-ethyl-2-(((7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromen-6-yl)methylene)hydrazono)-1,3-thiazolidin-4-one
—— (2R,3R)-(5,7-bis(2-nitrophenylsulfonyloxy)-2-(3,4,5-tris(2-nitrophenylsulfonyloxy)phenyl)chroman-3-yl) 4-methoxy-3,5-bis(2-nitrophenylsulfonyloxy)benzoate 1186527-13-8 C65H41N7O39S7
(2R,3R)-(5,7-bis(2-nitrophenylsulfonyloxy)-2-(3,4,5-tris(2-nitrophenylsulfonyloxy)phenyl)chroman-3-yl) 4-methoxy-3,5-bis(2-nitrophenylsulfonyloxy)benzoate
—— 8-Bromo-6-chloro-2-(2-methoxy-phenyl)-chromen-4-one 134640-64-5 C16H10BrClO3
8-Bromo-6-chloro-2-(2-methoxy-phenyl)-chromen-4-one
—— tanariflavanone B 352276-81-4 C30H34O6
tanariflavanone B
—— 4,4',6'-Trihydroxy-2'-O-β-D-galactopyranosyl-chalkon 72843-28-8 C21H22O10
4,4',6'-Trihydroxy-2'-O-β-D-galactopyranosyl-chalkon
—— hexahydromacaflavanone C 1178898-27-5 C30H40O6
hexahydromacaflavanone C
—— (2R)-6-bromo-2-(4-nitrophenyl)-2H-chromene-3-carbaldehyde 1608094-82-1 C16H10BrNO4
(2R)-6-bromo-2-(4-nitrophenyl)-2H-chromene-3-carbaldehyde