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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
—— rac-2,2'-((1E,1'E)-(((2R,4S)-2,3,3-trimethylchromane-2,4-diyl)bis(azaneylylidene))bis(methaneylylidene))diphenol 99875-19-1 C26H26N2O3
rac-2,2'-((1E,1'E)-(((2R,4S)-2,3,3-trimethylchromane-2,4-diyl)bis(azaneylylidene))bis(methaneylylidene))diphenol
—— 7,2',4'-Trimethoxy-3-prenylflavon 65612-83-1 C23H24O5
7,2',4'-Trimethoxy-3-prenylflavon
—— 4-oxo-2-phenyl-4H-chromene-3,6-diyl bis(3-bromobenzoate) 1244966-66-2 C29H16Br2O6
4-oxo-2-phenyl-4H-chromene-3,6-diyl bis(3-bromobenzoate)
—— 2-(3-chloro-phenyl)-3-(furan-2-carbonyl)-chromen-4-one 65485-37-2 C20H11ClO4
2-(3-chloro-phenyl)-3-(furan-2-carbonyl)-chromen-4-one
—— (2R,3R)-8-Methoxy-2-phenyl-chroman-3-ylamine 112514-03-1 C16H17NO2
(2R,3R)-8-Methoxy-2-phenyl-chroman-3-ylamine
—— kaempferol 4′-O-(β-D-glucopyranosyl-(1→2)(α-L-rhamnopyranosyl-(1→6))-β-D-glucopyranoside) 1426341-67-4 C33H40O20
kaempferol 4′-O-(β-D-glucopyranosyl-(1→2)(α-L-rhamnopyranosyl-(1→6))-β-D-glucopyranoside)
—— 5,7-dimethoxymethoxy-3',4',5'-trimethoxy-8-(3,3-dimethylallyl)-flavanone 1075171-43-5 C27H34O9
5,7-dimethoxymethoxy-3',4',5'-trimethoxy-8-(3,3-dimethylallyl)-flavanone
—— (2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate 851775-46-7 C75H68O12
(2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate
—— [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate 908855-83-4 C57H56O15
[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate
—— 2-(2-benzyloxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid 66848-78-0 C23H16O5
2-(2-benzyloxy-phenyl)-4-oxo-4<i>H</i>-chromene-6-carboxylic acid
—— 3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran 761409-08-9 C40H37NO4
3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran
—— 4-[4-[10-Methoxy-5-(4-methoxyphenyl)-11-(trifluoromethylsulfanyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,1'-cyclooctane]-5-yl]phenyl]morpholine 1263317-89-0 C46H44F3NO4S
4-[4-[10-Methoxy-5-(4-methoxyphenyl)-11-(trifluoromethylsulfanyl)spiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,1'-cyclooctane]-5-yl]phenyl]morpholine
—— (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-tetrahydro-pyran-2-carboxylic acid 67322-22-9 C32H32O17
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-tetrahydro-pyran-2-carboxylic acid
—— (+/-)2,5-dihydro-9-hydroxy-10-methoxy-2,2,4-trimethyl-5-(2-methylphenyl)-1H-[1]benzopyrano[3,4-f]quinoline 239069-39-7 C27H27NO3
(+/-)2,5-dihydro-9-hydroxy-10-methoxy-2,2,4-trimethyl-5-(2-methylphenyl)-1H-[1]benzopyrano[3,4-f]quinoline
—— 14,14-bis(4-methoxyphenyl)-N,N,1',1',5',5'-hexamethylspiro[15,20,23-trioxahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane]-21-amine 1268817-10-2 C47H49NO5
14,14-bis(4-methoxyphenyl)-N,N,1',1',5',5'-hexamethylspiro[15,20,23-trioxahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane]-21-amine
—— 3-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4,8,12-trimethyltridecyl)chromen-4-one 649552-04-5 C33H46O6
3-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4,8,12-trimethyltridecyl)chromen-4-one
—— 7-Benzyloxy-2-(4-benzyloxy-phenyl)-5-hydroxy-3,6,8-trimethoxy-chromen-4-one 176662-34-3 C32H28O8
7-Benzyloxy-2-(4-benzyloxy-phenyl)-5-hydroxy-3,6,8-trimethoxy-chromen-4-one
—— 8-bromo-6-chloro-4-oxo-2-phenyl-4H-chromene-3-carbonitrile 1224712-20-2 C16H7BrClNO2
8-bromo-6-chloro-4-oxo-2-phenyl-4H-chromene-3-carbonitrile
—— 6-Allyl-5,7-dihydroxy-2-(2-allyl-3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one 178367-37-8 C22H20O6
6-Allyl-5,7-dihydroxy-2-(2-allyl-3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
—— (+/-)-<i>trans</i>-3-bromo-2-(4-methoxy-phenyl)-chroman-4-one 14221-66-0 C16H13BrO3
(+/-)-<i>trans</i>-3-bromo-2-(4-methoxy-phenyl)-chroman-4-one
—— (2S,3R,4R)-2-(4-benzoxyphenyl)-7-benzoxy-4-(2,4,6-trimethoxy-3-(dodecanoyl)phenyl)chroman-3-ol 888026-47-9 C50H58O8
(2S,3R,4R)-2-(4-benzoxyphenyl)-7-benzoxy-4-(2,4,6-trimethoxy-3-(dodecanoyl)phenyl)chroman-3-ol
—— 4-[14,14-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,20,22-trioxahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,3'-cyclohexane]-21-yl]morpholine 1268817-01-1 C48H49NO6
4-[14,14-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,20,22-trioxahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,3'-cyclohexane]-21-yl]morpholine
—— Toluene-4-sulfonic acid 5,7-dimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 170234-94-3 C27H26O10S
Toluene-4-sulfonic acid 5,7-dimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester
—— 7,8,3',4',5'-Pentamethoxy-3-methylflavon 65894-06-6 C21H22O7
7,8,3',4',5'-Pentamethoxy-3-methylflavon
—— 7,8,3',4'-Tetramethoxy-3-methylflavon 65894-07-7 C20H20O6
7,8,3',4'-Tetramethoxy-3-methylflavon
—— 7-Acetoxy-5-methoxy-6,8-dimethylflavanon 51621-54-6 C20H20O5
7-Acetoxy-5-methoxy-6,8-dimethylflavanon
—— Acetic acid 8-(5,8-diacetoxy-2,2-dimethyl-chroman-6-yl)-2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-g]chromen-5-yl ester 64379-42-6 C31H30O10
Acetic acid 8-(5,8-diacetoxy-2,2-dimethyl-chroman-6-yl)-2,2-dimethyl-6-oxo-2H,6H-pyrano[3,2-g]chromen-5-yl ester
—— theaflavin digallate trimer 1 1256244-34-4 C64H46O29
theaflavin digallate trimer 1
—— 3-acetoxy-2-phenyl-benzo[h]chromen-4-one 22825-62-3 C21H14O4
3-acetoxy-2-phenyl-benzo[h]chromen-4-one
—— 1198053-59-6 C21H19ClO4
—— 1205679-04-4 C40H30O6
—— (2S,3S)-cis-3',4'-dimethoxy-7-(phenylmethoxy)flavan-3-ol 1196870-49-1 C24H24O5
(2S,3S)-cis-3',4'-dimethoxy-7-(phenylmethoxy)flavan-3-ol
—— 5-[4-(Dimethylamino)phenyl]-10,11,17,18-tetramethoxy-21,21-dimethyl-5,22-diphenyl-6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8,10,12,15,17,19-nonaen-22-ol 945425-02-5 C47H45NO6
5-[4-(Dimethylamino)phenyl]-10,11,17,18-tetramethoxy-21,21-dimethyl-5,22-diphenyl-6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8,10,12,15,17,19-nonaen-22-ol
—— [2-(4-hydroxy-phenyl)-4-oxo-chroman-6-yl]-acetic acid 101451-90-5 C17H14O5
[2-(4-hydroxy-phenyl)-4-oxo-chroman-6-yl]-acetic acid
—— 2-(4-Hydroxyphenyl)-3,7-dimethylchromen-4-one 132020-61-2 C17H14O3
2-(4-Hydroxyphenyl)-3,7-dimethylchromen-4-one
—— (3aS,9bR)-1-Methyl-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-b]pyrrole-2-carboxylic acid ethyl ester 92345-88-5 C15H19NO3
(3aS,9bR)-1-Methyl-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-b]pyrrole-2-carboxylic acid ethyl ester
—— 2-[2-(4-Chloro-phenyl)-3-methoxy-4-oxo-4H-chromen-6-yl]-propionic acid 141070-64-6 C19H15ClO5
2-[2-(4-Chloro-phenyl)-3-methoxy-4-oxo-4H-chromen-6-yl]-propionic acid
—— 6-n-butyryl-2-phenyl-3-methoxychromone 173469-79-9 C20H18O4
6-n-butyryl-2-phenyl-3-methoxychromone
—— 2-(2,5-dihydroxy-3,4-dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one 743423-87-2 C20H20O9
2-(2,5-dihydroxy-3,4-dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one
—— 7-ethoxy-5,8-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 1071024-49-1 C19H18O7
7-ethoxy-5,8-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one
—— butyl 2-(9-chloro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate 1609940-31-9 C22H19ClO5
butyl 2-(9-chloro-7-oxo-6,7-dihydrochromeno[4,3-b]chromen-6-yl)acetate
—— 3-methoxy-2-(2-methoxy-phenyl)-6-methyl-chromen-4-one 109253-96-5 C18H16O4
3-methoxy-2-(2-methoxy-phenyl)-6-methyl-chromen-4-one
—— 7-hydroxy-6-[(E)-2-(2-hydroxyphenyl)diazen-1-yl]-2-(4-methoxyphenyl)-4H-chromen-4-one 1565622-91-4 C22H16N2O5
7-hydroxy-6-[(E)-2-(2-hydroxyphenyl)diazen-1-yl]-2-(4-methoxyphenyl)-4H-chromen-4-one
—— Vicenin-2-perdeuteriomethylether 71973-11-0 C38H52O15
Vicenin-2-perdeuteriomethylether
—— 4-[2-(4-Methoxy-phenyl)-chromen-(4E)-ylideneamino]-benzoic acid 126480-39-5 C23H17NO4
4-[2-(4-Methoxy-phenyl)-chromen-(4E)-ylideneamino]-benzoic acid
—— 3,3-dichloro-2-(4-methoxyphenyl)-4-chromanone 71993-29-8 C16H12Cl2O3
3,3-dichloro-2-(4-methoxyphenyl)-4-chromanone
—— 2-(1,3-diphenyl-1<i>H</i>-pyrazol-4-yl)-3-methoxy-6-methyl-chromen-4-one 56642-67-2 C26H20N2O3
2-(1,3-diphenyl-1<i>H</i>-pyrazol-4-yl)-3-methoxy-6-methyl-chromen-4-one
—— 5-Methoxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one 178367-28-7 C23H26O8
5-Methoxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one
—— 3-acetoxy-8-bromo-6-chloro-2-(4-nitrophenyl)chromone 1192742-64-5 C17H9BrClNO6
3-acetoxy-8-bromo-6-chloro-2-(4-nitrophenyl)chromone
—— (S)-methyl 2-(3-acetyl-1,4,5,6-tetrahydro-6-oxo-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-1,2,4-triazin-5-yl)acetate 1402841-94-4 C23H19N3O6
(S)-methyl 2-(3-acetyl-1,4,5,6-tetrahydro-6-oxo-1-(4-oxo-2-phenyl-4H-chromen-7-yl)-1,2,4-triazin-5-yl)acetate