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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
—— (2S,3R)-5,7-bis(benzyloxy)-2-phenylchroman-3-ol 1350895-95-2 C29H26O4
(2S,3R)-5,7-bis(benzyloxy)-2-phenylchroman-3-ol
—— 3,5-Dihydroxy-7-methoxy-6-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 154048-29-0 C21H22O10
3,5-Dihydroxy-7-methoxy-6-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
—— 2-(3-hydroxy-4-methoxy-phenyl)-benzo[<i>h</i>]chromen-4-one 125574-16-5 C20H14O4
2-(3-hydroxy-4-methoxy-phenyl)-benzo[<i>h</i>]chromen-4-one
—— 4',7-Dibenzyloxy-3,5,6,8-tetramethoxy-flavon 57393-75-6 C33H30O8
4',7-Dibenzyloxy-3,5,6,8-tetramethoxy-flavon
—— (2R,3S)-2-(4-chlorophenyl)-3-phenylsulfanyl-2,3-dihydrochromen-4-one 113093-92-8 C21H15ClO2S
(2R,3S)-2-(4-chlorophenyl)-3-phenylsulfanyl-2,3-dihydrochromen-4-one
—— 2-(4-Ethoxy-3-hydroxy-phenyl)-5-hydroxy-chroman-4-one 64687-94-1 C17H16O5
2-(4-Ethoxy-3-hydroxy-phenyl)-5-hydroxy-chroman-4-one
—— 2',4'-diisopropyloxy-3,5,5',6,7-pentamethoxyflavone 111786-53-9 C26H32O9
2',4'-diisopropyloxy-3,5,5',6,7-pentamethoxyflavone
—— rac-2-(4-methoxyphenyl)-2H-chromene-3-carboxylic acid 1204754-60-8 C17H14O4
rac-2-(4-methoxyphenyl)-2H-chromene-3-carboxylic acid
—— N-[4-(4-oxo-3,4-dihydro-2H-chromen-2-yl)phenyl]acetamide 108973-48-4 C17H15NO3
N-[4-(4-oxo-3,4-dihydro-2H-chromen-2-yl)phenyl]acetamide
—— 3'-benzyloxy-4',5,6,7,8-pentamethoxyflavone 29201-99-8 C27H26O8
3'-benzyloxy-4',5,6,7,8-pentamethoxyflavone
—— (2R)-3t,4c,7-Triacetoxy-2r-(3,4,5-triacetoxy-phenyl)-chroman 122446-43-9 C27H26O13
(2R)-3t,4c,7-Triacetoxy-2r-(3,4,5-triacetoxy-phenyl)-chroman
—— Salz 97076-35-2 C9H10N4O4*C21H23NO3
Salz
—— 5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-8-phenyl-2H,6H-pyrano[3,2-g]chromen-6-one 50679-02-2 C25H24O4
5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-8-phenyl-2H,6H-pyrano[3,2-g]chromen-6-one
—— 2-(4-benzyloxy-2,3-dimethoxy-phenyl)-chroman-4-ol 69471-17-6 C24H24O5
2-(4-benzyloxy-2,3-dimethoxy-phenyl)-chroman-4-ol
—— 3-[(3R,4S,5S,6R)-6-((3aR,4R,6S,7S,7aR)-2,2-Diethyl-7-hydroxy-6-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxymethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one 70189-38-7 C32H38O16
3-[(3R,4S,5S,6R)-6-((3aR,4R,6S,7S,7aR)-2,2-Diethyl-7-hydroxy-6-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxymethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one
—— 7-acetoxy-2-(4-acetoxy-3,5-dimethoxy-phenyl)-5-hydroxy-chromen-4-one 36209-86-6 C21H18O9
7-acetoxy-2-(4-acetoxy-3,5-dimethoxy-phenyl)-5-hydroxy-chromen-4-one
—— Limocitrin-3-β-D-glucosid-heptaacetat 106198-08-7 C37H38O20
Limocitrin-3-β-D-glucosid-heptaacetat
—— 2-benzo[1,3]dioxol-5-yl-5,6-dihydroxy-3,7-dimethoxy-chromen-4-one 93656-01-0 C18H14O8
2-benzo[1,3]dioxol-5-yl-5,6-dihydroxy-3,7-dimethoxy-chromen-4-one
—— 1134938-79-6 C21H16N2O3
—— Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-5-yl ester 154048-12-1 C25H22O10S
Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-5-yl ester
—— Acetic acid 2-(3,4-dimethoxy-phenyl)-3,7-dimethoxy-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester 154047-96-8 C28H26O11S
Acetic acid 2-(3,4-dimethoxy-phenyl)-3,7-dimethoxy-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester
—— rac-2-(3,4-dichlorophenyl)-6-fluoro-2H-chromene-3-carboxylic acid 1204755-20-3 C16H9Cl2FO3
rac-2-(3,4-dichlorophenyl)-6-fluoro-2H-chromene-3-carboxylic acid
—— 2-(1,3-benzodioxol-5-yl)-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepine 1449790-33-3 C18H18O4
2-(1,3-benzodioxol-5-yl)-7-methoxy-2,3,4,5-tetrahydro-1-benzoxepine
—— 6-hydroxy-2-phenyl-chromenylium; chloride 15402-13-8 C15H11O2*Cl
6-hydroxy-2-phenyl-chromenylium; chloride
—— Acetic acid (2S,3S,4S,2'S,3'S)-3,5,7,3',5'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-7'-yl ester 88079-90-7 C50H46O22
Acetic acid (2S,3S,4S,2'S,3'S)-3,5,7,3',5'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-7'-yl ester
—— 8-Methoxy-17-(trifluoromethyl)spiro[6-oxapentacyclo[11.7.0.02,10.03,7.015,20]icosa-1(13),2,7,9,11,15(20),16,18-octaene-14,1'-cyclooctane]-11-ol 1259400-41-3 C28H27F3O3
8-Methoxy-17-(trifluoromethyl)spiro[6-oxapentacyclo[11.7.0.02,10.03,7.015,20]icosa-1(13),2,7,9,11,15(20),16,18-octaene-14,1'-cyclooctane]-11-ol
—— 5,4'-Diacetylmorusin-acetylperoxid 67721-75-9 C31H30O11
5,4'-Diacetylmorusin-acetylperoxid
—— 5,7-hydroxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-methoxyphenyl)-4H-chromen-4-one 1254302-07-2 C22H21NO5
5,7-hydroxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-methoxyphenyl)-4H-chromen-4-one
—— 3-benzyl-2-phenylchromane 1135951-73-3 C22H20O
3-benzyl-2-phenylchromane
—— 10-(3,4-Dimethoxy-phenyl)-3,3-dioxo-2,3-dihydro-10H-4,9-dioxa-3λ<sup>6</sup>-thia-2-aza-phenanthren-1-one 116215-66-8 C18H15NO7S
10-(3,4-Dimethoxy-phenyl)-3,3-dioxo-2,3-dihydro-10H-4,9-dioxa-3λ<sup>6</sup>-thia-2-aza-phenanthren-1-one
—— 2-(3-benzyloxy-phenyl)-5-methoxy-chromen-4-one 742079-14-7 C23H18O4
2-(3-benzyloxy-phenyl)-5-methoxy-chromen-4-one
—— (2-methylphenyl)-2H-chromene 1327267-93-5 C16H14O
(2-methylphenyl)-2H-chromene
—— (2S,5''S)-5,7,4'-trihydroxy-6-(2-oxopyrrolidin-5-yl)flavanone 1029363-29-8 C19H17NO6
(2S,5''S)-5,7,4'-trihydroxy-6-(2-oxopyrrolidin-5-yl)flavanone
—— rac-2-(3-bromo-4-chlorophenyl)-2H-chromene-3-carboxylic acid 1204755-09-8 C16H10BrClO3
rac-2-(3-bromo-4-chlorophenyl)-2H-chromene-3-carboxylic acid
—— 7-Difluoromethoxy-2-(4-difluoromethoxy-phenyl)-5-hydroxy-6-iodo-chromen-4-one 801218-75-7 C17H9F4IO5
7-Difluoromethoxy-2-(4-difluoromethoxy-phenyl)-5-hydroxy-6-iodo-chromen-4-one
—— Acetic acid 2-(3,4-dimethoxy-phenyl)-3-hydroxy-7-methoxy-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester 154048-04-1 C27H24O11S
Acetic acid 2-(3,4-dimethoxy-phenyl)-3-hydroxy-7-methoxy-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester
—— 2-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)-6,7-bis((tert-butyldimethylsilyl)oxy)-3-hydroxy-4H-chromen-4-one 1068580-99-3 C39H66O7Si4
2-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)-6,7-bis((tert-butyldimethylsilyl)oxy)-3-hydroxy-4H-chromen-4-one
—— (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one 126655-08-1 C22H16O10
(2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano<3,4-c>-2-benzopyran-1-one
—— 1428646-29-0 C23H20O6
—— 6-(o-acetoxybenzyl)-3,3',4',5,7-penta-O-acetyl-(+)-catechin 81410-27-7 C34H32O13
6-(o-acetoxybenzyl)-3,3',4',5,7-penta-O-acetyl-(+)-catechin
—— methyl 3-methylflavon-6-ylethanoate 126538-15-6 C19H16O4
methyl 3-methylflavon-6-ylethanoate
—— 7-β-D-glucopyranosyloxy-3,5-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 121965-13-7 C24H26O11
7-β-D-glucopyranosyloxy-3,5-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one
—— 3,5,4'-trihydroxy-6,7-methylenedioxy-3-O-β-D-glucopyranoside 121068-97-1 C22H20O12
3,5,4'-trihydroxy-6,7-methylenedioxy-3-O-β-D-glucopyranoside
—— 1,1-dichloro-7,7a-dimethyl-1a-phenyl-7H-cyclopropa[b]chromene 111861-72-4 C18H16Cl2O
1,1-dichloro-7,7a-dimethyl-1a-phenyl-7H-cyclopropa[b]chromene
—— fulicinerine 1025893-48-4 C32H42O6
fulicinerine
—— 6-Bromo-7-hydroxy-2-(4-hydroxy-phenyl)-chromen-4-one 78050-75-6 C15H9BrO4
6-Bromo-7-hydroxy-2-(4-hydroxy-phenyl)-chromen-4-one
—— 2H-1-Benzopyran,7-methoxy-2,2-bis(4-methoxyphenyl)-8-[1-(4-methoxyphenyl)ethenyl]-4-methyl- 141215-54-5 C34H32O5
2H-1-Benzopyran,7-methoxy-2,2-bis(4-methoxyphenyl)-8-[1-(4-methoxyphenyl)ethenyl]-4-methyl-
—— Toluene-4-sulfonic acid 2-(3,4-bis-benzyloxy-phenyl)-3,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-5-yl ester 154048-17-6 C37H30O10S
Toluene-4-sulfonic acid 2-(3,4-bis-benzyloxy-phenyl)-3,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-5-yl ester
—— 690274-19-2 C33H37NO6
—— (+/-)-Monoacetyl-O-trimethyl-fustin 13798-88-4 C20H20O7
(+/-)-Monoacetyl-O-trimethyl-fustin