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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
—— 7-methyl-2-(naphthalen-2-yl)-6-[(E)-3-(naphthalen-2-yl)acryloyl]-5-phenylchroman-4-one 1365935-08-5 C39H28O3
7-methyl-2-(naphthalen-2-yl)-6-[(E)-3-(naphthalen-2-yl)acryloyl]-5-phenylchroman-4-one
—— (2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 908855-87-8 C45H78O11Si4
(2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
—— 3'-Chlor-3-hydroxy-2',5,7,8-tetramethoxy-flavon 65095-85-4 C19H17ClO7
3'-Chlor-3-hydroxy-2',5,7,8-tetramethoxy-flavon
—— (2R,3S,4S,8S,9S)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol 105805-43-4 C30H26O11
(2R,3S,4S,8S,9S)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromene-3,5,9-triol
—— 2,4,9,11-Tetrahydroxy-6-(4-hydroxy-3-methoxy-phenyl)-5-methyl-7,13-dioxa-benzo[3,4]cyclohepta[1,2-b]naphthalen-8-one 61276-41-3 C25H18O9
2,4,9,11-Tetrahydroxy-6-(4-hydroxy-3-methoxy-phenyl)-5-methyl-7,13-dioxa-benzo[3,4]cyclohepta[1,2-b]naphthalen-8-one
—— 5-hydroxy-2-(4-methoxy-phenyl)-8,8-dimethyl-10-(3-methyl-but-2-enyl)-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 70872-36-5 C26H26O5
5-hydroxy-2-(4-methoxy-phenyl)-8,8-dimethyl-10-(3-methyl-but-2-enyl)-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— 5-Methyl-7-phenacylflavon 56150-41-5 C24H18O3
5-Methyl-7-phenacylflavon
—— 2-Phenyl-6-[6-(4-pyridin-2-ylpiperazin-1-yl)hexoxy]chromen-4-one 140438-98-8 C30H33N3O3
2-Phenyl-6-[6-(4-pyridin-2-ylpiperazin-1-yl)hexoxy]chromen-4-one
—— 1-((3,4-dihydro-7-hydroxy-2-(3,4-dihydroxyphenyl)-4-oxo-2Hchromen-8-yl)methyl) azepan-2-one 1400992-13-3 C22H23NO6
1-((3,4-dihydro-7-hydroxy-2-(3,4-dihydroxyphenyl)-4-oxo-2Hchromen-8-yl)methyl) azepan-2-one
—— Acetic acid 2-(4-methoxy-phenyl)-4-oxo-6-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-7-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester 61252-89-9 C46H50O24
Acetic acid 2-(4-methoxy-phenyl)-4-oxo-6-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-7-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester
—— (1-difluoromethoxy-6-(3,4-dimethoxy)phenyl-6H-dibenzo(b,d)pyran-8-yl)aniline 373632-54-3 C28H23F2NO4
(1-difluoromethoxy-6-(3,4-dimethoxy)phenyl-6H-dibenzo(b,d)pyran-8-yl)aniline
—— tetradecaffeylzebrinin 110065-27-5 C38H49O25*Cl
tetradecaffeylzebrinin
—— 7-methyl-4'-hydroxyflavone 1000977-24-1 C16H12O3
7-methyl-4'-hydroxyflavone
—— 5-methyl-2-phenyl-2<i>H</i>-chromen-7-ol 33018-52-9 C16H14O2
5-methyl-2-phenyl-2<i>H</i>-chromen-7-ol
—— (3aS,4R,9bR)-2-ethynyl-4-(4-hydroxy-phenyl)-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol 787622-44-0 C20H18O3
(3aS,4R,9bR)-2-ethynyl-4-(4-hydroxy-phenyl)-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol
—— 2-[2-[(4-methoxyphenyl)methoxymethyl]phenyl]-3,4-dihydro-2H-chromene 1327267-95-7 C24H24O3
2-[2-[(4-methoxyphenyl)methoxymethyl]phenyl]-3,4-dihydro-2H-chromene
—— 3,3-bis(4-methoxyphenyl)-10,12-dichloro-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran 1311275-01-0 C36H28Cl2O3
3,3-bis(4-methoxyphenyl)-10,12-dichloro-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran
—— 5,7-Dihydroxy-4'-benzyloxy-3,6,8-trimethoxy-flavon 57393-76-7 C25H22O8
5,7-Dihydroxy-4'-benzyloxy-3,6,8-trimethoxy-flavon
—— 6-Nitro-3',4'-dimethoxy-flavonol 109156-96-9 C17H13NO7
6-Nitro-3',4'-dimethoxy-flavonol
—— 4-[14,14-Bis(4-methoxyphenyl)-6-(trifluoromethyl)spiro[15,20,22-trioxahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3(8),4,6,11(16),12,17,19(23)-nonaene-9,1'-cyclooctane]-21-yl]morpholine 1268816-99-4 C47H44F3NO6
4-[14,14-Bis(4-methoxyphenyl)-6-(trifluoromethyl)spiro[15,20,22-trioxahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3(8),4,6,11(16),12,17,19(23)-nonaene-9,1'-cyclooctane]-21-yl]morpholine
—— 3-Hydroxy-2,3-dimethoxy-2-(4-methoxyphenyl)-6-propanoylchromen-4-one 131136-67-9 C21H22O7
3-Hydroxy-2,3-dimethoxy-2-(4-methoxyphenyl)-6-propanoylchromen-4-one
—— Acetic acid 5-((S)-5,7-dimethoxy-4-oxo-chroman-2-yl)-2,3-dimethoxy-phenyl ester 78335-39-4 C21H22O8
Acetic acid 5-((S)-5,7-dimethoxy-4-oxo-chroman-2-yl)-2,3-dimethoxy-phenyl ester
—— 7-Methoxy-2-o-anisyl-3-nitro-Δ<sup>3</sup>-chromen 57543-97-2 C17H15NO5
7-Methoxy-2-o-anisyl-3-nitro-Δ<sup>3</sup>-chromen
—— [(2R)-3-(1,3-benzodioxol-5-ylmethyl)-2-phenyl-2H-chromen-4-yl] 2,2-dimethylpropanoate 1318698-15-5 C28H26O5
[(2R)-3-(1,3-benzodioxol-5-ylmethyl)-2-phenyl-2H-chromen-4-yl] 2,2-dimethylpropanoate
—— (R)-6-acetyl-2-(4-ethylphenyl)-5,7-dimethylchroman-4-one 1438760-66-7 C21H22O3
(R)-6-acetyl-2-(4-ethylphenyl)-5,7-dimethylchroman-4-one
—— 1203579-98-9 C25H32O4S
—— 1198053-57-4 C29H19ClO4
—— 1198053-61-0 C29H19ClO4
—— 6-ethyl-2'-chloro-4'-nitroflavone 1388722-79-9 C17H12ClNO4
6-ethyl-2'-chloro-4'-nitroflavone
—— 65052-97-3 C50H46O22
—— Acetic acid 7-acetoxy-2-(4-acetoxy-phenyl)-6,8-bis-(3-methyl-but-2-enyl)-4-oxo-4H-chromen-5-yl ester 70872-33-2 C31H32O8
Acetic acid 7-acetoxy-2-(4-acetoxy-phenyl)-6,8-bis-(3-methyl-but-2-enyl)-4-oxo-4H-chromen-5-yl ester
—— 2'-Methoxy-5'-chlorflavon 57006-75-4 C16H11ClO3
2'-Methoxy-5'-chlorflavon
—— 5-((((2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)carbonyl)benzene-1,2,3-triyl triacetate 1262408-59-2 C28H24O13
5-((((2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)carbonyl)benzene-1,2,3-triyl triacetate
—— 6-Brom-2-o-chlorphenyl-8-methoxy-3-nitro-Δ<sup>3</sup>-chromen 57544-14-6 C16H11BrClNO4
6-Brom-2-o-chlorphenyl-8-methoxy-3-nitro-Δ<sup>3</sup>-chromen
—— 5,7,7'-Tris-methoxymethoxy-2',2'-dimethyl-8-(3-methyl-but-2-enyl)-2,3-dihydro-2'H-[2,6']bichromenyl-4-one 90632-25-0 C31H38O9
5,7,7'-Tris-methoxymethoxy-2',2'-dimethyl-8-(3-methyl-but-2-enyl)-2,3-dihydro-2'H-[2,6']bichromenyl-4-one
—— 5,7,7'-Tris-methoxymethoxy-2',2'-dimethyl-6-(3-methyl-but-2-enyl)-2,3-dihydro-2'H-[2,6']bichromenyl-4-one 90632-23-8 C31H38O9
5,7,7'-Tris-methoxymethoxy-2',2'-dimethyl-6-(3-methyl-but-2-enyl)-2,3-dihydro-2'H-[2,6']bichromenyl-4-one
—— 6-azido-3',4'-dibenzyloxyflavonol 1332713-53-7 C29H21N3O5
6-azido-3',4'-dibenzyloxyflavonol
—— 8-amino-2-benzo[1,3]dioxol-5-yl-chroman-4-one 114946-94-0 C16H13NO4
8-amino-2-benzo[1,3]dioxol-5-yl-chroman-4-one
—— 1417564-39-6 C18H16O5
—— (-)epicatechin-(-)-epicatechin 2271-17-2 C30H26O12
(-)epicatechin-(-)-epicatechin
—— 7'-Hydroxy-5,7-dimethoxy-2,2'-diphenyl-[8,8']bichromenyl-4,4'-dione 67948-44-1 C32H22O7
7'-Hydroxy-5,7-dimethoxy-2,2'-diphenyl-[8,8']bichromenyl-4,4'-dione
—— rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran 104761-78-6 C17H18O4
rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran
—— 7-hydroxy-2-(4-methoxy-phenyl)-5-methyl-chroman-4-one 51876-17-6 C17H16O4
7-hydroxy-2-(4-methoxy-phenyl)-5-methyl-chroman-4-one
—— Acetic acid 6-methoxy-7-methylsulfanylmethoxy-2-(4-methylsulfanylmethoxy-phenyl)-4-oxo-4H-chromen-5-yl ester 86756-11-8 C22H22O7S2
Acetic acid 6-methoxy-7-methylsulfanylmethoxy-2-(4-methylsulfanylmethoxy-phenyl)-4-oxo-4H-chromen-5-yl ester
—— 2-(2-chloro-4-aminophenyl)-4H-benzo[h]chromene-4-one 1393116-81-8 C19H12ClNO2
2-(2-chloro-4-aminophenyl)-4H-benzo[h]chromene-4-one
—— 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin 478241-34-8 C47H42O9
3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin
—— 2'-chloro-4'-nitroflavone 55736-95-3 C15H8ClNO4
2'-chloro-4'-nitroflavone
—— 2-benzoyloxy-3-<i>p</i>-tolyl-2,3-dihydro-1<i>H</i>-naphtho[1,2-<i>e</i>][1,3]oxazine 69025-39-4 C26H21NO3
2-benzoyloxy-3-<i>p</i>-tolyl-2,3-dihydro-1<i>H</i>-naphtho[1,2-<i>e</i>][1,3]oxazine
—— 7-Acetoxy-8-diacetoxymethylflavon 63790-44-3 C22H18O8
7-Acetoxy-8-diacetoxymethylflavon
—— 5-fluoro-2-morpholino-2-phenylbenzofuran-3(2H)-one 1627503-05-2 C18H16FNO3
5-fluoro-2-morpholino-2-phenylbenzofuran-3(2H)-one