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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-bis-benzoyloxy-2-(3-benzoyloxy-4-benzyloxy-phenyl)-7-benzyloxy-chromen-4-one 53473-13-5 C50H34O10
3,5-bis-benzoyloxy-2-(3-benzoyloxy-4-benzyloxy-phenyl)-7-benzyloxy-chromen-4-one
—— (2R,3S,4S)-2-(3,4-Dimethoxy-phenyl)-5,7-dimethoxy-4-phenylsulfanyl-chroman-3-ol 55539-55-4 C25H26O6S
(2R,3S,4S)-2-(3,4-Dimethoxy-phenyl)-5,7-dimethoxy-4-phenylsulfanyl-chroman-3-ol
—— Dihydro-iso-sericetin-methylether 40603-70-1 C26H28O5
Dihydro-iso-sericetin-methylether
—— 8-(3-Methoxy-phenyl)-4-methyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 115665-02-6 C20H16O5
8-(3-Methoxy-phenyl)-4-methyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione
—— 4',5,7-tris(trimethylsilyl)naringenin 105393-75-7 C24H36O5Si3
4',5,7-tris(trimethylsilyl)naringenin
—— 8-(3",3"-dimethylallyl)-5,7,3',4'-tetrakis(methoxymethoxy)flavanone 132246-43-6 C28H36O10
8-(3",3"-dimethylallyl)-5,7,3',4'-tetrakis(methoxymethoxy)flavanone
—— Micranthoside acetate 79860-35-8 C46H52O25
Micranthoside acetate
—— Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-[5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-2-acetoxymethyl-5-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 61303-33-1 C46H52O25
Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-[5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-4-oxo-chroman-7-yloxy]-2-acetoxymethyl-5-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
—— Acetic acid 7-acetoxy-2-[3-acetoxy-4-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester 53473-12-4 C49H52O28
Acetic acid 7-acetoxy-2-[3-acetoxy-4-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester
—— 5,7-Dimethoxyflavon-8-carbonsaeure 39827-84-4 C18H18O5
5,7-Dimethoxyflavon-8-carbonsaeure
—— 7,7-diphenyl-7H-3-methylfuro[3',2',:5,6]naphtho[2,1-b]pyran 173301-11-6 C28H20O2
7,7-diphenyl-7H-3-methylfuro[3',2',:5,6]naphtho[2,1-b]pyran
—— 5-hydroxy-3-methoxy-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 55929-16-3 C27H28O6
5-hydroxy-3-methoxy-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
—— 2-(2,4-Dimethoxy-phenyl)-8-(5-hydroxy-2-isopropenyl-5-methyl-hexyl)-5,7-dimethoxy-chroman-4-one 51857-07-9 C29H38O7
2-(2,4-Dimethoxy-phenyl)-8-(5-hydroxy-2-isopropenyl-5-methyl-hexyl)-5,7-dimethoxy-chroman-4-one
—— Acetic acid 7-acetoxy-2-[4-acetoxy-3-((3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester 53604-82-3 C49H52O28
Acetic acid 7-acetoxy-2-[4-acetoxy-3-((3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-3-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester
—— 2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-hydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2H-1-benzopyran 361391-17-5 C24H18ClF3O3S
2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-hydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2H-1-benzopyran
—— Flavon-7-oxyacetyl(N-methylpiperazid) 101812-07-1 C22H22N2O4
Flavon-7-oxyacetyl(N-methylpiperazid)
—— 1,11-O-(di-tert-butylsilylene)-1,7,11-trideacetylpyripyropene 1163689-87-9 C33H47NO7Si
1,11-O-(di-tert-butylsilylene)-1,7,11-trideacetylpyripyropene
—— 3,7-Di-O-Methyl-6,8-diprenylgalangin 40603-69-8 C27H30O5
3,7-Di-O-Methyl-6,8-diprenylgalangin
—— 4-α-p-Tolylthioflavan 55539-22-5 C22H20OS
4-α-p-Tolylthioflavan
—— Ugonin-A-trimethylether 50939-08-7 C28H32O6
Ugonin-A-trimethylether
—— 2-[4-(4-acetylamino-benzenesulfonylamino)-phenyl]-3-hydroxy-chromen-4-one 42520-00-3 C23H18N2O6S
2-[4-(4-acetylamino-benzenesulfonylamino)-phenyl]-3-hydroxy-chromen-4-one
—— 2-[3-nitro-4-(phenylhydrazono-methyl)-phenyl]-chromen-4-one 116601-36-6 C22H15N3O4
2-[3-nitro-4-(phenylhydrazono-methyl)-phenyl]-chromen-4-one
—— 3-(3-bromophenyl)-2-(4-iodophenyl)-6-((tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one 1443992-96-8 C26H22BrIO4
3-(3-bromophenyl)-2-(4-iodophenyl)-6-((tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
—— Acetic acid 2,3,3-trimethyl-9-oxo-7-phenyl-2,3-dihydro-9H-furo[2,3-f]chromen-4-yl ester 55390-58-4 C22H20O5
Acetic acid 2,3,3-trimethyl-9-oxo-7-phenyl-2,3-dihydro-9H-furo[2,3-f]chromen-4-yl ester
—— 6-Brom-7-methoxy-3-nitro-2-phenyl-Δ<sup>3</sup>-chromen 57543-91-6 C16H12BrNO4
6-Brom-7-methoxy-3-nitro-2-phenyl-Δ<sup>3</sup>-chromen
—— Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{5,7-diacetoxy-2-[4-acetoxy-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-4H-chromen-6-yl}-tetrahydro-pyran-3-yl ester 53209-21-5 C49H52O27
Acetic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{5,7-diacetoxy-2-[4-acetoxy-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-4H-chromen-6-yl}-tetrahydro-pyran-3-yl ester
—— 5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-9,10-dihydro-8<i>H</i>-pyrano[2,3-<i>f</i>]chromen-4-one 40603-79-0 C21H20O5
5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-9,10-dihydro-8<i>H</i>-pyrano[2,3-<i>f</i>]chromen-4-one
—— 5-chloro-3-hydroxy-7-methyl-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 1441771-91-0 C19H17ClO6
5-chloro-3-hydroxy-7-methyl-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
—— Cirsilineol-4'-glucosid-tetraacetat 55274-35-6 C32H34O16
Cirsilineol-4'-glucosid-tetraacetat
—— 3-O-Methyl-6-prenylgalangin 40603-67-6 C21H20O5
3-O-Methyl-6-prenylgalangin
—— 2.4-trans-7.8.4'-Trimethoxyflavan-4-ol 50403-56-0 C18H20O5
2.4-trans-7.8.4'-Trimethoxyflavan-4-ol
—— [5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine 52477-11-9 C24H21N3O3
[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine
—— Ugonin A-triacetat 50939-09-8 C31H32O9
Ugonin A-triacetat
—— 6-methyl-6-phenyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene 1415605-90-1 C17H16O3
6-methyl-6-phenyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene
—— 8,9-dihydro-8-(4-methoxyphenyl)-4-methyl-2H,10H-benzo<1,2-b:3,4-b'>dipyran-2,10-dione 115665-03-7 C20H16O5
8,9-dihydro-8-(4-methoxyphenyl)-4-methyl-2H,10H-benzo<1,2-b:3,4-b'>dipyran-2,10-dione
—— (2R,3R,4S)-2-(3,4-Dihydroxy-phenyl)-4-(2,4,6-trihydroxy-3-methyl-phenyl)-chroman-3,5,7-triol 61541-00-2 C22H20O9
(2R,3R,4S)-2-(3,4-Dihydroxy-phenyl)-4-(2,4,6-trihydroxy-3-methyl-phenyl)-chroman-3,5,7-triol
—— Acetic acid 7-acetoxy-3-methoxy-6-(3-methyl-but-2-enyl)-4-oxo-2-phenyl-4H-chromen-5-yl ester 40603-68-7 C25H24O7
Acetic acid 7-acetoxy-3-methoxy-6-(3-methyl-but-2-enyl)-4-oxo-2-phenyl-4H-chromen-5-yl ester
—— 5,7,5',7'-tetraacetoxy-2'-(3,4-diacetoxy-phenyl)-2,8'-(4,5-diacetoxy-<i>m</i>-phenylene)-bis-chromen-4-one 52222-76-1 C46H34O20
5,7,5',7'-tetraacetoxy-2'-(3,4-diacetoxy-phenyl)-2,8'-(4,5-diacetoxy-<i>m</i>-phenylene)-bis-chromen-4-one
—— 7-acetoxy-2-[2-(1-hydroxy-1-methyl-ethyl)-7-(3-methyl-but-2-enyl)-2,3-dihydro-benzofuran-5-yl]-8-(3-methyl-but-2-enyl)-chroman-4-one 50675-34-8 C32H38O6
7-acetoxy-2-[2-(1-hydroxy-1-methyl-ethyl)-7-(3-methyl-but-2-enyl)-2,3-dihydro-benzofuran-5-yl]-8-(3-methyl-but-2-enyl)-chroman-4-one
—— 1,13-bis[4'-(6,8-dichloro-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane 958457-98-2 C38H30Cl4O9
1,13-bis[4'-(6,8-dichloro-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane
—— 3',4',5-Triacetoxy-7-methoxy-3-O-octa-O-acetyl-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid 83170-23-4 C56H64O31
3',4',5-Triacetoxy-7-methoxy-3-O-octa-O-acetyl-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid
—— 3,5-Dihydroxy-7-methoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one 154048-27-8 C19H18O8
3,5-Dihydroxy-7-methoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one
—— 7(1H)-(3-chloropropyloxyimino)-4,5-dimethoxy-1a,7a-dihydro-1a-phenylcyclopropa[b]chromen 139770-92-6 C21H22ClNO4
7(1H)-(3-chloropropyloxyimino)-4,5-dimethoxy-1a,7a-dihydro-1a-phenylcyclopropa[b]chromen
—— 3,4'-Diacetoxy-5,6,7-trimethoxy-flavon 52377-96-5 C22H20O9
3,4'-Diacetoxy-5,6,7-trimethoxy-flavon
—— Proanthocyanidin-A2-octamethylether 55626-26-1 C38H40O12
Proanthocyanidin-A2-octamethylether
—— 5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 40603-81-4 C21H18O5
5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— 60296-83-5 C29H17NO6
—— (2S)-5-hydroxy-7-methoxy-8-methylflavanone 55869-77-7 C17H16O4
(2S)-5-hydroxy-7-methoxy-8-methylflavanone
—— 5,7-dimethoxy-6-(methoxymethoxy)-2-phenylchromen-4-one 170234-84-1 C19H18O6
5,7-dimethoxy-6-(methoxymethoxy)-2-phenylchromen-4-one
—— 1a,7a-Dihydro-7(1H)-(3-dimethylamino-2-methylpropyloxyimino)-1a-phenylcyclopropa[b]chromen 114368-29-5 C22H26N2O2
1a,7a-Dihydro-7(1H)-(3-dimethylamino-2-methylpropyloxyimino)-1a-phenylcyclopropa[b]chromen