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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
—— 4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)-benzene-1,3-disulfonic acid dimethyl ester 54110-20-2 C17H14O9S2
4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)-benzene-1,3-disulfonic acid dimethyl ester
—— 8-bromomethyl-3-methoxy-2-phenylchromen-4-one 87165-69-3 C17H13BrO3
8-bromomethyl-3-methoxy-2-phenylchromen-4-one
—— 7-Methoxy-4α-phenylsulfonylflavan 55539-43-0 C22H20O4S
7-Methoxy-4α-phenylsulfonylflavan
—— apigenin 7-O-peracetyl-β-L-glucoside 679398-71-1 C29H28O14
apigenin 7-O-peracetyl-β-L-glucoside
—— Flavonsulfonsaeure-2'-methylester 54110-17-7 C16H12O6S
Flavonsulfonsaeure-2'-methylester
—— Proanthocyanidin-A2-octamethylether-acetat 55626-27-2 C40H42O13
Proanthocyanidin-A2-octamethylether-acetat
—— 5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 40603-72-3 C21H20O5
5-hydroxy-3-methoxy-8,8-dimethyl-2-phenyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— methyl (2R,4R)-6-chloro-4-phenyl-4-prop-2-enyl-1,3-benzodioxine-2-carboxylate 73051-06-6 C19H17ClO4
methyl (2R,4R)-6-chloro-4-phenyl-4-prop-2-enyl-1,3-benzodioxine-2-carboxylate
—— 1318698-20-2 C29H26O4
—— 3-(cyanomethyl)-4',7-dimethoxyflavone 80907-34-2 C19H15NO4
3-(cyanomethyl)-4',7-dimethoxyflavone
—— Acetic acid (2R,3R,4S)-2-(3,4-dimethoxy-phenyl)-3-hydroxy-7,8-dimethoxy-chroman-4-yl ester 53388-55-9 C21H24O8
Acetic acid (2R,3R,4S)-2-(3,4-dimethoxy-phenyl)-3-hydroxy-7,8-dimethoxy-chroman-4-yl ester
—— 7-Methoxy-4α-phenylthioflavan 55539-25-8 C22H20O2S
7-Methoxy-4α-phenylthioflavan
—— 5-Acetoxystrobopinin-7-methylether 55743-18-5 C19H18O5
5-Acetoxystrobopinin-7-methylether
—— [5-(4-Nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine 52477-12-0 C23H18N4O4
[5-(4-Nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine
—— (-)-balsacone D 1572949-01-9 C24H22O5
(-)-balsacone D
—— 5-hydroxy-8,8-dimethyl-2-phenyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 50830-97-2 C20H18O4
5-hydroxy-8,8-dimethyl-2-phenyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— (+)-balsacone D 1572949-02-0 C24H22O5
(+)-balsacone D
—— 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 679398-78-8 C29H30O14
4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin
—— 6-acetoxy-5-hydroxy-3,4',7-trimethoxyflavone 154047-87-7 C20H18O8
6-acetoxy-5-hydroxy-3,4',7-trimethoxyflavone
—— Methyl-5-carbomethoxymethylflavon 51281-79-9 C18H14O4
Methyl-5-carbomethoxymethylflavon
—— Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-{3,5-diacetoxy-4-[3-(3-acetoxy-4-methoxy-phenyl)-propionyl]-phenoxy}-5-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 61284-21-7 C46H54O24
Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-{3,5-diacetoxy-4-[3-(3-acetoxy-4-methoxy-phenyl)-propionyl]-phenoxy}-5-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
—— 2-(3-iodo-4,5-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one 52222-79-4 C19H17IO6
2-(3-iodo-4,5-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one
—— 7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 679398-73-3 C43H46O23
7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
—— Lupinifolindiacetat 55730-71-7 C29H30O7
Lupinifolindiacetat
—— 4-(3-hydroxy-4-oxo-4<i>H</i>-chromen-2-yl)-benzenesulfonic acid methyl ester 54110-19-9 C16H12O6S
4-(3-hydroxy-4-oxo-4<i>H</i>-chromen-2-yl)-benzenesulfonic acid methyl ester
—— Acetic acid 2-(3,4-diacetoxy-phenyl)-4-oxo-3,7-bis-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester 53473-14-6 C49H52O28
Acetic acid 2-(3,4-diacetoxy-phenyl)-4-oxo-3,7-bis-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4H-chromen-5-yl ester
—— 5-acetoxy-2-(4-acetoxy-phenyl)-8,8-dimethyl-2,3,9,10-tetrahydro-8<i>H</i>-pyrano[2,3-<i>f</i>]chromen-4-one 70872-23-0 C24H24O7
5-acetoxy-2-(4-acetoxy-phenyl)-8,8-dimethyl-2,3,9,10-tetrahydro-8<i>H</i>-pyrano[2,3-<i>f</i>]chromen-4-one
—— 6-hydroxyluteolin 7,3',4'-trimethyl ether 41087-97-2 C24H26O12
6-hydroxyluteolin 7,3',4'-trimethyl ether
—— 3',4',5,7-Tetramethoxy-8-C-methylflavanon 111497-74-6 C20H22O6
3',4',5,7-Tetramethoxy-8-C-methylflavanon
—— 3,5-dihydroxy-7-(2-hydroxy-ethoxy)-2-[4-hydroxy-3-(2-hydroxy-ethoxy)-phenyl]-chromen-4-one 50846-14-5 C19H18O9
3,5-dihydroxy-7-(2-hydroxy-ethoxy)-2-[4-hydroxy-3-(2-hydroxy-ethoxy)-phenyl]-chromen-4-one
—— 6-bromo-2-(2,4-dichlorophenyl)-2,3-dihydro-2'H-spiro[chromene-4,5'-[1,3]oxazolidin]-2'-one 1313611-93-6 C17H12BrCl2NO3
6-bromo-2-(2,4-dichlorophenyl)-2,3-dihydro-2'H-spiro[chromene-4,5'-[1,3]oxazolidin]-2'-one
—— [5-(4-Methoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine 52477-14-2 C24H21N3O2S
[5-(4-Methoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine
—— 5,9-dimethoxy-2,2-dimethyl-8-phenyl-3,4-dihydro-2<i>H</i>-pyrano[2,3-<i>f</i>]chromen-10-one 40629-20-7 C22H22O5
5,9-dimethoxy-2,2-dimethyl-8-phenyl-3,4-dihydro-2<i>H</i>-pyrano[2,3-<i>f</i>]chromen-10-one
—— 5-hydroxy-3-methoxy-2-(4-methoxy-phenyl)-8,8-dimethyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 55929-17-4 C22H22O6
5-hydroxy-3-methoxy-2-(4-methoxy-phenyl)-8,8-dimethyl-7,8-dihydro-6<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— 3"-(E)-cinnamoylquercitrin 1242284-56-5 C30H26O12
3"-(E)-cinnamoylquercitrin
—— 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 679398-77-7 C35H44O14Si
7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin
—— Cirsiliol-4'-glucosid 41087-98-3 C23H24O12
Cirsiliol-4'-glucosid
—— 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,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 61301-29-9 C44H50O23
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,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
—— Acetylpalustaside 59379-76-9 C2H4O2*C27H30O16
Acetylpalustaside
—— [2-Methoxy-4-oxo-2-phenyl-chroman-(3E)-ylidene]-acetic acid ethyl ester 50525-99-0 C20H18O5
[2-Methoxy-4-oxo-2-phenyl-chroman-(3E)-ylidene]-acetic acid ethyl ester
—— [5-(4-Nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine 52477-15-3 C23H18N4O3S
[5-(4-Nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-(2-phenyl-chroman-4-yl)-amine
—— 2-(2-(2,5-dihydroxyphenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl)acetic acid 1389341-98-3 C17H12O7
2-(2-(2,5-dihydroxyphenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl)acetic acid
—— Acetic acid 3-hydroxy-7-methoxy-2-(4-methoxy-phenyl)-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester 154048-03-0 C26H22O10S
Acetic acid 3-hydroxy-7-methoxy-2-(4-methoxy-phenyl)-4-oxo-5-(toluene-4-sulfonyloxy)-4H-chromen-6-yl ester
—— 2-benzoyloxy-6-methoxycoumaran-3-one 74767-54-7 C16H12O5
2-benzoyloxy-6-methoxycoumaran-3-one
—— Acetic acid (S)-5-hydroxy-2-phenyl-chroman-7-yl ester 140479-95-4 C17H16O4
Acetic acid (S)-5-hydroxy-2-phenyl-chroman-7-yl ester
—— 4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 679398-81-3 C29H28O14
4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
—— 1-{4-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2,6-dihydroxy-phenyl}-3-(3-hydroxy-4-methoxy-phenyl)-propan-1-one 61284-20-6 C28H36O15
1-{4-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2,6-dihydroxy-phenyl}-3-(3-hydroxy-4-methoxy-phenyl)-propan-1-one
—— 2,4-trans-4'-Methoxy-7-methyl-4-acetylflavan 41786-56-5 C19H20O4
2,4-trans-4'-Methoxy-7-methyl-4-acetylflavan
—— 6-Bromo-3-chloro-2-(4-methoxy-phenyl)-chromen-4-one 75595-42-5 C16H10BrClO3
6-Bromo-3-chloro-2-(4-methoxy-phenyl)-chromen-4-one
—— 6",6"-dimethylpyrano<2",3":7,6>-3',4'-methylenedioxyflavanone 78045-77-9 C21H18O5
6",6"-dimethylpyrano<2",3":7,6>-3',4'-methylenedioxyflavanone