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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-[(2S)-5-acetyloxy-7-methoxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl] acetate 3064-16-2 C20H18O7
[4-[(2S)-5-acetyloxy-7-methoxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl] acetate
—— 4'-Acetoxy-3',5,7-trimethoxy-flavon 1429-10-3 C20H18O7
4'-Acetoxy-3',5,7-trimethoxy-flavon
—— 2',3',4'-trimethoxy-3-methylflavone-8-carboxylic acid N,N-diethylamide 90102-09-3 C24H27NO6
2',3',4'-trimethoxy-3-methylflavone-8-carboxylic acid N,N-diethylamide
—— 1,3-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 874365-10-3 C44H26Br2F2O2
1,3-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene
—— 2-[4-Methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-8,8-dimethyl-2,3-dihydro-8H-pyrano[2,3-f]chromen-4-one 237769-20-9 C27H30O5
2-[4-Methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-8,8-dimethyl-2,3-dihydro-8H-pyrano[2,3-f]chromen-4-one
—— 2',3,7,-trihydroxy-4',5,5',6,8-pentamethoxyflavone 107644-01-9 C20H20O10
2',3,7,-trihydroxy-4',5,5',6,8-pentamethoxyflavone
—— 4'-isopropyl-3-methylflavone-8-carboxylic acid N-cyclohexylamide 90102-31-1 C26H29NO3
4'-isopropyl-3-methylflavone-8-carboxylic acid N-cyclohexylamide
—— 6-amino-7-methoxy-2-(2-methoxy-phenyl)-chroman-4-one 109395-47-3 C17H17NO4
6-amino-7-methoxy-2-(2-methoxy-phenyl)-chroman-4-one
—— 6-Methoxy-5.7.3'.4'-tetraethoxy-3-acetoxyflavon 13180-08-0 C26H30O9
6-Methoxy-5.7.3'.4'-tetraethoxy-3-acetoxyflavon
—— (+/-)-7-Acetoxy-2-<4-acetoxy-phenyl>-5-hydroxy-3-jod-chroman-4-on 5224-63-5 C19H15IO7
(+/-)-7-Acetoxy-2-<4-acetoxy-phenyl>-5-hydroxy-3-jod-chroman-4-on
—— 3-iodo-2-(4-fluoro)phenyl-4H-furo[2,3-b]benzopyran-4-one 1279109-06-6 C17H8FIO3
3-iodo-2-(4-fluoro)phenyl-4H-furo[2,3-b]benzopyran-4-one
—— 1-(3,4-Dimethoxy-phenyl)-2-[2-(3,4-dimethoxy-phenyl)-7-methoxy-4-oxo-4H-chromen-3-yl]-3-(2-hydroxy-4-methoxy-phenyl)-propane-1,3-dione 132124-42-6 C36H32O11
1-(3,4-Dimethoxy-phenyl)-2-[2-(3,4-dimethoxy-phenyl)-7-methoxy-4-oxo-4H-chromen-3-yl]-3-(2-hydroxy-4-methoxy-phenyl)-propane-1,3-dione
—— 5-(6-iodohexoxy)flavone 139653-21-7 C21H21IO3
5-(6-iodohexoxy)flavone
—— 2-methyl-4-oxo-11-phenyl-3,4,5,6-tetrahydro-2<i>H</i>-2,6-methano-benzo[<i>g</i>][1,3]oxazocine-5-carboxylic acid ethyl ester 53635-60-2 C21H21NO4
2-methyl-4-oxo-11-phenyl-3,4,5,6-tetrahydro-2<i>H</i>-2,6-methano-benzo[<i>g</i>][1,3]oxazocine-5-carboxylic acid ethyl ester
—— 6-(β-D-Galaktopyranosylamino)-flavanon 14904-79-1 C21H23NO7
6-(β-D-Galaktopyranosylamino)-flavanon
—— 6-Chlor-3a-jod-4'-methoxy-flavanon 14166-10-0 C16H12ClIO3
6-Chlor-3a-jod-4'-methoxy-flavanon
—— Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3,6,7-trimethoxy-4-oxo-4H-chromen-5-yl ester 124909-90-6 C27H26O10S
Toluene-4-sulfonic acid 2-(3,4-dimethoxy-phenyl)-3,6,7-trimethoxy-4-oxo-4H-chromen-5-yl ester
—— 8-Chlor-6-fluorflavanon 4257-42-5 C15H10ClFO2
8-Chlor-6-fluorflavanon
—— 2-(4-Methoxy-phenyl)-3-hydroxy-4-oxo-6-methoxy-7-brom-4H-chromen 6601-58-7 C17H13BrO5
2-(4-Methoxy-phenyl)-3-hydroxy-4-oxo-6-methoxy-7-brom-4H-chromen
—— 3e-Brom-6-methyl-flavanon 1195683-26-1 C16H13BrO2
3e-Brom-6-methyl-flavanon
—— 6,4'-Bisacetamino-flavonol 6608-12-4 C19H16N2O5
6,4'-Bisacetamino-flavonol
—— 3a-Iod-6-chlor-flavanon 14166-09-7 C15H10ClIO2
3a-Iod-6-chlor-flavanon
—— 6-(2-(naphthalen-2-yl)-2-oxoethoxy)-2-phenyl-4H-chromen-4-one 1070399-39-1 C27H18O4
6-(2-(naphthalen-2-yl)-2-oxoethoxy)-2-phenyl-4H-chromen-4-one
—— 7-O-benzyl-4'-O-methoxymethylapigenin 1104802-60-9 C24H20O6
7-O-benzyl-4'-O-methoxymethylapigenin
—— Methyl 2-((3,7-Bis(benzyloxy)-2-(3,4-bis(benzyloxy)-phenyl)-4-oxo-4H-chromen-5-yl)oxy)acetate 1144104-67-5 C46H38O9
Methyl 2-((3,7-Bis(benzyloxy)-2-(3,4-bis(benzyloxy)-phenyl)-4-oxo-4H-chromen-5-yl)oxy)acetate
—— (2R,3S,4R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-(2,4,6-tris(benzyloxy)phenyl)chroman-3-yl acetate 950822-47-6 C72H62O10
(2R,3S,4R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-(2,4,6-tris(benzyloxy)phenyl)chroman-3-yl acetate
—— 3,7-di-O-octanoyl-(+)-D-catechin 904705-96-0 C31H42O8
3,7-di-O-octanoyl-(+)-D-catechin
—— 5-O-methylquercetin tetraacetate 1592-67-2 C24H20O11
5-O-methylquercetin tetraacetate
—— cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-glucopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 1104564-04-6 C61H67O34
cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-glucopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]
—— 2-{[3-(4-oxo-4H-chromen-2-yl)phenyl]amino}acetic acid 1356490-76-0 C17H13NO4
2-{[3-(4-oxo-4H-chromen-2-yl)phenyl]amino}acetic acid
—— 10,11-Dimethoxy-5,5-bis(4-methoxyphenyl)-22,22-dimethyl-6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8,10,12,15,17,19-nonaene 945424-80-6 C39H36O5
10,11-Dimethoxy-5,5-bis(4-methoxyphenyl)-22,22-dimethyl-6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8,10,12,15,17,19-nonaene
—— 1404170-11-1 C28H24O3
—— 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-(2,4,6-trihydroxy-3,5-(didodecanoyl)-phenyl)chroman 144337-17-7 C59H74O8
7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-(2,4,6-trihydroxy-3,5-(didodecanoyl)-phenyl)chroman
—— 5,7,4'-triacetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-8-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)flavone 1254210-62-2 C46H48O24
5,7,4'-triacetoxy-6-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-8-C-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)flavone
—— 5-((2S,4S)-2-(3-(((R)-1-(4-fluoro-3-methoxyphenyl)ethyl)amino)propyl)chroman-4-yl)-2-methylbenzoic acid hydrochloride 1451373-78-6 C29H32FNO4*ClH
5-((2S,4S)-2-(3-(((R)-1-(4-fluoro-3-methoxyphenyl)ethyl)amino)propyl)chroman-4-yl)-2-methylbenzoic acid hydrochloride
—— 7,4'-dimethoxy-3-methylflavone 18651-17-7 C18H16O4
7,4'-dimethoxy-3-methylflavone
—— 2-(3,4-Bis-benzyloxy-phenyl)-6-decyloxy-5,7-dimethoxy-chromen-4-one 103777-13-5 C41H46O7
2-(3,4-Bis-benzyloxy-phenyl)-6-decyloxy-5,7-dimethoxy-chromen-4-one
—— Resokaempferol 3-glucuronide 1242087-66-6 C21H18O11
Resokaempferol 3-glucuronide
—— 5,5-Bis(4-methoxyphenyl)-10,11-bis(methylsulfanyl)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'-cyclohexane] 1263318-43-9 C41H38O3S2
5,5-Bis(4-methoxyphenyl)-10,11-bis(methylsulfanyl)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'-cyclohexane]
—— 3',4',7-Tri-O-methylorientin 4261-43-2 C24H26O11
3',4',7-Tri-O-methylorientin
—— 5-methoxy-8-(4-methoxy-phenyl)-2,2-dimethyl-3,4-dihydro-2<i>H</i>-pyrano[2,3-<i>f</i>]chromen-10-one 68634-30-0 C22H22O5
5-methoxy-8-(4-methoxy-phenyl)-2,2-dimethyl-3,4-dihydro-2<i>H</i>-pyrano[2,3-<i>f</i>]chromen-10-one
—— 7-carboxymethoxy-6,8-diallyl-5-hydroxy-2-(2-allyl-3-carboxymethoxy-4-methoxyphenyl)-4H-1-benzopyran-4-one 198886-07-6 C29H28O10
7-carboxymethoxy-6,8-diallyl-5-hydroxy-2-(2-allyl-3-carboxymethoxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
—— 3-Chlor-7-methylflavon 36695-02-0 C16H11ClO2
3-Chlor-7-methylflavon
—— 4-[7-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-yl]benzoic acid 57162-04-6 C33H34O8
4-[7-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-yl]benzoic acid
—— 1-(2-methylphenyl)-3-[[2-[(8-methyl-2-phenyl-3,4-dihydro-2H-chromen-7-yl)oxy]acetyl]amino]thiourea 122484-05-3 C26H27N3O3S
1-(2-methylphenyl)-3-[[2-[(8-methyl-2-phenyl-3,4-dihydro-2H-chromen-7-yl)oxy]acetyl]amino]thiourea
—— 3-(3-fluoro-4-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol hydrochloride 1352307-46-0 C30H32FNO4*ClH
3-(3-fluoro-4-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol hydrochloride
—— 2-(4-(2-(azocan-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol trifluoroacetate 1352307-33-5 C2HF3O2*C31H35NO4
2-(4-(2-(azocan-1-yl)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol trifluoroacetate
—— 3-bromo-3'-nitroacacetin 7-benzyl ether 890661-87-7 C23H16BrNO7
3-bromo-3'-nitroacacetin 7-benzyl ether
—— 6-chloro-3-iodo-2-phenyl-4H-furo[2,3-b]benzopyran-4-one 1279109-10-2 C17H8ClIO3
6-chloro-3-iodo-2-phenyl-4H-furo[2,3-b]benzopyran-4-one
—— 6-chloro-3-(p-fluorobenzyloxy)-2-phenyl-4-oxo-4H-1-benzopyran 134145-79-2 C22H14ClFO3
6-chloro-3-(p-fluorobenzyloxy)-2-phenyl-4-oxo-4H-1-benzopyran