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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
—— (2R,3S)-2-(3',4'-dimethoxyphenyl)chroman-3,5,7-triol 69912-76-1 C17H18O6
(2R,3S)-2-(3',4'-dimethoxyphenyl)chroman-3,5,7-triol
—— (2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-ol 664351-39-7 C47H46O8
(2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-ol
—— cinnamtannin D2 97233-47-1 C60H48O24
cinnamtannin D2
—— 2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl] 10586-06-8 C30H54O6Si5
2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl]
—— (2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-(2,2,2-trifluoroacetyl)flavan 89386-27-6 C52H43F3O7
(2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-(2,2,2-trifluoroacetyl)flavan
—— catechin-(4α->2)-phloroglucinol —— C21H18O9
catechin-(4α->2)-phloroglucinol
—— 6-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 78393-95-0 C19H21BrO6
6-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
—— catechin-3'-O-β-D-glucuronide 853728-25-3 C21H22O12
catechin-3'-O-β-D-glucuronide
—— 3,5,7,3',4'-penta-O-benzyl-8-formylcatechin 89385-18-2 C51H44O7
3,5,7,3',4'-penta-O-benzyl-8-formylcatechin
—— 6-C-benzyl-5,7,3',4'-tetra-O-benzyl-(+)-catechin 1007091-01-1 C50H44O6
6-C-benzyl-5,7,3',4'-tetra-O-benzyl-(+)-catechin
—— procyanidin B-3 7-O-β-D-glucopyranoside 105330-57-2 C36H36O17
procyanidin B-3 7-O-β-D-glucopyranoside
—— 4β-benzylsulfanylcatechin 37064-38-3 C22H20O6S
4β-benzylsulfanylcatechin
—— 5,7,3',4'-tetra-O-benzyl-8-allyl-catechin 919365-37-0 C46H42O6
5,7,3',4'-tetra-O-benzyl-8-allyl-catechin
—— (2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-7-methoxychroman-3,5-diol 300346-48-9 C29H24O6
(2R,3S)-2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-7-methoxychroman-3,5-diol
—— 3,5,7,3',4'-penta-O-benzylepicatechin 301539-02-6 C50H44O6
3,5,7,3',4'-penta-O-benzylepicatechin
—— 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin 919365-40-5 C74H64O10
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin
—— 3-Benzoyl-cianidanol 71634-84-9 C22H18O7
3-Benzoyl-cianidanol
—— (2S)-8-bromo-5,7,3',4'-tetramethoxyflavan 299412-52-5 C19H21BrO5
(2S)-8-bromo-5,7,3',4'-tetramethoxyflavan
—— 5,7,3',4'-tetra-O-benzyl-4β-allyl-catechin 919365-32-5 C46H42O6
5,7,3',4'-tetra-O-benzyl-4β-allyl-catechin
—— (2R,3S,8S,14S)-2,8-bis(3,4-dihydroxyphenyl)-10-methoxy-3,4-dihydro-2H,14H-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5-diol 944713-14-8 C31H26O10
(2R,3S,8S,14S)-2,8-bis(3,4-dihydroxyphenyl)-10-methoxy-3,4-dihydro-2H,14H-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5-diol
—— (1S,3R,11R,19R)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one 1201920-54-8 C24H18O9
(1S,3R,11R,19R)-19-(3,4-dihydroxyphenyl)-3,11,13,15-tetrahydroxy-2,18-dioxapentacyclo[14.3.1.03,11.04,9.012,17]icosa-4,6,8,12,14,16-hexaen-10-one
—— 5,7,3',4'-tetra-O-benzyl-4α-(1,3,5-tribenzylphloroglucinol)-catechin 157973-11-0 C70H60O9
5,7,3',4'-tetra-O-benzyl-4α-(1,3,5-tribenzylphloroglucinol)-catechin
—— (6aS,12aR)-6a,12a-trans-2,3,8,10-Tetrahydroxy-5,5-dimethyl-5,6a,7,12a-tetrahydro<1>benzopyrano<3,2-c><2>benzopyran 132125-04-3 C18H18O6
(6aS,12aR)-6a,12a-trans-2,3,8,10-Tetrahydroxy-5,5-dimethyl-5,6a,7,12a-tetrahydro<1>benzopyrano<3,2-c><2>benzopyran
—— (+)-catechin 8-C-β-D-glucopyranoside 105371-26-4 C21H24O11
(+)-catechin 8-C-β-D-glucopyranoside
—— (+)-catechin 4'-monosulfate 141136-40-5 C15H14O9S
(+)-catechin 4'-monosulfate
—— 5,7,3′,4′-tetra-O-benzyl-8-bromo-4β-(2-hydroxyethoxy)-(+)-catechin 923565-00-8 C45H41BrO8
5,7,3′,4′-tetra-O-benzyl-8-bromo-4β-(2-hydroxyethoxy)-(+)-catechin
—— 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin 919365-39-2 C74H64O10
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-8-allyl-catechin
—— (+)-catechin 7-α-O-glucoside 345319-75-7 C21H24O11
(+)-catechin 7-α-O-glucoside
—— [4,8]-2,3-cis-3,4-trans:2,3-cis-octa-O-benzyl-bi-(-)-epicatechin 223387-28-8 C86H74O12
[4,8]-2,3-cis-3,4-trans:2,3-cis-octa-O-benzyl-bi-(-)-epicatechin
—— 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-4β-allyl-catechin 919365-41-6 C74H64O10
5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-4β-allyl-catechin
—— (+)-catechin 3'-O-β-D-glucopyranoside 105330-51-6 C21H24O11
(+)-catechin 3'-O-β-D-glucopyranoside
—— (2R,3S)-2,3-trans-6-<(2R,3S,4R)-2,3-trans-3,4-cis-3,3',4',7-tetrahydroxyflavan-4-yl>-3,3',4',5,7-pentahydroxyflavan 104113-23-7 C30H26O11
(2R,3S)-2,3-trans-6-<(2R,3S,4R)-2,3-trans-3,4-cis-3,3',4',7-tetrahydroxyflavan-4-yl>-3,3',4',5,7-pentahydroxyflavan
—— (+)-catechin 3'-O-α-D-glucopyranoside 150337-42-1 C21H24O11
(+)-catechin 3'-O-α-D-glucopyranoside
—— 7-O-(β-Glcp-6-O-galloyl)-(+)-catechin-(4α->8)-(+)-catechin-(4α->8)-(-)-epigallocatechin 1333874-50-2 C58H52O28
7-O-(β-Glcp-6-O-galloyl)-(+)-catechin-(4α->8)-(+)-catechin-(4α->8)-(-)-epigallocatechin
—— (+)-catechin tetramethyl ether acetate 58065-35-3 C21H24O7
(+)-catechin tetramethyl ether acetate
—— 5,7,3′,4′-tetra-O-benzyl-8-bromo-(+)-catechin-(4α,8)-[5,7,3′,4′-tetra-O-benzyl-(+)-catechin] 923565-04-2 C86H73BrO12
5,7,3′,4′-tetra-O-benzyl-8-bromo-(+)-catechin-(4α,8)-[5,7,3′,4′-tetra-O-benzyl-(+)-catechin]
—— 5,3',4'-tri-O-benzyl-(+)-catechin 1007091-03-3 C36H32O6
5,3',4'-tri-O-benzyl-(+)-catechin
—— (R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-8-bromo-chroman-3-one 223387-38-0 C43H35BrO6
(R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-8-bromo-chroman-3-one
—— 5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin 256236-25-6 C45H42O8
5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin
—— epicatechin-(4β->6)-epicatechin 109582-69-6 C30H26O12
epicatechin-(4β->6)-epicatechin
—— (+)-catechin 5-O-α-D-glucoside 345319-76-8 C21H24O11
(+)-catechin 5-O-α-D-glucoside
—— 5,7,3',4'-tetra-O-benzyl-3-(3'',4'',5''-trimethoxybenzoyl)-(-)-epicatechin 1018677-68-3 C53H48O10
5,7,3',4'-tetra-O-benzyl-3-(3'',4'',5''-trimethoxybenzoyl)-(-)-epicatechin
—— B<sub>3</sub> dimer 660832-12-2 C30H26O12
B<sub>3</sub> dimer
—— (2S,3R,4S,5S,6R)-2-[[(2R,3R,4R)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 105330-39-0 C28H30O11S
(2S,3R,4S,5S,6R)-2-[[(2R,3R,4R)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— gambiriin D 1578134-37-8 C30H26O12
gambiriin D
—— bis-8,8'-catechinylmethane 81555-08-0 C31H28O12
bis-8,8'-catechinylmethane
—— (+)-catechin 6-C-β-D-glucopyranoside 105371-27-5 C21H24O11
(+)-catechin 6-C-β-D-glucopyranoside
—— 3',4',5,7-tetra-O-benzyl-8-bromocatechin 256236-21-2 C43H37BrO6
3',4',5,7-tetra-O-benzyl-8-bromocatechin
—— 8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 23671-72-9 C19H21BrO6
8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
—— (2S,3R,4S,5S,6R)-2-[[(2R,3R,4S)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 105330-39-0 C28H30O11S
(2S,3R,4S,5S,6R)-2-[[(2R,3R,4S)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol