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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
—— 2-(2-butoxy-phenyl)-4-oxo-4-<i>H</i>-chromene-6-carboxylic acid 57009-17-3 C20H18O5
2-(2-butoxy-phenyl)-4-oxo-4-<i>H</i>-chromene-6-carboxylic acid
—— O7-nitrooxyethyl-O3',O4'-diphenylmethane luteolin 1443679-17-1 C30H21NO9
O7-nitrooxyethyl-O3',O4'-diphenylmethane luteolin
—— 5-bromo-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 1441772-18-4 C18H15BrO6
5-bromo-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one
—— 5,7,4'-trihydroxy-3'-methoxy-6,8-di-C-(β-D-xylopyranosyl)flavanone 1253227-60-9 C26H30O14
5,7,4'-trihydroxy-3'-methoxy-6,8-di-C-(β-D-xylopyranosyl)flavanone
—— Benzyl-((2R,3S)-2-phenyl-chroman-3-yl)-amine 81289-32-9 C22H21NO
Benzyl-((2R,3S)-2-phenyl-chroman-3-yl)-amine
—— 3-bromo-2-(3-bromo-4-methoxy-phenyl)-chromen-4-one 131866-10-9 C16H10Br2O3
3-bromo-2-(3-bromo-4-methoxy-phenyl)-chromen-4-one
—— 2-(4-Bromo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one 1242983-41-0 C23H24BrNO5
2-(4-Bromo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one
—— 2-(2-chlorophenyl)-5,7-dimethoxy-8-oxiranylmethyl-4H-1-benzopyran-4-one 952677-99-5 C20H17ClO5
2-(2-chlorophenyl)-5,7-dimethoxy-8-oxiranylmethyl-4H-1-benzopyran-4-one
—— spiro <3-(2-phenyl)-benzopyran>-5'-(N-hydroxy)-pyrrolidin-2'-one 131391-93-0 C18H17NO3
spiro <3-(2-phenyl)-benzopyran>-5'-(N-hydroxy)-pyrrolidin-2'-one
—— (2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(sec-butylcarbamate) 1374854-19-9 C59H62N2O12
(2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(sec-butylcarbamate)
—— (2S,3R)-trans-3',4'-dimethoxy-7-(phenylmethoxy)-flavan-3-ol 1196870-44-6 C24H24O5
(2S,3R)-trans-3',4'-dimethoxy-7-(phenylmethoxy)-flavan-3-ol
—— 19-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,21-dioxaheptacyclo[15.11.0.02,10.03,8.011,16.020,28.022,27]octacosa-1(28),2(10),3,5,7,11(16),12,17,19,22,24,26-dodecaene-9,3'-cyclohexane] 1259401-10-9 C50H46O5
19-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,21-dioxaheptacyclo[15.11.0.02,10.03,8.011,16.020,28.022,27]octacosa-1(28),2(10),3,5,7,11(16),12,17,19,22,24,26-dodecaene-9,3'-cyclohexane]
—— 6-bromo-2-(2-methoxy-phenyl)-benzo[<i>h</i>]chromen-4-one 112553-94-3 C20H13BrO3
6-bromo-2-(2-methoxy-phenyl)-benzo[<i>h</i>]chromen-4-one
—— (2<i>R</i>)-2<i>r</i>-(3,4-bis-methanesulfonyloxy-phenyl)-5,7-bis-methanesulfonyloxy-chroman-3<i>t</i>-ol 111442-76-3 C19H22O14S4
(2<i>R</i>)-2<i>r</i>-(3,4-bis-methanesulfonyloxy-phenyl)-5,7-bis-methanesulfonyloxy-chroman-3<i>t</i>-ol
—— 8-fluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3c]chromen-2-ol 554430-75-0 C29H28FNO4
8-fluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3c]chromen-2-ol
—— 7-Benzyloxy-5,6,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 10176-76-8 C26H24O7
7-Benzyloxy-5,6,8-trimethoxy-2-(4-methoxy-phenyl)-chromen-4-one
—— 6,4'-dimethylflavanone 123743-13-5 C17H16O2
6,4'-dimethylflavanone
—— 70189-45-6 C28H30O11
—— 7,8,3',4'-Tetramethoxy-3-phenylflavon 65894-04-4 C25H22O6
7,8,3',4'-Tetramethoxy-3-phenylflavon
—— 5,7-Dihydroxy-2-phenyl-6-(phenyl-piperidin-1-yl-methyl)-8-piperidin-1-ylmethyl-chromen-4-one 67513-72-8 C33H36N2O4
5,7-Dihydroxy-2-phenyl-6-(phenyl-piperidin-1-yl-methyl)-8-piperidin-1-ylmethyl-chromen-4-one
—— 6-carboxy-2'-nitro-flavone 57009-55-9 C16H9NO6
6-carboxy-2'-nitro-flavone
—— 4-Carboxy-6,7-dihydroxy-2-phenyl-chromenylium; chloride 66686-18-8 C16H11O5*Cl
4-Carboxy-6,7-dihydroxy-2-phenyl-chromenylium; chloride
—— 11-Cyclohexyl-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane] 1263318-13-3 C50H54O3S
11-Cyclohexyl-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-methylsulfanylspiro[6-oxapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(14),2(7),3,8,10,12,15,17,19-nonaene-21,3'-cyclohexane]
—— 3,7-Dibenzyloxy-5,8,4'-trimethoxy-flavon 5928-10-9 C32H28O7
3,7-Dibenzyloxy-5,8,4'-trimethoxy-flavon
—— 5-(4-chlorophenyl)-7-methyl-2-(naphthalen-2-yl)-6-[(E)-3-(naphthalen-2-yl)acryloyl]chroman-4-one 1365935-68-7 C39H27ClO3
5-(4-chlorophenyl)-7-methyl-2-(naphthalen-2-yl)-6-[(E)-3-(naphthalen-2-yl)acryloyl]chroman-4-one
—— 2-methyl-6,6,11-triphenyl-6,6a-dihydro-indeno[1,2-c]chromene 858504-21-9 C35H26O
2-methyl-6,6,11-triphenyl-6,6a-dihydro-indeno[1,2-c]chromene
—— 2-(4-methoxyphenyl)-3-methoxy-6-propionylchromone 141070-45-3 C20H18O5
2-(4-methoxyphenyl)-3-methoxy-6-propionylchromone
—— 2,7-dihydro-7-methyl-2,2-diphenylpyrano[3,2-c]carbazole 355408-52-5 C28H21NO
2,7-dihydro-7-methyl-2,2-diphenylpyrano[3,2-c]carbazole
—— (+)-gallocatechin-(4α->2)-phloroglucinol 68930-51-8 C21H18O10
(+)-gallocatechin-(4α->2)-phloroglucinol
—— 4'-methyl-5,7,8-trimethoxyflav-3-ene 1334121-19-5 C19H20O4
4'-methyl-5,7,8-trimethoxyflav-3-ene
—— 8-[6-(2,4-Dimethoxy-benzoyl)-5-(2,4-dimethoxy-phenyl)-3-methyl-cyclohex-2-enyl]-2-(2,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-3-(3-methyl-but-2-enyl)-chromen-4-one 75629-24-2 C47H50O11
8-[6-(2,4-Dimethoxy-benzoyl)-5-(2,4-dimethoxy-phenyl)-3-methyl-cyclohex-2-enyl]-2-(2,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-3-(3-methyl-but-2-enyl)-chromen-4-one
—— 5,7-dimethoxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 1128053-53-1 C26H29NO7
5,7-dimethoxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
—— [5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] thiophene-2-carboxylate 1416850-01-5 C20H14O6S
[5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] thiophene-2-carboxylate
—— ethyl 4-(4-ethylphenyl)spiro[2H-1-benzopyran-2,4'-piperidine]-1'-acetate 340267-48-3 C25H29NO3
ethyl 4-(4-ethylphenyl)spiro[2H-1-benzopyran-2,4'-piperidine]-1'-acetate
—— (E)-3-(p-methylbenzylidene)-2-p-tolylchroman-4-one 1427276-89-8 C24H20O2
(E)-3-(p-methylbenzylidene)-2-p-tolylchroman-4-one
—— 4-(7-tert-Butyl-4-oxo-4H-chromen-2-yl)-benzoic acid methyl ester 113027-10-4 C21H20O4
4-(7-tert-Butyl-4-oxo-4H-chromen-2-yl)-benzoic acid methyl ester
—— CRM 361343-83-1 C37H32O6
CRM
—— 2-(4-Methoxy-phenyl)-4-thiophen-2-yl-4H-chromene 111862-05-6 C20H16O2S
2-(4-Methoxy-phenyl)-4-thiophen-2-yl-4H-chromene
—— 7-Butyloxy-3.2'.5'-trihydroxy-flavon 94303-29-4 C19H18O6
7-Butyloxy-3.2'.5'-trihydroxy-flavon
—— 1-methyl-5-phenyl-2-oxa-3,4-benzobicyclo<3.2.0>heptan-7-one 99477-37-9 C17H14O2
1-methyl-5-phenyl-2-oxa-3,4-benzobicyclo<3.2.0>heptan-7-one
—— 7,8-Dihydroxy-3',4',5'-trimethoxy-3-methylflavon 65894-05-5 C19H18O7
7,8-Dihydroxy-3',4',5'-trimethoxy-3-methylflavon
—— 3'-Chloro-3-hydroxy-2-methoxyflavanone 136764-63-1 C16H13ClO4
3'-Chloro-3-hydroxy-2-methoxyflavanone
—— 4-((2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)butyl nitrate 1443679-18-2 C32H25NO9
4-((2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)butyl nitrate
—— 7-hydroxyethyloxy-3',4',5,6-tetramethoxy flavone 203191-37-1 C21H22O8
7-hydroxyethyloxy-3',4',5,6-tetramethoxy flavone
—— 8,18-Dimethoxy-13,13-bis(4-methoxyphenyl)-18-methyl-6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene 1259401-30-3 C39H34O6
8,18-Dimethoxy-13,13-bis(4-methoxyphenyl)-18-methyl-6,12-dioxahexacyclo[15.7.0.02,10.03,7.011,16.019,24]tetracosa-1(17),2,7,9,11(16),14,19,21,23-nonaene
—— 1062237-65-3 C26H15ClO3
—— Cirsitakaosid-acetat 67884-13-3 C33H34O16
Cirsitakaosid-acetat
—— 6-C-Prenylacacetindiacetat 68634-25-3 C25H24O7
6-C-Prenylacacetindiacetat
—— 7-(2,2-dimethyl-1,3-dioxol-4-ylmethoxy)-5-hydroxy-2-(3-ethoxycarbonyl-methoxy-4-methoxy-2-propylphenyl)-4H-1-benzopyran-4-one 198886-28-1 C29H32O10
7-(2,2-dimethyl-1,3-dioxol-4-ylmethoxy)-5-hydroxy-2-(3-ethoxycarbonyl-methoxy-4-methoxy-2-propylphenyl)-4H-1-benzopyran-4-one
—— 6-chloro-3-methoxymethoxy-2-(3',4',5'-trimethoxyphenyl)-4-oxo-4H-1-benzopyran 1250865-52-1 C20H19ClO7
6-chloro-3-methoxymethoxy-2-(3',4',5'-trimethoxyphenyl)-4-oxo-4H-1-benzopyran