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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
—— 6-(p-tolyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene 1415606-25-5 C17H16O3
6-(p-tolyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene
—— 2-Diethylamino-N-(3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)-acetamide 56822-88-9 C22H24N2O3
2-Diethylamino-N-(3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)-acetamide
—— 3-Ethoxy-5-hydroxy-7,4'-dimethoxyflavon 58264-79-2 C19H18O6
3-Ethoxy-5-hydroxy-7,4'-dimethoxyflavon
—— methyl 6-hydroxy-2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5-carboxylate 1558797-62-8 C21H18O4
methyl 6-hydroxy-2-phenyl-3,4-dihydro-2H-benzo[h]chromene-5-carboxylate
—— (+)-balsacone F 1572949-08-6 C25H24O6
(+)-balsacone F
—— 8-(3-Acetoxy-3-methyl-2-oxo-1-butyl)-7-hydroxy-5-methoxyflavon 91360-64-4 C23H22O7
8-(3-Acetoxy-3-methyl-2-oxo-1-butyl)-7-hydroxy-5-methoxyflavon
—— 2-(2,3-bis-benzyloxy-4-methoxy-phenyl)-5-hydroxy-3,7-dimethoxy-chromen-4-one 56128-64-4 C32H28O8
2-(2,3-bis-benzyloxy-4-methoxy-phenyl)-5-hydroxy-3,7-dimethoxy-chromen-4-one
—— methyl 7-fluoro-4-oxo-2-p-tolyl-4H-chromene-3-carboxylate 1439357-09-1 C18H13FO4
methyl 7-fluoro-4-oxo-2-p-tolyl-4H-chromene-3-carboxylate
—— (2S,3R,4S,5S,6R)-2-[[11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-[(1E,3E)-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]-2-oxa-8-oxoniatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,8,10-hexaen-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 1290536-73-0 C37H37O15
(2S,3R,4S,5S,6R)-2-[[11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-[(1E,3E)-4-(4-hydroxy-3,5-dimethoxyphenyl)buta-1,3-dienyl]-2-oxa-8-oxoniatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,8,10-hexaen-4-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— 7,11-Dioxo-8,10-diphenyl-7,11-dihydro-phenanthro<2.3-c>furan 104978-89-4 C28H16O3
7,11-Dioxo-8,10-diphenyl-7,11-dihydro-phenanthro<2.3-c>furan
—— 6,8-Dichlor-5-hydroxy-flavon 92429-30-6 C15H8Cl2O3
6,8-Dichlor-5-hydroxy-flavon
—— 10-Methoxy-5,5-bis(4-methoxyphenyl)-22,22-dimethylspiro[6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8(13),9,11,15,17,19-nonaene-21,1'-cyclohexane] 945425-04-7 C43H42O4
10-Methoxy-5,5-bis(4-methoxyphenyl)-22,22-dimethylspiro[6-oxapentacyclo[12.8.0.02,7.08,13.015,20]docosa-1(14),2(7),3,8(13),9,11,15,17,19-nonaene-21,1'-cyclohexane]
—— 4-[4-(1',1',2',2'-Tetramethyl-14-phenylspiro[5,8,13-trioxaheptacyclo[16.13.0.02,11.04,9.012,17.020,25.026,31]hentriaconta-1(18),2,4(9),10,12(17),15,20,22,24,26,28,30-dodecaene-19,4'-cyclopentane]-14-yl)phenyl]morpholine 1132661-65-4 C52H49NO4
4-[4-(1',1',2',2'-Tetramethyl-14-phenylspiro[5,8,13-trioxaheptacyclo[16.13.0.02,11.04,9.012,17.020,25.026,31]hentriaconta-1(18),2,4(9),10,12(17),15,20,22,24,26,28,30-dodecaene-19,4'-cyclopentane]-14-yl)phenyl]morpholine
—— 2-benzo[1,3]dioxol-5-yl-6-nitro-benzo[h]chromen-4-one 111531-44-3 C20H11NO6
2-benzo[1,3]dioxol-5-yl-6-nitro-benzo[h]chromen-4-one
—— Acetic acid (2R,3S,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 61284-11-5 C44H50O23
Acetic acid (2R,3S,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
—— 1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-(2-benzimidazolylmethyl)-1,4,10,13-tetraoxa-7-azatridecane 1346227-56-2 C46H41N3O8
1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-(2-benzimidazolylmethyl)-1,4,10,13-tetraoxa-7-azatridecane
—— 10-ethoxy-7-(3-nitrophenyl)-6-phenyl-6a,7-dihydro-6H-benzo[b]chromeno[4,3-e][1,4]thiazepine 1514898-65-7 C30H24N2O4S
10-ethoxy-7-(3-nitrophenyl)-6-phenyl-6a,7-dihydro-6H-benzo[b]chromeno[4,3-e][1,4]thiazepine
—— 5,6-diacetoxy-3,4',7-trimethoxyflavone 154047-82-2 C22H20O9
5,6-diacetoxy-3,4',7-trimethoxyflavone
—— 7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)flavanone 89840-30-2 C30H24O5
7-(2,3-trans-3,4-cis-3-hydroxyflavan-4-yloxy)flavanone
—— 1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-(4-tert-butyloxycarbonylaminobenzyl)-1,4,10,13-tetraoxa-7-azatridecane 1346227-50-6 C50H50N2O10
1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-(4-tert-butyloxycarbonylaminobenzyl)-1,4,10,13-tetraoxa-7-azatridecane
—— N-(6,8-difluoro-2-(3-fluoro-4-pivalamidophenyl)-7-((N-formylformamido)methyl)-4-oxo-4H-chromen-5-yl)pivalamide 207285-73-2 C28H28F3N3O6
N-(6,8-difluoro-2-(3-fluoro-4-pivalamidophenyl)-7-((N-formylformamido)methyl)-4-oxo-4H-chromen-5-yl)pivalamide
—— cis-4-amino-6-methylflavan 104819-72-9 C16H17NO
cis-4-amino-6-methylflavan
—— 7,4'-Dibenzyloxy-5,6,3'-triacetoxy-flavon 27181-99-3 C35H28O10
7,4'-Dibenzyloxy-5,6,3'-triacetoxy-flavon
—— Neohesperidin 13241-33-3 C28H34O15
Neohesperidin
—— 2-(3-((E)-4-methoxystyryl)phenyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one 1251022-82-8 C26H24O5
2-(3-((E)-4-methoxystyryl)phenyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one
—— Acetic acid (2R,3S,4R)-2-(3,4-dimethoxy-phenyl)-4-hydroxy-7-methoxy-chroman-3-yl ester 29799-49-3 C20H22O7
Acetic acid (2R,3S,4R)-2-(3,4-dimethoxy-phenyl)-4-hydroxy-7-methoxy-chroman-3-yl ester
—— 1-{3-[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-8-yl]-2-hydroxy-4,6-dimethoxy-phenyl}-3-(4-methoxy-phenyl)-propane-1,3-dione 37879-31-5 C36H32O11
1-{3-[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-8-yl]-2-hydroxy-4,6-dimethoxy-phenyl}-3-(4-methoxy-phenyl)-propane-1,3-dione
—— 3-7''-Biflavonyloxymethan 55091-78-6 C31H20O6
3-7''-Biflavonyloxymethan
—— 5-[(2'-phenyl-4'H-4'-oxo-1'-benzopyran-6'-yl)methylenyl]-2-thiohydantoine 1043023-97-7 C19H12N2O3S
5-[(2'-phenyl-4'H-4'-oxo-1'-benzopyran-6'-yl)methylenyl]-2-thiohydantoine
—— 7-(oxiran-2-ylmethoxy)-2-phenylchroman-4-one 136397-09-6 C18H16O4
7-(oxiran-2-ylmethoxy)-2-phenylchroman-4-one
—— 1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-[5-(6-chloropiperonyl)]-1,4,10,13-tetraoxa-7-azatridecane 1346227-38-0 C46H40ClNO10
1,13-bis[4'-(4H-chromen-4-on-2-yl)phenyl]-7-[5-(6-chloropiperonyl)]-1,4,10,13-tetraoxa-7-azatridecane
—— Melinervin-triacetat 52041-20-0 C24H20O12
Melinervin-triacetat
—— 13-Butyl-18-[4-(2,6-dimethylpiperidin-1-yl)phenyl]-23-methoxy-18-phenyl-19-oxa-9-thiahexacyclo[12.12.0.02,7.08,12.015,20.021,26]hexacosa-1(14),2,4,6,8(12),10,15(20),16,21(26),22,24-undecaen-13-ol 1008782-23-7 C48H47NO3S
13-Butyl-18-[4-(2,6-dimethylpiperidin-1-yl)phenyl]-23-methoxy-18-phenyl-19-oxa-9-thiahexacyclo[12.12.0.02,7.08,12.015,20.021,26]hexacosa-1(14),2,4,6,8(12),10,15(20),16,21(26),22,24-undecaen-13-ol
—— 3,4-diacetoxy-2'-hydroxy-4'-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans(?)-chalcone 123839-02-1 C33H34O16
3,4-diacetoxy-2'-hydroxy-4'-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans(?)-chalcone
—— (E)-(6-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3-(3-chloro-4-hydroxyphenyl)acrylate 1257529-63-7 C30H25ClO13
(E)-(6-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3-(3-chloro-4-hydroxyphenyl)acrylate
—— (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-yl 3''-benzyloxy-4'',5''-dimethoxybenzoate 901125-43-7 C60H54O11
(-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',5'-bis(benzyloxy)-4'-methoxyphenyl]chroman-3-yl 3''-benzyloxy-4'',5''-dimethoxybenzoate
—— 5-methoxy-2-(4-methoxy-phenyl)-8,8-dimethyl-10-(3-methyl-but-2-enyl)-2,3-dihydro-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one 55730-70-6 C27H30O5
5-methoxy-2-(4-methoxy-phenyl)-8,8-dimethyl-10-(3-methyl-but-2-enyl)-2,3-dihydro-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-4-one
—— 6-Methoxy-2-(4-methoxy-phenyl)-3-oxo-2,3-dihydro-benzofuran-2-carboxylic acid allyl ester 132835-30-4 C20H18O6
6-Methoxy-2-(4-methoxy-phenyl)-3-oxo-2,3-dihydro-benzofuran-2-carboxylic acid allyl ester
—— cis-4-N-methylaminoflavan 104819-76-3 C16H17NO
cis-4-N-methylaminoflavan
—— 5-Methoxy-8,8-dimethyl-6-(2-methyl-butyryl)-4-phenyl-3,4,9,10-tetrahydro-8H-pyrano[2,3-f]chromen-2-one 88640-47-5 C26H30O5
5-Methoxy-8,8-dimethyl-6-(2-methyl-butyryl)-4-phenyl-3,4,9,10-tetrahydro-8H-pyrano[2,3-f]chromen-2-one
—— 24,25-Dimethoxy-19,19-bis(4-methoxyphenyl)-1',1',2',2'-tetramethylspiro[20-oxahexacyclo[13.12.0.02,7.08,13.016,21.022,27]heptacosa-1(15),2,4,6,8,10,12,16(21),17,22,24,26-dodecaene-14,4'-cyclopentane] 1008782-38-4 C50H48O5
24,25-Dimethoxy-19,19-bis(4-methoxyphenyl)-1',1',2',2'-tetramethylspiro[20-oxahexacyclo[13.12.0.02,7.08,13.016,21.022,27]heptacosa-1(15),2,4,6,8,10,12,16(21),17,22,24,26-dodecaene-14,4'-cyclopentane]
—— 4-Methoxy-7-(4-methoxyphenyl)-[1,3]dioxolo[4,5-f]chromen-9-one 1456770-94-7 C18H14O6
4-Methoxy-7-(4-methoxyphenyl)-[1,3]dioxolo[4,5-f]chromen-9-one
—— apigenin 6-C-β-glucopyranoside-8-C-α-arabinopyranoside 121477-68-7 C26H28O16
apigenin 6-C-β-glucopyranoside-8-C-α-arabinopyranoside
—— Potassium; (Z)-2-cyano-1-ethoxy-2-[7-methoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl]-ethenolate 80964-96-1 C22H18NO6*K
Potassium; (Z)-2-cyano-1-ethoxy-2-[7-methoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl]-ethenolate
—— Acetic acid (2R,3R,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 61284-18-2 C46H54O24
Acetic acid (2R,3R,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-Diethylamino-N-(3-methyl-4-oxo-2-phenyl-4H-chromen-6-yl)-acetamide 56822-66-3 C22H24N2O3
2-Diethylamino-N-(3-methyl-4-oxo-2-phenyl-4H-chromen-6-yl)-acetamide
—— 3,7-Di-O-Methylgalangin 40603-71-2 C22H22O5
3,7-Di-O-Methylgalangin
—— cis-2-(Diphenylhydroxymethyl)-4-flavanol 63483-26-1 C28H24O3
cis-2-(Diphenylhydroxymethyl)-4-flavanol
—— 1169683-95-7 C130H159BN4O8Zn
—— 4-bromo-6-methoxy-2-phenyl-2H-chromene 131942-11-5 C16H13BrO2
4-bromo-6-methoxy-2-phenyl-2H-chromene