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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-allyl-2-(3,4-diacetoxyphenyl)-5-hydroxy-4-oxo-4H-chromene-3,7-diyl diacetate 1000841-76-8 C26H22O11
6-allyl-2-(3,4-diacetoxyphenyl)-5-hydroxy-4-oxo-4H-chromene-3,7-diyl diacetate
—— (2R,3S)-trans-3-acetoxy-3',4'-methylenedioxyflavan 1196870-63-9 C18H16O5
(2R,3S)-trans-3-acetoxy-3',4'-methylenedioxyflavan
—— hesperetin (2-hydroxybenzoyl)hydrazone 1261060-91-6 C23H20N2O7
hesperetin (2-hydroxybenzoyl)hydrazone
—— 1178862-93-5 C21H18O11*C42H70O35
—— (2S)-5,7,5'-trihydroxyflavanone 2'-O-β-D-2,6-O-diacetylglucopyranosyl-(1->3)-α-L-2-O-acetylrhamnopyranoside 917563-38-3 C33H38O18
(2S)-5,7,5'-trihydroxyflavanone 2'-O-β-D-2,6-O-diacetylglucopyranosyl-(1->3)-α-L-2-O-acetylrhamnopyranoside
—— 7,8-dimethoxy-2-(4-methoxy-3-methoxymethoxy-phenyl)-chroman-4-one 111797-38-7 C20H22O7
7,8-dimethoxy-2-(4-methoxy-3-methoxymethoxy-phenyl)-chroman-4-one
—— (2R,3S)-3-((R)-2-Methoxy-2-phenyl-ethyl)-2-phenyl-chroman-4-one 39953-78-1 C24H22O3
(2R,3S)-3-((R)-2-Methoxy-2-phenyl-ethyl)-2-phenyl-chroman-4-one
—— 10-(2,4-Dimethoxyphenyl)-11-methoxy-5,5-bis(4-methoxyphenyl)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] 1278524-05-2 C48H44O6
10-(2,4-Dimethoxyphenyl)-11-methoxy-5,5-bis(4-methoxyphenyl)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]
—— 6-acetoxy-7-hydroxyflavon-8-amino-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 1374218-57-1 C30H29NO15
6-acetoxy-7-hydroxyflavon-8-amino-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester)
—— 2-(4-methylphenyl)-2,3-dihydrobenzo[h]chromen-4-one 108001-37-2 C20H16O2
2-(4-methylphenyl)-2,3-dihydrobenzo[h]chromen-4-one
—— 2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3-benzyloxy-5-hydroxyl-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 1313191-77-3 C49H42O16
2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3-benzyloxy-5-hydroxyl-7-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one
—— 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 1610737-87-5 C22H16O9S
2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate
—— 2-bromo-3-methyl-7-phenyl-furo[2,3-f]chromen-9-one 858249-82-8 C18H11BrO3
2-bromo-3-methyl-7-phenyl-furo[2,3-f]chromen-9-one
—— [(2R,3R,4R,5S)-3,4-diacetyloxy-5-[5-acetyloxy-2-(4-acetyloxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxyoxolan-2-yl]methyl acetate 1374991-33-9 C30H28O15
[(2R,3R,4R,5S)-3,4-diacetyloxy-5-[5-acetyloxy-2-(4-acetyloxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxyoxolan-2-yl]methyl acetate
—— 2,2,2-trifluoro-N-(1-methyl-1H-benzo[d]imidazol-2-yl)-N-(4'-oxo-2-phenylspiro[chromane-4,2'-thiazolidin]-3'-yl)acetamide 1338825-03-8 C27H21F3N4O3S
2,2,2-trifluoro-N-(1-methyl-1H-benzo[d]imidazol-2-yl)-N-(4'-oxo-2-phenylspiro[chromane-4,2'-thiazolidin]-3'-yl)acetamide
—— Hexahydrosophoranon 27743-57-3 C30H42O4
Hexahydrosophoranon
—— Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-{5-acetoxy-2-[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]-4-oxo-chroman-7-yloxy}-2-acetoxymethyl-5-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 39953-47-4 C47H56O22
Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-6-{5-acetoxy-2-[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]-4-oxo-chroman-7-yloxy}-2-acetoxymethyl-5-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
—— 7-amino-2-(3,4-dimethoxy-phenyl)-3-methoxy-chromen-4-one 27500-25-0 C18H17NO5
7-amino-2-(3,4-dimethoxy-phenyl)-3-methoxy-chromen-4-one
—— 3-cyanothioflavone 94953-60-3 C16H9NO2S
3-cyanothioflavone
—— 7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetrahydrobenzo[b]oxepine 1449790-32-2 C20H24O5
7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetrahydrobenzo[b]oxepine
—— 1105512-42-2 C15H10O4*C42H70O35
—— 3',5-dihydroxy-4'-methoxy-7-<<N-(carbobenzyloxy)amino>propoxy>flavanone 76799-54-7 C27H27NO8
3',5-dihydroxy-4'-methoxy-7-<<N-(carbobenzyloxy)amino>propoxy>flavanone
—— 7-chloro-3-methyl-2-phenyl-1,4-dioxa-cyclopenta-[b]naphthalene-9-one 1135839-08-5 C18H11ClO3
7-chloro-3-methyl-2-phenyl-1,4-dioxa-cyclopenta-[b]naphthalene-9-one
—— Fisetinidol-(4α,8)-epicatechin hepta-O-methyl ether diacetate 78185-33-8 C41H44O13
Fisetinidol-(4α,8)-epicatechin hepta-O-methyl ether diacetate
—— (2-(Benzyloxy)-5-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy)methyl acetate 1114367-04-2 C39H32O9
(2-(Benzyloxy)-5-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy)methyl acetate
—— (-)-epigallocatechin gallate complex with β-cyclodextrin 133055-81-9 C22H18O11*C42H70O35
(-)-epigallocatechin gallate complex with β-cyclodextrin
—— 5-methylcarbamoyloxy-3(3,4-dimethoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran 143099-03-0 C29H24FNO5
5-methylcarbamoyloxy-3(3,4-dimethoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran
—— rhamnocitrin 3-O-glucoside 41545-37-3 C22H22O11
rhamnocitrin 3-O-glucoside
—— 2-(2,4-dichloroquinolin-6-yl)-4H-1-benzopyran-4-one 1010857-13-2 C18H9Cl2NO2
2-(2,4-dichloroquinolin-6-yl)-4H-1-benzopyran-4-one
—— 2,3-dihydroquercetin 7-dipiperidylthionophosphate 1153630-33-1 C25H31N2O7PS
2,3-dihydroquercetin 7-dipiperidylthionophosphate
—— 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-[tetra-O-acetyl-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one 357194-11-7 C42H36O16
2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-[tetra-O-acetyl-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one
—— 8-methyl-N-naphthalen-1-yl-7-oxo-10-phenyl-7a,8,9,10-tetrahydronaphtho[1,2-b]chromene-9-carboxamide 135978-98-2 C35H27NO3
8-methyl-N-naphthalen-1-yl-7-oxo-10-phenyl-7a,8,9,10-tetrahydronaphtho[1,2-b]chromene-9-carboxamide
—— 3,7-dimethoxy-3'-chloroflavone 1385652-20-9 C17H13ClO4
3,7-dimethoxy-3'-chloroflavone
—— (2S,3S)-cis-3-acetoxy-3',4'-dimethoxyflavan 1196870-55-9 C19H20O5
(2S,3S)-cis-3-acetoxy-3',4'-dimethoxyflavan
—— 6-amino-2-(4-fluorophenyl)-3-hydroxy-4H-chromen-4-one hydrochloride 1252653-02-3 C15H10FNO3*ClH
6-amino-2-(4-fluorophenyl)-3-hydroxy-4H-chromen-4-one hydrochloride
—— cis-2'-Hydroxy-4-methyl-2,4-diethylflavan 112307-57-0 C20H24O2
cis-2'-Hydroxy-4-methyl-2,4-diethylflavan
—— 2-morpholin-4-ylethyl 2-(4-oxo-2-phenylchromen-8-yl)acetate;hydrochloride 87626-59-3 C23H23NO5*ClH
2-morpholin-4-ylethyl 2-(4-oxo-2-phenylchromen-8-yl)acetate;hydrochloride
—— astragalin 70324-47-9 C22H22O11
astragalin
—— 2-(2,3-dihydroxyphenyl)-6-methoxychroman-4-one 1628164-41-9 C16H14O5
2-(2,3-dihydroxyphenyl)-6-methoxychroman-4-one
—— 8-Brom-7-hydroxy-flavon 3428-16-8 C15H9BrO3
8-Brom-7-hydroxy-flavon
—— 5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-methylsulfanyl-10-phenylsulfanylspiro[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] 1263317-99-2 C50H48O3S2
5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-methylsulfanyl-10-phenylsulfanylspiro[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]
—— (2R<sup>*</sup>,3R<sup>*</sup>)-3,5,4'-triacetoxyflavanone 101946-92-3 C21H18O8
(2R<sup>*</sup>,3R<sup>*</sup>)-3,5,4'-triacetoxyflavanone
—— exo-6,6a-trans-6-ethoxy-6,7-bis(p-methoxyphenyl)-6a,7,13,13a-tetrahydro-6H-7,13-methano<1>benzopyrano<3,4-c><1>benzoxepin 95082-59-0 C34H32O5
exo-6,6a-trans-6-ethoxy-6,7-bis(p-methoxyphenyl)-6a,7,13,13a-tetrahydro-6H-7,13-methano<1>benzopyrano<3,4-c><1>benzoxepin
—— 4-oxo-2-(2,3,4-triacetoxyphenyl)-4H-chromene-3,5,7-triyl triacetate 1569852-42-1 C27H22O14
4-oxo-2-(2,3,4-triacetoxyphenyl)-4H-chromene-3,5,7-triyl triacetate
—— 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one 357194-04-8 C34H28O12
2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-(β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one
—— 2-phenylchroman-4-one (4-nitrophenyl)hydrazone 16281-64-4 C21H17N3O3
2-phenylchroman-4-one (4-nitrophenyl)hydrazone
—— 2-phenyl-2H-chromen-4-yl dimethylcarbamate 1573114-70-1 C18H17NO3
2-phenyl-2H-chromen-4-yl dimethylcarbamate
—— 2-(4-Methoxy-phenyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one 128815-01-0 C17H16O3
2-(4-Methoxy-phenyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one
—— 3-(3-hydroxyphenyl)-4-methyl-2-(4-((R)-2-(pyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol trifluoroacetate 1352306-84-3 C2HF3O2*C29H31NO4
3-(3-hydroxyphenyl)-4-methyl-2-(4-((R)-2-(pyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol trifluoroacetate
—— 2-(3-nitro-phenyl)-chroman-3,4-dione-3-oxime 107918-44-5 C15H10N2O5
2-(3-nitro-phenyl)-chroman-3,4-dione-3-oxime