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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
—— permethyl 4''-O-β-D-glucopyranosyl-6-C-β-D-glucopyranosylacacetin 67549-79-5 C37H50O15
permethyl 4''-O-β-D-glucopyranosyl-6-C-β-D-glucopyranosylacacetin
—— 7-Diethylcarbamoylmethoxy-4-oxo-2-phenyl-4H-chromen 100030-11-3 C21H21NO4
7-Diethylcarbamoylmethoxy-4-oxo-2-phenyl-4H-chromen
—— Isomelacacidin-4-p-tolylsulfon-7,8,3',4'-tetramethylaether 120640-49-5 C26H28O8S
Isomelacacidin-4-p-tolylsulfon-7,8,3',4'-tetramethylaether
—— 6-(4-chlorophenyl)-7-imino-10-methyl-6a-nitro-9-phenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 1248412-53-4 C27H20ClN3O3
6-(4-chlorophenyl)-7-imino-10-methyl-6a-nitro-9-phenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile
—— 7-Isopropyloxy-3-methyl-8-chlormethyl-flavon 102237-38-7 C20H19ClO3
7-Isopropyloxy-3-methyl-8-chlormethyl-flavon
—— 6-acetylamino-2-benzo[1,3]dioxol-5-yl-7-methoxy-chroman-4-one 113060-89-2 C19H17NO6
6-acetylamino-2-benzo[1,3]dioxol-5-yl-7-methoxy-chroman-4-one
—— (1-methoxy-6-phenyl-6H-dibenzo(b,d)pyran-8-yl)-(2-methoxy)acetamide 373621-52-4 C23H21NO4
(1-methoxy-6-phenyl-6H-dibenzo(b,d)pyran-8-yl)-(2-methoxy)acetamide
—— 7-acetoxy-2-(2,3-diacetoxy-phenyl)-chromen-4-one 110144-72-4 C21H16O8
7-acetoxy-2-(2,3-diacetoxy-phenyl)-chromen-4-one
—— 4-(4-hydroxy-phenyl)-2-propyl-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol 787622-71-3 C21H24O3
4-(4-hydroxy-phenyl)-2-propyl-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol
—— 5-Hydroxy-7-methoxy-6-allyl-flavon 94305-78-9 C19H16O4
5-Hydroxy-7-methoxy-6-allyl-flavon
—— 8-Methoxy-5-allyloxy-flavon 94305-83-6 C19H16O4
8-Methoxy-5-allyloxy-flavon
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate 217661-69-3 C41H45O21
[(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate
—— 2-(4-((S)-2-((R)-3-fluoropyrrolidin-1-yl)propoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol 1352307-86-8 C29H30FNO4
2-(4-((S)-2-((R)-3-fluoropyrrolidin-1-yl)propoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol
—— 4-[2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-4-oxo-4H-chromen-8-yl]-1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyridinium bromide 372103-59-8 Br*C33H26ClN2O6
4-[2-(3-chloro-4-methoxyphenyl)-3-methoxy-6-methyl-4-oxo-4H-chromen-8-yl]-1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]pyridinium bromide
—— 7-hydroxy-2-(4-methoxy-phenyl)-8-nitro-chromen-4-one 132318-72-0 C16H11NO6
7-hydroxy-2-(4-methoxy-phenyl)-8-nitro-chromen-4-one
—— 7-glucotrifolin 198219-16-8 C27H30O16
7-glucotrifolin
—— 4-amino-5,8-dihydroxy-2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin 114499-14-8 C16H17NO3
4-amino-5,8-dihydroxy-2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin
—— 7-O-(+)-peltogynol-β-D-glucopyranoside 1254041-12-7 C22H24O11
7-O-(+)-peltogynol-β-D-glucopyranoside
—— 2-[4-(3-chloropropoxy)-phenyl]-4,7-dihydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran 361391-06-2 C25H22ClF3O5
2-[4-(3-chloropropoxy)-phenyl]-4,7-dihydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran
—— 2-(4'-fluorophenyl)-3-(2-thiaoctadecyl)-5,7-bisacetoxy-4H-1-benzopyran-4-one 138077-00-6 C36H47FO6S
2-(4'-fluorophenyl)-3-(2-thiaoctadecyl)-5,7-bisacetoxy-4H-1-benzopyran-4-one
—— 7-butoxy-2-phenyl-4H-chromen-4-one 59880-36-3 C19H18O3
7-butoxy-2-phenyl-4H-chromen-4-one
—— 2-phenyl-3-(phenylselanyl)-4H-chromen-4-one 1332697-92-3 C21H14O2Se
2-phenyl-3-(phenylselanyl)-4H-chromen-4-one
—— 3-(allyloxy)-5-methoxy-2-phenyl-4H-chromen-4-one 1233689-15-0 C19H16O4
3-(allyloxy)-5-methoxy-2-phenyl-4H-chromen-4-one
—— 7-methoxy-2-(4-bromophenyl)-3-nitro-2H-chromene 1227402-07-4 C16H12BrNO4
7-methoxy-2-(4-bromophenyl)-3-nitro-2H-chromene
—— 8-((3-((tert-butyldimethylsilyl)oxy)propyl)amino)-6-chloro-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one 1621457-92-8 C25H31ClN2O6Si
8-((3-((tert-butyldimethylsilyl)oxy)propyl)amino)-6-chloro-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one
—— [(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3-methoxyphenyl)prop-2-enoate 217661-67-1 C42H47O22
[(2R,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3-methoxyphenyl)prop-2-enoate
—— 7,4'-dimethoxymethyl-8-geranylapigenin 134955-39-8 C29H34O7
7,4'-dimethoxymethyl-8-geranylapigenin
—— Acetic acid 9,10-dimethoxy-6-(4-methoxy-phenyl)-11-oxo-6H,11H-5,12-dioxa-chrysen-7-yl ester 74700-71-3 C27H22O8
Acetic acid 9,10-dimethoxy-6-(4-methoxy-phenyl)-11-oxo-6H,11H-5,12-dioxa-chrysen-7-yl ester
—— (R)-3-(4-fluorophenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol 1352307-43-7 C30H32FNO3
(R)-3-(4-fluorophenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol
—— Acetylderivat von 6-Nitro-3'-hydroxy-flavonol 109469-05-8 C19H13NO8
Acetylderivat von 6-Nitro-3'-hydroxy-flavonol
—— 3,7,8-trimethoxyflavone 94393-13-2 C18H16O5
3,7,8-trimethoxyflavone
—— (+/-)-2'-<(α-Methoxy-isopropyloxy)-methyl>-4',5',7-trimethoxy-cis-3,4-isopropylidendioxy-trans-2,3-flavan 102324-06-1 C26H34O8
(+/-)-2'-<(α-Methoxy-isopropyloxy)-methyl>-4',5',7-trimethoxy-cis-3,4-isopropylidendioxy-trans-2,3-flavan
—— 8-Brom-5,7,3',4'-tetramethoxy-3-piperonyliden-flavanon 96179-26-9 C27H23BrO8
8-Brom-5,7,3',4'-tetramethoxy-3-piperonyliden-flavanon
—— (1R,6R,7R,13S,21R)-7,13-bis(3,4-dimethoxyphenyl)-3,17,19-trimethoxy-8,12,14-trioxapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2(11),3,9,15(20),16,18-hexaene-6,21-diol 114569-26-5 C37H38O12
(1R,6R,7R,13S,21R)-7,13-bis(3,4-dimethoxyphenyl)-3,17,19-trimethoxy-8,12,14-trioxapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2(11),3,9,15(20),16,18-hexaene-6,21-diol
—— 5,7,3'-trihydroxy-3,8,4'-trimethoxyflavone 20921-19-1 C18H16O8
5,7,3'-trihydroxy-3,8,4'-trimethoxyflavone
—— 3-(benzyloxy)-2-[4(benzyloxy)-3-methylphenyl]-6-methyl-8-nitro-4H-chromen-4-one 372102-68-6 C31H25NO6
3-(benzyloxy)-2-[4(benzyloxy)-3-methylphenyl]-6-methyl-8-nitro-4H-chromen-4-one
—— 2'-Methoxy-3-methyl-7-acetoxyflavon 56595-67-6 C19H16O5
2'-Methoxy-3-methyl-7-acetoxyflavon
—— 7-β-D-glucopyranosyloxy-5-methoxy-2-phenyl-chromen-4-one 72963-83-8 C22H22O9
7-β-D-glucopyranosyloxy-5-methoxy-2-phenyl-chromen-4-one
—— 2-(3,5-difluorophenyl)chroman-6-ol 488847-97-8 C15H12F2O2
2-(3,5-difluorophenyl)chroman-6-ol
—— 6-hydroxy-2-(4-chlorophenyl)chroman-4-one 488849-41-8 C15H11ClO3
6-hydroxy-2-(4-chlorophenyl)chroman-4-one
—— (2S,3R,4R,5R,6S)-2-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yloxy)-4-hydroxy-6-propyltetrahydro-2H-pyran-3,5-diyl diacetate 1417412-09-9 C48H46O12
(2S,3R,4R,5R,6S)-2-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yloxy)-4-hydroxy-6-propyltetrahydro-2H-pyran-3,5-diyl diacetate
—— 3,6-Dimethoxy-flavon-2'-carbonsaeure 98281-77-7 C18H14O6
3,6-Dimethoxy-flavon-2'-carbonsaeure
—— 2-<3,4-Dimethoxy-phenyl>-6-benzoyl-chromon 102665-09-8 C24H18O5
2-<3,4-Dimethoxy-phenyl>-6-benzoyl-chromon
—— 3-Brom-5,7-dimethoxy-flavanon 108979-11-9 C17H15BrO4
3-Brom-5,7-dimethoxy-flavanon
—— 6-Nitro-3'-chlor-4'-methoxy-flavon 101081-48-5 C16H10ClNO5
6-Nitro-3'-chlor-4'-methoxy-flavon
—— 6-Fluor-8-chlor-4'-methoxy-flavon 1682-91-3 C16H10ClFO3
6-Fluor-8-chlor-4'-methoxy-flavon
—— 8-Butyryl-2-(4-chloro-phenyl)-6-methyl-chromen-4-one 213622-38-9 C20H17ClO3
8-Butyryl-2-(4-chloro-phenyl)-6-methyl-chromen-4-one
—— 2',3,5,6-Tetraacetoxy-flavon 1180-39-8 C23H18O10
2',3,5,6-Tetraacetoxy-flavon
—— (4-oxo-2-phenyl-4<i>H</i>-chromen-7-yloxy)-acetic acid-(2-dimethylamino-ethyl ester) 101121-81-7 C21H21NO5
(4-oxo-2-phenyl-4<i>H</i>-chromen-7-yloxy)-acetic acid-(2-dimethylamino-ethyl ester)
—— 7-methoxy-2,2-diphenyl-2H-chromene 1488-60-4 C22H18O2
7-methoxy-2,2-diphenyl-2H-chromene