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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
—— 5,8-Dihydroxy-3,7,4'-trimethoxy-3'-benzyloxy-flavon 4670-42-2 C25H22O8
5,8-Dihydroxy-3,7,4'-trimethoxy-3'-benzyloxy-flavon
—— Keyakinin-heptaacetat 10515-28-3 C36H36O18
Keyakinin-heptaacetat
—— delphinidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 1346257-30-4 C44H47O26
delphinidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]
—— 5-Hydroxy-2-(3,4-dimethoxyphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one 178366-85-3 C20H20O8
5-Hydroxy-2-(3,4-dimethoxyphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one
—— 4.4-Diphenyl-flavan 2859-90-7 C27H22O
4.4-Diphenyl-flavan
—— (S)-2-(4-(2-(fluoro-1-hydroxyethyl)phenyl))-4H-chromen-4-one 1587709-74-7 C17H13FO3
(S)-2-(4-(2-(fluoro-1-hydroxyethyl)phenyl))-4H-chromen-4-one
—— 3-[1,3,11a-trihydroxy-5a-(4-hydroxyphenyl)-12-oxochromeno[2,3-b][1,4]benzodioxin-8-yl]prop-2-enoic acid 1219698-79-9 C24H16O10
3-[1,3,11a-trihydroxy-5a-(4-hydroxyphenyl)-12-oxochromeno[2,3-b][1,4]benzodioxin-8-yl]prop-2-enoic acid
—— Acetic acid 7-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-6-((2R,4R,5S,6R)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yl)-4-oxo-4H-chromen-5-yl ester 124961-73-5 C32H32O14
Acetic acid 7-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-6-((2R,4R,5S,6R)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yl)-4-oxo-4H-chromen-5-yl ester
—— 7,4'-Dibenzyl-isorhamnetin-3-mono-β-D-glucosid 6743-89-1 C36H34O12
7,4'-Dibenzyl-isorhamnetin-3-mono-β-D-glucosid
—— N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-3-bromobenzenesulfonamide 260063-96-5 C22H14BrNO7S
N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-3-bromobenzenesulfonamide
—— Hexa-O-methyl-6-methyl-myricetin 103640-77-3 C22H24O8
Hexa-O-methyl-6-methyl-myricetin
—— 7-methoxy-2-p-tolyl-3-nitro-2H-chromene 113495-53-7 C17H15NO4
7-methoxy-2-p-tolyl-3-nitro-2H-chromene
—— 2,2'-((ethane-1,2-diylbis(oxy))bis(4,1-phenylene))bis(5,7-bis(benzyloxy)-4H-chromen-4-one) 916330-64-8 C60H46O10
2,2'-((ethane-1,2-diylbis(oxy))bis(4,1-phenylene))bis(5,7-bis(benzyloxy)-4H-chromen-4-one)
—— (2R,3S)-6-Chloro-3-hydroxy-2-(4-methoxy-phenyl)-chroman-4-one 139006-42-1 C16H13ClO4
(2R,3S)-6-Chloro-3-hydroxy-2-(4-methoxy-phenyl)-chroman-4-one
—— 124731-53-9 C17H14ClNO4
—— 5,14-dihydroxy-2-phenyl-4H,13H,14H-pyrano[3,2-c:6,5-h']dichromene-4,13-dione 1614253-89-2 C25H14O7
5,14-dihydroxy-2-phenyl-4H,13H,14H-pyrano[3,2-c:6,5-h']dichromene-4,13-dione
—— 3-[5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[2,3-b][1,4]benzodioxin-9-yl]prop-2-enoic acid 1219698-58-4 C24H16O11
3-[5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[2,3-b][1,4]benzodioxin-9-yl]prop-2-enoic acid
—— 5,7-dimethoxy-2-(3,4,5-tribenzyloxyphenyl)-2H-chromene 701284-28-8 C38H34O6
5,7-dimethoxy-2-(3,4,5-tribenzyloxyphenyl)-2H-chromene
—— Toluene-4-sulfonic acid 3,5,8-trimethoxy-4-oxo-2-(3,4,5-trimethoxy-phenyl)-4H-chromen-7-yl ester 117155-47-2 C28H28O11S
Toluene-4-sulfonic acid 3,5,8-trimethoxy-4-oxo-2-(3,4,5-trimethoxy-phenyl)-4H-chromen-7-yl ester
—— 2-(2-benzyloxy-4-methoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-4-one 13972-65-1 C25H24O7
2-(2-benzyloxy-4-methoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-4-one
—— 6-Chlor-4'-chloracetoxy-flavon 3473-37-8 C17H10Cl2O4
6-Chlor-4'-chloracetoxy-flavon
—— 7-O-Allyl-quercetin-3,5,3,4'-tetramethylaether 2181-10-4 C22H22O7
7-O-Allyl-quercetin-3,5,3,4'-tetramethylaether
—— 5,7-dimethyl-2-(3,4,5-tribenzyloxyphenyl)-2H-chromen-3(4H)-one 701284-39-1 C38H34O5
5,7-dimethyl-2-(3,4,5-tribenzyloxyphenyl)-2H-chromen-3(4H)-one
—— 4-bromo-N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide 1467668-59-2 C24H20BrNO7S
4-bromo-N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide
—— S-[(2R,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] ethanethioate 94953-61-4 C17H14O3S
S-[(2R,3R)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] ethanethioate
—— 1-(4-fluorophenyl)-2-(2-(p-tolyl)-4H-chromen-4-ylidene)ethan-1-one 1374022-16-8 C24H17FO2
1-(4-fluorophenyl)-2-(2-(p-tolyl)-4H-chromen-4-ylidene)ethan-1-one
—— 2-Hydroxy-4',6'-dimethoxyflavon 63487-14-9 C17H14O5
2-Hydroxy-4',6'-dimethoxyflavon
—— 6-bromo-2-(4-methanesulfonyl-phenyl)-chroman 1426900-04-0 C16H15BrO3S
6-bromo-2-(4-methanesulfonyl-phenyl)-chroman
—— 1514898-61-3 C28H19ClN2O3S
—— 5-Methoxy-7-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one 95690-54-3 C36H48O15
5-Methoxy-7-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one
—— 6-Chloro-5-methoxyflavone 87953-89-7 C16H11ClO3
6-Chloro-5-methoxyflavone
—— 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-isopentyl-8-(tert-pentyl)-4H-chromen-4-one 1610962-18-9 C25H30O6
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-isopentyl-8-(tert-pentyl)-4H-chromen-4-one
—— 8-[2-Hydroxy-3-(propylamino)propoxy]flavone hydrochloride 120462-30-8 C21H23NO4*ClH
8-[2-Hydroxy-3-(propylamino)propoxy]flavone hydrochloride
—— Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-5-methyl-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester ethyl ester 209746-60-1 C30H34O11
Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-5-methyl-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester ethyl ester
—— 4'-chloro-5-methoxyflavanone 126494-91-5 C16H13ClO3
4'-chloro-5-methoxyflavanone
—— 2-benzo[1,3]dioxol-5-yl-6-nitro-chromen-4-one 130986-56-0 C16H9NO6
2-benzo[1,3]dioxol-5-yl-6-nitro-chromen-4-one
—— (2R,4S)-2-Phenyl-chroman-4-ylamine; compound with ((1S,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid 117556-54-4 C10H16O4S*C15H15NO
(2R,4S)-2-Phenyl-chroman-4-ylamine; compound with ((1S,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid
—— 5,7-dimethoxy-2-(4-methoxy-phenyl)-8-[tetrakis-O-(4-nitro-benzoyl)-β-D-glucopyranosyl]-chromen-4-one 120968-77-6 C52H38N4O22
5,7-dimethoxy-2-(4-methoxy-phenyl)-8-[tetrakis-O-(4-nitro-benzoyl)-β-D-glucopyranosyl]-chromen-4-one
—— 6-(8-(4-cyanophenyl)naphthalen-1-yl)-2,2-diphenyl-2H-chromene 1374400-50-6 C38H25NO
6-(8-(4-cyanophenyl)naphthalen-1-yl)-2,2-diphenyl-2H-chromene
—— 1400698-27-2 C17H12F2O2
—— 3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran 163672-90-0 C28H21FO5
3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran
—— 1093184-28-1 C79H116N2O56
—— 3,4',7-Trihydroxy-flavanon-triacetat 6515-25-9 C21H18O8
3,4',7-Trihydroxy-flavanon-triacetat
—— 7-Hydroxy-6-carboxy-3-ethyl-flavon 33845-81-7 C18H14O5
7-Hydroxy-6-carboxy-3-ethyl-flavon
—— 2-(3,4-dihydroxyphenyl)-3,8-dihydroxy-4H-chromen-4-one 260063-38-5 C15H10O6
2-(3,4-dihydroxyphenyl)-3,8-dihydroxy-4H-chromen-4-one
—— 3,5,7-Trimethyl-flavon 2552-80-9 C18H16O2
3,5,7-Trimethyl-flavon
—— (1aS,7aR)-4,6-dihydroxy-1a-(3-hydroxy-4-((2R,3R,4S,5R)-3,4,5-trihydroxy-6(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-7a-(2-hydroxy-4-(3,5,7-trihydroxy-6-methyl-4-oxo-4H-chromen-2-yl)phenoxy)-5-methyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one 1428956-19-7 C38H32O19
(1aS,7aR)-4,6-dihydroxy-1a-(3-hydroxy-4-((2R,3R,4S,5R)-3,4,5-trihydroxy-6(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-7a-(2-hydroxy-4-(3,5,7-trihydroxy-6-methyl-4-oxo-4H-chromen-2-yl)phenoxy)-5-methyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one
—— Scutellarein-7-rutenosid 847032-38-6 C27H30O15
Scutellarein-7-rutenosid
—— 3-Acetoxy-6-methyl-4'-nitro-flavon 2754-80-5 C18H13NO6
3-Acetoxy-6-methyl-4'-nitro-flavon
—— 6-Methyl-3,7,8,3',4'-penta-O-methyl-gossypetin 16807-44-6 C21H22O8
6-Methyl-3,7,8,3',4'-penta-O-methyl-gossypetin