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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
—— (2R,3S)-2-(3,4-dihydroxyphenyl)-3-hexoxy-3,4-dihydro-2H-chromene-5,7-diol 1220450-08-7 C21H26O6
(2R,3S)-2-(3,4-dihydroxyphenyl)-3-hexoxy-3,4-dihydro-2H-chromene-5,7-diol
—— macaflavanone G 1075194-71-6 C30H36O6
macaflavanone G
—— 7-(4-chlorophenyl)-9-methyl-3-phenylfuro[3,2-g]chromen-5-one 1100222-28-3 C24H15ClO3
7-(4-chlorophenyl)-9-methyl-3-phenylfuro[3,2-g]chromen-5-one
—— 6-Bromo-3-(2-phenoxyethoxy)-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-4-one 1099682-11-7 C32H28BrN3O4
6-Bromo-3-(2-phenoxyethoxy)-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-4-one
—— 7-(4-methoxyphenyl)-3-phenylfuro[3,2-g]chromen-5-one 1100222-19-2 C24H16O4
7-(4-methoxyphenyl)-3-phenylfuro[3,2-g]chromen-5-one
—— 7-(4-methoxyphenyl)-3,9-dimethylfuro[3,2-g]chromen-5-one 1100222-13-6 C20H16O4
7-(4-methoxyphenyl)-3,9-dimethylfuro[3,2-g]chromen-5-one
—— 6-Bromo-3-hydroxy-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-4-one 1099682-03-7 C24H20BrN3O3
6-Bromo-3-hydroxy-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-4-one
—— 2-Anthracen-9-yl-3-(cyclohexylmethoxy)chromen-4-one 1099682-29-7 C30H26O3
2-Anthracen-9-yl-3-(cyclohexylmethoxy)chromen-4-one
—— 2-[6-bromo-4-oxo-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-3-yl]oxy-N,N-dimethylacetamide 1099682-09-3 C28H27BrN4O4
2-[6-bromo-4-oxo-2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]chromen-3-yl]oxy-N,N-dimethylacetamide
—— 7-(4-chlorophenyl)-3,9-dimethylfuro[3,2-g]chromen-5-one 1100222-15-8 C19H13ClO3
7-(4-chlorophenyl)-3,9-dimethylfuro[3,2-g]chromen-5-one
—— 7-(4-chlorophenyl)-3-phenylfuro[3,2-g]chromen-5-one 1100222-21-6 C23H13ClO3
7-(4-chlorophenyl)-3-phenylfuro[3,2-g]chromen-5-one
—— 7-(4-methoxyphenyl)-9-methyl-3-phenylfuro[3,2-g]chromen-5-one 1100222-26-1 C25H18O4
7-(4-methoxyphenyl)-9-methyl-3-phenylfuro[3,2-g]chromen-5-one
—— 2-(4-cyanophenyl)chroman-4-one 1101612-50-3 C16H11NO2
2-(4-cyanophenyl)chroman-4-one
—— 5,7-bis(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]-2H-chromene 1072920-43-4 C21H24O7
5,7-bis(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]-2H-chromene
—— 7-{(hydrophosphoryl)-methyloxy}-3',4',5-trimethoxyflavone 1092093-65-6 C19H19O9P
7-{(hydrophosphoryl)-methyloxy}-3',4',5-trimethoxyflavone
—— ethyl 2-[3-[2-[4-[[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate 1089147-01-2 C29H31N5O10
ethyl 2-[3-[2-[4-[[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate
—— ethyl 2-[3-[2-[4-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-2,6-dioxopyrimidin-1-yl]acetate 1089146-99-5 C28H29N5O10
ethyl 2-[3-[2-[4-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-2,6-dioxopyrimidin-1-yl]acetate
—— ethyl 2-[3-[2-[4-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate 1089146-98-4 C29H31N5O10
ethyl 2-[3-[2-[4-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxymethyl]triazol-1-yl]ethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate
—— (2R,3S,4S:2R,3S)-5,7,3'4'-tetra-O-methylflavan-3-ol-4β->8-5,7,3',4'-tetra-O-methyl-flavan-3-ol 1053174-95-0 C38H42O12
(2R,3S,4S:2R,3S)-5,7,3'4'-tetra-O-methylflavan-3-ol-4β->8-5,7,3',4'-tetra-O-methyl-flavan-3-ol
—— Silydianin 29782-68-1 C25H22O10
Silydianin
—— 3-hydroxy-5-methoxyflavanone 60188-58-1 C16H14O4
3-hydroxy-5-methoxyflavanone
—— (2R,3R,4S,5S,6R)-2-[[(2R,3R)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 20728-91-0 C25H32O11
(2R,3R,4S,5S,6R)-2-[[(2R,3R)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
—— 2H-1-Benzopyran-4-ol, 3,4-dihydro-2-phenyl-, benzoate, trans- 10052-51-4 C22H18O3
2H-1-Benzopyran-4-ol, 3,4-dihydro-2-phenyl-, benzoate, trans-
—— (1R,5S,6R,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol 111467-41-5 C37H38O12
(1R,5S,6R,13S,21R)-5,13-bis(3,4-dimethoxyphenyl)-9,17,19-trimethoxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2,8,10,15(20),16,18-hexaene-6,21-diol
—— 1-{[(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]carbonyl}-N,N-dimethylazetidine-3-carboxamide 1046469-04-8 C26H30N4O3
1-{[(8S)-2,3-dimethyl-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazol-5-yl]carbonyl}-N,N-dimethylazetidine-3-carboxamide
—— (8S)-2,3-dimethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole 1046469-15-1 C22H22N4O2
(8S)-2,3-dimethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-8-(2-methylphenyl)-3,6,7,8-tetrahydrochromeno[7,8-d]imidazole
—— 6-(2-aminophenyl)-10-methyl-4-propyl-10,11-dihydro-2H,6H,12H-dipyrano[2,3-f:2',3'-h]chromene-2,12-dione 1017281-84-3 C25H23NO5
6-(2-aminophenyl)-10-methyl-4-propyl-10,11-dihydro-2H,6H,12H-dipyrano[2,3-f:2',3'-h]chromene-2,12-dione
—— Pelargonin chloride 17334-58-6 C27H31ClO15
Pelargonin chloride
—— 2-(Diethylamino)ethyl 2-(6-methoxy-4-oxo-2-phenylchromen-8-yl)acetate;hydrochloride 101002-49-7 C24H27NO5*ClH
2-(Diethylamino)ethyl 2-(6-methoxy-4-oxo-2-phenylchromen-8-yl)acetate;hydrochloride
—— N1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-2-(4-[3-(4-oxo-2-phenyl-4H-3-chromenyl)oxy]propylpiperazino)acetamide 1135197-44-2 C37H33Cl2N3O5
N1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-2-(4-[3-(4-oxo-2-phenyl-4H-3-chromenyl)oxy]propylpiperazino)acetamide
—— [(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-3-yl]oxy-6-methyloxan-3-yl] acetate 948294-72-2 C29H32O15
[(2S,3R,4R,5R,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-3-yl]oxy-6-methyloxan-3-yl] acetate
—— 2-(4-methoxyphenyl)-4H-chromene-3-carbaldehyde 62644-81-9 C17H14O3
2-(4-methoxyphenyl)-4H-chromene-3-carbaldehyde
—— 5-hydroxy-2-(3-phenylnaphth-2-yl)chromone 1000997-17-0 C25H16O3
5-hydroxy-2-(3-phenylnaphth-2-yl)chromone
—— 3-(benzyloxy)-2-[4-(benzyloxy)-3-nitrophenyl]-6-methyl-8-nitro-4H-chromen-4-one 372102-13-1 C30H22N2O8
3-(benzyloxy)-2-[4-(benzyloxy)-3-nitrophenyl]-6-methyl-8-nitro-4H-chromen-4-one
—— methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxyoxane-2-carboxylate 911212-17-4 C23H22O12
methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxyoxane-2-carboxylate
—— cis-4-Ethyl-2-phenylchroman 130444-78-9 C17H18O
cis-4-Ethyl-2-phenylchroman
—— theaflavin 3-gallate 28543-07-9 C36H28O16
theaflavin 3-gallate
—— 1-(2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-piperidine 554430-28-3 C42H59NO5Si2
1-(2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-piperidine
—— 3-O-β-D-glucosyl-7-O-β-D-(2-O-feruloyl)glucosylkaempferol 87863-93-2 C37H38O19
3-O-β-D-glucosyl-7-O-β-D-(2-O-feruloyl)glucosylkaempferol
—— 4H-1-Benzopyran-4-one, 3-[[6-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-beta-D-galactopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- 106915-93-9 C27H28O16
4H-1-Benzopyran-4-one, 3-[[6-O-(4-carboxy-3-hydroxy-3-methyl-1-oxobutyl)-beta-D-galactopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
—— 9-Methoxy-2-phenyl-4H-naphtho[1,2-b]pyran-4-one 89504-51-8 C20H14O3
9-Methoxy-2-phenyl-4H-naphtho[1,2-b]pyran-4-one
—— apigenin 7-O-6''-acetyl-glucoside 72741-92-5 C23H22O11
apigenin 7-O-6''-acetyl-glucoside
—— [(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate 106548-98-5 C66H50O30
[(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
—— Neochamaejasmin B 90411-12-4 C30H22O10
Neochamaejasmin B
—— (2S,3R,4R,5S,6R)-2-[(2R,3S)-2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-6-yl]-6-(hydroxymethyl)oxane-3,4,5-triol 103215-51-6 C25H32O11
(2S,3R,4R,5S,6R)-2-[(2R,3S)-2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-3,4-dihydro-2H-chromen-6-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
—— Floranol 502685-14-5 C21H22O7
Floranol
—— 2-(3,4-dihydroxy-5-nitrophenyl)-4H-1-benzopyran-4-one 134611-71-5 C15H9NO6
2-(3,4-dihydroxy-5-nitrophenyl)-4H-1-benzopyran-4-one
—— kaempferol 3-O-rhamnoside 7-O-rhamnoside —— C27H30O14
kaempferol 3-O-rhamnoside 7-O-rhamnoside
—— 4H-1-Benzopyran-8-acetic acid, 2-(diethylamino)ethyl ester, hydrochloride 101002-48-6 C23H24ClNO4*ClH
4H-1-Benzopyran-8-acetic acid, 2-(diethylamino)ethyl ester, hydrochloride
—— Salz 1715-55-5 C9H10N4O4*C19H19NO3
Salz