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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
—— (R)-2-(1-naphthyl)chromanone 1101612-52-5 C19H14O2
(R)-2-(1-naphthyl)chromanone
—— 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-(methoxymethoxy)-3-(3-methyl-2-buten-1-yl)-4H-chromen-4-one 1610962-20-3 C22H22O7
2-(2,4-dihydroxyphenyl)-5-hydroxy-7-(methoxymethoxy)-3-(3-methyl-2-buten-1-yl)-4H-chromen-4-one
—— (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman 850816-11-4 C68H70O7
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman
—— 20754-85-2 C29H22O5
—— kaempferol 6-C-β-D-glucopyranoside 28225-10-7 C21H20O11
kaempferol 6-C-β-D-glucopyranoside
—— tambuletin 32427-55-7 C23H24O13
tambuletin
—— 14,14-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,22-dioxa-20-azahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,3'-cyclohexane]-21-one 1262589-85-4 C44H41NO5
14,14-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,22-dioxa-20-azahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaene-9,3'-cyclohexane]-21-one
—— 9-Hydroxy-8-(3',4'-methylenedioxyphenyl)-5-methoxy-2,2-dimethyl-3,4-dihydro-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-one 88055-40-7 C22H20O7
9-Hydroxy-8-(3',4'-methylenedioxyphenyl)-5-methoxy-2,2-dimethyl-3,4-dihydro-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-one
—— (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 1-tert-butoxycarbonylpyrrolidine-2-carboxylate 1158555-87-3 C25H25NO10
(S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 1-tert-butoxycarbonylpyrrolidine-2-carboxylate
—— Acetic acid (2R,3S)-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-3-yl ester 101946-96-7 C19H18O6
Acetic acid (2R,3S)-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-3-yl ester
—— 8-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-5,7-dimethoxy-chromen-4-one 89456-37-1 C18H16O7
8-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-5,7-dimethoxy-chromen-4-one
—— 1400698-23-8 C16H10F2O3
—— 3-(3-bromopropoxy)-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 114050-92-9 C20H19BrO5
3-(3-bromopropoxy)-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
—— 3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one 1529772-92-6 C36H28N2O5
3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one
—— dimethyl 4-(6-chloro-3-methoxy-4H-1-benzopyran-4-on-2-yl)benzylphosphonate 166305-18-6 C19H18ClO6P
dimethyl 4-(6-chloro-3-methoxy-4H-1-benzopyran-4-on-2-yl)benzylphosphonate
—— 4-oxo-2-(2,6-difluorophenyl)-4H-1-benzopyran-8-acetic acid 131402-00-1 C17H10F2O4
4-oxo-2-(2,6-difluorophenyl)-4H-1-benzopyran-8-acetic acid
—— 2,4-bis(4-methoxyphenyl)-4-methyl-4H-benzo[h]chromene 1640099-12-2 C28H24O3
2,4-bis(4-methoxyphenyl)-4-methyl-4H-benzo[h]chromene
—— 8-Brom-5-acetoxy-7-methoxy-flavon 93869-48-8 C18H13BrO5
8-Brom-5-acetoxy-7-methoxy-flavon
—— 2-([1,1'-biphenyl]-2-yl)-2H-chromene 1362479-29-5 C21H16O
2-([1,1'-biphenyl]-2-yl)-2H-chromene
—— (2R<sup>*</sup>,3R<sup>*</sup>,4S<sup>*</sup>)-3,4-diacetoxy-5,4'-dimethoxy flavan 86788-67-2 C21H22O7
(2R<sup>*</sup>,3R<sup>*</sup>,4S<sup>*</sup>)-3,4-diacetoxy-5,4'-dimethoxy flavan
—— 21,21-Difluoro-14,14-bis(4-methoxyphenyl)-9,20,22-trimethyl-15-oxa-20,22-diazahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaen-9-ol 1262589-91-2 C38H32F2N2O4
21,21-Difluoro-14,14-bis(4-methoxyphenyl)-9,20,22-trimethyl-15-oxa-20,22-diazahexacyclo[15.7.0.02,10.03,8.011,16.019,23]tetracosa-1(24),2(10),3,5,7,11(16),12,17,19(23)-nonaen-9-ol
—— 3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-((4-fluorobenzyl)oxy)phenyl)-5-hydroxy-4H-chromen-4-one 1610737-59-1 C43H33FO7
3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-((4-fluorobenzyl)oxy)phenyl)-5-hydroxy-4H-chromen-4-one
—— 2,3-cis-2-methoxy-4'-nitroflavan-3-ol 88215-01-4 C16H15NO5
2,3-cis-2-methoxy-4'-nitroflavan-3-ol
—— 4-(p-benzyloxyphenyl)-4-hydroxy-7-methoxy-2-phenyl-4H-chromene 153936-30-2 C29H24O4
4-(p-benzyloxyphenyl)-4-hydroxy-7-methoxy-2-phenyl-4H-chromene
—— 2-phenylchromone-3-phosphonic acid 146298-01-3 C15H11O5P
2-phenylchromone-3-phosphonic acid
—— (+-)-trans-3-hydroxy-2-phenyl-chroman-4-one-phenylhydrazone 94871-82-6 C21H18N2O2
(+-)-trans-3-hydroxy-2-phenyl-chroman-4-one-phenylhydrazone
—— 2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid ethyl ester 774582-08-0 C21H22N2O3
2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid ethyl ester
—— 6-ethyl-2-phenyl-chroman-7-ol 98220-95-2 C17H18O2
6-ethyl-2-phenyl-chroman-7-ol
—— 3-(3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((S)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol trifluoroacetate 1352306-98-9 C2HF3O2*C30H33NO4
3-(3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((S)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-6-ol trifluoroacetate
—— 2'-Methoxy-flavanon 123743-14-6 C16H14O3
2'-Methoxy-flavanon
—— (3Z)-2-phenyl-3-[(4-phenylmethoxyphenyl)methylidene]chromen-4-one 112014-65-0 C29H22O3
(3Z)-2-phenyl-3-[(4-phenylmethoxyphenyl)methylidene]chromen-4-one
—— 2,2-bis-(4-methoxy-phenyl)-4,6-dimethyl-2<i>H</i>-chromene 38472-52-5 C25H24O3
2,2-bis-(4-methoxy-phenyl)-4,6-dimethyl-2<i>H</i>-chromene
—— 5-methoxycarbonyl-3,3-diphenyl-3H-naphtho[2,1-b]pyrane 853305-73-4 C27H20O3
5-methoxycarbonyl-3,3-diphenyl-3H-naphtho[2,1-b]pyrane
—— 8-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 89456-31-5 C32H28O7
8-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
—— 5-(6-Bromo-7-hydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxy-benzoic acid 78050-76-7 C16H9BrO6
5-(6-Bromo-7-hydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxy-benzoic acid
—— 8-Acetyl-7-hydroxy-3',4'-dimethoxyflavanone 116470-12-3 C19H18O6
8-Acetyl-7-hydroxy-3',4'-dimethoxyflavanone
—— 11-Methoxy-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-naphthalen-1-ylspiro[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] 1278539-35-7 C54H50O4
11-Methoxy-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-naphthalen-1-ylspiro[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]
—— 11-Cyclobutyloxy-10-(2,4-dimethoxyphenyl)-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[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] 1278523-72-0 C55H56O6
11-Cyclobutyloxy-10-(2,4-dimethoxyphenyl)-5,5-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[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]
—— 2-([1,1'-biphenyl]-4-yl)-5,6,7-trimethoxy-4H-chromen-4-one 859505-62-7 C24H20O5
2-([1,1'-biphenyl]-4-yl)-5,6,7-trimethoxy-4H-chromen-4-one
—— (R)-2,2,2-trifluoro-N-(3-(4-oxochroman-2-yl)phenyl)acetamide 1438763-08-6 C17H12F3NO3
(R)-2,2,2-trifluoro-N-(3-(4-oxochroman-2-yl)phenyl)acetamide
—— 2,8-bis(4-bromophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione 1609404-66-1 C24H12Br2O4
2,8-bis(4-bromophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione
—— monopotassium mono(5-hydroxy-4-oxo-2-(4-(sulfonatooxy)phenyl)-4H-chromene-3,7-diyl bis(sulfate)) 116097-12-2 C15H7O15S3*3K
monopotassium mono(5-hydroxy-4-oxo-2-(4-(sulfonatooxy)phenyl)-4H-chromene-3,7-diyl bis(sulfate))
—— 4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-(4-morpholin-4-ylphenyl)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-21,3'-cyclohexane]-11-yl]morpholine 1278523-86-6 C57H60N2O5
4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-10-(4-morpholin-4-ylphenyl)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-21,3'-cyclohexane]-11-yl]morpholine
—— (2R,3S,4R,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol 182967-16-4 C46H40O16
(2R,3S,4R,2'R,3'S,2''R,3''S,4''R)-2,2''-Bis-(3,4-dihydroxy-phenyl)-2'-(3-hydroxy-4-methoxy-phenyl)-3,4,3',4',3'',4''-hexahydro-2H,2'H,2''H-[4,6';8',4'']terchromene-3,7,3',5',7',3'',7''-heptaol
—— 2,3-cis-3-bromo-2-(2,4-cis-flavan-4-yloxy)flavan 95731-43-4 C30H25BrO3
2,3-cis-3-bromo-2-(2,4-cis-flavan-4-yloxy)flavan
—— 6,8''-biflavone 1247006-90-1 C30H18O4
6,8''-biflavone
—— 4',5-bis-(ethoxycarbonyloxy)-3,3',7-trimethoxyflavone 77813-44-6 C24H24O11
4',5-bis-(ethoxycarbonyloxy)-3,3',7-trimethoxyflavone
—— (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-4-methylpentanoate 1158555-60-2 C26H29NO10
(S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-4-methylpentanoate
—— <4,8>-2,3-trans-3,4-cis:2,3-trans-(-)-fisetinidol-(+)catechin heptamethyl ether diacetate 1053174-97-2 C42H46O14
<4,8>-2,3-trans-3,4-cis:2,3-trans-(-)-fisetinidol-(+)catechin heptamethyl ether diacetate
—— 5,7-Diethoxy-4'-hydroxyflavanon 26207-75-0 C19H20O5
5,7-Diethoxy-4'-hydroxyflavanon