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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
—— 3-(2-chlorobenzylidene)flavanone 234093-70-0 C22H15ClO2
3-(2-chlorobenzylidene)flavanone
—— 9-oxo-9a-(2-phenyloxiran-2-yl)-3,3a,9,9a-tetrahydro<1>benzopyrano<2,3-d>pyrazole 111570-57-1 C18H14N2O3
9-oxo-9a-(2-phenyloxiran-2-yl)-3,3a,9,9a-tetrahydro<1>benzopyrano<2,3-d>pyrazole
—— 3,7-diethoxy-2-(4-ethoxy-phenyl)-5,8-dihydroxy-chromen-4-one 859050-43-4 C21H22O7
3,7-diethoxy-2-(4-ethoxy-phenyl)-5,8-dihydroxy-chromen-4-one
—— (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 4-amino-2-(tert-butoxycarbonylamino)-4-oxobutanoate 1158555-85-1 C24H24N2O11
(S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 4-amino-2-(tert-butoxycarbonylamino)-4-oxobutanoate
—— (2S,4R)-(+)-4-aminoflavan hydrochloride 117556-55-5 C15H15NO*ClH
(2S,4R)-(+)-4-aminoflavan hydrochloride
—— 4-[4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-(2-methylpiperidin-1-yl)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]-10-yl]phenyl]morpholine 1278523-83-3 C59H64N2O4
4-[4-[5,5-Bis(4-methoxyphenyl)-1',1',5',5'-tetramethyl-11-(2-methylpiperidin-1-yl)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]-10-yl]phenyl]morpholine
—— N-(4-methoxyphenyl)-2-(4-oxo-2-phenyl-4H-chromen-3-yloxy)acetamide 1070399-62-0 C24H19NO5
N-(4-methoxyphenyl)-2-(4-oxo-2-phenyl-4H-chromen-3-yloxy)acetamide
—— rac-2-(4-bromophenyl)-2H-chromene-3-carboxylic acid 1204754-91-5 C16H11BrO3
rac-2-(4-bromophenyl)-2H-chromene-3-carboxylic acid
—— 7-<(2,3-Dimethyl-5-oxo-1-phenyl-Δ<sup>3</sup>-pyrazolin-4-yl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen 103306-57-6 C28H23N3O5
7-<(2,3-Dimethyl-5-oxo-1-phenyl-Δ<sup>3</sup>-pyrazolin-4-yl)-carbamoylmethoxy>-4-oxo-2-phenyl-4H-chromen
—— N-(biphenyl-4-yl)-2-(4-oxo-2-phenyl-4H-chromen-6-yloxy)acetamide 1070399-71-1 C29H21NO4
N-(biphenyl-4-yl)-2-(4-oxo-2-phenyl-4H-chromen-6-yloxy)acetamide
—— 10-methyl-2-naphthalen-1-yl-pyrano[2,3-<i>f</i>]chromene-4,8-dione 32942-43-1 C23H14O4
10-methyl-2-naphthalen-1-yl-pyrano[2,3-<i>f</i>]chromene-4,8-dione
—— 5,7-bis(2,3-Dihydroxypropoxy)-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4H-1-benzopyran-4-one 178367-50-5 C25H30O10
5,7-bis(2,3-Dihydroxypropoxy)-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4H-1-benzopyran-4-one
—— trans-flavan-4-ol tosylate 104819-73-0 C22H20O4S
trans-flavan-4-ol tosylate
—— 7-benzyloxy-5-hydroxy-3,8-dimethoxy-2-phenyl-chromen-4-one 33803-32-6 C24H20O6
7-benzyloxy-5-hydroxy-3,8-dimethoxy-2-phenyl-chromen-4-one
—— (2R,3R)-2-(3,4-dihydroxy-5-(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychroman-5,7-diyl bis(2-nitrobenzenesulfonate) 1186527-14-9 C33H23N3O19S3
(2R,3R)-2-(3,4-dihydroxy-5-(2-nitrophenylsulfonyloxy)phenyl)-3-hydroxychroman-5,7-diyl bis(2-nitrobenzenesulfonate)
—— Gossypetin-7-β-D-glucopyranosid-nonaacetat 42215-81-6 C39H38O22
Gossypetin-7-β-D-glucopyranosid-nonaacetat
—— 3'-Benzyloxy-5,7,8,2'-tetramethoxy-flavon 23806-67-9 C26H24O7
3'-Benzyloxy-5,7,8,2'-tetramethoxy-flavon
—— 7-{(N-bezenesulfonylcarbamoyl)methyloxy}-3',4',5-trimethoxyflavone 1092093-64-5 C26H23NO9S
7-{(N-bezenesulfonylcarbamoyl)methyloxy}-3',4',5-trimethoxyflavone
—— 1,3-di-(3-phenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 874365-04-5 C44H30O2
1,3-di-(3-phenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene
—— 5-hydroxy-3',4',5',7-tetramethoxy-8-prenylflavanone 62252-12-4 C24H28O7
5-hydroxy-3',4',5',7-tetramethoxy-8-prenylflavanone
—— 2-(2,5-dimethoxy-phenyl)-7-hydroxy-3-methoxy-chromen-4-one 743466-66-2 C18H16O6
2-(2,5-dimethoxy-phenyl)-7-hydroxy-3-methoxy-chromen-4-one
—— 4'-Benzyloxy-3',5-dihydroxy-7-methoxy-flavon-3-O-octa-O-acetyl-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid 83170-22-3 C57H64O28
4'-Benzyloxy-3',5-dihydroxy-7-methoxy-flavon-3-O-octa-O-acetyl-<O-α-L-rhamnopyranosyl-(1-4)-O-α-L-rhamnopyranosyl-(1-6)>-β-D-galaktopyranosid
—— 3,3-diphenyl-9,10,12,13,15,16,18,19-octahydro-3H-[1,4,7,10,13]pentaoxacyclopentadeca[2′,3′:4,5]benzo[f]chromene 1394035-44-9 C33H32O6
3,3-diphenyl-9,10,12,13,15,16,18,19-octahydro-3H-[1,4,7,10,13]pentaoxacyclopentadeca[2′,3′:4,5]benzo[f]chromene
—— kaempferol 3-O-α-L-(5''-O-acetyl)-arabinofuranosyl-7-O-α-L-rhamnopyranoside 1206531-79-4 C28H30O15
kaempferol 3-O-α-L-(5''-O-acetyl)-arabinofuranosyl-7-O-α-L-rhamnopyranoside
—— 6-acetylamino-2-(3-hydroxy-phenyl)-chromen-4-one 109090-65-5 C17H13NO4
6-acetylamino-2-(3-hydroxy-phenyl)-chromen-4-one
—— (2E)-ethyl 3-(4-oxo-2-phenyl-4H-chromen-6-yl)-8-methoxy-acrylate 1174710-11-2 C21H18O5
(2E)-ethyl 3-(4-oxo-2-phenyl-4H-chromen-6-yl)-8-methoxy-acrylate
—— 2-ethyl-2-(4-methoxyphenyl)-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol 1432504-70-5 C25H22O3
2-ethyl-2-(4-methoxyphenyl)-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol
—— 2-(3,4-Diethoxy-phenyl)-8-methoxy-3-nitro-chroman 106824-25-3 C20H23NO6
2-(3,4-Diethoxy-phenyl)-8-methoxy-3-nitro-chroman
—— (+-)-N-(4c-chloro-2r-phenyl-chroman-3t-yl)-acetamide 109697-59-8 C17H16ClNO2
(+-)-N-(4c-chloro-2r-phenyl-chroman-3t-yl)-acetamide
—— 21,21-Difluoro-14-(4-methoxy-3-morpholin-4-ylphenyl)-14-(4-methoxyphenyl)-22-methylspiro[15,20-dioxa-22-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-9,2'-bicyclo[2.2.1]heptane] 1262589-92-3 C46H42F2N2O5
21,21-Difluoro-14-(4-methoxy-3-morpholin-4-ylphenyl)-14-(4-methoxyphenyl)-22-methylspiro[15,20-dioxa-22-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-9,2'-bicyclo[2.2.1]heptane]
—— 8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one 131402-11-4 C17H10FNO2
8-cyanomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one
—— (-)-mesquitol 609361-12-8 C15H14O6
(-)-mesquitol
—— 7-benzyloxy-5,8-dihydroxy-3-methoxy-2-phenyl-chromen-4-one 33803-33-7 C23H18O6
7-benzyloxy-5,8-dihydroxy-3-methoxy-2-phenyl-chromen-4-one
—— (2R,3S)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate 1365537-06-9 C35H36O8
(2R,3S)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate
—— 2-benzo[1,3]dioxol-5-yl-6-methyl-chromen-4-one 93327-99-2 C17H12O4
2-benzo[1,3]dioxol-5-yl-6-methyl-chromen-4-one
—— 7-(3-thiocyanatopropoxy)-2-phenyl-4H-1-benzopyran-4-one 155373-79-8 C19H15NO3S
7-(3-thiocyanatopropoxy)-2-phenyl-4H-1-benzopyran-4-one
—— 4-nitro-N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide 1467668-60-5 C24H20N2O9S
4-nitro-N-(3-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide
—— (3E)-3-[(4-fluorophenyl)methylidene]-2-phenylchromen-4-one 112014-55-8 C22H15FO2
(3E)-3-[(4-fluorophenyl)methylidene]-2-phenylchromen-4-one
—— 21,22-Difluoro-14,14-bis(4-methoxyphenyl)-1',1',5',5',20-pentamethylspiro[15,23-dioxa-20-azahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane] 1262589-89-8 C46H45F2NO4
21,22-Difluoro-14,14-bis(4-methoxyphenyl)-1',1',5',5',20-pentamethylspiro[15,23-dioxa-20-azahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane]
—— 3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-oxo-2-phenyl-4H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 1309445-41-7 C43H46O22
3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-4-oxo-2-phenyl-4H-chromen-7-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
—— 7-O-β-D-acetylglucosylflavone 102030-40-0 C29H28O12
7-O-β-D-acetylglucosylflavone
—— 5-acetoxy-3,(4-methoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran 143099-04-1 C28H21FO4
5-acetoxy-3,(4-methoxyphenyl),3(2-fluorophenyl)-3H-naphtho[2,1-b]pyran
—— 7-acetoxy-2,8-bis-(2,4-diacetoxy-phenyl)-phenoxazin-3-one 98879-46-0 C34H25NO12
7-acetoxy-2,8-bis-(2,4-diacetoxy-phenyl)-phenoxazin-3-one
—— hesperidin dihydrochalcone 19282-00-9 C29H38O15
hesperidin dihydrochalcone
—— 2-(3,6-dimethyl-2-benzofuryl)-7-methoxychromone 85461-40-1 C20H16O4
2-(3,6-dimethyl-2-benzofuryl)-7-methoxychromone
—— 2,3-cis-3,4-trans-3-bromo-2,4'-dimethoxy-4-phenylflavan 88186-78-1 C23H21BrO3
2,3-cis-3,4-trans-3-bromo-2,4'-dimethoxy-4-phenylflavan
—— 6-carbethoxy-2'-isopropoxy-5'-methyl-flavone 66833-99-6 C22H22O5
6-carbethoxy-2'-isopropoxy-5'-methyl-flavone
—— 6-carboxy-8-propyl-2'-isopropoxy-flavone 57009-46-8 C22H22O5
6-carboxy-8-propyl-2'-isopropoxy-flavone
—— 2-morpholin-4-ylethyl (E)-3-(4-oxo-2-phenylchromen-8-yl)prop-2-enoate 87626-89-9 C24H23NO5
2-morpholin-4-ylethyl (E)-3-(4-oxo-2-phenylchromen-8-yl)prop-2-enoate
—— 1-[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]-11-yl]-2-methylpiperidine 1278523-63-9 C57H61NO5
1-[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]-11-yl]-2-methylpiperidine