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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
—— <i>N</i>-(3-methyl-4-oxo-2-phenyl-4<i>H</i>-chromen-6-yl)-2-morpholin-4-yl-acetamide 56822-69-6 C22H22N2O4
<i>N</i>-(3-methyl-4-oxo-2-phenyl-4<i>H</i>-chromen-6-yl)-2-morpholin-4-yl-acetamide
—— 2-[4-[(2-Oxocyclopentyl)carbonyl]phenyl]-4H-1-benzopyran-4-one 55737-24-1 C21H16O4
2-[4-[(2-Oxocyclopentyl)carbonyl]phenyl]-4H-1-benzopyran-4-one
—— 3-[(3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one 64828-40-6 C33H40O21
3-[(3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(3R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
—— 2,5-bis[4-(benzyloxy)phenyl]-6-[(E)-3-{4-(benzyloxy)phenyl}acryloyl]-7-methylchroman-4-one 1365935-48-3 C52H42O6
2,5-bis[4-(benzyloxy)phenyl]-6-[(E)-3-{4-(benzyloxy)phenyl}acryloyl]-7-methylchroman-4-one
—— 2-[4-(benzyloxy)phenyl]-6-[(E)-3-{4-(benzyloxy)phenyl}acryloyl]-5-(4-bromophenyl)-7-methylchroman-4-one 1365935-28-9 C45H35BrO5
2-[4-(benzyloxy)phenyl]-6-[(E)-3-{4-(benzyloxy)phenyl}acryloyl]-5-(4-bromophenyl)-7-methylchroman-4-one
—— 6,8-dichloronaringenin 68180-09-6 C15H10Cl2O5
6,8-dichloronaringenin
—— Toluene-4-sulfonic acid 5,6,7-trihydroxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester 170235-01-5 C23H18O9S
Toluene-4-sulfonic acid 5,6,7-trihydroxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-3-yl ester
—— 1-[4-[(2S)-7-(2,2-Dimethyl-1-oxopropyl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl]-2,2-dimethyl-1-propanone 1185245-54-8 C25H30O3
1-[4-[(2S)-7-(2,2-Dimethyl-1-oxopropyl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl]-2,2-dimethyl-1-propanone
—— 1,13-bis[4'-(6-bromo-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane 958457-97-1 C38H32Br2O9
1,13-bis[4'-(6-bromo-4H-chromen-4-on-2-yl)-phenyl]-1,4,7,10,13-pentaoxatridecane
—— 4'-Methoxy-5-acetoxy-6,7-methylendioxyflavon 68203-92-9 C19H14O7
4'-Methoxy-5-acetoxy-6,7-methylendioxyflavon
—— 2-[[2-(2,4-Dihydroxyphenyl)-3,4-dihydro-4-oxo-2H-1-benzopyran-7-yl]oxy]acetic acid 40433-00-9 C17H14O7
2-[[2-(2,4-Dihydroxyphenyl)-3,4-dihydro-4-oxo-2H-1-benzopyran-7-yl]oxy]acetic acid
—— 4H,8H-Benzo[1,2-b:3,4-ba(2)]dipyran-4-one, 2-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)-2,3,9,10-tetrahydro-8,8-dimethyl- 59870-66-5 C25H28O4
4H,8H-Benzo[1,2-b:3,4-ba(2)]dipyran-4-one, 2-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)-2,3,9,10-tetrahydro-8,8-dimethyl-
—— 8-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one 89456-29-1 C31H26O6
8-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,7-dimethoxy-4H-chromen-4-one
—— (2R,3S,4S)-4-(2,4-Dimethoxy-phenyl)-2-(3,4-dimethoxy-phenyl)-7-methoxy-chroman-3-ol 78284-49-8 C26H28O7
(2R,3S,4S)-4-(2,4-Dimethoxy-phenyl)-2-(3,4-dimethoxy-phenyl)-7-methoxy-chroman-3-ol
—— 21-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5',21-pentamethylspiro[15,20,23-trioxahexacyclo[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] 1268817-13-5 C47H48O6
21-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5',21-pentamethylspiro[15,20,23-trioxahexacyclo[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]
—— 3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran 761409-17-0 C40H37NO5
3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran
—— 1462876-35-2 C34H24Cl2O7
—— (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol;chloride 26984-07-6 C21H23ClO13
(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;2-(3,4,5-trihydroxyphenyl)chromenylium-3,5,7-triol;chloride
—— Flavone, 3,3a(2),4a(2),5,7-pentahydroxy-8-(morpholinomethyl)-, 3-I(2)-D-rutinoside 6167-40-4 C32H39NO17
Flavone, 3,3a(2),4a(2),5,7-pentahydroxy-8-(morpholinomethyl)-, 3-I(2)-D-rutinoside
—— 2-[2,5-Dimethoxy-4-(phenylmethoxy)phenyl]-5,6,7-trimethoxy-4H-1-benzopyran-4-one 105827-37-0 C27H26O8
2-[2,5-Dimethoxy-4-(phenylmethoxy)phenyl]-5,6,7-trimethoxy-4H-1-benzopyran-4-one
—— 5-[4-(2-diethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol 1157856-56-8 C29H31NO4
5-[4-(2-diethylaminoethoxy)phenyl]-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-2,8-diol
—— Ethyl 3,4-dihydro-2-phenyl-2H-1-benzopyran-3-carboxylate 21763-08-6 C18H18O3
Ethyl 3,4-dihydro-2-phenyl-2H-1-benzopyran-3-carboxylate
—— 3'-hydroxy-7,8,4-trimethoxyflavonol 132594-07-1 C18H16O7
3'-hydroxy-7,8,4-trimethoxyflavonol
—— 7-decyl-3,2',3',5',6'-pentamethoxyflavone 1354708-28-3 C30H40O7
7-decyl-3,2',3',5',6'-pentamethoxyflavone
—— Apuleitrin 124909-81-5 C21H22O9
Apuleitrin
—— 2-[4'-(naphthalen-1-yl)]-phenyl-chromen-4-one 869559-79-5 C25H16O2
2-[4'-(naphthalen-1-yl)]-phenyl-chromen-4-one
—— methyl rac-2-(4-chloronaphthalen-1-yl)-4-oxochroman-3-carboxylate 1204754-74-4 C21H15ClO4
methyl rac-2-(4-chloronaphthalen-1-yl)-4-oxochroman-3-carboxylate
—— 8-Methoxy-2-o-anisyl-3-nitro-Δ<sup>3</sup>-chromen 57543-96-1 C17H15NO5
8-Methoxy-2-o-anisyl-3-nitro-Δ<sup>3</sup>-chromen
—— 2,5-dihydro-10-methoxy-5-(3-(2-(N,N-dimethylamino)ethyl)phenyl)-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline 239069-80-8 C30H34N2O2
2,5-dihydro-10-methoxy-5-(3-(2-(N,N-dimethylamino)ethyl)phenyl)-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinoline
—— isoorientin 28225-11-8 C21H20O12
isoorientin
—— 3-Methoxy-5-hydroxy-6,7;3',4'-bismethylendioxy-flavon 98251-27-5 C18H12O8
3-Methoxy-5-hydroxy-6,7;3',4'-bismethylendioxy-flavon
—— 70215-42-8 C94H82O24
—— (2R,3S,4S)-2,3-trans-3,4-trans-3-acetoxy-3',4',7-trimethoxy-4-(2,4,6-trimethoxyphenyl)flavan 69082-87-7 C29H32O9
(2R,3S,4S)-2,3-trans-3,4-trans-3-acetoxy-3',4',7-trimethoxy-4-(2,4,6-trimethoxyphenyl)flavan
—— 6-methyl-2-(4-methoxyphenyl)-4H-1-benzopyran-4-thione 140885-97-8 C17H14O2S
6-methyl-2-(4-methoxyphenyl)-4H-1-benzopyran-4-thione
—— 2,5-dihydro-9-hydroxy-10-methoxy-2,2,4-trimethyl-5-(3-(methylthiomethoxy)phenyl)-1H-[1]benzopyrano[3,4-f]quinoline 239070-53-2 C28H29NO4S
2,5-dihydro-9-hydroxy-10-methoxy-2,2,4-trimethyl-5-(3-(methylthiomethoxy)phenyl)-1H-[1]benzopyrano[3,4-f]quinoline
—— 4-nitro-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide 1467668-57-0 C24H20N2O9S
4-nitro-N-(4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzenesulfonamide
—— L-Proline, 1-[(2S)-3-[[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-4-yl]thio]-2-methyl-1-oxopropyl]-, methyl ester 2227330-50-7 C25H29NO9S
L-Proline, 1-[(2S)-3-[[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-4-yl]thio]-2-methyl-1-oxopropyl]-, methyl ester
—— 3-Hydroxy-5,6-dimethoxy-2-(3,4-dimethoxy-phenyl)-chromen-4-on 858801-50-0 C19H18O7
3-Hydroxy-5,6-dimethoxy-2-(3,4-dimethoxy-phenyl)-chromen-4-on
—— 3-hydroxy-7-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 109980-57-6 C20H20O8
3-hydroxy-7-methoxymethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one
—— 3-Chlor-2',5,7,8-tetramethoxyflavon 65095-84-3 C19H19ClO6
3-Chlor-2',5,7,8-tetramethoxyflavon
—— 8-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-hydroxyphenyl)-3-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]oxy]pyrano[4,3,2-de]-1-benzopyrylium 1263032-12-7 C40H35O15+
8-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-hydroxyphenyl)-3-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-I(2)-D-glucopyranosyl]oxy]pyrano[4,3,2-de]-1-benzopyrylium
—— 7-[(6-Deoxy-I(2)-L-mannofuranosyl)oxy]-5,6-dihydroxy-2-phenyl-4H-1-benzopyran-4-one 38533-37-8 C21H20O9
7-[(6-Deoxy-I(2)-L-mannofuranosyl)oxy]-5,6-dihydroxy-2-phenyl-4H-1-benzopyran-4-one
—— 3-acetoxy-2-(4-methoxy-phenyl)-6-methyl-chroman 851-80-9 C19H20O4
3-acetoxy-2-(4-methoxy-phenyl)-6-methyl-chroman
—— (2R,2'R,3R,3'R)-8,8'-methylenebis(5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-ol) 126716-10-7 C41H48O14
(2R,2'R,3R,3'R)-8,8'-methylenebis(5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-ol)
—— methyl (flavan-4α-thio)acetate 22986-01-2 C18H18O3S
methyl (flavan-4α-thio)acetate
—— 6,8-difluoro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4Hchromen-4-one 1441772-53-7 C18H14F2O6
6,8-difluoro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4Hchromen-4-one
—— 4'-benzyloxy-5-hydroxy-3',6,7,8-tetramethoxyflavone 1350827-34-7 C26H24O8
4'-benzyloxy-5-hydroxy-3',6,7,8-tetramethoxyflavone
—— (E)-7-methoxy-2-(4-methoxyphenyl)-4-(4-methoxystyryl)chroman 63524-14-1 C26H26O4
(E)-7-methoxy-2-(4-methoxyphenyl)-4-(4-methoxystyryl)chroman
—— 2-(3'-Acetyl-4'-hydroxy-4,5,2',6'-tetramethoxy-biphenyl-2-yl)-5,7-dimethoxy-chromen-4-one 100303-86-4 C29H28O10
2-(3'-Acetyl-4'-hydroxy-4,5,2',6'-tetramethoxy-biphenyl-2-yl)-5,7-dimethoxy-chromen-4-one
—— 4-[4-[11-(1-Adamantyloxy)-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]-10-yl]phenyl]morpholine 1278523-94-6 C63H67NO5
4-[4-[11-(1-Adamantyloxy)-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]-10-yl]phenyl]morpholine