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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,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl acetate 302917-68-6 C45H40O8
(2R,3S,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl acetate
—— 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,3-(phenylcarbamate), (2R-trans)- 71634-89-4 C22H19NO7
2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,3-(phenylcarbamate), (2R-trans)-
—— 2,3-trans-Flavan-3-yl-formiat 55539-37-2 C16H14O3
2,3-trans-Flavan-3-yl-formiat
—— (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-yl acetate 850816-10-3 C70H72O9
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-yl acetate
—— 5-acetoxy-2-(3-methoxy-phenyl)-chromen-4-one 6697-64-9 C18H14O5
5-acetoxy-2-(3-methoxy-phenyl)-chromen-4-one
—— 1401236-98-3 C44H39BrO5S
—— 3-(but-2-en-1-yl)-2-phenyl-4H-chromen-4-one 1514918-50-3 C19H16O2
3-(but-2-en-1-yl)-2-phenyl-4H-chromen-4-one
—— 2-(2,4-dibenzoyloxyphenyl)-5-hydroxy-7-(methoxymethoxy)-3-(3-methyl-2-buten-1-yl)-4H-chromen-4-one 1610962-21-4 C36H30O9
2-(2,4-dibenzoyloxyphenyl)-5-hydroxy-7-(methoxymethoxy)-3-(3-methyl-2-buten-1-yl)-4H-chromen-4-one
—— 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-methylpyrrolidine 1278523-64-0 C56H59NO5
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-methylpyrrolidine
—— 3-(phenylselanyl)-2-(m-tolyl)-4H-chromen-4-one 1332698-01-7 C22H16O2Se
3-(phenylselanyl)-2-(m-tolyl)-4H-chromen-4-one
—— 2-(3-Amino-4-methoxyphenyl)-3-bromo-5-hydroxy-6,7,8-trimethoxychromen-4-one 1175534-12-9 C19H18BrNO7
2-(3-Amino-4-methoxyphenyl)-3-bromo-5-hydroxy-6,7,8-trimethoxychromen-4-one
—— 8-{4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate 152735-66-5 CH4O3S*C31H34N2O3
8-{4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate
—— (E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one 1443276-28-5 C27H30O6
(E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
—— 6-Hydroxy-4'-(β-Δ<sup>α,β</sup>-butenolid)flavon 39679-69-1 C19H12O5
6-Hydroxy-4'-(β-Δ<sup>α,β</sup>-butenolid)flavon
—— 5,6-dihydroxy-3,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)chromen-4-one 124909-86-0 C25H22O8
5,6-dihydroxy-3,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)chromen-4-one
—— 4-Methoxy-7a-phenyl-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one 128814-91-5 C17H14O3
4-Methoxy-7a-phenyl-1a,7a-dihydro-1H-7-oxa-cyclopropa[b]naphthalen-2-one
—— 8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one 131402-10-3 C16H10BrFO2
8-bromomethyl-2-(3-fluorophenyl)-4H-benzopyran-4-one
—— kaempferol 3-O-β-D-glucopyranosyl(1->4)-[α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranoside 1187746-07-1 C33H40O20
kaempferol 3-O-β-D-glucopyranosyl(1->4)-[α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranoside
—— 2,8-bis-(4-methoxy-phenyl)-2,3,8,9-tetrahydro-pyrano[2,3-<i>f</i>]chromene-4,10-dione 72758-05-5 C26H22O6
2,8-bis-(4-methoxy-phenyl)-2,3,8,9-tetrahydro-pyrano[2,3-<i>f</i>]chromene-4,10-dione
—— 7-(4-dimethylamino-phenyl)-4-methoxy-6,7-dihydro-furo[3,2-<i>g</i>]chromen-5-one 73877-33-5 C20H19NO4
7-(4-dimethylamino-phenyl)-4-methoxy-6,7-dihydro-furo[3,2-<i>g</i>]chromen-5-one
—— 8-allyl-2-(2,6-difluorophenyl)-4H-benzopyran-4-one 131402-16-9 C18H12F2O2
8-allyl-2-(2,6-difluorophenyl)-4H-benzopyran-4-one
—— methyl (2S,3S,4S,5R,6S)-6-((2-(4-((((S)-1-(tert-butoxy)-1-oxopropan-2-yl)carbamoyl)oxy)phenyl)-5,6-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 1432474-21-9 C30H33NO15
methyl (2S,3S,4S,5R,6S)-6-((2-(4-((((S)-1-(tert-butoxy)-1-oxopropan-2-yl)carbamoyl)oxy)phenyl)-5,6-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate
—— 11-Cyclopentyloxy-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] 1278523-71-9 C56H58O6
11-Cyclopentyloxy-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]
—— (4-oxo-2-phenyl-chroman-6-yl)-acetic acid 101451-72-3 C17H14O4
(4-oxo-2-phenyl-chroman-6-yl)-acetic acid
—— 5-Hydroxy-6,8,8-trimethyl-2-phenyl-2,3,9,10-tetrahydro-8H-pyrano[2,3-f]chromen-4-one 116107-11-0 C21H22O4
5-Hydroxy-6,8,8-trimethyl-2-phenyl-2,3,9,10-tetrahydro-8H-pyrano[2,3-f]chromen-4-one
—— 4α,3',4'-trimethoxyflavan 88214-66-8 C18H20O4
4α,3',4'-trimethoxyflavan
—— 6-diphenylmethyl-5,7-dimethoxyflavone 103865-57-2 C30H24O4
6-diphenylmethyl-5,7-dimethoxyflavone
—— 4’-(1-hydroxy-2-isopropylaminoethyl)flavone 60324-55-2 C20H21NO3
4’-(1-hydroxy-2-isopropylaminoethyl)flavone
—— (flavon-4'-yl)methanol 700843-44-3 C16H12O3
(flavon-4'-yl)methanol
—— (2-Methyl-imidazo)-(4,5:6,7)-3-acetoxy-flavon 6587-10-6 C19H14N2O4
(2-Methyl-imidazo)-(4,5:6,7)-3-acetoxy-flavon
—— 5-hydroxy-7-methoxy-6,8-dimethylflavanone 55820-35-4 C18H18O4
5-hydroxy-7-methoxy-6,8-dimethylflavanone
—— 7-((4-methylbenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate 1254040-84-0 C27H22O7
7-((4-methylbenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate
—— [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[2-(2-fluorophenyl)acetyl]-3-hydroxyphenoxy]oxan-2-yl]methyl acetate 121060-06-8 C28H29FO12
[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[2-(2-fluorophenyl)acetyl]-3-hydroxyphenoxy]oxan-2-yl]methyl acetate
—— 2-(3,4-Bis-benzyloxy-phenyl)-3-butyl-5-hydroxy-6,7-dimethoxy-chromen-4-one 134082-33-0 C35H34O7
2-(3,4-Bis-benzyloxy-phenyl)-3-butyl-5-hydroxy-6,7-dimethoxy-chromen-4-one
—— 1,4,5,6-tetrahydro-1-(4-fluorophenyl)-6-methyl-3,6-diphenyl-pyrano[2,3-c]pyrazole 1242100-55-5 C25H21FN2O
1,4,5,6-tetrahydro-1-(4-fluorophenyl)-6-methyl-3,6-diphenyl-pyrano[2,3-c]pyrazole
—— (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-3-methylbutanoate 1158555-64-6 C25H27NO10
(S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-3-methylbutanoate
—— 1H-Cyclopenta[b]benzofuran-2-carboxylic acid, 6-[[(2R,3R,6R)-6-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-, methyl ester, (1R,2R,3S,3aR,8bS)- 960365-80-4 C48H50O13
1H-Cyclopenta[b]benzofuran-2-carboxylic acid, 6-[[(2R,3R,6R)-6-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-, methyl ester, (1R,2R,3S,3aR,8bS)-
—— Methyl-7,4'-dimethoxyflavon-6-carboxylat 37042-32-3 C19H16O6
Methyl-7,4'-dimethoxyflavon-6-carboxylat
—— [(2S,3S,4R,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-7-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxychromen-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate 1374991-37-3 C58H52O22
[(2S,3S,4R,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-7-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxychromen-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
—— 3,5-dihydroxy-6,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)chromen-4-one 124910-04-9 C25H22O8
3,5-dihydroxy-6,7-dimethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)chromen-4-one
—— 9‑(4‑chlorobenzoyl)‑2‑phenylpyrano[2,3‑f]chromene‑4,8‑dione 1372630-60-8 C25H13ClO5
9‑(4‑chlorobenzoyl)‑2‑phenylpyrano[2,3‑f]chromene‑4,8‑dione
—— (4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid pentyl ester 36556-14-6 C22H22O5
(4-oxo-2-phenyl-4H-chromen-7-yloxy)-acetic acid pentyl ester
—— kaempferol 4′-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside 1252558-73-8 C27H30O16
kaempferol 4′-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside
—— 5,7,3',4'-tetra-O-benzyl-3-O-acetyl-4β-allyl-catechin 919365-45-0 C48H44O7
5,7,3',4'-tetra-O-benzyl-3-O-acetyl-4β-allyl-catechin
—— di-tert-butyl ((4-(5,6-dihydroxy-4-oxo-7-(((2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-2-yl)phenoxy)carbonyl)-L-aspartate 1432474-25-3 C35H41NO17
di-tert-butyl ((4-(5,6-dihydroxy-4-oxo-7-(((2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-2-yl)phenoxy)carbonyl)-L-aspartate
—— Tetra-O-acetyl-axillarin 24160-92-7 C25H22O12
Tetra-O-acetyl-axillarin
—— 4-(2-bromophenyl)-2-phenyl-2H-benzo[h]chromene 1193311-07-7 C25H17BrO
4-(2-bromophenyl)-2-phenyl-2H-benzo[h]chromene
—— [4-(3,5-diacetyloxy-6,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate 23494-51-1 C24H22O11
[4-(3,5-diacetyloxy-6,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate
—— 4'-7-di-O-benzylquercet-3-yl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 130999-24-5 C40H36O14
4'-7-di-O-benzylquercet-3-yl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
—— 8-allyl-2-(4-fluorophenyl)-4H-benzopyran-4-one 131402-14-7 C18H13FO2
8-allyl-2-(4-fluorophenyl)-4H-benzopyran-4-one