Antioxidant and free radical scavenging activity of flavonol glycosides from different Aconitum species

Antioxidant and free radical scavenging activity of flavonol glycosides from different Aconitum species
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DOI:
10.1016/s0378-8741(03)00043-6
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发表时间:
2003-05-01
影响因子:
5.4
通讯作者:
De Tommasi, N
De Tommasi, N
中科院分区:
医学2区
文献类型:
--
作者:
Braca, A;Fico, G;De Tommasi, N

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通过1,1 -二苯基-2-二苦肼基(DPPH)自由基清除试验对一些意大利藜属物种(A.黑刺蛾亚种tauricum,A.黑刺蛾亚种neomontanum、新蒙塔木A. paniculatum,A. vulparia)导致13个黄酮醇糖苷的分离:槲皮素3-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(1-> 2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside(1),山奈酚3-O-(6-反式-咖啡酰基)-β-吡喃葡萄糖基-(1 - 2)-β-吡喃葡萄糖苷-7-O-α-吡喃鼠李糖苷(2),槲皮素3-O-(6-trans-p-coumaroyl)-beta-glucopyranosyl-(1-> 2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside(3),山奈酚3-O-(6-反式-β-香豆酰基)-β-吡喃葡萄糖基-(1 → 2)-β-吡喃葡萄糖苷-7-O-α-吡喃鼠李糖苷(4),槲皮素7-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(1-> 3)-alpha-rhamnopyranoside-3-O-beta-glucopyranoside(5),山奈酚7-O-(6-反式-咖啡酰基)-β-吡喃葡萄糖基-(1 - 3)-α-吡喃鼠李糖苷-3-O-β-吡喃葡萄糖苷(6),山奈酚-7-O-(6-反式-对-香豆酰基)-β-吡喃葡萄糖基-(1 - 3)-α-吡喃鼠李糖苷-3-O-β-吡喃葡萄糖苷(7),山奈酚3-O-β-(2”-乙酰基)吡喃半乳糖苷(8),山奈酚3-O-β-(2”-乙酰基)吡喃半乳糖苷-7-O-alpha-阿拉伯吡喃糖苷(9),槲皮素3-O-beta-(2”-乙酰基)吡喃半乳糖苷-7-O-α-吡喃阿拉伯糖苷(10),槲皮素3,7-二-O-α-吡喃鼠李糖苷(11),山奈酚3,7-二-O-α-吡喃鼠李糖苷(12)和槲皮素3-O-β-吡喃葡萄糖苷-7-O-α-吡喃鼠李糖苷(13)。通过DPPH法测定其清除自由基的能力,并通过β-胡萝卜素和亚油酸的氧化偶联法测定其抗氧化活性。结果表明,化合物5在DPPH自由基清除试验中是最有活性的化合物(IC 50 1.9 μ M),而在β-胡萝卜素和亚油酸的偶联氧化试验中,化合物1在1小时后具有最高的抑制率(58.9%)。得到了AA的构效关系。(C)2003爱思唯尔科学爱尔兰有限公司保留所有权利。
Bioassay-guided fractionation by 1, 1 -diphenyl-2-dipicrylhydrazyl (DPPH) radical scavenging test of polar extracts of some Italian Aconitum species (A. napellus subsp. tauricum, A. napellus subsp. neomontanum, A. paniculatum, A. vulparia) led to the isolation of 13 flavonol glycosides: quercetin 3-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(I --> 2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (1), kaempferol 3-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(I --> 2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (2), quercetin 3-O-(6-trans-p-coumaroyl)-beta-glucopyranosyl-(I --> 2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (3), kaempferol 3-O-(6-trans-p-coumaroyl)-beta-glucopyranosyl-(1 --> 2)-p-glucopyranoside-7-O-alpha-rhamnopyranoside (4), quercetin 7-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(I --> 3)-alpha-rhamnopyranoside-3-O-beta-glucopyranoside (5), kaempferol 7-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(I --> 3)-alpha-rhamnopyranoside-3-O-beta-glucopyranoside (6), kaempferol 7-O-(6-trans-p-coumaroyl)-beta-glucopyranosyl-(I --> 3)-alpha-rhamnopyranoside-3-O-beta-glucopyranoside (7), kaempferol 3-O-beta-(2"-acetyl)galactopyranoside (8), kaempferol 3-O-beta-(2"-acetyl)galactopyranoside-7-O-alpha-arabinopyranoside (9), quercetin 3-O-beta-(2"-acetyl) galactopyranoside-7-O-alpha-arabinopyranoside (10), quercetin 3,7-di-O-alpha-rhamnopyranoside (11), kaempferol 3,7-di-O-alpha-rhamnopyranoside (12) and quercetin 3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (13). Their antioxidant activity (AA) was determined by measuring free radical scavenging activity by DPPH test and the coupled oxidation of beta-carotene and linoleic acid assay. The results showed that 5 is the most active compound in the DPPH free-radical scavenging test (IC50 1.9 muM) while in the coupled oxidation of beta-carotene and linoleic acid assay compound 1 has the highest inhibitory ratio after I h (58.9%). Some structure-activity relationships on the AA were obtained. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.