Iridoid glucosides with free radical scavenging properties from Fagraea blumei

Iridoid glucosides with free radical scavenging properties from Fagraea blumei
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DOI:
10.1002/hlca.19970800411
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发表时间:
1997-01-01
影响因子:
1.8
通讯作者:
Dyatmiko, W
Dyatmiko, W
中科院分区:
化学4区
文献类型:
--
作者:
Cuendet, M;Hostettmann, K;Dyatmiko, W

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从苦荞麦(Fagraea blumei G.don)茎皮甲醇提取物中分离得到4个新环烯醚萜糖苷1-4,命名为Bumeoside A-D。(马钱科)。伴随它们的是苯甲醇衍生物二-O-甲基胸苷(5)和黄酮类C-葡萄糖苷swertisin(6)。1-4的结构经FAB-MS、H-1-和C-13-核磁共振谱及碱解等方法确证。Blumeoside A(1)和C(3)分别为10-O-(2,5-二羟基对苯二甲酸)阿多糖酸和10-O-(2-羟基对苯二甲酸)阿多糖酸。在Blumeoside B(4)和D(2)中,对苯二甲酸部分的两个羧基都被adoxosidiic酸单元酯化。Blumeoside A-D(1-4)可抑制烷氧基引起的西红花碱漂白。在薄层色谱、自显影和分光光度分析中,蓝莓皂苷A(1)和D(2)对2,2-二苯基-1-苦基肼(DPPH)也具有清除作用。
Four new iridoid glucosides 1-4, named blumeosides A-D, were isolated From the methanolic stem-bark extract of Fagraea blumei G. DON. (Loganiaceae). They were accompanied by the benzyl-alcohol derivative di-O-methylcrenatin (5) and the flavone C-glucoside swertisin (6). The structures of 1-4 were established by spectroscopic methods, including FAB-MS, and H-1- and C-13-NMR, and by alkaline hydrolysis. Blumeosides A (1) and C (3) are 10-O-(2,5-dihydroxyterephthalo)adoxosidic acid and 10-O-(2-hydroxyterephthalo)adoxosidic acid, respectively. In blumeosides B (4) and D (2), both carboxylic groups of the terephthalic-acid moiety are esterified by adoxosidic-acid units. Blumeosides A-D (1-4) inhibited bleaching of crocin induced by alkoxyl radicals. Blumeosides A(1) and D(2) also demonstrated scavenging properties towards the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic and spectrophotometric assays.