Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities
Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities
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DOI：
10.1021/jf990674x
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发表时间：
2000-02-01
影响因子：
6.1
通讯作者：
Kobayashi, A
中科院分区：
文献类型：
--
作者：
Sekiwa, Y;Kubota, K;Kobayashi, A
从生姜中分离得到两个新的6-姜二醇糖苷。经HRFAB-MS和NMR分析，确定其结构分别为1-（4-O-β-D-吡喃葡萄糖基-3-甲氧基苯基）癸烷（1）和5-O-β-D-吡喃葡萄糖基-3-羟基-1-（4-羟基-3-甲氧基苯基）癸烷（2）。用新鲜生姜制备的丙酮粉孵育这些糖苷后，通过HPLC证实它们已被水解为6-姜二醇。这一结果表明，这些葡萄糖苷是6-姜二醇的前体或中间体。要认识到他们的功能，他们的抗氧化活性进行了研究，并比较其苷元，6-姜二醇，亚油酸模型系统和DPPH自由基清除能力。虽然1没有显示任何活性，但2在两次测量中具有与糖苷配基一样强的活性。
Two novel glucosides of 6-gingerdiol were isolated from fresh ginger (Zingiber officinale Roscoe). Their structures were determined as 1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl decane (1) and 5-O-beta-D-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane (2) by HRFAB-MS and NMR analyses, and the absolute configurations of both aglycons were identified as (3S,5S) by a comparison with synthetic compounds. After incubating these glucosides with acetone powder prepared from fresh ginger, they were confirmed to have been hydrolyzed to 6-gingerdiol by HPLC. This result suggests that these glucosides are the precursors or intermediates of 6-gingerdiol. To recognize their function, their antioxidative activities were investigated and compared to that of their aglycon, 6-gingerdiol, by a linoleic acid model system and by their DPPH radical-scavenging ability. Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements.