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二异亚丙基甘露醇的合成及其抑菌和抑制葡萄糖苷酶活性
詹天荣, 郑 立, 陈海敏, 宋金明
中国科学院海洋研究所
摘要:
以海带中提取的活性物质D-甘露醇与丙酮为原料合成了二异亚丙基甘露醇, 对其抑菌和抑制葡萄糖苷酶的生理活性进行了研究。结果表明, 合成的产物结构经红外光谱、核磁共振氢谱和碳谱分析证实为二异亚丙基甘露醇, 标题化合物对G+Staphylococcus aureusBacillus utilis都有一定的抑制作用, 最小抑制浓度均为100mg/ml, 对G+ Escherichia coli没有抑制作用;而且对α-葡萄糖苷酶也有抑制作用, 其IC50值为3.13μmol/ml。
关键词:  二异亚丙基甘露醇,合成,抑菌活性,抑制α-葡萄糖苷酶
DOI:10.11693/hyhz200305013013
分类号:
基金项目:国家杰出青年科学基金资助项目,49925614;中国科学院方向性创新项目,KZCX3-SW-215号
SYNTHESIS OF DI-O-ISOPROPYLIDENE-D-MANNITOL AND THE ASSOCIATED ANTIBACTERIAL ACTIVITIES AND INHIBITING GLUCOSIDASE
ZHAN Tian-Rong, ZHENG Li, CHEN Hai-Min, SONG Jin-Ming
Institute of Oceanology, The Chinese Academy of Sciences
Abstract:
Using D-mannitol extracted from Laminaria japonica and seaweed as raw materials, after being acetalated with acetone, di-o-isopropylidene-D-mannitol, a kind of important chiral synthpon and chiral precursor and intermedium, was prepared. The good productivity is 48.6% and its melting point is 114—115℃. The goal resultant datum (GR) of IR, 1H-NMR and 13C-NMR were obtained. The structure of GR was confirmed to be the same as di-o-isopropylidene-D-mannitol. In addition, preliminary pharmacological activity tests about antibacterial activities and inhibitingα-glucosidase showed that title compound had certain inhibiting effect on Staphylococcus aureus and Bacillus utilis, and their minimal inhibitory concentrations (MIC) were both 100mg/ml; however, it had no inhibition on Escherichia coli. Moreover, dio-isopropylidene-D-mannitol had an inhibiting effect on α-glucosidase, and its IC50 is 3.13μmol/ml. That inhibiting effect was not strong enough, because there is neither imino group nor heterocyclic including imino group, except for only two-hydroxy in the structure of di-o-isopropylidene-D-mannitol. Hence, the sample molecule is perhaps combined with two-methylene of the activity center ofα-glucosidase, and competed to inhibit the action of α-glucosidase with the other substances.
Key words:  Di-o-isopropylidene-D-mannitol, Synthesis, Antibacterial activities, Inhibiting α-glucosidase
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