1994 Fiscal Year Final Research Report Summary
STUDY OF LARGE-SCALE SYNTHESIS OF PHOSPHOLIPID HYDROPEROXIDE BY UTILLIZING ENZYMES
| Project/Area Number |
04556015
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
製造化学・食品
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| Research Institution | OKAYAMA UNIVERSITY |
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Principal Investigator |
BABA Naomichi Okayama University Faculty of Agriculture Professor, 農学部, 教授 (50027075)
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| Co-Investigator(Kenkyū-buntansha) |
SHIMIZU Sakayu Kyoto University Faculty of Agriculture Professor, 農学部, 教授 (70093250)
MATSUO Mitsuyoshi Tokyo Metropolitan Department of Biology Director Institute of Gerontology, 老化科学技術研究系, 部長 (20072986)
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| Project Period (FY) |
1992 – 1994
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| Keywords | hydroperoxide of phospholipid / hydroperoxide of phosphatidylcholine / hydroperoxide of phosphatidylethanolamide / hydroperoxide of phosphatidylglycerol / hydroperoxide of phosphatidylserine / endotherial cell of human / hydroperoxide, toxicity of / phospholipid hydroperoxide, synthesis of |
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| Research Abstract |
In the project term of 1992, the large scale hydroperoxidation of unsaturated fatty acid using soybean lipoxigenase was established. The hydroperoxy group was successfuly protected as dimethylperacetal and the ester was hydrolyzed to afford a key peroxyfatty acid (POA). Optically active Lyso-PC was prepared via short route synthesis using lipase in organic solvent. This Lyso-PC was esterified with POA using DCC and DMAP in chloroform. Removing the peracetal group under the mild conditions afforded one of our desired phospholipid hydroperoxide (PC-OOH). During this process, the stability of the hydroperoxy group could be kept intact when it was stored at-20ﾟC in the presence of BHT under nitrogen. The study on the toxicity of PC-OOH against cultured human endotherial cells was started by Dr.Matsuo. Unsaturated fatty acids produced by fermentation were provided by Prof. Shimizu. In 1993, starting from PC-OOH having hydroperoxyfatty acyl group from arachidonic acid, PG-OOH,PE-OOH and PS-OOH were synthesized by employing phospholipase D from cabbage or Steptomyces species. As an another study in this year, synthesis of PI-OOH was commenced using hog pancreatic phospholipase A2 (PLA2)-catalyzed acylation of lyso-PI and it was carried over next year. In 1994, synthesis of PC-OOH having hydroperoxyfatty acyl group from docosahexaenoic acid (DHA) was addressed. A problem, however, arised. Different from linoleic and arachidonic acids, DHA was hard to be esterified by diazomethane. Other reagent like DDC or HCI-MeOH could not be used due to the instability of OOH group under these conditions. The study is continuing at present. The reaction condition for PLA2-catalyzed acylation of Lyso-PG was found and the further study will be continued. Finally, Dr.Matsuo revealed for the first time that PC-OOH was found to be not so toxic against cultured human endotherial cells. This interesting finding may help develop further a number of relating studies in future.
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