12 赤潮生物Pyrmnesium parvumの毒prymnesinの構造研究(口頭発表の部)

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Prymnesium parvum is a notorious red tide organism belonging to Haptophyceae. The flagellate causes serious damages to aquaculture and marine ecology in many parts of the world. In recent years the threat is most significant to salmon culture in Norway. Despite effort of many research groups. the causative ichthyotoxin named prymnesin has never been purified successfully. Hence chemical and toxicological studies of the toxin have been hampered. Recently we have succeeded for the first time to isolate two hemolytic-ichthyotoxic substances, named prymnesin-1 (PRM1) and prymnesin-2(PRM2). Their hemolytic potencies exceeded that of plant saponin more than 1000 times. FAB-MS data on molecular ion species and their isotope distribution pattern containing ^<35>Cl and ^<37>Cl allowed us to deduced a molecular formula C_<107>H_<154>O_<44>NCl_3 for PRM1 and C_M<96>H_<136>O_<35>NCl_3 for PRM2. ^<13>C NMR(BBD, DEPT) measurement on ^<13>C enriched PRM2 N-acetate indicated 96 carbon signals (2-methyls, 24-methylenes, 10-olefinic methines, 53-other methines and 7-quaternary carbons). Further detailed analyses of both ^1H-NMR (COSY, HOHAHA, NOESY) and ^1H observed ^1H-^<13>C correlation NMR (HSQC, HMBC) data disclosed for the first time the unprecedentedly unique structure of PRM2. The molecule is characterized by the 14 ether rings (6/6/6/7/6, 6/6, 6, 6/6, 6/6, 6), polyene-polyine bonds, three chlorine and one nitrogen atoms, and one pentose. Structural confirmation was further made by measuring NMR spectra of PRM2, the N-acetate, and per-acetate in two different solvents. PRM1 probably has additional one pentose and one hexose to the PRM2 skeleton.
天然有機化合物討論会の論文
1994-09-20

12 赤潮生物Pyrmnesium parvumの毒prymnesinの構造研究(口頭発表の部)

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