| Project/Area Number |
04453030
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
天然物有機化学
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| Research Institution | HOKKAIDO UNIVERSITY |
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Principal Investigator |
NAKAMURA Hideshi HOKKAIDO UNIVERSITY, DEPARTMENT OF CHEMISTRY, ASSOCIATE PROFESSOR, 理学部, 助教授 (90217878)
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| Project Period (FY) |
1992 – 1993
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| Project Status |
Completed (Fiscal Year 1993)
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| Budget Amount *help |
¥4,700,000 (Direct Cost: ¥4,700,000)
Fiscal Year 1993: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1992: ¥3,600,000 (Direct Cost: ¥3,600,000)
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| Keywords | SYMBIOTIC ALGAE / ZOOXANTHELLA / ZOOXANTHELLATOXIN / STRUCTURE DETERMINATION / 62員環ラクトン / アプリシアトキシン / スピロアセタール / ゴニオラックス / ゴニオール |
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| Research Abstract |
Vasoconstrictive compounds, zooxanhtellatoxin-A (ZT-A) and ZT-B were isolated from a symbiotic marine dinoflagellate Symbiodinium sp. Sodium periodate oxidation of Zt-A followied by sodium borohydride reduction gave fragments containing characteristic functionalities including an exomethyoene, a diexpoxide, a sulfate, a conjugated diene, a spiroacetal, and an amide. The structures correspond to about 80% of the full structure of ZT-A.TOCSY spectra of ZT-A under various conditions enable us to connect the partial structures deduced from the degradation products. The unveiled structures were obtained by detailed analyes of HMBC, HMQC and 13-C NMR spectra. The structure of ZT-A was determined on the basis of the spectral data and chemical degradation experiments to be a novel 62-membered lactonewith and amide linkage.
Model compounds of tumor-promorting sabstance, aplysiatoxin were designed on the basis of the structure-activity relationship. Synthesis of a model containing functionalities essential for biological activity was finally achieved.
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