2001 Fiscal Year Final Research Report Summary
A Study on New BioactiveProstanoids fromthe Okinawan Soft Coral
| Project/Area Number |
12680601
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | Tokyo University of Pharmacy and Life Science |
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Principal Investigator |
KAZUO Iguchi Tokyo Univ.of Pharm.& Life Sci.,School of Life Sci.,Professor, 生命科学部, 教授 (50057345)
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| Project Period (FY) |
2000 – 2001
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| Keywords | Marine Natural Products / Halogenated Prostanoids / Soft Coral / Clavularia viridis / Structure Determination / Tricycloclavulone / Synthesis / Biological Activity |
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| Research Abstract |
This research has been carried out in order to find new bioactive marine prostanoids from the Okinawan soft coral and to synthesize the prostanoid-related compounds.
The MeOH extract of the soft coral Clacularia viridis, collected on the coral reef of Ishigaki Island (Okinawa prefecture, Japan), was partitioned between AcOEt and H2O. The AcOEt soluble portion was repeatedly chromatographed to isolate 22 halogenated prostanoids as minor components. Among these prostanoids, 20 compounds were found to be unpreceedented. The structures of these halogentated prostanoids involving stereo-chemistry were determined based on the spectroscopic (NMR, IR, UV, MS, CD) and chemical transformations. One of these halogenated prostanoids showed a growth-inhibitory activity toward tumor cells. Stereoselective total synthesis of tricycloclavulone, a prostanoid-related compound with an unique structural feature isolated from Clacularia viridis, was also studied. The Lewis-acid catalyzed [2+2] ring formation gave the intermediate having the B/C ring system of tricyclo clavulone. The ring-closing metathesis reaction of the divinyl compound obtained from the above intermediate constructed the tricyclic ring system (A/B/C ring) of tricycloclavulone.
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Research Products
(2 results)
