2000 Fiscal Year Final Research Report Summary
Studies on the chemical-regulation of marine sessile organisms using phloroglucinol compounds from Eucalyptus sp
| Project/Area Number |
10660108
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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 |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Shizuoka University |
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Principal Investigator |
ETOH Hideo Shizuoka University, Faculty of Agriculture, Professor, 農学部, 教授 (10076747)
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| Co-Investigator(Kenkyū-buntansha) |
TERADA Yukimasa Meijo University, Faculty of Pharmacy, Associate Professor, 薬学部, 助教授 (20076756)
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| Project Period (FY) |
1998 – 2000
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| Keywords | Eucalyptus / phlorogulucinol / marine sessile organisms / sideroxyronal / attaching repellent / strcuture-activity relationship / biofouling substance |
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| Research Abstract |
In this research we had the following two results. 1) The synthesis of grandinal : We prepared grandinol by an alternate and improved procedurein three steps in 13% yield. Synthesis of the jensenone derivative was started 1,3,5-trimethoxybenzene. n isovaleryl group was readily introduced by a reaction with isovaleryl chloride. Reduction of the isovaleryl trimethoxybenzene with LAH and subsequent dehydration by irradiation in CHCl_3 gave the styrene compound. Further, the styrene compound was reduced by treatment with Pt2O under H2 atmosphere to yield the alkylbenzene. By aromatic bromination, adding ClCO_2Me, elimination, reduction and oxidation, the jensenone derivative was synthesized in nine steps in 13% overall yiels. Having successfull prepared the desired compounds, the jensenone derivative was subjected to Diels-Alder cycloaddition. The desired product in 14% yield and the regio isomer in 18% yield were given. Finally, the desired product was subjected to deprotection of the hydroxy groups with BBr_3S(Me)_2. We accomplished the first synthesis of grandinal. 2) Structure-activity relationship of phloroglucinol compounds. We discuss the structure-activity relationship of phloroglucinol compounds on the basis of molecular mechanics caluculations. When these compounds were superimposed on each other and the strongest inhibitor was applied as a template, the repulsion energy of the other compounds was proportional to the logarithmic attachment-inhibiting activity. It is concluded that, of the two phloroglucinol rings in sideroxylonal A, ring C is more important, and those compounds that stereo-chemically and electrostationally resemple the template molecule are more active.
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