1991 Fiscal Year Final Research Report Summary
Chiral Synthesis and Biological Activities of Allelopathic Dihydropyranones having Multi-functional Structures.
| Project/Area Number |
02660127
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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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 | Tohoku University |
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Principal Investigator |
SUGIYAMA Takeyoshi Tohoku Univ. Agric. Chem. Assistant, 農学部, 助手 (10125586)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Aspyrone / Chiral synthesis / Phomopsolide B / Allelopathic metabolites / Biologicallu active dihydropyranones / 生物活性ジヒドロピラノン類 |
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| Research Abstract |
1. Aspyrone : Aspyrone, an antibiotic isolated from the culture broth of Aspergillus species and having a characteristic structural feature arising from the skeletal rearrangement on its biosynthetic pathway, was elaborated in an optically pure form by the key reaction involving a highly disstereospecific addition of delta-lactone enelate to 2-tosylow-aldehyde and a subsequent in situ formation of epoxide. Spectroscopic and physical constants of synthetic aspyrone were quite identical with those of natural one.
2. Phomopsolide B : Phomopsolide B, isolated as metabolite of Phomopsis oblongs and, having anti-boring and anti-feeding activities against the elm bark beetle, was synthesized in optically pure form from D-glucose and propargyl alcohol derivative. Synthetic phomopsoide B showed physical constants comparable with those of natural one and good agreement with respect to ^1H-NMR and IR spectera.
3. Biological Activities : Aspyrone is known to exhibit broad and rather weak antibiotic activities against bacteria. The synthetic aspyrone and its t-butyldimethylsilyl ether showed only weak antibiotic activity against Pyricularia oryzae.
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