60(P-35) Tricholoma属キノコから得られた新規テルペノイドtricholomalides A-Cの構造と神経突起伸展作用について(ポスター発表の部)

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Three new diterpenes, tricholomalides A-C (1-3), were isolated from the methanol extract of the fruiting body of Tricholoma sp. Their structures were elucidated on the basis of their spectral data. The absolute stereochemistry of 1 was determined by applying the octant rule to the positive Cotton effect observed at 302nm (Δε=+0.31) due to the cyclopentanone in 1. Compound 2 was converted to 1 during storage at 4℃ in DMSO. Thereby, the absolute configuration of 2 was established as 2S, 7S, 8S, 1OR and 14R. The CD spectra of 2 and 3 revealed the Cotton effects with the same signs for the respective peaks; 234 (Δε-0.22) and 344nm (Δε+0.16) for 3 and 250 (Δε-0.57) and 336nm (Δε+0.53) for 2, which were closely associated with the same conformational and substitutional effects on cisoid α,β-unsaturated ketones in 2 and 3. Consequently, the structure of 3 was determined including the absolute stereochemistry. Tricholomalides 1-3 significantly induced neurite outgrowth in rat pheochromocytoma cells (PC-12) at concentration of 100μM.
天然有機化合物討論会の論文
2003-09-01