85 Aspergillus niger NH-401株の生産する新規抗菌性物質antafumicin AとBの構造と合成(ポスター発表の部)

概要

論文の詳細を見る
Novel antifungal substances, antafumicin A and B, were isolated from the potato-sucrose-agar plate culture of Aspergillus niger NH-401 (90mm 0, 500 plates, at 27℃, dark, 10 days). The structures of antafumicin A and B were elucidated by the spectrometric and single crystal X-ray analysis, and determined to be (4S)- and (4R)-(3-acetyl-2,6-dihydroxyphenyl)-(2R)-methoxy-4-butanolide, respectively. The absolute structures were concluded based on the synthetic studies: Using (S)-malic acid as the optically active starting material, (2S)-antafumicin A and B were synthesized, where C-C bond formation between benzene ring moiety and γ-lactone moiety by aldol condensation was a key step. Synthetic antafumicin A and B gave the identical physicochemical data (mp, IR, MS, ^1H- and ^<13>C-NMR) with those of the natural compounds except for optical rotation, thus indicating that the natural compounds are (2R)-isomers. The mixture of natural antafumicins almost completely inhibited the spore germination of the phytopathogenic fungi, Colletotrichum lagenarium, Fusarium oxysporum and Botrytis cinerea, at the concentration of 30ppm. The mixture also inhibited the growth of such bacteria as Bacillus subtilis, Escherichia coli and Aeromonas liquefaciens by about 50% at 50ppm.
天然有機化合物討論会の論文
1993-09-10