47 Streptomyces albonigerの気菌糸誘導物質Pamamycin-607の単離と構造

概要

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Actinomycetes produce a number of useful antibiotics. The productivity of some antibiotics was recently shown to be closely correlated to the cell differentiation of actinomycetes, such as aerial mycelium formation and sporulation. We have isolated an aerial mycelium-inducing substance, named pamamycin-607, from the cultured material of Streptomyces alboniger, a puromycin producer, and its structure elucidated by means of spectral analysis. The physicochemical properties of pamamycin-607 are colorless oil, C_<35>H_<61>NO_7(HR-MS obsd. m/z 607.4462, error 1.4), [α]^<33>_D+22.8°(c=0.26, MeOH), UVλ^<MeOH>_<max> 215 nm (ε470), IRν^<CHCl_3>_<max> 1740 cm^<-1> (-O-CO-). The structure elucidation of pamamycin-607 was carried out mainly on its trifluoroacetic acid salt that was extensively analyzed by ^1H and ^<13>C NMR, 500 MHz 2D NMR spectra (^1H-^1H and ^1H-^<13>C shift correlation 2D and 2D-J spectra) with the aid of proton spin decoupling and NOE difference spectra. The structure of pamamycin-607 with the relative stereochemistry has thus been elucidated as shown in Fig. 1. The proposed structure seems to be a novel ionophore compound with a 16-membered macrodiolide ring having a dimethylamino side chain. Pamamycin-607 induced the aerial mycelium formation at 0.1 μg/disc to the aerial mycelium negative strain of Streptomyces alboniger.
天然有機化合物討論会の論文
1985-09-07