11 塩基性配糖体抗生物質,Sporaviridinの単離と構造

概要

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Sporaviridins (SVD) are basic glycoside antibiotics produced by Streptosporangium viridogriseum. They exhibit strong inhibitory activity against Gram-positive bacteria, acid-fast bacteria and trichophyton. We have already reported on the structural determination of the three constituent pentasaccharides (viridopentaose A, B and C) of N-acetylsporaviridins (N-Ac-SVD). Recently, we succeeded in the isolation of major components and the structure elcidation of N-Ac-SVD. N-Ac-SVD are composed of six components (N-Ac-SVD-A_1, A_2, B_1, B_2, C_1 and C_2) whose molecular weights are all about 2200. Treatment of each component of N-Ac-SVD with DBU gave two pseudoaglycones (N-Ac-pAG-U and L) and one of three viridopentaoses. These pseudoaglycones are an epimeric pair with respect to C-13 and have still two sugar moieties (D-glucose and N-acetyl-L-vancosaminide). A variety of degradative reactions and spectroscopic analyses of N-Ac-pAG-U and L showed that the aglycone moieties are 34-membered polyol macrocyclic lactone with a hemiketal system and three double bonds including a conjugated diene. Finally, the total structures of N-Ac-SVD were determined as shown in Fig. 1.
天然有機化合物討論会の論文
1986-09-09