78 Azalomycin F_4の構造

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Azalomycin F-complex produced by Streptomyces hygroscopicus var. azalomyceticus exhibits a wide antibiotic activity and is efficacious against bacteria, yeast, fungi and protozoa. The structure of Azalomycin F4a, a main component of the F-complex, was studied. Azalomycin F4a (1) was obtained as microscopic needles from MeOH-H_2O, mp 131-132°(dec.), [α]_D +39°, UV λ^<EtOH>_<max>. nm ( log ε) ; 207 (4.11), 240 (4.58), 268 (4.36). Its molecular formula, C_<56>H_<95>O_<17>N_3 (M^+=1081), was determined from its spectroscopic and elemental analysis data. F4a (1) was subjected to a variety of chemical degradations to give a number of fragments. The chemical properties and spectroscopic data of 1 and the fragments allowed to elucidate the skeletal structure as shown in Fig. 1, particularly by the aid of extensive decoupling techniques on 400MHz ^1H- and 100MHz ^<13>C-NMR spectrometers and of field desorption mass spectrometry. Since ^<13>C-NMR spectrum of F4a showed no peak due to ketonic carbon but a hemiketal carbon peak, C(17) ketone group in 1 should be formed a hemiketal presumably with a hydroxy group at C(21). Azalomycin F4a was found to be a new 36-membered polyenic and polyhydroxy lactone which belongs biogenetically to a group of polyene macrolide antibiotics.
天然有機化合物討論会の論文
1980-09-10