RESUMO
An actinomycete strain designated as 4297 was isolated from a soil sample collected near Moscow. The strain produced a complex of two antibiotics. One of them had a broad antibacterial spectrum and, in terms of its physicochemical properties and X-ray structural evidence, was identified with griseoviridin. The other was active against gram-positive bacteria and, by its chromatographic comparison with an authentic sample, mass spectroscopic determination of the molecular weight and UV spectra, was identified with etamycin. The strain 4297 differed from the described cultures producing griseoviridin and etamycin. By the taxonomic features it was classified as belonging to Streptomyces albolongus.
Assuntos
Antibacterianos , Antibacterianos/biossíntese , Macrolídeos , Peptídeos , Streptomyces/metabolismo , Antibacterianos/química , Peptídeos Cíclicos/biossíntese , Peptídeos Cíclicos/químicaRESUMO
To identify the structure of virenomycin, a new antitumor antibiotic consisting of components V and M, its acetyl and permethyl derivatives, as well as products of acid methanolysis and their derivatives were obtained. The IR-, NMR- and mass-spectra of the above compounds are presented. Based on an analysis of the spectral data the structure of virenomycin is suggested.
Assuntos
Antibióticos Antineoplásicos , Fenômenos Químicos , Química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas/métodos , Metilglicosídeos , Espectrofotometria InfravermelhoRESUMO
Virenomycin, a new crystalline antitumor antibiotic was isolated from the mycelium of Streptomyces virens. The antibiotic contained: C 64.87 per cent, H 5.66 per cent, methoxylic groups 9.5 per cent. The melting temperature was 255-260 degrees (dec.), [alpha]20D=-17 (c 0.142, chloroform). Virenomycin had a complex UV spectrum with lambdamax. 245 (677), 265 (453), 275 (542), 287 (507), 395 (222) nm. A chromofor fragment and carbohydrate (C7H14O5) were found in the methanolysis products. Virenomycin was close to antibiotic c B-21085 BY THe physico-chemical properties and differed from it in the character of the UV spectrum and the values of the specific absorption, as well as by the optic rotation in dimethyl sulphoxide and acetic acid.
Assuntos
Antibióticos Antineoplásicos , Fenômenos Químicos , Química , Temperatura Alta , Dispersão Óptica Rotatória , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
The composition of virenomycin, a new antitumor antibiotic was studied. Two components V and M were detected with high resolution liquid chromatography and thin layer chromatography on siluphol (Czechoslovakia) and silica gel (Merk, BRD). A preparative method for separation of the antibiotic components with the use of chromatography on columns with silica gel was developed. Biological and physicochemical properties of separate components were studied to show that they significantly differed by their antibacterial action in vitro: virenomycin V was 2 to 4 times more active than virenomycin M against a number of microbes. The physicochemical properties of the components are similar. It was shown with mass spectrometry that the molecular weight of virenomycin is 12 units higher than that of virenomycin M. The PMR spectra showed that this difference is due to the presence of a vinyl group in the chromophore moiety of the virenomycin V molecule and a methyl group at the similar site of the virenomycin M molecule.