Structure of aerugine from Pseudomonas aeruginosa

A new optically active phenolic alkaloid with the composition C₁₀H₁₁NO₂S, mp 85–88°C, []_D +28° (c 1.0; chloroform) (I) has been isolated from the microorganismPseudomonas aeruginosa (strain 590) and has been called aerugine. The action of diazomethane gave an O-methyl derivative (II). On the basis of the formation of ortho-cresol by the hydrogenolytic desulfuration reaction, a study of the IR, mass, and PMR spectra and (I) and its acetyl derivative (III), and also the¹³C NMR spectrum of (I), the structure of 4-hydroxymethyl-2-(o-hydroxyphenyl)-2-thiazoline has been established for aerugine. The spectral characteristics of the compounds mentioned are given.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 553–558, July–August, 1987.