Formation, Isolation and Characterization of Trehalose Dimycolates from Rhodococcus erythropolis Grown on n-Alkanes

Abstract

Rhodococcus erythropolis DSM 432 15 produced a surface-active trehalose lipid whose formation was induced by n-alkanes to a maximum of 2.1 g 1-1 in a 50 1 batch culture on 2% (w/v) n-alkanes of chain length C13 to CIS. The glycolipid was extracted from the biomass with n-hexane and was purified by repeated chromatography on silica gel. It contained aptrehalose as the sole non-reducing sugar. The lipid moiety was characterized by 13C nuclear magnetic resonance spectroscopy and mass spectrometry and consisted predominantly of saturated long-chain a-branched P-hydroxy fatty acids (mycolic acids) ranging from C32H6403 to C38H7603, of which C34H,80, and C35H7003 predominated. The molar ratio of trehalose to mycolic acids was 1 : 2. 13C nuclear magnetic resonance analysis of the 0-hexamethyltrehalose obtained by saponification of the permethylated trehalose dimycolates revealed, with the aid of deuterium exchange, that the ester linkages of mycolic acids are to both primary alcohol groups at the C-6 and C-6' positions of the trehalose.

Structure and Characterization of Flavolipids, a Novel Class of Biosurfactants Produced by Flavobacterium sp. Strain MTN11

“…This is high compared to those of other biosurfactants. For example, glycolipid CMC values range from 27 to 40 mg/ liter for rhamnolipid (5,59) and from 4 to 15 mg/liter for trehalose lipid (19,44), depending on the surfactant components present. For the lipoproteins, CMC values for lichenysin range from 10 to 30 mg/liter (18,23,58), and for surfactin, iturin, and fengycin, reported CMC values are 10, 20, and 11 mg/liter, respectively (12).…”

Distribution of Biosurfactant-Producing Bacteria in Undisturbed and Contaminated Arid Southwestern Soils

“…One major class of biosurfactants is the glycolipids, which includes rhamnolipids, trehalose lipids, and sophorose lipids. Rhamnolipids are produced only by P. aeruginosa (30,33); trehalose lipids are produced only by a number of closely related genera, including Rhodococcus, Nocardia, Corynebacterium, Tsukamurella, Gordonia, Mycobacterium, and Arthrobacter, all belonging to the Firmicutes division (3,12,31,44); and sophorose lipids are produced by several species of Candida (14,15,22). A newly identified glycolipid group called mannosylerthritol lipids are produced by Candida and Ustilago maydis (25,26,51).…”

Effects of lipids on n-alkane attenuation in media supporting oil-utilizing microorganisms from the oily Arabian Gulf coasts

“…It is not surprising that hydrocarbon-utilizing microorganisms accumulate lipids readily. Such microorganisms are provided with hydrophobic envelopes that make them bind easily to hydrophobic compounds [14,15]. It has been suggested that a high cell lipid content is necessary for the uptake of hydrocarbons [16,17].…”