Glucose and trehalose mycolates of a Rhodococcus sp. strain: isolation, structure and effect on mitochondrial respiration
K. Yu. Gordeev, V. A. Nenashev, V. N. Morgunova, N. V. Demidova, T. A. Tsotsoriya, G. Ya. Daraseliya, S. G. Batrakov
Research Laboratory of Biologically Active Substances of Hydrobionts, Ministry of PublicHealth of the USSR, Moscow; Institute of Biochemistry of Plants, Academy of Sciences of the Republic Georgia, Tbilisi
Abstract: The cell lipids of Rhodococcus sp. (Mycobacterium rubrum VKM V-874 var. 44) contain a fraction of acylated sugars consisting of 6,6'-di- and 6-mono-O-mycoloyl-α,α-D-trehaloses and 6-O-mycoloyl-D-glucopyranose. At the stationary growth phase they account for 1.4, 11.4 and 5.7%, respectively, of the total extractable lipids. Among the mycoloyl residues of these glycolipids, predominant molecular species have 40, 42, 44 and 46 carbon atoms, saturated C10, C12 and C14 side α-chains and a double bond located in the main chain at 9th, 11lth, 13th, 15th or 17th carbon atom from the terminal methyl group. All the glycolipids affect electron transport in mitochondria in vitro, which is manifested in decoupling oxidation from phosphorylation, retarding mitochondrial respiration in the presence of NADH-linked substrates but accelerating it in the presence of succinate (with rotenone) without of phosphoryl acceptor, as well as in loss of the respiratory control. In this respect 6-O-mycoloyl-D-glucopyranose differs substantially from the related methyl glycosides previously studied by other authors.
Russian Journal of Bioorganic Chemistry 1991, 17 (9):1258-1272