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A Novel Fatty Acid, 12,17‐Dimethyloctadecanoic Acid, from the Extremophile Thermogemmatispora sp. (Strain T81)
Author(s) -
Vyssotski M.,
Ryan J.,
Lagutin K.,
Wong H.,
Morgan X.,
Stott M.
Publication year - 2012
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-012-3668-z
Subject(s) - fatty acid , pentadecanoic acid , strain (injury) , stereochemistry , chemistry , biochemistry , biology , anatomy
Abstract The major fatty acids of a novel species of Thermogemmatispora sp. (strain T81) from the phylum Chloroflexi were identified as i 18:0 (42.8 % of total fatty acids), i 19:0 (9.7 %), and i 17:0 (5.9 %). Also observed was a number of unidentified fatty acids, including a major acid (16.3 %) with ECL of 19.04 (BP1), and 18.76 (TG‐WAXMS A). GCMS revealed that this compound is a saturated 20‐carbon atom fatty acid. 1 H– and 13 C–NMR, with 1 H– 1 H–COSY and 1 H– 13 C–HSQC experiments suggested the structure of dimethyl octadecanoic acid with iso ‐branching, and an extra middle‐chain methyl group. A pyrrolidide derivative demonstrated the characteristic gaps in GCMS indicating methyl branching at C12 and C17, which was eventually confirmed by a 1 H– 13 C–HSQC–TOCSY experiment. This 12,17‐dimethyloctadecanoic acid has not been previously detected or described in these organisms. However, a recent description of a phylogenetically related species of Thermogemmatispora (Yabe et al., Int J Syst Evol Microbiol 61:903–910, 2010), noted an unidentified 20:0 fatty acid with matching GC behavior and GCMS data to that of strain T81. These data suggest that Thermogemmatispora share an ability to synthesize the same fatty acid. A number of other dimethyl‐branched fatty acids, namely 8,14‐diMe 15:0; 12,15‐diMe 16:0; 10,15‐diMe 16:0; 12,16‐diMe 17:0; 10,16‐diMe 17:0; 12,17‐diMe 18:0; 12,18‐diMe 19:0; 14,19‐diMe 20:0, were also identified in strain T81.