Characterization of Novel Methyl-Branched Chain Fatty Acids from a Halophilic Bacillus Species

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2001-02, Vol.64 (2), p.256-259
• Main Authors: Carballeira, Néstor M, Miranda, Carlos, Lozano, César M, Nechev, Jordan T, Ivanova, Albena, Stefanov, Kamen, Ilieva, Mirolyuba, Tzvetkova, Iva
• Format: Article
• Language: English
• Subjects: Bacillus; Bacillus - chemistry; Bacteriology; Biological and medical sciences; Brackish; Bulgaria; dimethyltetradecanoic and; Fatty Acids - chemistry; Fatty Acids - isolation & purification; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Microbiology; Morphology, structure, chemical composition; natural products
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np000494d

The 4-methylated fatty acids 4,9-dimethyldecanoic, 4,11-dimethyldodecanoic, 4,10-dimethyldodecanoic, and 4,13-dimethyltetradecanoic acid as well as the 2-methylated fatty acids 2,13-dimethyltetradecanoic and 2,12-dimethyltetradecanoic acid were identified for the first time in nature in the halophilic bacterium Bacillus sp. isolated from the salt pans of Burgas in Bulgaria. The principal fatty acids in this bacterium were a series of iso-anteiso fatty acids with chain lengths between C11 and C19, but an interesting series of linear alkylbenzene fatty acids with chain lengths between C10 and C14, such as 12-phenyldodecanoic acid, were also identified. The novel 4-methylated fatty acids were characterized using a combination of GC−MS and chemical transformations such as N-acylpyrrolidide derivatization. The 2-methylated fatty acids were also identified by GC−MS and gas chromatographic coelution with synthetic samples. The novel methyl-branched fatty acids probably originated from the selective incorporation of methylmalonyl-CoA by one of the fatty acid-synthesizing enzymes of the bacterium.