Production of Tricarboxylic Acid Anhydrides from Fatty Acids by a Lipase-producing Strain of Pseudomonas cepacia

• Published in: Biocatalysis and biotransformation Vol. 20; no. 2; pp. 117 - 128
• Main Authors: Cardenas, Fernando, Vazquez, Maria J., Rivera-Sagredo, Alfonso, Sanchez-Montero, Jose M., Sinisterra, Jose V., Elson, Steve W., Alvarez, Emilio
• Format: Journal Article
• Language: English
• Published: Abingdon Informa UK Ltd 2002; Taylor & Francis; Taylor and Francis
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biosynthesis; Biotechnology; Fatty Acids; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; Microbial Lipases; Pseudomonas Cepacia; Tricarboxylic Acid Anhydrides; Enzyme; Triacylglycerol lipase; Esterases; Organic anhydride; Fatty acids; Antimicrobial agent; Carboxylic ester hydrolases; Oleic acid; Biotransformation; Burkholderia cepacia; Production; Microorganism culture; Bacteria; Hydrolases; Tricarboxylic acid
• ISSN: 1024-2422; 1029-2446
• DOI: 10.1080/10242420290018104

A lipase-producing strain of Pseudomonas cepacia isolated from a soil sample was found to produce five compounds when oleic acid was added to the culture medium as lipase inducer. The five compounds were isolated by solvent extraction, silicagel column chromatography and preparative HPLC, and their structural elucidation was performed by mass spectrometry, and infrared and nuclear magnetic resonance spectroscopies. The products were identified as dec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 1 ), undec-3-ene-1,3,4-tricarboxylic acid 3,4-anhydride (product 2 ), dodec-3-ene-I,3,4-tricarboxylic acid 3,4-anhydride (product 3 ), dodec-3,8-diene-1,3,4-tricarboxylic acid 3,4-anhydride (product 4 ) and dodec-3,6-diene-I,3,4-tricarboxylic acid 3,4-anhydride (product 5 ). Accumulation of these compounds in the culture medium started after oleic acid consumption and followed a pattern similar to that found for cell growth and for lipase production. The five compounds were radioactively labeled when [U- 14 C]oleic acid was supplied to the culture medium, thus showing that they were produced by transformation of the acid. When isolated from cultures containing [1,2- 13 C]acetic acid and oleic acid as the sole sources of carbon, the compounds showed to contain the 13 C isotope only in the first five atoms of carbon of the molecule. Several long chain fatty acids also acted as precursors of these compounds, with maximal yields for chain lengths between 11 and 18 atoms of carbon. None of the five compounds acted as lipase inducer when added to the culture medium instead of oleic acid. The compounds showed moderate antibacterial and antifungal activities when tested in solid media bioassays.