Biotransformation of the Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one by cell suspension cultures of Pinus radiata

• Published in: Phytochemistry (Oxford) Vol. 53; no. 4; pp. 447 - 450
• Main Authors: COONEY, J. M, HOTTER, G. S, LAUREN, D. R
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier 01.02.2000
• Subjects: 6-Pentyl-2H-pyran-2-one; Antifungal Agents - metabolism; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Biotransformation; Cell Culture Techniques; Chromatography, High Pressure Liquid; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; Pinus radiata; Pyrones - metabolism; Trees - metabolism; Trichoderma; Trichoderma - metabolism; Cell culture; Trichoderma; Hydroxylation; Molecular structure; Metabolite; Pinus radiata; Pyranone derivatives; Fungi; Antifungal agent; Microbial origin; Biotransformation; Softwood forest tree; Gymnospermae; Coniferales; Spermatophyta; Fungi Imperfecti; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(99)00590-7

Cell suspension cultures of Pinus radiata metabolize the antifungal Trichoderma secondary metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) (1) via hydroxylation of the pentyl side chain. Examination of the culture medium following dosing studies with 1 revealed that 79-85% of this bioactive compound had been metabolised after 144 h. At that time, 34-40% of the metabolized dose was recovered as a series of monohydroxylated isomers of 1, the principal metabolite being 5-(2-pyron-6-yl)pentan-5-ol (7).