title: Strain of Fusarium oxysporum isolated from almond hulls produces styrene and 7-methyl-1,3,5-cyclooctatriene as the principal volatile components.
abstract: An isolated strain of Fusarium oxysporum from the hulls of Prunus dulcis (sweet almond) was found to produce relatively large quantities of the hydrocarbons styrene and two isomers of 7-methyl-1,3,5- cyclooctatriene (MCOT). Production of styrene and MCOT was reproduced on a small scale using potato dextrose agar as a growth medium and scaled up using 1 L of inoculated potato dextrose broth. The compounds were trapped as volatile organic compounds (VOCs) onto solid-phase microextraction (SPME) for small scale and Tenax for large scale and then isolated using standard high-performance liquid chromatography (HPLC) methods. Styrene was authenticated by a comparison to the retention times, fragmentation patterns, and calculated retention indices of a commercially available sample. The identity of MCOT was verified by a short chemical synthesis and a comparison of spectroscopic data to the isolated sample. A biosynthetic scheme of styrene is proposed on the basis of a (13)C-labeling study. This is the first report of MCOT isolated as a natural product.
authors.affiliation: Western Regional Research Center, U.S. Department of Agriculture, Albany, California 94710, USA. john.beck@ars.usda.gov
authors.forename: John J
authors.initials: JJ
authors.lastname: Beck
authors.forename: Glory B
authors.initials: GB
authors.lastname: Merrill
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Palumbo
authors.forename: Teresa L
authors.initials: TL
authors.lastname: O'Keeffe
mesh_terms: D034242:Cyclooctanes / Q000032:analysis / Q000378:metabolism*; D005670:Fusarium / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D027861:Prunus / Q000382:microbiology*; D020058:Styrene / Q000032:analysis / Q000378:metabolism*; D055549:Volatile Organic Compounds / Q000032:analysis / Q000378:metabolism*
chemical_list: C539737:7-methyl-1,3,5-cyclooctatriene; D034242:Cyclooctanes; D055549:Volatile Organic Compounds; D020058:Styrene