title: Pogostol biosynthesis by the endophytic fungus Geniculosporium.
abstract: Six (13)C-labelled isotopomers of mevalonolactone were synthesised and used in feeding experiments with the endophytic fungus Geniculosporium. The high incorporation rates of (13)C-label into a sesquiterpene that was found in headspace extracts of the fungus enabled unambiguous identification of this volatile as pogostol without the need for compound purification, simply by collecting the volatile fraction with a closed-loop stripping apparatus followed by direct (13)C NMR analysis (CLSA-NMR). The feeding experiments also gave insights into the biosynthesis of pogostol, including stereochemical aspects of the terpene cyclisation reaction. The possible biological function of pogostol is discussed.
authors.affiliation: Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany).
authors.forename: Lena
authors.initials: L
authors.lastname: Barra
authors.forename: Barbara
authors.initials: B
authors.lastname: Schulz
authors.forename: Jeroen S
authors.initials: JS
authors.lastname: Dickschat
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry; D003500:Cyclization; D005658:Fungi / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D007553:Isotope Labeling; D008798:Mevalonic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D045789:Sesquiterpenes, Guaiane / Q000096:biosynthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002247:Carbon Isotopes; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C015367:mevalonolactone; D008798:Mevalonic Acid
keywords: NMR; isotopic labeling; terpenoids; trace analysis; volatiles