title: Dhilirolides E-N, meroterpenoids produced in culture by the fungus Penicillium purpurogenum collected in Sri Lanka: structure elucidation, stable isotope feeding studies, and insecticidal activity.
abstract: Extracts of laboratory cultures of the fungus Penicilium purpurogenum obtained from rotting fruit of the tree Averrhoa bilimbi growing in Sri Lanka have yielded 10 new meroterpenoids, dhilirolides E-N (5-14). The structures of the new dhilirolides have been elucidated by analysis of spectroscopic data and a single-crystal X-ray diffraction analysis of dhilirolide L (12). Dhilirolides A-N (1-14) represent the four unprecedented and rearranged dhilirane, isodhilirane, 14,15-dinordhilirane, and 23,24-dinorisodhilirane meroterpenoid carbon skeletons. Stable isotope feeding studies have confirmed the meroterpenoid biogenetic origin of the dhilirolides and provided support for a proposed genesis of the new carbon skeletons. Dhilirolide L (12) showed significant feeding inhibition and sublethal developmental disruption in the cabbage looper Trichoplusia ni, an important agricultural pest, at low concentrations.
authors.affiliation: Departments of Chemistry and ‡Earth & Ocean Sciences, University of British Columbia , Vancouver, BC, Canada V6T 1Z1;
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Centko
authors.forename: David E
authors.initials: DE
authors.lastname: Williams
authors.forename: Brian O
authors.initials: BO
authors.lastname: Patrick
authors.forename: Yasmin
authors.initials: Y
authors.lastname: Akhtar
authors.forename: Miguel Angel
authors.initials: MA
authors.lastname: Garcia Chavez
authors.forename: Yan Alexander
authors.initials: YA
authors.lastname: Wang
authors.forename: Murray B
authors.initials: MB
authors.lastname: Isman
authors.forename: E Dilip
authors.initials: ED
authors.lastname: de Silva
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
mesh_terms: D000818:Animals; D007306:Insecticides / Q000737:chemistry*; D007554:Isotopes / Q000737:chemistry*; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013188:Sri Lanka; D013729:Terpenes / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D007306:Insecticides; D007554:Isotopes; D013729:Terpenes; C557929:dhilirolide A