title: Guaiane sesquiterpenes from Biscogniauxia nummularia featuring potent antigerminative activity.
abstract: Xylaranone, a previously unreported guaiane sesquiterpene along with the known terpenoid xylaranol B and the two mellein derivatives 3,5-dimethyl-8-methoxy-3,4-dihydroisocoumarin and 3,5-dimethyl-8-hydroxy-3,4-dihydroisocoumarin were isolated from Biscogniauxia nummularia. Pogostol was also isolated from this fungus, and in light of our spectroscopic data, its structure was revised and corrected. This fungus, which was isolated as an endophyte from the plum yew Cephalotaxus harringtonia, is also suspected of being a pathogen. Interestingly, we report here the potent antigerminative activity of xylaranone and xylaranol B against seeds of Raphanus sativus at concentrations comparable to glyphosate, a commonly used herbicide. This effect suggests a role for these metabolites in the latent fungal pathogenesis of B. nummularia.
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 Rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Séverine
authors.initials: S
authors.lastname: Amand
authors.forename: Aude
authors.initials: A
authors.lastname: Langenfeld
authors.forename: Alain
authors.initials: A
authors.lastname: Blond
authors.forename: Joëlle
authors.initials: J
authors.lastname: Dupont
authors.forename: Bastien
authors.initials: B
authors.lastname: Nay
authors.forename: Soizic
authors.initials: S
authors.lastname: Prado
mesh_terms: D032483:Cephalotaxus / Q000382:microbiology*; D018525:Germination / Q000187:drug effects*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013098:Xylariales / Q000737:chemistry*
chemical_list: D045789:Sesquiterpenes, Guaiane; C573614:xylaranone