title: Pinolide, a new nonenolide produced by Didymella pinodes , the causal agent of ascochyta blight on Pisum sativum.
abstract: An aggressive isolate of  Didymella pinodes  isolated from pea ( Pisum sativum ) produced four different metabolites in vitro. The metabolites isolated from the culture filtrates were characterized by spectroscopic and optical methods. A new nonenolide, named pinolide, was isolated and characterized as (2S*,7R*,8S*,5E,9R*)-2,7,8-trihydroxy-9-propyl-5-nonen-9-olide. Pinolidoxin, the main toxin produced by D. pinodes, was also isolated together with two other closely related nonenolides, identified as herbarumin II and 2-epi-herbarumin II. Herbarumin II and 2-epi-herbarumin II have been previously isolated from the fungi  Phoma herbarum  and  Paraphaeosphaeria recurvifoliae , respectively, but described here to be isolated for the first time from D. pinodes. When tested on leaves of the host plant and other legumes and weeds, pinolidoxin was phytotoxic in all of the plant species, whereas the other three nonenolides did not produce any symptoms. The importance of the stereochemistry of the hydroxy group at C-7 on phytotoxicity also is discussed.
authors.affiliation: Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali, Università di Napoli Federico II, Via Università 100, 80055 Portici, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Sara
authors.initials: S
authors.lastname: Fondevilla
authors.forename: Mohamed A
authors.initials: MA
authors.lastname: Abouzeid
authors.forename: Diego
authors.initials: D
authors.lastname: Rubiales
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D001203:Ascomycota / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry / Q000378:metabolism*; D018532:Pisum sativum / Q000382:microbiology*; D010935:Plant Diseases / Q000382:microbiology*
chemical_list: D009183:Mycotoxins