title: Biological evaluation and determination of the absolute configuration of chloromonilicin, a strong antimicrobial metabolite isolated from Alternaria sonchi.
abstract: Chloromonilicin was isolated for the first time from Alternaria sonchi, a mycoherbicide proposed for the control of the noxious weed Sonchus arvensis. The already known alternethanoxins A and B and the three recently isolated phytotoxic polycyclic ethanones named alternethanoxins C-E were also isolated from the same source. Chloromonilicin was identified by spectroscopic data (essentially one-dimensional NMR, 2-dimensional NMR and high-resolution ESI-MS) and its structure was confirmed by single X-ray analysis, which also allowed the assignment of the absolute configuration. This latter was independently confirmed by electronic CD calculations. When chloromonilicin was tested for its antimicrobial activity, it was active at concentrations 0.5-1 μg per disc against four bacterial species and a yeast fungus. The compound inhibited conidial germination of four plant pathogens at concentration of 1-10 μg ml(-1). No phytotoxic activity of this antibiotic by leaf-disc puncture bioassay was detected.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
authors.affiliation: Department of Phytotoxicology and Biotechnology, All-Russian Institute of Plant Protection, Federal Agency of Scientific Organizations, Pushkin, Saint Petersburg, Russian Federation.
authors.forename: Alexander
authors.initials: A
authors.lastname: Berestetskiy
authors.affiliation: Department of Phytotoxicology and Biotechnology, All-Russian Institute of Plant Protection, Federal Agency of Scientific Organizations, Pushkin, Saint Petersburg, Russian Federation.
authors.forename: Anna
authors.initials: A
authors.lastname: Dalinova
authors.affiliation: Department of Chemical Modelling, Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, Saint-Petersburg, Russian Federation.
authors.forename: Denis
authors.initials: D
authors.lastname: Krivorotov
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
authors.forename: Angela
authors.initials: A
authors.lastname: Tuzi
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D000528:Alternaria / Q000737:chemistry / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000900:Anti-Bacterial Agents; D001578:Benzopyrans; C045382:chloromonilicin