title: Chenopodolin: a phytotoxic unrearranged ent-pimaradiene diterpene produced by Phoma chenopodicola, a fungal pathogen for Chenopodium album biocontrol.
abstract: A new phytotoxic unrearranged ent-pimaradiene diterpene, named chenopodolin, was isolated from the liquid culture of Phoma chenopodicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops such as sugar beet and maize. The structure of chenopodolin was established by spectroscopic, X-ray, and chemical methods as (1S,2S,3S,4S,5S,9R,10S,12S,13S)-1,12-acetoxy-2,3-hydroxy-6-oxopimara-7(8),15-dien-18-oic acid 2,18-lactone. At a concentration of 2 mg/mL, the toxin caused necrotic lesions on Mercurialis annua, Cirsium arvense, and Setaria viride. Five derivatives were prepared by chemical modification of chenopodolin functionalities, and some structure-activity relationships are discussed.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte. S. Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Maria C
authors.initials: MC
authors.lastname: Zonno
authors.forename: Fabiana
authors.initials: F
authors.lastname: Avolio
authors.forename: Antonello
authors.initials: A
authors.lastname: Santini
authors.forename: Angela
authors.initials: A
authors.lastname: Tuzi
authors.forename: Alexander
authors.initials: A
authors.lastname: Berestetskyi
authors.forename: Maurizio
authors.initials: M
authors.lastname: Vurro
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D001412:Bacillus subtilis / Q000187:drug effects; D027461:Beta vulgaris / Q000187:drug effects; D027463:Chenopodium album / Q000187:drug effects / Q000382:microbiology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000737:chemistry*; D005848:Geotrichum / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000382:microbiology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D003313:Zea mays / Q000187:drug effects
chemical_list: D004224:Diterpenes; C584068:chenopodolin