title: Diplopimarane, a 20-nor-ent-pimarane produced by the oak pathogen Diplodia quercivora.
abstract: In this study a new 20-nor-ent-pimarane, named diplopimarane, was isolated together with sphaeropsidins A (9) and C (10), and (+)-epiepoformin (11) from organic crude extracts of Diplodia quercivora, a recently described oak pathogen originally found on declining Quercus canariensis trees in Tunisia. Diplopimarane was characterized as (1S,2R)-2,8,8-trimethyl-2-vinyl-1,2,3,4,5,6,7,8-octahydrophenanthrene-1,9,10-triol by spectroscopic, X-ray, optical, and chemical methods. It exhibited a wide range of activities including remarkable phytotoxicity on nonhost plants such as tomato cuttings, moderate antifungal activity against important plant pathogens, and moderate zootoxicity against Artemia salina. Its derivatives (2-4 and 6) were also tested for their phytotoxic and zootoxic activities. All these derivatives proved to be active against A. salina at 200 μg/mL, while 2 and 6 were also active on tomato cuttings. The other secondary metabolites (9, 10, and 11) herein reported for D. quercivora exhibited phytotoxic, antifungal, and zootoxic activity. This is the first report on the secondary metabolites secreted in vitro by this oak pathogen that could be key components of its adaptative strategies.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant'Angelo , Via Cintia 4, 80126, Napoli, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Lucia
authors.initials: L
authors.lastname: Maddau
authors.forename: Sara
authors.initials: S
authors.lastname: Basso
authors.forename: Benedetto T
authors.initials: BT
authors.lastname: Linaldeddu
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Bruno
authors.initials: B
authors.lastname: Scanu
authors.forename: Antonio
authors.initials: A
authors.lastname: Deidda
authors.forename: Angela
authors.initials: A
authors.lastname: Tuzi
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001156:Artemia / Q000187:drug effects; D001203:Ascomycota / Q000737:chemistry*; D018551:Solanum lycopersicum / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010935:Plant Diseases / Q000382:microbiology; D029963:Quercus / Q000382:microbiology; D014416:Tunisia
chemical_list: D045784:Abietanes; D000935:Antifungal Agents; C000599084:diplopimarane; C433018:pimarane