title: Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity.
abstract: A new tetrasubstituted pyran-2-one and a new dihydrobenzofuran, named colletochlorins E and F (1 and 2, respectively), were isolated from the culture filtrates of the fungus Colletotrichum higginsianum together with the already known colletochlorin A, 4-chloroorcinol, and colletopyrone. Colletochlorin E, the main metabolite, and colletochlorin F were characterized by spectroscopic (NMR, HRESIMS) and chemical methods as 3-[7-chloro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-5-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 7-chloro-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-4-ol, respectively. The absolute configuration 2'S of 1 was deduced by X-ray diffractometric analysis, whereas 2S of 2 was deduced by comparison of its NMR and CD data with those of 1. When assayed by leaf puncture on Sonchus arvensis and tomato leaves, 2 caused quite large necrosis (>1 cm), whereas 4-chloroorcinol proved to be the most active compound. These results were confirmed by those obtained in assays on Lemna minor and Phelipanche ramosa seed germination. Furthermore 1, colletochlorin A and colletopyrone were less or modestly active in the latter assay, respectively. Interestingly, the phytotoxicity was not associated with an antibiotic activity, whereas only 4-chloroorcinol and colletochlorin F exhibited zootoxic activity.
authors.affiliation: Department of Chimical Sciences, University of Naples Federico II, Complesso Universitario Monte San'Angelo , Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Masi
authors.affiliation: Department of Chimical Sciences, University of Naples Federico II, Complesso Universitario Monte San'Angelo , Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.affiliation: Institute of Food Production Sciences, National Research Council , Via Amendola 122/O, 70125 Bari, Italy.
authors.forename: Angela
authors.initials: A
authors.lastname: Boari
authors.affiliation: Department of Chimical Sciences, University of Naples Federico II, Complesso Universitario Monte San'Angelo , Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Angela
authors.initials: A
authors.lastname: Tuzi
authors.affiliation: Institute of Food Production Sciences, National Research Council , Via Amendola 122/O, 70125 Bari, Italy.
authors.forename: Maria Chiara
authors.initials: MC
authors.lastname: Zonno
authors.affiliation: Laboratoire Universitaire de Biodiversité et Ecologie Microbienne, Université de Brest , EA 3882, IBSAM, ESIAB, Technopôle Brest-Iroise, 29280 Plouzané, France.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Baroncelli
authors.affiliation: Institute of Food Production Sciences, National Research Council , Via Amendola 122/O, 70125 Bari, Italy.
authors.forename: Maurizio
authors.initials: M
authors.lastname: Vurro
authors.affiliation: Department of Chimical Sciences, University of Naples Federico II, Complesso Universitario Monte San'Angelo , Via Cintia 4, 80126 Napoli, Italy.
authors.forename: Antonio
authors.identifier: http://orcid.org/0000-0001-9110-1656
authors.initials: A
authors.lastname: Evidente
mesh_terms: D000818:Animals; D001156:Artemia / Q000187:drug effects; D001572:Benzofurans / Q000737:chemistry; D020231:Colletotrichum / Q000737:chemistry* / Q000378:metabolism; D006540:Herbicides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018551:Solanum lycopersicum / Q000187:drug effects; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry; D064210:Secondary Metabolism; D031184:Sonchus / Q000187:drug effects
chemical_list: D001572:Benzofurans; D006540:Herbicides; D006576:Heterocyclic Compounds, 4 or More Rings; D011753:Pyrones; C000619713:colletochlorin E; C000619714:colletochlorin F; C105430:benzofuran
keywords: Colletotrichum higginsianum; biocontrol; colletochlorins E and F; phytotoxins; pyran-2-ones and dihydrobenzofurans