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Cyclobotryoxide, a phytotoxic metabolite produced by the Plurivorous pathogen Neofusicoccum australe

Andolfi, Anna and Maddau, Lucia and Cimmino, Alessio and Linaldeddu, Benedetto Teodoro and Franceschini, Antonio and Serra, Salvatorica and Basso, Sara and Melck, Dominique and Evidente, Antonio (2012) Cyclobotryoxide, a phytotoxic metabolite produced by the Plurivorous pathogen Neofusicoccum australe. Journal of Natural Products, Vol. 75 (10), p. 1785-1791. eISSN 1520-6025. Article.

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DOI: 10.1021/np300512m

Abstract

Two isolates of Neofusicoccum australe belonging to ITS haplotypes H4 and H1 and associated with grapevine cordon dieback and branch dieback of Phoenicean juniper, respectively, have been shown to produce in vitro structurally different secondary metabolites. From the strain BOT48 of N. australe (haplotype H4) a new cyclohexenone oxide, namely, cyclobotryoxide, was isolated together with 3-methylcatechol and tyrosol. Cyclobotryoxide was characterized as (1S,5R,6S)-5-hydroxy-3-methoxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one by spectroscopic, optical, and chemical methods. The strain BL24 (haplotype H1) produced tyrosol along with botryosphaerone D and (3S,4S)-3,4,8-trihydroxy-6-methoxy-3,4- dihydro-1(2H)-naphthalenone. The metabolites obtained from both strains were tested at four concentrations on leaves of grapevine cv. Cannonau, holm oak, and cork oak by the leaf puncture assay. Cyclobotryoxide proved to be the most phytotoxic compound. Tyrosol and cyclobotryoxide were also tested on detached grapevine leaves at concentrations of 0.25 and 0.5 mg/mL. Only cyclobotryoxide was found to be active in this bioassay.

Item Type:Article
ID Code:8108
Status:Published
Refereed:Yes
Uncontrolled Keywords:Cyclobotryoxide, Neofusicoccum australe, Cannonau
Subjects:Area 07 - Scienze agrarie e veterinarie > AGR/12 Patologia vegetale
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Agraria
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:American Chemical Society
eISSN:1520-6025
Copyright Holders:© 2012 American Chemical Society and American Society of Pharmacognosy
Deposited On:07 Nov 2012 09:06

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