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Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea

Evidente, Antonio and Masi, Marco and Linaldeddu, Benedetto Teodoro and Franceschini, Antonio and Scanu, Bruno and Cimmino, Alessio and Andolfi, Anna and Motta, Andrea and Maddau, Lucia (2012) Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea. Phytochemistry, Vol. 77 , p. 245-250. ISSN 0031-9422. Article.

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DOI: 10.1016/j.phytochem.2012.01.011

Abstract

Two phytotoxic dihydrofuropyran-2-ones, named afritoxinones A and B, were isolated from liquid culture of Diplodia africana, a fungal pathogen responsible for branch dieback of Phoenicean juniper in Italy. Additionally, six others known metabolites were isolated and characterized: oxysporone, sphaeropsidin A, epi-sphaeropsidone, R-(−)-mellein, (3R,4R)-4-hydroxymellein and (3R,4S)-4-hydroxymellein. The structures of afritoxinones A and B were established by spectroscopic and optical methods and determined to be as (3aS∗,6R∗,7aS)-6-methoxy-3a,7a-dihydro-3H,6H-furo[2,3-b]pyran-2-one and (3aR∗,6R∗,7aS)-6-methoxy-3a,7a-dihydro-3H,6H-furo[2,3-b]pyran-2-one, respectively. The phytotoxic activity of afritoxinones A and B and oxysporone was evaluated on host (Phoenicean juniper) and non-host plant (holm oak, cork oak and tomato) by cutting and leaf puncture assay. Oxysporone proved to be the most phytotoxic compound. This study represents the first report of secondary metabolites produced by D. africana. In addition, the taxonomic implications of secondary metabolites in Botryosphaeriaceae family studies are discussed.

Item Type:Article
ID Code:8202
Status:Published
Refereed:Yes
Uncontrolled Keywords:Juniperus phoenicea, Botryosphaeriaceae, Diplodia africana, Phytotoxins, afritoxinones A and B
Subjects:Area 07 - Scienze agrarie e veterinarie > AGR/12 Patologia vegetale
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Agraria
Publisher:Elsevier
ISSN:0031-9422
Deposited On:20 Nov 2012 13:47

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