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

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-o ne and (3aR{*},6R{*},7aS)-6-methoxy-3a,7a-dihydro-3H,6H-furo\{[\}2,3-b]pyran-2-on e, 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. (C) 2012 Elsevier Ltd. All rights reserved.