Sphaeropsidins D and E, two other pimarane diterpenes, produced in vitro by the plant pathogenic fungus Sphaeropsis sapinea f. sp. cupressi

Two pimarane diterpenes structurally related to sphaeropsidins were isolated from the liquid culture of Sphaeropsis sapinea f. sp. cupressi, a plant pathogenic fungus causing a form of canker disease of Italian cypress ( Cupressus sempervirens L.). The two metabolites, characterised by spectroscopic methods, were named sphaeropsidins D (0.40 mg l −1) and E (0.16 mg l −1). The same fungus produced sphaeropsidins A, B and C, sphaeropsidone and episphaeropsidone, which proved to be phytotoxic to cypress, and chlorosphaeropsidone and epichlorosphaeropsidone showing no phytotoxicity. Sphaeropsidin D assayed at 0.1 mg ml −1 on severed cypress twigs caused leaf browning and necrosis on Cupressus macrocarpa, but no symptoms were observed on C. sempervirens and C. arizonica. Symptoms appeared in a period of time (6 days after toxin-treatment) shorter than that for sphaeropsidin A. Sphaeropsidin E assayed at 0.2 mg ml −1 did not produce any symptom on the same cypress species tested with sphaeropsidin D. We report the isolation and the chemical and biological characterization of sphaeropsidins D and E ( 5), two pimarane diterpenes, produced by Spharopsis sapinea f. sp . cupressi causing a canker form on cypress. Sphaeropsidin D appeared to be a 11-α-hydroxysphaeropsidin A.