Several oxidation products of metabolites produced by avimlent isolates of Phoma lingam, the blackleg fungus, are reported; in addition, the profile of metabolites common to P. lingam and P. wasabiae is clarified.Key words: cyclohexenedione, Phoma lingam, P. wasabiae.Resume : On a LtudiC plusieurs produits d'oxydation tires des metabolites produits par des isolats avimlents du Phoman lingam, un champignon; de plus, on a clarifiC le profil des metabolites communs au P. lingam et au P. wasabiae.Mots clis : cyclohex~nedione, Phoma lingam, P. wasabiae.
[Traduit par la redaction]Recent work on the so-called weakly virulent, avirulent, or nonaggressive isolates of the blackleg fungus (Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingum (Tode ex Fr.) Desm.) led to the isolation of several metabolites having a cyclohexenone ring as a common structural feature (1-3). Most importantly, this work revealed an unknown relationship between P. lingam and P. wasabiae. This unforeseen relationship2 was also supported by analysis of particular DNA sequences of isolates of both species (3). As a consequence of that work, it was proposed that the avirulent isolates of P. lingam be formally reclassified (4).As part of our continuing studies of the chemistry of the blackleg fungus,3 it was important to determine the phytotoxicity of the cyclohexenones 1, 2, 5-8 produced by avirulent isolates. During the purification of these metabolites, unexpected products resulting from the slow oxidation of 5 d 5 b and 6 were identified. Here is reported the transformation of phomaligadiones 5 and 6 and phomaligin A (7) to phomaligols 1 and 2, and the intermediates of these oxidative transformations, as well as the products of reaction of phomaligadiones 5 and 6 with diazomethane. These results allow an important clarification regarding the structures of metabolites common to P. wasabiae and P. lingam. In addition, the implications of these findings on the biogenesis of the cyclohexenone-containing metabolites is discussed and the structures of metabolites common to P. wasabiae and P. lingam are noted.