METABOLITES WITH NEMATOCIDAL AND ANTIMICROBIAL ACTIVITIES FROM THE ASCOMYCETE LACHNUM-PAPYRACEUM (KARST) KARST .5. PRODUCTION, ISOLATION AND BIOLOGICAL-ACTIVITIES OF BROMINE-CONTAINING MYCORRHIZIN AND LACHNUMON DERIVATIVES AND 4 ADDITIONAL NEW BIOACTIVE METABOLITES

Eight novel bioactive metabolites were isolated from submerged cultures of the ascomycete Lachnum papyraceum (Karst.) Karst, when CaBr2 was added to the cultures after the onset of secondary metabolism. Four of these metabolites (16 similar to 19) are bromo analogues of mycorrhizin A and lachnumon, while (1'Z)-dechloromycorrhizin A (12) and the papyracons A (13), B (14), and C (15) are non-halogenated compounds structurally related to the mycorrhizins. All compounds exhibited antimicrobial, cytotoxic, nematicidal and phytotoxic activities. The brominated mycorrhizins and lachnumons were found to be slightly less active than the chlorine-containing compounds. All mycorrhizin derivatives were mutagenic in the Ames test, suggesting DNA-alkylating properties.