Phloroglucinol derivatives from leaves of Bosistoa pentacocca

Leaves from four collections of Bosistoa pentacocca, two of the variety connaricarpa and one each of the type variety and var. dryanderensis, have been examined. In each, the major metabolite isolated was characterized as 2-(3,7-dimethyloct-2,5-dienyl)-6-(3-methylbut-2-enyl)phloroglucinol-1-acetate (trivial name pentacoccol). Four other pentacoccol derivatives were obtained as minor components, pentacoccol-5-methyl ether (from var. pentacocca and var. dryanderensis), 2,2-dimethyl-3 xi,7-dihydroxy-5-acetoxy-6-(3,7-dimethyloct-2,5-dienyl)-3,4-dihydrobenzo-[2H]-pyran (3'-hydroxydihydropyranopentacoccol from var. connaricarpa), 2-(1-hydroxy-1-methylethyl)-4-acetoxy-5-(3,7-dimethyloct-2,5-dienyl)-6-hydroxybenzo-[2H]-furan (2'-(1-hydroxyosopropyl)furanopentacoccol from var. pentacocca) and 4-acetoxy-5-(3,7-dimethyloct-2,5-dienyl)-6-hydroxybenzo-[2H]-furan (furanopentacoccol from var. dryanderensis). All compounds were identified on the basis of their spectroscopic data. (C) 1997 Elsevier Science Ltd. All rights reserved.