ANCISTROHEYNINE-A, THE FIRST 7,8'-COUPLED NAPHTHYLISOQUINOLINE ALKALOID FROM ANCISTROCLADUS-HEYNEANUS

The isolation and structural elucidation of a novel naphthylisoquinoli ne alkaloid, named ancistroheynine A, from the Indian liana Ancistracl adus heyneanus is described. The absolute configuration at the stereoc entre was established by oxidative degradation to give S-3-aminobutyri c acid. The axial configuration was unambiguously determined by long-r ange nuclear Overhauser enhancement (NOE) measurements, which covered the, as yet, longest distance within this class of compounds. Ancistro heynine A is the first 7,8'-coupled naphthylisoquinoline alkaloid foun d in A. heyneanus. Its accumulation in spherical inclusions is strongl y enhanced in aging parts of the plant. It displays pronounced in vitr o activity against Plasmodium falciparum, the most lethal human malari a parasite. Copyright (C) 1996 Elsevier Science Ltd