Macromerine and normacromerine biosynthesis in Coryphantha macromeris var. runyonii.

The biosynthetic conversion of epinephrine to normacromerine in Coryphantha macromeris (Engelm.) Br. and R. var. runyonii (Br. and R.) L. Benson (Cactacae) has been studied. Metanephrine, which has been isolated from this cactus and is a normal metabolite of epinephrine in mammalian systems, appeared to be the likely intermediate between epinephrine and normacromerine. Normacromerine turnover studies suggested a 16-day interval between metanephrine administration and harvest of the cacti. During this incubation period, the cacti specifically converted 4.77% of the administered DL-7-3H-metanephrine to normacromerine. Based on biochemical precedents, the postulated metabolic fate of normacromerine in the cactus was an enzymatic N-methylation to give macromerine. However, radiolabeled normacromerine was a very ineffecient precursor to macromerine.