X-Ray Crystal Structure of a Naturally Occurring trans-2-cis-4-Isomer of Wisanine, a Piperine-Type Alkaloid From Piper guineense

Journal of Natural Products
1984.0

Abstract

As part of our studies on the constituents of the medicinal plant, Piper guineense (West African Black or Ashanti pepper), a novel amide alkaloid (piperx) (1) was isolated from the root bark of the plant by Addae-Mensah et al. (1). The ir and 'H-nmr spectra of piperx indicated that it was identical with synthetic N-piperidyl-5-(2-methoxy-4,5-methylenedioxyphenyl)-trans-2-cis-4-pentadienamide (2) and hence a trans-cis isomer of the pharmacologically active amide alkaloid, wisanine (2) (3). The present X-ray analysis of piperx, the first naturally occurring mixed-isomer piperine-type alkaloid to be reported (1), was undertaken to confirm the structure. The results of the X-ray analysis confirm that piperx is a trans-2-cis-4 isomer of wisanine.

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