Sucupiranins A-L, Furanocassane Diterpenoids from the Seeds of Bowdichia virgilioides

J Nat Prod. 2017 Dec 22;80(12):3120-3127. doi: 10.1021/acs.jnatprod.7b00249. Epub 2017 Nov 28.

Abstract

Twelve new furanocassane diterpenoids, sucupiranins A-L (1-12), and three known compounds (13-15) were isolated from the seeds of Bowdichia virgilioides. The structures of the compounds were elucidated via 1H and 13C NMR analysis, including 2D NMR (1H-1H COSY, HSQC, HMBC, and NOESY); HRMS data; and X-ray crystallographic analysis. The absolute configurations were defined using their electronic circular dichroism (ECD) spectra by applying the exciton chirality method to the bis-p-bromobenzoate of compound 13. Sucupiranin J (10) inhibited lipopolysaccharide-induced nitric oxide production (IC50 30.6 μM), whereas sucupiranins J (10), K (11), and 13 exhibited weak antimalarial activity against Plasmodium falciparum K1 with IC50 values of 32.2, 23.5, and 22.9 μM and selectivity indices of 4.3, 1.9, and >12.0 (MRC-5/K1), respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Crystallography, X-Ray / methods
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology
  • Fabaceae / chemistry*
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy / methods
  • Nitric Oxide / metabolism
  • Plasmodium falciparum / drug effects
  • Seeds / chemistry*

Substances

  • Antimalarials
  • Diterpenes
  • Lipopolysaccharides
  • Nitric Oxide