A novel 3,9-(1,2,3-trioxocine)-type steroid of Rauia nodosa (Rutaceae)

Molecules. 2014 Sep 16;19(9):14637-48. doi: 10.3390/molecules190914637.

Abstract

A new natural product, a 3,9-(1,2,3-trioxocine)-type steroid, named rauianodoxy (6), was isolated from Rauia nodosa, together with five steroids: sistostenone (1), stigmastenone (2), sitosterol (3), stigmasterol (4) and ergosterol peroxide (5), one coumarin, O-geranylosthenol (7), and three alkaloids, N-methylflindersine (8), zantobungeanine (9) and veprissine (10). Compounds 5-8 were isolated for the first time in the genus Rauia. These compounds were characterized on the basis of their spectral data, mainly one and two-dimensional NMR, and mass spectra, also involving comparison with the literature data. Theoretical studies at the DFT level reveal structural parameters for the 1,2,3-trioxole bridge compatible with known structures containing a similar group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Coumarins / chemistry*
  • Coumarins / classification
  • Coumarins / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Leaves / chemistry*
  • Rutaceae / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Steroids / chemistry*
  • Steroids / classification
  • Steroids / isolation & purification
  • Stigmasterol / chemistry
  • Triterpenes / chemistry*

Substances

  • Alkaloids
  • Coumarins
  • Steroids
  • Triterpenes
  • Stigmasterol