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

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

Michelle Rodrigues e Rocha  1 , Jucimar Jorgeane de Souza  1 , Lucas Tricarico Barcellos  2 , Carlos Mauricio R Sant'Anna  2 , Raimundo Braz-Filho  1 , Ivo José Curcino Vieira  3
Affiliations

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

Michelle Rodrigues e Rocha et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Compounds isolated from the stems of Rauia nodosa (1–10) and compounds 11–13.
Scheme 1
Scheme 1
Proposed fragmentation mechanisms to justify peaks (positive modes, only peaks classified as principal) obtained in a methanol/water solution of compound 6.
Figure 2
Figure 2
Select (NOE) spatial correlations and relative stereochemistry for 3,9-(1,2,3-trioxocine)-type steroid rauianodoxy (6). Arrows denote NOE spatial correlations principals.
Figure 3
Figure 3
Perpendicular views of the 3D representation of LSDA/pBP86/DN* optimized structure of the 3,9-(1,2,3-trioxocine)-type steroid, compound 6.
See this image and copyright information in PMC

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