A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae)
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 alkaloid...
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/9/14637 |
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| author | Michelle Rodrigues e Rocha Jucimar Jorgeane de Souza Lucas Tricarico Barcellos Carlos Mauricio R. Sant'Anna Raimundo Braz-Filho Ivo José Curcino Vieira |
| author_facet | Michelle Rodrigues e Rocha Jucimar Jorgeane de Souza Lucas Tricarico Barcellos Carlos Mauricio R. Sant'Anna Raimundo Braz-Filho Ivo José Curcino Vieira |
| author_sort | Michelle Rodrigues e Rocha |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T14:40:44Z |
| format | Article |
| id | doaj.art-89c550f7d2d14a8c9f65cbf749eab9b9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T14:40:44Z |
| publishDate | 2014-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-89c550f7d2d14a8c9f65cbf749eab9b92022-12-21T18:22:32ZengMDPI AGMolecules1420-30492014-09-01199146371464810.3390/molecules190914637molecules190914637A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae)Michelle Rodrigues e Rocha0Jucimar Jorgeane de Souza1Lucas Tricarico Barcellos2Carlos Mauricio R. Sant'Anna3Raimundo Braz-Filho4Ivo José Curcino Vieira5Laboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes 28013-602, BrazilLaboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes 28013-602, BrazilDepartamento de Química, Instituto de Ciência Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, BrazilDepartamento de Química, Instituto de Ciência Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, BrazilLaboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes 28013-602, BrazilLaboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes 28013-602, BrazilA 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.http://www.mdpi.com/1420-3049/19/9/14637RutaceaeRauia nodosasteroidsalkaloidscoumarins |
| spellingShingle | Michelle Rodrigues e Rocha Jucimar Jorgeane de Souza Lucas Tricarico Barcellos Carlos Mauricio R. Sant'Anna Raimundo Braz-Filho Ivo José Curcino Vieira A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) Molecules Rutaceae Rauia nodosa steroids alkaloids coumarins |
| title | A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) |
| title_full | A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) |
| title_fullStr | A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) |
| title_full_unstemmed | A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) |
| title_short | A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae) |
| title_sort | novel 3 9 1 2 3 trioxocine type steroid of rauia nodosa rutaceae |
| topic | Rutaceae Rauia nodosa steroids alkaloids coumarins |
| url | http://www.mdpi.com/1420-3049/19/9/14637 |
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