A new eremophilanolide from Senecio sinuatus Gilib |
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Authors: | Burgueño-Tapia Eleuterio López-Escobedo Susana González-Ledesma Manuel Joseph-Nathan Pedro |
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Institution: | Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Tomás, México D. F., 11340 México. eleuterio@woodward.encb.ipn.mx |
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Abstract: | From the hexane extracts of Senecio sinuatus roots, the new 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-en-8beta,12-olide (3), along with the known compounds 3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-ene (1), 3beta-senecioyloxy-6beta-hydroxyeremophil-1(10)-ene (2), and 3beta-angeloyloxy-6beta,8alpha-dihydroxyeremophil-1(10)-en-8beta,12-olide (4), were isolated. Complete 1H and 13C NMR chemical shift assignments of 1-4 were achieved using one- and two-dimensional NMR techniques, including gHMQC and gHMBC experiments. A Monte Carlo search, followed by B3LYP/6-31G*DFT calculation, provided the theoretical conformations of the eremophilane rings, which were in agreement with results derived from 1H-1H NMR coupling constant analysis, and confirmed by NOESY experiments. |
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Keywords: | 1H NMR 13C NMR 2D NMR Senecio sinuatus senecionae asteraceae sesquiterpene lactones eremophilanolides furanoeremophilanes |
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