A new eremophilanolide from Senecio sinuatus Gilib.
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.
Burgueño-Tapia
Eleuterio
E
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
López-Escobedo
Susana
S
González-Ledesma
Manuel
M
Joseph-Nathan
Pedro
P
D002247:Carbon Isotopes; D003198:Computer Simulation; D006586:Hexanes / Q000737:chemistry; D006859:Hydrogen; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry*; D012674:Senecio / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification
C522113:3beta-angeloyloxy-6beta-hydroxyeremophil-1(10)-en-8beta,12-olide; D002247:Carbon Isotopes; D006586:Hexanes; D012717:Sesquiterpenes; D012997:Solvents; D014315:Triterpenes; C492472:eremophilenolide; D006859:Hydrogen