Abstract
The title compound (systematic name: 9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4H,5H-naphtho[2,3-b]furan-2,8-dione), C15H20O4, is a sesquiterpene lactone showing the typical eremophilanolide skeleton, which has been isolated from the plant Senecio candidans collected in the Chilean Magallanes region. The present study confirms the atomic connectivity assigned on the basis of 1H and 13C NMR spectroscopy, as well as the relative stereochemistry of the 4α-methyl,5α-methyl,8β-hydroxy,10β-H unit. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds involving the hydroxy group as donor and the oxo group as acceptor, giving chains along the a axis. The absolute structure was not determined because of the lack of suitable anomalous scatters.
Highlights
The title compound, C15H20O4, is a sesquiterpene lactone showing the typical eremophilanolide skeleton, which has been isolated from the plant Senecio candidans collected in the Chilean Magallanes region
For the biological activity of metabolites isolated from plants of the Senecio species, see: Ulubelen et al (1971); BurgueñoTapia et al (2007); Domınguez et al (2008); Reina,GonzálezColoma, Domınguez-Dıaz et al (2006); Reina, GonzálezColoma, Gutiérrez et al (2006)
As part of our ongoing study of Senecio genus from the chilean shouthern and Magallanes Region, in this work we report the isolation and the molecular and crystal structure determination of the title compound, which it is described for the first time as a metabolite for the Senecio genus
Summary
Naturales y Agrobiologıa (IPNA-CSIC), Astrofısico Francisco Sánchez, 3, 38206 La. Laguna, Tenerife, Spain, cFacultad de Ciencias, Universidad de Magallanes (UMAG), Punta Arenas, Chile, and dFacultad de Quımica y Biologıa, Universidad de Santiago de Chile, Chile.
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