New Spiranoid Withanolides From Jaborosa Odonelliana

Abstract

first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessAbstract New Spiranoid Withanolides From Jaborosa Odonelliana by A. M. Cirigliano 1, A. S. Veleiro 1, J. C. Oberti 2 and G. Burton 1,* 1 Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, 1428 Buenos Aires, Argentina 2 Departamento de Química Orgánica and IMBIV, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 5016 Córdoba, Argentina * Author to whom correspondence should be addressed. Molecules 2000, 5(3), 441-442; https://doi.org/10.3390/50300441 Published: 22 March 2000 Download Download PDF Download PDF with Cover Download XML Download Epub Versions Notes Abstract: From whole Jaborosa odonelliana plants four new withanolides containing a spi-ranic lactone in the side chain, were isolated and their structures elucidated by spectroscopic methods. IntroductionAs part of our studies of the withanolides of argentine species of the genus Jaborosa we have rein-vestigated Jaborosa odonelliana from which we had isolated several years ago the unusual withanolide jaborosalactone P (1) [1]. J. odonelliana grows in the northwest of Argentina, mainly in arid and sandy soils. From plants collected in the province of Salta we have now isolated, besides jaborosalactone P, four new spiranoid withanolides (2-5), which differ from 1 in the substitution pattern of rings A and B. ExperimentalPlant material and isolation procedure: Whole plants of J. odonelliana A. T. Hunziker were col-lected in El Jardín, Depto la Candelaria, Salta. Dried and pulverized plants, were extracted succesively with ether and ethanol at room temperature and both extracts evaporated. The combined residues were fractionated by flash chromatography, RP-HPLC and prep. TLC rendering 1 and four more polar withanolides. Results and DiscussionThe 1H and 13C NMR spectra of compounds 2-5 showed resonances for rings C, D and the side chain, almost identical to those of jaborosalactone P (1); thus, the main difference among the five withanolides was established to be in the functionalization of rings A and B. Compound 3, differed from the other four in the multiplicity pattern of the olefinic protons H-2 and H-3 which corresponded to a 4-substituted withanolide. The presence of additional resonances asigned to an oxygenated CH in the 1H and 13C NMR spectra (δ 3.76 and 69.3 respectively) confirmed the 4β-hydroxy substitution. The epoxide, diol and clorohydrin substituents of 2, 4 and 5 were identified by comparison of the NMR spectra with similarly substituted withanolides and by MS. To this date, spiranoid withanolides con-taining a C-C bond between (C-12) and the side chain (C-23) have only been found in J. odonelliana, J. araucana and J. runcinata [1,2]. The spiranoid withanolide, jaborosalactone 1 [2], isolated from the latter species, showed antitumor activity in in vitro tests for induction of quinone reductase on mouse hepatoma cells (hepalclc7) [3]. AcknowledgementsWe thank CONICET (Argentina) and Universidad de Buenos Aires for financial support.References and NotesMonteagudo, E. S.; Oberti, J. C.; Gros, E. G.; Burton, G. Phytochemistry 1990, 29, 933–935. Cirigliano, A. M.; Veleiro, A. S.; Bonetto, G. M.; Oberti, J. C.; Burton, G. J. Nat. Prod. 1996, 59, 717–721. [CrossRef] Kinghorn, A.D. personal communication. Share and Cite MDPI and ACS Style Cirigliano, A.M.; Veleiro, A.S.; Oberti, J.C.; Burton, G. New Spiranoid Withanolides From Jaborosa Odonelliana. Molecules 2000, 5, 441-442. https://doi.org/10.3390/50300441 AMA Style Cirigliano AM, Veleiro AS, Oberti JC, Burton G. New Spiranoid Withanolides From Jaborosa Odonelliana. Molecules. 2000; 5(3):441-442. https://doi.org/10.3390/50300441 Chicago/Turabian Style Cirigliano, A. M., A. S. Veleiro, J. C. Oberti, and G. Burton. 2000. "New Spiranoid Withanolides From Jaborosa Odonelliana" Molecules 5, no. 3: 441-442. https://doi.org/10.3390/50300441 Find Other Styles Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view.