A spiranic withanolide from Jaborosa odonelliana

Spiranoid Withanolides from Jaborosa odonelliana and Jaborosa runcinata

“…The compounds isolated from J. odonelliana presented a 17,22-diol functionality and a 23S stereochemistry at the spiranoid center (e.g. Jaborosalactone P, 1) [5], while those isolated from J. runcinata and J. araucana showed a 17(20)-ene-22-keto system and a 23R stereochemistry (e.g. Jaborosalactone 2, 2) [6], in agreement with that found in 1.…”

“…The HREIMS showed a molecular ion corresponding to the formula C 28 H 36 O 6 , whereas the EIMS showed peaks at m/z 299 (42) and 168 (31) corresponding to the cleavage between C-20-C-17 and C-23-C-12, distinctive for this type of structure [8]. 1 H and 13 C NMR chemical shift values in jaborosalactone 24 (3) were closely related to those reported for jaborosalactone P (1) [5]. In the low-field end of the 1 H NMR spectrum signals at δ = 5.81, 6.73 and 5.56 were assigned to H-2, H-3 and H-6, respectively, of a 1-oxo-2,5-dienewithanolide.…”

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

“…2,3-Dihydrowithaferin A (75) Ie, 13a, 13e, 13e (2) 2,3-Dihydro-5,6-deoxywithaferin A (115) Ie (27a) 2,3-Dihydro-27-deoxywithaferin A (76) Ie (27a) 24,25-Dihydro-27 -deoxywithaferin A (116) Ie,13e (183) 14cx-Hydroxy-27-deoxywithaferin A (66) 13e (181) 17cx-Hydroxy-27-deoxywithaferin A (67) 13e (184) (96) l3e (196,202) (186,187) Withanolide Y (129) 13e (177) Withanone (12) 13e (184) 141X-Hydroxywithanone (13) 13e (197) 14~-H ydroxywithanone (14) 13e (197) Withastramonolide (15) 2f,2h (51) 12-Deoxywithastramonolide ( = 27-Hydroxywithanolide B) (16) 2c, 13e (39,184) 41X-27-Dihydroxy-5~,6~-epoxy-…”

New Spiranoid Withanolides From Jaborosa Odonelliana

“…The presence of additional resonances asigned to an oxygenated CH in the 1 H and 13 C 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 containing 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].…”

“…As part of our studies of the withanolides of argentine species of the genus Jaborosa we have reinvestigated 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.…”