Furanoeremophilanes inSenecio filaginoidesandS. pinnatus

Abstract

Aerial parts of Senecio filaginoides yielded two new furanoeremophilane type sesquiterpenoids: 6alpha-acetyloxy-10betaH-furanoeremophil-1-one, 1 and 6alpha-tiglinoyloxy-10betaH-furanoerernophil-1-one, 2. Their structures have been elucidated by spectroscopic data. From roots and aerial parts of S. pinnatus 1alpha-hydroxy-6betaangeloyloxy-10alphaH-furanoeremophil-9-one, 3 has been isolated.

Constituents of Senecio chionophilus with Potential Antitubercular Activity

“…Twenty-one known compounds were isolated from the n-hexane-and dichloromethane-soluble extracts of the above-ground biomass and roots of S. chionophilus, as described in the Experimental Section, and were identified as 6β-angeloyloxy-1R-hydroxy-10RH-9-oxofuranoeremophilane (3), 10 1R-hydroxy-6β-isovaleryloxy-10RH-9-oxofuranoeremophilane (4), 11 1R-hydroxy-6β-isobutyryloxy-10RH-9-oxofuranoeremophilane (5), 7 4′-hydroxyacetophenone (6), 12 1R-acetoxy-6β-angeloyloxy-10RH-9-oxofuranoeremophilane, 6 1R-acetoxy-6β-isobutyryloxy-10RH-9-oxofuranoeremophilane, 13 R-amyrenone, 14 β-amyrenone, 14 R-amyrin, 14 β-amyrin, 14 1R-angeloyloxy-6β-isobutyryloxy-10RH-9-oxofuranoeremophilane, 13 6β-angeloyloxy-10RH-9-oxofuranoeremophilane, 6 caryophyllene 4β,5R-epoxide, 15 daucosterol, 16 1R-hydroxy-6β-propionyloxy-10RH-9-oxofuranoeremophilane, 17 6β-isobutyryloxy-10RH-9-oxofuranoeremophilane, 6 lupenone, 14 lupeol, 14 β-sitosterol, 18 taraxasterol, 14 and taraxasterone, 14 by comparison of their physical and spectroscopic data (mp, [R] D , 1 H NMR, 13 C NMR, DEPT, 2D NMR, and MS) with reported data. The 13 C NMR data of 4 and its acetate (4a) along with 5 have not been published; thus the complete assignments of their 13 C NMR data were performed and are reported in Table 2.…”

“…Fractionation of fraction 5-3 (300 mg) by MPLC (MeOH-H2O, 50: 50, 1.7 mL/min, 4 L) sequentially resulted in the purification of 1 (20 mg), 1R-hydroxy-6β-isobutyryloxy-10RH-9-oxofuranoeremophilane (5, 65 mg), 6β-angeloyloxy-1R-hydroxy-10RH-9oxofuranoeremophilane (3, 30 mg), 2 (6 mg), and 1R-hydroxy-6β-isovaleryloxy-10RH-9-oxofuranoeremophilane (4, 10 mg). In turn, the CH 2Cl2 extract (5.0 g) was subjected to Sephadex LH-20 CC by elution with MeOH to obtain four pooled fractions (7)(8)(9)(10). Fraction 8 (1.…”

GC-FID-MS and X-ray Diffraction for the Detailed Evaluation of the Volatiles From Senecio filaginoides

“…Meanwhile, from the roots and aerial parts of S. pinnatus, 11 1α-hydroxy-6β-angeloyloxy-10αHfuranoeremophil-9-one was isolated and identified using the same methods. 11 Thus, both Senecio species gave furanoeremophilane derivatives with different C-10 stereochemistry than that specified herein. In addition, Bisht et al 21 could confirm the 1,10β-epoxy-6oxofuranoeremophilane configuration for the main Senecio royleanus constituent using X-ray diffraction (XRD) analysis.…”

“…Other studies were performed on nonpolar extracts providing a furanoeremophilone as the main compound, which was identified as 10βH-furanoeremophil-1-one by Bohlmann et al, 9 who named it as senberginone, and later Arancibia et al 10 identified the 10αH-furanoeremophil-9-one isomer by nuclear magnetic resonance (NMR) spectroscopy. Two other furanoeremophilane-type sesquiterpenoids, 6α-acetyloxy-10βH-furanoeremophil-1-one and 6α-tigloyloxy-10βHfuranoerermophil-1-one, were also isolated from this species 11 although Bohlman et al 9,12 suggested the 6β orientation for these molecules by nuclear overhauser effect differences spectroscopy.…”

Revisiting the absolute chirality and polymorphism of (–)-Istanbulin A

“…The genus Senecio (Asteraceae) is widely distributed throughout the world, except for Antarctica and Amazonas, and includes more than 3000 species. It is well known that the Senecio species are used in folk medicine; their properties are attributed to their essential oils and secondary metabolites (Arancibia et al, 2010(Arancibia et al, , 2018El Hawary et al, 2008;Yang et al, 2011;Singab et al, 2013;Bohlmann et al, 1986;Romo de Vivar et al, 2007;Juarez et al, 1995;Xu et al, 2010;de Salmeron et al, 1983). Senecio filaginoides DC is one of the about 300 species which occurs in Argentina, growing from the Jujuy (north) to Santa Cruz provinces (south).…”