Jatrophenediol, a pseudoguaiane sesquiterpenoid from Jatropha dioica rhizomes

• Published in: Tetrahedron letters Vol. 104; pp. 154040 - 154042
• Main Authors: Bautista, Elihú, Lozano-Gamboa, Sarahí, Fragoso-Serrano, Mabel, Rivera-Chávez, José, Salazar-Olivo, Luis A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.08.2022; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Euphorbiaceae; Jatropha species; MDR modulation; Physical Sciences; Science & Technology; Sesquiterpenoids; Structural elucidation; MDR modulation; Structural elucidation; Euphorbiaceae; Jatropha species; Sesquiterpenoids; SYSTEM; DITERPENOIDS; MODULATORS; MULTIDRUG-RESISTANCE; DERIVATIVES; DISCOVERY
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2022.154040

[Display omitted] •A novel sesquiterpenoid was identified in Jatropha dioica roots.•Its structure was determined by HRMS and NMR.•The cytotoxic and MDR modulatory capability of the isolates was assayed. Jatrophenediol (1), a new pseudoguaiane sesquiterpenoid was isolated from the roots of Jatropha dioica, together with the known diterpenoids citlalitrione (2) and jatropolones A and B (3 and 4). The structure of 1 was established based on the analysis of its spectroscopic (1D/2D NMR) and spectrometric (HRESIMS) data. The cytotoxic effect of all isolates was assayed against a panel of six cancer cell lines (HeLa, MCF-7, PC-3, HCT-15, HCT-116, and RAW 264.7). Unfortunately, no cytotoxicity was detected for compounds 1–4. Additionally, the reversion of multi-drug-resistance (MDR) to vinblastine was explored in three phenotypes of the MCF-7 line. Interestingly, the mixture of compounds 3/4 in three different ratios at 25 μg/mL increased the sensitivity to vinblastine by 7–10-fold.