The phytochemical investigation of resulted in the isolation of 15 previously undescribed triterpenoids (desmondiins A, C-P) and 8 already described compounds. The structures of the isolated compounds were determined by extensive spectroscopic analyses. The compounds were identified as tirucallane and euphane triterpenes based on 7-keto-8-ene, 11-keto-8-ene, or 7,11-diketo-8-ene skeletons. Additionally, the selective trypanocidal activities of these compounds against were evaluated. Desmondiins A, C, D, F, H, and M exhibited IC values in the range of 3-5 μM, and selectivity indices between 5-9, against epimastigotes over the host cell (RAW264.7 macrophages). Furthermore, desmondiin A efficiently inhibited amastigote replication in host cells (IC = 2.5 ± 0.3 μM), which was comparable to that of the positive control, benznidazole (3.6 ± 0.4 μM). Overall, the isolated euphane and tirucallane triterpenoids could act as antichagasic lead scaffolds.
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http://dx.doi.org/10.1021/acs.jnatprod.4c00730 | DOI Listing |
J Nat Prod
September 2024
Department of Pharmacognosy, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary.
The phytochemical investigation of resulted in the isolation of 15 previously undescribed triterpenoids (desmondiins A, C-P) and 8 already described compounds. The structures of the isolated compounds were determined by extensive spectroscopic analyses. The compounds were identified as tirucallane and euphane triterpenes based on 7-keto-8-ene, 11-keto-8-ene, or 7,11-diketo-8-ene skeletons.
View Article and Find Full Text PDFOrg Lett
August 2023
Department of Chemistry, Burke Laboratory, Dartmouth College, Hanover, New Hampshire 03755, United States.
Asymmetric syntheses of euphol and tirucallol have been accomplished by way of a concise sequence of chemical steps featuring several modern stereoselective transformations. The preparative solution described for these complex problems in natural product synthesis departs significantly from biomimetic polyene cyclization chemistry, which has been leveraged to address related tetracyclic triterpenoid targets. In particular, a diastereoselective Friedel-Crafts-type cyclization was employed to establish a tetracycle bearing a stereodefined quaternary center at C9 (steroid numbering) that provided access to intermediates of relevance for introducing the C10 and C14 quaternary centers by sequential stereospecific 1,2-alkyl shifts (C9 → C10 and C15 → C14).
View Article and Find Full Text PDFFront Chem
June 2023
National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan.
The Euphorbiaceae plant L. is distributed widely in India, Thailand, Southeastern China, and Taiwan and used as a carminative and expectorant to treat several inflammation-related diseases, such as gonorrhoea, asthma, and cancer. In the course of our search for potential anti-inflammatory agents from the titled plant, 11 triterpenes from the stem of were isolated and reported in our previous endeavor.
View Article and Find Full Text PDFPhytochemistry
July 2022
Division of Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, 112026, Taiwan; Ph.D. Program in Clinical Drug Development of Herbal Medicine, College of Pharmacy, Taipei Medical University, Taipei, 110301, Taiwan; Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, 404333, Taiwan. Electronic address:
Euphorbia neriifolia L. is widely distributed in India, Thailand, and China and has been used to treat diseases such as rotten sores and asthma as well as for its antidiabetic and anticancer effects. In this study, seven undescribed triterpenes, including six euphanes, neritriterpenols A-B and D-G, and a tirucallane, neritriterpenol C, together with four known triterpenes, were isolated from ethanolic extracts of E.
View Article and Find Full Text PDFFitoterapia
June 2019
BioCIS, Université Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France. Electronic address:
The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports.
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