Chemical constituents of Ligularia alticola Worosch. leaves and their biological activities |
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| Affiliation: | 1. Grupo de Investigacion en Sustancias Bioactivas, Facultad de Ciencias Farmaceuticas y Alimentarias, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellin, Colombia;2. Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II, 84084 Fisciano, SA, Italy;3. Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy;4. Centro Interdipartimentale di Ricerca “Nutraceutica e Alimentazione per la Salute”, Università di Pisa, via del Borghetto 80, 56124 Pisa, Italy;1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, People’s Republic of China;2. Jiangsu Provincial Key Laboratory for TCM Evaluation and Translational Development, School of TCM, China Pharmaceutical University, Nanjing 211198, People’s Republic of China;1. Department of Pharmaceutical Botany, Faculty of Pharmacy, Ege University, 35100 Bornova-Izmir, Turkey;2. Department of Bioengineering, Faculty of Engineering, Ege University, 35100 Bornova-Izmir, Turkey;1. Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun 666303, PR China;2. University of Chinese Academy of Sciences, Beijing 100049, PR China;3. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China;4. School of Pharmacy, Guiyang Medical College, Guiyang 550004, PR China;5. Engineering Research Center for the Development and Application of Ethnic Medicine and TCM, Ministry of Education, Guiyang 550004, PR China;1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoku 159, Vladivostok 690022, Russian Federation;2. Far Eastern Federal University, Suhanova Street 8, Vladivostok 690950, Russian Federation;3. Institute of Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-letiya Vladivostoku 159, Vladivostok 690022, Russian Federation |
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| Abstract: | Seven eremophilane-type sesquiterpenes (1–7), six cycloartane derivatives (8–13) and α-amyrin acetate (14) were isolated from the leaves of the far-eastern plant Ligularia alticola Worosch. (Family Asteraceae). (4S,5R,8S,10R)-8-Ethoxyeremophil-7(11)-en-12(8)-olide (1), 8α,11-epidioxy-8β-methoxyeremophil-6-ene (2) and 29-norcycloartan-3α-ol (8) have not been previously reported. Fukinone α-epoxide (3) was isolated for the first time from a natural source. The structures of all the compounds were established by the extensive analysis of their 1D and 2D NMR spectra and HR ESI mass spectrometry. The absolute stereochemistry of 1 was determined by comparison of theoretical and experimental ECD spectra with the application of B3LYP-TDDFT and B3LYP-GIAO calculations as well as by NMR spectroscopy. Compound 1 showed cytotoxic action against human cancer HL-60, Raji, and THP-1 cell lines (IC50 12.6, 6.0 and 6.9 μM, respectively). Compounds 2 and 4 demonstrated significant cytotoxic activities against HL-60 (IC50 2.8 and 5.8 μM, respectively) and Raji cells (IC50 2.9 and 4.2 μM, respectively). Compound 6 was cytotoxic against Raji cells (IC50 4.6 μM). None of tested compounds were cytotoxic against RAW 264.7 cells. Compounds 1 and 4–7 significantly decreased intracellular ROS levels, induced by endotoxic LPS from Escherichia coli in RAW 264.7 murine macrophages. |
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| Keywords: | Eremophilane-type sesquiterpenes 4,14-Dimethylsteroids B3LYP Cytotoxicity Anti-inflammatory activity |
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