New triterpene saponins from Phryna ortegioides |
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| Institution: | 1. Ege University, Faculty of Science, Department of Chemistry, Bornova, 35100 ?zmir, Turkey;2. University of Salerno, Department of Pharmacy, 84084 Fisciano, Salerno, Italy;3. Ege University, Faculty of Science, Department of Botany, Bornova 35100, ?zmir, Turkey;1. Yunnan Academy of Tobacco Agricultural Sciences, Kunming, Yunnan 650031, PR China;2. Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650231, PR China;3. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650031, PR China;1. Department of Mechanical and Industrial Engineering, Concordia University, 1455 de Maisonneuve Boulevard West, EV004.251, Montreal, Quebec, H3G 1M8, Canada;2. Research Centre for High Performance Polymer and Composite Systems (CREPEC), Canada;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 |
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| Abstract: | Four new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae.The structures of the new compounds were determined as gypsogenic acid 28-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (2), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-]-β-d-glucopyranosyl ester (3), 3-O-α-l-arabinofuranosyl-16α-hydroxyolean-12-en-23,28-dioic acid-28-O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (4). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family.The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC50 values of 77 and 52 μM, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number. |
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| Keywords: | Monotypic taxon Caryophyllaceae Triterpene saponins Gypsogenic acid |
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