Cytotoxic activities of sesquiterpenoids from the aerial parts of Petasites japonicus against cancer stem cells
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ORIGINAL PAPER
Cytotoxic activities of sesquiterpenoids from the aerial parts of Petasites japonicus against cancer stem cells Takahiro Matsumoto1 · Daisuke Imahori1 · Youhei Saito2 · Wei Zhang1 · Tomoe Ohta3 · Tatsusada Yoshida3 · Yuji Nakayama2 · Eishi Ashihara4 · Tetsushi Watanabe1 Received: 21 April 2020 / Accepted: 2 June 2020 © The Japanese Society of Pharmacognosy 2020
Abstract Abstract From the methanolic extract of the aerial parts of Petasites japonicus, six new eremophilane-type sesquiterpenoids, petasitesterpenes I–VI were isolated together with eight known compounds including S-japonin and eremophilenolide. The chemical structures of the isolated new compounds were elucidated based on chemical/physicochemical evidence. For petasitesterpenes I and II, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Among the isolated compounds, petasitesterpenes I, II, VI, and S-japonin showed cytotoxic activity against both human astrocytoma U-251MG cancer cells (non-CSCs) and their cancer stem cells (CSCs) isolated by sphere formation. In addition, cytotoxic activities of these compounds against breast cancer MDA-MB-231 were evaluated, supporting that petasitesterpene II has more effective than other isolated compounds. Graphic abstract
Cytotoxic activities of petasitesterpenes against U-251 MG Cancer Stem Cells Petasites japonicus
petasitesterpene I
petasitesterpene II
Keywords Petasites japonicus · Petasitesterpene · ECD · Cancer stem cell
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11418-020-01420-x) contains supplementary material, which is available to authorized users. * Tetsushi Watanabe [email protected]‑phu.ac.jp Extended author information available on the last page of the article
The plant of Petasites japonicus (Sieb. Et Zucc.) Maxim, belonging to the Compositae family, has been cultivated as a vegetable in Japan. The rhizomes or the whole plants of P. japonicus has also been utilized as a folk medicine for the treatment of furunculosis, contusion, wounds, and
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snakebites [1]. As the constituents of P. japonicus, otonecine-type pyrrolizidine alkaloids from whole plants [2] and eremophilane-type sesquiterpenoids from aerial parts [3] and rhizomes [1, 4, 5] have been isolated and reported. The eremophilane-type sesquiterpenoids were well-known bioactive compounds such as cytotoxic activities against HEPG2, MGC-803, and S-180 cancer cell lines [6], activation effects on AMP-activated protein kinase [7], and inhibitory effects on NF-κB-induced gene expression [8], cyclooxygenase-2 [9], and lipopolysaccharide-induced NO production in microglia-derived BV2 cells [10]. Interestingly, few sesquiterpenoids from P. japonicus contain sulfur atoms [11]. As part of an ongoing research program for the discovery of new cancer-treatment [12] and cancer-privation agents [13–17], we isolated the eremophilane-type sesquiterpenoids of P. jap
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