Browsing by Author "Kyoto Prefectural University"

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    Chemopreventive and biological activities of Helicteres isora L. fruit extracts
    (2018-01-01) Acharaporn Rattanamaneerusmee; Krit Thirapanmethee; Yasushi Nakamura; Bhanubong Bongcheewin; Mullika Traidej Chomnawang; Mahidol University; Kyoto Prefectural University; Forestry and Fisheries Technology Center
    © 2018 Medknow Publications. All rights reserved. Helicteres isora L. (H. isora) has been used in traditional medicine in Asia. This study was aimed to determine biological activities of H. isora fruit extracts. Chemopreventive effect was examined by cell proliferation assay and differentiation-inducing effect. Anti-inflammatory activity of extracts was studied on the levels of nitric oxide (NO), tumor necrosis factor alpha (TNF-α), production of prostaglandin E2 (PGE-2), and cyclooxygenas-2 (COX-2). Cell proliferation assay revealed that H. isora extracts and its major compound, rosmarinic acid, showed no cytotoxicity in THP-1 and RCM-1 cells. Methylthio acetic acid from Cucumis melo var.conomon used as a positive control and 80% ethanol extracts demonstrated significant cell differentiation induction. Hexane extract of H. isora could lower the levels of TNF-α, PGE-2, and NO in THP-1 cells with 51.61 ± 0.79%, 69.68 ± 0.017%, and 69.93 ± 9.41% inhibition, respectively. The highest inhibitory effect on COX-2 was obtained from dichloromethane extract. Dexamethasone inhibited the secretion of TNF-α with 95.82 ± 0.50% while celecoxib showed the inhibitory effect on COX-2 and PGE-2 with 100% and 99.86%, respectively. The ethanol extract showed the best antioxidant activity by DPPH and FRAP assays at IC 50 of 5.43 ± 1.01 μg/mL and 22.83 ± 0.13 mmol FeSO 4 /g sample, respectively, while the positive control, trolox, showed the antioxidant activity with IC 50 and FRAP values at 4.08 ± 0.85 μg/mL and 10.84 ± 0.04 mmol FeSO 4 /g sample, respectively. Taken together, H. isora possess chemopreventive and antioxidant activity. Further studies on in vivo activities of this plant are suggested.
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    Differentiation-inducing effect in human colon cancer cells of essential oils
    (2018-07-01) A. Rattanamaneerusmee; K. Thirapanmethee; Y. Nakamura; M. T. Chomnawang; Mahidol University; Kyoto Prefectural University; Forestry and Fisheries Technology Center
    © 2017. Essential oils are naturally occurring, volatile aromatic compounds. Many essential oils are suitable for use as flavoring agents and are safe for human consumption. In this study, the effects of essential oils on colon cancer cell differentiation were evaluated. Essential oils regularly used as food ingredients were selected for investigation. These included betel vine oil, citronella oil, clove oil, clove leaf oil, galangal oil, guava leaf oil, hairy basil oil, holy basil oil, kaffir lime oil, lemongrass oil, lesser galangal oil, lime oil, sweet basil oil, and turmeric oil. Human rectum adenocarcinoma cells (RCM-1) was a study model for cell differentiating induction. The result showed that most essential oils were able to induce call differentiation except lemongrass oil and lime oil which showed lower fractions of duct formation index (FFI) than 3-methylthiopropionic acid ethyl ester (MTPE), the positive control from Japanese pickling melon. Hairy basil oil, holy basil oil, and guava leaf oil were highly effective in inducing cell differentiation effect with FFIQ 4.71 ± 0.20, 4.03 ± 0.26, and 3.81 ± 1.05, respectively. The effect of inducing differentiation was interpreted by compared with the FFI of MTPE. Our finding indicated no dose dependent manner in this study. Interestingly high concentration of some essential oils exhibited cytotoxicity on colon cancer cells. The results of this study can be used as preliminary data for further study on novel chemoprevetative agents, with less adverse effects.
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    Differentiation-inducing effect of piperitenone oxide, a fragrant ingredient of spearmint (Mentha spicata), but not carvone and menthol, against human colon cancer cells
    (2014-01-01) Yasushi Nakamura; Yuki Hasegawa; Koji Shirota; Noboru Suetome; Takako Nakamura; Mullika Traidej Chomnawang; Krit Thirapanmethee; Piyatip Khuntayaporn; Panida Boonyaritthongchai; Chalermchai Wongs-Aree; Shigehisa Okamoto; Tomoaki Shigeta; Tomoaki Matsuo; Eun Young Park; Kenji Sato; Kyoto Prefectural University; Forestry and Fisheries Technology Center; Mahidol University; King Mongkuts University of Technology Thonburi; Kagoshima University
    The n-hexane extract from spearmint (Mentha spicata) leaves was purified via a bioassay-guided fractionation scheme, which was based on the induction of differentiation in a RCM-1 human colon cancer cell line. One of the criteria of a differentiation marker is the formation of ducts determined visually using phase contrast microscopy, the most potent fraction contained piperitenone oxide, based on EI-MS, 1H-NMR and 13C-NMR spectra. Previously, the role of piperitenone oxide was considered as an odor producing compound in spearmint cultivars, but this study indicates the potential medical benefits of this compound. The effective dose of piperitenone oxide was lower than that of any differentiation-inducers found in the bioassay. Piperitenone oxide was categorized into monoterpene such as carvone and menthol, which are also familiar ingredients in Mentha genus plants. However, carvone and menthol did not possess the differentiation-inducing effect. © 2014 Elsevier Ltd.
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    Investigation on the epoxidation of piperitenone, and structure-activity relationships of piperitenone oxide for differentiation-inducing activity
    (2020-01-01) Ryohei Sato; Azusa Sasaki; Yuko Mori; Mio Komai; Shogo Kamo; Mai Onuki; Takafumi Seki; Zen Kawabe; Shu Miyajima; Shusuke Tomoshige; Tsuneomi Kawasaki; Shuichi Sato; Takako Nakamura; Nakao Kubo; Seiji Takeda; Shuichi Date; Shigehisa Okamoto; Panida Boonyaritthongchai; Krit Thirapanmethee; Mullika Traidej Chomnawang; Bhanubong Bongcheewin; Thuy Linh Nguyen; Huong Lan Thi Nguyen; Huong Thi Le; Yasushi Nakamura; Kouji Kuramochi; Hanoi Medical University; Kagoshima University; Tokyo University of Science; Mahidol University; King Mongkut s University of Technology Thonburi; Kyoto Prefectural University
    © 2020 by Japan Oil Chemists’ Society. Piperitenone oxide, a major chemical constituent of the essential oil of spearmint, Mentha spicata, induces differentiation in human colon cancer RCM-1 cells. In this study, piperitenone oxide and trans-piperitenone dioxide were prepared as racemic forms by epoxidation of piperitenone. The relative configuration between two epoxides in piperitenone dioxide was determined to be trans by1H NMR analysis and nuclear Overhauser effect spectroscopy (NOESY) in conjunction with density functional theory (DFT) calculations. Optical resolution of (±)-piperitenone oxide by high-performance liquid chromatography (HPLC) using a chiral stationary phase (CSP) afforded both enantiomers with over 98% enantiomeric excess (ee). Evaluation of the differentiation-inducing activity of the synthetic compounds revealed that the epoxide at C-1 and C-6 in piperitenone oxide is important for the activity, and (+)-piperitenone oxide has stronger activity than (–)-piperitenone oxide. The results obtained in this study provide new information on the application of piperitenone oxide and spearmint for differentiation-inducing therapy. Furthermore, natural piperitenone oxide was isolated from M. spicata. The enantiomeric excess of the isolated natural piperitenone oxide was 66% ee. Epoxidation of piperitenone with hydrogen peroxide proceeded in a phosphate buffer under weak basic conditions to give (±)-piperitenone oxide. These results suggest that the nonenzymatic epoxidation of piperitenone, which causes a decrease in the enantiomeric excess of natural piperitenone oxide, is accompanied by an enzymatic epoxidation in the biosynthesis of piperitenone oxide.