Investigation on the Epoxidation of Piperitenone, and Structure-activity Relationships of Piperitenone Oxide for Differentiation-inducing Activity

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  • Sato Ryohei
    Department of Applied Biological Science, Tokyo University of Science
  • Sasaki Azusa
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Mori Yuko
    Department of Applied Biological Science, Tokyo University of Science
  • Komai Mio
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Kamo Shogo
    Department of Applied Biological Science, Tokyo University of Science
  • Onuki Mai
    Department of Applied Biological Science, Tokyo University of Science
  • Seki Takafumi
    Department of Applied Chemistry, Tokyo University of Science
  • Kawabe Zen
    Department of Applied Biological Science, Tokyo University of Science
  • Miyajima Shu
    Department of Applied Biological Science, Tokyo University of Science
  • Tomoshige Shusuke
    Department of Applied Biological Science, Tokyo University of Science
  • Kawasaki Tsuneomi
    Department of Applied Chemistry, Tokyo University of Science
  • Sato Shuichi
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Nakamura Takako
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Kubo Nakao
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Takeda Seiji
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Date Shuichi
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University
  • Okamoto Shigehisa
    The United Graduate School of Agricultural Sciences, Kagoshima University
  • Boonyaritthongchai Panida
    School of Bioresources and Technology, King Mongkut’s University of Technology Thonburi
  • Thirapanmethee Krit
    Department of Microbiology, Faculty of Pharmacy, Mahidol University
  • Chomnawang Mullika Traidej
    Department of Microbiology, Faculty of Pharmacy, Mahidol University
  • Bongcheewin Bhanubong
    Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University
  • Nguyen Thuy Linh
    Institute for Preventive Medicine and Public Health, Hanoi Medical University
  • Nguyen Huong Lan Thi
    Institute for Preventive Medicine and Public Health, Hanoi Medical University
  • Le Huong Thi
    Institute for Preventive Medicine and Public Health, Hanoi Medical University
  • Nakamura Yasushi
    Graduate School of Life and Environmental Sciences, Kyoto Prefectural University Faculty of Letters, Kyoto Prefectural University
  • Kuramochi Kouji
    Department of Applied Biological Science, Tokyo University of Science

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Abstract

<p>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 by 1H 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.</p>

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