Publication: Investigation on the epoxidation of piperitenone, and structure-activity relationships of piperitenone oxide for differentiation-inducing activity
Issued Date
2020-01-01
Resource Type
ISSN
13473352
13458957
13458957
Other identifier(s)
2-s2.0-85089206363
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Oleo Science. Vol.69, No.8 (2020), 951-958
Suggested Citation
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 Investigation on the epoxidation of piperitenone, and structure-activity relationships of piperitenone oxide for differentiation-inducing activity. Journal of Oleo Science. Vol.69, No.8 (2020), 951-958. doi:10.5650/jos.ess19278 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/57798
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Title
Investigation on the epoxidation of piperitenone, and structure-activity relationships of piperitenone oxide for differentiation-inducing activity
Author(s)
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
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
Abstract
© 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.