Isolation and structural elucidation of unique γ-oryzanol species in rice bran oil

Kazue Sawada; Takuya Nakagami; Halida Rahmania; Midori Matsuki; Junya Ito; Tomoyo Mohri; Yusuke Ogura; Shigefumi Kuwahara; Hiroyuki Hashimoto; Kiyotaka Nakagawa

doi:10.1016/j.foodchem.2020.127956

Isolation and structural elucidation of unique γ-oryzanol species in rice bran oil

Food Chem. 2021 Feb 1:337:127956. doi: 10.1016/j.foodchem.2020.127956. Epub 2020 Sep 3.

Authors

Affiliations

¹ Tsuno Food Industrial Co., Ltd., Ito, Wakayama 649-7194, Japan; Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi 980-8572, Japan.
² Tsuno Food Industrial Co., Ltd., Ito, Wakayama 649-7194, Japan.
³ Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi 980-8572, Japan.
⁴ Applied Bioorganic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi 980-8572, Japan.
⁵ Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
⁶ Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi 980-8572, Japan. Electronic address: kiyotaka.nakagawa.c1@tohoku.ac.jp.

PMID: 32919269
DOI: 10.1016/j.foodchem.2020.127956

Abstract

Even though γ-oryzanol (OZ) such as 24-methylenecycloartanyl ferulate (24MCAFA) is abundant in purified rice bran oil, we realized that the oil contained the prospect of two additional novels of OZ species. To identify this, we isolated and analyzed their chemical structures by using HPLC-UV-MS, NMR, and IR. We revealed for the first time that the oil had also contained cyclobranyl ferulate (CBFA) and cyclosadyl ferulate (CSFA) which are likely to be exist due to the isomerism of 24MCAFA under acid condition. OZ profile including CBFA and CSFA was roughly similar between commercial rice bran oils and processed foods containing the oils, suggesting that people might have often consumed CBFA and CSFA from rice bran oils and/or processed foods. Since different OZ species are known to have different functionality, this study opens the chance to explore more the contribution of CBFA and CSFA for human health and wellness.

Keywords: 24-methylenecycloartanyl ferulate; Cyclobranyl ferulate; Cyclosadyl ferulate; Processed foods containing rice bran oil; Rice bran oil; γ-Oryzanol.

MeSH terms

Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Phenylpropionates / chemistry*
Phenylpropionates / isolation & purification
Rice Bran Oil / chemistry*

Substances

Phenylpropionates
Rice Bran Oil
gamma-oryzanol