Antioxidant, Free Radical–Scavenging, and NF-κB–Inhibitory Activities of Phytosteryl Ferulates: Structure–Activity Studies

Md. Shafiqul Islam; Hiroshi Yoshida; Naoaki Matsuki; Kenichiro Ono; Reiko Nagasaka; Hideki Ushio; Ying Guo; Toshiyuki Hiramatsu; Takamitsu Hosoya; Takahisa Murata; Masatoshi Hori; Hiroshi Ozaki

doi:10.1254/jphs.09146FP

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Antioxidant, Free Radical–Scavenging, and NF-κB–Inhibitory Activities of Phytosteryl Ferulates: Structure–Activity Studies

Md. Shafiqul Islam, Hiroshi Yoshida, Naoaki Matsuki, Kenichiro Ono, Reiko Nagasaka, Hideki Ushio, Ying Guo, Toshiyuki Hiramatsu, Takamitsu Hosoya, Takahisa Murata, Masatoshi Hori, Hiroshi Ozaki

Author information

Md. Shafiqul Islam
Department of Veterinary Pharmacology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Hiroshi Yoshida
Department of Veterinary Clinical Pathobiology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Naoaki Matsuki
Department of Veterinary Clinical Pathobiology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Kenichiro Ono
Department of Veterinary Clinical Pathobiology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Reiko Nagasaka
Department of Food Science and Technology, Tokyo University of Marine Science and Technology, Japan
Hideki Ushio
Department of Food Science and Technology, Tokyo University of Marine Science and Technology, Japan
Ying Guo
Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Japan
Toshiyuki Hiramatsu
Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Japan
Takamitsu Hosoya
Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Japan
Takahisa Murata
Department of Veterinary Pharmacology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Masatoshi Hori
Department of Veterinary Pharmacology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan
Hiroshi Ozaki
Department of Veterinary Pharmacology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Japan

Keywords: phytosteryl ferulate, cycloartenyl ferulate, NF-κB, antioxidant, reactive oxygen species (ROS)

JOURNAL FREE ACCESS

2009 Volume 111 Issue 4 Pages 328-337

DOI https://doi.org/10.1254/jphs.09146FP

View "Advance Publication" version (November 27, 2009).

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Abstract

Some of the pharmacological properties of phytosteryl ferulates may be linked to their antioxidant potential. In this study, 2,2-diphenyl-1-picrylhydrazyl (DPPH), electron spin resonance (ESR), and thiobarbituric acid–reactive substances (TBARS) assays demonstrated that phytosteryl ferulates such as cycloartenyl ferulate (CAF), 24-methylenecycloartanyl ferulate (24-mCAF), and β-sitosteryl ferulate (β-SF) and ferulic acid (FA) each exerted strong free radical scavenging and antioxidation of lipid membrane, which were comparable to α-tocopherol. However, the sterol moiety alone, such as cycloartenol (CA), had neither activity. Since, the reactive oxygen species (ROS) production in the cell complex defense mechanism cannot be ruled out with the cell free system, we measured ROS production in NIH 3T3 fibroblast cells induced by H₂O₂. CAF and ethyl ferulate (eFA) greatly decreased the ROS level in this system. CA also significantly inhibited the ROS level, suggesting that CA could inhibit ROS production in living cells. Besides these, CAF, 24-mCAF, β-SF, as well as eFA and CA, all these chemicals significantly inhibited the NF-κB activity as analyzed by measuring translocation of NF-κB p65 in LPS-stimulated RAW 264.7 macrophages. These observations revealed that phytosteryl ferulates are responsible for the antioxidant and anti-inflammatory activity via ROS scavenging and inhibition of ROS production.

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