Analysis of steryl glucosides in rice bran-based fermented food by LC/ESI-MS/MS

• Published in: Steroids Vol. 158; p. 108605
• Main Authors: Murai, Tsuyoshi, Jin, Shigeki, Itoh, Mari, Horie, Yukiko, Higashi, Tatsuya, Ikegawa, Shigeo
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01-06-2020
• Subjects: Acylated steryl glucoside; Aspergillus oryzae; Chromatography, Liquid; Fermentation; Fermented Foods and Beverages - analysis; Glycosides - analysis; Glycosides - metabolism; LC/ESI-MS/MS; Molecular Conformation; Oryza - chemistry; Oryza - metabolism; Rice bran; Spectrometry, Mass, Electrospray Ionization; Sterols - analysis; Sterols - metabolism; Steryl glucoside; Tandem Mass Spectrometry; ASGs; mp; EI; Steryl glucoside; 1H NMR; Acylated steryl glucoside; FBRA; Fermentation; SRM; RB; BR; Aspergillus oryzae; LR-MS; RM; A. oryzae; SGs; LC/ESI-MS/MS; Rice bran
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2020.108605

•Four steryl glucosides (SGs) were synthesized using Köenigs-Knorr reaction.•An LC/ESI-MS/MS method was developed for determination of SGs.•SGs in rice bran-based fermented food were determined by the developed method.•Fermentation brought the decrease of steryl glucoside contents.•Fermentation brought the increase of acylated steryl glucoside contents.
Steryl glucosides (SGs) and acylated steryl glucosides (ASGs) are phytochemicals found in plant-based foods and are known as bioactive compounds with potential health benefits. These include anti-inflammatory properties, anti-diabetic effects, and modulation of immunoregulatory functions as well as having cholesterol lowering effects. In this study, three major SGs, i.e., glucosides of β-sitosterol, stigmasterol, and campesterol, were synthesized and used as standards for measurement of their contents in rice bran (RB)-based fermented food (FBRA) utilizing Aspergillus oryzae and raw material (RM). The compounds were quantified using liquid chromatography/electrospray ionization-tandem mass spectrometry. It was found that β-sitosteryl glucoside was most abundant among the analyzed glucosides in both samples, and the contents of each SG in FBRA decreased about 35% from those of RM. In contrast to SGs, the contents of ASGs in FBRA increased 1.5-fold during the fermentation process as evidenced by an alkaline hydrolysis. The present results suggest that the FBRA might have greater beneficial effects than the RM, since ASGs have shown to have more potent cholesterol lowering effects and stronger anti-diabetic properties than SGs.