RQ3, A Natural Rebaudioside D Isomer, Was Obtained from Glucosylation of Rebaudioside A Catalyzed by the CGTase Toruzyme 3.0 L

• DOI: 10.1021/acs.jafc.9b02545
• Publication Date: 2019-06-18T09:20:32Z
• Authors: Qingbin Guo; Tongtong Zhang; Nifei Wang; Yongmei Xia; Zhuoyu Zhou; Jian-rong Wang; Xuefeng Mei
• Keywords: 0301 basic medicine; 03 medical and health sciences; Glycosylation; Isomerism; Molecular Structure; Glucosyltransferases; Tandem Mass Spectrometry; Biocatalysis; Glycosides; Diterpenes, Kaurane

In this study, a monoglucosyl rebaudioside A product was isolated from the mixture of glucosylated rebaudioside A obtained from the most reported and industrial used cyclodextrin glycosyl transferase, Toruzyme 3.0 L (CGTase, Toruzyme 3.0 L). The molecular structure of the monoglucosyl rebaudioside A was characterized using LC-MS/MS and methylation analysis combined with 1D and 2D NMR, indicating that it is 13-[(2-O-(3-α-O-D-glucopyranosyl)-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (also known as RQ3, which naturally exists in Stevia extract as an isomer of rebaudioside D). This study may help to further understand the reaction mechanism of glucosylation of steviol glycoside assisted by Toruzyme 3.0 L in the aspect of molecule linkage pattern, and also benefit the application of the glucosylated rebaudiosides.