In this work we investigated mixtures from α-glycosylation of rubusoside with cyclodextrin glycosyltransferases. In addition to the previously known α-1,4 glycosylated derivatives, nine new compounds with rare α-1,3-glycosidic bonds were identified based on nuclear magnetic resonance spectroscopy and mass spectrometric analysis. Furthermore, sensory properties of monoglycosylated rubusoside derivatives were investigated and compared to previously described monoglycosylated compounds. Additionally, digestion with α-amylase from human saliva was investigated for different glycosylated rubusoside derivatives.
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http://dx.doi.org/10.1016/j.foodchem.2022.135033 | DOI Listing |
J Food Sci
November 2024
School of Food and Biological Engineering, Jiangsu University, Zhenjiang, China.
So far, the use of artificial low-calorie sweeteners, like sucralose, saccharin, and so on, to replace the conventional-based sugars has not succeeded due to the long-term adverse health effects, for example, hypertension, and not well-known safety stand. In this review, we discussed the next generation SvGl (rebaudioside M [Reb M]), their biosynthetic pathway in plant, high-yield production via microbial fermentation and enzyme engineering, physicochemical properties, taste modification, kinetic metabolism, application in food and beverages, safety and toxicological evaluation, regulation and dosage recommendation, and health benefits. In stevia, the biosynthesis of stevia glycosides, especially Reb M, is derived from the bifurcation of the pathway leading to gibberellin, followed by subsequent enzymatic modification of rubusoside.
View Article and Find Full Text PDFFood Chem
April 2023
Institute of Food Chemistry, Schleinitzstraße 20, 38106 Braunschweig, Germany.
In this work we investigated mixtures from α-glycosylation of rubusoside with cyclodextrin glycosyltransferases. In addition to the previously known α-1,4 glycosylated derivatives, nine new compounds with rare α-1,3-glycosidic bonds were identified based on nuclear magnetic resonance spectroscopy and mass spectrometric analysis. Furthermore, sensory properties of monoglycosylated rubusoside derivatives were investigated and compared to previously described monoglycosylated compounds.
View Article and Find Full Text PDFJ Agric Food Chem
December 2022
College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China.
Five plant-derived uridine diphosphate glycosyltransferases (UGTs) that catalyzed the glucosylation of stevia glycosides (SGs) were uncovered as the result of sequence mining considering the catalytic residues and conserved motifs of the known UGTs. Thereinto, UGT from with high activity toward rubusoside has been enzymatically characterized. The recombinant UGT was demonstrated to catalyze the β-1,6-glucosylation at C19 of rubusoside, producing a monoglucosyl derivative 13-[(-β-d-glucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-[(6--β-d-glucopyranosyl-β-d-glucopyranosyl) ester], which was then submitted to a β-1,2-glucosylation by UGT, resulting in a diglucosyl derivative 13-[(-β-d-glucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-[(2--β-d-glucopyranosyl-6--β-d-glucopyranosyl-β-d-glucopyranosyl) ester].
View Article and Find Full Text PDFEnzyme Microb Technol
January 2022
Department of Food Science & Technology, Chonnam National University, Gwangju 61186, Republic of Korea. Electronic address:
Rubusoside, which is used as a natural sweetener or a solubilizing agent for water-insoluble functional materials, is currently expensive to produce owing to the high cost of the membrane-based technologies needed for its extraction and purification from the sweet tea plant (Rubus suavissimus S. Lee). Therefore, this study was carried out to screen for lactic acid bacteria that possess enzymes capable of bio-transforming stevioside into rubusoside.
View Article and Find Full Text PDFJ Agric Food Chem
September 2020
Eurofins Supplement Analysis Center, Eurofins Scientific, Inc., 1365 Redwood Way, Petaluma, California 94954, United States.
Steviol glycosides, obtained from leaves of Bertoni (stevia) or produced via bioconversion and biosynthesis, are diterpenes used by the food/dietary supplement industry as zero-calorie sweeteners derived from natural sources. JECFA 2017 is the most updated international standardized method but it runs for 80 min per sample with suboptimal separations on several critical pairs for its high-performance liquid chromatography-ultraviolet (HPLC-UV) determination. We developed and validated a rapid and economic HPLC-UV method using the superficially porous particle column to determine 13 steviol glycosides (stevioside, dulcoside A, rubusoside, steviobioside, and rebaudioside A-F, I, M, and N).
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