Bioconversion of Rebaudioside I from Rebaudioside A

Prakash, Indra; Bunders, Cynthia; Devkota, Krishna Prasad; Charan, Romila D.; Ramı́rez, Catherine; Snyder, Tara M.; Priedemann, Christopher; Markosyan, A. A.; Jarrin, Cyrille; Halle, Robert Ter

doi:10.3390/molecules191117345

Cited by 24 publications

(16 citation statements)

References 24 publications

(24 reference statements)

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“…[Glc(b1 / 6)Glc1], was obtained as a minor product in the bioconversion reaction of RebA into rebaudioside D [Glc(b1 / 2) Glc1] using UDP-Glc as glucosyl donor and the b-glucosyltransferase UGTSL2 enzyme as biocatalyst [41]. Furthermore, a Glc(a1 / 6) extension of Glc1 of stevioside was demonstrated in a transglucosylation reaction with maltose as donor substrate in the presence of Biozyme L [20].…”

Section: Structural Analysis Of Hplc Fraction F2mentioning

confidence: 99%

Structural analysis of rebaudioside A derivatives obtained by Lactobacillus reuteri 180 glucansucrase-catalyzed trans-α-glucosylation

Gerwig

Poele

Dijkhuizen

et al. 2017

Carbohydrate Research

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Structural analysis of rebaudioside A derivatives obtained by Lactobacillus reuteri 180 glucansucrase-catalyzed trans-α-glucosylation Gerwig, Gerrit; te Poele, Evelien; Dijkhuizen, Lubbert; Kamerling, Johannis P a b s t r a c tThe wild-type Gtf180-DN glucansucrase enzyme from Lactobacillus reuteri 180 was found to catalyze the a-glucosylation of the steviol glycoside rebaudioside A, using sucrose as glucosyl donor in a transglucosylation process. Structural analysis of the formed products by MALDI-TOF mass spectrometry, methylation analysis and NMR spectroscopy showed that rebaudioside A is specifically a-D-glucosylated at the steviol C-19 b-D-glucosyl moiety (55% conversion). The main product is a mono-(a1 / 6)-glucosylated derivative (RebA-G1). A series of minor products, up to the incorporation of eight glucose residues, comprise elongations of RebA-G1 with mainly alternating (a1 / 3)-and (a1 / 6)-linked glucopyranose residues. These studies were carried out in the context of a program directed to the improvement of the taste of steviol glycosides via enzymatic modification of their naturally occurring carbohydrate moieties. IntroductionThe leaves of the Stevia rebaudiana BERTONI plant contain a high variety of sweet substances, called steviol glycosides [1,2], and so far more than 40 different structures have been elucidated (see review Ref. [3]). Stevioside (~5e20% w/w of dried leaves) and rebaudioside A (~2e5% w/w of dried leaves) are the most abundant components (Fig. 1), tasting about 200e300 times sweeter than sucrose (0.4% aqueous solution). Structurally, steviol glycosides have ent-13-hydroxykaur-16-en-19-oic acid as aglycone, called steviol, but are differing in carbohydrate composition at the C-13-tert-hydroxyl and C-19-carboxyl functions.Due to the growing awareness and concerns for human health related to excessive consumption of sugar (sucrose), the application of steviol glycosides as non-caloric bio-alternatives for sucrose and as substitutes for artificial (synthetic) sweeteners is strongly promoted nowadays [4e8]. Since a couple of years, steviol glycosides have been permitted for use as food additive and sweetener in the USA [9] and in Europe (E960) [10,11]. However, despite their intense sweetness and diverse beneficial pharmacological properties [12e15], the main drawback for successful commercialization of Stevia sweeteners is their slight bitterness and unpleasant (metallic) aftertaste, experienced by more than half of the human population.For natural steviol glycosides with b-D-glucopyranosyl units as constituents, it has been reported that the ratio of the number of glucose units at the C-13 site to that at the C-19 site of the steviol core has a relationship with the sweetness as well as with the quality of taste of the steviol glycosides [16,17]. To improve the Abbreviations: FID, free induction decay; FWHM, full width at half maximum; GLC-EI-MS, gas-liquid chromatography electron impact mass spectrometry; HPAEC, high-pH anion-exchange chromatography; HSQC, 1 H-detected hetero-nucl...

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Section: Structural Analysis Of Hplc Fraction F2mentioning

confidence: 99%

Structural analysis of rebaudioside A derivatives obtained by Lactobacillus reuteri 180 glucansucrase-catalyzed trans-α-glucosylation

Gerwig

Poele

Dijkhuizen

et al. 2017

Carbohydrate Research

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show abstract

“…The taste of steviol glycosides strongly depends on the nature and degree of glycosylation [27]. Several approaches have therefore been developed to modify the glycosylation of steviol glycosides [28][29][30][31][32][33][34][35][36][37][38][39][40]. A combination of two different FTases can be used not only to improve the taste of steviol glycosides, but also to functionalize them.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic production of prebiotic fructo‐oligosteviol glycosides

Spohner

Czermak

2016

Journal of Molecular Catalysis B: Enzymatic

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“…16 Several ultra-high-performance liquid chromatography (UHPLC) methods have also been developed for the rapid analysis of the major steviol glycosides. 17,18 The taste and physical characteristics of steviol glycosides can be further improved via innovative processing such as biosynthesis and bioconversion, of which technologies have led to an increasing market availability of high-purity non-naturally abundant minor steviol glycosides such as rebaudioside E, I, M, and N. 3,4,19,20 Because major steviol glycosides are often the substrates or impurities of the novel steviol glycoside productions, an analytical method to separate and quantify both major and minor steviol glycosides is needed for the product quality control and processing development troubleshooting. The most updated standardized method for steviol glycosides analysis is JECFA 2017, 13 which runs a gradient elution for 80 min for the accurate quantification of 13 glycosides in HPLC-UV with optional mass spectrometry (MS) determination for the estimation of 34 steviol glycosides.…”

Section: Introductionmentioning

confidence: 99%

Rapid and Economic Determination of 13 Steviol Glycosides in Market-Available Food, Dietary Supplements, and Ingredients: Single-Laboratory Validation of an HPLC Method

Liu

Kawaguchi

Feng

et al. 2020

J. Agric. Food Chem.

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Steviol glycosides, obtained from leaves of Stevia rebaudiana 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). Baseline separation with a minimum resolution of 1.5 for 13 steviol glycosides was achieved within only 14 min of separation time. The hydrocarbon stationary phase with additional steric interactions from the isobutyl side chains on the C18 ligand was shown to be an important contributor to chromatographic selectivity of several critical pairs of steviol glycosides. The method was proven to perform suitably on columns from three different manufacturers and two HPLC instruments. The method was further used to perform a single-lab validation on eight food and supplement products with multiple matrices. The results ranged from 0.05% w/w rebaudioside A for a hard-candy finished product to 100.8% w/w purity for a rebaudioside M raw ingredient. The validation test results showed that the method was linear, suitable, specific, accurate, and precise. The method is therefore suitable to be considered as a new industrial standard for quality control analysis for stevia products.

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Bioconversion of Rebaudioside I from Rebaudioside A

Cited by 24 publications

References 24 publications

Structural analysis of rebaudioside A derivatives obtained by Lactobacillus reuteri 180 glucansucrase-catalyzed trans-α-glucosylation

Structural analysis of rebaudioside A derivatives obtained by Lactobacillus reuteri 180 glucansucrase-catalyzed trans-α-glucosylation

Enzymatic production of prebiotic fructo‐oligosteviol glycosides

Rapid and Economic Determination of 13 Steviol Glycosides in Market-Available Food, Dietary Supplements, and Ingredients: Single-Laboratory Validation of an HPLC Method

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