Rebaudioside M
(Synonyms: 瑞鲍迪苷M) 目录号 : GC37080A natural non-caloric sweetener and TAS1R2/TAS1R3 agonist
Cas No.:1220616-44-3
Sample solution is provided at 25 µL, 10mM.
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Rebaudioside M is a natural non-caloric sweetener and an agonist of the class 1 sweet taste receptor (TAS1R) heterodimer formed by TAS1R2 and TAS1R3.1 It is one of the minor steviol glycosides isolated from S. rebaudiana leaves.2 Rebaudioside M increases intracellular calcium levels in HEK293 cells expressing human TAS1R2 and TAS1R3 (EC50 = 29.54 ?M) and has a relative sweetness potency 200-350 times that of sucrose.1,2 Rebaudioside M is metabolized by gut microbiota to steviol, a compound whose safety is widely studied.2,3,4
1.Choi, Y., Manthey, J.A., Park, T.H., et al.Correlation between in vitro binding activity of sweeteners to cloned human sweet taste receptor and sensory evaluationFood Sci. Biotechnol.30(5)675-682(2021) 2.Prakash, I., Markosyan, A., and Bunders, C.Development of next generation Stevia sweetener: Rebaudioside MFoods3(1)162-175(2014) 3.Purkayastha, S., Markosyan, A., Prakash, I., et al.Steviol glycosides in purified stevia leaf extract sharing the same metabolic fateRegul. Toxicol. Pharmacol.77125-133(2016) 4.Roberts, A., and Renwick, A.G.Comparative toxicokinetics and metabolism of rebaudioside A, stevioside, and steviol in ratsFood Chem. Toxicol.46(Suppl 7)S31-S39(2008)
Cas No. | 1220616-44-3 | SDF | |
别名 | 瑞鲍迪苷M | ||
分子式 | C56H90O33 | 分子量 | 1291.29 |
溶解度 | DMSO : 100 mg/mL (77.44 mM; Need ultrasonic) | 储存条件 | Store at -20°C,protect from light |
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1 mg | 5 mg | 10 mg | |
1 mM | 0.7744 mL | 3.8721 mL | 7.7442 mL |
5 mM | 0.1549 mL | 0.7744 mL | 1.5488 mL |
10 mM | 0.0774 mL | 0.3872 mL | 0.7744 mL |
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给药剂量 | mg/kg | 动物平均体重 | g | 每只动物给药体积 | ul | 动物数量 | 只 | |||
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% DMSO % % Tween 80 % saline | ||||||||||
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DMSO母液配制方法: mg 药物溶于 μL DMSO溶液(母液浓度 mg/mL,
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1. 首先保证母液是澄清的;
2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
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Enhancement of Rebaudioside M Production by Structure-Guided Engineering of Glycosyltransferase UGT76G1
J Agric Food Chem 2022 Apr 27;70(16):5088-5094.PMID:35417157DOI:10.1021/acs.jafc.2c01209.
Owing to zero-calorie and advanced organoleptic properties similar to sucrose, the plant-derived Rebaudioside M (Reb M) has been considered as a next generation sweetener. However, a low content of Reb M in Stevia rebaudiana Bertoni and low enzymatic activity of UGT76G1, which is an uridine diphosphate glucose (UDPG)-dependent glycosyltransferase with the ability to glycosylate rebaudioside D (Reb D) to produce Reb M through the formation of β-1,3 glycosidic bond, restrict its commercial usage. To improve the catalytic activity of UGT76G1, a variant UGT76G1-T284S/M88L/L200A was obtained by structure-guided evolution, whose catalytic activity toward Reb D increased by 2.38 times compared with UGT76G1-T284S. This allowed us to prepare Reb M on a large-scale with a great yield of 90.50%. Moreover, molecular dynamics simulation illustrated that UGT76G1-T284S/M88L/L200A reduced distances from Reb D to catalytic residues and UDPG. Hence, we report an efficient method for the potential scale production of Reb M in this study.
Development of Next Generation Stevia Sweetener: Rebaudioside M
Foods 2014 Feb 27;3(1):162-175.PMID:28234311DOI:10.3390/foods3010162.
This work aims to review and showcase the unique properties of Rebaudioside M as a natural non-caloric potential sweetener in food and beverage products. To determine the potential of Rebaudioside M, isolated from Stevia rebaudiana Bertoni, as a high potency sweetener, we examined it with the Beidler Model. This model estimated that Rebaudioside M is 200-350 times more potent than sucrose. Numerous sensory evaluations of Rebaudioside M's taste attributes illustrated that this steviol glycoside possesses a clean, sweet taste with a slightly bitter or licorice aftertaste. The major reaction pathways in aqueous solutions (pH 2-8) for Rebaudioside M are similar to rebaudioside A. Herein we demonstrate that Rebaudioside M could be of great interest to the global food industry because it is well-suited for blending and is functional in a wide variety of food and beverage products.
Co-immobilized recombinant glycosyltransferases efficiently convert rebaudioside A to M in cascade
RSC Adv 2021 Apr 28;11(26):15785-15794.PMID:35481200DOI:10.1039/d0ra10574k.
Rebaudioside M (Reb M), as a natural and healthy Stevia sweetener, is produced by two glycosyltransferases that catalyze the serial glycosylation of Rebaudioside A (Reb A) and Rebaudioside D (Reb D) in cascade. Meanwhile, it is of great importance in developing an immobilization strategy to improve the reusability of glycosyltransferases in reducing the production cost of Reb M. Here, the recombinant glycosyltransferases, i.e., OsEUGT11 (UGT1) and SrUGT76G1 (UGT2), were expressed in Escherichia coli and covalently immobilized onto chitosan beads. UGT1 and UGT2 were individually immobilized and co-immobilized onto the beads that catalyze Reb A to Reb M in one-pot. The co-immobilized enzymes system exhibited ∼3.2-fold higher activity than that of the mixed immobilized enzymes system. A fairly high Reb A conversion rate (97.3%) and a high Reb M yield of 72.2% (4.82 ± 0.11 g L-1) were obtained with a feeding Reb A concentration of 5 g L-1. Eventually, after 4 and 8 reused cycles, the co-immobilized enzymes retained 72.5% and 53.1% of their original activity, respectively, showing a high stability to minimize the total cost of enzymes and suggesting that the co-immobilized UGTs is of potentially signficant value for the production of Reb M.
Comparative transcriptomic of Stevia rebaudiana provides insight into rebaudioside D and Rebaudioside M biosynthesis
Plant Physiol Biochem 2021 Oct;167:541-549.PMID:34425398DOI:10.1016/j.plaphy.2021.08.028.
Rebaudioside D (Reb D) and Rebaudioside M (Reb M) are commercially important low/no-calorie natural sweeteners. However, they are present in a minor proportion of all steviol glycosides (SGs) in Stevia rebaudiana Bertoni (S. rebaudiana). Strain-dependent deviation in Reb D and Reb M biosynthesis is one key breach for breeding of S. rebaudiana, which has not been studied at the transcriptional level. Herein, five different S. rebaudiana varieties with distinct SGs contents, one cultivar having high stevioside content (HST), one cultivar having high Reb A content (HRA) and three cultivars having high Reb D and Reb M content (HDM1, HDM2, HDM3), were selected for RNA-seq analysis. In total, 131,655 de novo assembled unigenes were found in the RNA-seq data. According to Reb D and Reb M content divergence of S. rebaudiana accessions, 2186 differentially expressed genes (DEGs) were selected as potential genes related to Reb D and Reb M biosynthesis. Weighted Gene Co-expression Network Analysis (WGCNA) was used to explore the genes associated with the Reb D and Reb M biosynthesis. The unigenes from the positively associated turquoise module formed a layered co-expression network. There are 7 UDP-dependent glycosyltransferases (UGT) and 76 transcription factors (TFs) distributing at different regions which represented varying coherence of Reb D and Reb M biosynthesis. Particularly, two TFs having a strong correlation with two UGTs in the network were also discovered. The present study provided a comprehensive insight into networks for regulation of Reb D and Reb M contents in S. rebaudiana.
In vitro metabolism of rebaudioside B, D, and M under anaerobic conditions: comparison with rebaudioside A
Regul Toxicol Pharmacol 2014 Mar;68(2):259-68.PMID:24361573DOI:10.1016/j.yrtph.2013.12.004.
The hydrolysis of the steviol glycosides rebaudioside A, B, D, and M, as well as of steviolbioside (a metabolic intermediate) to steviol was evaluated in vitro using human fecal homogenates from healthy donors under anaerobic conditions. Incubation of each of the rebaudiosides resulted in rapid hydrolysis to steviol. Metabolism was complete within 24h, with the majority occurring within the first 8h. There were no clear differences in the rate or extent of metabolism of rebaudioside B, D, or M, relative to the comparative control rebaudioside A. The hydrolysis of samples containing 2.0mg/mL of each rebaudioside tended to take slightly longer than solutions containing 0.2mg/mL. There was no apparent gender differences in the amount of metabolism of any of the rebaudiosides, regardless of the concentrations tested. An intermediate in the hydrolysis of Rebaudioside M to steviol, steviolbioside, was also found to be rapidly degraded to steviol. The results demonstrate that rebaudiosides B, D, and M are metabolized to steviol in the same manner as rebaudioside A. These data support the use of toxicology data available on steviol, and on steviol glycosides metabolized to steviol (i.e., rebaudioside A) to substantiate the safety of rebaudiosides B, D, and M.