58543-16-1
Chemical Structure
Rebaudioside A
- CAS No.: 58543-16-1
- Formula:C44H70O23
- Molecular Weight:967.01
IUPAC Name: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (4R,4aS,6aR,9S,11aR,11bS)-9-(((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
InChIKey: HELXLJCILKEWJH-NCGAPWICSA-N
SMILES: C[C@]12[C@@]3([H])[C@@](C4)(CC[C@]1([H])[C@@](C)(CCC2)C(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)CO)=O)C[C@@](C4=C)(O[C@@]6([H])[C@@H]([C@H]([C@H](O)[C@@H](CO)O6)O[C@]7([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)CO)O[C@]8([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]8O)CO)CC3
Biological Activity: Rebaudioside A is an orally effective steviol glycoside with high sweetness. Rebaudioside A acts as an inhibitor of α-glucosidase with an IC50 value of 35.01 μg/mL. Rebaudioside A increases the ATP/ADP ratio in β cells in a glucose-dependent manner, thereby inhibiting KATP channels, leading to membrane depolarization, calcium influx, and ultimately stimulating insulin secretion. Rebaudioside A activates the SREBP signaling pathway by inhibiting HMGCR, the rate-limiting enzyme in cholesterol synthesis, resulting in increased expression of LDLR on the cell surface, thus promoting the uptake of LDL-C in the blood. Rebaudioside A can be used for studies on blood glucose and lipid regulation as well as anti-obesity[1][2][3][4][5].
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Rebaudioside A | 98.0% | Rebaudioside A is an orally effective steviol glycoside with high sweetness. Rebaudioside A acts as an inhibitor of α-glucosidase with an IC50 value of 35.01 μg/mL. Rebaudioside A increases the ATP/ADP ratio in β cells in a glucose-dependent manner, thereby inhibiting KATP channels, leading to membrane depolarization, calcium influx, and ultimately stimulating insulin secretion. Rebaudioside A activates the SREBP signaling pathway by inhibiting HMGCR, the rate-limiting enzyme in cholesterol synthesis, resulting in increased expression of LDLR on the cell surface, thus promoting the uptake of LDL-C in the blood. Rebaudioside A can be used for studies on blood glucose and lipid regulation as well as anti-obesity. | ||||||||||||||||||||
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Rebaudioside A (Standard) | 99.90% | Rebaudioside A (Standard) is the analytical standard of Rebaudioside A. This product is intended for research and analytical applications. Rebaudioside A is an orally effective steviol glycoside with high sweetness. Rebaudioside A acts as an inhibitor of α-glucosidase with an IC50 value of 35.01 μg/mL. Rebaudioside A increases the ATP/ADP ratio in β cells in a glucose-dependent manner, thereby inhibiting KATP channels, leading to membrane depolarization, calcium influx, and ultimately stimulating insulin secretion. Rebaudioside A activates the SREBP signaling pathway by inhibiting HMGCR, the rate-limiting enzyme in cholesterol synthesis, resulting in increased expression of LDLR on the cell surface, thus promoting the uptake of LDL-C in the blood. Rebaudioside A can be used for studies on blood glucose and lipid regulation as well as anti-obesity. | ||||||||||||||||||||
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References
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[1]. Abudula R, et al. Rebaudioside A directly stimulates insulin secretion from pancreatic beta cells: a glucose-dependent action via inhibition of ATP-sensitive K-channels. Diabetes Obes Metab. 2008 Nov;10(11):1074-85.
[Content Brief] - [2]. Wang Y, et al. Natural and low-caloric rebaudioside A as a substitute for dietary sugars: A comprehensive review. Compr Rev Food Sci Food Saf. 2023;22(1):615-642. [Content Brief]
- [3]. Ilias AN, et al. Rebaudioside A Enhances LDL Cholesterol Uptake in HepG2 Cells via Suppression of HMGCR Expression. Rep Biochem Mol Biol. 2021;10(3):477-487. [Content Brief]
- [4]. Kim Y, et al. A combination of rebaudioside A and neohesperidin dihydrochalcone suppressed weight gain by regulating visceral fat and hepatic lipid metabolism in ob/ob mice. Food Sci Biotechnol. 2023;33(4):913-923. Published 2023 Aug 26. [Content Brief]
- [5]. Adari BR et al. Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni. Food Chem. 2016 Jun 1;200:154-8. [Content Brief]
