58543-16-1, Stevioside,
甜叶菊甙,
CAS:58543-16-1
C44H70O23 / 967.01
Rebaudioside A is a steviol glycoside found in Stevia rebaudiana leaf leaves that contains 9.1% stevioside and 3.8% rebaudioside.
The glycoside is monosaccharide-free and only contains glucose. It has four glucose molecules, the central glucose being connected to the primary triplet's steviol structure at the hydroxyl group and the rest at the carboxyl group creating an ester bond.
Rebaudioside A also can be described as a natural, non-caloric sweetener. It is obtained from S. rebaudiana plants.
Biological activity of Rebaudioside A
It increases glucagon-like peptide (GLP-1) secretion in a 2-dimensional mouse intestine model. In a two-bottle preference test, mice drink more water containing rebaudioside A than unsweetened water, though saccharin-sweetened water is still preferred. Rebaudioside A also is metabolized by gut microbiota to steviol, a compound whose safety is widely studied. Consumption of rebaudioside A formulations by pre-diabetic patients did not increase fasting or 2-hour plasma glucose or insulin levels.
Sources of Rebaudioside A
Rebaudioside A can be obtained from Stevia Rebaudiana plant species.
The physiological function of Rebaudioside A
Rebaudioside A stimulates gut protein release and promotes enteroendocrine cell differentiation in small intestine organoids. The long-term treatment of C57BL6/J mice treated with Rebaudioside A did not alter the insulin action or cause weight gain. In rats, chemically induced epilepsy showed a dose-dependent decline in spikes in epileptiform activities in rats treated with rebaudioside.
Uses of Rebaudioside A
Rebaudioside A is a sweetener with a sweetness of 300 times sugar but no effect on blood glucose. Rebaudioside A's use in treating diabetes, high blood pressure, and weight loss is a result.
Rebaudioside A is a natural sweetener found in the stevia plant. It has been shown to have physiological effects, including thermodynamic data and mitochondrial membrane potential. Rebaudioside A has synergistic effects with other natural compounds, such as chlorogenic acids, which may be responsible for its toxicity studies. Rebaudioside A is not toxic to humans at high doses.
CAS Number | 58543-16-1 |
Product Name | Rebaudioside A |
IUPAC Name | [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate |
Molecular Formula | C44H70O23 |
Molecular Weight | 967.01 g/mol |
InChI | InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,41-,42-,43-,44+/m1/s1 |
InChI Key | HELXLJCILKEWJH-NCGAPWICSA-N |
SMILES | CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)(C)C(=O)OC8C(C(C(C(O8)CO)O)O)O |
Solubility | Soluble in DMSO |
Synonyms | 19-O-beta-glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-oic acid, 19-O-beta-glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosylsteviol, rebaudioside A |
Canonical SMILES | CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)(C)C(=O)OC8C(C(C(C(O8)CO)O)O)O |
Isomeric SMILES | C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O |
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