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Rebaudioside E is one of the minor steviol glycoside components first isolated and identified from Stevia rebaudiana in 1977. It is a high-intensity sweetener that tastes about 150-200 times sweeter than sucrose. It is also a precursor for the biosynthesis of rebaudioside D and rebaudioside M, the next-generation Stevia sweeteners. This study reports the enzymatic synthesis of rebaudioside E from stevioside using UDP-glucosyltransferase UGTSL2 from Solanum lycopersicum and sucrose synthase StSUS1 from Solanum tuberosum. [1]
Rebaudioside E does not have a specific pharmacological target in the traditional sense of a drug. As a sweetener, its primary interaction is with sweet taste receptors (TAS1R2/TAS1R3) on the tongue, which are G protein-coupled receptors responsible for sweet taste perception. However, as a steviol glycoside, Rebaudioside E may also interact with glucose transporters and other metabolic pathways. The compound is primarily used as a sweetener and as a precursor for the biosynthesis of other steviol glycosides. Its sweetening properties make it valuable for food and beverage applications as a natural, zero-calorie sweetener. |
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| ln Vitro |
Rebaudioside E was enzymatically synthesized from stevioside using UGTSL2 and StSUS1. In a 20-ml bioconversion reaction containing 20 g/l stevioside, 27.06 mU/ml UGTSL2, and 866.34 mU/ml StSUS1, the production of rebaudioside E reached 15.92 g/l after 24 hours at 30°C with shaking at 200 rpm. The conversion of stevioside was up to 90%. The product was identified by LC-MS/MS, with the characteristic parent ion at 966.4 m/z and fragment ions at 641.3 m/z and 806.0 m/z, matching the rebaudioside E standard. [1]
The purified UGTSL2 (0.25 mg) was used to confirm the conversion of stevioside (2 mM) with UDP-glucose (3 mM) as sugar donor, producing rebaudioside E. [1] In vitro studies on Rebaudioside E are limited, as the compound is primarily used as a sweetener rather than a therapeutic agent. The compound's sweetness potency (150-200 times sweeter than sucrose) has been characterized using taste panel evaluations and cell-based sweet receptor assays. Rebaudioside E has been detected and quantified in Stevia rebaudiana leaves. The compound can be used as a precursor for the biosynthesis of rebaudioside D and rebaudioside M through enzymatic conversion. Detailed in vitro activity data beyond its sweetening properties are not widely available. |
| ln Vivo |
In animal models, rebaudioside E is generally well-tolerated at recommended doses, with no significant adverse effects on glucose homeostasis, blood pressure, or inflammation. At higher doses, it may cause gastrointestinal discomfort and alterations in gut microbiota composition.
In vivo studies on Rebaudioside E are limited. As a sweetener, the compound is consumed orally and is expected to be metabolized by gut bacteria to steviol, which is then absorbed and excreted. Steviol glycosides, including Rebaudioside E, are generally recognized as safe and are used as food additives in many countries. The compound's metabolic fate and safety have been evaluated as part of the regulatory approval process for steviol glycosides. However, specific in vivo studies on Rebaudioside E are not widely available in the published literature. |
| Enzyme Assay |
Rebaudioside E UGTSL2 glucosyltransferase activity assay: The reaction mixture (3 ml) contained 1.2 mM stevioside, 2 mM UDP-glucose, 3 mM MgCl₂ in 50 mM sodium phosphate buffer (pH 7.2), and 1 mg of total protein from crude extract (or 0.25 mg purified UGTSL2). Incubation was at 30°C for 30 min. After heating at 95°C for 10 min and centrifugation, samples were analyzed by HPLC. One unit (U) of glucosyltransferase activity was defined as the amount of enzyme that produced 1 μmol of rebaudioside D from rebaudioside A per minute. [1]
Sucrose synthase StSUS1 activity assay: The reaction mixture (3 ml) contained 500 mM sucrose and 10 mM UDP in 50 mM potassium phosphate buffer (pH 7.2) with 6 mg total protein from crude extract. Incubation was at 30°C, and samples were taken every hour. After heating at 95°C for 10 min and centrifugation, fructose concentrations were measured using the DNS method. One unit (U) of sucrose synthase activity was defined as the amount of enzyme releasing 1 μmol of fructose per minute. [1] The in vitro receptor binding assays for Rebaudioside E are not typically performed, as the compound is a sweetener rather than a drug targeting specific receptors or enzymes. However, the compound's interaction with sweet taste receptors can be studied using cell-based assays expressing the human sweet taste receptor (TAS1R2/TAS1R3). In these assays, cells are treated with Rebaudioside E, and receptor activation is measured using calcium imaging or reporter gene assays. The compound's sweetness potency is determined by comparing its activity to that of sucrose. |
| Cell Assay |
Cell-based assays for Rebaudioside E are typically conducted using sweet taste receptor-expressing cell lines. Cells are cultured in appropriate media and treated with varying concentrations of Rebaudioside E. Receptor activation is measured using calcium-sensitive fluorescent dyes or reporter gene assays that detect downstream signaling. The compound's EC50 for sweet receptor activation is determined from dose-response curves. These cell-based assays are used to characterize the sweetening properties of steviol glycosides and to compare their relative potencies.
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| Animal Protocol |
In animal model studies, rebaudioside E has been evaluated at various dosages. At recommended doses, the compound was generally well-tolerated without significant adverse effects. At higher doses, some studies observed gastrointestinal discomfort and alterations in gut microbiota composition. The compound is absorbed in the small intestine and transported to the liver, where it undergoes further metabolism, with primary localization in the liver and kidneys.
In vivo animal studies for Rebaudioside E are not typically performed for sweetener characterization. However, as part of the safety evaluation of steviol glycosides, animal studies have been conducted to assess the metabolism, toxicity, and safety of these compounds. Rats and mice are administered steviol glycosides orally, and their metabolic fate is studied by analyzing blood, urine, and feces. Chronic toxicity studies are conducted to assess the safety of long-term consumption. These studies have confirmed the safety of steviol glycosides for use as food additives. |
| ADME/Pharmacokinetics |
Rebaudioside E is not absorbed intact. Following oral ingestion, it passes to the lower gastrointestinal tract where it undergoes extensive hydrolysis by gut microflora. In vitro studies using human fecal homogenates under anaerobic conditions demonstrate that rebaudioside E (0.2 mg/mL) is completely metabolized to the common aglycone steviol within 24 hours, with the majority of metabolism occurring within the first 16 hours. There were no apparent gender or ethnicity differences in the rate of metabolism. Steviolbioside, an intermediate in the hydrolysis pathway, is also rapidly degraded to steviol. The compound is absorbed in the small intestine, transported to the liver for further metabolism, and primarily localized in the liver and kidneys for excretion.
Pharmacokinetic data for Rebaudioside E are limited. As a steviol glycoside, the compound is expected to be metabolized by gut bacteria to steviol, which is then absorbed and conjugated in the liver before excretion in urine. The compound has a molecular weight of 967.01 and a molecular formula of C44H70O23. Steviol glycosides are generally not absorbed intact and are metabolized by the gut microbiome. The compound appears as a white to off-white powder. Detailed pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution are not widely reported. |
| Toxicity/Toxicokinetics |
Rebaudioside E is considered safe for consumption at moderate levels. In vitro genotoxicity studies indicate no mutagenic potential, with an Ames test prediction of negative (89.00% probability). Carcinogenicity predictions are also negative (99.00% probability). Hepatotoxicity is predicted to be low (91.25% negative). At higher doses, excessive intake may lead to gastrointestinal discomfort and alterations in gut microbiota composition. Importantly, because rebaudioside E is metabolized to steviol in the same manner as rebaudioside A, the existing toxicology data available on steviol and on steviol glycosides metabolized to steviol (i.e., rebaudioside A) can be used to support the safety of rebaudioside E.
Toxicological data for Rebaudioside E are consistent with the safety profile of steviol glycosides as a class. Steviol glycosides are generally recognized as safe (GRAS) and are approved for use as food additives in many countries. Extensive toxicological studies have been conducted on steviol glycosides, demonstrating no significant toxicity at levels relevant for human consumption. The compound is not intended for therapeutic use and is used primarily as a food ingredient and research tool. |
| References | |
| Additional Infomation |
Rebaudioside E has the chemical structure where R1 is glcβ1-2glcβ1- and R2 is glcβ1-2glcβ1- (both at C-19 carboxyl and C-13 hydroxyl positions). Its molecular formula is C₄₄H₇₀O₂₃. It was first isolated from Stevia rebaudiana Bertoni in 1977. Rebaudioside E tastes about 150-200 times sweeter than sucrose and is also a precursor for biosynthesis of rebaudioside D and rebaudioside M. [1]
This study demonstrated that rebaudioside E can be converted from stevioside catalyzed by UGTSL2. The stereoselectivity and regioselectivity of UGTSL2 showed that the order of glucosylation of the Glc(β1→C-19) carboxyl group of steviol glycosides by UGTSL2 was: (β1→2) linkage > (β1→6) linkage >> (β1→3) linkage. No rebaudioside A (stevioside-G1 with Glcβ1-3Glcβ1→C-13 hydroxyl) was produced, indicating strict regioselectivity on the C-19 carboxyl position. [1] Rebaudioside E is a rebaudioside derivative of steviol glycoside, in which the hydroxyl group at the 2-position of the glucose ester moiety is converted to the corresponding β-D-glucoside. It is both a rebaudioside and a sophoroside. Its function is related to that of steviol glycoside. Rebaudioside E has been reported in stevia (Stevia rebaudiana), and relevant data are available. See also: Stevia rebaudiana leaf (part). Rebaudioside E is a naturally occurring steviol glycoside isolated from Stevia rebaudiana leaves. It is a high-intensity sweetener that tastes approximately 150-200 times sweeter than sucrose. The compound has a molecular formula of C44H70O23 and a molecular weight of 967.01. Rebaudioside E is also a precursor for the biosynthesis of rebaudioside D and rebaudioside M, the next-generation Stevia sweeteners. The compound is used in biochemical experiments, drug synthesis research, and as a reference standard for sweetener formulation. It is not approved for therapeutic use and is available for research and food applications. |
| Molecular Formula |
C44H70O23
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|---|---|
| Molecular Weight |
967.012816905975
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| Exact Mass |
966.431
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| CAS # |
63279-14-1
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| PubChem CID |
72710721
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| Appearance |
White to off-white solid powder
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| Density |
1.59±0.1 g/cm3
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| LogP |
-2.8
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| Hydrogen Bond Donor Count |
14
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| Hydrogen Bond Acceptor Count |
23
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
67
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| Complexity |
1760
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| Defined Atom Stereocenter Count |
26
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| SMILES |
O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@]12C(=C)C[C@]3(CC[C@@H]4[C@@](C(=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)(C)CCC[C@@]4(C)[C@@H]3CC1)C2
|
| InChi Key |
RLLCWNUIHGPAJY-SFUUMPFESA-N
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| InChi Code |
InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-34(30(55)26(51)20(14-47)62-38)64-36-32(57)28(53)24(49)18(12-45)60-36)23(43)6-10-44(17,16-43)67-39-35(31(56)27(52)21(15-48)63-39)65-37-33(58)29(54)25(50)19(13-46)61-37/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
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| Chemical Name |
[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
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| Synonyms |
Rebaudioside E; (-)-Rebaudioside E; 693TGS3OHR; FEMA NO. 4936;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0341 mL | 5.1706 mL | 10.3412 mL | |
| 5 mM | 0.2068 mL | 1.0341 mL | 2.0682 mL | |
| 10 mM | 0.1034 mL | 0.5171 mL | 1.0341 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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