471-80-7

Usage

Uses

Used in Food and Beverage Industry:
Stevioside is used as a non-nutritive sweetening agent for its intense sweetness and zero-calorie content, making it an ideal alternative to traditional sugar and artificial sweeteners. It is particularly useful for individuals with diabetes or those looking to reduce their sugar intake.
Used in Pharmaceutical Industry:
Stevioside is used as a sweetening agent in the development of pharmaceutical products, such as tablets, capsules, and syrups, where a sugar-free or low-calorie option is desired. Its natural origin and minimal impact on blood sugar levels make it a preferred choice for patients with diabetes or those on a calorie-restricted diet.

Health Hazard

Steviol has been reported to be mutagenic.Wide use of stevia in Japan for >30 years did not produce any known deleterious side effects. In Japan, enzymatically glycosylated blend of stevioside and rebaudioside A, which appears to impart a cleaner taste profile, is also available commercially.

Biochem/physiol Actions

Steviol is an inhibitor of hOAT1 and hOAT3 organic anion transporters. Human organic anion transporter hOAT1 belongs to a superfamily of organic anion transporters, which play critical roles in the body disposition of clinically important drugs including anti-HIV therapeutics, anti-tumor drugs, antibiotics, anti-hypertensives, and anti-inflammatories. Steviol is a useful tool for studying renal drug clearance.

InChI:InChI=1/C20H30O3/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19/h14-15,23H,1,4-12H2,2-3H3,(H,21,22)/t14?,15?,17-,18-,19-,20+/m1/s1

Upstream product

• 57817-89-7 stevioside 
• 1326217-31-5 C₄₃H₆₈O₂₂ 
• 57817-89-7 stevioside 
• 58543-16-1 rebaudioside A 

Downstream Products

• 64977-89-5 steviol 19β-glucopyranosyl ester 
• 140447-36-5 steviol 19-β-gentiobiosyl ester 
• 64849-39-4 steviol 13-O-β-glucopyranoside 19-β-glucopyranosyl ester 
• 19018-46-3 7β,13-dihydroxykaurenolide 
• 51576-10-4 ent-13-acetoxykaur-16-en-19-oic acid 
• 27975-19-5 isosteviol 
• 30799-71-4 (4ar)-4bt,8c,12c-Trimethyl-8t-methoxycarbonyl-(2tH,4arH,8acH)-1,2,4,4a,4b,5,6,7,8,8a,9,10-dodekahydro-3H-2c,10ac-ethano-phenanthren 
• 1173883-94-7 benzyl ent-13-hydroxykaur-16-en-19-oate 
• 1185737-16-9 13-hydroxy-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester 
• 60129-60-4 13-O-β-glucopyranosol steviol 

Relevant academic research and scientific papers

Reaction coupling separation for isosteviol production from stevioside catalyzed by acidic ion-exchange resin

Abstract: Isosteviol, a prodrug used to be obtained via Wagner–Meerwein rearrangement from steviol with low yield and long reaction?time. Herein, an in-situ separation-coupling-reaction is presented to prepare isosteviol from the natural sweetener stevioside. Simply with in-situ water-washing, the product containing 92.98% purity of isosteviol was obtained with a stevioside conversion of 97.23% from a packet bed reactor without further separation. Within the assayed inorganic acid, organic acids and acidic ionic liquids, the acidic ion-exchange resins provided higher product specificity towards isosteviol. Furthermore, comparing to 5-Fluorouracil, the product presented similar and even stronger inhibition on proliferation of the assayed human cancer cells in a time and dose-dependence by causing cell phase arrest. Isosteviol treatment caused G1 arrest on SGC-7901, HCT-8 and HCT-116 cells, S arrest on HepG2, Huh-7 and HepG3B cells, and G2 arrest on MGC-803 cells, respectively. Graphic abstract: Reaction coupling separation for isosteviol production catalyzed by acidic ion-exchange resin.[Figure not available: see fulltext.]

Endocyclic double bond isomers and by-products from rebaudioside A and stevioside formed under acid conditions

The hydrolysis reaction of rebaudioside A and stevioside was studied under mild and strong acidic conditions at different temperatures and times. Exposure of rebaudioside A to vigorous acid conditions yielded three different aglycone cores which were puri

A complete specific cleavage of glucosyl and ester linkages of stevioside for preparing steviol with a β-galactosidase from Sulfolobus solfataricus

β-Galactosidases from Sulfolobus solfataricus have been used to synthesize galactooligosaccharide and lactulose. In this work, a β-galactosidase from S. solfataricus with weak β-glucosidase activity but high lipase activity was employed as catalyst to assist hydrolysis of stevioside to obtain steviol, an important starting reagent of synthetic bioactive materials and the main metablite of stevioside in human digistion. The β-galactosidase presented a strict substrate specifity on converting stevioside to steviol in a stoichiometric yield. The β-galactosidase favors the cleavage of glycoside linkages prior to cleavage of glycosyl ester linkage. The hydrolysis is external diffusion controlled and hence has to bear low substrate concentration in regular process, but this can be solved with product removal or enzyme immobilization. The immobilization of the β-galactosidase onto cross-linked chitosan microspheres did not enhance the enzyme's thermal or pH stability but eliminated the external diffusion, and therefore speeded the hydrolysis in 3 folds. The relative reaction activity dropped only 1.75% after 6 runs of using the immobilized β-galactosidase.

Enzymatic preparation of a natural sweetener rubusoside from specific hydrolysis of stevioside with β-galactosidase from Aspergillus sp.

Rubusoside is a precious bioactive sweetener which mainly exists in Chinese sweet tea plant (Rubus suavissimus S. Lee), while stevioside is an abundant natural sweetener with bitter aftertaste. In this work, a β-galactosidase from Aspergillus sp. presented specific hydrolytic activity on β-1,2 glucosidic linkage of stevioside, and converting stevioside to rubusoside. The hydrolytic activity was weak on the natural stevioside analogs, which makes the process a promising approach to produce rubusoside and utilize stevioside. The highest steviosides conversion was 98.3%, accompanying with a rubusoside yield of 91.4%.

Minor diterpenoid glycosides from the leaves of Stevia rebaudiana

From the commercial extract of the leaves of Stevia rebaudiana, three new diterpenoid glycosides were isolated besides eight known steviol glycosides including stevioside, rebaudiosides A-F and dulcoside A. The structures of the three compounds were identified as 13-[(2-O-β-d-glucopyranosyl-β-d- glucopyranosyl) oxy]-kaur-16-en-18-oic acid-(6-O-β-d-xylopyranosyl-β- d-glucopyranosyl) ester (1), 13-[(2-O-β-d-glucopyranosyl-β-d- glucopyranosyl) oxy]-17-hydroxy-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (2), and 13-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]-17-oxo-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (3) on the basis of extensive NMR and MS spectral studies. Another known diterpenoid glycoside, 13-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl) oxy]-kaur-15-en-18-oic acid β-d-glucopyranosyl ester (4) was also isolated and its complete NMR spectral assignments were made on the basis of COSY, HSQC and HMBC spectral data.

ENZYMATIC DETERMINATION OF STEVIOSIDE IN STEVIA REBAUDIANA

A simple enzymatic method is described for the determination of stevioside in Stevia rebaudiana.The method is based on the hydrolysis of stevioside with crude hesperidinase.The reaction is followed by monitoring the production of glucose with a glucose oxidase-peroxidase-2,2'-azino-di-(3-ethylbenzothiazoline-6-sulfonic acid) system.The results for the stevioside content in S. rebaudiana leaves correlate with those obtained by other methods.The stevioside content in S. rebaudiana plants showed large variation.Key Word Index - Stevia rebaudiana; Compositae; enzymatic assay; diterpene glucoside; stevioside; natural sweetener.