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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H50O13
Molecular Weight 642.7316
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STEVIOLBIOSIDE

SMILES

C[C@@]12CCC[C@](C)([C@H]1CC[C@@]34CC(=C)[C@@](C3)(CC[C@@H]24)O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(O)=O

InChI

InChIKey=OMHUCGDTACNQEX-OSHKXICASA-N
InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(40)41)19(31)6-10-32(15,14-31)45-27-25(23(38)21(36)17(13-34)43-27)44-26-24(39)22(37)20(35)16(12-33)42-26/h16-27,33-39H,1,4-14H2,2-3H3,(H,40,41)/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1

HIDE SMILES / InChI

Molecular Formula C32H50O13
Molecular Weight 642.7316
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Steviolbioside, 13-[(2-O-b-D-glucopyranosyl-b-D-glucopyrano syl)oxy]kaur-16-en-18-oic acid, is a bioactive nature sweetener, which is rare in Stevia rebaudiana leaves. It is also the main metabolite of the star sweetener rebaudioside A and its analogue stevioside, yet it can be used as an intermediate of some medications, which makes steviolbioside an important reagent in medical science in addition to a food additive. Steviolbioside has antituberculosis activity. Steviolbioside has been used in trials studying the treatment of HIV-1 Infection. Except for its antihyperglycaemic and antihypertensive effects, steviolbioside was found as a moderate antituberculosis activity against Mycobacterium tuberculosis strain H37RV in vitro (MIC = 3.75 ug/ml), compared to that of stevioside (MIC = 7.5 ug/ml). The hydrolysis product steviolbioside presented higher cytoxicity on human normal cells (hepatocytes cell L02 and intestinal epithelial cell T84) than did its starting material stevioside. e. Compared to the typical chemotherapy agent, 5-fluorouracil (5-FU), steviolbioside has a much lower cytotoxic effect on all assayed human normal cells, but it presented notable inhibition on Hep3B, human breast cancer cell MDA-MB-231 and human pancreatic cancer cell BxPC-3. The inhibition rate on MDA-MB-231 of steviolbioside was 50% of that of 5-FU, which implies a hopeful potential remedy for human breast cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Production of a bioactive sweetener steviolbioside via specific hydrolyzing ester linkage of stevioside with a β-galactosidase.
2016 Apr 1
Gene transcription and steviol glycoside accumulation in Stevia rebaudiana under polyethylene glycol-induced drought stress in greenhouse cultivation.
2016 Sep
Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats.
2016 Sep
Physico-chemical and sensory characteristics of steviolbioside synthesized from stevioside and its application in fruit drinks and food.
2017 Jan
Patents

Sample Use Guides

In Vitro Use Guide
The minimum concentration at which the growth of M. tuberculosis was inhibited by 100% (MIC) for stevioside and steviolbioside equals 7.5 and 3.8 ug/mL, respectively.
Substance Class Chemical
Created
by admin
on Tue Oct 22 18:27:56 UTC 2019
Edited
by admin
on Tue Oct 22 18:27:56 UTC 2019
Record UNII
07GV37SOFN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STEVIOLBIOSIDE
USP-RS  
Common Name English
KAUR-16-EN-18-OIC ACID, 13-((2-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-, (4.ALPHA.)-
Systematic Name English
STEVIOBIOSIDE
Common Name English
STB
Common Name English
STEVIOLBIOSIDE [USP-RS]
Common Name English
(-)-STEVIOLBIOSIDE
Common Name English
Code System Code Type Description
CAS
41093-60-1
Created by admin on Tue Oct 22 18:27:56 UTC 2019 , Edited by admin on Tue Oct 22 18:27:56 UTC 2019
PRIMARY
PUBCHEM
16401639
Created by admin on Tue Oct 22 18:27:56 UTC 2019 , Edited by admin on Tue Oct 22 18:27:56 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
MIC value of the in vitro growth of Mycobacterium Tuberculosis (H37RV strain) of the new anti-tuberculosis terpenoid derived agent tested was 3.8 ug/ml. Isolated stevia sweetener, produced by the extraction of STEVIA REBAUDIANA leaves by hot water and powdering.