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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H50O13
Molecular Weight 642.7329
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STEVIOLBIOSIDE

SMILES

C=C1C[C@]23CC[C@@]4([H])[C@@](C)(CCC[C@@]4(C)C(=O)O)[C@]3([H])CC[C@@]1(C2)O[C@@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O5)O)O)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O6)O)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 642.7329
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats.
2016 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Sat Jun 26 06:33:53 UTC 2021
Edited
by admin
on Sat Jun 26 06:33:53 UTC 2021
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
FDA UNII
07GV37SOFN
Created by admin on Sat Jun 26 06:33:53 UTC 2021 , Edited by admin on Sat Jun 26 06:33:53 UTC 2021
PRIMARY
USP_CATALOG
1622350
Created by admin on Sat Jun 26 06:33:53 UTC 2021 , Edited by admin on Sat Jun 26 06:33:53 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB12434
Created by admin on Sat Jun 26 06:33:53 UTC 2021 , Edited by admin on Sat Jun 26 06:33:53 UTC 2021
PRIMARY
CAS
41093-60-1
Created by admin on Sat Jun 26 06:33:53 UTC 2021 , Edited by admin on Sat Jun 26 06:33:53 UTC 2021
PRIMARY
PUBCHEM
16401639
Created by admin on Sat Jun 26 06:33:53 UTC 2021 , Edited by admin on Sat Jun 26 06:33:53 UTC 2021
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.