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
SMILES
[H][C@@]12CC[C@@]3(C[C@]1(CC3=C)CC[C@]4([H])[C@@](C)(CCC[C@@]24C)C(O)=O)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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111188 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22096997 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22096997
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.
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SUBSTANCE RECORD