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
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
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 |
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
PubMed
Title | Date | PubMed |
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Production of a bioactive sweetener steviolbioside via specific hydrolyzing ester linkage of stevioside with a β-galactosidase. | 2016 Apr 1 |
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Gene transcription and steviol glycoside accumulation in Stevia rebaudiana under polyethylene glycol-induced drought stress in greenhouse cultivation. | 2016 Sep |
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Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats. | 2016 Sep |
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Physico-chemical and sensory characteristics of steviolbioside synthesized from stevioside and its application in fruit drinks and food. | 2017 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 18:27:56 UTC 2019
by
admin
on
Tue Oct 22 18:27:56 UTC 2019
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Record UNII |
07GV37SOFN
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Record Status |
Validated (UNII)
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Record Version |
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-
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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
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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
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PRIMARY |
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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.
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