Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C38H60O18 |
Molecular Weight | 804.8722 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 21 / 21 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]7(O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@@]23C[C@]4(CC2=C)CC[C@]5([H])[C@@](C)(CCC[C@@]5(C)[C@]4([H])CC3)C(=O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O
InChI
InChIKey=UEDUENGHJMELGK-HYDKPPNVSA-N
InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(50)55-32-29(49)26(46)23(43)18(13-40)52-32)21(37)6-10-38(16,15-37)56-33-30(27(47)24(44)19(14-41)53-33)54-31-28(48)25(45)22(42)17(12-39)51-31/h17-33,39-49H,1,4-15H2,2-3H3/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29-,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1
Stevioside is an ent-kaurene type diterpenoid glycoside isolated
from leaves of Stevia rebaudiana (Bertoni) Bertoni, a
perennial herb of the asteraceae (compositae) family.
Stevioside and related compounds are responsible for the
sweet taste of Stevia leaves. Stevioside is an intense sweetener and
the extract of its source (S. rebaudiana) finds extensive use in
countries like Japan, China, Russia, Korea, Paraguay,
Argentina, Indonesia, Malaysia, Australia, New Zealand,
South America, and others, to sweeten local teas, medicines,
food, and beverages. Stevia leaves are also in use
for their medicinal benefits in hypertension, obesity, topical
dressing for wounds, and other skin disorders. Oral stevioside is not taken up by the human body (or
the uptake is extremely low) and none of the digestive
enzymes from the gastro-intestinal tract of different animals
and human body are able to degrade stevioside into steviol. A number of studies have suggested that, beside sweetness, stevioside along with related compounds, which include rebaudioside A, steviol and isosteviol may also offer therapeutic benefits, as they have anti-hyperglycemic, anti-hypertensive, anti-inflammatory, anti-tumor, anti-diarrheal, diuretic, and immunomodulatory actions.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213347
Curator's Comment: Stevioside and rebaudioside were first isolated by two French chemists, Bridel and Lavielle.
Approval Year
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg 3 times / day multiple, oral Studied dose Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy n = 168 Health Status: unhealthy Condition: essential hypertension Sex: M+F Food Status: UNKNOWN Population Size: 168 Sources: |
Disc. AE: Nausea alone, Dizziness... AEs leading to discontinuation/dose reduction: Nausea alone (1 pt) Sources: Dizziness (1 pt) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 1 pt Disc. AE |
500 mg 3 times / day multiple, oral Studied dose Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy n = 168 Health Status: unhealthy Condition: essential hypertension Sex: M+F Food Status: UNKNOWN Population Size: 168 Sources: |
Nausea alone | 1 pt Disc. AE |
500 mg 3 times / day multiple, oral Studied dose Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy n = 168 Health Status: unhealthy Condition: essential hypertension Sex: M+F Food Status: UNKNOWN Population Size: 168 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
no | |||
no | ||||
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
no | |||
no | ||||
no | ||||
weak [IC50 62.6 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29655729/ |
weak | |||
yes [IC50 11.1 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Km 12.5 uM] | ||||
yes [Km 6.9 uM] | ||||
yes |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213347
Stevioside was administered at a dose of 250 mg thrice a day for 1 year to 60 hypertensive volunteers. After 3 months the systolic and diastolic blood pressure decreased significantly and the effect was also found to be persisting.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213347
High concentrations of stevioside (2–5 uM) and steviol
(0.2–0.8 uM) were observed to decrease cell viability in
T84, Caco-2, and HT29 cells (assayed by MTT method).
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Classification Tree | Code System | Code | ||
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JECFA EVALUATION |
INS-960
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DSLD |
2560 (Number of products:5)
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CODEX ALIMENTARIUS (GSFA) |
INS-960
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100000176630
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0YON5MXJ9P
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DTXSID7021281
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C012043
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SUB191567
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57817-89-7
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0YON5MXJ9P
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37106
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260-975-5
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9271
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1622408
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442089
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Stevioside
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m10209
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PRIMARY | Merck Index |
ACTIVE MOIETY