Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C29H50O.H2O |
| Molecular Weight | 432.722 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChI
InChIKey=WPBUQWHGPFAIPS-WZKMZHGQSA-N
InChI=1S/C29H50O.H2O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6;/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3;1H2/t20-,21+,23+,24+,25-,26+,27+,28+,29-;/m1./s1
| Molecular Formula | C29H50O |
| Molecular Weight | 414.7067 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
gamma-sitosterol is a naturally occurring plant steroid isolatable from plants of the genus Lagerstroemia. Gamma-sitosterol is a potent inhibitor of the complement component C1 complex, and it has demonstrated potential as a diabetic treatment in rats. Gamma-sitosterol is a stereoisomer of beta-sitosterol, which sees wide use as an over the counter natural supplement. However, plant extracts containing gamma-sitosterol have demonstrated toxicity on in-vitro human cell assays; which may discourage use as a natural supplement.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0005602 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12624828 |
4.1 µM [IC50] | ||
Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25912799 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Major Phytochemical as γ-Sitosterol Disclosing and Toxicity Testing in Lagerstroemia Species. | 2017 |
|
| Fucosterol, a sterol extracted from Sargassum fusiforme, shows antidepressant and anticonvulsant effects. | 2015-12-05 |
|
| Antidiabetic activity of γ-sitosterol isolated from Lippia nodiflora L. in streptozotocin induced diabetic rats. | 2011-09-30 |
|
| Clionasterol: a potent inhibitor of complement component C1. | 2003-02 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21658378
Gamma-sitosterol was administered to diabetic rats as a once-daily oral dose of 20 mg/kg bw for 21 days. The dosing regime resulted in significant decrease in blood glucose and glycosylated hemoglobin coupled with a significant increase in plasma insulin level, body weight, and food intake. Gamma-sitosterol also exhibited antihyperlipidemic activity as evidenced by a significant decrease in serum total cholesterol, triglycerides and VLDL-cholesterol along with increased HDL-cholesterol levels.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28191023
Human Peripheral Blood Mononuclear Cells (PBMC) were isolated from sodium heparin anticoagulated venous blood from a blood bank. Cells were suspended at a concentration of 10^6 cells/mL in RPMI-1640 medium with 2 mM L-glutamine and 25 mM HEPES, supplemented with 10% FBS, 5 μg/mL phytohemagglutinin (PHA), 100 μg/mL streptomycin, and 100 U/mL penicillin. Cells were treated with plant ethanol extracts from the genus Lagerstroemia for 4 hours; gamma-sitosterol content varied from 14.70 - 34.44%. Cell viability was determined to reveal the cytotoxicity of the plant extracts. Most plant extracts exhibited modest cytotoxicity with the exception of extracts from L. speciosa which exhibited an IC50 of 0.24 mg/mL corresponding to an LD50 of 811.78 mg/kg, which is in the range of WHO Class III toxic chemicals.
| Substance Class |
Chemical
Created
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| Record UNII |
8WTG470OLX
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| Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE |