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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
Structure of .GAMMA.-SITOSTEROL MONOHYDRATE

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
4.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

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
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
by admin
on Wed Apr 02 01:22:00 GMT 2025
Edited
by admin
on Wed Apr 02 01:22:00 GMT 2025
Record UNII
8WTG470OLX
Record Status Validated (UNII)
Record Version
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Name Type Language
.GAMMA.-SITOSTEROL MONOHYDRATE [MI]
Preferred Name English
.GAMMA.-SITOSTEROL MONOHYDRATE
Common Name English
STIGMAST-5-EN-3-OL, MONOHYDRATE, (3.BETA.,24S)-
Common Name English
Code System Code Type Description
FDA UNII
8WTG470OLX
Created by admin on Wed Apr 02 01:22:00 GMT 2025 , Edited by admin on Wed Apr 02 01:22:00 GMT 2025
PRIMARY
CAS
6131-86-8
Created by admin on Wed Apr 02 01:22:00 GMT 2025 , Edited by admin on Wed Apr 02 01:22:00 GMT 2025
PRIMARY
PUBCHEM
133082557
Created by admin on Wed Apr 02 01:22:00 GMT 2025 , Edited by admin on Wed Apr 02 01:22:00 GMT 2025
PRIMARY
MERCK INDEX
m9965
Created by admin on Wed Apr 02 01:22:00 GMT 2025 , Edited by admin on Wed Apr 02 01:22:00 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE