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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.[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](CC)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
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
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.
Name Type Language
.GAMMA.-SITOSTEROL MONOHYDRATE
Common Name English
STIGMAST-5-EN-3-OL, MONOHYDRATE, (3.BETA.,24S)-
Common Name English
.GAMMA.-SITOSTEROL MONOHYDRATE [MI]
Common Name English
Code System Code Type Description
FDA UNII
8WTG470OLX
Created by admin on Sat Dec 16 14:49:06 GMT 2023 , Edited by admin on Sat Dec 16 14:49:06 GMT 2023
PRIMARY
CAS
6131-86-8
Created by admin on Sat Dec 16 14:49:06 GMT 2023 , Edited by admin on Sat Dec 16 14:49:06 GMT 2023
PRIMARY
PUBCHEM
133082557
Created by admin on Sat Dec 16 14:49:06 GMT 2023 , Edited by admin on Sat Dec 16 14:49:06 GMT 2023
PRIMARY
MERCK INDEX
m9965
Created by admin on Sat Dec 16 14:49:06 GMT 2023 , Edited by admin on Sat Dec 16 14:49:06 GMT 2023
PRIMARY