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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H50O
Molecular Weight 414.7067
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .GAMMA.-SITOSTEROL

SMILES

[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=KZJWDPNRJALLNS-FBZNIEFRSA-N
InChI=1S/C29H50O/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/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

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
Clionasterol: a potent inhibitor of complement component C1.
2003 Feb
Antidiabetic activity of γ-sitosterol isolated from Lippia nodiflora L. in streptozotocin induced diabetic rats.
2011 Sep 30
Fucosterol, a sterol extracted from Sargassum fusiforme, shows antidepressant and anticonvulsant effects.
2015 Dec 5
Major Phytochemical as γ-Sitosterol Disclosing and Toxicity Testing in Lagerstroemia Species.
2017
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 Fri Dec 15 15:57:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:51 GMT 2023
Record UNII
5LI01C78DD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.GAMMA.-SITOSTEROL
MI  
Common Name English
CLIONASTEROL
Common Name English
24S-ETHYLCHOLEST-5-EN-3.BETA.-OL
Common Name English
22,23-DIHYDROPORIFERASTEROL
Common Name English
STIGMAST-5-EN-3.BETA.-OL, (24S)-
Systematic Name English
(24S)-STIGMAST-5-EN-3.BETA.-OL
Systematic Name English
24.BETA.-ETHYLCHOLEST-5-EN-3.BETA.-OL
Systematic Name English
FUCOSTEROL, .BETA.-DIHYDRO-
Common Name English
24.BETA.-ETHYLCHOLESTEROL
Systematic Name English
.BETA.-DIHYDROFUCOSTEROL
Common Name English
.GAMMA.-SITOSTEROL [MI]
Common Name English
(3.BETA.,24S)-STIGMAST-5-EN-3-OL
Systematic Name English
STIGMAST-5-EN-3-OL, (3.BETA.,24S)-
Systematic Name English
Code System Code Type Description
MESH
C025473
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID801015721
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
PUBCHEM
457801
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
MERCK INDEX
m9965
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY Merck Index
CHEBI
132823
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
FDA UNII
5LI01C78DD
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
CAS
83-47-6
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-481-1
Created by admin on Fri Dec 15 15:57:51 GMT 2023 , Edited by admin on Fri Dec 15 15:57:51 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS