β-sitosterol

First approved in 1956

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 Search

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-VJSFXXLFSA-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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10796740 | https://www.ncbi.nlm.nih.gov/pubmed/12579296 | https://www.luckyvitamin.com/c-2091-beta-sitosterol | https://www.vitamart.ca/beta-sitosterol/ | https://www.webmd.com/vitamins-supplements/ingredientmono-939-beta-sitosterol.aspx | https://www.ncbi.nlm.nih.gov/pubmed/345413 | https://www.ncbi.nlm.nih.gov/pubmed/26199569

Beta-sitosterol is one of the main dietary phytosterols found in plants which have a similar skeleton as cholesterol. In human clinical trials, beta-sitosterol has been shown to have cholesterol-lowering effects and to relieve symptoms of benign prostatic hyperplasia. There has been a large amount of basic research conducted for potential applications of beta-sitosterol in a diverse range of conditions including cervical cancer, breast cancer, cystic fibrosis, and others. Beta-sitosterol is available over the counter as a natural health supplement and is marketed for a wide range of applications including headaches, tuberculosis, allergies, cancers, fibromyalgia, lupus, asthma, hair loss and many others.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Caspase-3 21 Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12579296	Activator 1430
Protein kinase C alpha type 5 Target ID: P17252 Gene ID: 5578.0 Gene Symbol: PRKCA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28553226	Interacts 323

Conditions

Condition	Modality	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10796740	Primary	Natural Metabolite	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12579296	Primary	Natural Metabolite	Unknown Approved Use Unknown
Sitosterolemia 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00531128	Primary	Natural Metabolite	Unknown Approved Use Unknown
Cystic fibrosis 120 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28553226	Primary	Natural Metabolite	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26199569	Primary	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The influence of beta-sitosterol on biliary cholesterol saturation and bile acid kinetics in man.	1978	345413
Beta-sitosterols for benign prostatic hyperplasia.	2000	10796740
Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells.	2003 Mar-Apr	12579296
Dietary supplements for benign prostatic hyperplasia: an overview of systematic reviews.	2012 Nov	22883375
Effect of β-sitosterol on the expression of HPV E6 and p53 in cervical carcinoma cells.	2015	26199569

Patents

Sample Use Guides

In Vivo Use Guide

Over 6 to 8 weeks beta-sitosterol supplementation of 12 g/day resulted in an average of 11% decrease in serum cholesterol and a 12% decrease in biliary cholesterol saturation.

Route of Administration: Oral

In Vitro Use Guide

Human cervical cancer cell lines, Caski and HeLa, were cultured in RPMI-1640 and supplemented with 10% foetal bovine serum and incubated at 37 deg-c in an atmosphere with 5% CO2. Cells were treated with 20 umol/L of beta-sitosterol for 48 hours and examined for changes by light microscopy, electron microscopy, and transmission electron microscopy. Changes in mRNA and protein expression were quantified using Real-Time qPCR and western blots. The treatment with beta-sitosterol reduced expression of PCNA, increased p53 mRNA, decreased the amount of HPV E6 transcripts. Cells treated with beta-sitosterol also exhibited loss of cell surface microvilli and increased electron density in the cell membrane.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:47 GMT 2023` Edited by `admin` on `Fri Dec 15 15:05:47 GMT 2023`
Record UNII	S347WMO6M4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

β-sitosterol

Common Name

English

.ALPHA.-PHYTOSTEROL

Common Name

English

(3.BETA.)-STIGMAST-5-EN-3-OL

Systematic Name

English

BETA-SISTOSTEROL

Common Name

English

BETAPROST

Common Name

English

PROSTASAL

Brand Name

English

AZUPROSTAT

Common Name

English

BETA SITOSTEROL

Common Name

English

BETA-SITOSTEROL (CONSTITUENT OF STINGING NETTLE) [DSC]

Common Name

English

SITOSTEROL, .BETA.

Common Name

English

.BETA.-SITOSTEROL [MI]

Common Name

English

SITOSTERIN

Common Name

English

HARZOL

Brand Name

English

BETA-SITOSTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

SITOSTEROL, BETA

Common Name

English

22,23-DIHYDROSTIGMASTEROL

Common Name

English

CUPREOL

Common Name

English

RHAMNOL

Common Name

English

NSC-18173

Code

English

SKF 14463

Code

English

QUEBRACHOL

Common Name

English

BETA-SITOSTEROL [USP-RS]

Common Name

English

BETA-SITOSTEROL [INCI]

Common Name

English

SITOSTEROL [MART.]

Common Name

English

.BETA.-SITOSTEROL (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]

Common Name

English

Beta-sitosterol [WHO-DD]

Common Name

English

24.BETA.-ETHYL-.DELTA.(SUP 5)-CHOLESTEN-3.BETA.-OL

Common Name

English

BETA SITOSTEROL [VANDF]

Common Name

English

NSC-8096

Code

English

.DELTA.(SUP 5)-STIGMASTEN-3.BETA.-OL

Common Name

English

CINCHOL

Common Name

English

SITOSTEROL, BETA-

Common Name

English

.BETA.-SITOSTEROL (CONSTITUENT OF PYGEUM) [DSC]

Common Name

English

BETA-SITOSTEROL

Official Name

English

.ALPHA.-DIHYDROFUCOSTEROL

Common Name

English

NSC-49083

Code

English

Classification Tree Code System Code

DSLD

1062 (Number of products:256)