ISOFUCOSTEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H48O
Molecular Weight	412.6908
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	1
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(=C\C)C(C)C

InChI

InChIKey=OSELKOCHBMDKEJ-WGMIZEQOSA-N

InChI=1S/C29H48O/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/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2775538 | https://www.ncbi.nlm.nih.gov/pubmed/1186438 | https://www.ncbi.nlm.nih.gov/pubmed/5343809 | https://www.ncbi.nlm.nih.gov/pubmed/10576216 | https://www.ncbi.nlm.nih.gov/pubmed/24684169https://www.ncbi.nlm.nih.gov/pubmed/26455344 | https://www.ncbi.nlm.nih.gov/pubmed/28134973 | https://www.ncbi.nlm.nih.gov/pubmed/28637390 | https://www.ncbi.nlm.nih.gov/pubmed/23116181 | https://www.ncbi.nlm.nih.gov/pubmed/23994501

Fucosterol (24-ethylidene cholesterol) is a sterol that can be isolated from algae, seaweed and diatoms. Fucosterol exhibits various biological therapeutics, including anticancer, antidiabetic, antioxidant, hepatoprotective, antihyperlipidemic, antifungal, antihistaminic, anticholinergic, antiadipogenic, antiphotodamaging, anti-osteoporotic, blood cholesterol reducing, blood vessel thrombosis preventive and butyrylcholinesterase inhibitory activities. Fucosterol showed higher antiplasmodial activity as compared to chloroquine. Fucosterol showed the increase in the anti-oxidant enzymes such as hepatic cytosolic superoxide dismutase (SOD), catalase and glutathione peroxidase (GSH-px) activities in CCl4-intoxicated rats. Fucosterol inhibited adipogenesis of 3T3-L1 preadipocytes through modulation of FoxO signalling pathway. Fucosterol is a dual-LXR agonist. It is displayed moderate inhibitory activity against aldose reductase and PTP1B.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
LXR-alpha 10 Target ID: CHEMBL2808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23116181	Agonist 2678	464.0 nM [EC50]
LXR-beta 6 Target ID: CHEMBL4093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23116181	Agonist 2678	1391.0 nM [EC50]
lipid oxidation 20 Target ID: GO:0034440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14560919	Inhibitor 8297
Aldose reductase 44 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23994501	Inhibitor 8297	143.0 µM [IC50]
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23994501	Inhibitor 8297	77.13 µM [Ki]
FoxO signaling pathway 4 Target ID: map04068 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28134973	Modulator 828
Pancreatic triacylglycerol lipase 12 Target ID: CHEMBL1687677 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24684169	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15595413	Primary	Preclinical	Unknown Approved Use Unknown
Plasmodium falciparum malaria 63 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28637390	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28134973	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24684169	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.	1969 Oct	5348842
Incorporation of [2-14C] mevalonic acid into 28-isofucosterol by leaves of Pisum sativum.	1969 Oct	5343809
28-Isofucosterol: major sterol of a marine sponge.	1975 Jul-Aug	1186438
Inhibition of Mycobacterium tuberculosis growth by saringosterol from Lessonia nigrescens.	2001 Nov	11720535
Inhibitory activity on HIV-1 reverse transcriptase and integrase of a carmalol derivative from a brown Alga, Ishige okamurae.	2006 Aug	16775811
Kinetics and molecular docking studies of an anti-diabetic complication inhibitor fucosterol from edible brown algae Eisenia bicyclis and Ecklonia stolonifera.	2013 Oct 25	23994501

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

ISOFUCOSTEROL

Common Name

English

STIGMASTA-5,24(28)-DIEN-3.BETA.-OL, (Z)-

Systematic Name

English

STIGMASTA-5-CIS,24(28)-DIEN-3.BETA.-OL

Systematic Name

English

(Z)-STIGMASTA-5,24(28)-DIEN-3.BETA.-OL

Systematic Name

English

28-ISOFUCOSTEROL

Common Name

English

(24Z)-24-ETHYLCHOLESTA-5,24(28)-DIEN-3.BETA.-OL

Systematic Name

English

24-ETHYLCHOLESTA-5,24(28)Z-DIEN-3.BETA.-OL

Systematic Name

English

STIGMASTA-5,24(28)-DIEN-3-OL, (3.BETA.,24Z)-

Systematic Name

English

(24Z)-ETHYLIDENECHOLESTEROL

Systematic Name

English

24(Z)-ETHYLIDENECHOLEST-5-EN-3.BETA.-OL

Systematic Name

English

(Z)-24-ETHYLCHOLESTA-5,24(28)-DIEN-3.BETA.-OL

Systematic Name

English

Code System Code Type Description

PUBCHEM

5281326