DESACETOXYMATRICARIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H18O3
Molecular Weight	246.3016
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@@H]2CCC(C)=C3[C@@H]([C@H]2OC1=O)C(C)=CC3=O

InChI

InChIKey=BJPSSVHNEGMBDQ-NUZBWSBOSA-N

InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H18O3
Molecular Weight	246.3016
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: DOI: 10.1016/S0040-4020(01)82761-7 | https://www.ncbi.nlm.nih.gov/pubmed/12011356 | https://www.ncbi.nlm.nih.gov/pubmed/27023504 | Eisenman, S.W. et al. (2012) Medicinal Plants of Central Asia: Uzbekistan and Kyrgyzstan, page.44, retrieved from: https://books.google.ru/books?id=PjsAmHe7Cd4C

Desacetoxymatricarin is a sesquiterpene lactone found in the genus Artemisia and in the form of 8-hydroxy and acetoxy derivatives in the genus Achillea. The formation of desacetoxymatricarin from (+)-costunolide probably involves more than one enzyme, including a cytochrome P450 enzyme. It is a potent 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitor. Desacetoxymatricarin showed the highest anti-hypercholesterolemic potential. Oligvon, a preparation containing desacetoxymatricarin, is used to prevent and treat artherosclerosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
HMG-CoA reductase 49 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27023504	Inhibitor 8504		3.88 µM [IC50]
Oxidative Stress 162 Target ID: WP173 Sources: DOI: 10.20538/1682-0363-2013-1-43-48	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27023504	Primary	Basic research	Unknown Approved Use Unknown
Hyperlipidemia 82 Sources: DOI: 10.20538/1682-0363-2013-1-43-48	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 76 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1915817	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The natural sesquiterpene lactones arglabin, grosheimin, agracin, parthenolide, and estafiatin inhibit T cell receptor (TCR) activation.	2018-02	29216473
Effect of guaianolides in the meiosis reinitiation of amphibian oocytes.	2017-02	27806737
The Chemical Composition of Achillea wilhelmsii C. Koch and Its Desirable Effects on Hyperglycemia, Inflammatory Mediators and Hypercholesterolemia as Risk Factors for Cardiometabolic Disease.	2016-03-25	27023504
Guaianolides and volatile compounds in chamomile tea.	2012-06	22410959
A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC.	2012	21995805
Dehydro-leucodin: a guaiane-type sesquiterpene lactone.	2011-12-01	22199945
[Effect of leucomisine on cell and humoral immunity indices].	2010-01-26	20095397
[Experimental evaluation of the antibacterial and phagocytosis-stimulating properties of leucomisine].	2009-11-26	19928574
Structure elucidation and complete NMR spectral assignments of two new sesquiterpene lactone xylosides from Lactuca triangulata.	2008-12	18785195
TLC and HPLC characteristics of desacetylmatricarin, leucodin, achillin and their 8alpha-angeloxy-derivatives.	2003-07	12889533
Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group.	2003-02-04	12562079
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.	2002-05	12011356
Desacetylmatricarin, an anti-allergic component from Taraxacum platycarpum.	1998-08	9741305
The gastric cytoprotective effect of several sesquiterpene lactones.	1990-07-01	2095374

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10 mg/kg

Route of Administration: Unknown

In Vitro Use Guide

Desacetoxymatricarin showed a potent inhibitory activity upon the beta-hexosaminidase release from RBL-2H3 cells in a dose-dependent manner and the IC50 was 80 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:59:18 GMT 2025` Edited by `admin` on `Mon Mar 31 22:59:18 GMT 2025`
Record UNII	1G2W00IRUI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEUKODIN, (+)-

Preferred Name

English

DESACETOXYMATRICARIN

Common Name

English

AZULENO(4,5-B)FURAN-2,7-DIONE, 3,3A,4,5,9A,9B-HEXAHYDRO-3,6,9-TRIMETHYL-, (3S,3AS,9AS,9BS)-

Systematic Name

English

11,13-DIHYDRO-DEHYDROLEUCODINE

Common Name

English

DESACETOXYMATRICARIN [MI]

Common Name

English

LEUKOMISIN

Brand Name

English

DEACETOXYMATRICARIN

Common Name

English

Code System Code Type Description

PUBCHEM

167683