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

[H][C@@]12CCC(C)=C3C(=O)C=C(C)[C@]3([H])[C@@]1([H])OC(=O)[C@H]2C

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 47 Target ID: CHEMBL402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27023504	Inhibitor 8297		3.88 µM [IC50]
Oxidative Stress 160 Target ID: WP173 Sources: DOI: 10.20538/1682-0363-2013-1-43-48	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27023504	Primary	Basic research	Unknown Approved Use Unknown
Hyperlipidemia 80 Sources: DOI: 10.20538/1682-0363-2013-1-43-48	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1915817	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.	2002 May	12011356
Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group.	2002 Nov-Dec	12562079
TLC and HPLC characteristics of desacetylmatricarin, leucodin, achillin and their 8alpha-angeloxy-derivatives.	2003 Jul	12889533
Structure elucidation and complete NMR spectral assignments of two new sesquiterpene lactone xylosides from Lactuca triangulata.	2008 Dec	18785195
Dehydro-leucodin: a guaiane-type sesquiterpene lactone.	2011 Dec 1	22199945
A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC.	2012	21995805
Guaianolides and volatile compounds in chamomile tea.	2012 Jun	22410959
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 Mar 25	27023504
Effect of guaianolides in the meiosis reinitiation of amphibian oocytes.	2017 Feb	27806737
The natural sesquiterpene lactones arglabin, grosheimin, agracin, parthenolide, and estafiatin inhibit T cell receptor (TCR) activation.	2018 Feb	29216473

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 `Sat Dec 16 10:02:40 GMT 2023` Edited by `admin` on `Sat Dec 16 10:02:40 GMT 2023`
Record UNII	1G2W00IRUI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

LEUKODIN, (+)-

Brand Name

English

DESACETOXYMATRICARIN [MI]

Common Name

English

LEUKOMISIN

Brand Name

English

DEACETOXYMATRICARIN

Common Name

English

Code System Code Type Description

PUBCHEM

167683