ASARININ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H18O6
Molecular Weight	354.3533
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1OC2=C(O1)C=C(C=C2)[C@H]3OC[C@@H]4[C@H]3CO[C@H]4C5=CC6=C(OCO6)C=C5

InChI

InChIKey=PEYUIKBAABKQKQ-FQZPYLGXSA-N

InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19-,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H18O6
Molecular Weight	354.3533
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23888002 | https://www.ncbi.nlm.nih.gov/pubmed/24687738

Asarinin, an urofuran lignan, is the epimer of sesamin. Asarinin is listed in Chinese Pharmacopoeia and used as a quality control (QC) index of crude herbs by the State Food and Drug Administration of China. Asarinin exhibits several biological activities such as decreasing cholesterol levels, exhibiting antihypertensive and antiangiogenic properties and providing immunosuppressive and hepatoprotective activities. Asarinin can also inhibit myocardial injury in metabolic syndrome of rats and decrease the possibility of acute heart transplant rejection. Sesamin was first isolated from sesame seed oil, while asarinin was first isolated from prickly ash bark. Both sesamin and asarinin have been shown to act as insecticidal synergists with pyrethrins.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Epidermal growth factor receptor 49 Target ID: P00533\|\|\|Q9GZX1 Gene ID: 1956.0 Gene Symbol: EGFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24740895	Antagonist 2849
Cholesterol 7-alpha-monooxygenase 2 Target ID: P22680 Gene ID: 1581.0 Gene Symbol: CYP7A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9072406	Activator 1447
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://books.google.ru/books?id=KzHpCAAAQBAJ&pg=PA130&lpg=PA130&dq=ASARININ retrieved from Bioassay Methods in Natural Product Research and Drug Development edited by Lars Bohlin, Jan G. Bruhn, p.130	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9072406	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway.	2014-01-13	24211423
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.	2013-03-07	23337743
Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway.	2013-02-06	23317420
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system.	2012	22919443
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats.	2010-01-05	19835851
Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress.	2008-08-21	19794909
Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats.	2005-01	15635186
Antifungal constituents of Melicope borbonica.	2004-07	15305313
Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes.	2003-12	14974737
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides.	2003-04	12709897
Differential in vitro anti-HIV activity of natural lignans.	1990-11-01	1965681

Patents

Sample Use Guides

In Vivo Use Guide

Rats: The validated method was applied in a pharmacokinetic study of sesamin and asarinin in rat plasma after 2.8 g/kg of A. heterotropoides extract (equivalent to 12.1 and 4.32 mg/kg for asarinin and sesamin, respectively) was orally administered.

Route of Administration: Oral

In Vitro Use Guide

The inhibition rates of asarinin on EGFR HEK293 cell line were 2.5 ± 1.22, 6.3 ± 1.25, 8.7 ± 1.47, 10.3 ± 2.31, 13.8 ± 1.83, and 23.2 ± 3.39 at the concentrations of 0.1, 0.4, 1.6, 6.4, 25.6, and 102.4 uM, respectively. In the range of 0.10–102.4 uM, gefitinib and asarinin showed obvious and dose-dependent inhibition activity.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:13:07 GMT 2025` Edited by `admin` on `Mon Mar 31 20:13:07 GMT 2025`
Record UNII	333JW641ML
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(-)-ASARININ

Preferred Name

English

ASARININ

Common Name

English

ASARININ, (-)-

Common Name

English

1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1R-(1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.))-

Common Name

English

1,3-BENZODIOXOLE, 5,5'-((1R,3AS,4S,6AS)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-

Common Name

English

L-ASARININ

Common Name

English

(-)-EPISESAMIN

Common Name

English

XANTHOXYLN S

Common Name

English

ASARININ [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID501033823