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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 of ASARININ

SMILES

[H][C@@]12CO[C@H](C3=CC=C4OCOC4=C3)[C@]1([H])CO[C@H]2C5=CC=C6OCOC6=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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P00533|||Q9GZX1
Gene ID: 1956.0
Gene Symbol: EGFR
Target Organism: Homo sapiens (Human)
Target ID: P22680
Gene ID: 1581.0
Gene Symbol: CYP7A1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides.
2003 Apr
Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats.
2005 Jan
Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress.
2008 Oct-Dec
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats.
2010 Jan 5
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system.
2012
Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway.
2014 Jan 13
Patents

Sample Use Guides

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
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 Fri Dec 15 20:39:33 GMT 2023
Edited
by admin
on Fri Dec 15 20:39:33 GMT 2023
Record UNII
333JW641ML
Record Status Validated (UNII)
Record Version
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Name Type Language
ASARININ
MI  
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
(-)-ASARININ
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
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY
FDA UNII
333JW641ML
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY
PUBCHEM
11869417
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY
MERCK INDEX
m2082
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY Merck Index
MESH
C054125
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY
CAS
133-04-0
Created by admin on Fri Dec 15 20:39:33 GMT 2023 , Edited by admin on Fri Dec 15 20:39:33 GMT 2023
PRIMARY