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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-WZBLMQSHSA-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+/m0/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, (+)- ((+)-episesamin), an abundant lignan in sesame seed, has been identified as an active principle in an aqueous extract of Lindera obtusiloba (Japanese Spicebush) with a strong anti-inflammatory potential. (+)-episesamin (ES) is known to block the TNF-α-induced mitogenic VSMC response. Protective effect of (+)-episesamin against PDGF-BB-induced activation of vascular smooth muscle cells is mediated by induction of haem oxygenase-1 and inhibition of mitogenic signalling. ES interferes with inflammation-associated VSMC activation and subsequent decreased proliferation and migration due to anti-oxidative properties and impaired activation of NF-ĸB, known contributors to atherogenesis. These results suggest ES as a complemental treatment of VSMC specific vascular diseases such as atherosclerosis. (+)-Episesamin inhibits adipogenesis and exerts anti-inflammatory effects in 3T3-L1 (pre)adipocytes by sustained Wnt signaling, down-regulation of PPARγ and induction of iNOS. (+)-episesamin seems to be the active drug in the L. obtusiloba extract being responsible for the inhibition of adipogenesis and, thus, should be evaluated as a novel potential complementary treatment for obesity.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Synthesis of DL-asarinin and DL-sesamin].
1957 Jan
Comparative study of sesame lignans (sesamin, episesamin and sesamolin) affecting gene expression profile and fatty acid oxidation in rat liver.
2009 Feb
(±)-Asarinin.
2013 Jan
New benzo[c]phenanthridine and benzenoid derivatives, and other constituents from Zanthoxylum ailanthoides: Effects on neutrophil pro-inflammatory responses.
2013 Nov 13
The lignan (+)-episesamin interferes with TNF-α-induced activation of VSMC via diminished activation of NF-ĸB, ERK1/2 and AKT and decreased activity of gelatinases.
2015 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: ASARININ, (+)- ((+)-episesamin) at 1-10 um reduced basal and TNF-α-induced VSMC proliferation and migration. https://www.ncbi.nlm.nih.gov/pubmed/25267105
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:18:39 GMT 2023
Edited
by admin
on Sat Dec 16 05:18:39 GMT 2023
Record UNII
C3RVX72NMG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASARININ, (+)-
Common Name English
ASARININ D-FORM [MI]
Common Name English
1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1S-(1.ALPHA.,3A.ALPHA.,4.BETA.,6A.ALPHA.))-
Common Name English
(+)-ASARININ
Common Name English
ISOSESAMIN
Common Name English
1H,3H-FURO(3,4-C)FURAN, 3A.BETA.,4,6,6A.BETA.-TETRAHYDRO-1.ALPHA.,4.BETA.-BIS(3,4-(METHYLENEDIOXY)PHENYL)-, (+)-
Common Name English
EPISESAMIN
Common Name English
(+)-EPISESAMIN
Common Name English
D-ASARININ
Common Name English
Code System Code Type Description
PUBCHEM
101612
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY
MESH
C054125
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID201033462
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY
FDA UNII
C3RVX72NMG
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY
CAS
133-03-9
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY
MERCK INDEX
m2082
Created by admin on Sat Dec 16 05:18:39 GMT 2023 , Edited by admin on Sat Dec 16 05:18:39 GMT 2023
PRIMARY Merck Index