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
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-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
| 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 |
DescriptionSources: http://www.drugfuture.com/chemdata/asarinin.html | https://www.ncbi.nlm.nih.gov/pubmed/23282922https://www.ncbi.nlm.nih.gov/pubmed/24232457 | http://www.sciencedirect.com/science/article/pii/S1756464615004065 | https://www.ncbi.nlm.nih.gov/pubmed/25267105 | https://www.ncbi.nlm.nih.gov/pubmed/22818712
Sources: http://www.drugfuture.com/chemdata/asarinin.html | https://www.ncbi.nlm.nih.gov/pubmed/23282922https://www.ncbi.nlm.nih.gov/pubmed/24232457 | http://www.sciencedirect.com/science/article/pii/S1756464615004065 | https://www.ncbi.nlm.nih.gov/pubmed/25267105 | https://www.ncbi.nlm.nih.gov/pubmed/22818712
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0042554 |
|||
Target ID: CHEMBL248 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24232457 |
|||
Target ID: CHEMBL2823 |
|||
Target ID: CHEMBL612641 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24687738 |
|||
Target ID: CHEMBL613088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24687738 |
|||
Target ID: CHEMBL614982 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24687738 |
|||
Target ID: CHEMBL614987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24687738 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
|||
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2015-03 |
|
| New benzo[c]phenanthridine and benzenoid derivatives, and other constituents from Zanthoxylum ailanthoides: Effects on neutrophil pro-inflammatory responses. | 2013-11-13 |
|
| (±)-Asarinin. | 2013-01 |
|
| Comparative study of sesame lignans (sesamin, episesamin and sesamolin) affecting gene expression profile and fatty acid oxidation in rat liver. | 2009-02 |
|
| [Synthesis of DL-asarinin and DL-sesamin]. | 1957-01 |
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 21:29:04 GMT 2025
by
admin
on
Mon Mar 31 21:29:04 GMT 2025
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| Record UNII |
C3RVX72NMG
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| Record Status |
Validated (UNII)
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| Record Version |
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C054125
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m2082
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