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
[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
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 |
---|---|---|---|
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 |
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Target ID: P22680 Gene ID: 1581.0 Gene Symbol: CYP7A1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9072406 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Differential in vitro anti-HIV activity of natural lignans. | 1990 Nov-Dec |
|
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 |
|
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system. | 2012 |
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Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway. | 2013 Feb 6 |
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Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages. | 2013 Mar 7 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23888002
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24740895
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.
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SUBSTANCE RECORD