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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H18O7
Molecular Weight 370.3527
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SESAMOLIN

SMILES

[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2OC5=CC=C6OCOC6=C5

InChI

InChIKey=ZZMNWJVJUKMZJY-AFHBHXEDSA-N
InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

HIDE SMILES / InChI

Description

Sesamolin from Sesamun indicum seeds plays important role in plant defense, such as antifeedant as well as potent antioxidants and insecticides. Sesaminol has potent inhibition of cytochrome P450 (CYPs). The neuroprotective effect of sesamolin was also observed in vivo using gerbils subjected to a focal cerebral ischemia induced by occlusion of the right common carotid artery and the right middle cerebral artery. Lipid peroxidation activity, measured as 2-thiobarbituric acid reactive substances, was significantly lower in the kidneys and liver of the sesamolin-fed rats than in the controls.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.57 µM [IC50]
3.93 µM [IC50]
0.69 µM [IC50]
1.33 µM [IC50]
0.86 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 0.6 or 2 g/kg for 10 days.
Route of Administration: Oral
In Vitro Use Guide
Raji cells were cultured with sesamolin (40 μg/mL) in the presence or absence of 20 μM of the ERK 1/2 inhibitor PD98059 (PD). The control cells were treated with just DMSO as a solvent for sesamolin and PD98059. After 72 h, cells were harvested and used for the analysis of NKG2D ligands with flow cytometry. The ability of sesamolin (Se) to upregulate the expression of ULBP-1, ULBP-2, and MIC-A/B was significantly suppressed by PD98059 (PD). In addition, sesamolin's ability to increase the NK cell (NK92-MI) mediated lysis of Raji was significantly attenuated by the ERK 1/2 inhibitor PD98059.