| 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=CC=C(C=C2O1)[C@@H]3OC[C@@H]4[C@H]3CO[C@H]4C5=CC6=C(OCO6)C=C5
InChI
InChIKey=PEYUIKBAABKQKQ-NSMLZSOPSA-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
(-)-Sesamin is a lignan present in sesam oil and a number of medicinal plants. It exerts various pharmacological effects, such as prevention of hyperlipidemia, hypertension, and carcinogenesis. Moreover, (-)-sesamin has chemopreventive and anticancer activity in vitro and in vivo. (-)-Sesamin is an inhibitor of human mitochondrial Lon protease and DNA damage agents to activate the DNA damage checkpoints as well induce apoptosis in NSCLC cells. (-)-Sesamin is an antioxidant, showing effective 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Mice were treated with (-)-sesamin (25 and 50 mg/kg) orally once a day for 21 days prior to exposure to EF stress (0.6 mA, 1 s every 5 s, 3 min). Mice treated with (-)-sesamin (25 and 50 mg/kg) exhibited less severe decreases in the number of open arm entries and time spent on open arms in the elevated plus-maze test and the distance traveled in the open field test following exposure to chronic EF stress.
Route of Administration:
Oral
In PC12 cells, treatment with (-)-sesamin (25 uM) reduced 6-OHDA (100 uM)-induced cell death and induced transient extracellular signal-regulated kinase (ERK1/2) phosphorylation and Bad phosphorylation at Ser112 (BadSer112). In contrast, sustained ERK1/2 phosphorylation, p38 mitogen-activated protein kinase (p38MAPK) and c-Jun N-terminal kinase (JNK1/2) phosphorylation, and cleaved-caspase-3 activity, all of which were induced by 6-OHDA (100 uM), were inhibited by treatment with (-)-sesamin (25 uM).
SUBSTANCE RECORD
