SESAMOLIN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606 | https://www.ncbi.nlm.nih.gov/pubmed/23674992 | https://www.ncbi.nlm.nih.gov/pubmed/9614163 | https://www.ncbi.nlm.nih.gov/pubmed/25472416

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 Target	Pharmacology	Potency
ERK1 and ERK2 cascade 8 Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26298637	Activator 1430
lipid oxidation 20 Target ID: GO:0034440 Sources: DOI: 10.1007/BF02634903 \| https://www.ncbi.nlm.nih.gov/pubmed/25472416 \| https://www.ncbi.nlm.nih.gov/pubmed/9614163	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11254875	Activator 1430
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606	Inhibitor 8297	3.57 µM [IC50]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606	Inhibitor 8297	3.93 µM [IC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606	Inhibitor 8297	0.69 µM [IC50]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606	Inhibitor 8297	1.33 µM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22894606	Inhibitor 8297	0.86 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Burkitt’s lymphoma 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26298637	Primary	Basic research	Unknown Approved Use Unknown
Lymphoid leukemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11254875	Primary	Basic research	Unknown Approved Use Unknown
Cerebral ischemia 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23674992	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Sesamolin enhances NK cell lysis activity by increasing the expression of NKG2D ligands on Burkitt's lymphoma cells.	2015 Oct	26298637
Preparative separation of sesamin and sesamolin from defatted sesame meal via centrifugal partition chromatography with consecutive sample injection.	2016 Feb 1	26773888
Determination and purification of sesamin and sesamolin in sesame seed oil unsaponified matter using reversed-phase liquid chromatography coupled with photodiode array and tandem mass spectrometry and high-speed countercurrent chromatography.	2016 Oct	27558960
Magnetic solid-phase extraction based on graphene oxide for the determination of lignans in sesame oil.	2017 Feb 15	27664640

Patents

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.

Name

Type

Language

SESAMOLIN

Common Name

English

1,3-BENZODIOXOL-5-YL (1R,3AR,4S,6AR)-4-(1,3-BENZODIOXOL-5-YL)PERHYDROFURO(3,4-C)FURAN-1-YL ETHER

Common Name

English

(1S,3AR,4R,6AR)-5-(4-(1,3-BENZODIOXOL-5-YLOXY)TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1-YL)-1,3-BENZODIOXOLE

Common Name

English

SESAMOLIN [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

101746