SESAMIN, (-)-

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

Structure Search

SMILES

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24556122 | https://www.ncbi.nlm.nih.gov/pubmed/21077998 | https://www.ncbi.nlm.nih.gov/pubmed/20614822

(-)-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

Targets

Primary Target	Pharmacology	Condition	Potency
Lon protease homolog, mitochondrial 1 Target ID: P36776 Gene ID: 9361.0 Gene Symbol: LONP1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21077998	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21077998	Activator 1430
Phospholipase C-gamma-1 1 Target ID: CHEMBL3964 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15554262	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27995494	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25747493	Secondary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24556122 https://www.ncbi.nlm.nih.gov/pubmed/21077998 https://www.ncbi.nlm.nih.gov/pubmed/20614822 https://www.ncbi.nlm.nih.gov/pubmed/15554262	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography.	2002 Jul	12376305
Inhibition of prostaglandin E(2) production by taiwanin C isolated from the root of Acanthopanax chiisanensis and the mechanism of action.	2002 Nov 1	12392817
Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E2 production.	2005 Feb	15852488
Antifibrotic compounds from Liriodendron tulipifera attenuating HSC-T6 proliferation and TNF-α production in RAW264.7 cells.	2015	25747981

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 Class	Chemical Created by `admin` on `Sat Dec 16 05:30:24 GMT 2023` Edited by `admin` on `Sat Dec 16 05:30:24 GMT 2023`
Record UNII	9VCT11F572
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SESAMIN, (-)-

Common Name

English

1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN- 1,4-DIYL)BIS-, CIS-(-)-

Common Name

English

L-SESAMIN

Common Name

English

1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1R-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-

Common Name

English

1,3-BENZODIOXOLE, 5,5'-((1R,3AS,4R,6AS)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-

Common Name

English

SESAMIN, L-

Common Name

English

(-)-SESAMIN

Common Name

English

Code System Code Type Description

CAS

13079-95-3

Created by admin on Sat Dec 16 05:30:24 GMT 2023 , Edited by admin on Sat Dec 16 05:30:24 GMT 2023

PRIMARY

PUBCHEM

382073

Created by admin on Sat Dec 16 05:30:24 GMT 2023 , Edited by admin on Sat Dec 16 05:30:24 GMT 2023

PRIMARY

FDA UNII

9VCT11F572

Created by admin on Sat Dec 16 05:30:24 GMT 2023 , Edited by admin on Sat Dec 16 05:30:24 GMT 2023

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24556122 | https://www.ncbi.nlm.nih.gov/pubmed/21077998 | https://www.ncbi.nlm.nih.gov/pubmed/20614822

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24556122 | https://www.ncbi.nlm.nih.gov/pubmed/21077998 | https://www.ncbi.nlm.nih.gov/pubmed/20614822