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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H18O6
Molecular Weight 354.3541
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SESAMIN

SMILES

c1cc2c(cc1[C@]3([H])[C@@]4([H])CO[C@]([H])(c5ccc6c(c5)OCO6)[C@@]4([H])CO3)OCO2

InChI

InChIKey=PEYUIKBAABKQKQ-AFHBHXEDSA-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+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H18O6
Molecular Weight 354.3541
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Sesamin is the most prominent lignan compound found in sesame seeds, one of the two highest sources of lignans in the human diet (the other being flax). Sesamin is catered to be a nutritional supplement that confers antioxidant and antiinflammatory effects (if touting its health properties) or possibly being an estrogen receptor modulator and fat burner (if targeting atheltes or persons wishing to lose weight). Sesamin has a few mechanisms, and when looking at it holistically it can be summed up as a fatty acid metabolism modifier. It appears to inhibit an enzyme known as delta-5-desaturase (Δ5-desaturase) which is a rate-limiting enzyme in fatty acid metabolism; inhibiting this enzyme results in lower levels of both eicosapentaenoic acid (EPA, one of the two fish oil fatty acids) as well as arachidonic acid, and this mechanism appears to be relevant following oral ingestion. The other main mechanism is inhibiting a process known as Tocopherol-ω-hydroxylation, which is the rate limiting step in the metabolism of Vitamin E; by inhibiting this enzyme, sesamin causes a relative increase of vitamin E in the body but particularly those of the gamma subset (γ-tocopherol and γ-tocotrienol) and this mechanism has also been confirmed to be active following oral ingestion. Sesamin is a potent and specific inhibitor of delta 5 desaturase in polyunsaturated fatty acid biosynthesis. Sesamin inhibits a particular CYP3A enzymes that is involved in vitamin E metabolism, where the enzyme initially ω-hydroxylates vitamin E (required step) and then the rest of vitamin E is subject to fat oxidation. By inhibiting this step, sesamin causes an increase in circulating and organ concentrations of vitamin E. Sesamin is thought to have PPARα activating potential in the liver, but it is uncertain how much practical relevance this has in humans due to this being a mechanism that differs between species.

CNS Activity

Curator's Comment:: Sesamin, either as the d-form or the dl-form, has now been found to possess psychotropic activity, i.e., administration of appropriate dosages to a human or animal subject elicits a psychotropic response.

Approval Year

TargetsConditions
OverviewDrug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
major
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Differential in vitro anti-HIV activity of natural lignans.
1990 Nov-Dec
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats.
2010 Jan 5
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: In humans oral ingestion of around 100-150mg of sesamin is sufficient to raise bodily sesamin stores to the level where it can preserve Vitamin E in the body. https://examine.com/supplements/sesamin/
Mice: Two weeks after CFA administration, mice received an intragastric administration of vehicle or sesamin (80 mg/kg) once a day for 1 week (from day 15 to day 21) after CFA injection.
Route of Administration: Other
Sesamin dose-dependently (1, 10 and 50 uM) reduced the cell viability and increased LDH release and apoptosis (TUNEL assay) in human breast cancer mcf-7 cells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:59:41 UTC 2021
Edited
by admin
on Sat Jun 26 05:59:41 UTC 2021
Record UNII
S7946O4P76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SESAMIN
MI  
Common Name English
FAGAROL
Common Name English
D-(+)-SESAMIN
Common Name English
D-SESAMIN
Common Name English
5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-1,3-BENZODIOXOLE
Systematic Name English
1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1S-(1.ALPHA.,3A .ALPHA.,4.ALPHA.,6A .ALPHA.))-
Common Name English
SEZAMIN
Common Name English
(+)-SESAMIN
Common Name English
SESAMIN, (+)-
Common Name English
SESAMIN D-FORM [MI]
Common Name English
1H,3H-FURO(3,4-C)FURAN, TETRAHYDRO-1,4-BIS(3,4-(METHYLENEDIOXY)PHENYL)-, (1S,3AR,4S,6AR)-
Common Name English
TETRAHYDRO-1,4-BIS(3,4-(METHYLENEDIOXY)PHENYL)-1H,3H-FURO(3,4-C)FURAN
Systematic Name English
NSC-36403
Code English
SESAMIN [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 298400
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
Code System Code Type Description
PUBCHEM
72307
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
CAS
7076-24-6
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
MESH
C054125
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
WIKIPEDIA
SESAMIN
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
EVMPD
SUB120775
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
CAS
607-80-7
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
MERCK INDEX
M9879
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY Merck Index
MERCK INDEX
M9879
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY Merck Index
FDA UNII
S7946O4P76
Created by admin on Sat Jun 26 05:59:41 UTC 2021 , Edited by admin on Sat Jun 26 05:59:41 UTC 2021
PRIMARY
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