Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H18O6 |
Molecular Weight | 354.3533 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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-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
DescriptionSources: https://examine.com/supplements/sesamin/ | https://www.ncbi.nlm.nih.gov/pubmed/1943494https://www.google.com/patents/US4427694 | https://books.google.ru/books?id=VCITWqQS_6MC&pg=PA493&lpg=PA493&dq=racemic+sesamin retrieved from Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants, Second Edition 2nd Edition by Herbert Baxter (Editor), J.B. Harborne (Editor), Gerald P. Moss (Editor), p.493 | https://examine.com/supplements/sesamin/
Sources: https://examine.com/supplements/sesamin/ | https://www.ncbi.nlm.nih.gov/pubmed/1943494https://www.google.com/patents/US4427694 | https://books.google.ru/books?id=VCITWqQS_6MC&pg=PA493&lpg=PA493&dq=racemic+sesamin retrieved from Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants, Second Edition 2nd Edition by Herbert Baxter (Editor), J.B. Harborne (Editor), Gerald P. Moss (Editor), p.493 | https://examine.com/supplements/sesamin/
Sesamin is a naturally occurring compound found in sesame oil and in the bark and fruit of certain plant species. SESAMIN, (±)- is a racemic dl-form. The dl-form is also known as fagarol, and may be isolated from the bark of various fagara species. 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. 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 athletes 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 desaturases in polyunsaturated fatty acid biosynthesis. Sesamin inhibits particular CYP3A enzymes that are 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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5727 |
155.0 µM [Ki] | ||
Target ID: CHEMBL612877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26411017 |
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Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15285849 |
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Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15285849 |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15285849 |
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Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25987037 |
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Target ID: CHEMBL5727 |
155.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20118549/ |
weak | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20118549/ |
weak | |||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20118549/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20118549/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Differential in vitro anti-HIV activity of natural lignans. | 1990 Nov-Dec |
|
Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress. | 2008 Oct-Dec |
|
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats. | 2010 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://examine.com/supplements/sesamin/
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/
There are limited human studies on sesamin, but it appears that 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; this indirect antioxidative effect may be the most practical reason to supplement sesamin.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20306475
When HAECs were pretreated with sesamin (10 or 100 uM), the TNF-alpha-induced expression of intercellular cell adhesion molecule-1 (ICAM-1) was significantly reduced (35 or 70% decrease, respectively) by Western blotting.
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SUBSTANCE RECORD