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
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
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 |
DescriptionSources: https://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/https://examine.com/supplements/sesamin/ | https://www.ncbi.nlm.nih.gov/pubmed/1943494
Sources: https://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/https://examine.com/supplements/sesamin/ | https://www.ncbi.nlm.nih.gov/pubmed/1943494
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
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 |
|||
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 |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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 |
---|---|---|
[Synthesis of DL-asarinin and DL-sesamin]. | 1957 Jan |
|
Differential in vitro anti-HIV activity of natural lignans. | 1990 Nov-Dec |
|
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides. | 2003 Apr |
|
Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes. | 2003 Dec |
|
Antifungal constituents of Melicope borbonica. | 2004 Jul |
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Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats. | 2005 Jan |
|
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 |
|
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system. | 2012 |
|
Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway. | 2014 Jan 13 |
|
Effect of sesamin on apoptosis and cell cycle arrest in human breast cancer mcf-7 cells. | 2015 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25822813
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25987037
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
Edited
Thu Jul 06 03:36:26 UTC 2023
by
admin
on
Thu Jul 06 03:36:26 UTC 2023
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Record UNII |
S7946O4P76
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
298400
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72307
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S7946O4P76
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2593413
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7076-24-6
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C054125
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SESAMIN
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SUB120775
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100000144024
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M9879
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M9879
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36403
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DTXSID301030528
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66470
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S7946O4P76
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Natural antioxidant found in cultivated sesame oil.
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