Sesamin

Description

Sesamin (607-80-7) is a natural product derived from sesame seeds with anticancer1, antioxidant2, anti-inflammatory/immunomodulatory3, and antidiabetic4,5 effects. It also displayed effects on cholesterol and fatty acid metabolism.6 Sesamin was recently found to inhibit bacterial L-tryptophan indole lyase (Ki = 7 μM).7 This enzyme reacts with dietary tryptophan to produce the uremic toxin indoxyl sulfate which exacerbates chronic kidney disease.

Chemical Properties

White powder

Uses

A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expr ession of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level.

Uses

Sesamin has been used:

• as a lignan to study its effects on the osteoblastic differentiation of rat bone marrow stromal cells (BMSCs)
• as a standard for the isolation of sesamin from sesame oil
• as an enterolignan to study its effects on the proliferation of estrogen-receptor (ER)-positive human breast cancer MCF-7 cells

Definition

ChEBI: A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR

General Description

Sesamin is a fat-soluble furfuran lignan present in Sesamum indicumL seeds.

Biochem/physiol Actions

Non-competitive Δ5-desaturase inhibitor.

Synthesis

Measure 1L of sesame oil foot (965.8g), add 4L of anhydrous ethanol, stirring at 30 for 5h, static stratification, take the upper layer of clear liquid, rotary evaporation to get sesquiterpene enriched material; to sesquiterpene enriched material to add anhydrous methanol, sesquiterpene enriched material with anhydrous methanol material-liquid ratio of 1:4 (kg/L), at 55 under the extraction of 3h, get the extract; to the extraction of the liquid to add activated carbon. Activated carbon added to the extraction solution, the amount of 1% of the mass of the extraction solution, stirring for 0.5h, and then filtered to obtain the sesquiterpene extract; the sesquiterpene extract slowly cooled down to -10 , so that the sesquiterpene crystallization, crystallization of 2h, filtration of sesquiterpene crude; to add petroleum ether to sesquiterpene crude, sesquiterpene crude and petroleum ether material-liquid ratio of 1:1 (kg/L), 35 , closed mixing for 0.5h, filtration Sesquiterpene crude product; sesquiterpene crude product dissolved in anhydrous ethanol, sesquiterpene crude product and anhydrous ethanol material-liquid ratio of 1:30 (kg / L), at -5 under the crystallization and purification, the time to maintain 3 hours, under this condition after two times crystallization, vacuum drying to obtain sesquiterpene products 2.16 g, sesquiterpene extraction rate of 89.1%, the purity of the resulting sesquiterpene products is 92.1%.

References

[1] AMIN F. MAJDALAWIEH  Gheyath K N  Mariam Massri. A comprehensive review on the anti-cancer properties and mechanisms of action of sesamin, a lignan in sesame seeds (Sesamum indicum)[J]. European journal of pharmacology, 2017, 815: Pages 512-521. DOI:10.1016/j.ejphar.2017.10.020
[2] KISO Y. Antioxidative roles of sesamin, a functional lignan in sesame seed, and it’s effect on lipid- and alcohol-metabolism in the liver: A DNA microarray study[J]. BioFactors, 2008, 21 1-4: 191-196. DOI:10.1002/biof.552210139
[3] AMIN F MAJDALAWIEH. Immunomodulatory and anti-inflammatory effects of sesamin: mechanisms of action and future directions.[J]. Critical reviews in food science and nutrition, 2022, 62 18: 5081-5112. DOI:10.1080/10408398.2021.1881438
[4] MAJID MOHAMMAD SHAHI. Effect of Sesamin Supplementation on Glycemic Status, Inflammatory Markers, and Adiponectin Levels in Patients with Type 2 Diabetes Mellitus.[J]. Journal of Dietary Supplements, 2017, 14 1: 65-75. DOI:10.1080/19390211.2016.1204404
[5] YAGHOOB FARBOOD . Sesamin: A promising protective agent against diabetes-associated cognitive decline in rats[J]. Life sciences, 2019, 230: Pages 169-177. DOI:10.1016/j.lfs.2019.05.071
[6] AMIN F. MAJDALAWIEH  Sarah M Y  Sarah Dalibalta. Effects of sesamin on fatty acid and cholesterol metabolism, macrophage cholesterol homeostasis and serum lipid profile: A comprehensive review[J]. European journal of pharmacology, 2020, 885: Article 173417. DOI:10.1016/j.ejphar.2020.173417
[7] DAIKI OIKAWA . (+)-Sesamin, a sesame lignan, is a potent inhibitor of gut bacterial tryptophan indole-lyase that is a key enzyme in chronic kidney disease pathogenesis[J]. Biochemical and biophysical research communications, 2022, 590: Pages 158-162. DOI:10.1016/j.bbrc.2021.12.088