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Product name: Sesamin
Synonym name: Asarinin; Episesamin; Fagarol; Sezamin
Catalogue No.: BP1296
Cas No.: 607-80-7
Formula: C20H18O6
Mol Weight: 354.358
Botanical Source: Sesamum indicum L.
Physical Description:
Type of Compound: Lignans
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of Sesamin
NMR of Sesamin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
55.3800
2.5422
2.5422
.0026
7.0557
11.6969
High
89.8382
3.7741
Yes
Yes
Yes
No
Yes
No
1.5
No
Yes
No
Yes
Sesamin, CAS number 607-80-7, is a natural lignan compound mainly found in sesame oil. As one of the main active ingredients in sesame oil, sesamin has attracted significant attention in both traditional medicine and modern nutrition. In recent years, with the deepening of pharmacological research on natural products, sesaminin has become a hot topic in pharmacological research due to its remarkable biological activity, especially its potential in antioxidant, anti-inflammatory, and neuroprotective properties. Sesaminin is not only an effective and selective delta-5 desaturase inhibitor in polyunsaturated fatty acid biosynthesis, but also demonstrates significant protective effects against neurological diseases such as cerebral ischemia. This paper will systematically review the chemical structure and physicochemical properties of sesagin, plant origin and extraction methods, pharmacological activity and mechanism of action, efficacy evaluation, pharmacokinetic characteristics, and clinical application prospects, aiming to provide a theoretical basis and research direction for the drug development of this natural product.
Sesamin, chemically named 3,4-methylenedioxy-1,4-diphenylbutane, is a typical lignan compound. Its molecular formula is C20H18O6, and its molecular weight is 354.3580. Sesamin's structure contains two aromatic rings, connected by methylene dioxy bridges, forming a stable double-ring structure that imparts good chemical stability and biological activity. Its LogP value was 2.5422, indicating that sesaminin has moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. The topological pole surface area (TPSA) is 55.38 Ų, indicating suitability for crossing the blood-brain barrier (BBB), a characteristic closely related to its neuroprotective effects. Sesain has low water solubility (0.0026 mg/mL), limiting its oral bioavailability, but its high lipid solubility benefits its distribution in lipid environments. The hERG channel inhibition test results were negative, indicating that sesaminin has low potential toxicity to cardiac ion channels. The Ames test result was 1.5, indicating a low genotoxicity risk.
Sesamus lin is mainly found in sesame seeds (Sesamum indicum L.) and its oils, and is a lignan component with a high content in sesame oil. The sesamin content is greatly influenced by the variety, cultivation environment, and processing technology. In the traditional extraction process, sesamin, as a fat-soluble component, is retained in the oil.
Common methods for extracting sesaminin include solvent extraction, supercritical CO2 extraction, and column chromatography purification. Solvent extraction often uses organic solvents such as ethanol, methanol, or ethyl acetate, combined with ultrasound-assisted extraction technology to improve extraction efficiency and purity. Supercritical CO2 extraction is gradually becoming a mainstream technology due to its environmental friendliness, residue-free nature, and strong selectivity. After extraction, purification is performed by silica gel column chromatography or high-performance liquid chromatography (HPLC) to obtain high-purity sesamin.
Research on the pharmacological activity of sesaminin covers antioxidant, anti-inflammatory, neuroprotection, anti-tumor, lipid-regulating, and blood pressure lowering among multiple aspects.
Sesamin, as a natural antioxidant, can effectively eliminate free radicals and reduce oxidative stress damage. It enhances the cell's antioxidant defense by activating intracellular antioxidant enzyme systems such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1). Additionally, sesamin can upregulate the expression of hemoglobin oxygenase 1 (HMOX1), exerting a protective effect on cells.
Cerebral ischemia and its reperfusion injury are important pathological processes in neurological diseases. Sesaminin regulates fatty acid metabolism by inhibiting delta-5 desaturase activity, reducing lipid peroxidation in nerve cell membranes, and protecting neurons from oxidative damage. It also activates the nuclear factor 2-associated factor 2 (NFE2L2/NRF2) signaling pathway, inducing antioxidant gene expression, reducing oxidative stress and inflammatory responses caused by cerebral ischemia, and significantly improving neurological deficits.
Sesaminin can inhibit the expression and release of various pro-inflammatory factors, such as tumor necrosis factor α (TNF-α), interleukin-1β (IL-1β), and cyclooxygenase-2 (COX-2), thereby reducing inflammatory responses. Its anti-inflammatory effect partly depends on inhibition of the NF-κB signaling pathway, blocking the inflammatory cascade.
Sesamin also exhibits multiple biological activities, including regulating blood lipids, lowering blood pressure, anti-tumor, and anti-osteoporosis. In lipid metabolism, sesamin regulates polyunsaturated fatty acid synthesis by inhibiting delta-5 desaturation, improving dyslipidemia. Some studies have shown that sesaminin can inhibit proliferation and induce apoptosis in certain cancer cells.
The multiple pharmacological effects of sesalamin mainly depend on its regulation of intracellular signaling pathways and key enzymes.
Sesaminin activates NFE2L2/NRF2 transcription factors, promoting the expression of downstream antioxidant enzyme genes (such as SOD1, SOD2, CAT, GPX1, HMOX1), enhancing cells' ability to scavenge reactive oxygen species (ROS) and reducing oxidative damage. NRF2, as a core regulator of cellular antioxidant stress, has its activation as a key step in sesamin's antioxidant protective effects.
Sesamin, as an effective and selective inhibitor of delta-5 desaturase, blocks the biosynthesis pathway of polyunsaturated fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), affecting lipid metabolic balance. This regulation helps reduce the production of inflammatory mediators and improves pathological conditions related to metabolic syndrome.
In cerebral ischemia models, sesamin protects neuronal structure and function by reducing lipid peroxidation and inflammatory responses. At the same time, sesagin's high permeability into the blood-brain barrier ensures its effective concentration within the central nervous system, enhancing its neuroprotective effect.
Sesaminin reduces the expression of pro-inflammatory factors by inhibiting the NF-κB signaling pathway, thereby alleviating inflammatory responses. In addition, its regulation of the MAPK pathway also contributes to the realization of anti-inflammatory effects.
Sesaminin has relatively ideal druggability parameters. Its molecular weight of 354.3580 complies with the Lipinski rule, and a LogP value of 2.54 indicates moderate lipid solubility, which facilitates cell membrane penetration and oral absorption. The TPSA is 55.38 Ų, supporting its crossing of the blood-brain barrier and meeting its neuroprotective requirements. Low water solubility (0.0026 mg/mL) is a limiting factor for oral bioavailability and needs to be improved through formulation optimization.
Sesaminin does not inhibit hERG channels, indicating a lower risk of cardiotoxicity. The Ames test result was 1.5, indicating low genotoxicity risk and good safety.
Pharmacokinetic studies show that sesaginoids are absorbed orally quickly, have a moderate plasma half-life, and can effectively distribute in brain tissue. Its main metabolic pathways include oxidation and binding reactions in the liver, and the metabolites have certain biological activity. Future studies are needed to systematically study its in vivo metabolic kinetics and drug interactions.
Sesamin is a safe and biologically active natural product with broad clinical application prospects. Its potential therapeutic value in cerebral ischemia, neurodegenerative diseases, metabolic syndrome, and chronic inflammatory diseases is receiving increasing attention.
Future research should focus on:
In summary, sesamin is a multi-target, multifunctional natural lignan compound with potential as a novel neuroprotective agent and metabolic regulator.
Sesamin, as an important active ingredient in sesame oil, demonstrates significant antioxidant, neuroprotective, and anti-inflammatory multiple pharmacological activities due to its unique chemical structure and excellent physicochemical properties. By regulating the NFE2L2/NRF2 antioxidant signaling pathway and delta-5 desaturase activity, it exerts multi-layered biological effects, especially showing good therapeutic potential in neurological diseases such as cerebral ischemia. Druggability evaluations show that sesaminin has good safety and blood-brain barrier penetration, but its insufficient water solubility limits its clinical application. In the future, through formulation optimization and in-depth mechanistic research, sesamin is expected to become an important candidate molecule for natural product drug development, providing new strategies and ideas for the treatment of related diseases.
Shenshuai
Wenjing
Hedandan
