lignans and sesamol

Sesame seeds perform many therapeutic functions against several health issues especially those related to bones because they possess a rich content of calcium, vitamins, proteins, oil, and carbohydrates. Using the PubMed, ScienceDirect, and Google Scholar databases, we performed a comprehensive search of the literature from 2013 to date on reports related to sesame seeds and their bioactive ingredients. Sesamin, sesamol, sesamolin, and sesamol are the major bioactive lignans found in sesame seeds. Our comprehensive review of the literature revealed the protective role of sesame seeds towards bone health in postmenopausal osteoporosis. It was observed that sesame seeds have a positive impact on postmenopausal women experiencing bone-related problems,

Topics: Benzodioxoles; Bone Density; Dioxoles; Female; Humans; Lignans; Postmenopause; Seeds; Sesamum

Inflammation is associated with the development and progression of a plethora of diseases including joint, metabolic, neurological, hepatic, and renal disorders. Sesamol, derived from the seeds of Sesamum indicum L., has received considerable attention due to its well-documented multipotent phytotherapeutic effects, including its anti-inflammatory and immunomodulatory properties. However, to date, no comprehensive review has been established to highlight or summarize the anti-inflammatory and immunomodulatory properties of sesamol. Herein, we aim to address this gap in the literature by presenting a thorough review encapsulating evidence surrounding the range of inflammatory mediators and cytokines shown to be targeted by sesamol in modulating its anti-inflammatory actions against a range of inflammatory disorders. Additionally, evidence highlighting the role that sesamol has in modulating components of adaptive immunity including cellular immune responses and Th1/Th2 balance is underscored. Moreover, the molecular mechanisms and the signaling pathways underlying such effects are also highlighted. Findings indicate that this seemingly potent lignan mediates its anti-inflammatory actions, at least in part, via suppression of various pro-inflammatory cytokines like IL-1β and TNFα, and downregulation of a multitude of signaling pathways including NF-κB and MAPK. In conclusion, we anticipate that sesamol may be employed in future therapeutic regimens to aid in more effective drug development to alleviate immune-related and inflammatory conditions.

Topics: Anti-Inflammatory Agents; Benzodioxoles; Cytokines; Lignans; Sesamum

Major lignans of sesame sesamin and sesamolin are benzodioxol--substituted furofurans. Sesamol, sesaminol, its epimers, and episesamin are transformation products found in processed products. Synthetic routes to all lignans are known but only sesamol is synthesized industrially. Biosynthesis of furofuran lignans begins with the dimerization of coniferyl alcohol, followed by the formation of dioxoles, oxidation, and glycosylation. Most genes of the lignan pathway in sesame have been identified but the inheritance of lignan content is poorly understood. Health-promoting properties make lignans attractive components of functional food. Lignans enhance the efficiency of insecticides and possess antifeedant activity, but their biological function in plants remains hypothetical. In this work, extensive literature including historical texts is reviewed, controversial issues are critically examined, and errors perpetuated in literature are corrected. The following aspects are covered: chemical properties and transformations of lignans; analysis, purification, and total synthesis; occurrence in

Topics: Benzodioxoles; Dioxoles; Furans; Lignans; Oxidation-Reduction; Phenols; Seeds; Sesamum

Although sesame seed oil contains high levels of unsaturated fatty acids and even a small amount of free fatty acids in its unrefined flavored form, it shows markedly greater stability than other dietary vegetable oils. The good stability of sesame seed oil against autoxidation has been ascribed not only to its inherent lignans and tocopherols but also to browning reaction products generated when sesame seeds are roasted. Also, there is a strong synergistic effect among these components. The lignans in sesame seed oil can be categorized into two types, i.e. inherent lignans (sesamin, sesamolin) and lignans mainly formed during the oil production process (sesamol, sesamolinol, etc.). The most abundant tocopherol in sesame seed oil is γ-tocopherol. This article reviews the antioxidant activities of lignans and tocopherols as well as the browning reaction and its products in sesame seed and/or its oil. It is concluded that the composition and structure of browning reaction products and their impacts on sesame ingredients need to be further studied to better explain the remaining mysteries of sesame oil.

Topics: Antioxidants; Benzodioxoles; Diet; Dioxoles; gamma-Tocopherol; Humans; Lignans; Phenols; Seeds; Sesame Oil; Sesamum

Topics: Benzodioxoles; Dioxoles; Humans; Lignans; Melanoma; Phenols

The progression of chronic kidney disease (CKD) increases the risks of cardiovascular morbidity and end-stage kidney disease. Indoxyl sulfate (IS), which is derived from dietary l-tryptophan by the action of bacterial l-tryptophan indole-lyase (TIL) in the gut, serves as a uremic toxin that exacerbates CKD-related kidney disorder. A mouse model previously showed that inhibition of TIL by 2-aza-l-tyrosine effectively reduced the plasma IS level, causing the recovery of renal damage. In this study, we found that (+)-sesamin and related lignans, which occur abundantly in sesame seeds, inhibit intestinal bacteria TILs. Kinetic studies revealed that (+)-sesamin and sesamol competitively inhibited Escherichia coli TIL (EcTIL) with K

Topics: Benzodioxoles; Dioxoles; Enzyme Inhibitors; Gastrointestinal Microbiome; Kinetics; Lignans; Molecular Docking Simulation; Phenols; Renal Insufficiency, Chronic; Sesamum; Tryptophanase

Non-alcoholic fatty liver disease (NAFLD) can be attributed to the imbalance between lipogenesis and lipidolysis in the liver. Sesame lignans (sesamin, sesamolin, and sesamol) are unique bioactive compounds responsible for the nutritional function of sesame oils. However, the preventive effects of three lignans on oxidative stress and lipid metabolism in steatosis HepG2 cells have not been compared. In this study, we investigated the role of sesamin, sesamolin, and sesamol on hepatic lipid accumulation and explored the underlying mechanism via a well-established cell model. The results showed that 3 μg/ml of lignans could decrease the TG/TC contents and alleviate cellular oxidative stress, with an order of the lipid-lowering effect as sesamol > sesamin > sesamolin. The lignan-activated AMPK and PPAR signaling pathways enhanced gene and protein expressions related to fatty acid oxidation, cholesterol efflux, and catabolism. Meanwhile, treatment of the steatosis HepG2 cells with sesamin, sesamolin, and sesamol reduced lipid synthesis and cholesterol uptake, thus lowering intracellular lipogenesis in the process of NAFLD. Our data suggested that sesame lignans can attenuate oxidative stress and regulate lipid metabolism in liver cells, which may be potential therapeutic agents for treating the NAFLD. PRACTICAL APPLICATIONS: The present work demonstrated that sesame lignans can be used for dietary supplements or functional additives with excellent lipid-lowering effects. Furthermore, this study supplied potential molecular mechanisms involved in NAFLD treatment process, and also provided nutritional guidelines for sesame oil evaluation and selection.

Topics: Benzodioxoles; Cholesterol; Dioxoles; Hep G2 Cells; Humans; Lignans; Lipid Metabolism; Non-alcoholic Fatty Liver Disease; Oxidative Stress; Phenols; Sesame Oil; Sesamum

Alzheimer's disease (AD) is a neurodegenerative disease, characterized by memory loss and cognitive deficits accompanied by neuronal damage and cholinergic disorders. Sesamol, a lignan component in sesame oil, has been proven to have neuroprotective effects. This research aimed to investigate the preventive effects of sesamol on scopolamine (SCOP)-induced cholinergic disorders in C57BL/6 mice. The mice were pretreated with sesamol (100 mg/kg/d, p.o.) for 30 days. Behavioral tests indicated that sesamol supplement prevented SCOP-induced cognitive deficits. Sesamol enhanced the expression of neurotrophic factors and postsynaptic density (PSD) in SCOP-treated mice, reversing neuronal damage and synaptic dysfunction. Importantly, sesamol could balance the cholinergic system by suppressing the AChE activity and increasing the ChAT activity and

Topics: Animals; Antioxidants; Cholinergic Agents; Cognition; Cognitive Dysfunction; Humans; Lignans; Maze Learning; Memory Disorders; Mice; Mice, Inbred C57BL; Nerve Growth Factors; Neuroblastoma; Neurodegenerative Diseases; Neuroinflammatory Diseases; Neuroprotective Agents; Oxidative Stress; Scopolamine; Sesame Oil

The effects of roasting and in vitro digestion on total phenolic content (TPC), total flavonoid content (TFC), phenolic profiles, and antioxidant activity of water-soluble extracts from six varieties of sesame were investigated in this study. Our results showed that the major phenolic compounds in raw, roasted and digested sesame were gallic acid (GA), protocatechuic acid (PA), 4-hydroxybenzoic acid (4 HBA), ferulic acid (FA) and quercetin (Quer). Roasting significantly increased the TPC, pinoresinol diglucoside (PD), sesamol, as well as the content of phenolic compounds (especially GA, PA, 4 HBA and Quer) in sesame, but kept or reduced the TFC, sesamin and sesamolin. After roasting, the antioxidant potency composite index (ACI) of six varieties of sesame was significantly increased by 29.8%-216.6%. Additionally, the ACI of gastric digestion was significantly higher than that of oral and intestinal digestion during the in vitro digestion of the roasted-sesame, except for the varieties of Ganzhi 9 and Ganzhi 17. This study showed that five phenolic compounds (GA, PA, 4 HBA, p-coumaric acid, Quer) and sesamol of the water-soluble extracts contributed to the antioxidant activities of the digestive products of sesame.

Topics: Anticarcinogenic Agents; Antioxidants; Benzodioxoles; Coumaric Acids; Digestion; Dioxoles; Flavonoids; Gallic Acid; Hydroxybenzoates; Lignans; Parabens; Phenol; Phenols; Plant Extracts; Principal Component Analysis; Propionates; Quercetin; Seeds; Sesamum

Alzheimer's disease (AD) is a devastating neurodegenerative disease characterized by β-amyloid (Aβ) plaques in the brain. At the present, there is no approved drug with a proven disease-modifying effect. Sesame seed (Sesame indicum) has long been known as a healthy food in Southeast Asian countries. Sesame lignans obtained from sesame seed possess antioxidant property that exhibit a variety of beneficial effects in various models. The objective of this study was to investigate the protective effects of sesame lignans including sesamin, sesamolin, and sesamol against Aβ toxicity in Caenorhabditis elegans (C. elegans) model of Aβ toxicity and to address whether these sesame lignans have a positive effect on lifespan extension. A transgenic C. elegans expressing human Aβ was used to investigate protective effects of sesame lignans against Aβ toxicity. Sesamin and sesamolin significantly alleviated Aβ-induced paralysis. The real-time PCR revealed that both sesamin and sesamolin did not affect the expression of Aβ transgene. However, we found that only sesamin inhibited Aβ oligomerization. These findings demonstrated that, among three sesame lignans tested, sesamin protected against Aβ toxicity by reducing toxic Aβ oligomers. Sesamin and sesamolin also significantly improved Aβ-induced defect in chemotaxis behavior and reversed the defect to normal. Moreover, sesamin prolonged median and mean lifespan of the wild type worm. On the other hand, sesamolin and sesamol failed to extend lifespan. These results offer valuable evidence for the future use of sesamin in the development of agents for the treatment of AD. It is also worth investigating the structure-activity relationship of lignan-related structures and their anti-Aβ toxicity activities in the future.

Topics: Amyloid beta-Peptides; Animals; Animals, Genetically Modified; Benzodioxoles; Caenorhabditis elegans; Chemotaxis; Dioxoles; Lignans; Longevity; Neurons; Paralysis; Phenols; Protein Multimerization; Transgenes

Graphene oxide was fabricated by a simple method and applied to magnetic solid-phase extraction. In a pretreatment procedure before the sesamol, sesamin and sesamolin in sesame oil were detected by high performance liquid chromatography. Several parameters affecting the extraction efficiency were investigated, including the type and volume of desorption solvent, desorption time and the amount of sorbent. Under the optimized conditions, the detection limits of sesamol, sesamin, and sesamolin were 0.05μg/g, 0.02μg/g, and 0.02μg/g, respectively. The limits of quantification were all 0.2μg/g. The average recoveries of sesamol, sesamin, and sesamolin were 84.55%, 85.47%, 86.83%, respectively and their relative standard deviations were 1.23%, 1.33%, and 0.84%, respectively.

Topics: Benzodioxoles; Chromatography, High Pressure Liquid; Dioxoles; Graphite; Lignans; Magnetic Phenomena; Phenols; Sesame Oil; Solid Phase Extraction

The role of inflammation and oxidative stress is critical during onset of metabolic disorders and this has been sufficiently established in literature. In the present study, we evaluated the effects of sesamol and sesamin, two important bioactive molecules present in sesame oil, on the generation of inflammatory and oxidative stress factors in LPS injected rats. Sesamol and sesamin lowered LPS induced expression of cPLA

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antioxidants; Arachidonate 5-Lipoxygenase; Benzodioxoles; Biomarkers; Dietary Supplements; Dioxoles; Glutathione Transferase; Hepatitis; Inflammation Mediators; Leukotriene Antagonists; Leukotrienes; Lignans; Lipid Peroxidation; Lipopolysaccharides; Liver; Male; Oxidative Stress; Phenols; Phospholipases A2, Cytosolic; Rats, Wistar; Receptors, Leukotriene B4; Sesame Oil

There is considerable interest in dietary lignans since they have been shown to have antioxidant, estrogenic and lipid-lowering activity in humans. In this study, the fluorescent excitation and emission spectra of seven lignans were characterized and their relative fluorescent intensities compared. The lignans were found to have similar excitation (286.6 ± 2.5 nm, X ± SD) and emission (320.1 ± 6.4 nm) maxima; however, their fluorescence intensities on a molar basis decreased in the following order: asarinin, sesamin, sesamolin, seco-isolariciresinol, seco-isolariciresinol diglucoside and matairesinol. Enterolactone, a mammalian lignan conversion product, and sesamol, an antioxidant found in sesame oil, also exhibited significant fluorescence excitation and emission intensities. A high-performance liquid chromatographic method using photodiode array (PDA) and fluorescent detection was developed for the analysis of the individual lignans. Analysis was performed on a reversed phase C-18 column with methanol-water (70:30, v/v) as the mobile phase. With fluorescent detection, the limits of quantitation (LOQ) was 0.1 ng or 2.82 nmol for sesamin and asarinin, 2.70 nmol for sesamolin, 2.76 nmol for seco-isolariciresinol, 1.45 nmol for seco-isolariciresinol diglucoside, 2.79 nmol for matairesinol and 0.5 ng or 1.67 nmol for enterolactone. With PDA detection, the LOQ was a 1000-fold less sensitive than with fluorescent detection.

Topics: Benzodioxoles; Chromatography, High Pressure Liquid; Dioxoles; Lignans; Phenols; Sensitivity and Specificity; Spectrometry, Fluorescence

Sesamin, sesamolin (lignans) and sesamol--from sesame seed (Sesamum indicum L.)--are known for their health promoting properties. We examined the inhibition effect of sesamol, a phenolic degradation product of sesamolin, on the key enzyme in melanin synthesis, viz. tyrosinase, in vitro. Sesamol inhibits both diphenolase and monophenolase activities with midpoint concentrations of 1.9 μM and 3.2 μM, respectively. It is a competitive inhibitor of diphenolase activity with a K(i) of 0.57 μM and a non-competitive inhibitor of monophenolase activity with a K(i) of 1.4 μM. Sesamol inhibits melanin synthesis in mouse melanoma B16F10 cells in a concentration dependant manner with 63% decrease in cells exposed to 100 μg/mL sesamol. Apoptosis is induced by sesamol, limiting proliferation. This study of the chemistry and biology of lignans, in relation to the mode of action of bioactive components, may open the door for drug applications targeting enzymes.

Topics: Agaricales; Animals; Apoptosis; Benzodioxoles; Catalytic Domain; Cell Line, Tumor; Cooking; Copper; Enzyme Inhibitors; Lignans; Melanins; Mice; Monophenol Monooxygenase; Oxidoreductases; Phenols; Protein Binding; Sesame Oil; Spectrum Analysis

Prevention of arterial thrombotic diseases has a high priority in developed countries. An inappropriate diet is known to enhance the risks for acute thrombotic events, and nutritional products experimentally shown to be antithrombotic, might contribute beneficial effects. The present study forms part of a series of investigations into the antithrombotic effect of various foods and vegetables. Roasted and crushed whole grains from six varieties of sesame seeds were added to the diet of mice. Antithrombotic activity was measured in the carotid artery in vivo, using a He-Ne laser-induced thrombosis technique after 12 weeks. Col/Chichibu/Maruteru-2/1995 and T016 varieties showed significant antithrombotic activity, whilst 00037803 was prothrombotic. The acute effects of purified ingredients, sesamin, sesamolin and sesamol, given orally or intra-arterially, were also examined after a single dose. The most effective ingredient was sesamol, followed by sesamolin and sesamin. Daily intake of specific antithrombotic sesame whole grains or purified active ingredients might help to prevent atherothrombotic diseases.

Topics: Administration, Oral; Animals; Benzodioxoles; Diet, High-Fat; Dioxoles; Disease Models, Animal; Edible Grain; Fibrinolytic Agents; Humans; Infusions, Intra-Arterial; Lasers; Lignans; Male; Mice; Mice, Inbred C57BL; Phenols; Plant Extracts; Sesamum; Thrombosis

Sesame lignans have antioxidative and anti-inflammatory properties. We focused on the effects of the lignans sesamin and sesamol on the expression of endothelial-leukocyte adhesion molecules in tumor necrosis factor-alpha (TNF-alpha)-treated human aortic endothelial cells (HAECs). When HAECs were pretreated with sesamin (10 or 100 microM), the TNF-alpha-induced expression of intercellular cell adhesion molecule-1 (ICAM-1) was significantly reduced (35 or 70% decrease, respectively) by Western blotting. Sesamol was less effective at inhibiting ICAM-1 expression (30% decrease at 100 microM). Sesamin and sesamol reduced the marked TNF-alpha-induced increase in human antigen R (HuR) translocation and the interaction between HuR and the 3'UTR of ICAM-1 mRNA. Both significantly reduced the binding of monocytes to TNF-alpha-stimulated HAECs. Sesamin significantly attenuated TNF-alpha-induced ICAM-1 expression and cell adhesion by downregulation of extracellular signal-regulated kinase 1/2 and p38. Furthermore, in vivo, sesamin attenuated intimal thickening and ICAM-1 expression seen in aortas of apolipoprotein-E-deficient mice. Taken together, these data suggest that sesamin inhibits TNF-alpha-induced extracellular signal-regulated kinase/p38 phosphorylation, nuclear translocation of NF-kappaB p65, cytoplasmic translocalization of HuR and thereby suppresses ICAM-1 expression, resulting in reduced adhesion of leukocytes. These results also suggest that sesamin may prevent the development of atherosclerosis and inflammatory responses.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antigens, Surface; Antioxidants; Aorta; Apolipoproteins E; Atherosclerosis; Benzodioxoles; Cell Line; Cells, Cultured; Dioxoles; ELAV Proteins; ELAV-Like Protein 1; Endothelium, Vascular; Gene Expression Regulation; Humans; Intercellular Adhesion Molecule-1; Lignans; Mice; Mice, Knockout; Monocytes; Phenols; Random Allocation; RNA-Binding Proteins; RNA, Messenger; RNA, Small Interfering; Signal Transduction; Tumor Necrosis Factor-alpha

The expression of oestrogen receptors (ERalpha and ERbeta) in the prostate and uterus tissues of Wistar rats supplied for 8 weeks with a diet rich in sesame (Sesamum indicum) pericarp (30 %) was monitored. Eight male rats, aged 6 weeks, were divided into a control group fed on a normal diet, and an experimental one, provided with the normal diet enriched with 30 % sesame pericarp. A similar experiment was performed with female rats. At the end of the experiment, the prostate and uterus tissues were surgically removed and kept at - 80 degrees C for up to 2 months. Western blotting and quantitative real-time PCR (qRT-PCR) methods were used in order to investigate the levels of receptor proteins and mRNA. Significant increase in the expression of ERbeta in prostate and uterus was evident in both methods, while the magnitude of the observed alteration depended on the applied method. No statistically significant change was observed in the expression of ERalpha in uterus. In prostate, although the increase was more evident when investigated by means of qRT-PCR, the difference in expression of ERalpha was not statistically significant. In both tissues, a shift of the ratio of ERalpha:ERbeta in favour of ERbeta was evident, indicating, according to existing literature, a beneficial effect of the diet provided upon the health status of the organisms. It is suggested that this effect is attributed to the lignans present in the pericarp which exert phyto-oestrogenic activity.

Topics: Animals; Benzodioxoles; Diet; Dioxoles; Estrogen Receptor alpha; Estrogen Receptor beta; Female; Lignans; Male; Phenols; Phytoestrogens; Prostate; Rats; Rats, Wistar; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sesamum; Uterus

Structured lipid (SL) was prepared from roasted sesame oil and caprylic acid (CA) by Rhizomucor miehei lipase-catalyzed acidolysis in a bench-scale continuous packed bed reactor. Total incorporation and acyl migration of CA in the SL were 42.5 and 3.1 mol %, respectively, and the half-life of the lipase was 19.2 days. The SL displayed different physical and chemical properties, less saturated dark brown color, lower viscosity, lower melting and crystallization temperature ranges, higher melting and crystallization enthalpies, higher smoke point, higher saponification value, and lower iodine value, in comparison to those of unmodified sesame oil. The oxidative stability of purified SL was lower than that of sesame oil. There were no differences in the contents of unsaponifiables including tocopherols and phytosterols. However, total sesame lignans content was decreased in SL due to the loss of sesamol when compared to sesame oil. Most of the 70 volatiles present in roasted sesame oil were removed from SL during short-path distillation of SL. These results indicate that the characteristics of SL are different from those of original sesame oil in several aspects except for the contents of tocopherols and phytosterols.

Topics: Benzodioxoles; Bioreactors; Caprylates; Crystallization; Drug Stability; Hot Temperature; Hydrogen-Ion Concentration; Lignans; Lipase; Lipids; Oxidation-Reduction; Phenols; Phytosterols; Rhizomucor; Sesame Oil; Thermodynamics; Tocopherols

The free radical scavenging capacity (RSC) of antioxidants from sesame cake extract was studied using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(*)()) on a kinetic model. Pure lignans and lignan glycosides isolated from methanolic extract by preparative HPLC were used in the study. To understand the kinetic behavior better and to determine the RSC of sesame antioxidants, the second-order rate constant (k(2)) was calculated for the quenching reaction with [DPPH(*)] radical. The k(2) values of the sesame antioxidants were compared with those of butylated hydroxytoluene and alpha-tocopherol. The k(2) values for sesamol, sesamol dimer, sesamin, sesamolin, sesaminol triglucoside, and sesaminol diglucoside were 4.00 x 10(-)(5), 0.50 x 10(-)(5), 0.36 x 10(-)(5), 0.13 x 10(-)(5), 0.33 x 10(-)(5), and 0.08 x 10(-)(5) microM(-)(1) s(-)(1), respectively.

Topics: Antioxidants; Benzodioxoles; Biphenyl Compounds; Dioxoles; Free Radical Scavengers; Free Radicals; Furans; Kinetics; Lignans; Phenols; Picrates; Plant Extracts; Sesamum

Sesame oil has been reported to contain sesamolin, sesamin and sesamol as contact allergens. A female patient had cheilitis due to sesame oil in a lipstick. She reacted to sesamolin and sesamin, but not to sesamol. We carried out analysis of the sesame oil by high performance liquid chromatography. We detected sesamolin and sesamin but not sesamol in sesame oil.

Topics: Adult; Benzodioxoles; Cheilitis; Chromatography, High Pressure Liquid; Dermatitis, Contact; Dioxoles; Female; Humans; Lignans; Patch Tests; Phenols; Plant Oils; Sesame Oil