Article

Effect of Sesame Seeds Rich in Sesamin and Sesamolin on Fatty Acid Oxidation in Rat Liver

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Abstract

Activities of enzymes involved in hepatic fatty acid oxidation and synthesis among rats fed sesame (Sesamum indicum L.) differing in lignan content (sesamin and sesamolin) were compared. Sesame seeds rich in lignans from two lines, 0730 and 0732, lines established in this laborary, and those from a conventional cultivar (Masekin) were employed. Seeds from the 0730 and 0732 lines contained sesamin and sesamolin at amounts twice those from Masekin. Sesame seeds were added at levels of 200 g/kg to the experimental diets. Sesame increased both the hepatic mitochondrial and the peroxisomal fatty acid oxidation rate. Increases were greater with sesame rich in lignans than with Maskin. Noticeably, peroxisomal activity levels were >3 times higher in rats fed diets containing sesame seeds from the 0730 and 0732 lines than in those fed a control diet without sesame. The diet containing Masekin seed caused only a 50% increase in the value, however. Diets containing seeds from the 0730 and 0732 lines, compared to the control and Masekin diets, also significantly increased the activity of hepatic fatty acid oxidation enzymes including acyl-CoA oxidase, carnitine palmitoyltranferase, 3-hydroxyacyl-CoA dehydrogenase, and 3-ketoacyl-CoA thiolase. In contrast, diets containing sesame lowered the activity of enzymes involved in fatty acid synthesis including fatty acid synthase, glucose-6-phosphate dehydrogenase, ATP-citrate lyase, and pyruvate kinase. No significant differences in enzyme activities were, however, seen among diets containing sesame from Masekin cultivar and lines 0730 and 0732. Serum triacylglycerol concentrations were lower in rats fed diets containing sesame from lines 0730 and 0732 than in those fed the control or Masekin diet. It is apparent that sesame rich in lignans more profoundly affects hepatic fatty acid oxidation and serum triacylglycerol levels. Therefore, consumption of sesame rich in lignans results in physiological activity to alter lipid metabolism in a potentially beneficial manner.

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... Dietary fat is deemed to play an important role in modulating risk factors for cardiovascular diseases (Hunter et al., 2010). As reported previously, replacing saturated fat with polyunsaturated fat has been found to obviate coronary events in animals and humans (Hegsted et al., 1993;Oyinloye et al., 2016;Sirato-Yasumoto et al., 2001). However, excessive consumption of unsaturated fatty acids leads to higher peroxidation in lipoproteins (Hegsted et al., 1993). ...
... The significant reduction in the TG concentration was more evident in all the studied organs compared with the plasma as there was about 8-fold reduction in the brain and 5-fold reduction in the liver, heart and kidney compared with only about 2-fold reduction in the plasma. The observed outcomes are consistent with the reduced levels of TC, TG and LDL-cholesterol levels associated with SI administration in cadmiuminduced oxidative stress in Wistar strain rats reported by Oyinloye et al. (2016), and that of Sirato-Yasumoto et al. (2001) who reported that sesame rich in lignans profoundly affects hepatic fatty acid oxidation and lowered serum triacylglycerol levels. The observed decrease in TG concentration in the SI-treated rats compared with that of the untreated rats serves as an indicator of the hypolipidemic potency of SI, and thus has the potential of being preferred as sole usage or as an adjuvant therapeutic remedy for hyperlipidemia-related disorders compared with commonly employed hypolipidemic drugs. ...
... Moreover, as reported previously, sesame lignans reduce serum and liver cholesterol concentrations by inhibiting the intestinal absorption of cholesterol and reducing the activity of acyl-CoA cholesterol acyl transferase and 3-hydroxy-3-methyl glutaryl CoA reductase (Afroz et al., 2019;Andargie et al., 2021;Kumar & Singh, 2015;Wu et al., 2019). Furthermore, the observed hypotriglyceridemic effect of SI seed supplementation could be attributed to the presence of sesamol, one of the bioactive constituents that has been previously reported to inhibit the intestinal absorption of triglycerides and promote cholesterol efflux from the blood when administered at a dosage of 50 mg/kg and 100 mg/kg on hyperlipidemia model mice, thus attenuating hypercholesterolemia and associated disorders (Kumar et al., 2013;Sirato-Yasumoto et al., 2001). Another plausible mechanism for the observed lipid-lowering effect of SI may be due to the suppression of the expression of the lipogenesis-related gene -sterol regulatory elementbinding protein-1 (SREBP1) (a key transcription factor involved in the biosynthesis of cholesterol and fatty acids) at the mRNA level or by the upregulation of the low density lipoprotein (LDL) receptor and the expression of cholesterol-7α-hydroxylase gene, the rate-limiting enzyme in the conversion of cholesterol to bile acids for excretion. ...
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Cardiovascular diseases and metabolic complications caused by hyperlipidemia are the leading cause of death globally. In this study, the hypolipidemic potency of Sesamum indicum (SI) seeds was investigated. Of the thirty-five (35) male rats used in the study, five (5) were randomly selected for baseline measurements and thirty (30) were fed high fat diet (HFD) for four (4) weeks before randomly assignment into three (3) groups. The experimental group was treated with 50% SI seed, the positive control group was given a hypolipidemic drug, atorvastatin (5 mg/kg/day) while the untreated group served as the negative control. With SI administration, the dyslipidemia induced by the HFD consumption in the plasma and the investigated body organs was reversed to a comparable degree with that of atorvastatin treatment. Taken together, this study demonstrates the hypolipidemic potency of SI in ameliorating hyperlipidemia and its associated complications, facilitated by the inhibition of HMG-CoA reductase activity.
... In particular, sesamin is believed to increase both hepatic peroxisomal and mitochondrial fatty acid oxidation rates, with the increases being greater for the former than for the latter, as evident from myriad of studies. In an in vivo study, Sirato-Yasumoto and colleagues examined the effects of three sesame lines on fatty acid oxidation rates in male Sprague-Dawley rats (Sirato-Yasumoto et al., 2001). The three sesame lines are conventional cultivar (Masekin) and two lines (0730 and 0732) that were established by the researchers. ...
... Results indicated a significant increase after 16 days in both hepatic peroxisomal and mitochondrial fatty acid oxidation rates in rats fed sesame seeds rich in lignans (i.e. the 0730 and 0732 lines) than in those kept at a Masekin diet. Specifically, mitochondrial fatty acid oxidation rates increased by 40, 80, and 60% with Masekin, 0730 line, and 0732 line, respectively (Sirato-Yasumoto et al., 2001). Increases in peroxisomal fatty acid oxidation rates were even more pronounced with sesame seeds rich in lignans, whereby peroxisomal activity increased by 60, 400, and 500% with Masekin, 0730 line, and 0732 line, respectively (Sirato-Yasumoto et al., 2001). ...
... Specifically, mitochondrial fatty acid oxidation rates increased by 40, 80, and 60% with Masekin, 0730 line, and 0732 line, respectively (Sirato-Yasumoto et al., 2001). Increases in peroxisomal fatty acid oxidation rates were even more pronounced with sesame seeds rich in lignans, whereby peroxisomal activity increased by 60, 400, and 500% with Masekin, 0730 line, and 0732 line, respectively (Sirato-Yasumoto et al., 2001). Further analysis also revealed a significant increase in the activity of hepatic fatty acid oxidation enzymes, including acyl-CoA oxidase (ACOX), carnitine palmitoyltransferase (CPT), 3-hydroxyacyl-CoA dehydrogenase (HADH), and 3-ketoacyl-CoA thiolase (KAT), which further complements and confirms the effect of sesamin on fatty acid oxidation rates. ...
Article
Sesamin is the major lignan constituent derived from Sesamum indicum seeds and sesame oil. Various studies have reported that sesamin possesses potent lipid-lowering properties. The lipid-lowering effects of sesamin have been mainly attributed to its ability in affecting key events in fatty acid and cholesterol metabolism and in lowering atherogenesis-triggering LDL, VLDL and TG levels, as well as in increasing atheroprotective HDL levels. In this review, we provide a comprehensive summary of the reported anti-hyperlipidemic effects of sesamin, presented both in vitro and in vivo. The molecular anti-hyperlipidemic properties of sesamin that underlie its well-documented anti-atherogenic effects are thoroughly discussed and analyzed. Studies focusing on the ability of sesamin to inhibit fatty acid synthesis, induce fatty acid oxidation, inhibit cholesterol synthesis and absorption and maintain macrophage cholesterol homeostasis are outlined. The effects of sesamin on circulating serum and liver lipid levels are also highlighted. Moreover, the anti-hyperlipidemic effects of sesamin are compared to those of other important sesame lignans like sesamolin and episesamin. Findings reveal that sesamin mainly exerts its anti-hyperlipidemic effects by targeting Δ5 desaturase, HMGCR, ABCA1 and ABCG1 through PPARα, PPARγ, LXRα, and SREBP signaling pathways. Overall, the amount of evidence supporting the anti-hyperlipidemic potential of sesamin in vitro and in vivo is compelling. A thorough understanding of the mechanisms underlying the anti-hyperlipidemic properties of sesamin is imperative for the possible employment of sesamin as an anti-hyperlipidemic and anti-atherogenic agent with minimal side effects.
... [75,76] Pesticide Sesquiterpene has both fungicide and insecticide properties and can be used as a synergist for pyrethroid insecticides. [77,78] Cosmetics ...
... Sesamin has both fungicide and insecticide properties and can be used as a synergist for pyrethroid insecticides [78]. This property has been successfully applied to children's hair to prevent lice infestation. ...
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Sesame (Sesamum indicum L.), of the Pedaliaceae family, is one of the first oil crops used in humans. It is widely grown and has a mellow flavor and high nutritional value, making it very popular in the diet. Sesame seeds are rich in protein and lipids and have many health benefits. A number of in vitro and in vivo studies and clinical trials have found sesame seeds to be rich in lignan-like active ingredients. They have antioxidant, cholesterol reduction, blood lipid regulation, liver and kidney protection, cardiovascular system protection, anti-inflammatory, anti-tumor, and other effects, which have great benefits to human health. In addition, the aqueous extract of sesame has been shown to be safe for animals. As an important medicinal and edible homologous food, sesame is used in various aspects of daily life such as food, feed, and cosmetics. The health food applications of sesame are increasing. This paper reviews the progress of research on the nutritional value, chemical composition, pharmacological effects, and processing uses of sesame to support the further development of more functionalities of sesame.
... Sesamin is mainly present in sesame seeds and preclinical studies have reported metabolic properties in liver pathologies by preventing from ACC- [132] and SREBP-1-mediated fatty acid synthesis [133], while enhances FAO mediated by CPT1 or 3-hydroxyacyl-coA dehydrogenase [132]. ...
... Sesamin is mainly present in sesame seeds and preclinical studies have reported metabolic properties in liver pathologies by preventing from ACC- [132] and SREBP-1-mediated fatty acid synthesis [133], while enhances FAO mediated by CPT1 or 3-hydroxyacyl-coA dehydrogenase [132]. ...
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Current food tendencies, suboptimal dietary habits and a sedentary lifestyle are spreading metabolic disorders worldwide. Consequently, the prevalence of liver pathologies is increasing, as it is the main metabolic organ in the body. Chronic liver diseases, with non-alcoholic fatty liver disease (NAFLD) as the main cause, have an alarming prevalence of around 25% worldwide. Otherwise, the consumption of certain drugs leads to an acute liver failure (ALF), with drug-induced liver injury (DILI) as its main cause, or alcoholic liver disease (ALD). Although programs carried out by authorities are focused on improving dietary habits and lifestyle, the long-term compliance of the patient makes them difficult to follow. Thus, the supplementation with certain substances may represent a more easy-to-follow approach for patients. In this context, the consumption of polyphenol-rich food represents an attractive alternative as these compounds have been characterized to be effective in ameliorating liver pathologies. Despite of their structural diversity, certain similar characteristics allow to classify polyphenols in 5 groups: stilbenes, flavonoids, phenolic acids, lignans and curcuminoids. Herein, we have identified the most relevant compounds in each group and characterized their main sources. By this, authorities should encourage the consumption of polyphenol-rich products, as most of them are available in quotidian life, which might reduce the socioeconomical burden of liver diseases.
... Sesame lignans have antioxidant and tocopherol-sparing activities [59][60][61][62]. They are reported to reduce cholesterol level [48,50,63] and exhibit antihypertensive [64] and anti-inflammatory activities [65] as well as affect lipid metabolism by enhancing gene expression and hepatic enzyme (acyl CoA oxidase, carnitine palmitoyltransferase, bifunctional enzyme, and 3-ketoacyl-CoA-thiolase) activities involved in fatty acid oxidation [66,67]. On the other hand, lignans reduce the activities of enzymes involved in lipogenesis (acetyl-CoA carboxylase, fatty acid synthase, ATP citrate lyase, glucose-6-phosphate dehydrogenase, and pyruvate kinase) by altering the gene expression [66]. ...
... Their study could also identify the identical and different gene expression profiles during sesame and Arabidopsis seed development and the genes specific to sesame seeds [126]. Sirato-Yasumoto et al. [67] reported that sesamin content in sesame seeds was controlled by polygenes, because F2 populations originating from reciprocal crosses between high sesamin and normal sesamin varieties showed a continuous distribution in sesamin content, and correlation coefficients between F2 and F3 generations were positive and highly significant for sesamin content. ...
... Sesame lignans have antioxidant and tocopherol-sparing activities [59][60][61][62]. They are reported to reduce cholesterol level [48,50,63] and exhibit antihypertensive [64] and anti-inflammatory activities [65] as well as affect lipid metabolism by enhancing gene expression and hepatic enzyme (acyl CoA oxidase, carnitine palmitoyltransferase, bifunctional enzyme, and 3-ketoacyl-CoA-thiolase) activities involved in fatty acid oxidation [66,67]. On the other hand, lignans reduce the activities of enzymes involved in lipogenesis (acetyl-CoA carboxylase, fatty acid synthase, ATP citrate lyase, glucose- 6-phosphate dehydrogenase, and pyruvate kinase) by altering the gene expression [66]. ...
... Their study could also identify the identical and different gene expression profiles during sesame and Arabidopsis seed development and the genes specific to sesame seeds [126]. Sirato-Yasumoto et al. [67] reported that sesamin content in sesame seeds was controlled by polygenes, because F2 populations originating from reciprocal crosses between high sesamin and normal sesamin varieties showed a continuous distribution in sesamin content, and correlation coefficients between F2 and F3 generations were positive and highly significant for sesamin content. ...
Chapter
Sesame is a valuable oilseed crop that contains various nutritionally rich bioactive compounds including lignans, tocopherol homologues, phytosterols, etc. Lignans are the product of oxidative coupling of β-hydroxyphenylpropane. Sesame has a combination of glycosylated lignans and oil-dispersed lignans. Based on their medicinal and pharmacological properties, the most important lignans are sesamin, sesamol, sesamolin, and sesaminol. Tocopherols (vitamin E compounds) are the lipid-soluble free radicals and constitute a major part of human diet. In sesame seeds, α-, γ-, and δ-tocopherols are found as tocopherol homologues. In addition to lignans and tocopherols, sesame is an important source of phytosterols, phytates, polyunsaturated fatty acids, and bioactive peptides. However, utilization potential of many of these compounds has not yet been fully understood. This chapter delves into the presence of multifarious bioactive components in sesame seeds, their biosynthetic pathway, and functional importance.
... Sesame lignans have antioxidant and tocopherol-sparing activities [59][60][61][62]. They are reported to reduce cholesterol level [48,50,63] and exhibit antihypertensive [64] and anti-inflammatory activities [65] as well as affect lipid metabolism by enhancing gene expression and hepatic enzyme (acyl CoA oxidase, carnitine palmitoyltransferase, bifunctional enzyme, and 3-ketoacyl-CoA-thiolase) activities involved in fatty acid oxidation [66,67]. On the other hand, lignans reduce the activities of enzymes involved in lipogenesis (acetyl-CoA carboxylase, fatty acid synthase, ATP citrate lyase, glucose-6-phosphate dehydrogenase, and pyruvate kinase) by altering the gene expression [66]. ...
... Their study could also identify the identical and different gene expression profiles during sesame and Arabidopsis seed development and the genes specific to sesame seeds [126]. Sirato-Yasumoto et al. [67] reported that sesamin content in sesame seeds was controlled by polygenes, because F2 populations originating from reciprocal crosses between high sesamin and normal sesamin varieties showed a continuous distribution in sesamin content, and correlation coefficients between F2 and F3 generations were positive and highly significant for sesamin content. ...
... In particular, secoisolariciresinol diglucosides (SDG), secoisolariciresinol, enterodiol, and enterolactone inhibited pancreatic α-amidase activity in a noncompetitive manner [43]. Sesamin and its metabolites also exhibited antihy- pertensive activities [44][45][46]. Moreover, the antioxidative activity of sesamin is believed to be involved in protecting the liver from oxidation by alcohols, lipids, and oxygen radicals [44,[47][48][49]. ...
... Sesamin and its metabolites also exhibited antihy- pertensive activities [44][45][46]. Moreover, the antioxidative activity of sesamin is believed to be involved in protecting the liver from oxidation by alcohols, lipids, and oxygen radicals [44,[47][48][49]. In human intestinal Caco 2 cells, pinoresinol suppressed expression of Cox-2, an inducible prostaglandin synthase that is responsible for the synthesis of prostaglandin H, a precursor of any other prostaglandins, leading to the decrease in the production of inflammatory factors, such as interleukin-6 and prostaglandin E2 [35]. ...
Chapter
Lignans are major phytochemicals biosynthesized in several plants including Sesamum, Linum, Forsythia, and Podophyllum genus, and a great variety of lignans have received wide attentions as leading compounds of novel drugs for tumor treatment and healthy diets to reduce of the risks of lifestyle-related diseases. Recent genome and transcriptome studies have characterized multiple novel lignan-biosynthetic enzymes, and thus have opened new avenues to transgenic metabolic engineering of various nonmodel dietary or medicinal plants. Forsythia and Linum are the most useful and prevalent natural and agricultural sources for the development of both transgenic foods and medicinal compounds. Over the past few years, transiently gene-transfected or transgenic Forsythia and Linum plants or cell cultures have been shown to be promising platforms for the sustainable and efficient production of beneficial lignans. In this chapter, we present the essential knowledge and recent advances regarding metabolic engineering of lignans based on their biosynthetic pathways and biological activities and the perspectives in lignan production via metabolic engineering.
... The results obtained suggested that somina did not produce any significant changes in gross behavior, autopsy [12] and liver function test (LFT) in rats (table 3). Our study is in agreements of previous studies suggest that different constituents of Somina Like sesame [26], Prunus amygdalus [27], Lagenaria vulgaris [28] and Lactuca scariola [29] individually, can be used without any adverse effect on liver function and protect the liver from oxidative damage [26]. In both generations, parameters regarding the LFTs are normal. ...
... The results obtained suggested that somina did not produce any significant changes in gross behavior, autopsy [12] and liver function test (LFT) in rats (table 3). Our study is in agreements of previous studies suggest that different constituents of Somina Like sesame [26], Prunus amygdalus [27], Lagenaria vulgaris [28] and Lactuca scariola [29] individually, can be used without any adverse effect on liver function and protect the liver from oxidative damage [26]. In both generations, parameters regarding the LFTs are normal. ...
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Objective: Somina (herbal medicine) is used in Pakistan as Unani anxiolytics. It is composed of five medicinal plants. The current work was designed to evaluate the general reproductive and teratogenic effects of somina in two consecutive generations of rats according to the OECD guideline. Methods: Fertility study (a two-phase study) was done in Sprague-Dawley rats. 1st part: three groups' female rats (10 rats each group) received different doses orally. First group: The control group (saline), a single oral human dose of somina (2 nd group: 285 mg/kg/day) and the high dose of somina (3 rd group: 1g/kg/day) during the whole period of gestation till the delivery of pups named as F1 Breed. For the second part of study ten females were selected from each F1 breed (control, somina 285 mg/kg/d, somina 1g/kg/day) and administered the same treatment from day first of mating than the entire period of gestation until F1 breed delivered pups (F2 breed). For F1 and F2 breed the fertility index and litter size were determined. Some of the female rats (F1 and F2) were anesthetized and autopsied. The blood sample was subjected to biochemical analysis and serum liver function test: bilirubin, gamma-glutamyl transferase (γGT), alanine aminotransferase (ALT: SGPT), aspartate aminotransferase (AST: SGOT) and alkaline phosphatase (ALP) were measured spectrophotometrically. The uterine growth index, fertility index, and litter size were also measured to evaluate the teratogenic effects of somina treated rats. Results: The data showed that any significant different (P>0.05) was not found during the maternal examination (uterine growth index, fertility index) and reproductive parameters (litter size, the quantity of fetus, aborted or absorbed fetus) in somina treated rats as compare to control rats (P>0.05). Control and treated Pups did not show any significant (P>0.05) malformation and any congenital defects. Non-significant (P>0.05) changes were observed in liver function test. It was found normal in all groups. Macroscopic autopsy examination also did not reveal any significant (P>0.05) pathological findings in the liver, kidneys, and uterus. Conclusion: The oral administration of somina during the gestational period of pregnant female rats was not teratogenic/fetotoxic. Any adverse or deleterious effects were not observed at the dose of 285 mg/kg (human dose) or 1g/kg (3times greater than the human dose) during pregnancy, and it is safe in rats.
... In vivo Liver diseases The rats fed with sesame seeds revealed that the activity of enzymes involved in fatty acid synthesis, including fatty acid synthase, glucose-6-phosphate dehydrogenase, ATPcitrate lyase, and pyruvate kinase, was significantly reduced [206] Chia seeds Polyphenols and ALA ...
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Plant-based foods are becoming an increasingly frequent topic of discussion, both scientificandsocial, due to the dissemination of information and exchange of experiences in the media. Plant-based diets are considered beneficial for human health due to the supply of many valuable nutrients, including health-promoting compounds. Replacing meat-based foods with plant-based products will provide many valuable compounds, including antioxidants, phenolic compounds, fibers, vitamins, minerals, and some ω3 fatty acids. Due to their high nutritional and functional composition, plant-based foods are beneficial in acute and chronic diseases. This article attempts to review the literature to present the most important data on nutrients of plant-based foods that can then help in the prevention of many diseases, such as different infections, such as Corona virus disease, pneumonia, common cold flu, asthma, and bacterial diseases, such as bronchitis. A properly structured plant-based diet not only provides the necessary nutrients but also can help in the prevention of many diseases.
... The seeds and fresh leaves are used as a poultice. The SSO maintains good cholesterol [High-Density Lipoprotein (HDL)] and lowers bad cholesterol [Low-Density Lipoprotein (LDL)] (Sirato-Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
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Chapter
Sesame (Sesamum indicum L.), often regarded as the “Queen of oil seed crops”, is the oldest oil seed crop mainly grown in the tropical and subtropical countries. Sesame seed oil (SSO) is of high-grade quality and has been cultivated for its multiple benefits since ancient times. Increased awareness on the medicinal, nutritional, beauty-cultural, and industrial applications of sesame has grown the international demand which in turn has increased the production in the sesame growing countries and expanded the international trading. Despite the continuous expansion in the global market, currently, Sri Lankan sesame remains as an orphan crop. Lack of high-yielding varieties, limited accessibility to developed varieties, resources, guidance, and facilities of transport and storage, seed shattering nature of the available varieties, changing weather patterns, unsteady market prices, and less awareness of the farmers on the market opportunities are the key factors limiting sesame cultivation in Sri Lanka. Limited product range and awareness on the numerous benefits of SSO, occasional unavailability of seeds, allergies reactions, taste of SSO have downturn the consumption of sesame. Sri Lanka where more than two third of the land experience dry climate, naturally has the ideal environment for cultivation of sesame, the only oil seed crop being exported from the country, yet with sporadic export volumes. Along with raised awareness among farmers and consumers, among many other factors, opportunities to generate numerous economic activities (expanded market opportunities, increased product range and customer base, introduced value-added products, modern economic uses such as harnessing biodiesel) may encourage both cultivation and trading while contributing to bioeconomy of the country. Overall, Sri Lanka inherits an excellent prospective for expanding sesame cultivation and improve the level of production.
... including antioxidant, antibacterial, cardiotonic, antidiabetic, hypocholesterolemia, anticancer, antiulcer, anti-inflammatory, and analgesic characteristics (Sirato-Yasumoto et al., 2001). In both experimental animals and humans, sesame has been shown to exhibit antioxidant activity, as well as blood pressure and serum lipid-lowering properties (Anilkumar, et al., 2010). ...
... The animal experiment showed that sesamin has been used to decrease blood lipids and blood glucose levels in the aorta of rats with metabolic syndrome (18). Several animal studies have also confirmed that the supplementation of sesame seeds or sesamin could decrease cholesterol levels (19,20). Hirata et al. (21) have experimented with sesamin on human subjects, and the results were surprising. ...
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Aims Sesamin, the main lignin constituent of sesame, plays a pivotal role in regulating physical state. Some studies have evidenced that the supplementation of sesamin may decrease cardiovascular disease risk. The goal of this systematic review was to summarize evidence of the effects of sesamin supplementation on obesity, blood pressure, and lipid profile in humans by performing a meta-analysis of randomized controlled trials. Data Synthesis Five databases (PubMed, Cochrane Library, EMBASE, Web of Science, and Scopus) were searched electronically from inception to July 2021 to identify randomized controlled trials that assessed the impact of sesamin on obesity, blood pressure, and lipid profile. Weighted mean difference (WMD) and standard deviation (SD) were used to present the major outcomes. Conclusions Seven trials (n = 212 participants) were included in the overall analysis. Results showed that sesamin supplementation caused a great reduction in TC (WMD: -10.893 mg/dl, 95% CI: −19.745 to −2.041, p = 0.016), LDL-c (WMD: -8.429 mg/dl, 95% CI: −16.086 to −0.771, p = 0.031), and SBP (WMD: −3.662 mmHg, 95% CI: −6.220 to −1.105, p = 0.005), whereas it had no effect on HDL-c, TG, DBP, or weight. Subgroup analysis showed that duration, parallel design, and unhealthy status can affect TC, LDL-c, and SBP evidently. We did not discover a strong link between indicators’ changes and duration of supplementation. Sesamin can be used as an obtainable dietary supplement to improve blood pressure and blood lipids, and further as a health product to prevent cardiovascular diseases.
... The crude protein content in the sesame meal ranges from 47.1% to 52.9% and in terms of the amino acid composition of the protein, it is similar to that of soybean meal (El-Saidy, Mahmoud and Tonsey, 2009). -Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
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Dengue has been recognized as one of the major public health concerns in Sri Lanka nowadays. Suppression of vector population and limiting the vector-human contact has become the main strategies in the disease control programmes. In control of dengue vectors, chemical-based methods are widely used to reduce vector densities. However, downsides allied with the chemical-based control approaches such as the development of resistance against insecticides, adverse impact to the non-target organisms and environment have widened the attention toward eco-friendly methods in the integrated vector control concept for vector management. In Sri Lanka, several biological-based control approaches have been evaluated and used in control progammes with different magnitudes. However, many of these approaches have not been involved in the vector control strategic plan. The present work reviews the biological vector control approaches which have been evaluated in Sri Lanka at some scale and reiterate the potential strengths in integrated vector management.
... The crude protein content in the sesame meal ranges from 47.1% to 52.9% and in terms of the amino acid composition of the protein, it is similar to that of soybean meal (El-Saidy, Mahmoud and Tonsey, 2009). -Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
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Microalgae are a diverse group of ubiquitous microorganisms which have important ecosystem services and industrial applications in sustainable bioeconomy
... The crude protein content in the sesame meal ranges from 47.1% to 52.9% and in terms of the amino acid composition of the protein, it is similar to that of soybean meal (El-Saidy, Mahmoud and Tonsey, 2009). -Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
Chapter
Role of microalgae in sustainable bioeconomy
... The crude protein content in the sesame meal ranges from 47.1% to 52.9% and in terms of the amino acid composition of the protein, it is similar to that of soybean meal (El-Saidy, Mahmoud and Tonsey, 2009). -Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
... The crude protein content in the sesame meal ranges from 47.1% to 52.9% and in terms of the amino acid composition of the protein, it is similar to that of soybean meal (El-Saidy, Mahmoud and Tonsey, 2009). -Yasumoto et al., 2001). The antioxidant sesamin reduces LDL levels while HDL levels are increased. ...
... Sesame seeds contain bioactive components including phenolics, vitamins, phytosterols, and polyunsaturated fatty acids, which provides a beneficial effect on human health [6]. Sesame seed lignans have been reported to have high antioxidant activity both in vitro and in vivo experiments [13]. ...
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Background: Consumption of sesame seed products is increasing worldwide, and sesame may be suitable as a quality protein source for preschool children when combined with other sources of plant proteins.
... Carbohydrates in sesame seed are composed of 3.2% glucose, 2.6% fructose and 0.2% sucrose while the remaining quantity is dietary fibers. Sesame seeds have desirable physiological effects including antioxidant activity, blood pressure and serum lipid lowering potential as proven in experimental animals and humans (Sirato-Yasumoto et al., 2001). Sesame seeds are used as an excellent source of copper and calcium. ...
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A field experiment was carried at the Agronomy Research Field, Hajee Mohammad Danesh Science and Technology University, Dinajpur, Bangladesh to find out the effect of sulphur and zinc on the growth and yield traits of sesame. The experiment consisted two factorial naming Factor A: Three levels of sulphur as 0 (S1), 18 (S2) and 24 (S3) (0, 100, 150 kg gypsum/ha), and Factor B: Three levels of zinc as 0 (Zn1), 1.44 (Zn2) and 2.88 (Zn3) (0, 4.0, 8.0kg zinc sulphate/ha). The total treatment combinations were i) T1 (S1Zn1), ii) T2 (S1Zn2), iii) T3 (S1Zn3), iv) T4 (S2Zn1), v) T5 (S2Zn2), vi) T6 (S2Zn3), vii) T7 (S3Zn1), viii) T8 (S3Zn2), ix) T9 (S3Zn3). The experiment was laid out in a Randomized Complete Block Design (RCBD) with three replications. Seasame cv. BARITil 4 was used as test crop. The experimental results revealed that sulphur (18 kg ha-1) + zinc (1.44 kg ha-1) (S2Zn2) applications greatly increased the leaf, 98 ISSN 2717-7238 ISPEC Journal of Agricultural Sciences Year 3/ 2019, Volume-3, Issue-1 | https://ispecjournal.com petiole, stem and root at different days after sowing. Higher dry weight of different parts and yield traits i.e. no of capsules and capsules weight were produced by the application of sulphur (18 kg ha-1) + zinc (1.44 kg ha-1) among all treatment combinations at different growth stage.
... Also, the protective effect of flavonoid of sesamum seed was attributed to its antioxidant and free radical scavenging properties (Takeoka and Dao (2003). Sesamin has been known to protect the liver from oxidative damage (Sirato Yasumoto et al., 2001). ...
... It contains compounds such as sesamin, sesaminol, gammatocopherol, cephalin, and lecithin. These compounds impart many of the pharmacological activities such as antioxidant, antibacterial, cardiotonic, antidiabetic, hypocholesterolemia, antitumor, antiulcer, anti-inflammatory, and analgesic properties to sesame [24]. Sesame is proven to possess antioxidant activity, blood pressure and serum lipidlowering property in experimental animals and humans [25]. ...
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Objectives: Bisphosphonates are known to cause gastritis and only few studies have evaluated the use of plant extracts in the treatment of bisphosphonate induced peptic ulcers. In the present study, we examined the effect of sesame seed extract in the alendronate-induced gastric ulcer in adult Wistar rats. Methods: Thirty adult Wistar rats (180–250 g) of both sexes, divided into five groups (n=6) were used: Group 1 (vehicle control) – 0.9% saline, Group 2 (ulcer control) – alendronate 60 mg/kg, Group 3 (standard) – alendronate 60 mg/kg + pantoprazole 30 mg/kg/day, Group 4 (test groups) – alendronate 60 mg/kg + sesame 0.5 mg/kg, and Group 5 (test groups) – alendronate 60 mg/kg + sesame 1 mg/kg. All drugs were given orally once daily for 7 days except for alendronate given only on day 1. On day 8, rats were sacrificed, and stomach tissues were analyzed macroscopically for ulcers. Estimation of gastric pH, acidity, and volume was done along with mucin content measurement. One-way ANOVA followed by Tukey’s post hoc test was used for statistical analysis with p<0.05 taken as significant. Results: Our study found that sesame extract given therapeutically at doses of 0.5 and 1 mg/kg showed comparable results with that of pantoprazole 30 mg/kg. Both the doses of sesame, 0.5 and 1 mg/kg showed similar gastroprotective activity against alendronate-induced gastric ulcers in Wistar rats. Conclusion: The findings of this study clearly demonstrated the protective effects of Sesame against alendronate-induced gastric ulceration.
... Carbohydrates in sesame seeds consist of 3.2% glucose, 2.6% fructose and 0.2% sucrose while the remaining quantity is dietary fibers. Also, they have desirable physiological effects including antioxidant activity, blood pressure and serum lipid lowering potential as proven in experimental animals and humans (Sirato-Yasumoto et al., 2001). Sesame is rich in sulfur containing amino acids and limited in lysine and contains significant amounts of oxalic (2.5%) and phytic (5%) acids (Kapadia et al., 2002). ...
... Known as phenolic plant components, lignans have no nutrients or calories but are bioactive. Sesame and flax seeds are the richest sources for lignans and other seeds, whole grains, fruits, and vegetables have the least amounts of it (22). Sesame seed lignans can modulate fatty acid metabolism as well as inhibit cholesterol absorption and biosynthesis, which improve liver functions and promote immunity. ...
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Background: Atherosclerosis is a chronic inflammatory disease of the vascular wall which can alter the whole vascular system of both the aorta and coronary arteries. Sesame seeds are one of the richest sources of dietary lignans which exhibit diverse functions and valuable effects such as anti-hypertensive, anti-inflammatory, and anti-oxidative activities. Objectives: In this study, the Effect of sesame lignans on carotid intima-media thickness (CIMT), serum lipid profile, and serum levels of VEGF, VCAM-1, ICAM-1 and vWF were evaluated in cardiovascular (CVD) patients. Methods: In this double-blind, randomized, placebo-controlled clinical trial, thirty-six CVD patients who were candidates for angiography participated for 10 weeks. The subjects were asked to use 500 mg/day sesame lignans (lignan group, n = 19) or placebo (placebo group (starch), n = 17). The CIMT was measured by ultrasound and fasting blood samples were taken before and after the intervention. Results: Sesame lignans supplementation showed a significant decrease in both left and right CIMT, serum lipid profile, fasting blood glucose, and ICAM-1 serum levels compared to baseline and placebo (P < 0.05). Conclusions: These findings indicate that sesame lignans may contribute to the reduction of CIMT and prevent future cardiovascular events and so may be considered as a complementary therapeutic approach in CVD
... Sesame is rich in furofuran lignan (Kamal-Eldin et al. 2011). Sesamin and Sesamolin is fat-soluble present in sesame seeds and oil at a ratio of 2:1 (Yasmoto et al. 2001). Sesamin, the most abundant oil-soluble lignan and exerts diverse biological functions (Namiki, 2007). ...
... Sesamin (6) and its metabolites exhibited antihypertensive activities 76,[170][171][172] . Sesamin (6) is also an insecticide 173 . ...
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Since ancient times, medicinal plants and pharmacologically active products obtained from different natural sources play an important role in human health. Plants belonging to the genus Artemisia possess a great biological potential and it is a well-studied genus in the fields such as systematics (including molecular phylogenetics) and genome organization. Many species of the genus (e.g., A. absinthium, A. annua, A. vulgaris, A. abrotanum, A. arborescens) are widely exploited, because of their high economic value as medicines, food and ornamentals. Withal, in such a large genus, some hiatus must inevitably exist, concerning attainments and potentials that individual species possess. Most of the studies are focused on bioactivity and pharmacology of sesquiterpene lactones. Lignans are unjustly neglected, even though they as well exhibit a wide range of bioactivities. Motivated by that fact, we tried to consolidate findings on bioactive lignans accumulated through the years, with the logical perspectives on further work on isolation and identification of new bioactive lignans and the exploitation of lignans as substances of potential pharmacological interest. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172047]
... Sesamin is a lignan separated from Fagara plants. Sesame oil is used as a dietary fat-reduction supplement [20,21]. According to Boulbaroud et al., sesame oil has preventive effects on bone loss, which was confirmed in an ovariectomized (OVX) rat model [22]. ...
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BACKGROUND Osteoporosis is a common osteopathy, resulting in fractures, especially in elder people. Sesamin has many pharmacological effects, including supplying calcium. However, how sesamin might prevent osteoporosis is still under study. MATERIAL AND METHODS Bone marrow stromal cells (BMSCs) extracted from rat femur were induced for osteoblastic differentiation. Cell proliferation, alkaline phosphatase (ALP), osterix (OSX), SRY-box 9 (SOX9), runt-related transcription factor 2 (RUNX2), osteocalcin (OCN), ß-catenin, low density lipoprotein receptor-related protein 5 (LRP5), and glycogen synthase kinase-3ß (GSK-3ß) levels in BMSCs were detected in the presence or absence of sesamin (1 μM or 10 µM). In addition, FH535 (1 μM) was used to silence Wnt/ß-catenin in vitro. Ovariectomized (OVX) rats were established and intragastrically administrated sesamin (80 mg/kg), and then the rat bones were analyzed by micro-computed tomography. Osteocalcin and collagen type I were measured in the rat femurs. RESULTS Sesamin had no influence on BMSC proliferation. Higher sesamin concentration promoted Wnt/ß-catenin activity and enhanced more expressions of ALP, OSX, SOX9, RUNX2, and OCN, gradually and significantly (P<0.05). Silencing Wnt/ß-catenin weakened the enhancement on RUNX2 and OCN expression. Sesamin (80 mg/kg) promoted bone structure in ovariectomized rats, and significantly enhanced osteocalcin and collage type I expression (P<0.05). CONCLUSIONS Sesamin promoted osteoblastic differentiation of rat BMSCs by regulating the Wnt/ß-catenin pathway, and improved rat bone structure. Sesamin could have therapeutic and preventive effects on osteoporosis.
... The B. pulverulenta-derived compounds are lignans (Table 1) and, few reports are available on lignans as well as neolignans that were isolated from other Beilschmiedia species like B. kunstleri, B. tsangii and B. volckii. As the most prominent lignan compound which is present in many natural products including the sesame seeds, sesamin is a known nutritional supplement with potentials to confer biological activities such as protection against Alzheimer's and Parkinson's disease as well as antioxidant and antiinflammatory effects (Sirato-Yasumoto et al., 2001;Zhao et al., 2016). On the other hand, (+)-sesartemin which is an isomer of (+)-excelsin has been reported to lower isolation-induced aggressions in experimental animals (MacRae and Towers, 1984). ...
Article
Angelica polymorpha and Beilschmiedia pulverulenta are medicinal plants locally used by people in some parts of Asia and Africa due to their beneficial health effects particularly in the treatment of Alzheimer's disease (AD). The phytoconstituents responsible for such bioactivity have recently been identified in the plants. Herein, in silico approach was used to explore the interaction of such phytochemicals with acetylcholinesterase (AChE) as a validated target in the treatment of AD to provide insights into their precise binding pattern and affinity, order of chemical interaction, inhibitory potential and residues that contribute to the enzyme-phytoconstituent complex stability. With binding affinity ranging from -7.0 kcal/mol to -10.2 kcal/mol and tacrine-comparable orientation, the chemical scaffold of the phytochemicals from both plants displayed deep penetration and fit conveniently into the narrow gorge of AChE. Optimisation of these ligands scaffold might yield new AChE inhibitors with desirable higher efficacy.
... The B. pulverulenta-derived compounds are lignans (Table 1) and, few reports are available on lignans as well as neolignans that were isolated from other Beilschmiedia species like B. kunstleri, B. tsangii and B. volckii. As the most prominent lignan compound which is present in many natural products including the sesame seeds, sesamin is a known nutritional supplement with potentials to confer biological activities such as protection against Alzheimer's and Parkinson's disease as well as antioxidant and antiinflammatory effects (Sirato-Yasumoto et al., 2001;Zhao et al., 2016). On the other hand, (+)-sesartemin which is an isomer of (+)-excelsin has been reported to lower isolation-induced aggressions in experimental animals (MacRae and Towers, 1984). ...
... (+)-Sesamin is one of the most abundant lignans in sesame (Sesamum indicum L.) seed and oil [14]. It has been reported that sesamin possesses beneficial effects on improving lipid metabolism and liver damages in animal and human study [15][16][17]. Importantly, sesamin also has anti-inflammatory and potential neuroprotective effects. A previous study demonstrated that sesamin inhibited LPSinduced cytokines production in murine microglia and BV-2 cells [14]. ...
Article
Depression is a mood disorder that is related to neuroinflammation and cognition loss. This study is aimed to determine the potential antidepressant effects of (+)-sesamin, a lignan component of sesame, in a mild stress-induced depression mouse model. CD-1 mice were treated with chronic unpredictable mild stress (CUMS) process and orally administrated with sesamin (50 mg/kg/d) for 6 weeks. Behavioral tests including forced swimming test, tail suspension test, open field test, and elevated plus maze test demonstrated that sesamin treatment inhibited CUMS-induced mice depressant-like behaviors and anxiety, without changing immobility. It was found that sesamin prevented stress-induced decease levels of 5-HT and NE in striatum and serum. Cognitive deficits were assessed using Y-maze and Morris water maze test. Sesamin treatment also prevented stressed-induced memory impairments and neuronal damages. Consistently, sesamin also enhanced synapse ultrastructure and improved expressions of PSD-95 in stressed mice hippocampus with improving neurotrophic factors expression including BDNF and NT3. Moreover, sesamin treatment significantly prevented CUMS-induced neuroinflammation by inhibiting over-activation of microglia and expressions of inflammatory mediators including iNOS, COX-2, TNF-α and IL-1β in stressed mice hippocampus and cortex. These results illustrated that sesamin markedly improved CUMS-induced depression and memory loss via inhibiting neuroinflammation, which indicate that as food component, sesamin might be also a novel potential therapeutic for depression.
... Sesamin and its metabolites also exhibited antihypertensive effects and the antioxidative activity ( Nakai et al., 2003;Nakano et al., 2002;Satake et al., 2013Satake et al., , 2015Satake et al., , 2016SiratoYasumoto et al., 2001). The latter is thought to be implicated with protective effects on the liver from oxidation by alcohols, lipid peroxides, and oxygen radicals ( Akimoto et al., 1993;Satake et al., 2013Satake et al., , 2015Satake et al., , 2016Sirato-Yasumoto et al., 2001;Tada et al., 2013). In human intestinal cell lines, Caco 2 cells, pinoresinol suppressed the gene expression of Cox-2 that is an inducible synthase of a basal prostaglandin, prostaglandin H ( During et al., 2012;Satake et al., 2013Satake et al., , 2015Satake et al., , 2016. ...
...  Sesamin and sesamolin are lignan derivatives found in seasame oil [117] whereas flavonol lignans hydnocarpin, hydnowightin and neohydnocarpin isolated from the seeds of Hydnocarpus species are lipid lowering, anti-inflammatory and antitumoral in animal experiments [118]. ...
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Antioxidants are one of the vital requirement for human health and it protect our immune system and tried to neutralize free radicals. In other words, antioxidant compounds reduce the burden rate of various diseases (infectious or chronic or cardiovascular) especially cancer and heart. Normally, these antioxidants are reported in various medicinal plants including food material that are present in simple or complex form and showed its importance as health protecting factor. There are number of components that are included under the category of antioxidants i.e. nutrient derived or based antioxidants; antioxidant as enzymes; metal binding based proteins and many other antioxidant phytonutrients that are present in a wide variety of plant foods. In this study, we collected some information about various antioxidants especially flavonoids and polyphenols from various medicinal plants that are beneficial for human health.
... Sesame oil heals and protects areas of mild scrapes, cuts and abrasions (Jeng and Hou, 2005). Sesame seed oil maintains good cholesterol (high density lipoprotein, HDL) and lower bad cholesterol (low density lipoprotein, LDL) (Yasumoto et al., 2001). Sesamin binds to and activates a receptor in the body called Peroxisome Proliferator-Activator Receptor Alpha (PPARalpha). ...
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Sesame is important oilseed crop of tropical and sub tropical region, renowned for its high oil content (up to 60% oil), hence sesame is known as the king of oil seeds. Sesame seed oil contains 83% - 90% unsaturated fatty acids, 20% proteins and various minor nutrients such as vitamins and minerals, large amount of characteristic lignans, such as sesamin, sesamol, sesamolin and tocopherols. Sesame seeds with high amounts of nutritional components are consumed as a traditional health food for its specific antihypertensive effect, anticarcinogenic, anti-inflammatory and antioxidative activity. Besides food, sesame also finds its uses in application areas such as pharmaceutics, industrial, and as biofuel. Sesame is used as active ingredients in antiseptics, bactericides, viricides, disinfectants, moth repellants, and anti-tubercular agents. In spite of being a good source of “healthy oil” in terms of presence of high amounts of PUFA and high antioxidant content, it is not grown on a large extent due to very poor yields. Therefore, serious efforts are necessary for selecting varieties of good quality and high adaptive potential to the diverse climatic situations. There should be effective strategies adapted to produce climate ready sesame variety using modern biotechnological approach.
... This lead to reversible and irreversible changes that caused microbial cell death. Considering the antimicrobial effect of other oils (Oil pulling a wonderful therapy, 2011; Thaweboon et al., 2011;Karach, 1992), including sesame oil (Ram et al., 1990;Hasan et al., 2000;Kato et al., 1998;Sirato-Yasumoto et al., 2001), sunflower oil (Cooney et al., 2001;Sechi et al., 2001), palm oil (Umuahia et al., 2015), rice bran oil (Dey Arpan, 2013) and soy bean oil (Karthikeyan Ramalingam et al., 2011), it was proposed that small amounts of saturated fatty acid, i.e. lauric acid, in these oils may play a role in their antimicrobial properties. Though there are many studies conducted on the efficacy of virgin coconut oil in various fields of medicine, there are no documented studies on specific periodontal pathogens and its efficacy in reducing the bacterial count. ...
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Background: Periodontitis is a polymicrobial disease which effects bone and the supporting structures of teeth. The treatment for periodontal diseases has moved towards an antimicrobial model of disease management. With the threat of wide spread antibiotic resistance rendering many antibiotics useless against many diseases, there is an increased necessity to develop a novel antimicrobial based treatment for effective disease prevention. In this regard an invitro study was conducted comparing virgin coconut oil with standard chlorhexidine mouth wash (0.2%) on five periodontal pathogens. Methods: An invitro study on the five putative pathogens of periodontal disease was conducted using minimum inhibitory concentration (MIC), maximum bacterial count (MBC) and time kill curve methods. The culture media used was Brain heart infusion broth. Results: The results showed that all the organisms were resistant to virgin coconut oil, while there was varying degree of sensitivity to chlorhexidine. Conclusion: The results of the current study showed that virgin coconut oil has no therapeutic effect in the treatment of active periodontal disease, while chlorhexidine was found to have bacteriocidal effect on against Prevotella intermedia, Porphyromonas gingivalis and Tenerella forsythia and bacteriostatic effect on against Fusobacterium nucleatum and Aggregatibacter actinomycetum commitans.
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We investigated the potential efficacy and underlying mechanisms of Lotus seed Resistant Starch (LRS) for regulating hyperlipidemia in mice fed a High-fat Diet (HFD). Mouse were fed a normal diet (Normal Control group, NC group), HFD alone (MC group), HFD plus lovastatin (PC group), or HFD with low/medium/high LRS (LLRS, MLRS, and HLRS groups, respectively) for 4 weeks. LRS supplementation significantly decreased body weight and significantly reduced serum levels of total cholesterol, triglycerides, low-density lipoprotein cholesterol, and high-density lipopro-tein cholesterol compared with the MC group. LRS also significantly alleviated hepatic steatosis, especially in the MLRS group, which also showed a significantly reduced visceral fat index. LLRS supplementation significantly regulated genes associated with glycerolipid metabolism and steroid hormone biosynthesis (Lpin1 and Ugt2b38), MLRS significantly regulated genes related to fatty acid degradation, fatty acid elongation, and glycerolipid metabolism (Lpin1, Hadha, Aldh3a2, and Acox1), whereas HLRS significantly regulated genes related to fatty acid elongation and glycerolipid metabolism (Lpin1, Elovl3, Elovol5, and Agpat3). The fatty acid-degradation pathway regulated by MLRS thus exerts better control of serum lipid levels, body weight, visceral fat index, and liver steatosis in mice compared with LLRS- and HLRS-regulated pathways.
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Background: Inflammation is a defensive mechanism that protects the body from noxious stimuli. Currently available anti-inflammatory drugs are associated with numerous adverse effects. Hence there is a need for novel anti-inflammatory agent with better safety profile. The current study was conducted to investigate the anti-inflammatory activity of the ethanolic and hexane extracts of Sesamum indicum L. seeds by carrageenan and formalin induced paw edema respectively in Wistar rats. Methods: The animals were divided into 5 groups. Group 1 was given normal saline orally and Group 2 Indomethacin. Groups 3-5 in Carrageenan model were administered ethanolic extract of Sesamum indicum L. at three doses - 150, 200 and 250 mg/kg respectively, whereas in Formalin model, they were given hexane extract at the same doses orally. Anti-inflammatory potential was investigated by Carrageenan and Formalin induced models of inflammation. Results: Sesamum indicum L. ethanolic extract at 250 mg/kg exhibited a significant inhibition of paw edema at 4th hour while hexane extract at all doses caused significant inhibition of paw edema. The percentage inhibition of edema at 4th hour of hexane extract at 250 mg/kg was comparable to Indomethacin. Conclusion: The ethanolic and hexane extracts of Sesamum indicum L. seeds have anti-inflammatory potential. The activity of hexane extract is comparable to indomethacin.
Chapter
Sesame seed has higher oil content (around 50%) than most of the known oilseeds, although because of the labor‐intensive harvesting of the seeds, its production is far less than the major oilseeds such as soybean or rapeseed. Sesame oil is generally regarded as a high‐priced and high‐quality oil. It is one of the most stable edible oils despite its high degree of unsaturation. The presence of natural phytochemicals accounts for both the superior stability of sesame oil and the beneficial physiological effects of sesame.
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Background: Melanin protects against the harmful effects of ultraviolet irradiation to the mammalian skin. However, melanin overproduction causes several esthetic problem like a melasma, freckle, age spot and chloasma. So, the development of anti-melanogenic agents is important for the prevention of serious hyperpigmentation diseases. Methods: This study evaluated the anti-melanogenic effect of sesamolin, a lignan compound isolated from sesame seeds, on melanogenesis induced by 3-isobutyl-1-methylxanthine in B16F10 melanoma cells using zymography, tyrosinase inhibitory activity, western blot, and reverse transcription polymerase chain reaction analysis. Also, docking simulations between sesamolin and tyrosinase were performed using Autodock vina, and the skin irritancy of sesamolin was predicted by quantitative structure-activity relationship (QSAR) analysis. Results: Sesamolin significantly inhibited the expression of melanogenesis-related mRNA levels, as well as proteins such as tyrosinase and tyrosinase-related proteins 1 and 2. Sesamolin inhibitory activity was dose-dependent, and 50 µM sesamolin demonstrated the strongest competitive inhibition against intercellular tyrosinase and melanin synthesis without exerting cytotoxic effects. Tyrosinase docking simulations revealed that sesamolin (-6.5 kcal/mol) bound to the active site of tyrosinase more strongly than the positive control (arbutin, -5.7 kcal/mol). Conclusion: Sesamolin is a good candidate for melanogenic inhibition. However, sesamolin was predicted as a weak sensitizer by Derek EC3 prediction. It is necessary to confirm the safety of sesamolin as a cosmetic material in a biological skin toxicity experiment.
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This study aimed to investigate the inhibitory activity of key enzymes linked to type 2 diabetes (α-amylase and α-glucosidase) and the antioxidant properties of non polar (n-hexane) extracts from Coffea arabica, Citrus lanatus, Cucumis melo, Cuminum cyminum, Cocos nucifera, Coriandrum sativum, Foeniculum vulgare, Nigella sativa, Rhus coriaria, Pimpinella anisum, Syzygium aromaticum, and Sesamum indicum collected in Lebanon. Extracts were analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The antioxidant activity was investigated by using different in vitro methods namely 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), Ferric Reducing Ability Power (FRAP), and β-carotene bleaching tests. C. melo showed the highest α-glucosidase inhibitory activity with an IC50 value of 25.55 μg/ml, followed by C. lanatus white seeds and S. indicum (IC50 of 34.41 and 38.78 μg/ml, respectively). S. indicum exhibited also the highest protection of lipid peroxidation with IC50 values of 0.07 and 0.06 mg/ml after 30 and 60 min of incubation, respectively.
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Oxidative stress plays an important role in the etiology and pathogenesis of many chronic diseases such as atherosclerosis, hypertension, diabetes mellitus and cancers. Dietary intake of antioxidants can inhibit or delay the oxidation of susceptible cellular substrates so prevent oxidative stress. The present study was designed to investigate potential protective and ameliorate effects of sesame oil and jojoba oil against potassium bromate (KBrO3)-induced oxidative stress using experimental rats. Thirty five of rats were randomly divided into five groups, seven rats each. Group 1 was fed on the basal diet and kept as a negative control group (normal rats). The other 4 groups were injected by a single intraperitoneal dose of KBrO3 at dose of 125 mg/ kg body weight for induction of oxidative stress. Group 2 was left as a positive control group and groups 3, 4 and 5 were fed on supplemented diet with 5% sesame oil, jojoba oil and mixture of them, respectively. The obtained results revealed that the injected intoxicated groups with sesame oil (SO) or jojoba oil (JO) or mixture of them had significant reduced in serum levels of total cholesterol, triglycerides, LDL-c, total bilirubin, blood urea nitrogen, uric acid, creatinine, malondialdehyde (MDA), activity of aspartate aminotransferase (AST), alanine aminotransferase (ALT) and alkaline phosphatase (ALP) enzymes and significant increased in feed intake, body weight gain, serum levels of HDL-c, total antioxidant capacity, reduced glutathione (GSH), activity of glutathione peroxidase (GPx) superoxide dismutase (SOD) and catalase (CAT) enzymes. Moreover, there is a significant decrease in MDA and increase in GSH content and activity of antioxidant enzymes (GPx, SOD and CAT) in liver tissues as well as partially improvements in liver structures of liver and kidneys compared to those of positive intoxicated control group. The best improvements of all the biochemical parameters and histological structures of liver and kidneys which were tended toward normal results were observed in treated KBrO3-intoxicated rats with mixture of SO with JO. In conclusion, the present findings suggested that regular intake of SO or JO may be useful in improving liver and kidney functions and may protect against KBrO3 induced oxidative stress in rats by exhibiting stronger antioxidant activity. The mixture of SO with JO provide the preferable effects.
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Prevalence of obesity has received global attention in recent years, and lipid consumption has been considered as one of the direct reasons for obesity and related diseases. However, increasing evidences have indicated that edible vegetable oils could exert non-negligible physiological benefits in daily diet, including suppression of appetite, blood lipid lowering, prevention of adipocyte synthesis, and reduction of inflammatory response. Bioactive phytochemicals in lipids and oils, such as tocopherol, phenolic compound, and phytosterol, play an important role in these effects in vitro and in vivo studies. For these reasons, the present review focusses on minor bioactive components in oil and their anti-obesity effects, aiming to provide a systematic information on the relationships between these minor components and obesity, and related diseases.
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The aim of the present study was to investigate the effect of black sesame seeds ethanol extract (BSSEE) against nonalcoholic fatty liver disease (NAFLD) in fructose-fed mice. Mice were fed a standard diet without or with 30% fructose in drinking water for 8 consecutive weeks, while mice in three BSSEE tested groups received different doses of BSSEE (0.5, 1 and 2 mL/kg) once a day from the 5th week to the 8th week. Administration of BSSEE dose-dependently exerted antiobesity and protective effect against metabolism disorder in fructose-fed mice. Histological examinations indicated that administration of BSSEE obviously reduced hepatic lipid accumulation. Insulin tolerance test (ITT) and glucose tolerance test (GTT) along with decreases of serum insulin and glucose levels by BSSEE treatment suggested the improvement of body insulin resistance, and administration of 1 and 2 mL/kg BSSEE mitigated liver insulin resistance as the evidences of down-regulated expression of phospho-JNK1/2/3, phospho-NF-κB p65, phospho-IRS1 and phospho-IKK alpha/beta, up-regulated XBP1 expression and reductions of TNF-α and IL-6 levels. In addition, BSSEE treatment ameliorated hepatic oxidative stress through increasing GSH, vitamin C and Nrf2 levels, decreasing MDA and NO levels, and enhancing SOD, CAT and GSH-Px activities. These results demonstrated that BSSEE showed protective effects against NAFLD-related metabolic diseases in fructose-fed mice. Therefore, BSSEE may be a potent dietary supplement to ameliorate the diseases.
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Introduction: Burning Mouth Syndrome (BMS) is a condition which is characterised by xerostomia, stomatopyrosis, dysgeusia and primarily affects the women of perimenopausal age. Despite the plethora of trials that have been going on since decades for management of this condition, there seems to be no definitive cure till date, which is mainly attributed to the ambiguity of this condition. Oil pulling is a simple, ancient technique which can be used as an adjunctive or supplemental therapy in a number of conditions, including BMS. Aim: To assess the efficacy of oil pulling therapy using sesame oil on xerostomia and stomatopyrosis in patients suffering from primary BMS. Materials and Methods: This is a prospective study conducted at I.T.S. Dental College, Greater Noida, Uttar Pradesh, India, between April 2016 to April 2017 and included a total of 25 patients. On the basis of the detailed case history and complete haemogram, patients clinically diagnosed with primary BMS were advised oil pulling therapy once daily for a period of three months and symptoms of xerostomia and stomatopyrosis were assessed at the end of every month using Visual Analog Scale (VAS). Paired t-test was applied. The level of significance was set at p
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The inhibitory effect of lignan-rich sesame oil (SSO) against the endoplasmic reticulum (ER) stress and apoptosis induced by a high-fat diet (HFD) was studied, and its mechanism of action was elucidated in a comparison with soybean oil (SBO), which contains similar unsaturated fatty acid content but has no lignans. The HFD was prepared by adding 20% (w/w) lard (LD), SSO, or SBO to chow diet and provided for 12 weeks. In the SSO group, expression of ER stress and proapoptotic markers were downregulated, compared with levels in the LD group. However, these effects were not observed in the SBO group. The hepatic triacylglycerol concentration and expression of lipogenic enzyme in the SSO group were lower than that in the LD and SBO groups. These results show that SSO is able to decrease HFD-induced ER stress and apoptosis, and these effects were likely caused by its lignan compounds.
Chapter
Sesame is an erect annual (or occasionally, a perennial) of the PEDALIACEAE family that grows to a height of 0.5–1.5 m, depending on the variety and the growing conditions. Some varieties are highly branched, whereas others are unbranched. Leaves, 7.5–12.5 cm, simple or, when variable, with upper ones narrowly oblong, middle ones ovate and toothed and the lower ones lobate or pedatisect. Flowers are white, pink, or mauve-pink with dark markings, borne in racemes in the leak axils. The fruit is capsular, oblong-quadrangular, slightly compressed, deeply four grooved, 1.5–5 cm long. Seeds are black, brown, or white, 2.5–3 mm long and approx 1.5 mm wide. In general, the unbranched varieties mature earlier. At maturity, leaves and stems tend to change from green to yellow to red. The leaves will begin to fall off the plants.
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Sesame seeds and oil are being used by man since ancient times for culinary and non-culinary aspects such as in cosmetics, medicinal, insecticidal, pesticidal and bactericidal products. The sesame seeds contain unique nutraceutical compounds namely sesamol, sesamin, sesamolin, sesaminol, sesamolinol generally termed as lignans and their glucosides (which are poly-phenolic in nature but insoluble in oil). Apart from these, sesame oil is rich in unsaturated fatty acids and tocopherol content. These lignans contribute to the various health benefits like lowering of bad cholesterol, antioxidative activity (cancer preventive action), hypoglycaemic activity, hemostat activity, increase in plasma and liver tocopherol content, and reduction in coronary heart diseases (CHD). Therefore including sesame seeds and oil in the diet provides nutraceuticals which are essential for growth and well-being.
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Changes in the antioxidative activities and contents of sesame lignans and polar components, and in free amino acids of two kinds of sesame seed during germination were investigated. Gold sesame (Turkey), which is marketed as germination sesame, and gomazou, which contains large amounts of sesamin and sesamolin, were used. The sesamin and sesamolin contents of the two kinds of sesame seed during germination didn't decrease by any notable extent, and it is presumed that their physiological functions were retained. The contents of polar components in gold sesame increased during the first 24 hours of germination, but suddenly decreased 48 hours later. Although their contents in gomazou also decreased with germination, more remained than in gold sesame. It is presumed that the changes in DPPH radical-scavenging and SOD activities of both types of sesame seed during germination were both correlated with change in polar components. The organoleptic evaluation produced the highest score for the germinated gold sesame, but the taste score was not correlated with the content of free amino acids. GABA was found to increase during the germination of gomazou.
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The effects of various dietary fats on the activity of 3-hydroxy-3-methylglutaryl-Coenzyme A (HMG-CoA) reductase in rat liver microsomes, the rate-limiting enzyme in cholesterogenesis, were examined. A series of experiments demonstrated the dependency of the HMG-CoA reductase activity on the nature of dietary fats. When saturated fats with chain length of 12 to 18 were the dietary sources and were fed at the 10% level for 19 days, feeding fats with shorter chain fatty acids caused a lower enzyme activity compared to those with longer chain fatty acids. The activity was also regulated by the degree of unsaturation of dietary fats; when safflower oil, camellia oil or tristearin were fed at the 10% level for 18 days, the higher the unsaturation, the lower the activity. When trimyristin or tripalmitin were fed at the 10% level for 14 days, addition of essential fatty acid, at the level of minimum daily requirement (1% was replaced by safflower oil), did not affect the enzyme activity. Through the rate of incorporation of mevalonate into cholesterol in the 12,500 x g supernatant fraction of the liver was also found to be influenced by the types of dietary fats, the extent of the response appeared much smaller than that of HMG-CoA reductase. No consistent correlation between the HMG-CoA reductase activity and the content of microsomal cholesterol or cholesteryl ester and the fatty acid composition of microsomal lipids was observed.
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The effects of sesamin, a lignan from sesame oil, on various aspects of cholesterol metabolism were examined in rats maintained on various dietary regimens. When given at a dietary level of 0.5% for 4 weeks, sesamin reduced the concentration of serum and liver cholesterol significantly irrespective of the presence or absence of cholesterol in the diet, except for one experiment in which the purified diet free of cholesterol was given. On feeding sesamin, there was a decrease in lymphatic absorption of cholesterol accompanying an increase in fecal excretion of neutral, but not acidic, steroids, particularly when the cholesterol-enriched diet was given. Sesamin inhibited micellar solubility of cholesterol, but not bile acids, whereas it neither bound taurocholate nor affected the absorption of fatty acids. Only a marginal proportion (ca. 0.15%) of sesamin administered intragastrically was recovered in the lymph. There was a significant reduction in the activity of liver microsomal 3-hydroxy-3-methylglutaryl coenzyme A reductase after feeding sesamin, although the activity of hepatic cholesterol 7 alpha-hydroxylase, drug metabolizing enzymes, and alcohol dehydrogenase remained uninfluenced. Although the weight and phospholipid concentration of the liver increased unequivocally on feeding sesamin, the histological examination by microscopy showed no abnormality, and the activity of serum GOT and GPT remained unchanged. Since sesamin lowered both serum and liver cholesterol levels by inhibiting absorption and synthesis of cholesterol simultaneously, it deserves further study as a possible hypocholesterolemic agent of natural origin.
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The activities of hepatic fatty acid oxidation enzymes in rats fed perilla oil rich in alpha-linolenic acid (alpha-18:3) were compared with those fed saturated fats or safflower oil (the mixture of safflower oil and olive oil, 94:8, w/w) containing the same amount of polyunsaturated fatty acids with perilla oil exclusively as linoleic acid (18:2). When the rats were fed the diets containing 15% coconut, safflower, and perilla oils for 1 week, the rate of mitochondrial and peroxisomal oxidation of palmitoyl-CoA (16:0-CoA) in the liver homogenates was the highest in rats fed perilla oil. Among the rats fed the diets containing 15% palm, safflower, and perilla oils for 2 weeks, the rates of mitochondrial and peroxisomal oxidations of 16:0-, 18:2-, and alpha-18:3-CoAs were the highest in rats fed perilla oil, and the rate of oxidation of alpha-18:3-CoA by both pathways was higher than those of other acyl-CoAs in all groups. Dietary perilla oil relative to palm and safflower oils significantly increased the activities of carnitine palmitoyltransferase, acyl-CoA dehydrogenase, acyl-CoA oxidase, and 2,4-dienoyl-CoA reductase. The substrate specificity of carnitine palmitoyltransferase appeared to be responsible for differential rates of the mitochondrial oxidation of acyl-CoAs. The substrate specificity of acyl-CoA oxidase did not account for the preferential peroxisomal oxidation of alpha-18:3 relative to 18:2. The preferential mitochondrial and peroxisomal beta-oxidation of alpha-18:3-CoA relative to 16:0- and 18:2-CoAs was also confirmed in rats fed laboratory chow irrespective of the substrate/albumin ratios in the assay mixture. It was suggested that both substrate specificities and alterations in the activities of the enzymes in beta-oxidation pathway play a significant role in the regulation of the serum lipid concentrations in rats fed a diet rich in alpha-18:3.
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Peroxisome proliferator-activated receptor alpha (PPARalpha) is a member of the steroid/nuclear receptor superfamily and mediates the biological and toxicological effects of peroxisome proliferators. To determine the physiological role of PPARalpha in fatty acid metabolism, levels of peroxisomal and mitochondrial fatty acid metabolizing enzymes were determined in the PPARalpha null mouse. Constitutive liver beta-oxidation of the long chain fatty acid, palmitic acid, was lower in the PPARalpha null mice as compared with wild type mice, indicating defective mitochondrial fatty acid catabolism. In contrast, constitutive oxidation of the very long chain fatty acid, lignoceric acid, was not different between wild type and PPARalpha null mice, suggesting that constitutive expression of enzymes involved in peroxisomal beta-oxidation is independent of PPARalpha. Indeed, the PPARalpha null mice had normal levels of the peroxisomal acyl-CoA oxidase, bifunctional protein (hydratase + 3-hydroxyacyl-CoA dehydrogenase), and thiolase but lower constitutive expression of the D-type bifunctional protein (hydratase + 3-hydroxyacyl-CoA dehydrogenase). Several mitochondrial fatty acid metabolizing enzymes including very long chain acyl-CoA dehydrogenase, long chain acyl-CoA dehydrogenase, short chain-specific 3-ketoacyl-CoA thiolase, and long chain acyl-CoA synthetase are also expressed at lower levels in the untreated PPARalpha null mice, whereas other fatty acid metabolizing enzymes were not different between the untreated null mice and wild type mice. A lower constitutive expression of mRNAs encoding these enzymes was also found, suggesting that the effect was due to altered gene expression. In wild type mice, both peroxisomal and mitochondrial enzymes were induced by the peroxisome proliferator Wy-14,643; induction was not observed in the PPARalpha null animals. These data indicate that PPARalpha modulates constitutive expression of genes encoding several mitochondrial fatty acid-catabolizing enzymes in addition to mediating inducible mitochondrial and peroxisomal fatty acid beta-oxidation, thus establishing a role for the receptor in fatty acid homeostasis.
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Dietary polyunsaturated fatty acids (PUFA) are negative regulators of hepatic lipogenesis that exert their effects primarily at the level of transcription. Sterol regulatory element-binding proteins (SREBPs) are transcription factors responsible for the regulation of cholesterol, fatty acid, and triglyceride synthesis. In particular, SREBP-1 is known to play a crucial role in the regulation of lipogenic gene expression in the liver. To explore the possible involvement of SREBP-1 in the suppression of hepatic lipogenesis by PUFA, we challenged wild-type mice and transgenic mice overexpressing a mature form of SREBP-1 in the liver with dietary PUFA. In the liver of wild-type mice, dietary PUFA drastically decreased the mature, cleaved form of SREBP-1 protein in the nucleus, whereas the precursor, uncleaved form in the membranes was not suppressed. The decreases in mature SREBP-1 paralleled those in mRNAs for lipogenic enzymes such as fatty acid synthase and acetyl-CoA carboxylase. In the transgenic mice, dietary PUFA did not reduce the amount of transgenic SREBP-1 protein, excluding the possibility that PUFA accelerated the degradation of mature SREBP-1. The resulting sustained expression of mature SREBP-1 almost completely canceled the suppression of lipogenic gene expression by PUFA in the SREBP-1 transgenic mice. These results demonstrate that the suppressive effect of PUFA on lipogenic enzyme genes in the liver is caused by a decrease in the mature form of SREBP-1 protein, which is presumably due to the reduced cleavage of SREBP-1 precursor protein.
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The chapter describes the preparation of citrate lyase from Klebsiella aerogenes (Aerobacter aerogenes). The purified enzyme is activated by a range of divalent metal ions (Mg⁺⁺, Mn⁺⁺, Fe⁺⁺, and Zn⁺⁺), shows optimal activity at pH 8.0-9.0, and is powerfully inhibited by oxaloacetate. The keto form of this compound is a substrate for the enzyme, but the enol form is not and may be responsible for the inhibition observed. The spectrophotometric assay of citrate lyase is based on measurement of oxaloacetate accumulation. The method has been modified by using triethanolamine-hydrochloric acid buffer which does not form complexes with magnesium. Klebsiella aerogenes, NCIB 418 (British), are grown without aeration at 37° in 10 liter flasks filled to the neck with medium of the following composition: 9 trisodium citrate.2H2O; 2KH2PO4; 1(NH4)2SO4; 0.4 MgSO4.7H20; and adjusted to pH 7.0 with sodium hydroxide. The cells may alternatively be disrupted by sonic vibration.
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The chapter discusses three different methods by which ATP citrate lyase is assayed by determining the amount of acetyl-CoA or oxaloacetate formed. These methods are: The hydroxamate method: The acetyl-CoA formed is trapped as acetylhydroxamate and the latter is determined by the color produced with FeCl3. The spectrophotometric method: The oxaloacetate formed is measured by its reaction with NADH in the presence of malate dehydrogenase. The isotopic method: Citrate-l, 5-14C is incubated with ATP, CoA, Mg++, and enzyme, and the oxaloacetate-14C formed is degraded according to the method of Krebs and Eggleston. The 14CO2 evolved is trapped and counted. The enzyme is highly specific for citrate. The activity of this enzyme depends on the presence of Mg++. Mn++ can partially substitute for Mg++ but Ni++ Fe++, Fe3++, Cu++, and Zn++ are all inactive. The enzyme requires sulfhydryl compounds for maximal activity. 2-Mercaptoethanol, cysteine, glutathione, and dithiothreitol are all nearly equally effective. The spectrophotometric method is used in the subsequent steps of purification. Because of its high sensitivity, the isotopic method is employed when the ATP citrate lyase activity in some tissue is low.
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1. Effects of sesamin and episesamin (an epimer of sesamin) on lipid metabolism, in particular cholesterol metabolism, were examined in normocholesterolaemic and hypercholestero-laemic stroke-prone spontaneously hypertensive rats (SHRSP). 2. In normocholesterolaemic SHRSP fed a regular diet, both sesamin and episesamin significantly increased the concentration of serum total cholesterol, which was due to an increase of high density lipoprotein (HDL) subfraction rich in apoE (apoE-HDL). In addition, both substances effectively decreased serum very low density lipoprotein (VLDL). In the liver, only episesamin significantly decreased the activity of microsomal acyl-CoA: cholesterol acyltransferase. 3. In hypercholesterolaemic SHRSP fed a high-fat and high-cholesterol diet (HFC diet), only episesamin improved serum lipoprotein metabolism with an increase in apoA-I and a decrease in apoB. In the liver, both sesamin and episesamin significantly suppressed cholesterol accumulation. Interestingly, only episesamin significantly increased the activity of microsomal cholesterol 7α-hydroxylase. 4. These results indicate that sesamin may be effective in preventing cholesterol accumulation in the liver. In comparison with sesamin, episesamin may be effective in the regulation of cholesterol metabolism in the serum and liver.
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The effect of clofibrate on the production of ketone bodies and the secretion of lipids was examined in the isolated rat liver. Feeding of clofibrate (0.3% in the diet) for a week caused the liver enlargement. The drug increased ketone body production and conversely decreased the secretion of triglyceride and cholesterol in the perfused liver, in particular when oleate was provided to the perfusion medium. Fractionation of the liver perfusate at the density of 1.006 g/ml showed that changes in the rate of lipid secretion were largely due to the modification of the rate of very low density lipoprotein secretion. These observations indicated that the enhancement of fatty acid oxidation by clofibrate resulted in the concomitant decrease in the flux of free fatty acid into triglyceride synthesis and subsequent formation and secretion of triglyceride-rich lipoproteins in the liver. Measurement of activities of enzymes involved in hepatic cholesterogenesis proved that the alteration of the rate of hepatic cholesterogenesis might not be a factor responsible for the hypocholesterolemic action of clofibrate.
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The effect of dietary soybean phospholipid on the activities of hepatic triacylglycerol-synthesizing enzymes was compared with soybean oil in fasted-refed rats. Soybean oil at the dietary level corresponding to 20% but not at 5% fatty acid level (21.2 and 5.3% on weight bases, respectively) significantly decreased liver microsomal diacylglycerol acyltransferase activities measured with the endogenous diacylglycerol substrate. Dietary soybean phospholipid even at the dietary level corresponding to 2% fatty acids (3.4% on weight base) significantly decreased the acyltransferase activities measured with endogenous substrate. The dietary phospholipid further decreased the parameter as the dietary level increased, and at the 5% fatty acid level, it was lower than that obtained with soybean oil at 20% fatty acid level. Soybean oil and phospholipid decreased the diacylglycerol acyltransferase activities measured with the saturating concentration of exogenous dioleoylglycerol substrate only when the activities were expressed in terms of total activity (mumol/min per liver) but to much lesser extents. Dietary phospholipid compared to the oil profoundly decreased not only hepatic triacylglycerol but also microsomal diacylglycerol levels. It was indicated that the availability of microsomal diacylglycerol as the substrate for diacylglycerol transferase is the critical determinant in regulating hepatic triacylglycerol synthesis and concentration in this experimental situation. Alterations in the activities of microsomal glycerol 3-phosphate acyltransferase and of the enzymes in fatty acid synthesis could account for the phospholipid-dependent decrease in the microsomal concentration of this intermediate in triacylglycerol synthesis.
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The effects of dietary supplementation of sesamin on 7,12-dimethylbenz[a]anthracene (DMBA)-induced mammary carcinogenesis in female Sprague-Dawley rats were studied. Experimental diets containing 0.2% sesamin (an equiweight mixture of sesamin and episesamin) or 0.2% alpha-tocopheryl acetate were given to rats starting 1 week before intragastric administration of DMBA (10 mg/rat). Sesamin significantly (p less than 0.05) reduced the cumulative number of palpable mammary cancers by 36% at 12 weeks post-DMBA administration compared with animals on a control diet. Alpha-tocopheryl acetate inhibited both the incidence and the cumulative number of mammary tumors by 20% and 45%, respectively. Concentrations of lipid peroxides in plasma, liver and tumors were all decreased in both sesamin and alpha-tocopheryl acetate groups. The activity of peripheral blood mononuclear cells (PBMC) increased in rats fed sesamin (140 to 150% of the control and alpha-tocopheryl acetate groups). Fatty acid compositions of plasma, liver and tumor phosphatidylcholine showed a decreased tendency of the metabolism of linoleic acid to arachidonic acid and hence of the plasma concentration of prostaglandin E2 in the sesamin group. The inhibitory effect of sesamin on DMBA-induced mammary carcinogenesis may be ascribed, at least in part, to immunopotentiation and increased antioxidative activity.
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Vitamin E activity of sesame seed, which contains only gamma-tocopherol, a compound that has vitamin E activity equal to only 6-16% that of alpha-tocopherol, was examined in two experiments. In the first experiment, groups of rats were fed four diets: vitamin E-free control diet, alpha-tocopherol-containing diet, gamma-tocopherol-containing diet and sesame seed-containing diet. Changes in red blood cell hemolysis, plasma pyruvate kinase activity, and peroxides in plasma and liver, as indices of vitamin E activity, were examined. The sesame seed diet has high vitamin E activity, whereas this activity was low in the gamma-tocopherol diet. In plasma and liver, alpha-tocopherol was found in high concentration only in the alpha-tocopherol-fed group, and gamma-tocopherol was found in high concentration only in the sesame seed-fed group, with negligible amounts of gamma-tocopherol in liver of the gamma-tocopherol-fed group. In the second experiment, two diets containing sesame lignan (sesaminol or sesamin) and gamma-tocopherol were tested. Results in both of the sesame lignan-fed groups were comparable to those observed in the sesame seed-fed group in Experiment 1. These experiments indicate that gamma-tocopherol in sesame seed exerts vitamin E activity equal to that of alpha-tocopherol through a synergistic interaction with sesame seed lignans.
Article
Effects of soybean protein, casein and whole egg protein on various indices for lipid biosynthesis in the liver were compared in fasted-refed rats. Soybean protein compared to casein and whole egg protein significantly reduced activities of glucose 6-phosphate dehydrogenase and fatty acid synthetase. The protein source also slightly reduced the activity of the malic enzyme. Soybean protein compared to other proteins not only reduced the microsomal triacylglycerol but also phosphatidylcholine syntheses when the activities were measured with endogenous diacylglycerol substrate. The protein-dependent changes disappeared, if artificial dispersion of dioleoylglycerol was employed as a substrate. The concentrations of microsomal diacylglycerol and triacylglycerol in whole liver in rats fed soybean protein were lower than those fed other proteins. When the diets containing soybean protein and casein were supplemented with DL-methionine (0.5 and 0.3%, respectively) to meet the nutritional requirement of the animals, soybean protein-dependent reductions in these indices for lipid biosynthesis were still detectable but considerably attenuated. Thus, it is plausible that a soybean protein-dependent decrease in fatty acid synthesis reduced the availability of microsomal diacylglycerol substrate for triacylglycerol synthesis and in turn modified hepatic triacylglycerol concentration. The dietary availability of sulfur amino acids may, at least in part, be responsible for the consequence observed in the present study.
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We have cloned a member of the steroid hormone receptor superfamily of ligand-activated transcription factors. The receptor homologue is activated by a diverse class of rodent hepatocarcinogens that causes proliferation of peroxisomes. Identification of a peroxisome proliferator-activated receptor should help elucidate the mechanism of the hypolipidaemic effect of these hepatocarcinogens and aid evaluation of their potential carcinogenic risk to man.
Article
The quantitative relationship between fatty acid synthesis de novo and production of plasma lipoproteins by perfused liver has been investigated. Livers of rats were perfused in situ for 3–5 hours with a suspension of erythrocytes in one of three perfusing media: rat plasma, buffer containing albumin, or a mixture of plasma and buffer. Tritium oxide (2 mC) was added in each case. Livers were from young rats fed adlibitum or fasted and re-fed. Rates of hepatic fatty acid synthesis ranged from 1.4 to 14.1 μmoles/gm liver/hour, as determined from the tritium content of fatty acids in the liver plus perfusate. A high correlation was found between the number of micromoles of fatty acid synthesized by livers and the number of micromoles of esterified fatty acid released by livers into the perfusing medium. When the perfusate was prepared with only plasma, 0.9 mole of total fatty acid was released per mole synthesized. With all perfusing media, net release of triglycerides, and to a lesser extent cholesterol, was highly correlated with rate of fatty acid synthesis. The additional amounts of triglycerides and cholesterol resulting from accelerated fatty acid synthesis were all released into the perfusate β-lipoprotein fraction, identified immunochemically and by ultracentrifugation. Livers with similar rates of fatty acid synthesis released more triglyceride, cholesterol, and newly synthesized fatty acid when the perfusing medium contained plasma. Net release of phospholipids was nearly independent of the rate of fatty acid synthesis or the presence of plasma in the perfusate. The rate of fatty acid synthesis de novo, which varied widely among even carefully selected rats, is an important determinant of lipid release by the perfused liver.
Article
We investigated the antihypertensive effect of sesamin, a lignan from sesame oil, using deoxycorticosterone acetate (DOCA)-salt hypertensive rats. The animals were unilaterally nephrectomized, and then separated into a sham-operated group (sham group) and a DOCA-salt-treated group. The latter was further separated into a normal diet group (control group) and a sesamin-containing diet group (sesamin group). The systolic blood pressure of control group progressively increased in comparison with that of sham group. This DOCA-salt-induced hypertension was markedly suppressed by feeding a sesamin-containing diet. Systolic blood pressure after 5 weeks was 130.6 +/- 1.9 mmHg in the sham group, 198.1 +/- 7.3 mmHg in the control group and 152.5 +/- 8.4 mmHg in the sesamin group, respectively. The treatment with DOCA and salt for 5 weeks significantly increased the weight of the left ventricle plus the septum. However, this increase was significantly suppressed in the sesamin group. When the degree of vascular hypertrophy of the aorta and superior mesenteric artery was histochemically evaluated, there were significant increases in wall thickness, wall area and the wall-to-lumen ratio in the control group, compared with the sham. Sesamin feeding ameliorated the development of DOCA-salt-induced vascular hypertrophy in both the aorta and mesenteric artery. These findings strongly suggest that sesamin is useful as a prophylactic treatment in the development of hypertension and cardiovascular hypertrophy.
Article
The natriuretic peptide family consists of three endogenous ligands; atrial natriuretic peptide (ANP), brain natriuretic peptide (BNP) and C-type natriuretic peptide (CNP), and is involved in the regulation of cardiovascular homeostasis. Both ANP and BNP act mainly as cardiac hormones and are produced predominantly by the atrium and ventricle, respectively. Expression of the BNP and ANP genes is greatly augmented in patients with congestive heart failure and animal models of ventricular hypertrophy or cardiomyopathy. In the heart, the BNP gene expression is regulated differently from the ANP gene expression both at transcriptional and post-transcriptional levels. Transgenic technology has provided the direct evidence that BNP as well as ANP is involved in the chronic blood pressure control. Contrasting with ANP and BNP, CNP does not act as a cardiac hormone but as a neuropeptide or an endothelium-derived autocrine/paracrine regulator. Endothelial production of CNP is remarkably augmented by various cytokines and growth factors such as transforming growth factor-beta and tumour necrosis factor-alpha, suggesting the pathophysiological significance of CNP in the process of various vascular disorders. Chromosomal mapping of natriuretic peptides has revealed that the CNP gene is localized on mouse chromosome 1, while ANP and BNP are tightly linked on mouse chromosome 4, suggesting that CNP, a local regulator, is functionally and evolutionarily distinct from ANP and BNP, both of which are cardiac hormones. Understanding the molecular biology and biochemistry of the natriuretic peptide family will lead to the better understanding of its physiological and pathophysiological implication, and the clinical application in cardiorenal regulation.
Article
The effects of sesamin, a potent inhibitor of delta 5-desaturase in polyunsaturated fatty acid biosynthesis, on the fatty acid compositions of tissue lipids and liver functions were examined in rodents. When a mixture of sesamin and episesamin (51.1:48.2, w/w) was given to rats at a dietary level of 0.5% for 13 days, the proportions of dihomo-gamma-linolenic acid significantly increased not only in the liver but also in plasma and hemocytes, suggesting an interference with delta 5-desaturation by these lignans. The sesamin preparation at the dietary level of 1% improved changes in various blood parameters of the mouse, such as aspartate aminotransferase and alanine aminotransferase activities, and the concentrations of total cholesterol, triglyceride and total bilirubin, caused by continuous inhalation of ethanol. In addition, sesamin showed a significant protective effect against the accumulation of fat droplets and vacuolar degeneration in the mouse liver, as confirmed on histological examination. Sesamin, at the level of 100 mg/kg body weight, also tended to prevent liver lipid accumulation by carbon tetrachloride in mice. These results indicate that sesamin and a related lignan compound have an ability to improve liver function.
Article
Peroxisome proliferators induce thyroid-hormone-dependent liver activities, e.g. 'malic' enzyme, mitochondrial glycerol-3-phosphate dehydrogenase, glucose-6-phosphate dehydrogenase, S14[Hertz, Aurbach, Hashimoto and Bar-Tana (1991) Biochem. J. 274, 745-751]. Here we report that the thyromimetic effect of peroxisome proliferators with respect to 'malic' enzyme result from transcriptional activation of the 'malic' enzyme gene, mediated by binding of the peroxisome proliferator activated receptor (PPAR alpha)/retinoid X receptor (RXR alpha) heterodimer to a 5'-flanking enhancer of the 'malic' enzyme promoter. The enhancer involved is distinct from the thyroid hormone response element of the 'malic' enzyme promoter and is partly homologous with that which mediates transcriptional activation of peroxisomal acyl-CoA oxidase by peroxisome proliferators. Hence transcriptional activation of thyroid-hormone-dependent liver genes by xenobiotic or endogenous amphipathic carboxylates collectively defined as peroxisome proliferators is mediated by a transduction pathway similar to that involved in transcriptional activation of peroxisomal beta-oxidative genes and distinct from that which mediates thyroid hormone action.
The activity of hepatic fatty acid oxidation enzymes in rats fed linseed and perilla oils rich in alpha-linolenic acid (alpha-18:3) was compared to that in rats fed safflower oil rich in linoleic acid (18:2) and a saturated fat (palm oil). Palm and safflower oils were essentially devoid of alpha-18:3. The palmitoyl-CoA oxidation rates both in mitochondrial and peroxisomal pathways in liver homogenates were significantly higher in rats fed linseed oil than in those fed palm and safflower oils. Among rats fed diets containing palm oil, safflower oil, fat mixtures composed of safflower and perilla oils (2:1, w/w and 1:2, w/w), and perilla oil, mitochondrial and peroxisomal fatty oxidation rates increased with increasing dietary levels of perilla oil. Compared to palm and safflower oils, dietary alpha-18:3 either in the form of linseed or perilla oils profoundly increased the activity of carnitine palmitoyltransferase, acyl-CoA oxidase, 3-ketoacyl-CoA thiolase, and 2,4-dienoyl-CoA reductase. Smaller but significant increases by dietary alpha-18:3 of the activity of acyl-CoA dehydrogenase, enoyl-CoA hydratase, and delta 3, delta 2-enoyl-CoA isomerase were also observed. Unexpectedly, dietary alpha-18:3 greatly reduced the activity of 3-hydroxy-acyl-CoA dehydrogenase. Compared to palm oil, dietary polyunsaturated fats significantly reduced the activity of fatty acid synthetase and glucose-6-phosphate dehydrogenase to the same levels. The activity of pyruvate kinase was significantly higher in rats fed palm oil than in those fed polyunsaturated fats. The extent of reduction was more prominent with polyunsaturated fats containing alpha-18:3 than with safflower oil devoid of alpha-18:3. Thus, compared to linoleic acid and saturated fatty acids, dietary alpha-18:3 caused characteristic changes in the activity of hepatic enzymes in fatty acid and glucose metabolism in rats.
1. Effects of sesamin and episesamin (an epimer of sesamin) on lipid metabolism, in particular cholesterol metabolism, were examined in normocholesterolaemic and hypercholesterolaemic stroke-prone spontaneously hypertensive rats (SHRSP). 2. In normocholesterolaemic SHRSP fed a regular diet, both sesamin and episesamin significantly increased the concentration of serum total cholesterol, which was due to an increase of high density lipoprotein (HDL) subfraction rich in apoE (apoE-HDL). In addition, both substances effectively decreased serum very low density lipoprotein (VLDL). In the liver, only episesamin significantly decreased the activity of microsomal acyl-CoA:cholesterol acyltransferase. 3. In hypercholesterolaemic SHRSP fed a high-fat and high-cholesterol diet (HFC diet), only episesamin improved serum lipoprotein metabolism with an increase in apoA-I and a decrease in apoB. In the liver, both sesamin and episesamin significantly suppressed cholesterol accumulation. Interestingly, only episesamin significantly increased the activity of microsomal cholesterol 7alpha-hydroxylase. 4. These results indicate that sesamin may be effective in preventing cholesterol accumulation in the liver. In comparison with sesamin, episesamin may be effective in the regulation of cholesterol metabolism in the serum and liver.
Article
Although the sesame lignans, sesaminol and sesamolinol, have been shown to possess antioxidative activity, less is known about the metabolism and antioxidative properties of sesamolin, a major constituent of sesame oil. To determine the ability of sesamolin to act as an antioxidant in vivo, we fed rats a diet containing 1% sesamolin for 2 wk and studied its metabolism and its effects on oxidative stress. About 75% of the ingested sesamolin was excreted unmetabolized in feces, but it was not detected in urine. Sesamolin and its metabolites, sesamol and sesamolinol, were excreted primarily as sulfates and glucuronides. The amount of sesamolin and its metabolites was lower in the plasma than in the liver or kidneys. When we compared rats fed a diet containing 1% sesamolin for 14 d with those fed a control diet, we found that liver weight was significantly greater in the former group. Lipid peroxidation activity, measured as 2-thiobarbituric acid reactive substances, was significantly lower in the kidneys and liver of the sesamolin-fed rats than in the controls. In addition, the amount of 8-hydroxy-2'-deoxyguanosine excreted in the urine was significantly lower in the sesamolin-fed rats. These results suggest that sesamolin and its metabolites may contribute to the antioxidative properties of sesame seeds and oil and support our hypothesis that sesame lignans reduce susceptibility to oxidative stress.
Article
The antihypertensive effect of sesamin, a lignan from sesame oil, was examined using salt-loaded and unloaded stroke-prone spontaneously hypertensive rats (SHRSP). The animals at 6 weeks of age were separated into a salt-loaded group and an unloaded group. Salt-loaded animals were maintained on 1% NaCl drinking water. Each group was further divided into two groups: normal-diet group and sesamin-diet group. Systolic blood pressure of all animals was monitored once weekly. At the end of the feeding periods, cardiovascular hypertrophy and renal damage were evaluated. In the salt-loaded group, sesamin feeding significantly suppressed the development of hypertension, and efficient suppression was maintained from 9 to 26 weeks (e.g., 215+/-4 vs. 180+/-4 mmHg, at 17 weeks old). The left ventricle plus septum weight-to-body weight ratio was slightly but significantly lowered by sesamin feeding. When the degree of vascular hypertrophy of the aorta and superior mesenteric artery was histochemically evaluated, wall thickness and wall area of these vessels were significantly decreased by the sesamin feeding. Histological renal damage such as thickening of the tunica intima and fibrinoid degeneration of the arterial wall were often observed in the normal-diet group, but this damage was efficiently reduced in the sesamin-fed animals. On the other hand, in the salt-unloaded group, only a slight and nonsignificant suppressive effect of sesamin on the development of hypertension was observed. Although the wall area of the aorta was significantly decreased by the sesamin feeding, other vascular parameters were not ameliorated. The incidence of histological renal damage tended to decrease in sesamin-fed animals, but these alterations were not statistically significant. Thus, sesamin feeding was much more effective as an antihypertensive regimen in salt-loaded SHRSP than in unloaded SHRSP, thereby suggesting that sesamin is more useful as a prophylactic treatment in the malignant status of hypertension and/or hypertension followed by water and salt retention.
Article
The effects of sesamin, one of the most abundant lignans in sesame seed, on hepatic fatty acid oxidation were examined in rats that were fed experimental diets containing various amounts (0%, 0.1%, 0.2%, and 0.5%) of sesamin (a 1:1 mixture of sesamin and episesamin) for 15 days. Dietary sesamin dose-dependently increased both mitochondrial and peroxisomal palmitoyl-coenzyme A (CoA) oxidation rates. Mitochondrial activity almost doubled in rats on the 0.5% sesamin diet. Peroxisomal activity increased more than 10-fold in rats fed a 0.5% sesamin diet in relation to rats on the sesamin-free diet. Dietary sesamin greatly increased the hepatic activity of fatty acid oxidation enzymes, including carnitine palmitoyltransferase, acyl-CoA dehydrogenase, acyl-CoA oxidase, 3-hydroxyacyl-CoA dehydrogenase, enoyl-CoA hydratase, and 3-ketoacyl-CoA thiolase. Dietary sesamin also increased the activity of 2,4-dienoyl-CoA reductase and delta3,delta2-enoyl-CoA isomerase, enzymes involved in the auxiliary pathway for beta-oxidation of unsaturated fatty acids dose-dependently. Examination of hepatic mRNA levels using specific cDNA probes showed a sesamin-induced increase in the gene expression of mitochondrial and peroxisomal fatty acid oxidation enzymes. Among these various enzymes, peroxisomal acyl-CoA oxidase and bifunctional enzyme gene expression were affected most by dietary sesamin (15- and 50-fold increase by the 0.5% dietary level). Sesamin-induced alterations in the activity and gene expression of carnitine palmitoyltransferase I and acyl-CoA oxidase were in parallel with changes in the mitochondrial and peroxisomal palmitoyl-CoA oxidation rate, respectively. In contrast, dietary sesamin decreased the hepatic activity and mRNA abundance of fatty acid synthase and pyruvate kinase, the lipogenic enzymes. However, this lignan increased the activity and gene expression of malic enzyme, another lipogenic enzyme. An alteration in hepatic fatty acid metabolism may therefore account for the serum lipid-lowering effect of sesamin in the rat.
Article
Convenient syntheses were developed to obtain on a multigram scale the novel taste enhancer N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol 1, called alapyridaine, as a racemic mixture and as pure (+)-(S) and (-)-(R) enantiomers, respectively. 5-(Hydroxymethyl)-2-furaldehyde was used as key intermediate and was reacted with l-alanine under alkaline conditions to obtain racemic 1. Alternatively, reductive amination of 5-(hydroxymethyl)-2-furaldehyde with Raney-Ni/hydrogen and l- or d-alanine followed by mild oxidation led to (+)-(S)-1 and (-)-(R)-1, respectively. Racemization was promoted under alkaline and boiling conditions via a carbanion, the formation of which was facilitated by the electron-withdrawing effect of the iminium cation and the resonance-stabilizing capacity of the pyridinium moiety. Under these conditions, 1 was obtained in a 1:1 mixture of the phenol (1) and phenolate (1-H) forms as shown by X-ray diffraction. Racemic 1 formed monoclinic crystals of high molecular organization in which the phenol-type (RS)-1, the phenolate-type (RS)-1-H, sodium cations, and ethanol molecules are present. The crystal structure of [Na(1)(1-H).(C(2)H(6)O)] shows one-dimensional mu(2)-bridging-oxygen polymers stabilized by a three-dimensional network of ionic, hydrogen bond, and pi-stacking interactions with channels occupied by solvent molecules.
Article
Adulteration of vegetable oil is of concern for both commercial and health reasons. Compositional based fingerprints can potentially reveal both the oil source and its possible adulteration. Here, electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) resolves and identifies literally thousands of distinct chemical components of commercial canola, olive, and soybean oils, without extraction or other wet chemical separation pretreatment. In negative-ion ESI FT-ICR MS, the acidic components of soybean oil are easily distinguished from those of canola and olive oil based on relative abundances of C(18) fatty acids, whereas olive oil differs from canola and soybean oil based on relative abundances of tocopherols. In positive-ion ESI FT-ICR MS, the three oils are readily distinguished according to the relative abundances of di- and triacylglycerols with various numbers of double bonds in the fatty acid chains. We demonstrate the detection of soybean oil as an adulterant of olive oil, based on relative abundances of members of each of several chemical families. We suggest that the detailed chemical compositions of vegetable oils can be used to characterize them and to detect and identify adulterants.
New sesame line having high lignan content in seed and its functional activity 2), 184. (12) Resources Council, Science and Technology Agency of Japan. In Standard Tables of Food Composition in Japan, 4th revised ed.; Bureau of Engraving and Print-ing
  • M Katsuta
Katsuta, M. New sesame line having high lignan content in seed and its functional activity. Breed. Res. 2000, 2 (Suppl. 2), 184. (12) Resources Council, Science and Technology Agency of Japan. In Standard Tables of Food Composition in Japan, 4th revised ed.; Bureau of Engraving and Print-ing, Ministry of Finance of Japan: Tokyo, Japan, 1982; pp 91-92.
DOI: 10.1021/jf070242j) It is essential that novel compounds, either synthetic or isolated from natural sources, be characterized rigorously and unequivocally. Supporting data normally include physical form, melting point (if solid
  • Agric
  • Chem
Agric. Food Chem. 2007, 55, 4625–4629 (DOI: 10.1021/jf070242j). It is essential that novel compounds, either synthetic or isolated from natural sources, be characterized rigorously and unequivocally. Supporting data normally include physical form, melting point (if solid), UV/IR spectra if appropriate, 1 H and 13 C NMR, mass spectrometric data, and optical rotation (when compounds have chiral centers).
For a discussion of the Journal's expectations for compound characterization, please read Compound Identification: A Journal of Agricultural and Food Chemistry Perspective
  • Novel Compound Characterization
Novel Compound Characterization. For a discussion of the Journal's expectations for compound characterization, please read " Compound Identification: A Journal of Agricultural and Food Chemistry Perspective " by R. J. Molyneux and P. Schieberle. J.
Analysis of Polyphenolic Antioxidants from the Fruits of Three Pouteria Species by Selected Ion Monitoring Liquid Chromatography–Mass Spectrometry
  • Hplc / Ms Reporting Liquid Chromatography ( Hplc )
  • Ma
Reporting liquid chromatography (HPLC) and HPLC/MS: " Analysis of Polyphenolic Antioxidants from the Fruits of Three Pouteria Species by Selected Ion Monitoring Liquid Chromatography–Mass Spectrometry ", by Jun Ma et al. J. Agric. Food Chem. 2004, 52, 5873–5878.