Sesaminol Diglucoside Research Articles

Optimizing conditions for the recovery of lignans from sesame cake using three green extraction methods: Microwave-, ultrasound- and accelerated-assisted solvent extraction

Lignans, a group of polyphenolic low molecular weight bioactive compounds with health benefits, are major constituents of sesame cake (SC), a by-product derived from sesame oil processing. The utilization of this by-product in the food or nutraceutical industries could explore its valorization route in compliance with sustainability and circular economy principles. This study aimed to investigate the impact of different environmental-friendly processing approaches such as ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE) and accelerated solvent extraction (ASE) for lignans extraction from SC using central composite design (CCD) with response surface methodology (RSM). Sesaminol triglucoside (SETRI) and sesaminol diglucoside (SEDI) were identified and quantified as the major lignan glucosides in SC. Ethanol/water mixture was selected as ‘green’ solvent for all extraction methods. The influence of ethanol concentration (X1), extraction time (X2), temperature (X3) and solid-to-solvent (SS) ratio or solid weight (X4) on extraction yield (EY), SETRI and SEDI contents for each technique was examined. The developed models exhibited a high degree of desirability (> 0.72) with determined optimal levels of extraction parameters as follows: X1 = 71%, X2 = 10 min, X3 = 50 °C, X4 = 1.50 g/20 mL for UAE; X1 = 80%, X2 = 5 min, X3 = 50 °C, X4 = 0.85 g/20 mL for MAE; X1 = 80%, X2 = 20 min, X3 = 65 °C, X4 = 2 g for ASE. Under these optimal conditions, the experimental values for EY, SETRI and SEDI contents in SC extracts were: 8.28%, 105.98 mg/g and 16.93 mg/g, respectively for UAE; 8.75%, 105.41 mg/g and 18.76 mg/g, respectively for MAE; 9.34%, 108.00 mg/g and 18.34 mg/g, respectively for ASE. The ANOVA analysis from the RSM were fitted with quadratic models yielding acceptable R2 (> 0.87), adjusted R2 (> 0.77), predicted R2 (> 0.74), and nonsignificant lack-of-fit (p > 0.05) values. Ethanol concentration and solid-to-solvent ratio were the most influencing factors affecting lignans extraction. Although ASE was found as the most suitable method for extracting lignans from SC, from an industrial viewpoint, UAE could be a more affordable technique due to advances in ultrasonic processing devices for large scale applications.

Hypolipidemic effect of Sesame Seed Oil: A Review

Sesame seed (Sesamum indicum L) oil is an excellent source of unsaturated fatty acids and secondary metabolites. Most commonly used in Eastern countries, easily available and cheap source of essential nutrients. Objective: To identify scientific evidence regarding the hypolipidemic effect of sesame seed oil and its derivatives. Elevated levels of plasma lipids and cholesterol is known as hyperlipidemia, increased lipids levels are directly associated with vascular and metabolic disorders. Hyperlipidemia is the most common risk factor of cardiovascular diseases. Sesame seed oil is loaded in vitamin E, sesamin, sesamolin, sesamol, lignans, and phytoestrogen, these constituents have the potential to reduce hyperlipidemia, hypercholesterolemia, and elevated triglycerides levels. They also act as antioxidants to prevent lipid peroxidation and oxidative stress. The mechanism behind the hypolipidemic effect of sesame seed oil is its ability to increase superoxide dismutase SOD and glutathione peroxidase (antioxidants), reduction in triglycerides, and Malondialdehyde (MDA) concentration. MDA is the end product of lipid peroxidation and triggers lipid accumulation in blood. It has been studied that Sesaminol diglucoside helps to reduce white fat deposition by increasing the conversion of fat into brown fat. Conclusions: Results suggest that sesame seed oil is highly effective to manage hyperlipidemia and dyslipidemia due to its lipid ameliorating and anti-oxidative effect

Sesaminol diglucoside isolated from black sesame seed cake and its antioxidant, anti-collagenase and anti-hyaluronidase activities

Sesaminol diglucoside (SDG) was isolated, purified and characterized from defatted sesame seed cake, a by-product of sesame oil extraction. Its antioxidant, anti-hyaluronidase and anti-collagenase activities were investigated. SDG was successfully purified from the methanol fraction using preparative HPLC. The structure was elucidated using 1H and 13C nuclear magnetic resonance spectroscopy and compared with the reference. The in vitro antioxidant activity of SDG was measured using DPPH free radical scavenging and ferric reducing antioxidant power (FRAP) assays. The results showed that SDG was a potential DPPH free radical scavenger with an IC50 value 0.201 ± 0.002 mg/ml and also showed a strong reducing power with FRAP value of 2.18 ± 0.001 mM Fe (II)/g of extract and EC1 value of 0.54 ± 0.001 mg/ml. It also had the highest collagenase inhibition with an IC50 value of 0.26 ± 0.01 mg/ml and hyaluronidase activity of 92.6 ± 0.5% inhibition. Therefore, the SDG could be a promising antioxidant, anti-collagenase and anti-hyaluronidase that could be used for both for neutraceutical and cosmetic applications.

Free Radical Scavenging Capability of Various Defatted Sesame Seed Cakes and Hulls Using EPR Compared with In Vitro Testing and HPLC Analysis.

The free radical scavenging activities of black and white sesame seed hulls and the powder of black and white sesame seed cakes were investigated using noninvasive continuous wave electron paramagnetic resonance (EPR) and antioxidant assays. With black sesame seed hulls and the powder of black sesame seed cakes, EPR detected the very strong single-line signal intensities that correspond to the stable organic radicals, while the spectrum of the white sesame seed hulls and the white sesame seed cakes showed no signal. The in vitro antioxidant activities of black and white sesame seed cake extract were evaluated by DPPH free radical scavenging activity, hydrogen peroxide scavenging activity, and ferric reducing antioxidant power (FRAP) assay. The results indicated that the extract from black sesame seed cake possessed a greater DPPH radical inhibitory activity and hydrogen peroxide inhibitory activity than white sesame seed cake extract, with IC50 values of 0.847 ± 0.011 mg/mL and 0.338 ± 0.007 mg/mL, respectively. Black sesame seed cake extract also showed a strong reducing power with a FRAP value of 1.307 ± 0.037 mM Fe (II)/g of extract weight and an EC1 value of 0.683 ± 0.002 mg/mL. The main compounds from the black and white sesame seed cake extracts were analysed using high-performance liquid chromatography (HPLC). The results revealed that the main compounds in black and white sesame seed cake extracts were in a group of water-soluble lignans, mainly sesaminol triglucoside and sesaminol diglucoside. However, sesaminol diglucoside was found in large amounts in the black sesame seed cake extract, while it was found in a very small amount in the white sesame seed cake extract. Therefore, these results demonstrated considerable antioxidant capacity of the sesame seed, especially in the black strain.

Sesaminol diglucoside, a water-soluble lignan from sesame seeds induces brown fat thermogenesis in mice

Brown adipose tissue (BAT) is the site of non-shivering thermogenesis in mammals, wherein energy is dissipated as heat. We observed that aqueous extract of black sesame seed triggers an increase in the expression of Uncoupling Protein 1 (UCP1) in brown adipocytes from mice. The active component from the extract was purified and identified to be sesaminol diglucoside (SDG). SDG treatment decreased mass of white fat pads and serum glucose levels and increased UCP1 levels in BAT thereby protecting mice against high fat induced weight gain. Further in silico and in vitro studies revealed that these effects are due to the agonist like behaviour of SDG towards beta 3 adrenergic receptors (β3-AR). Together, our results suggest that SDG induces BAT mediated thermogenesis through β3-AR and protects mice against diet-induced obesity.

Preparation of Sesaminol from Sesaminol Triglucoside by β‐Glucosidase and Cellulase Hydrolysis

AbstractSesaminol triglucoside (i.e., 2,6‐O‐di(β‐d‐glucopyranosyl)‐β‐d‐glucopyranosyl sesaminol, STG) is a physiologically active substance obtained abundantly from defatted sesame cake. Since, the industrial preparation of sesaminol from STG has not been reported previously, the aim of this research was to prepare sesaminol by hydrolysis of STG using β‐glucosidase and cellulase. Under the optimal conditions of total enzyme dosage 100 μL (8,000.72 U), the ratio of β‐glucosidase and cellulase 20:80 (v/v) (0.72:8,000, U/U), reaction time 24 h, substrate concentration 6 mg/mL, reaction temperature 50 °C, and reaction system pH 4.8, the yield of sesaminol was 48.9 %. Further, sesaminol and other hydrolysis products (sesaminol diglucoside and sesaminol monoglucoside) were successfully determined by high performance liquid chromatography and electrospray ionization/mass spectrometry.

Optimization of phenolics extraction from sesame seed cake

Sesame seed cake is considered to be a by-product of the oil industry, being commonly used as cattle feed in several producing countries. However, this residue can be recovered and value added. The main phenolics found in sesame seed are lignans, which are important bioactive compounds of this seed. The main lignans in defatted sesame were identified as sesaminol triglucoside, sesamolinol diglucoside and sesaminol diglucoside. The objective of this study was to optimize the extraction of total phenolics and lignans from sesame seed cake. A second-order polynomial model was set up to predict the responses using response surface methodology (RSM). The independent variables analyzed were temperature (25–90°C), solid/solvent ratio (0.03–0.11g/mL) and ethanol concentration (0–95%). Response variables were the concentrations of total phenolics (TP), sesamin (SES), sesaminol triglucoside (ST) and antioxidant activity (ABTS). The extracted amount of TP ranged between 129.7 and 355.3mgGAE/100g, SES from 3.2 to 25.7mgSES/100g, ST from 208.1 to 537.5mgSE/100g and the ABTS of the extracts was between 8460 and 24311μMTE. Among the analyzed compounds, ST is presented in the highest quantity in sesame cake. Solid to liquid ratio and ethanol concentration were the most important factors affecting extraction, whereas temperature showed reduced influence. The model obtained to describe the effect of these factors on the extraction of ST was satisfactorily validated.

Nondestructive Determination of Lignans and Lignan Glycosides in Sesame Seeds by Near Infrared Reflectance Spectroscopy

Sesame (Sesamum indicum L.) contains abundant lignans including lipid-soluble lignans (sesamin and sesamolin) and water-soluble lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) related to antioxidative activity. In this study, near infrared reflectance spectroscopy (NIRS) was used to develop a rapid and nondestructive method for the determination of lignan contents on intact sesame seeds. Ninety-three intact seeds were scanned in the reflectance mode of a scanning monochromator. This scanning procedure did not require the pulverization of samples, allowing each analysis to be completed within minutes. Reference values for lignan contents were obtained by high-performance liquid chromatography analysis. Calibration equations for lignans (sesamin and sesamolin) and lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) contents were developed using modified partial least squares regression with internal cross-validation (n = 63). The equations obtained had low standard errors of cross-validation and moderate R2 (coefficient of determination in calibration). The prediction of an external validation set (n = 30) showed significant correlation between reference values and NIRS predicted values based on the SEP (standard error of prediction), bias, and r2 (coefficient of determination in prediction). The models developed in this study had relatively higher values (more than 2.0) of SD/SEP(C) for all lignans and lignan glycosides except for sesaminol diglucoside, which had a minor amount, indicating good correlation between the reference and the NIRS estimate. The results showed that NIRS, a nondestructive screening method, could be used to rapidly determine lignan and lignan glycoside contents in the breeding programs for high quality sesame.

HPLC Analysis of Sesaminol Glucosides in Sesame Seeds

An HPLC method was developed and validated for the quantification of sesaminol triglucoside and a sesaminol diglucoside in sesame seeds. These two lignans were isolated, and their structures were characterized by mass and nuclear magnetic resonance spectroscopy. Defatted sesame flour was extracted first with 85% ethanol for 5 h followed by 70% ethanol for 10 h at room temperature using naringenin as internal standard. Analysis of 65 different samples of sesame seeds indicated that the content of sesaminol triglucoside ranged from 36 to 1560 mg/100 g of seed (mean 637 +/- 312) and that of sesaminol diglucoside ranged from 0 to 493 mg/100 g of seed (mean 75 +/- 95). No significant difference was found between sesaminol glucoside contents in black and white seeds.

In vitro studies on antioxidant activity of lignans isolated from sesame cake extract

AbstractThe antioxidant activity of compounds isolated from a methanolic extract of commercial sesame cake was studied using a peroxidation model and a radical‐scavenging method. Pure compounds were isolated from the extract by preparative high‐performance liquid chromatography (HPLC) and identified and confirmed as sesamol, sesamin, sesamolin, sesaminol diglucoside and sesaminol triglucoside by HPLC, infrared, nuclear magnetic resonance and mass spectrometry. When the rate of inhibition of lipid peroxidation and the superoxide radical‐scavenging power of the individual compounds were evaluated, the compounds showed antioxidant activity to different extents. The antioxidant activity of compounds by the β‐carotene‐bleaching assay followed the order sesamol > sesamolin ≥ sesamin > butylated hydroxytoluene (BHT) > sesaminol triglucoside > sesaminol diglucoside. By the thiocyanate method the inhibition of linoleic acid peroxidation shown by sesamol, sesamin, sesamolin, sesaminol triglucoside, sesaminol diglucoside and BHT at 200 mg l−1 was 77, 60, 69, 32, 25 and 49% respectively. A concentration–dependent superoxide–scavenging effect was also shown by these compounds. Sesamolin had an appreciable effect at 300 and 500 mg l−1, while the other compounds were more effective at 100 mg l−1. The study also established the occurrence of sesamol in the methanolic extract of defatted sesame cake for the first time. Copyright © 2005 Society of Chemical Industry

Increased production of antioxidative sesaminol glucosides from sesame oil cake through fermentation by Bacillus circulans strain YUS-2.

Bacillus circulans strain YUS-2 was isolated as the strongest antioxidant-producer in fermentation of sesame oil cake (SOC, defatted residue yielded from sesame seed oil production). Two major strong antioxidants from fermented SOC were purified and identified as known sesaminol triglucoside and sesaminol diglucoside, however, our results demonstrated that the fermentation process with B. circulans YUS-2 was highly effective to gain the extraction efficiency of the sesaminol glucosides.

Antioxidative activity of the crude extract of lignan glycosides from unroasted Burma black sesame meal

Sesame seed contains lignans and lignan glycosides. The antioxidative activity of the crude extract of lignan glycosides obtained from unroasted defatted black sesame seeds was investigated in this study. The components responsible for the antioxidative activity were also studied. The unroasted black sesame seeds, after defatted with n-hexane, were extracted with 80% methanolic solution to prepare for the crude extract of lignan glycosides. After chromatographic separation of this crude extract with octadecylsilane (ODS) column (2.5 cm i.d.×100 cm), four fractions (Fr1, Fr2, Fr3, Fr4) of the crude extract were obtained from the eluents of 25, 50, 75% aqueous methanolic solution and 100% methanol, respectively. Among them, Fr2 and Fr3 showed better antioxidative activity by 2,2-Diphenyl-1-picrylhydrazyl hydrate (DPPH) antioxidative assay. These two fractions were further purified by preparative HPLC (Hyperprep 100 C18 column; 20 mm i.d.×250 mm) and the main constituents were found to be lignan glycosides and some unknown brown materials. It was interesting to find that the brown materials (in Fr2) exhibited exceptional DPPH free radical scavenging effect, whereas the identified sesaminol triglucoside in Fr2 and sesaminol diglucoside in Fr3 possess no such activity. Using Cu +2-induced oxidation of human low-density lipoprotein (LDL) for the antioxidative assay, similar results were observed. Seaminol triglucoside and sesaminol diglucoside showed no effect on the extension of lag phase, while the brown materials had excellent inhibitory effect on the oxidation of LDL. Furthermore, natural antioxidants such as γ-tocopherol, sesamol and sesaminol were not detected in the crude extract of lignan glycosides. Our findings suggest that the brown materials present in Fr2 had a significant contribution to the antioxidative activity of the crude extract of lignan glycosides. Identification of the responsible components is underway.

HIGH PERFORMANCE LIQUID CHROMATOGRAPHIC DETERMINATION OF ANTIOXIDANT LIGNAN GLYCOSIDES IN SOME VARIETIES OF SESAME

ABSTRACTThe difference in the distribution of sesamin, sesamolin, sesaminol glucosides and sesamolinol components in representative varieties of sesame were compared. Quantitation was achieved by HPLC determination using an external standard. The most abundant lignan glucosides in sesame seed were sesaminol triglucoside. The content of sesaminol triglucoside in 100 g seeds ranged from 14.1 to 91.3 mg with an average value of 68.4 mg; that of sesaminol diglucoside from 8.2 to 18.3 mg with an average value of 11.6 mg; and that of sesaminol monoglucoside from 5.4 to 19.5 mg with an average value of 8.3 mg. The total content of sesaminol glucoside was 88.3 mg in 100 g of sesame seeds. Also, the sesamolinol content in 100 g sesame seed ranged from 17.6 to 28.5 mg, the average being 20.5 mg. Within