phytosterols and gamma-oryzanol

Rice bran oil (RBO) has been demonstrated to affect complex malfunctioned conditions such as oxidative stress, hyperlipidemia, hyperglycemia, hypertension, inflammation, abnormal cell growth (cancer), ulceration, immune and cognitive modulation. This unique effect of RBO is due to the presence of well-balanced fatty acid composition and several bioactive compounds, γ- oryzanol (cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, campesterol ferulate, and β-sitosteryl ferulate), vitamin E (tocopherol and tocotrienol), phytosterols (β-sitosterol, campesterol and stigmasterol) and other nutrients. The RBO composition of bioactive compounds varied geographically, thus the clear-cut mechanisms of action on complex disease cascades are still required. This review article summarized the RBO compositional profiling and compared it with other edible oils. This article also summarized Bangladesh RBO profiling and their proposed mechanism of action as well as the first line of defense in the prevention, management, and control of complex disease conditions. This review indicates how Bangladesh RBO increase their opportunity to be functional food for 21st century's ailment.

Topics: Anti-Inflammatory Agents; Bangladesh; Fatty Acids; Food Analysis; Functional Food; Hyperglycemia; Hyperlipidemias; Hypertension; Oxidative Stress; Phenylpropionates; Phytochemicals; Phytosterols; Rice Bran Oil; Vitamin E

Although much study has been done assessing activity of antioxidants at ambient and accelerated storage temperatures, the results cannot correctly depict their performance under frying conditions. Due to the stringent conditions imposed, most conventional antioxidative compounds failed under frying conditions, suggesting the need for a continuous modification to improve their effectiveness. Although syntheses and performance evaluation of over a hundred (semi)synthetic antioxidants have been reported in literature, only a small fraction have been specifically designed and/or evaluated under frying conditions. Here, the performance under frying conditions of major natural and synthetic antioxidants is reviewed. The recent trend in the designing of antioxidants for frying applications is also reviewed with the view of stimulating further study in this direction.

Topics: alpha-Tocopherol; Antioxidants; beta-Tocopherol; Carotenoids; Cooking; Hot Temperature; Lignans; Nutritive Value; Phenylpropionates; Phospholipids; Phytosterols; Plant Extracts; Plant Oils; Polyphenols; Squalene

Rice bran contains important bioactive phytochemicals. Among these phytochemicals, steryl ferulates including γ-oryzanol and its major components such as cycloartenyl ferulate (CAF), 24-methylenecycloartanyl ferulate (24-mCAF), β-sitosteryl ferulate (β-SF), and campesteryl ferulate have been intensively studied due to their crucial roles in pathological processes. On the basis of experimental studies published during the last decade in relation to antioxidant, anti-inflammatory, anti-ulcerogenic, hypolipidemic, anti-neoplastic, anti-diabetic, and anti-allergic phenomena, these bioactive phytochemicals are reviewed in this paper. Particularly, in vivo and in vitro studies have clarified that rice bran phytosteryl ferulates mediate anti-inflammatory effects by down-regulating the inflammatory transcription factor, nuclear factor κB (NF-κB), which in turn reduces expression of inflammatory enzymes such as COX-2 and iNOS, and proinflammatory cytokines such as IL-1β, IL-6 and TNF-α. Moreover, rice bran phytosteryl ferulates up-regulate blood adiponectin levels via indirect activation of peroxisomal proliferator-activated receptor γ (PPARγ) through NF-κB inhibition. In this review, we discuss potential pharmacological aspects of rice bran phytosteryl ferulates in the clinical setting.

Topics: Adiponectin; Animals; Anti-Allergic Agents; Anti-Inflammatory Agents; Coumaric Acids; Cyclooxygenase 2; Humans; Hypersensitivity; Immunity; Inflammation; Interleukin-6; Mice; NF-kappa B; Nitric Oxide Synthase Type II; Oryza; Oxidative Stress; Phenylpropionates; Phytosterols; Plant Extracts; PPAR gamma; Tumor Necrosis Factor-alpha; Up-Regulation

Topics: Animals; Anticholesteremic Agents; Dietary Fats, Unsaturated; Health Promotion; Humans; Hypolipidemic Agents; Phenylpropionates; Phytosterols; Plant Oils; Rice Bran Oil

The use of gamma-oryzanol and phytosterols is gaining popularity among various athletic populations. These compounds are being consumed in the belief that they elicit anabolic effects ranging from increased testosterone production and release to stimulating human growth hormone release. However, published scientific studies suggest that these compounds are poorly absorbed. Furthermore, animal studies indicate that when these compounds are injected subcutaneously or intravenously, they induce antianabolic or catabolic activity. Normally, less than 5% of orally consumed phytosterols are absorbed from the intestinal tract, with the majority being excreted in the feces. Intravenous or subcutaneous injections of gamma-oryzanol in rats have been shown to suppress luteinizing hormone release, reduce growth hormone synthesis and release, and increase release of the catecholamines, dopamine and norepinephrine, in the brain. Although it hasn't been directly measured, this metabolic milieu, if accurate, may actually reduce testosterone production.

Topics: Absorption; Animals; Diet; Humans; Hypothalamo-Hypophyseal System; Phenylpropionates; Phytosterols; Risk Factors; Sports

Gamma-oryzanol (Orz), a mixture of the ferulic acid ester of triterpene alcohols and phytosterols, was found abundantly in rice bran and rice bran oil which could be available and served as an antioxidant. The present study was to explore the potential protective effects of Orz on oxidative stress and cell apoptosis in human hepatic cells (L02 cells) induced by hydrogen peroxide (H

Topics: Antioxidants; Esters; Hepatocytes; Humans; Hydrogen Peroxide; Liver; NF-E2-Related Factor 2; Oxidative Stress; Phenylpropionates; Phytosterols; Rice Bran Oil; Signal Transduction; Triterpenes

Plants are natural laboratories producing a cornucopia of secondary metabolites of huge therapeutic potential. The oil extracted from rice bran, a by-product of brown rice processing, is abundant in valuable bioactive substances. One of its main ingredients is gamma-oryzanol that is a mixture of phytosterol esters and ferulic acid. These compounds exert a wide range of biological activities closely correlated with their chemical properties. Their hypocholesterolemic and antioxidant abilities are crucial for improving the physiology and condition of the human body. For these reasons, there has been a clear increase in the number of studies investigating the use of gamma-oryzanol in the treatment of many chronic diseases, and it is even tested as a promising non-pharmacological therapeutic agent in the treatment of COVID-19 in overweight people. This paper describes the chemical structure and activity of gamma-oryzanol based on biological activity of phytosterol esters and ferulic acid. It also discusses the effects of gamma-oryzanol on some physiological processes in the human and animal organisms.. Rośliny są naturalnymi laboratoriami, których wtórny metabolizm produkuje całe bogactwo związków chemicznych o ogromnym potencjale terapeutycznym. Olej ekstrahowany z otrębów ryżowych, stanowiących frakcję uboczną w procesie obróbki brązowego ryżu, obfituje w substancje biologicznie cenne. Jednym z głównych składników oleju ryżowego jest gamma-oryzanol stanowiący mieszaninę będących pochodnymi fitosteroli lub triterpenów oraz kwasu ferulowego. Substraty te charakteryzują się szeroką aktywnością biologiczną ściśle skorelowaną z ich właściwościami chemicznymi. Kluczowe w kontekście poprawy fizjologii i funkcjonowania organizmu są hipocholesterolemiczne oraz antyoksydacyjne właściwości tych związków. Z tego względu coraz więcej badań skupia się na wykorzystywaniu gamma-oryzanolu w terapiach wielu chorób przewlekłych, a nawet jako obiecującego, niefarmakologicznego środka leczniczego wspomagającego leczenie COVID-19 u osób cierpiących na nadwagę. W pracy scharakteryzowano strukturę chemiczną i działanie gamma-oryzanolu w oparciu o aktywność biologiczną estrów fitosteroli i kwasu ferulowego będących składnikami tej złożonej mieszaniny. Ponadto, opisano przykłady oddziaływania gamma oryzanolu na niektóre procesy fizjologiczne w organizmie człowieka i zwierząt.

Topics: Animals; Coumaric Acids; COVID-19; Esters; Humans; Phenylpropionates; Phytosterols; SARS-CoV-2

In this study, purified rice bran oil (RBO) was used as a lipid matrix model to study the individual and binary antioxidant capacity of the minor constituents (α-tocopherol, γ-oryzanol and phytosterol) added at different concentrations and ratios. The results revealed that concentration influenced on the oxidation stability and scavenging capacity, while ratio mainly affected the type of interaction or the degree of synergism or antagonism. It was important to notice that the antioxidant capacity of α-tocopherol would decrease under high concentration. Besides, the inhibition of phytosterol on α-tocopherol and the formation of hydrogen bond between γ-oryzanol and phytosterol were speculated by the interactions of these minor constituents. This work helps to select efficient combinations for stabilizing the anti-oxidation of nutrient enriched RBO or provide suggestions for moderate retain of minor constituents in RBO.

Topics: alpha-Tocopherol; Antioxidants; Lipids; Oxidation-Reduction; Phenylpropionates; Phytosterols; Rice Bran Oil

The objective of this study was to investigate the influence of self-assembled microstructure on lipid digestibility in phytosterol (γ-oryzanol and β-sitosterol) oleogels. Different molar ratios of γ-oryzanol and β-sitosterol yielded a variety of crystal morphologies; the resulting gels were tested for their lipid emulsification efficiency, release rate of free fatty acids (FFAs) during lipolysis, and their effect on lipase behavior. Results indicated that oleogels were harder to emulsify when compared to oil samples. The emulsification efficiencly was affected by both the gel strength and crystal morphology of the self-assembled structures within phytosterol oleogels. In oil emulsions, intestinal digestion resulted in more extensive lipid droplet coalescence with increased particle size when compared to oleogel emulsions. The FFA release rate suggested that the extent of lipid digestion was correlated to the emulsification efficiency. The interfacial binding of lipase indicated that the amount of lipase adsorption was positively correlated to the interface area created during the emulsification process. Finally, isothermal titration calorimetry results indicated that self-assembled structures within these oleogels physically obstructed the interaction between lipase and lipid. Ultimately, this led to lower reaction rate during gastrointestinal digestion. Collectively, these results may have important implications in designing oleogel systems with controlled lipid digestibility as well as controlling the bioavailability of delivered lipid-soluble bioactive compounds.

Topics: Digestion; Emulsions; Humans; Lipase; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Structure-Activity Relationship

In this study, a simultaneous analytical method of tocols, γ-oryzanols, phytosterols, squalene, cholecalciferol and phylloquinone were developed using HPLC-DAD-FLD. The developed method allowed the quantification of 18 compounds in 30 min. Method validation showed linearity of calibration curves (α = 0.05). RSD of intra-day, inter-day and inter-laboratory precision were less than 4.88%. The limit of detections (LODs) and limit of quantifications (LOQs) were low (0.009-2.166 μg g

Topics: Cholecalciferol; Oryza; Phenylpropionates; Phytosterols; Plant Oils; Squalene; Vitamin K 1

Oleogels were produced using a phytosterol blend of β-sitosterol/γ-oryzanol or a blend of sucrose stearate/ascorbyl palmitate (SSAP) as oleogelators. Four lipid phases were compared in oleogel formation for each oleogelator blend: menhaden oil, structured lipid (SL) of menhaden oil and 30 mol% caprylic acid (SL-C), SL of menhaden oil and 20 mol% stearic acid (SL-S), and SL of menhaden oil and 14 mol% each of caprylic and stearic acid (SL-CS). All SLs were produced enzymatically using a recombinant lipase from Candida antarctica as the biocatalyst. Menhaden oil, SL, phytosterol, or SSAP oleogels were evaluated as alternatives to shortening in the preparation of yellow cake in terms of batter and cake physicochemical properties. The shortening, phytosterol, and SSAP oleogel batters exhibited statistically similar specific gravities (0.85). The shortening, and menhaden oil phytosterol and SSAP oleogel batters, exhibited similar Power-Law values (n: 0.78, k: 31 Pa s

Topics: Ascorbic Acid; Caprylates; Fat Substitutes; Fatty Acids; Fish Oils; Food Analysis; Food Handling; Gels; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Stearic Acids; Sucrose

(1) Background: Modern dietary patterns with a high intake of fat and fructose, as well as refined carbohydrates, closely relate to lipid/glucose metabolic disorders. The main objective of this study is to provide new thoughts in designing functional food with some lipid/glucose metabolism regulating effects for obese people. (2) Methods: The alleviating abilities of γ-oryzanol, phytosterol or ferulic acid-enriched wheat flour on lipid/glucose metabolic dysfunction were evaluated in male SD rats induced by a high-fat-fructose diet. The underlying mechanisms were clarified using western blot. (3) Results: In an in vitro cell model, γ-oryzanol, phytosterol and ferulic acid regulate lipid/glucose metabolism by increasing the phosphorylation of AMPK and Akt, and PI3K expression, as well as decreasing expressions of DGAT1 and SCD. The in vivo study shows that ferulic acid and γ-oryzanol-enriched flours are beneficial for managing body weight, improving glucose metabolism, hyperlipidemia and hepatic lipid accumulation. Phytosterol-enriched flour exerted remarkable effects in regulating hyperinsulinemia, insulin resistance and hyperuricemia. Western blot analysis of proteins from liver samples reveals that these enriched flours alleviated hepatic lipid accumulation and insulin resistance through their elevation in the phosphorylation of AMPK and Akt. (4) Conclusions: Our study indicates that these enriched flours can serve as a health-promoting functional food to regulate obesity-related lipid/glucose metabolic dysfunction in rats.

Topics: Animal Feed; Animals; Biomarkers; Blood Glucose; Coumaric Acids; Dietary Sugars; Disease Models, Animal; Flour; Food, Fortified; Fructose; Hep G2 Cells; Humans; Lipids; Male; Metabolic Diseases; Obesity; Phenylpropionates; Phytosterols; Rats, Sprague-Dawley; Signal Transduction; Triticum

Rice bran oil (RBO) especially from colored rice is rich in phytochemicals and has become popular in food, cosmetic, nutraceutical and pharmaceutical applications owing to its offering health benefits. This study determined the contents of phytochemicals including oryzanols, phytosterols, tocopherols (Toc) and tocotrienols (T3) in RBOs extracted using different methods namely cold-press extraction (CPE), solvent extraction (SE) and supercritical CO

Topics: Liquid-Liquid Extraction; Oryza; Phenylpropionates; Phytochemicals; Phytosterols; Rice Bran Oil; Tocopherols; Tocotrienols

In this study the effect of lecithin (L) addition and solvent quality in a well-established oleogel system formed by β-sitosterol and γ-oryzanol (BG) was investigated. Medium chain triglycerides (MCT) and sunflower oil (SFO) were used as triglycerides and hexadecane (HEX) as a model of linear hydrocarbon. Lecithin was proposed due to its natural and versatile properties, showing different functionalities such as emulsifier and co-oleogelator. A study based on hierarchical organization of structured oil was performed applying techniques for bulk, meso and nanoscale. Self-sustained structures could no longer be observed after 40 wt% of BG replacement by lecithin. Small-angle X-ray scattering showed that the formed nanostructures (building blocks) were dependent on type of solvent and BG:L ratio in the mixture of oleogelators. Differential scanning calorimetry showed that stability against temperature was improved decreasing the polarity of the oil, and a time-dependent self-assembly of hybrid systems was observed from thermal and rheological measurements. Microscopy images exhibited changes on typical fibril aggregation of BG as lecithin was added, which promoted to a certain extent the suppression of ribbons. Oscillatory shear and uniaxial compression measurements were influenced by BG:L ratio and solvent mainly at higher lecithin amount. The combination of BG and MCT appeared to be the most affected by lecithin incorporation whereas SFO rendered harder oleogels. These results could contribute to understand the role of both lecithin and solvent type influencing the host oleogelator structure. It was hypothesized that intermolecular BG complex formation is hindered by lecithin, besides this phospholipid also might coexist as a different phase, causing structural changes in the gel network. Addressing the role of co-oleogelator it can provide the opportunity to tune soft materials with adjusted properties.

Topics: Calorimetry, Differential Scanning; Crystallization; Lecithins; Organic Chemicals; Phenylpropionates; Phytosterols; Sitosterols; Sunflower Oil; Triglycerides

Fifteen new multifunctional conjugates were designed and synthesized by chemically linking the steroidal framework of natural occurring γ-oryzanol and γ-oryzanol-derived phytosterols to a wide range of bioactive natural compounds (fatty acids, phenolic acids, amino acids, lipoic acid, retinoic acid, curcumin, and resveratrol). Starting from γ-oryzanol, which is the main component of rice bran oil, this study was aimed at assessing if the conjugation strategy might enhance some γ-oryzanol bioactivities. The antioxidant activity was evaluated through three different mechanisms, namely, DPPH-scavenging activity, metal-chelating activity, and β-carotene-bleaching inhibition. Measurement of the in vitro cell growth inhibitory effects on three different human cancer cellular lines was also carried out, and the potential hypocholesterolemic effect was studied. Compounds 10 and 15 displayed an improved antioxidant activity, with respect to that of γ-oryzanol. Compounds 2, 6, and 12 exerted an antiproliferative activity in the low micromolar range against HeLa and DAOY cells (GI

Topics: Anticholesteremic Agents; Antineoplastic Agents, Phytogenic; Antioxidants; beta Carotene; Cell Line, Tumor; Cell Proliferation; Chelating Agents; Free Radical Scavengers; Humans; Molecular Structure; Oryza; Phenylpropionates; Phytosterols; Plant Oils

Rice bran is a by-product of rice milling and is rich in bioactive molecules such as γ-oryzanol, phytosterols, and tocotrienols. The rice bran enzymatic extract (RBEE) previously showed vessel remodeling prevention and lipid-lowering, antioxidant, anti-inflammatory, and antiapoptotic activities. The aim of this study was to identify RBEE hypolipidemic mechanisms and to study the effects of RBEE on the progression of atherosclerosis disease and linked vascular dysfunction and liver steatosis in apolipoprotein E-knockout (ApoE-/-) mice fed low- or high-fat (LFD, HFD, respectively) and cholesterol diets.. ApoE-/- mice were fed LFD (13% kcal) or HFD (42% kcal) supplemented or not supplemented with 1 or 5% RBEE (w/w) for 23 wk. Then, serum, aorta, liver, and feces were collected and flash frozen for further analysis.. RBEE supplementation of HFD improved serum values by augmenting high-density lipoprotein cholesterol and preventing total cholesterol and aspartate aminotransferase increase. 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase activity was attenuated (1 and 5% RBEE) and cholesterol excretion increased (5% RBEE). Diet supplementation with 5% RBEE reduced plaque development regardless of the diet. In HFD-fed mice, both doses of RBEE reduced lipid deposition and macrophage infiltration in the aortic sinus and downregulated intercellular adhesion molecule-1 and vascular cell adhesion molecule-1 expression. None of these effects was observed in mice fed LFD. Liver steatosis was reduced by RBEE supplementation of LFD (1% RBEE) and HFD (1 and 5% RBEE) and nuclear peroxisome proliferator-activated receptor-α expression upregulated in the HDF 5% RBEE group.. Regular consumption of RBEE-supplemented HFD reduced plaque development and liver steatosis by decreasing inflammation and hyperlipidemia through an HMG-CoA reductase activity and lipid excretion-related mechanism.

Topics: Acyl Coenzyme A; Animals; Antioxidants; Aspartate Aminotransferases; Cholesterol, Dietary; Diet, High-Fat; Dietary Fiber; Dietary Supplements; Dose-Response Relationship, Drug; Fatty Liver; Inflammation; Intercellular Adhesion Molecule-1; Lipids; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Phenylpropionates; Phytosterols; Plant Extracts; Plaque, Atherosclerotic; PPAR alpha; Tocotrienols; Vascular Cell Adhesion Molecule-1

We demonstrate that by mixing the phytosterol-ester oryzanol with lecithin in an organic solvent, both components may be dispersed at much higher concentrations than they may be individually. Dynamic light scattering and molecular dynamics simulations show that the mechanism for this is the formation of r ∼ 4 nm mixed micelles. Infrared spectroscopy and simulations suggest that these micelles are formed due in part to hydrogen bonding of the phosphate of the lecithin head-group, and the phenol group of the oryzanol. Rheology shows that by mixing these materials at an equimolar ratio, highly viscous suspensions are created. Furthermore, by adding water to these samples, a solid-like gel may be formed which offers mechanical properties close to those desired for a margarine type spread, whilst still solubilizing the oryzanol.

Topics: Gels; Hydrogen Bonding; Lecithins; Micelles; Molecular Dynamics Simulation; Phenylpropionates; Phytosterols; Rheology; Viscosity

Atherosclerosis is associated with reduced mononuclear cell (MNC) telomere length, and senescent cells have been detected in atherosclerotic plaques. Rice bran is a source of γ-oryzanol, phytosterols and tocols with potential lipid-lowering, antioxidant and anti-inflammatory activities. Here, we tested the hypothesis that rice bran enzymatic extract (RBEE) impacts on apoptosis, telomere length and atherogenesis in mice.. Seven-week-old male ApoE-/- mice were fed high-fat diet (HFD) or isocaloric HFD supplemented with 5 % (w/w) RBEE for 23 weeks. Wild-type mice of the same age were kept under standard diet as controls.. Long-term food supplementation with RBEE lowers cholesterol and prevents atherosclerotic plaque development in ApoE-/- mice. Differential regulation of vascular and MNC apoptosis and senescence were identified as potential mechanisms.

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Aorta; Apoptosis; Atherosclerosis; Cholesterol, HDL; Cholesterol, LDL; Diet, High-Fat; Dietary Fiber; Endothelial Cells; Endothelium, Vascular; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Oryza; Phenylpropionates; Phytosterols; Plant Extracts; Plaque, Atherosclerotic; Triglycerides

A current challenge in the area of food emulsion is the design of microstructure that provides controlled release of volatile compounds during storage and consumption. Here, a new strategy addressed this problem at the fundamental level by describing the design of organogel-based emulsion from the self-assembly of β-sitosterol and γ-oryzanol that are capable of tuning volatile release. The results showed that the release rate (v

Topics: Emulsions; Phenylpropionates; Phytosterols; Sitosterols

HPLC fingerprint analysis combined with chemometrics was developed to discriminate between the red and the white rice bran grown in Indonesia. The major component in rice bran is γ-oryzanol which consisted of 4 main compounds, namely cycloartenol ferulate, cyclobranol ferulate, campesterol ferulate and β-sitosterol ferulate. Separation of these four compounds along with other compounds was performed using C18 and methanol-acetonitrile with gradient elution system. By using these intensity variations, principal component and discriminant analysis were performed to discriminate the two samples. Discriminant analysis was successfully discriminated the red from the white rice bran with predictive ability of the model showed a satisfactory classification for the test samples. The results of this study indicated that the developed method was suitable as quality control method for rice bran in terms of identification and discrimination of the red and the white rice bran.

Topics: Cholesterol; Chromatography, High Pressure Liquid; Indonesia; Oryza; Phenylpropionates; Phytosterols; Sitosterols; Triterpenes

Steryl ferulates (SFs) are a subclass of bioactive lipids contributing to the health-promoting effects of whole grains. Most related studies focus on γ-oryzanol, a SF mixture from rice, since individual steryl ferulates are not commercially available. There is little evidence that individual SFs may vary in their bioactivity. The aim of this study was to evaluate the antioxidant activity of eight individual SFs by determining their radical scavenging capacity. Additional molecular properties of the individual SFs were determined by molecular simulation in order to identify correlations with their antioxidant activities. Our study demonstrates that individual SFs exhibit 1,1-diphenyl-2-picrylhydrazyl radical, hydroxyl radical, and superoxide anion radical scavenging abilities with subtle differences that were highly dependent on the kind of reaction taking place. The grouping of SFs by principle component analysis was mainly attributed to molecular properties, not antioxidant activities. Solvation energy was significantly correlated with some experimental observations. To our knowledge, this is the first study to evaluate the antioxidant activity of eight individual steryl ferulates from different sources. Results of this work will provide better insight into the antioxidant activity of SFs and the health benefits of whole grains.

Topics: Algorithms; Antioxidants; Biphenyl Compounds; Coumaric Acids; Dietary Fiber; Edible Grain; Electron Spin Resonance Spectroscopy; Molecular Structure; Oryza; Oxidation-Reduction; Phenylpropionates; Phytosterols; Picrates; Plant Extracts

The effect of oryzanol (well known hypolipidemic component in rice bran oil) and its chemical constituents- ferulic acid (FA) and phytosterols on hypolipidemia were investigated.. Docking (in silico) studies showed that FA had a better binding ability with lipase while sterols bound well with HMG-CoA reductase. Further in vivo studies of feeding high fat (30%) to rats increased body weights, serum TC, TG, non-HDL-C and reduced HDL-C were observed, compared to normal diet fed group (ND). ORZ treated groups alleviated the lipid profile. Furthermore, increased organ weights, higher intestinal lipase activity, and liver lipid peroxidation was observed in the high-fat group (HF). These effects were ameliorated in oryzanol concentrate fed groups (ORZ). Higher fecal fat was found in ORZ groups, analysis of fecal matter by mass spectroscopy revealed the presence of FA. In vitro, a bile acid binding study supported the strong affinity of sterol towards bile acids. In conclusion, oryzanol in the intestine is cleaved into FA and sterol by intestinal lipase enzymes both lipase and HMG-CoA reductase activities were inhibited, respectively. These hydrolysates eliminated the bile acids, thus lowering lipid profiles.

Topics: Animals; Bile Acids and Salts; Body Weight; Coumaric Acids; Drinking; Eating; Humans; Hydroxymethylglutaryl CoA Reductases; Hydroxymethylglutaryl-CoA Reductase Inhibitors; Hypolipidemic Agents; Lipase; Male; Oryza; Phenylpropionates; Phytosterols; Protein Binding; Rats, Wistar

Algae oil, enriched with omega-3 long-chain polyunsaturated fatty acids (ω-3 LC-PUFA), is known for its health benefits. However, protection against lipid oxidation as well as masking of unpleasant fishy malodors in algae oil enriched foods is a big challenge to achieve. In this study, we firstly achieved a one-pot ultrasound emulsification strategy (alternative heating-homogenization) to prepare phytosterol structured thermosensitive algae oil-in-water nanoemulsion stabilized by quillaja saponin. After spray drying, the resulting algae oil powders from the structured nanoemulsion templates exhibit an excellent reconstructed behavior, even after 30 d of storage. Furthermore, an enhanced oxidative stability was obtained by reducing both the primary and secondary oxidation products through formulation with β-sitosterol and γ-oryzanol, which are natural antioxidants. Following the results of headspace volatiles using dynamic headspace-gas chromatography-mass spectrometry (DHS-GC-MS), it was clear that the structured algae oil-loaded nanoemulsion and powder had lower levels of fishy off-flavour (e.g., (Z)-heptenal, decanal, ethanone, and hexadecenoic acid), whereas the control emulsion and oil powder without structure performed worse. This study demonstrated that the structure from phytosterols is an effective strategy to minimize the fishy off-flavour and maximize oxidative stability of both algae oil nanoemulsions and spray-dried powders, and opens up the possibility of formulation design in polyunsaturated oil encapsulates as novel delivery systems to apply in functional foods and beverages.

Topics: Antioxidants; Drug Stability; Emulsions; Fatty Acids, Omega-3; Food, Fortified; Odorants; Oils; Phenylpropionates; Phytosterols; Powders; Quillaja Saponins; Sitosterols; Taste

Steryl ferulates synthesised from commercial sterols as well as commercial oryzanol were used to better understand how structural features affect antioxidant activity in vitro by the ABTS(+) radical decolorization assay, by oxidative stability index (OSI) of soybean oil, and by analysis of antioxidant activity during frying. Steryl ferulates inhibited the ABTS(+) radical by 6.5-56.6%, depending on their concentration, but were less effective, especially at lower concentrations, than ferulic acid. Ferulic acid and steryl ferulates had either no effect, or lowered the OSI of soybean oil by up to 25%, depending on the concentration. In their evaluation as frying oil antioxidants, steryl ferulates with a saturated sterol group had the best antioxidant activity, followed by sterols with one double bond in the C5 position. The results indicate that a dimethyl group at C4 as well as a C9,C19 cyclopropane group, as found in oryzanol, negatively affects antioxidant activity in frying oils.

Topics: Antioxidants; Coumaric Acids; Molecular Structure; Phenylpropionates; Phytosterols

γ-Oryzanol, a mixture of ferulic acid esters of triterpene alcohols and sterols, is a nutritionally important group of rice secondary metabolites. A library of 27 γ-oryzanol was assembled from existing data and used to assist identification and quantification of γ-oryzanol isolated from 16 Korean rice varieties (11 white and 5 pigmented). γ-Oryzanol was analyzed with liquid chromatography with diode array detection and electrospray ionization mass spectrometry. Nineteen different γ-oryzanol were observed and identified as stigmasterol, campesterol and sitosterol or common and hydroxylated triterpene alcohols. In the 16 varieties, the total γ-oryzanol content averaged 43.8 mg/100 g (range, 26.7-61.6 mg/100 g), which Josaengheugchal exhibited the highest level (61.6 mg/100 g). The Korean rice varieties were classified based on qualitative and quantitative γ-oryzanol data by multivariate statistical analysis. Clusters of specialty rice varieties exhibited higher γ-oryzanol levels than those of common rice varieties.

Topics: Cholesterol; Chromatography, Liquid; Coumaric Acids; Humans; Korea; Oryza; Phenylpropionates; Phytosterols; Seeds; Species Specificity; Spectrometry, Mass, Electrospray Ionization; Triterpenes

Rice bran enzymatic extract (RBEE) has advantages compared to the original rice bran or its oils including water solubility, lack of rancidity and increased content in high nutritional proteins and nutraceutical compounds, particularly phytosterols, γ-oryzanol and tocols. Our aim was to determine the beneficial effects of RBEE in the pathogenesis of metabolic syndrome in obese Zucker rats.. Obese Zucker rats and their lean littermates were fed a 1 and 5 % RBEE-supplemented diet (O1, O5, L1 and L5). Simultaneously, obese and lean Zucker rats, fed a standard diet, were used as controls (OC and LC, respectively). Body weight, food and water intake, and systolic blood pressure were weekly evaluated. After treatment, biochemical assays of serum glucose, insulin, triglycerides (TG), total cholesterol (TC), non-esterified fatty acids (NEFA), adiponectin and nitrates (NO((x))) were determined.. RBEE treatment reduced circulating levels of TG and TC, whereas increased HDL-cholesterol without altering NEFA values in obese rats. The extract also induced a significant dose-dependent reduction of hypertension linked to obesity. RBEE of 5 % improved insulin resistance and subsequently reduced HOMA-IR index without altering serum glucose levels. Obese animals treated with RBEE showed partial restoration of adiponectin levels and a significant attenuation of pro-inflammatory values of NO((x)).. These findings evidence the nutraceutical properties of RBEE against the pathogenesis of metabolic syndrome by attenuating dyslipidemia, hypertension and insulin resistance as well as by restoring hypoadiponectinemia associated to obesity.

Topics: Adiponectin; Animals; Blood Glucose; Blood Pressure; Body Weight; Cholesterol; Diet; Dyslipidemias; Fatty Acids, Nonesterified; Hypertension; Insulin; Insulin Resistance; Metabolic Syndrome; Nitrates; Obesity; Oryza; Phenylpropionates; Phytosterols; Plant Extracts; Rats; Rats, Zucker; Triglycerides; Water

The formation kinetics of self-assembling tubules composed of phytosterol:gamma-oryzanol mixtures were investigated at the Canadian Light Source on the mid-IR beamline using synchrotron radiation and Fourier transform infrared spectroscopy (FT-IR). The Avrami model was fitted to the changing hydrogen bonding density occurring at 3450 cm(-1). The nucleation process was found to be highly dependent on the molecular structure of the phytosterol. The nucleation event for cholesterol:gamma-oryzanol was determined to be sporadic whereas 5alpha-cholestan-3beta-ol:gamma-oryzanol and beta-sitosterol:gamma-oryzanol underwent instantaneous nucleation. One-dimensional growth occurred for each phytosterol:gamma-oryzanol mixture and involved the evolution of highly specific intermolecular hydrogen bonds. More detailed studies on the cholesterol:gamma-oryzanol system indicated that the nucleation activation energy, determined from multiple rate constants, obtained using the Avrami model, was at a minimum when the two compounds were at a 1:1 weight ratio. This resulted in drastic differences to the microscopic structures and affected the macroscopic properties such as turbidity. The formation of the phytosterol:gamma-oryzanol complex was due to intermolecular hydrogen bonding, which was in agreement with the infrared spectroscopic evidence.

Topics: Calorimetry, Differential Scanning; Hydrogen Bonding; Kinetics; Microscopy; Phenylpropionates; Phytosterols; Spectroscopy, Fourier Transform Infrared

Gamma-oryzanol, a group of phytosterol ferulates found in rice bran, possesses antioxidative activity and other bioactivities. The kinetics of thermal degradation of gamma-oryzanol in stripped rice bran oil (SRBO) were investigated under heating at 132, 160, 192 and 222 degrees C for 480, 140, 60 and 50 h, respectively. Losses of the overall gamma-oryzanol and its components (cycloartenyl ferulate, 24-methylene cycloartanyl ferulate, campesteryl ferulate and beta-sitosteryl ferulate) could be expressed by the first-order kinetics model. The rate constant of thermal degradation of gamma-oryzanol increased with increasing heating temperatures. The temperature dependence of the obtained rate constants was found to obey the Arrhenius equation. Campesteryl ferulate showed slightly more thermally resistant than other components at temperature lower than 160 degrees C. However, the change in the absorbance from 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay as a function of heating time exhibited the same pattern for the SRBO with and without gamma-oryzanol for all studied heating temperatures.

Topics: Antioxidants; Biphenyl Compounds; Chromatography, High Pressure Liquid; Hot Temperature; Indicators and Reagents; Kinetics; Oxidation-Reduction; Phenylpropionates; Phytosterols; Picrates; Plant Oils; Rice Bran Oil

Some of the pharmacological properties of phytosteryl ferulates may be linked to their antioxidant potential. In this study, 2,2-diphenyl-1-picrylhydrazyl (DPPH), electron spin resonance (ESR), and thiobarbituric acid-reactive substances (TBARS) assays demonstrated that phytosteryl ferulates such as cycloartenyl ferulate (CAF), 24-methylenecycloartanyl ferulate (24-mCAF), and beta-sitosteryl ferulate (beta-SF) and ferulic acid (FA) each exerted strong free radical scavenging and antioxidation of lipid membrane, which were comparable to alpha-tocopherol. However, the sterol moiety alone, such as cycloartenol (CA), had neither activity. Since, the reactive oxygen species (ROS) production in the cell complex defense mechanism cannot be ruled out with the cell free system, we measured ROS production in NIH 3T3 fibroblast cells induced by H(2)O(2). CAF and ethyl ferulate (eFA) greatly decreased the ROS level in this system. CA also significantly inhibited the ROS level, suggesting that CA could inhibit ROS production in living cells. Besides these, CAF, 24-mCAF, beta-SF, as well as eFA and CA, all these chemicals significantly inhibited the NF-kappaB activity as analyzed by measuring translocation of NF-kappaB p65 in LPS-stimulated RAW 264.7 macrophages. These observations revealed that phytosteryl ferulates are responsible for the antioxidant and anti-inflammatory activity via ROS scavenging and inhibition of ROS production.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antioxidants; Cell Line; Coumaric Acids; Free Radical Scavengers; Macrophages; Membranes, Artificial; Mice; NF-kappa B; NIH 3T3 Cells; Phenylpropionates; Phytosterols; Reactive Oxygen Species; Structure-Activity Relationship

We have recently reported that phytosteryl ferulates isolated from rice bran inhibit nuclear factor-kappaB (NF-kappaB) activity in macrophages. In the present study, we investigated the effect of gamma-oryzanol (gamma-ORZ), a mixture of phytosteryl ferulates, cycloartenyl ferulate (CAF), one of the components of gamma-ORZ, and ferulic acid (FA), a possible metabolite of gamma-ORZ in vivo, on a model of colitis in mice.. We induced colitis with dextran sulphate sodium (DSS) in mice and monitored disease activity index (DAI), histopathology score, tissue myeloperoxidase (MPO) activity, mRNA expressions of cytokines and COX-2, colon length, antioxidant potency and NF-kappaB activity in colitis tissue.. Both DAI and histopathology score revealed that DSS induced a severe mucosal colitis, with a marked increase in the thickness of the muscle layer, distortion and loss of crypts, depletion of goblet cells and infiltration of macrophages, granulocytes and lymphocytes. MPO activity, pro-inflammatory cytokines and COX-2 levels, NF-kappaB p65 nuclear translocation and inhibitory protein of nuclear factor-kappaB-alpha degradation levels were significantly increased in DSS-induced colitis tissues. gamma-ORZ (50 mg kg(-1) day(-1) p.o.) markedly inhibited these inflammatory reactions and CAF had a similar potency. In vitro assay demonstrated that gamma-ORZ and CAF had strong antioxidant effects comparable to those of alpha-tocopherol.. Phytosteryl ferulates could be new potential therapeutic and/or preventive agents for gastrointestinal inflammatory diseases. Their anti-inflammatory effect could be mediated by inhibition of NF-kappaB activity, which was at least partly due to the antioxidant effect of the FA moiety in the structure of phytosteryl ferulates.

Topics: alpha-Tocopherol; Animals; Anti-Inflammatory Agents; Antioxidants; Colitis; Coumaric Acids; Dextran Sulfate; Disease Models, Animal; Intestinal Mucosa; Male; Mice; Mice, Inbred C57BL; NF-kappa B; Oryza; Phenylpropionates; Phytosterols

Palm stearin (PS) and rice bran oil (RBO) blends of varying proportions were subjected to enzymatic interesterification (EIE) using a 1,3 specific immobilized lipase. The interesterified blends were evaluated for their physicochemical characteristics and bioactive phytochemical contents using differential scanning calorimeter (DSC), X-ray diffraction (XRD), gas chromatography (GC) and high performance liquid chromatography (HPLC). The blends of PS and RBO in different proportions (40:60, 50:50, 60:40 and 70:30) had saturated fatty acid content and unsaturated fatty acid content in the range of 37.6-52.0% and 48.0-62.4%, respectively. The blends 40:60, 50:50 and 60:40 showed a considerable reduction in their highest melt peak temperature (TP) and solid fat content (SFC) on EIE. The interesterified blends retained bioactive phytochemicals like tocols (839-1172 ppm), sterols (4318-9647 ppm), oryzanols (3000-6800ppm) and carotene (121-180 ppm). XRD studies demonstrated that the interesterified blends contained beta and beta' polymorphic forms.

Topics: Arecaceae; Biological Products; Calorimetry; Carotenoids; Catalysis; Crystallization; Dietary Fats, Unsaturated; Esterification; Fungi; Iodine; Lipase; Phenylpropionates; Phytosterols; Plant Oils; Rice Bran Oil; Stearates; Temperature

The content of gamma-oryzanol and the composition of steryl ferulates were determined in brown rice of European origin using on-line coupled liquid chromatography-gas chromatography (LC-GC). Analysis of 30 brown rice samples of various cultivars, grown at different sites and in different seasons, revealed the gamma-oryzanol content to range from 26 to 63 mg/100 g. Cycloartenyl ferulate and 24-methylenecycloartanyl ferulate were the major components of gamma-oryzanol followed by campesteryl ferulate, campestanyl ferulate, and beta-sitosteryl ferulate. The proportions of individual steryl ferulates exhibited enormous variability. However, irrespectively of the great variations observed for single steryl ferulates, the proportions of the sum of 4,4'-dimethylsteryl ferulates (cycloartenyl ferulate, 24-methylenecycloartanyl ferulate) and the sum of 4-desmethylsteryl ferulates (campesteryl ferulate, campestanyl ferulate, and beta-sitosteryl ferulate) were rather constant. The significant natural variability observed for gamma-oryzanol content and composition of steryl ferulates were shown to be influenced by environmental conditions but not by the degree of maturity of rice grains.

Topics: Chromatography, Gas; Chromatography, Liquid; Coumaric Acids; Environment; Europe; Oryza; Phenylpropionates; Phytosterols; Seeds

Ferulic acid esters of triterpene alcohols and sterols in rice bran oil have been extensively studied and reported to possess important pharmacological actions. Inconsistent results on the numbers and structures of ferulates have been reported, primarily because of the analytical procedures employed. Conventional methods for analysis of phytosterol content in oil are carried out by characterization of trimethylsilylated derivatives (TMS) using GC-EI-MS after saponification of oils or individual compound isolated from oils. This study developed an LC-MS/MS method for the direct analysis of triterpene alcohol and sterol esters in rice bran oil. In addition to verifying the results of previous research, nine new relatively polar triterpene alcohol and sterol esters were characterized by their retention behaviors in LC and ESI-MS data from both negative- and positive-ion mode. This is the first evidence for the presence of hydroxylated ferulate esters and caffeate esters as part of gamma-oryzanol in rice bran. The method enables rapid and direct on-line characterization of triterpene alcohol and sterol esters in oils. LC-MS/MS equipped with reverse-phase LC and ESI-MS should be well-suited for identification and quantification of the polar metabolites of phytosterols in biological fluids after consumption of rice bran oil or other oils.

Topics: Alcohols; Chromatography, High Pressure Liquid; Coumaric Acids; Mass Spectrometry; Oryza; Phenylpropionates; Phytosterols; Spectrometry, Mass, Electrospray Ionization; Triterpenes

Inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice was observed in the methanol extract of rice bran and gamma-oryzanol. The active components of rice bran, sitosterol ferulate, 24-methylcholesterol ferulate, cycloartenol ferulate and 24-methylenecycloartanol ferulate inhibited markedly the TPA-induced inflammation in mice. The 50% inhibitory dose of these compounds for TPA-induced inflammation was 0.2-0.3 mg/ear. Furthermore, cycloartenol ferulate markedly inhibited the tumor-promoting effect of TPA in 7,12-dimethylbenz[a]anthracene-initiated mice.

Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Anticarcinogenic Agents; Carcinogens; Cocarcinogenesis; Dermatitis, Contact; Female; Hypolipidemic Agents; Mice; Mice, Inbred ICR; Oryza; Phenylpropionates; Phytosterols; Plant Extracts; Skin; Skin Neoplasms; Sterols; Tetradecanoylphorbol Acetate; Triterpenes

Hypolipidemic effects of gamma-oryzanol (OZ) and cycloartenol ferulic acid ester (CAF) on the hyperlipidemia induced by ingestion of a high cholesterol diet (HCD) in male Sprague-Dawley rats were investigated. The test drugs were given orally and intravenously, daily for 12 days with the HCD feeding. The oral administration with OZ and CAF at 100 mg/kg daily for 6 or 12 days did not apparently prevent the hyperlipidemia induced by HCD-feeding. The intravenous administrations with OZ and CAF at 10 mg/kg for 6 days significantly inhibited the increases in serum total cholesterol (TC), phospholipid (PL) and free cholesterol by HCD. OZ and CAF did not inhibit the decreases of TC in high density lipoprotein (HDL-TC) and HDL-PL by HCD. The increases of atherogenic index [( TC-HDL-TC]/[HDL-TC] and [PL-HDL-PL]/[HDL-PL]) with the HCD feeding were reduced by the intravenous administrations of OZ and CAF. Triglyceride, nonesterified fatty acid, lactate dehydrogenase and transaminase (GOT and GPT) markedly decreased below the control level by the intravenous administrations of OZ and CAF for 12 days. These results suggest that the intravenous administrations of OZ and CAF may have accelerated the excretion of lipids in the blood.

Topics: Animals; Blood Proteins; Body Weight; Cholesterol, Dietary; Cinnamates; Coumaric Acids; Enzymes; Hyperlipidemias; Hypolipidemic Agents; Male; Organ Size; Phenylpropionates; Phytosterols; Rats; Rats, Inbred Strains