Quantitative analyses of individual γ-Oryzanol (Steryl Ferulates) in conventional and organic brown rice (Oryza sativa L.)
TL;DR: In this article, the content of γ-Oryzanol (steryl ferulates; SF) in brown rice was qualitatively determined by HPLC using SF isolated from a commercial ǫ-oryzanol mixture as the external standard.
Abstract: γ-Oryzanol (steryl ferulates; SF) has been shown to be a major bioactive compound in rice. To determine the content of individual γ-oryzanols in brown rice by high performance liquid chromatography (HPLC), purification of individual SF for use as an external standard is required. Four main SF were isolated from a commercial γ-oryzanol mixture and identified as cycloartenyl ferulate (1), 24-methylenecycloartanyl ferulate (2), campesteryl ferulate (3), and sitosteryl ferulate (4) based on mass spectrometry and nuclear magnetic resonance spectroscopic data. The SF contents between conventional and organic brown rice were qualitatively determined by HPLC using SF isolated from a commercial γ-oryzanol mixture as the external standard. The total γ-oryzanol content (mg/100 g) in organic brown rice (65.6 ± 2.7) was slightly higher (P < 0.05) than that found in conventional brown rice (60.2 ± 1.8). The content (mg/100 g) of 1 (21.2 ± 0.9) and 4 (9.8 ± 0.4) in organic brown rice was higher (P < 0.05) than that observed in conventional brown rice (1, 18.2 ± 1.1; 4, 8.5 ± 0.3). However, the content of 2 and 3 in the conventional and organic brown rice samples did not differ significantly. These results indicate that the cultivation methods do significantly alter the γ-oryzanol content for conventional and organic brown rice.
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TL;DR: Phytosterol-enriched functional foods first appeared about twenty years ago and many clinical studies have confirmed the low density lipoprotein (LDL) cholesterol-lowering properties of various types of phytosterols, which have provided insights to better understand the cholesterol- Lowering and other biological effects of plant sterols.
Abstract: Phytosterols (plant sterols) occur in the cells of all plants. They are important structural components that stabilize the biological membranes of plants. Sterols can occur in the "free" unbound form or they can be covalently bound via an ester or glycosidic bond. Since our previous 2002 review on phytosterols and phytosterol conjugates, phytosterol glucosides have been found to be important structural components in the lipid rafts of the plasma membrane of plant cells, where they are thought to be essential to the function of plasma membrane enzymes and perhaps other proteins. Phytosterols also serve as precursors in the synthesis of important bioactive compounds such as steroidal saponins, steroidal glycoalkaloids, phytoecdysteroids, and brassinosteroids. Methods for the analysis of phytosterols range from traditional gas chromatography of free phytosterols to modern sophisticated forms of mass spectrometry which have been used for the new field of sterol lipidomics, sometimes called "sterolomics." Phytosterol-enriched functional foods first appeared about twenty years ago and many clinical studies have confirmed the low density lipoprotein (LDL) cholesterol-lowering properties of various types of phytosterols. In recent years additional clinical studies and more than ten important meta-analyses have provided insights to better understand the cholesterol-lowering and other biological effects of plant sterols.
141 citations
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TL;DR: An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside, which exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6.
Abstract: The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity.
86 citations
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TL;DR: Consumption of organic food seems to be positive from a public health point of view, although the reasons are unclear, and synergistic effects between various constituents within the food are likely.
Abstract: An increasing interest in organic agriculture for food production is seen throughout the world and one key reason for this interest is the assumption that organic food consumption is beneficial to public health The present paper focuses on the background of organic agriculture, important public health related compounds from crop food and variations in the amount of health related compounds in crops In addition, influence of organic farming on health related compounds, on pesticide residues and heavy metals in crops, and relations between organic food and health biomarkers as well as in vitro studies are also the focus of the present paper Nutritionally beneficial compounds of highest relevance for public health were micronutrients, especially Fe and Zn, and bioactive compounds such as carotenoids (including pro-vitamin A compounds), tocopherols (including vitamin E) and phenolic compounds Extremely large variations in the contents of these compounds were seen, depending on genotype, climate, environment, farming conditions, harvest time, and part of the crop Highest amounts seen were related to the choice of genotype and were also increased by genetic modification of the crop Organic cultivation did not influence the content of most of the nutritional beneficial compounds, except the phenolic compounds that were increased with the amounts of pathogens However, higher amounts of pesticide residues and in many cases also of heavy metals were seen in the conventionally produced crops compared to the organic ones Animal studies as well as in vitro studies showed a clear indication of a beneficial effect of organic food/extracts as compared to conventional ones Thus, consumption of organic food seems to be positive from a public health point of view, although the reasons are unclear, and synergistic effects between various constituents within the food are likely
69 citations
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TL;DR: The results demonstrate that the black-purple rice in the dehulled form in which it is consumed by humans contains a rich heterogeneous mixture of phytochemicals which may provide a basis for the potential health benefits, and highlights the possible use of the rice as functional food.
Abstract: Black-purple rice is becoming popular with health conscious food consumers. In the present study, the secondary metabolites in dehulled black-purple rice cv. Asamurasaki were analysed using HPLC-PDA-MS(2). The seeds contained a high concentration of seven anthocyanins (1400 μg/g fresh weight) with cyanidin-3-O-glucoside and peonidin-3-O-glucoside predominating. Five flavonol glycosides, principally quercetin-3-O-glucoside and quercetin-3-O-rutinoside, and flavones were detected at a total concentration of 189 μg/g. The seeds also contained 3.9 μg/g of carotenoids consisting of lutein, zeaxanthin, lycopene and β-carotene. γ-Oryzanol (279 μg/g) was also present as a mixture of 24-methylenecycloartenol ferulate, campesterol ferulate, cycloartenol ferulate and β-sitosterol ferulate. No procyanidins were detected in this variety of black-purple rice. The results demonstrate that the black-purple rice in the dehulled form in which it is consumed by humans contains a rich heterogeneous mixture of phytochemicals which may provide a basis for the potential health benefits, and highlights the possible use of the rice as functional food.
67 citations
Cites background from "Quantitative analyses of individual..."
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TL;DR: The objective of this work was to review the recent advances in research performed for purposes of evaluation of nutritional value and potential health benefits of the whole BR grain and present economic and environmental benefits for the consumption of whole BR instead of the polished or white rice.
Abstract: Obesity and chronic diet-related diseases such as type 2 diabetes, hypertension, cardiovascular disease, cancers, and celiac are increasing worldwide. The increasing prevalence of these diseases has led nutritionists and food scientists to pay more attention to the relationship between diet and different disease risks. Among different foods, rice has received increasing attention because it is a major component of billions of peoples' diets throughout the world. Rice is commonly consumed after polishing or whitening and the polished grain is known a high glycemic food because of its high starch content. In addition, the removal of the outer bran layer during rice milling results in a loss of nutrients, dietary fiber, and bioactive components. Therefore, many studies were performed to investigate the potential health benefits for the consumption of whole brown rice (BR) grain in comparison to the milled or white rice (WR). The objective of this work was to review the recent advances in research performed for purposes of evaluation of nutritional value and potential health benefits of the whole BR grain. Studies carried out for purposes of developing BR-based food products are reviewed. BR safety and preservation treatments are also explored. In addition, economic and environmental benefits for the consumption of whole BR instead of the polished or WR are presented. Furthermore, challenges facing the commercialization of BR and future perspectives to promote its utilization as food are discussed.
54 citations
References
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TL;DR: In this article, the antioxidant activities of vitamin E (α-tocopherol, α-tocotrienol, γ-tocoperol, and γ-, O-Znol components (cycloartenyl ferulate, 24-methylenecycloartanyl ferulate and campesteryl ferulates) purified from rice bran were investigated in a cholesterol oxidation system accelerated by 2,2‘-azobis(2-methylpropionamidine) dihydrochloride.
Abstract: The antioxidant activities of vitamin E (α-tocopherol, α-tocotrienol, γ-tocopherol, and γ-tocotrienol) and γ-oryzanol components (cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, and campesteryl ferulate) purified from rice bran were investigated in a cholesterol oxidation system accelerated by 2,2‘-azobis(2-methylpropionamidine) dihydrochloride. All components exhibited significant antioxidant activity in the inhibition of cholesterol oxidation. The highest antioxidant activity was found for 24-methylenecycloartanyl ferulate, and all three γ-oryzanol components had activities higher than that of any of the four vitamin E components. Because the quantity of γ-oryzanol is up to 10 times higher than that of vitamin E in rice bran, γ-oryzanol may be a more important antioxidant of rice bran in the reduction of cholesterol oxidation than vitamin E, which has been considered to be the major antioxidant in rice bran. The antioxidant function of these components against cholesterol oxidation may contrib...
450 citations
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TL;DR: In this article, the authors examine the distribution of economic knowledge within two food chains: the conventional food chain, which relies on intensive inputs into the food production process, and thus tends to distribute knowledge towards input suppliers, and the organic food supply chain which distributes knowledge back towards the farm as farmers must relocalise their understandings of the production process.
Abstract: In this paper we examine the way that knowledge is distributed within economic networks. Adopting a broad evolutionary approach we examine the distribution of economic knowledge within two food chains: the conventional food chain, which relies on intensive inputs into the food production process, and thus tends to distribute knowledge towards input suppliers, and the organic food supply chain, which distributes knowledge back towards the farm as farmers must relocalise their understandings of the production process. We present two stylised accounts of each chain and show that for farmers to move from one to the other they must forget many of the practices so characteristic of the conventional chain in order to (re)learn how to farm in an ecologically benign fashion. In the organic chain, we argue, farmers can once again become “knowing agents”.
335 citations
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TL;DR: High-purity gamma-oryzanol was obtained from crude rice bran oil using a normal-phase preparative scale HPLC and identification was accomplished using GC/MS with an electron impact mass spectrum after components were transformed into trimethylsilyl ether derivatives.
Abstract: High-purity gamma-oryzanol was obtained from crude rice bran oil using a normal-phase preparative scale HPLC. A reverse-phase HPLC method was used for separating the individual components of gamma-oryzanol present in rice bran oil. Ten fractions were isolated and collected using the reverse-phase HPLC method, and their structures were identified. Identification was accomplished using GC/MS with an electron impact mass spectrum after components were transformed into trimethylsilyl ether derivatives. The 10 components of gamma-oryzanol were identified as Delta(7)-stigmastenyl ferulate, stigmasteryl ferulate, cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, Delta(7)-campestenyl ferulate, campesteryl ferulate, Delta(7)-sitostenyl ferulate, sitosteryl ferulate, compestanyl ferulate, and sitostanyl ferulate. Three of these, cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, and campesteryl ferulate, were major components of gamma-oryzanol.
321 citations
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TL;DR: Six novel feruloyl esters of triterpene alcohols and sterols, besides five known trans-ferulates, showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, and eight free sterols examined showed weaker activity than their corresponding ferulates.
Abstract: Six novel feruloyl esters of triterpene alcohols and sterols, viz., two trans-ferulates, cycloeucalenol and 24-methylenecholesterol trans-ferulates, and four cis-ferulates, cycloartenol, 24-methyelenecycloartanol, 24-methylcholesterol, and sitosterol cis-ferulates, besides five known trans-ferulates, cycloartenol (CAR), 24-methylenecycloartanol (24-MCA), 24-methylcholesterol, sitosterol, and stigmastanol trans-ferulates, and one known cis-ferulate, stigmastanol cis-ferulate, were isolated from the methanol extract of edible rice bran. These and eight other synthetic trans- and cis-ferulates of triterpene alcohols and sterols, along with the corresponding free alcohols, were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID(50)) was 0. 1-0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID(50) 0.2-0.3 mg/ear), eight free sterols examined showed weaker activity (ID(50) 0.7-2.7 mg/ear) than their corresponding ferulates.
265 citations
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TL;DR: In this paper, a novel foodstuff from pre-germinated brown rice by a twin-screw extruder was investigated, and the characteristics of the components of the materials and the products are as follows: (1) Pre-gerMINATED brown rice was prepared by soaking in water for 72h at 30°C followed by drying to 13-15% moisture content at 15°C in a low-humidity artificial weather-control room.
Abstract: Development of a novel foodstuff from pre-germinated brown rice by a twin-screw extruder was investigated. The characteristics of the components of the materials and the products are as follows: (1) Pre-germinated brown rice was prepared by soaking in water for 72 h at 30 °C followed by drying to 13–15% moisture content at 15 °C in a low-humidity artificial weather-control room. Total dietary fiber, total ferulic acid and gamma-aminobutyric acid (GABA) contents of the pre-germinated brown rice were higher than those of ordinary brown rice or polished rice. (2) The pre-germinated brown rice was processed with a twin-screw extruder. The puffed pre-germinated brown rice contained more oryzanol, inositol, total ferulic acid and total dietary fibers compared with the un-puffed polished rice. The product prepared by the co-extrusion of pre-germinated brown rice (90%) and beer yeast (10%) contained more free amino acids, such as GABA, glycine, alanine, aspartic acid and glutamic acid, compared with polished rice, brown rice and puffed pre-germinated brown rice. (3) Extrusion cooking was shown to sterilize the germinated brown rice by the incubation test, which would lead to the development of consumer-oriented rice products in terms of food safety. (4) The wheat bread prepared with 30% of the puffed pre-germinated brown rice contained more GABA, free sugars, such as maltose, compared with the ordinary wheat bread. The extrudate bread was shown to be sweeter ( P 0.05 ) and equivalently palatable ( P 0.05 ) as a result of organoleptic test. These results show that novel foodstuff from the extruded pre-germinated brown rice would be acceptable to consumers or the food industry as a promising foodstuff containing more nutritional and bio-functional components than ordinary rice products.
250 citations