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1.
Food Chem ; 337: 127956, 2021 Feb 01.
Article in English | MEDLINE | ID: mdl-32919269

ABSTRACT

Even though γ-oryzanol (OZ) such as 24-methylenecycloartanyl ferulate (24MCAFA) is abundant in purified rice bran oil, we realized that the oil contained the prospect of two additional novels of OZ species. To identify this, we isolated and analyzed their chemical structures by using HPLC-UV-MS, NMR, and IR. We revealed for the first time that the oil had also contained cyclobranyl ferulate (CBFA) and cyclosadyl ferulate (CSFA) which are likely to be exist due to the isomerism of 24MCAFA under acid condition. OZ profile including CBFA and CSFA was roughly similar between commercial rice bran oils and processed foods containing the oils, suggesting that people might have often consumed CBFA and CSFA from rice bran oils and/or processed foods. Since different OZ species are known to have different functionality, this study opens the chance to explore more the contribution of CBFA and CSFA for human health and wellness.


Subject(s)
Phenylpropionates/chemistry , Rice Bran Oil/chemistry , Chromatography, High Pressure Liquid , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Phenylpropionates/isolation & purification
2.
Sci Rep ; 10(1): 14091, 2020 08 24.
Article in English | MEDLINE | ID: mdl-32839472

ABSTRACT

Although the stability of rice bran oil (RBO) has been showed on several studies, the factors which make it capable on maintaining its stability under thermal oxidation has not been sure yet. We hypothesized that its fatty acid composition [high composition of oleic acid (OA), lower composition of linoleic acid (LA) and α-linolenic acid (LnA)] and/or its antioxidant agents [γ-oryzanol (OZ)] and vitamin E [tocopherol (Toc), tocotrienol (T3)] might be the biggest factor. To prove the hypothesis, we thermally oxidized RBO under 40 °C for 17 days to mimic the harsh daily storage condition, and compared it with soybean oil (SO) and rapeseed oil (RPO) then monitoring their primary oxidation products [triacylglycerol hydroperoxide (TGOOH)] from easily oxidized fatty acid contained in triacylglycerol (TG) and the amount loss of antioxidant agents. As a result, RBO showed the lowest TGOOH/TG ratio, followed by RPO and SO. The superior stability RPO compared SO might occur due to because of the influence of the fatty acid profile (higher OA and lower LA). For RBO's case, besides its fatty acid profile, the existence of OZ and the synergistic effect of OZ and vitamin E might have a greater contribution in maintaining its stability under thermal oxidation.

4.
J Nutr Sci Vitaminol (Tokyo) ; 65(Supplement): S180-S184, 2019.
Article in English | MEDLINE | ID: mdl-31619625

ABSTRACT

γ-Oryzanol (OZ), a functional substance found in rice bran, consists of multiple molecular species. In both in vitro and in vivo studies, the researches exploring the various function of rice bran OZ have been conducted for a long time, and it has become clear that OZ has a lot of pharmaceutical activities. It is assumed that each type of OZ molecular species may have different effects. In contrast, the profile behaviour of OZ inside the body has not been fully understood. This article reviews the previous studies about the digestion, absorption, metabolism, and effects of rice bran OZ and also introduces the new method to evaluate the OZ metabolic fate by using high-performance liquid chromatography (HPLC) combined with tandem mass-spectrometry (MS/MS) which has higher selectivity and sensitivity.


Subject(s)
Digestion/drug effects , Intestinal Absorption/drug effects , Oryza/chemistry , Phenylpropionates/metabolism , Chromatography, High Pressure Liquid , Humans , Nutritive Value , Tandem Mass Spectrometry
5.
Sci Rep ; 9(1): 12572, 2019 08 29.
Article in English | MEDLINE | ID: mdl-31467350

ABSTRACT

γ-Oryzanol (OZ), which has a lot of beneficial effects, is a mixture of ferulic acid esters of triterpene alcohols (i.e., triterpene alcohol type of OZ (TTA-OZ)) and ferulic acid esters of plant sterols (i.e., plant sterol type of OZ (PS-OZ)). Although it has been reported that OZ is found in several kinds of cereal typified by rice, TTA-OZ (e.g., 24-methylenecycloartanyl ferulate (24MCA-FA)) has been believed to be characteristic to rice and has not been found in other cereals. In this study, we isolated a compound considered as a TTA-OZ (i.e., 24MCA-FA) from barley and determined the chemical structure using by HPLC-UV-MS, high-resolution MS, and NMR. Based on these results, we proved for the first time that barley certainly contains 24MCA-FA (i.e., TTA-OZ). During the isolation and purification of 24MCA-FA from barley, we found the prospect that a compound with similar properties to OZ (compound-X) might exist. To confirm this finding, the compound-X was also isolated, determined the chemical structure, and identified as a caffeic acid ester of 24-methylenecycloartanol (24MCA-CA), which has rarely been reported before. We also quantified these compounds in various species of barley cultivars and found for the first time the existence of 24MCA-FA and 24MCA-CA in various barley. Through these findings, it opens the possibility to use barley as a new source of 24MCA-FA and 24MCA-CA.


Subject(s)
Coumaric Acids/analysis , Hordeum/chemistry , Coumaric Acids/chemistry , Coumaric Acids/isolation & purification , Oryza/chemistry , Species Specificity
6.
Nutrients ; 11(1)2019 Jan 06.
Article in English | MEDLINE | ID: mdl-30621350

ABSTRACT

γ-Oryzanol (OZ), abundant in rice bran oil, has gained attention due to its physiological activities (e.g., lipid-lowering effects). However, the absorption and metabolism of orally ingested OZ have not yet been fully elucidated. In this study, diets containing normal or high contents of OZ were fed to obesity model mice for 8 weeks, and OZ concentrations in plasma and organs were analyzed by HPLC-MS/MS. To evaluate the relationship between OZ accumulation and lipid metabolism in vivo, lipid concentrations in the mice plasma and liver were also measured. As a result, the accumulation of intact OZ in plasma and organs was seen in mice fed diets containing OZ, where mice fed diets containing higher OZ contents demonstrated higher levels of OZ accumulation and lower amounts of plasma lipids. These results, in combination with our additional data from a single oral administration test, suggest the possibility that intact OZ, along with its metabolites (e.g., ferulic acid), is biologically-active.


Subject(s)
Lipid Metabolism/drug effects , Phenylpropionates/administration & dosage , Phenylpropionates/pharmacokinetics , Adipose Tissue/growth & development , Animals , Diet , Diet, High-Fat , Disease Models, Animal , Female , Fetal Development , Hypolipidemic Agents , Lipids/blood , Liver/chemistry , Male , Maternal-Fetal Exchange , Mice , Mice, Inbred C57BL , Obesity/etiology , Obesity/metabolism , Organ Size/drug effects , Phenylpropionates/analysis , Pregnancy , Rats , Rats, Sprague-Dawley , Soybean Oil/administration & dosage , Tissue Distribution
7.
Food Funct ; 7(12): 4816-4822, 2016 Dec 07.
Article in English | MEDLINE | ID: mdl-27878202

ABSTRACT

Although the beneficial effects (e.g., lipid-lowering activity) of γ-oryzanol (OZ), a mixture of ferulic acid esters of plant sterols and triterpene alcohols, have been extensively investigated, few studies have evaluated the absorption and metabolism of OZ. Moreover, it is unclear whether OZ, once ingested, is directly absorbed by the intestine into the bloodstream at a sufficient level to exhibit activity. Here, we prepared OZ concentrate from purified rice bran oil (Rice Oil OZ), determined the concentration of OZ in the preparation (cycloartenyl ferulate equivalent concentration; 52.2%), and then carried out chromatography-mass spectrometry analysis of plasma samples from mice after oral administration of Rice Oil OZ. The OZ concentrations of plasma from the control (vehicle-treated) mice were low (trace levels); however, at 5 h after a single oral administration of the Rice Oil OZ (600 mg per kg body weight), the levels significantly increased, reaching 17.6 ng mL-1 for cycloartenyl ferulate, 28.2 ng mL-1 for 24-methylenecycloartanyl ferulate isomers, 15.6 ng mL-1 for campesteryl ferulate, and 5.1 ng mL-1 for ß-sitosteryl ferulate, respectively, expressed in equivalence of cycloartenyl ferulate in plasma. These results provided the first mass spectrometric evidence suggesting that a portion of orally administered OZ is directly absorbed by the intestine and is present in the intact form in plasma. The presence of a significant amount of OZ in its intact form in plasma may explain the beneficial effects of OZ in vivo.


Subject(s)
Phenylpropionates/blood , Rice Bran Oil/administration & dosage , Rice Bran Oil/chemistry , Administration, Oral , Animals , Chromatography, High Pressure Liquid , Male , Mice , Mice, Inbred C57BL , Molecular Structure , Phenylpropionates/chemistry , Phenylpropionates/metabolism , Rice Bran Oil/metabolism , Tandem Mass Spectrometry
8.
BMJ Case Rep ; 20112011 Mar 03.
Article in English | MEDLINE | ID: mdl-22715249

ABSTRACT

Percutaneous endoscopic jejunostomy (PEJ) has been developed and is considered to be a better method than percutaneous endoscopic gastrostomy for preventing the occurrence of aspiration pneumonia. However, the incidence of other complications associated with this procedure is less clear. We herein report a rare case with a small intestinal intussusception due to a PEJ placement. In this case, a radiologic examination with gastrografin was useful to detect the typical findings of a small intestinal intussusception, a beak-like filling defect, and identify the location of the lesion. An endoscopic examination that was carefully performed with a thin scope was effective to observe the ischaemic change of the small intestine and immediately determine the indication for surgical treatment. This case highlights the necessity to carefully manage patients with a PEJ placement, considering the risk of small intestinal intussusceptions when the patient complains of symptoms that are suspicious for an intestinal obstruction.


Subject(s)
Intussusception/etiology , Jejunal Diseases/etiology , Jejunostomy/adverse effects , Jejunostomy/instrumentation , Aged, 80 and over , Endoscopy, Gastrointestinal , Humans , Jejunostomy/methods , Male
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