DPPH Radical Scavenging Activity of Tricin and Its Conjugates Isolated from “Njavara” Rice Bran: A Density Functional Theory Study

Ajitha, M.; Mohanlal, Smitha; Suresh, Cherumuttathu H.; Jayalekshmy, A.

doi:10.1021/jf204826e

Cited by 42 publications

(31 citation statements)

References 44 publications

(68 reference statements)

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“…6,8) Flavonoids accumulate in the rice bran of black rice cultivars but not in popular white rice cultivars. 16,18,22) This profiling showed that the level of C-glycosylflavonoids (20-23) is higher in Habataki rice than that in Nipponbare. It has been reported that the Indica rice variety exhibits higher C-glycosylflavonoid production than the Japonica variety.…”

Section: Resultsmentioning

confidence: 93%

“…[15][16][17][18][19][20] Such metabolites exhibit properties beneficial to humans, including anti-tumor, 21) anti-inflammatory, 22) and anti-oxidant activities. 8) To improve the quality of rice plants, the organ-specific metabolic networks of primary and specialized metabolites were recently investigated using metabolite profiling based on liquid chromatography (LC)-MS. 19,[23][24][25][26][27][28] Metabolome-genome-wide association studies on rice have been increasingly attracting attention.…”

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confidence: 99%

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Metabolome Analysis of <i>Oryza sativa</i> (Rice) Using Liquid Chromatography-Mass Spectrometry for Characterizing Organ Specificity of Flavonoids with Anti-inflammatory and Anti-oxidant Activity

Yang

Nakabayashi

Mori

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oryza sativa L. (rice) is an important staple crop across the world. In the previous study, we identified 36 specialized (secondary) metabolites including 28 flavonoids. In the present study, a metabolome analysis using liquid chromatography-mass spectrometry was conducted on the leaf, bran, and brown and polished rice grains to better understand the distribution of these metabolites. Principal component analysis using the metabolome data clearly characterized the accumulation patterns of the metabolites. Flavonoids, e.g., tricin, tricin 7-O-rutinoside, and tricin 7-O-β-D-glucopyranoside, were mainly present in the leaf and bran but not in the polished grain. In addition, anti-inflammatory and anti-oxidant activity of the metabolites were assayed in vitro. Tricin 4′-O-(erythro-β-guaiacylglyceryl)ether and isoscoparin 2″-O-(6‴-(E)-feruloyl)-glucopyranoside showed the strongest activity for inhibiting nitric oxide (NO) production and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging, respectively. Key words Oryza sativa; rice; specialized metabolite; anti-inflammatory; anti-oxidantPlants produce a wide range of chemically and biologically diverse specialized (secondary) metabolites. These metabolites play an important role in human health because they have nutritional and medicinal aspects. 1) Rice (Oryza sativa L.) is one of the most important staple crops and provides more than a fifth of the total calories consumed across the world.2)The major nutrient of rice is starch; minor nutrients include protein, lipid, fiber, vitamins, and minerals.3) Rice accumulates bioactive specialized metabolites, 4) such as phenylpropanoids, 5-9) quinolone and pyridine alkaloids, 10,11) terpenoids, [12][13][14] and flavonoids (quercetin, kaempferol, tricin, and their glycosides). [15][16][17][18][19][20] Such metabolites exhibit properties beneficial to humans, including anti-tumor, 21) anti-inflammatory, 22) and anti-oxidant activities. 8) To improve the quality of rice plants, the organ-specific metabolic networks of primary and specialized metabolites were recently investigated using metabolite profiling based on liquid chromatography (LC)-MS.19,23-28) Metabolome-genome-wide association studies on rice have been increasingly attracting attention. 25,29) There are two primary types of rice grown in the world (i.e., the Indica and Japonica varieties). The Habataki cultivar is an Indica variety with higher yields, while the Koshihikari cultivar is a Japonica variety of better quality. In the previous study, 36 metabolites were isolated from the leaves of the Habataki cultivar.20) It is important to investigate organ specificity and benefits of the metabolites for application studies to improve the quality of rice plants. Here, to better understand the organ specificity of the metabolites and their benefits to humans, we performed the metabolite profiling of the leaf, bran, and brown and polished rice grains, using liquid chromatography-quadrupole time-of-flight (LC-QTOF)-MS. In addition, nitric oxide (NO) assay and 1,1-diphe...

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Section: Resultsmentioning

confidence: 93%

mentioning

confidence: 99%

Metabolome Analysis of <i>Oryza sativa</i> (Rice) Using Liquid Chromatography-Mass Spectrometry for Characterizing Organ Specificity of Flavonoids with Anti-inflammatory and Anti-oxidant Activity

Yang

Nakabayashi

Mori

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…values was estimated to be between 3.0% and 4.7% for each extract. Polyphenols are also included in rice bran (Ajitha, Mohanlal, Suresh, & Jayalekshmy, ; Nakornriab, Sriseadka, & Wongpornchai, ). These polyphenols may also contribute to ArO• scavenging.…”

Section: Discussionmentioning

confidence: 99%

Kinetic Study of the Scavenging Reaction of the Aroxyl Radical by Eight Kinds of Vegetable Oils in Solution

Mukai

Bandoh

Ito

et al. 2018

J Americ Oil Chem Soc

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A detailed kinetic study was performed for the reaction of the aroxyl radical (ArO • ) with eight vegetable oils 1-8, which contain different concentrations of α-, β-, γ-, and δ-tocopherols and -tocotrienols (-Tocs and -Toc-3s). The second-order rate constants (k s ) and aroxyl radical absorption capacity (ARAC) values for the reaction of ArO • with vegetable oils 1-8 (rice bran 1, perilla 2, rapeseed 3, safflower 4, grape seed 5, sesame 6, extra virgin olive 7, and olive oils 8) were measured in ethanol/chloroform/D 2 O (50:50:1, v/v/ v) solution at 25 C using stopped-flow spectrophotometry. The k s value (16.1 × 10 −3 L g −1 s −1 ) of rice bran oil 1 with the highest activity was 8.0 times larger than that (2.02 × 10 −3 ) of olive oil 8 with the lowest activity. The concentrations (in mg 100 g −1 ) of α-, β-, γ-, and δ-Tocs and -Toc-3s contained in the vegetable oils 1-8 were determined using high performance liquid chromatography-mass spectrometry/mass spectrometry (HPLC-MS/MS). From these results, it was clarified that the ArO • -scavenging rates (k s ) (i.e., the relative ARAC value) obtained for the vegetable oils 1-8 may be well explained as the sum of the product P k AOH-i s AOH-i ½ =10 5 È É of the rate constant (k AOH-i s ) and the concentration ([AOH-i]/10 5 ) of AOH-i (Tocs and Toc-3s) included in vegetable oils. The results suggest that the ARAC assay method might be used in the evaluation of antioxidant activity of general food extracts.

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“…The 1 H NMR data allow some conclusions on the chelation site: rutin chelates metal ions via 3c,4c-phenolic hydrogen, and in return the metal ions remove phenolic hydrogen from rutin [24][25][26]. The proton signals of Tin(II)-rutin complex are shifted to high field relative to its ligand, especially the G values of 2c-, 5c-, and 6c-H.…”

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confidence: 91%

Synthesis, Spectral and Antioxidant Properties of Tin(II)-Rutin Complex

et al. 2014

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Rutin is one of the most common flavonoids present in nature that has a wide range of biological properties. A Tin(II)-rutin complex was synthesized from the raw material rutin and SnCl 2 in an alkaline solution. The complex was characterized by UV-vis, IR, 1 H NMR, and 13 C NMR spectroscopy. We evaluated the free radical scavenging activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method, and the results showed that pure rutin was more effective than the Tin(II)-rutin complex in terms of antioxidant activity. Supplementing diet by foods rich in rutin and other flavonoids, such as vegetables and fruits, may contribute to removing free radicals and heavy metal ions in our body.Tinplate, commonly known as tin-plated steel sheet, is a kind of cold-rolled low-carbon steel sheet coated with pure tin on both sides. This material combines the durable strength of steel with the corrosion resistance of tin in one. These characteristics are the reasons why tinplate is widely used in the manufacture of rigid containers, especially for food and beverage packaging. Normally the concentration of tin in the majority of foods should be less than 1 part per million (ppm); however, in canned foods, especially those with an acidic pH, noticeably higher levels or more may be found [e.g., 100-500 ppm (0.01-0.05%)]. Regular consumption of these foods will cause symptoms of tin poisoning, such as vomiting, diarrhea, and anorexia [1].Chelation therapy is the preferred method for reducing the heavy metal induced toxicity. Chelating agents tightly bind to toxic metal ions to form complex structures that are easily excreted from the body [2]. Flavonoids are polyphenolic natural products widely distributed in plant foods, with a wide range of biological activities and pharmacological properties such as cardiovascular protection, anti-cancer, anti-ulcer, anti-oxidation, anti-viral, and anti-inflammatory; in addition, flavonoids are also natural antioxidants, free radical scavengers, and metal chelators [3]. Rutin is one of the most common flavonoids present in nature that has a wide range of biological properties, such as anti-inflammatory [4], anticancer [5], antioxidant [6], and so on. Rutin is an effective metal chelator [7, 8]. The complexation of metal cations by rutin has already been reported for a large number of metals: Zn (II), Al (III) [9], Cu (II) [10], Co (II) [11], Fe (II) [12], Fe (III) [13], Mn (II) [14], V (II) [15], U (II) [16], and Au (III) [17]. Rutin has attracted the attention of many researchers because of these special properties [18]. Supplementing regular diet with foods rich in rutin and other flavonoids, such as ginkgo biloba and buckwheat, may contribute to removing free radicals and heavy metal ions in our body [19,20].The purpose of this investigation was to study the chelating properties of rutin with tin cations [Sn(II)] and investigate the variation in antioxidant properties of rutin after chelation.The UV-vis spectrum of free rutin and Tin(II)-rutin complex in MeOH is reported in Fig. 1. Rutin exhibit...

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DPPH Radical Scavenging Activity of Tricin and Its Conjugates Isolated from “Njavara” Rice Bran: A Density Functional Theory Study

Cited by 42 publications

References 44 publications

Metabolome Analysis of <i>Oryza sativa</i> (Rice) Using Liquid Chromatography-Mass Spectrometry for Characterizing Organ Specificity of Flavonoids with Anti-inflammatory and Anti-oxidant Activity

Metabolome Analysis of <i>Oryza sativa</i> (Rice) Using Liquid Chromatography-Mass Spectrometry for Characterizing Organ Specificity of Flavonoids with Anti-inflammatory and Anti-oxidant Activity

Kinetic Study of the Scavenging Reaction of the Aroxyl Radical by Eight Kinds of Vegetable Oils in Solution

Synthesis, Spectral and Antioxidant Properties of Tin(II)-Rutin Complex

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