A New flavonolignan from the aerial Parts of Oryza sativa L. inhibits nitric oxide production in RAW 264.7 macrophage cells

Jeong, Rak Hun; Lee, Dong Hoon; Cho, Jin Gyeong; Lee, Sang Min; Kang, Hee Cheol; Seo, Woo Duck; Kang, Hwang Won; Kim, Ji Young; Baek, Nam In

doi:10.1007/bf03253174

Cited by 29 publications

(17 citation statements)

References 11 publications

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“…The most common form is tricin 7-O-glucopyranoside, which is found in taxonomically diverse species including sugarcane (Saccharum officinarum; Mabry et al, 1984), Phoenix hanceana (Lin et al, 2009), Sasa borealis (Park et al, 2007), Lygodium japonicum (Zhang et al, 2008a), and Ficus stenophylla (Zhang et al, 2008b). Our metabolite profiling of rice seedlings showed that tricin is mostly present as O-linked flavanolignans and their O-glycosides, which were previously identified in several rice varieties (Jeong et al, 2011(Jeong et al, , 2014Yang et al, 2013) and other grass species (Bouaziz et al, 2002;Wenzig et al, 2005). The different tricin-type flavanolignans were reported to exhibit a range of health-beneficial properties, such as antioxidation, antiinflammation, cardiovascular protection, and induction of tumor cell apoptosis (Chang et al, 2010;Jeong et al, 2011;Mohanlal et al, 2011Mohanlal et al, , 2013.…”

Section: Cyp93b11) Involved In Root Nodulationmentioning

confidence: 69%

“…Our metabolite profiling of rice seedlings showed that tricin is mostly present as O-linked flavanolignans and their O-glycosides, which were previously identified in several rice varieties (Jeong et al, 2011(Jeong et al, , 2014Yang et al, 2013) and other grass species (Bouaziz et al, 2002;Wenzig et al, 2005). The different tricin-type flavanolignans were reported to exhibit a range of health-beneficial properties, such as antioxidation, antiinflammation, cardiovascular protection, and induction of tumor cell apoptosis (Chang et al, 2010;Jeong et al, 2011;Mohanlal et al, 2011Mohanlal et al, , 2013. However, the biosynthesis of flavanolignans in plants is not well understood.…”

Section: Cyp93b11) Involved In Root Nodulationmentioning

confidence: 87%

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Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

et al. 2014

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Flavones are a major class of flavonoids with a wide range of physiological functions in plants. They are constitutively accumulated as C-glycosides and O-linked conjugates in vegetative tissues of grasses. It has long been presumed that the two structural modifications of flavones occur through independent metabolic routes. Previously, we reported that cytochrome P450 93G2 (CYP93G2) functions as a flavanone 2-hydroxylase (F2H) that provides 2-hydroxyflavanones for C-glycosylation in rice (Oryza sativa). Flavone C-glycosides are subsequently formed by dehydratase activity on 2-hydroxyflavanone C-glycosides. On the other hand, O-linked modifications were proposed to proceed after the flavone nucleus is generated. In this study, we demonstrate that CYP93G1, the closest homolog of CYP93G2 in rice, is a bona fide flavone synthase II (FNSII) that catalyzes the direct conversion of flavanones to flavones. In recombinant enzyme assays, CYP93G1 desaturated naringenin and eriodictyol to apigenin and luteolin, respectively. Consistently, transgenic expression of CYP93G1 in Arabidopsis (Arabidopsis thaliana) resulted in the accumulation of different flavone O-glycosides, which are not naturally present in cruciferous plants. Metabolite analysis of a rice CYP93G1 insertion mutant further demonstrated the preferential depletion of tricin O-linked flavanolignans and glycosides. By contrast, redirection of metabolic flow to the biosynthesis of flavone C-glycosides was observed. Our findings established that CYP93G1 is a key branch point enzyme channeling flavanones to the biosynthesis of tricin O-linked conjugates in rice. Functional diversification of F2H and FNSII in the cytochrome P450 CYP93G subfamily may represent a lineage-specific event leading to the prevalent cooccurrence of flavone C-and O-linked derivatives in grasses today.

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Section: Cyp93b11) Involved In Root Nodulationmentioning

confidence: 69%

Section: Cyp93b11) Involved In Root Nodulationmentioning

confidence: 87%

Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

et al. 2014

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“…They were respectively identified as 4′,5,7-trihydroxy-3′,5′-dimethoxyflavone, tricin (1), tricin-4′-O-(threo-β-guaiacylglyceryl) ether, salcolin A (2), tricin-4′-O-(erythro-β-guaiacylglyceryl) ether, salcolin B (3), and tricin-4′-O-[threo-β-guaiacyl-(7″-O-methyl)-glyceryl] ether, salcolin C (4) based on interpretation of the spectroscopic data, including NMR, MS, IR, and were confirmed by comparison of the data with those reported in the literature. [21][22][23] All compounds were isolated for the first time from Z.latifolia.…”

Section: Isolation and Identification Of Tricin Derivativesmentioning

confidence: 99%

“…To determine the cytotoxicity of the components, cell viability was determined by the MTT assay, 23) in which active mitochondria reduce MTT into formazan dye. RBL-2H3 cells were seeded at a density of 3 × 10 4 cells/well in 96-well microplates.…”

Section: Determination Of Cell Viabilitymentioning

confidence: 99%

Tricin derivatives as anti-inflammatory and anti-allergic constituents from the aerial part of Zizania latifolia

Lee

Baek

Eun

et al. 2015

Bioscience, Biotechnology, and Biochemistry

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Methanol extract of Zizania latifolia was partitioned with EtOAc, n-BuOH, and H2O. From the EtOAc layers, a new flavonolignan along with a known flavone and three known flavonolignans, tricin (1), salcolin A (2), salcolin B (3), and salcolin C (4), were isolated through repeated silica gel and ODS column chromatography. The chemical structure of the new flavonolignan was determined to be tricin-4′-O-[erythro-β-guaiacyl-(7″-O-methyl)-glyceryl] ether and was named salcolin D (5) based on physicochemical and spectroscopic data, including FT-NMR and ESI-MS. All compounds were isolated for the first time from this plant. Compounds 2–5, tricin derivatives, all exhibited higher anti-inflammatory and anti-allergy activities than tricin. In particular, salcolin D (5) was shown to have the strongest inhibitory activity against LPS-induced NO production in RAW 264.7 cells as well as β-hexosaminidase release in IgE-sensitized RBL-2H3 cells. These results suggest that the presence of tricin derivatives conveys allergy and inflammation treatment ability to Z. latifolia.

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“…[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%

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

et al. 2016

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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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A New flavonolignan from the aerial Parts of Oryza sativa L. inhibits nitric oxide production in RAW 264.7 macrophage cells

Cited by 29 publications

References 11 publications

Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

Tricin derivatives as anti-inflammatory and anti-allergic constituents from the aerial part of Zizania latifolia

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

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