New flavonolignan glucoside from the aerial parts of Oryza sativa

Jeong, Rak-Hun; Lee, Dae-Young; Cho, Jin‐Gyeong; Seo, Kyeong‐Hwa; Lee, Jae-Woong; Seo, Woo-Duck; Kang, Hee-Cheol; Kim, Geum-Soog; Noh, Hyung-Jun; Lee, Youn‐Hyung; Baek, and Nam-In

doi:10.1007/s10600-014-0809-z

Cited by 11 publications

(3 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

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

et al. 2014

View full text Add to dashboard Cite

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.

show abstract

Section: Cyp93b11) Involved In Root Nodulationmentioning

confidence: 69%

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

et al. 2014

View full text Add to dashboard Cite

show abstract

“…The relative configuration of chiral carbons, C-7'' and C-8'', in compound ( 4 ) was deduced to be threo type from the coupling constant ( J = 6.0 Hz) between the oxygenated methine signals H-7'' (δ H 5.89) and H-8'' (δ H 5.19). It was reported that the J H -7'',8'' coupling constant of proton resonance in the guaiacylglyceryl moiety can be used to distinguish between the erythro and threo forms, with J values of 4.0–5.0 and 6.0–7.0 Hz, respectively [ 9 , 10 , 11 ]. The 13 C-NMR spectrum showed 33 carbon signals including three methoxy carbons [δ 52.3 (C-3', 5'-OCH 3 ) and 56.6 (C-3''-OCH 3 )], confirming that compound 4 was a flavonoid with a phenylpropanoid moiety and hexose moiety.…”

Section: Resultsmentioning

confidence: 99%

New Flavonolignan Glycosides from the Aerial Parts of Zizania latifolia

Lee

Baek

et al. 2015

Molecules

View full text Add to dashboard Cite

Two new flavonolignan glycosides, tricin-4'-O-(threo-β-guaiacylglyceryl) ether 7''-O-β-d-glucopyranose (4) and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether 7''-O-β-d-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with tricin-7-O-β-d-glucopyranose (1), tricin-4'-O-(threo-β-guaiacylglyceryl) ether 7-O-β-d-glucopyranose (2), and tricin-4'-O-(erythro-β-guaiacylglyceryl) ether 7-O-β-d-glucopyranose (3). Their structures were identified on the basis of spectroscopic techniques, including HR-ESI/MS, 1D-NMR (1H, 13C, DEPT), 2D-NMR (gCOSY, gHSQC, gHMBC), and IR spectroscopy.

show abstract

“…Sugar content was removed from the methanol extract by dissolving the residual concentrate in least amount of distilled water followed by addition of excess absolute ethanol. Fifty grams of dry concentrate were loaded on 750 g polyamide 6 column (5 cm W. x 120 cm L.) which was then eluted using water then H2O/MeOH mixtures with 20% stepwise decreasing polarity, that yielded 34 fractions of 500 ml each, and similar PC fractions were combined together affording into five major collective fractions; I (7 g) from 100% H2O (1-5), II (3.6 g) from 20% MeOH/H2O (6-12), III (1.2 g) from 40% MeOH/H2O (13)(14)(15)(16)(17)(18)(19)(20), IV (1.8 g) from 60-80% MeOH/H2O (21-29) and V (4 g) from pure MeOH (30-34). The interesting biological (antioxidant and cytotoxic) activities of fractions II, III and IV were encouraging for further processing of these fractions mainly by successive column chromatography on Sephadex and preparative paper chromatography using different solvent systems S1 (n-Butanol: Acetic acid: Water 4: 1: 5) and S2 (acetic acid: water 15:85).…”

Section: Extraction and Isolation Of Phenolics From N Ritchiana Leavesmentioning

confidence: 99%

Flavonolignans and Biological Activity of Nannorrhops ritchiana Leaves

Essa

Mohamed

Haggag

et al. 2017

Journal of Advanced Pharmacy Research

View full text Add to dashboard Cite

Objectives: This study aimed at isolating the polyphenolic compounds of 70% methanol extract of Nannorrhops ritchiana Griff. leaves and assaying the antioxidant and cytotoxic activities of the extract and main fractions. Methods: The methanol extract of the leaves of N. ritchiana was chromatographically fractionated using a bioactivity-guided approach. The isolated compounds were spectroscopically elucidated by UV, MS, 1 H/ 13 C NMR and 2D NMR spectroscopic techniques. The radical scavenging activity of the methanol extract and its fractions was evaluated using DPPH (2,2-Diphenyl-1-picrylhydrazyl) radical scavenging assay and their cytotoxic activity was assayed using SRB (3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyltetrazolium bromide) test against human hepatocellular liver carcinoma (HepG2), human alveolar adenocarcinoma (A549) and human prostate carcinoma (PC3) cell lines. Results: Eight compounds were isolated and identified for the first time from the leaves of N. ritchiana, comprising five flavonolignans; Indocalatin A (4) which is a rare compound that has been reported only once in nature, 9″-O-glucopyranosyl Salcolin A (5), 9″-O-glucopyranosyl Salcolin B (6) together with their aglycones, Salcolin A (7) and Salcolin B (8) along with three flavone glycosides; Tricin-7-O-rutinoside (1), Orientin (2) and Isoorientin (3). The methanol extract of N. ritchiana showed antioxidant activity with SC50 39.4 ± 1.06 μg/ml, while fraction II showed significant effect with SC50 of 6.1 ± 0.24 μg/ml in comparison with ascorbic acid (SC50 1.8 ± 0.35 μg/ml). The methanol extract and the fraction III showed a promising cytotoxic activity against selected cell lines especially the A549 with IC50 9.5 ± 1.98 μg/ml and HepG2 with IC50 8.15 ± 1.3 μg/ml, respectively. Conclusion: N. ritchiana leaf methanol extract is a new source of biologically active compounds, including flavonolignans.

show abstract

New flavonolignan glucoside from the aerial parts of Oryza sativa

Cited by 11 publications

References 5 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

New Flavonolignan Glycosides from the Aerial Parts of Zizania latifolia

Flavonolignans and Biological Activity of Nannorrhops ritchiana Leaves

Contact Info

Product

Resources

About