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      Strategy for Screening of Antioxidant Compounds from Two Ulmaceae Species Based on Liquid Chromatography-Mass Spectrometry

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          Abstract

          Liquid chromatography-mass spectrometry (LC-MS)-based untargeted metabolomics implies that annotated metabolites can serve as potential markers of the associated bioactivities of plant extracts. Firstly, we selected Aphananthe aspera and Zelkova serrata (Family: Ulmaceae) from 16 Korean plant species based on their distinct principal component analysis (PCA) patterns in LC-MS datasets and antioxidant activity assays. Further, we chose 40% solid-phase extraction (SPE) extracts of the two species displaying the highest antioxidant activities coupled with distinct PCA patterns. Examining the metabolite compositions of the 40% SPE extracts, we observed relatively higher abundances of quercetin, kaempferol, and isorhamnetin O-glucosides for A. aspera, whereas quercetin, isorhamnetin O-glucuronides, and procyanidin dimer were relatively higher in Z. serrata. These metabolites were clearly distinguished in pathway map and displayed strong positive correlations with antioxidant activity. Further, we performed preparative high-performance liquid chromatography (prep-HPLC) analysis coupled with the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) assay to validate their functional correlations. As a result, quercetin O-sophoroside was determined as the main antioxidant in A. aspera, while isorhamnetin O-glucuronide and procyanidin dimer were the primary antioxidants in Z. serrata. The current study suggests that the LC-MS-based untargeted metabolomics strategy can be used to illuminate subtle metabolic disparities as well as compounds associated with bioactivities.

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          Antioxidant activity and phenolic compounds of ginger (Zingiber officinale Rosc.) determined by HPLC-MS/MS

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            Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

            Nine flavonoids were isolated and characterized from the leaves of Zanthoxylum bungeanum. Their structures were elucidated by spectroscopic techniques as quercetin (1), afzelin (2), quercitrin (3), trifolin (4), quercetin-3-O-β-D-glucoside (5), isorhamnetin 3-O-α-L-rhamnoside (6), hyperoside (7), vitexin (8) and rutin (9). All compounds were isolated from the leaves of Z. bungeanum for the first time. Five compounds (2, 4, 5, 6 and 8) were found for the first time in the genus Zanthoxylum. To learn the mechanisms underlying its health benefits, in vitro (DPPH, ABTS, FRAP and lipid peroxidation inhibition assays) and in vivo (protective effect on Escherichia coli under peroxide stress) antioxidant activities of the nine flavonoids were measured. Quercetin and quercetin glycosides (compounds 1, 3, 5, 7, 9) showed the highest antioxidant activity. Structure-activity relationships indicated that the -OH in 4′ position on the B ring and the -OH in 7 position on the A ring possessed high antioxidant activity; B ring and/or A ring with adjacent -OH groups could greatly increase their antioxidant ability. Also, due to the different structures of various flavonoids, they will certainly exhibit different antioxidant capacity when the reactions occur in solution or in oil-in-water emulsion. These findings suggest that Z. bungeanum leaves may have health benefits when consumed. It could become a useful supplement for pharmaceutical products and functional food ingredients in both nutraceutical and food industries as a potential source of natural antioxidants.
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              Metabolite profiling of the short-term responses of rice leaves (Oryza sativa cv. Ilmi) cultivated under different LED lights and its correlations with antioxidant activities.

              Metabolite profiling of rice leaves (Oryza sativa cv. Ilmi) was performed to investigate the short-term responses to different light-emitting diode (LED) lights, blue (B), green (G), red (R), white (W), shade (S), by using gas chromatography-ion trap-mass spectrometry (GC-IT-MS) and ultra-performance liquid chromatography-quadrupole-time-of-flight-mass spectrometry (UPLC-Q-TOF-MS) with multivariate analysis. Clear grouping patterns of each light-grown sample, except G and W, were shown in partial least squares-discriminant analysis (PLS-DA). Thirty-two primary metabolites and eleven secondary metabolites were selected and visualized using heatmap. Antioxidant activities of rice leaves followed the order B=W=G>R>S and isoorientin-2''-O-glucoside, isovitexin-2''-O-glucoside, isoorientin-2''-O-(6'''-ρ-coumaroyl)-glucoside, and isoscoparin-2''-O-glucoside showed similar relative differences and had higher Pearson's correlation coefficients than other metabolites in correlation network. According to the orthogonal projection to latent structures-discriminant analysis (OPLS-DA) between B and R, the levels of amino acids, organic acids, fatty acids, and flavonoid glycosides were relatively high in B, whereas the glucose and fructose levels were high in R.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                23 July 2018
                July 2018
                : 23
                : 7
                : 1830
                Affiliations
                [1 ]Department of Bioscience and Biotechnology, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea; tomkazasky@ 123456naver.com (J.Y.W.); syson119@ 123456naver.com (S.Y.S.); duly123@ 123456naver.com (S.L.); singhdigar@ 123456gmail.com (D.S.)
                [2 ]National Institute of Biological Resources, Environmental Research Complex, Incheon 22689, Korea; lsr57@ 123456korea.kr (S.L.); jslee001@ 123456korea.kr (J.S.L.)
                Author notes
                [* ]Correspondence: chlee123@ 123456konkuk.ac.kr ; Tel.: +82-2-444-4290; Fax: +82-2-455-4291
                Article
                molecules-23-01830
                10.3390/molecules23071830
                6100396
                30041442
                0c727662-ab04-4519-a7fb-145aca9c0881
                © 2018 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 12 July 2018
                : 20 July 2018
                Categories
                Article

                aphananthe aspera,zelkova serrata,metabolite profiling,lc-ms,antioxidant activity,preparative hplc combination

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