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      Novel Phenolic Constituents of Pulmonaria officinalis L. LC-MS/MS Comparison of Spring and Autumn Metabolite Profiles

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          Abstract

          Lungwort ( Pulmonaria officinalis L., Boraginaceae) is considered to possess therapeutic properties and it has been traditionally used as a remedy against various lung disorders in many countries. Nevertheless, very few data concerning its phytochemical composition are available. This research aims to provide a detailed description of specialized metabolites from the aerial parts of lungwort. Nine previously undescribed and 36 known phenolic compounds were detected in the 50% methanolic extract. Following multistep preparative procedures, structures of newly discovered compounds were determined using one- and two-dimensional techniques of NMR spectroscopy. Among the identified compounds were caffeic acid esters with aliphatic hydroxycarboxylic acids, conjugates of dicaffeic acid with rosmarinic acid, and previously unknown isomers of isosalvianolic acid A and yunnaneic acid E, as well as other lignans. Concentrations of all identified phenolic derivatives in the investigated herbal material were estimated using a method based on liquid chromatography with high-resolution mass spectrometry detection. Seasonal changes in the concentration of metabolites were also investigated using targeted and untargeted metabolomics techniques.

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          MetaboAnalyst 4.0: towards more transparent and integrative metabolomics analysis

          Jasmine Chong, Othman Soufan, Carin Li … (2018)
          Abstract We present a new update to MetaboAnalyst (version 4.0) for comprehensive metabolomic data analysis, interpretation, and integration with other omics data. Since the last major update in 2015, MetaboAnalyst has continued to evolve based on user feedback and technological advancements in the field. For this year's update, four new key features have been added to MetaboAnalyst 4.0, including: (1) real-time R command tracking and display coupled with the release of a companion MetaboAnalystR package; (2) a MS Peaks to Pathways module for prediction of pathway activity from untargeted mass spectral data using the mummichog algorithm; (3) a Biomarker Meta-analysis module for robust biomarker identification through the combination of multiple metabolomic datasets and (4) a Network Explorer module for integrative analysis of metabolomics, metagenomics, and/or transcriptomics data. The user interface of MetaboAnalyst 4.0 has been reengineered to provide a more modern look and feel, as well as to give more space and flexibility to introduce new functions. The underlying knowledgebases (compound libraries, metabolite sets, and metabolic pathways) have also been updated based on the latest data from the Human Metabolome Database (HMDB). A Docker image of MetaboAnalyst is also available to facilitate download and local installation of MetaboAnalyst. MetaboAnalyst 4.0 is freely available at http://metaboanalyst.ca.
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            Functional roles of flavonoids in photoprotection: new evidence, lessons from the past.

            Francesco Ferrini, Massimiliano Tattini, Giovanni Agati … (2013)
            We discuss on the relative significance of different functional roles potentially served by flavonoids in photoprotection, with special emphasis to their ability to scavenge reactive oxygen species (ROS) and control the development of individual organs and whole plant. We propose a model in which chloroplast-located flavonoids scavenge H2O2 and singlet oxygen generated under excess light-stress, thus avoiding programmed cell death. We also draw a picture in which vacuolar flavonoids in conjunction with peroxidases and ascorbic acid constitute a secondary antioxidant system aimed at detoxifying H2O2, which may diffuse out of the chloroplast at considerable rates and enter the vacuole following excess light stress-induced depletion of ascorbate peroxidase. We hypothesize for flavonols key roles as developmental regulators in early and current-day land-plants, based on their ability to modulate auxin movement and auxin catabolism. We show that antioxidant flavonoids display the greatest capacity to regulate key steps of cell growth and differentiation in eukaryotes. These regulatory functions of flavonoids, which are shared by plants and animals, are fully accomplished in the nM concentration range, as likely occurred in early land plants. We therefore conclude that functions of flavonoids as antioxidants and/or developmental regulators flavonoids are of great value in photoprotection. We also suggest that UV-B screening was just one of the multiple functions served by flavonoids when early land-plants faced an abrupt increase in sunlight irradiance. Copyright © 2013 Elsevier Masson SAS. All rights reserved.
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              Polyphenols and antioxidant capacity of Bulgarian medicinal plants.

              D Ivanova, D Gerova, T Chervenkov … (2005)
              Extracts of 21 plants used in Bulgarian phytotherapy for the treatment of respiratory, gastrointestinal and other inflammatory disorders were screened in vitro for antioxidant activity and phenolic compounds content. Plant extracts were prepared as herbal teas following the ethnic use. The water-phase TEAC (Trolox equivalent antioxidant capacity) of the teas were compared to that of the famous tea-like beverages mate, rooibos and honeybush, and to that of green and black tea, well known for their high antioxidant potential. The content of total phenolics in the teas was determined spectrometrically according to the Folin-Ciocalteu procedure and calculated as quercetin equivalents (QE). Seven Bulgarian medicinal plants were with high phenolics content and antioxidant properties: Pulmonaria officinalis L. (Boraginaceae) (TEAC 2.02+/-0.14 mM/QE 673.39+/-9.92 microM), Hypericum perforatum L. (Hypericaceae) (TEAC 3.75+/-0.14 mM/QE 881.93+/-6.68 microM), Agrimonia eupatoria L. (Rosaceae) (TEAC 3.76+/-0.5mM/QE 702.29+/-6.82 microM), Origanum vulgare L. (Lamiaceae) (TEAC 5.87+/-0.2mM/QE 1653.61+/-11.52 microM), Melissa officinalis L. (Lamiaceae) (TEAC 4.06+/-0.31 mM/QE 1370.09+/-41.38 microM), Rubus sp. diversa (Rosaceae) (TEAC 4.23+/-0,12 mM/QE 608.95+/-5.95 microM), Cotinus coggygria Scop. (Anacardiaceae) (TEAC 7.05+/-0.19 mM/QE 923.33+/-14.19 microM). Therefore, Bulgarian herbs can be considered to be a rich source of water-soluble antioxidants and/or phenolic compounds as compared to studied foreign plants.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 06 September 2018
                Publication date Collection: September 2018
                Volume: 23
                Issue: 9
                Electronic Location Identifier: 2277
                Affiliations
                [1 ]Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation—State Research Institute, Czartoryskich 8, 24-100 Puławy, Poland; lpecio@ 123456iung.pulawy.pl (Ł.P.); jmoldoch@ 123456iung.pulawy.pl (J.M.); mkowalczyk@ 123456iung.pulawy.pl (M.K.)
                [2 ]Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, Chodzki Str.1, 20-093 Lublin, Poland; aludwiczuk@ 123456pharmacognosy.org
                Author notes
                [* ]Correspondence: jkrzyzanowska@ 123456iung.pulawy.pl ; Tel.: +48-81-4786-881
                Author information
                https://orcid.org/0000-0002-7407-6716
                https://orcid.org/0000-0003-1108-613X
                Article
                Publisher ID: molecules-23-02277
                DOI: 10.3390/molecules23092277
                PMC ID: 6225171
                PubMed ID: 30200600
                SO-VID: c32a272e-ccf4-4086-9618-8b429f3b5c16
                Copyright © © 2018 by the authors.
                License:

                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
                Date received : 30 July 2018
                Date accepted : 04 September 2018
                Categories
                Subject: Article

                Keywords: pulmonaria officinalis,pulmonariae herba,lungwort,danshensu/caffeic acid/rosmarinic acid derivatives,hr-qtof/ms,nmr,cd,seasonal variability,metabolite profiling,multivariate analyses
                Data availability:
                Keywords: pulmonaria officinalis, pulmonariae herba, lungwort, danshensu/caffeic acid/rosmarinic acid derivatives, hr-qtof/ms, nmr, cd, seasonal variability, metabolite profiling, multivariate analyses

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