Nontargeted Screening for Flavonoids in Salicornia Plant by Reversed-Phase Liquid Chromatography–Electrospray Orbitrap Data-Dependent MS2/MS3

The Salicornia genus has great potential in agrifood industries because of its nutritional benefits related to its high content of antioxidant compounds, including flavonoids. A nontargeted method based on reversed-phase liquid chromatography–electrospray orbitrap data-dependent MS2/MS3 and the fragment ion search (FISh) strategy was developed to screen flavonoids in Salicornia plants. An extensive study of fragmentation of a set of flavonoid standards allowed for the definition of 15 characteristic fragment ions for flagging flavonoids in the plant matrix. The nontargeted analysis was applied to Salicornia europaea species and allowed for the annotation of 25 candidate flavonoids, including 14 that had not been reported previously. Structural prediction of two unreported flavonoids and their isomeric forms was based on an advanced data processing method using an in silico approach and in-house databases compiling flavonoid-specific chemical substitution. Finally, the method developed allowed for the optimization of extraction yields of flavonoids from the plant matrix.

[1]  C. Del Río,et al.  A Review on Polyphenols in Salicornia ramosissima with Special Emphasis on Their Beneficial Effects on Brain Ischemia , 2023, Nutrients.

[2]  Anita Šalić,et al.  Modern Techniques for Flavonoid Extraction—To Optimize or Not to Optimize? , 2022, Applied Sciences.

[3]  M. L. Clodoveo,et al.  Overview of the Polyphenols in Salicornia: From Recovery to Health-Promoting Effect , 2022, Molecules.

[4]  A. Raposo,et al.  Salicornia bigelovii, S. brachiata and S. herbacea: Their Nutritional Characteristics and an Evaluation of Their Potential as Salt Substitutes , 2022, Foods.

[5]  D. Pinto,et al.  Gall midge Baldratia salicorniae Kieffer, 1897 (Diptera: Cecidomyiidae) infestation on Salicornia europaea L. induces the production of specialized metabolites with biotechnological potential. , 2022, Phytochemistry.

[6]  Sanghyun Lee,et al.  Phenolic acids and flavonoids from Salvia plebeia and HPLC-UV profiling of four Salvia species , 2022, Heliyon.

[7]  Lunzhao Yi,et al.  Targeted identification of glycosylated flavones and isomers in green tea through integrated ion-filtering strategy and mass-fragmentation characteristics based on the UPLC–Q–Orbitrap–MS/MS platform , 2021, Food Chemistry.

[8]  C. Abdelly,et al.  Salicornia fruticosa L. and Portulaca oleracea L. antioxidants as affected by domestic cooking processes , 2021, International Journal of Gastronomy and Food Science.

[9]  A. Lillebø,et al.  Halophytes as novel marine products – A consumers’ perspective in Portugal and policy implications , 2021, Marine Policy.

[10]  M. J. Perea-Flores,et al.  An overview of the emerging trends of the Salicornia L. genus as a sustainable crop , 2021 .

[11]  I. Caçador,et al.  Impact of Drying Processes on the Nutritional Composition, Volatile Profile, Phytochemical Content and Bioactivity of Salicornia ramosissima J. Woods , 2021, Antioxidants.

[12]  C. Delerue-Matos,et al.  Salicornia ramosissima Bioactive Composition and Safety: Eco-Friendly Extractions Approach (Microwave-Assisted Extraction vs. Conventional Maceration) , 2021, Applied Sciences.

[13]  S. Nam,et al.  Chemical Structure and Biological Activities of Secondary Metabolites from Salicornia europaea L. , 2021, Molecules.

[14]  V. Cerdà,et al.  Recent, advanced sample pretreatments and analytical methods for flavonoids determination in different samples , 2021 .

[15]  V. de la Fuente,et al.  Bioactive Compounds in Salicornia patula Duval-Jouve: A Mediterranean Edible Euhalophyte , 2021, Foods.

[16]  Ana Paula da Fonseca Machado,et al.  Extraction of Flavonoids From Natural Sources Using Modern Techniques , 2020, Frontiers in Chemistry.

[17]  L. Barreira,et al.  Influence of cultivation salinity in the nutritional composition, antioxidant capacity and microbial quality of Salicornia ramosissima commercially produced in soilless systems. , 2020, Food chemistry.

[18]  A. Capriotti,et al.  A new software-assisted analytical workflow based on high-resolution mass spectrometry for the systematic study of phenolic compounds in complex matrices. , 2020, Talanta.

[19]  Feng Zhang,et al.  High-throughput mass spectrometry scheme for screening and quantification of flavonoids in antioxidant nutraceuticals. , 2019, Journal of chromatography. A.

[20]  Lunzhao Yi,et al.  Structural features guided "fishing" strategy to identification of flavonoids from lotus plumule in a self-built data "pool" by ultra-high performance liquid chromatography coupled with hybrid quadrupole-orbitrap high resolution mass spectrometry. , 2019, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[21]  G. Jerz,et al.  Preparative mass-spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high-speed countercurrent chromatography and off-line electrospray mass-spectrometry injection. , 2019, Journal of separation science.

[22]  L. Lucini,et al.  Metabolomic insights into the mechanisms underlying tolerance to salinity in different halophytes. , 2019, Plant physiology and biochemistry : PPB.

[23]  R. Larcher,et al.  Non-targeted glycosidic profiling of international wines using neutral loss-high resolution mass spectrometry. , 2018, Journal of chromatography. A.

[24]  B. H. Maia,et al.  Flavonoids: Classification, Biosynthesis and Chemical Ecology , 2017 .

[25]  N. Bandarra,et al.  Halophytes: Gourmet food with nutritional health benefits? , 2017 .

[26]  Maciej Stobiecki,et al.  Structural Characterization of Flavonoid Glycoconjugates and Their Derivatives with Mass Spectrometric Techniques , 2016, Molecules.

[27]  Seema Patel.  Salicornia: evaluating the halophytic extremophile as a food and a pharmaceutical candidate , 2016, 3 Biotech.

[28]  Daniel P Demarque,et al.  Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products. , 2016, Natural product reports.

[29]  H. Masjuki,et al.  Macroalgae and microalgae as a potential source for commercial applications along with biofuels production: A biorefinery approach , 2016 .

[30]  M. Stanković,et al.  Screening inland halophytes from the central Balkan for their antioxidant activity in relation to total phenolic compounds and flavonoids: Are there any prospective medicinal plants? , 2015 .

[31]  G. Jerz,et al.  Solvent system selectivities in countercurrent chromatography using Salicornia gaudichaudiana metabolites as practical example with off-line electrospray mass-spectrometry injection profiling. , 2015, Journal of chromatography. A.

[32]  B. Jha,et al.  Non-targeted metabolomics and scavenging activity of reactive oxygen species reveal the potential of Salicornia brachiata as a functional food , 2015 .

[33]  Silvia Falasca,et al.  Identification of Argentinian saline drylands suitable for growing Salicornia bigelovii for bioenergy , 2014 .

[34]  V. Georgiev,et al.  Recent Advances and Uses of Grape Flavonoids as Nutraceuticals , 2014, Nutrients.

[35]  A. Pandey,et al.  Chemistry and Biological Activities of Flavonoids: An Overview , 2013, TheScientificWorldJournal.

[36]  A. Vianello,et al.  Plant Flavonoids—Biosynthesis, Transport and Involvement in Stress Responses , 2013, International journal of molecular sciences.

[37]  N. Bouzouita,et al.  Phytochemical investigation of Tunisian Salicornia herbacea L., antioxidant, antimicrobial and cytochrome P450 (CYPs) inhibitory activities of its methanol extract , 2013 .

[38]  Giovanni Agati,et al.  Flavonoids as antioxidants in plants: location and functional significance. , 2012, Plant science : an international journal of experimental plant biology.

[39]  Hee-Yeon Park,et al.  Evaluation on anti-adipogenic activity of flavonoid glucopyranosides from Salicornia herbacea , 2012 .

[40]  P. Gates,et al.  Characterisation of Flavonoid Aglycones by Negative Ion Chip-Based Nanospray Tandem Mass Spectrometry , 2012, International journal of analytical chemistry.

[41]  T. Samocha,et al.  Effect of seawater concentration on the productivity and nutritional value of annual Salicornia and perennial Sarcocornia halophytes as leafy vegetable crops , 2011 .

[42]  K. Park,et al.  Dicaffeoylquinic acid derivatives and flavonoid glucosides from glasswort (Salicornia herbacea L.) and their antioxidative activity , 2011 .

[43]  T. Nam,et al.  Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. , 2008, Toxicology in vitro : an international journal published in association with BIBRA.

[44]  G. Dusting,et al.  Natural phenolic compounds as cardiovascular therapeutics: potential role of their antiinflammatory effects. , 2003, Current vascular pharmacology.

[45]  Kelly E Heim,et al.  Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. , 2002, The Journal of nutritional biochemistry.

[46]  J. Quetin-Leclercq,et al.  Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry , 2001, Journal of the American Society for Mass Spectrometry.

[47]  Seema Sharma,et al.  Novel structure-based profiling and annotation workflow—high-throughput analysis of flavonoids using the Thermo Scientific Orbitrap ID-X Tribrid MS , 2018 .

[48]  G. Bedoux,et al.  Bioactive components from seaweeds: Cosmetic applications and future development , 2014 .

[49]  G. Borges,et al.  Nutrient composition and, identification/quantification of major phenolic compounds in Sarcocornia ambigua (Amaranthaceae) using HPLC–ESI-MS/MS , 2014 .

[50]  Young Yoon,et al.  Quantitative Analysis of Flavonoids from Salicomia herbacea L. Extracst by LC-MS , 2008 .