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Rapid Characterization of Triterpene Saponins from Zornia Brasiliensis by HPLC-ESI-MS/MS

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Rapid Characterization of Triterpene Saponins from Zornia Brasiliensis by HPLC-ESI-MS/MS molecules Article Rapid Characterization of Triterpene Saponins from Zornia brasiliensis by HPLC-ESI-MS/MS Yuri Mangueira Nascimento 1 , Lucas Silva Abreu 1 , Ramon Leal Lima 1, Vicente Carlos O. Costa 1, José Iranildo Miranda de Melo 2, Raimundo Braz-Filho 3 , Marcelo Sobral Silva 1 and Josean Fechine Tavares 1,* 1 Graduate Program in Natural and Synthetic Bioactive Products, Health Sciences Center, Universidade Federal da Paraíba, João Pessoa 58051-900, Paraíba, Brazil 2 Graduate Program in Ecology and Conservation, Department of Biology, Center for Biological and Health Sciences, Campina Grande 58429-500, Paraíba, Brazil 3 Center of Sciences and Technologies, Darcy Ribeiro Norte Fluminense State University, Campos dos Goytacazes 28013-600, Rio de Janeiro, Brazil * Correspondence: [email protected]; Tel.: +55-83-3216-7427 Academic Editors: David Popovich and Valeria Patricia Sülsen Received: 2 May 2019; Accepted: 9 July 2019; Published: 10 July 2019 Abstract: Zornia brasiliensis Vogel (Leguminosae) is a species popularly known in Brazil as “urinária”, “urinana”, and “carrapicho”, it is popularly used as a diuretic and in the treatment of venereal diseases. A specific methodology to obtain a saponin-enriched fraction and high-performance liquid chromatography coupled with diode array detection, ion trap mass spectrometry, and TOF-MS (HPLC-DAD-ESI-MS/MS) was applied for the analysis of triterpene saponins. The MS and MS/MS experiments were carried out by ionization in negative mode. Molecular mass and fragmentation data were used to support the structural characterization of the saponins. Based on retention times, high-resolution mass determination and fragmentation, 35 oleanane-triterpene saponins were tentatively identified in Z. brasiliensis. Keywords: triterpene saponins; soyasaponins; Zornia brasiliensis; HPLC-DAD-ESI-MS/MS 1. Introduction The family Leguminosae consists of approximately 770 genera and 19,500 species. It previously included only three subfamilies, but a recent study reorganized the Leguminosae into six subfamilies [1]. These include the subfamily Papilionoideae, which contains the greatest number of genera, including the genus Zornia. The genus Zornia contains approximately 80 species that are distributed throughout the world, mainly in tropical and subtropical regions. In Brazil, the genus is represented by 36 species, 15 of which are endemic [2,3]. Studies have investigated the pharmacological activities of compounds present in species of this genus, including cytotoxic, smooth muscle-relaxing, anticonvulsant, antibacterial, antitumor, anti-inflammatory, and antioxidant activities [4–12]. In turn, phytochemical studies have revealed the presence of isoflavonoids [13,14]. Zornia brasiliensis Vogel, a species popularly known in Brazil as “urinaria”, “urinana”, and “carrapicho”, is adopted in the alternative medicine as a diuretic and in the treatment of venereal diseases [15]. Z. brasiliensis is distributed in the North, Northeast, Center-West and Southeast regions of Brazil. It is associated with the Amazon, Caatinga, Cerrado, and Atlantic Forest phytogeographic domains [16], but is found mainly in the Brazilian Northeast [17] and Venezuela [18]. Two pharmacological studies of this species have reported the antinociceptive activity of 7-methoxyflavone isolated from its aerial parts [19] and the antitumor activity of its essential oil [20]. Molecules 2019, 24, 2519; doi:10.3390/molecules24142519 www.mdpi.com/journal/molecules Molecules 2019, 24, 2519 2 of 14 Molecules 2019, 24, x FOR PEER REVIEW 2 of 15 AA recentrecent phytochemicalphytochemical studystudy ofof thethe aerialaerial partsparts ofof thisthis speciesspecies resultedresulted inin thethe identificationidentification of 1414 compounds,compounds, including flavones,flavones, flavanones,flavanones, isoflavonoids,isoflavonoids, pterocarpans, chalcones, and a novelnovel glycosylated dihydrochalcone—and thisthis chalconechalcone showedshowed cytotoxiccytotoxic activity againstagainst HL-60HL-60 leukemicleukemic cellscells [[21].21]. Hyphenated techniques, such asas high-performancehigh-performance liquid chromatographychromatography (HPLC) coupledcoupled toto mass spectrometryspectrometry (MS)(MS) were were used used for for the the structural structural analysis analysis and and characterization characterization of saponinsof saponins [22 –[22–29]. This29]. This study study represents represents the firstthe first contribution contribution to describe to describe the existencethe existe ofnce triterpene of triterpene saponins saponins from from the genusthe genusZornia Zornia(Leguminosae). (Leguminosae). A total A total of 35 of saponins 35 saponins were were detected detected and and tentatively tentatively identified identified by MS by andMS and MS/ MS.MS/MS. 2. Results 2.1. Characterization of the Compounds by HPLC-ESI-MSHPLC-ESI-MS/MS/MS IdentificationIdentification ofof triterpenetriterpene saponinssaponins byby high-performancehigh-performance liquidliquid chromatography-electrospraychromatography-electrospray ionization-tandemionization-tandem massmass spectrometryspectrometry (HPLC-ESI-MS(HPLC-ESI-MS/MS)/MS) with collision-induced dissociation (CID) under negativenegative ESI-MSESI-MS isis aa well-establishedwell-established andand widelywidely employedemployed techniquetechnique [[24].24]. To obtainobtain thesethese MSMS/MS/MS data,data, aa low-resolutionlow-resolution massmass spectrometerspectrometer was used; and thethe accurateaccurate mass was obtained by a high-resolutionhigh-resolution spectrometer, bothboth usingusing thethe samesame ionizationionization parameters,parameters, and both coupledcoupled to aa high-performance liquidliquid chromatography chromatography system system under under the the same same chromatographic chromatographic conditions. conditions. The The 35 saponins35 saponins that that are are present present in thein the aerial aerial parts parts of Z. of brasiliensisZ. brasiliensisand and tentatively tentatively identified identified are are shown shown on baseon base peak peak chromatogram chromatogram (Figure (Figure1). 1). According to Pollier Pollier et et al., al., after after collision-induced collision-induced dissociation dissociation (CID) (CID) under under negative negative ESI-MS, ESI-MS, the thesaponins saponins undergo undergo glycosidic glycosidic cleavages, cleavages, retaining retaining the the charge charge at at the the reducing reducing end end (e.g., aglyconeaglycone containingcontaining fragment).fragment). In In the the MS MS/MS/MS spectrum, daughter ions provide information on the sugarsugar residuesresidues andand the the aglycone aglycone of theof the fragmented fragmented saponin. sapo Sugarnin. Sugar residues residues are mainly are mainly hexoses hexoses (e.g., glucose (e.g., andglucose galactose), and galactose), 6-deoxyhexoses 6-deoxyhexoses (e.g., rhamnose (e.g., rhamnose and fucose), and pentoses fucose), (e.g., pentoses arabinose (e.g., and arabinose xylose), and uronicxylose), acids and (e.g.,uronic glucuronic acids (e.g., acid glucuronic and galacturonic). acid and galacturonic). Figure 1. BaseBase peak peak chromatogram chromatogram (BPC) (BPC) of ofthe the concentr concentratedated fraction fraction of saponins of saponins obtained obtained by ESI- by ESI-MSMS/MS/ MSin negative in negative mode. mode. The sugarsugar residuesresidues andand thethe aglyconeaglycone couldcould bebe identifiedidentified fromfrom thethe MSMS/MS/MS spectra.spectra. TheThe typicaltypical losseslosses representrepresent waterwater ((−18 Da); andand/or/or rhamnosiderhamnoside residueresidue ((−146 Da); andand/or/or arabinosearabinose ((−150 Da); − − − andand/or/or glucuronicglucuronic acidacid ((−158158 Da).Da). Therefore, thethe daughterdaughter aglyconeaglycone ion,ion, [Aglycone[Aglycone − H]H]−− is based onon − − thisthis typetype oror patternpattern ofof analysis.analysis. Based onon thisthis analysis,analysis, thirty-fivethirty-five saponinssaponins fromfrom ZorniaZornia braziliensisbraziliensis couldcould bebe tentativelytentatively identifiedidentified byby massmass spectrometry.spectrometry. The MSMS/MS/MS data ofof thethe tentativelytentatively identifiedidentified saponinssaponins areare reportedreported inin TableTable1 .1. Molecules 2019, 24, 2519x FOR PEER REVIEW 13 of of 15 14 2.1.1. Aglycones Aglycones of Saponins of Z. Brasiliensis In thethe MS MS/MS/MS fragmentation fragmentation spectra spectra obtained obtained for the for 35 saponins,the 35 saponins, ions m/z 441–531 ions m/z Da, characteristic441–531 Da, characteristicof triterpene aglycones,of triterpene were aglycones, observed. were Through observed. the Through relationships the relationships of the deprotonated of the deprotonated ions of the ionssaponins— of the saponins—m/z 631.3856–999.5135m/z 631.3856–999.5135 Da, and the respectiveDa, and the fragment respective ions fragment at the m /ionsz 441–531 at the Da m/z interval— 441–531 10Da aglyconesinterval—10 were aglycones tentatively were identified tentatively (Figure identified2)[ 24]. (Figure Although 2) [24]. these Although aglycones these have aglycones been detected have beenonly asdetected daughter only ions as withdaughter nominal ionsm with/z values, nominal their m/z molecular values, formulastheir molecular can be predictedformulas can by thebe predictedmolecular by formula the molecular of the exact formula mass of of the the parent exact ion mass and of by the the parent observed ion lossesand by of the the sugarobserved residues losses [24 of]. β theSeven sugar
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