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Cosins A and B (regioisomers arisingFrontiers in Plant Science www.frontiersin.orgNovember Volume ArticleSisTerraza et al.Coumarins in FeDeficient Arabidopsis PlantsTABLE MSMS data for some of the compounds secreted and accumulated by Arabidopsis thaliana roots in response to Fe deficiency mz ratios in the fragment ions and their relative intensity.Compound # Annotation Parent ion mz ..Ion form ESIMSn mz (Relative intensity, in )Coniferylaldehyde hexoside ,dihydroxymethoxycoumarin hexoside (fraxetin hexoside) hydroxy,dimethoxycoumarin hexoside (isofraxidin hexoside)[MH] [MH]MS , , , , , , MS MS , , , , , , MS MS , , , , , , , , , , , , , , , , , , , , , , , , , , MS MS , , , , , , , , , , , , , MS MS , , MS , , , , MS , , , , , , .[MH]Sinapyl aldehyde hexoside.[MH] Ferulic acid Coniferyl aldehyde Sinapyl aldehyde…[MH] [MH] [MH]Numbers in italics (Compound #) refer for the labels used for each and every compound in Table .All information have been taken from the HPLCESIMSMS(ion trap) analysis.The main ion from the MS and MS spectra can also be indicated in the fusion of fraxetin plus the monolignol Eledoisin Technical Information hydroxyconiferyl alcohol, Cheng and Chen, , Figure C), possess a formula identical to that of compound (C H O).The structural differences among these coumarinolignans corresponding towards the monolignol moiety (Figure B) are identical to those found among the elemental formulae of (i) a methoxy group differentiates coniferyl from sinapyl alcohols as well as the elemental formula of from that of ; (ii) a hydroxyl group differentiates hydroxyconiferyl from coniferyl alcohols and the elemental formula of from that of ; and (iii) a methyl group differentiates hydroxyconiferyl and sinapyl alcohols and also the formula of from these of .To confirm the identification of as cleomiscosins, we isolated coumarinolignans from C.viscosa seeds.The seed isolate was analyzed by each HPLCUVVISESIMS(TOF) and HPLCESIMS(ion trap) making use of Elution plan and constructive ESI ionization.The HPLCESIMS(TOF) chromatogram for mz . corresponding to the cleomiscosins C and D [MH] ions, showed only two peaks, at .and .min, matching with all the RTs of and (Figure C; Table).Similarly, the HPLCESIMS(TOF) chromatogram for mz . corresponding to the cleomiscosins A and B [MH] ions, showed only two peaks, at .and .min, matching together with the RTs of (Figure C; Table).Peaks were assigned to cleomiscosin isomers in line with the elution order reported in the literature (Chattopadhyay et al Kaur et al).These annotations were confirmed by the full match among the MS spectra from the cleomiscosins D, C, B, and also a, and those of compounds , , and , respectively (Figure C).Compound eluted at shorter occasions than the cleomiscosins (.vs..min), as anticipated in the structural variations between hydroxycleomiscosin A and B and cleomiscosins (see above).Moreover, compound shares elemental formula as well as the presence of a fraxetin moietywith hydroxycleomiscosins A and B, and its MS spectrum showed a loss of Da in the [MH] ion (Figure B; Supplementary Table S), which was previously reported for hydroxycleomiscosin A (Cheng and Chen,) but will not occur in cleomiscosins.Therefore, was putatively annotated as hydroxycleomiscosin A andor B (Table ).Coumarin and Coumarinolignan Concentrations in Root ExtractsQuantification of phenolic compounds was carried out working with the PubMed ID: [MH] and [MhexosideH] signals inside the HPLCESIMS(TOF).Coumarin.

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