Isolation, characterisation and quantification of the main oligomeric macrocyclic ellagitannins in Epilobium angustifolium by ultra-high performance chromatography with diode array detection and electrospray tandem mass spectrometry

Journal of Chromatography A

Volumn 1419, Issue , 2015, Pages 26-36

  Baert, Nicolas ^a   Karonen, Maarit ^a   Salminen, Juha Pekka ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Multiple Reaction Monitoring; Oligomeric ellagitannin; Plant phenolic fingerprint; Willowherb

Indexed keywords

CHROMATOGRAPHY; FLAVONOIDS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAMMALS; MASS SPECTROMETRY; OLIGOMERS; TANNINS;

DIODE ARRAY DETECTION; ELECTROSPRAY TANDEM MASS SPECTROMETRY; ELLAGITANNIN; MULTIPLE REACTION MONITORING; MULTIPLE-REACTION MONITORING MODES; PLANT PHENOLIC FINGERPRINT; ULTRA HIGH PERFORMANCE; WILLOWHERB;

PLANT EXTRACTS;

PLANT EXTRACT; TANNIN;

CHEMISTRY; EPILOBIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROCEDURES; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EPILOBIUM; HYDROLYZABLE TANNINS; PLANT EXTRACTS; TANDEM MASS SPECTROMETRY;

EID: 84948659089     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2015.09.050     Document Type: Article

References (50)

1. M.H. Tavendale, L.P. Meagher, D. Pacheco, N. Walker, G.T. Attwood, S. Sivakumaran, Methane production from in vitro rumen incubations with Lotuspedunculatus and Medicago sativa, and effects of extractable condensed tannin fractions on methanogenesis, Anim. Feed Sci. Technol. 123-124 (2005)403-419.
2. A.K. Patra, J. Saxena, A new perspective on the use of plant secondary metabolites to inhibit methanogenesis in the rumen, Phytochemistry 71 (2010)1198-1222.
3. D.N. Kamra, N. Agarwal, L.C. Chaudhary, Inhibition of ruminal methanogenesis by tropical plants containing secondary compounds, Int. Congr. Ser. 1293(2006) 156-163.
4. A. Novobilský, E. Stringano, C. Hayot Carbonero, L.M.J. Smith, H.L. Enemark, I.MuellerHarvey, et al., In vitro effects of extracts and purified tannins of sainfoin(Onobrychis viciifolia) against two cattle nematodes, Vet. Parasitol. 196 (2013)532-537.
5. H. Hoste, F. Jackson, S. Athanasiadou, S.M. Thamsborg, S.O. Hoskin, The effectsof tanninrich plants on parasitic nematodes in ruminants, Trends Parasitol. 22(2006) 253-261.
6. J.-P. Salminen, T. Roslin, M. Karonen, J. Sinkkonen, K. Pihlaja, P. Pulkkinen, Seasonal variation in the content of hydrolyzable tannins, flavonoid glycosides,and proanthocyanidins in oak leaves, J. Chem. Ecol. 30 (2004) 1693-1711.
7. J.-P. Salminen, V. Ossipov, E. Haukioja, K. Pihlaja, Seasonal variation in the content of hydrolysable tannins in leaves of Betula pubescens, Phytochemistry 57(2001) 15-22.
8. C.T. Yarnes, W.J. Boecklen, J.-P. Salminen, No simple sum: seasonal variation intannin phenotypes and leafminers in hybrid oaks, Chemoecology 18 (2007)39-51.
9. J.-P. Salminen, V. Ossipov, K. Pihlaja, Distribution of hydrolysable tannins in thefoliage of Finnish birch species, Z. Naturforsch. C 57 (2002) 248-256.
10. A. Tuominen, E. Toivonen, P. Mutikainen, J.-P. Salminen, Defensive strategiesin Geranium sylvaticum. Part 1: Organspecific distribution of water-solubletannins, flavonoids and phenolic acids, Phytochemistry 95 (2013) 394-407.
11. H. Kawamoto, F. Nakatsubo, Solubility of protein complexed with galloylglucoses, Phytochemistry 30 (1997) 485-488.
12. H.-C. Zhou, Y.-M. Lin, S.-D. Wei, N.F. Tam, Structural diversity and antioxidantactivity of condensed tannins fractionated from mangosteen pericarp, FoodChem. 129 (2011) 1710-1720.
13. M. Labieniec, T. Gabryelak, G. Falcioni, Antioxidant and prooxidant effects oftannins in digestive cells of the freshwater mussel Unio tumidus, Mutat. Res.Toxicol. Environ. Mutagen. 539 (2003) 19-28.
14. E. Bouki, V.K. Dimitriadis, M. Kaloyianni, S. Dailianis, Antioxidant and prooxidant challenge of tannic acid in mussel hemocytes exposed to cadmium,Mar. Environ. Res. 85 (2013) 13-20.
15. S.M. Hadi, S.H. Bhat, A.S. Azmi, S. Hanif, U. Shamim, M.F. Ullah, Oxidative breakage of cellular DNA by plant polyphenols: a putative mechanism for anticancerproperties, Semin. Cancer Biol. 17 (2007) 370-376.
16. P. Arapitsas Hydrolyzable tannin analysis in food, Food Chem. 135 (2012)1708-1717.
17. P. Schofield, D.M. Mbugua, A.N. Pell, Analysis of condensed tannins: a review,Anim. Feed Sci. Technol. 91 (2001) 21-40.
18. J.L. Aleixandre-Tudo, H. Nieuwoudt, J.L. Aleixandre, W.J. Du Toit, Robustultraviolet-visible (UV-vis) partial least-squares (PLS) models for tannin quantification in red wine, J. Agric. Food Chem. 63 (2015) 1088-1098.
19. K. Komatsu, Y. Nagayama, K. Tanaka, Y. Ling, P. Basnet, M.R. Meselhy, Development of a high performance liquid chromatographic method for systematicquantitative analysis of chemical constituents in rhubarb, Chem. Pharm. Bull.(Tokyo) 54 (2006) 941-947.
20. S. Granica, A. Bazylko, A.K. Kiss, Determination of macrocyclic ellagitanninoenothein B in plant materials by HPLC-DAD-MS: method development andvalidation, Phytochem. Anal. 23 (2012) 582-587.
21. D. Guillarme, J. Schappler, S. Rudaz, J.-L. Veuthey, Coupling ultra-high-pressureliquid chromatography with mass spectrometry, Trends Anal. Chem. 29 (2010)15-27.
22. M. Rodriguez-Aller, R. Gurny, J.-L. Veuthey, D. Guillarme, Coupling ultra high-pressure liquid chromatography with mass spectrometry: constraints andpossible applications, J. Chromatogr. A 1292 (2012) 2-18.
23. C. Lo, J.C.Y. Le Blanc, C.K.Y. Yu, K.H. Sze, D.C.M. Ng, I.K. Chu, Detection, characterization, and quantification of resveratrol glycosides in transgenic arabidopsisover-expressing a sorghum stilbene synthase gene by liquid chromatography/tandem mass spectrometry, Rapid Commun. Mass Spectrom. 21 (2007)4101-4108.
24. S. Forcat, M.H. Bennett, J.W. Mansfield, M.R. Grant, A rapid and robust methodfor simultaneously measuring changes in the phytohormones ABA, JA and SAin plants following biotic and abiotic stress, Plant Methods 4 (2008) 16.
25. E. Ruszová, J. Cheel, S. Pávek, M. Moravcová, M. Hermannová, I. Matějková,et al., Epilobium angustifolium extract demonstrates multiple effects on dermalfibroblasts in vitro and skin photo-protection in vivo, Gen. Physiol. Biophys. 32(2013) 347-359.
26. A.K. Kiss, J. Kowalski, M.F. Melzig, Effect of Epilobium angustifolium L. extractsand polyphenols on cell proliferation and neutral endopeptidase activity inselected cell lines, Pharmazie 61 (2006) 66-69.
27. I. Kosalec, N. Kopjar, D. Kremer, Antimicrobial activity of willowherb (Epilobiumangustifolium L.) leaves and flowers, Curr. Drug Targets 14 (2013) 986-991.
28. S. Granica, J.P. Piwowarski, M.E. Czerwińska, A.K. Kiss, Phytochemistry, pharmacology and traditional uses of different Epilobium species (Onagraceae): areview, J. Ethnopharmacol. 156 (2014) 316-346.
29. A.K. Kiss, A. Bazylko, A. Filipek, S. Granica, E. Jaszewska, U. Kiarszys, et al., Oenothein B's contribution to the anti-inflammatory and antioxidant activityof Epilobium sp, Phytomedicine 18 (2011) 557-560.
30. A.G. Ramstead, I.A. Schepetkin, M.T. Quinn, M.A. Jutila, Oenothein B, a cyclicdimeric ellagitannin isolated from Epilobium angustifolium, enhances IFNγ production by lymphocytes, PLoS ONE 7 (2012).
31. T. Yoshida, T. Hatano, H. Ito, Chemistry and function of vegetable polyphenolswith high molecular weights, Biofactors 13 (2000) 121-125.
32. H. Li, T. Tanaka, Y.-J. Zhang, C.-R. Yang, I. Kouno, Rubusuaviins A-F,monomeric and oligomeric ellagitannins from Chinese sweet tea and theiralphaamylase inhibitory activity, Chem. Pharm. Bull. (Tokyo) 55 (2007)1325-1331.
33. Y.J. Tsai, T. Aoki, H. Maruta, H. Abe, H. Sakagami, T. Hatano, et al., Mouse mammary tumor virus gene expression is suppressed by oligomeric ellagitannins,novel inhibitors of poly(ADP-ribose) glycohydrolase, J. Biol. Chem. 267 (1992)14436-14442.
34. H. Ito, P. Li, M. Koreishi, A. Nagatomo, N. Nishida, T. Yoshida, Ellagitanninoligomers and a neolignan from pomegranate arils and their inhibitory effectson the formation of advanced glycation end products, Food Chem. 152 (2014)323-330.
35. Elias Lönnrotin Flora Fennica III, in: K. Linnilä, S. Savikko, T. Lempiäinen (Eds.),Elias Lönnrotin Flora Fenn III, Oy Amanita Ltd, Hämeenlinna, 2002, p. 148.
36. L.M. Katiki, J.F.S. Ferreira, J.M. Gonzalez, A.M. Zajac, D.S. Lindsay, A.C.S. Chagas,et al., Anthelmintic effect of plant extracts containing condensed and hydrolyzable tannins on Caenorhabditis elegans, and their antioxidant capacity, Vet.Parasitol. 192 (2013) 218-227.
37. R. Bhatta, Y. Uyeno, K. Tajima, A. Takenaka, Y. Yabumoto, I. Nonaka, et al., Difference in the nature of tannins on in vitro ruminal methane and volatile fattyacid production and on methanogenic archaea and protozoal populations, J.Dairy Sci. 92 (2009) 5512-5522.
38. W.F. Pellikaan, E. Stringano, J. Leenaars, D.J.G.M. Bongers, S. van SchuppenvanLaar, J. Plant, et al., Evaluating effects of tannins on extent and rate of in vitro gasand CH4 production using an automated pressure evaluation system (APES),Anim. Feed Sci. Technol. 166-167 (2011) 377-390.
39. D.R. Mani, S.E. Abbatiello, S.A. Carr, Statistical characterization of multiple-reaction monitoring mass spectrometry (MRM-MS) assays for quantitativeproteomics, BMC Bioinformatics 13 (Suppl. 1) (2012) S9.
40. M. Caban, N. Migowska, P. Stepnowski, M. Kwiatkowski, J. Kumirska, Matrixeffects and recovery calculations in analyses of pharmaceuticals based on thedetermination of β-blockers and β-agonists in environmental samples, J. Chro-matogr. A 1258 (2012) 117-127.
41. B. Ducrey, A. Marston, S. Göhring, R.W. Hartmann, K. Hostettmann, Inhibition of 5 alpha-reductase and aromatase by the ellagitannins oenothein A andoenothein B from Epilobium species, Planta Med. 63 (1997) 111-114.
42. T. Yoshida, T. Hatano, T. Okuda, Two-dimensional NMR spectra of hydrolysabletannins which form equilibrium mixtures, Magn. Reson. Chem. 30 (1992)46-55.
43. T. Yoshida, T. Chou, M. Matsuda, T. Yasuhara, K. Yazaki, T. Hatano, et al., Woodfordin D and oenothein A, trimeric hydrolyzable tannins of macroring structure with antitumor activity, Chem. Pharm. Bull. (Tokyo) 39 (1991)1157-1162.
44. M. Karonen, J. Parker, A.A. Agrawal, J.-P. Salminen, First evidence ofhexameric and heptameric ellagitannins in plants detected by liquid chromatography/electrospray ionisation mass spectrometry, Rapid Commun. MassSpectrom. 24 (2010) 3151-3156.
45. J.-P. Salminen, M. Karonen, J. Sinkkonen, Chemical ecology of tannins: recentdevelopments in tannin chemistry reveal new structures and structure-activitypatterns, Chem. Eur. J. 17 (2011) 2806-2816.
46. T. Hooi Poay, L. Sui Kiong, C. Cheng Hock, Characterisation of galloylatedcyanogenic glucosides and hydrolysable tannins from leaves of Phyllagathisrotundifolia by LC-ESI-MS/MS, Phytochem. Anal. 22 (2011) 516-525.
47. A.N. Shikov, O.N. Pozharitskaya, S.A. Ivanova, V.G. Makarov, V.P. Tikhonov,B. Galambosi, Improved and validated HPTLC method for quantification ofoenothein B and its use for analysis of Epilobium angustifolium L, J. PlanarChromatogr. 23 (2010) 70-74.
48. R. King, R. Bonfiglio, C. Fernandez-Metzler, C. Miller-Stein, T. Olah, Mechanisticinvestigation of ionization suppression in electrospray ionization, J. Am. Soc.Mass Spectrom. 11 (2000) 942-950.
49. P. Kebarle, L. Tang, From ions in solution to ions in the gas phase-the mechanism of electrospray mass spectrometry, Anal. Chem. 65 (1993) 972A-986A.
50. A. Kruve, I. Leito, K. Herodes, Combating matrix effects in LC/ESI/MS: the extrapolative dilution approach, Anal. Chim. Acta 651 (2009) 75-80.