Chemotaxonomic fingerprinting of chilean lichens through maldi and electrospray ionization mass spectrometry

Brazilian Archives of Biology and Technology

Volumn 58, Issue 2, 2015, Pages 244-253

  Santos, Leonardo Silva ^a   Soriano, Maria del Pilar Camarantin ^a   Mirabal Gallardo, Yaneris ^a   Carrasco Sanchez, Veronica ^a   Nachtigall, Fabiane Manke ^a   Pereira, Iris ^a   Pereira, Eugenia ^b  

^a UNIVERSIDAD DE TALCA   (Chile)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

Chemotaxonomic; Chilean lichens; Fingerprint; MALDI TOF MS; UPLC ESI( ) MS

Indexed keywords

RAMALINA; RAMALINA FARINACEA; STEREOCAULON RAMULOSUM; TELOSCHISTES CHRYSOPHTHALMUS; USNEA;

EID: 84929322726     PISSN: 15168913     EISSN: 16784324     Source Type: Journal    
DOI: 10.1590/S1516-8913201400185     Document Type: Article

References (65)

1. Aouidi F, Dupuy N, Artaud J, Roussos S, Msallem M, Gaime IP et al. Rapid quantitative determination of oleuropein in olive leaves (Olea europaea) using mid-infrared spectroscopy combined with chemometric analyses. Ind Crops Prod. 2012; 37: 292-297.
2. Alcantara GB, Honda NK, Ferreira MMC, Ferreira AG. Chemometric analysis applied in 1H HR-MAS NMR and FT-IR data for chemotaxonomic distinction of intact lichen samples. Anal Chim Acta. 2007; 595: 3-8.
3. Asahina Y, Shibata S. Chemistry of Lichen substances. 1a Ed. Tokio: Edition Tokyo, 1954, 245p.
4. Barnes J. Pharmacognosy in the 21st centur. Pharm J. 2000; 264: 701-703.
5. Behera BC, Verma N, Sonone A, Makhija U. Evaluation of Antioxidant Potential of the Cultures Mycobiont of a Lichen Usnea ghattensis. Phytother Res. 2005; 19: 58-64.
6. Belton PS, Colquhoun IJ, Kemsley EK, Delgadillo I, Roma P, Dennis MJ et al. Application of Chemometrics to the H-1 NMR spectra of apple juices: discrimination between apple varieties. Food Chem. 1998; 61: 207-213.
7. Boustie J, Grube M. Lichens - a promising source of bioactive secondary metabolites, Plant Genet Resour. 2005; 3: 273-278.
8. Brandt H, Ehmann T. Toward Prediction: Using Chemometrics for the Optimization of Sample Preparation in MALDI-TOF MS of Synthetic Polymers. Anal Chem. 2010; 82: 8169-8175.
9. Carbonero ER, Sassaki GL, Stuelp PM, Gorin PA, Woranovicz-Barreira SM, Iacomini M. Comparative studies of the polysaccharides isolated from lichenized fungi of the genus Cladonia: significance as chemotypes. FEMS Microbiol Lett. 2001; 194: 65-69.
10. Carrasco H, Espinoza L, Quilhot W. Depsides and triterpenes in Pseudocyphellaria coriifolia (lichens) and biological activity against Trypanosoma cruzi. Nat Prod Res. 2013; 27: 1607-1610.
11. Catharino RR, Marques LA, Santos LS, Baptista AS, Glória EM, Calori-Domingues MA et al. Aflatoxin Screening by MALDI-TOF Mass Spectrometry. Anal Chem. 2005; 77: 8155-8157.
12. Clerc P. Species concepts in the genus Usnea (lichenized Ascomycetes). Lichenologist. 1998; 30: 312-340.
13. Crespo A, Kauff F, Divakar PK, Del Prado R, Pérez-Ortega S, Amo G et al. Phylogenetic generic classification of parmelioid lichens (Parmeliaceae, Ascomycota) based on molecular, morphological and chemical evidence. Taxon. 2010; 59: 1735-1753.
14. Cuellar MF, Rubio CL, Quiñonez NS, Montenegro IV, Salas CS, Da Silva HA et al. Carbohydrate, glycopeptide and protein components of the lichen Sticta sp. and effect of storage. Phytochemistry. 1993; 33: 547-552.
15. Defernez M, Kemsley EK, WILSON RH. Use of Infrared Spectroscopy and Chemometrics for the Authentication of Fruit Purees. J Agric Food Chem. 1995; 42: 109-113.
16. Eifler-Lima VL, Perry A, Sinbandhit S, Boustie J, Tomasi S, Schenkel E. NMR spectral data of salazinic acid isolated from some species of Parmotrema. Magn Reson Chem. 2000; 38: 472-474.
17. Ellis DI, Dunn WB, Griffin JL, Allwood JW, Goodacre R. Metabolic fingerprinting as a diagnostic tool. Pharmacogenomics. 2007; 8: 1243-1266.
18. Fahselt D. Alternative method for analyzing protein characterized. Bryologist. 1980; 83: 340-342.
19. Frisvad JC, Andersen B, Thrane U. The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi. Mycol Res. 2008; 112: 231-240.
20. Fournet A, Ferreira ME, Rojas De Arias A, Torres De Ortiz S, Inchausti A, Yalaff G, et al. Activity of Compounds Isolated From Chilean Lichens Against Experimental Cutaneous Leishmaniasis. Comp Biochem Physiol, Part C: Pharmacol Toxicol Endocrinol. 1997; 116: 51-54.
21. Ghorbani A, Langenberger G, Sauerborn J. A Comparison of the wild food plant use knowledge of ethnic minorities in Naban River Watershed National Nature Reserve, Yunnan, SW China. J Ethnobiol Ethnomed. 2012; 8: 1-9.
22. Gielwanowska I, Olech M. New Ultrastructural and Physiological Features of the Thallus in Antarctic Lichens. Acta Biol Cracov. Ser Bot. 2012; 54: 40-52.
23. Gorin PAJ, Iacomini M. Structural diversity of D-galacto-D-mannan components isolated from lichens having ascomycetous mycosymbionts. Carbohydr Res. 1985; 142: 253-267.
24. Gustafsson JOR, Oehler MK, Ruszkiewicz A, Mccoll SR, Hoffmann P. MALDI Imaging Mass Spectrometry (MALDI-IMS)-Application of Spatial Proteomics for Ovarian Cancer Classification and Diagnosis. Int J Mol Sci. 2011; 12: 773-794.
25. Hidalgo ME, Fernández E, Quilhot W, Lissi E. Antioxidant activity of depsides and depsidones. Phytochemistry. 1994; 37: 1585-1587.
26. Honda NK, Vilegas W. A química dos liquens. Quim Nova. 21: 110-125.
27. Honegger R, Bartnicki-Garcia S. Cell wall structure and composition of cultured mycobionts from the lichens Cladonia macrophylla, Cladonia caespiticia, and Physcia stellaris (Lecanorales, Ascomycetes). Mycol Res. 1998; 95: 905-914.
28. Howells SL, Maxwell RJ, Peet AC, Griffiths JR. An Investigation of Tumor 1H Nuclear Magnetic Resonance Spectra by the Application of Chemometric Techniques. Magn Reson Med. 1992; 28: 214-236.
29. Huneck S, Yoshimura I. Identification of Lichen Substances, Springer-Verlag Berlin and Heidelberg GmbH&Co. K, Germany. 1996.
30. Huneck S. The Significance of Lichens and Their Metabolites. Naturwissenschaften. 1999; 86: 559-570.
31. Krishnamurthy T. Rapid identification of bacteria by direct matrix assisted laser desorption/ionization mass spectrometric analysis of whole cells, Rapid Commun Mass Spectrom. 1996; 10:1992-1996.
32. Lai YH, NI YN, Serge K. Authentication of Cassia seed on the basis of two-wavelength HPLC fingerprinting with the use of chemometrics. Chin Chem Lett. 2010; 21: 213-216.
33. Leavitt SD, Johnson L, St. Clair LL. Species Delimitation and Evolution in Morphologically and Chemically Diverse Communities of the Lichen-Forming Genus Xanthoparmelia (Parmeliaceae, Ascomycota) in Western North America. Am J Bot. 2011; 98: 175-188.
34. Legaz ME, Vicente C. Endogenous Inactivators of Arginase, L-Arginine Decarboxylase, and Agmatine Amidinohydrolase in Evernia prunastri Thallus. Plant Physiol. 1983; 71: 300-302.
35. Lin CK. The Lichen Genus Lobaria at Shenmi Lake, Northeastern Taiwan. Collection Res. 2013; 26: 37-42.
36. Lücking R, Rivas-Plata E, Chaves JL, Umaña L, Sipman HJ. How many tropical lichens are there really?, 2009, p.399-417. In A. Thell, M.R.D. Seaward and T. Feuerer (eds.), Diversity of Lichenology, Anniversary volume, Bibl. Lichenol., Berlin-Stuttgart, Alemania.
37. Lücking R. Taxonomy: a discipline on the brink of extinction. Are DNA bar barcode scanners the future of biodiversity research? Arch Sci. 2009; 61: 75-88.
38. Lumbsch H T, Ahti T, Altermann S, Amo Da Paz G, Aptroot A, Bárcenas AP et al. One hundred new species of lichenized fungi: a signature of undiscovered global diversity. Phytotaxa. 2011; 18: 1-127.
39. Manojlovic NT, Vasiljevic PJ, Maskovic PZ. Chemical composition and antioxidant activity of lichen Toninia candida. Braz J Pharmacog. 2012; 22: 291-298.
40. Molnar K, Farkas E. Current results on biological activities of lichen secondary metabolites: a review, Z Naturforsch C. 2010; 65: 157-173.
41. Müller K. Activity of Compounds Isolated From Chilean Lichens Against Experimental Cutaneous Leishmaniasis. Pharmaceutically relevant metabolites from lichens. Appl Microbiol Biotechnol. 2001; 56: 9-16.
42. Nanni P, Parisi D, Roda G, Casale M, Belluzzi A, Roda E, Mayer L, Roda A. Serum protein profiling in patients with inflammatory bowel diseases using selective solid-phase bulk extraction, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and chemometric data analysis. Rapid Commun Mass Spectrom. 2007; 21: 4142-4148.
43. Ohmenhaeuser M, Monakhova YB, Kuballa T, Lachenmeier DW. Qualitative and Quantitative Control of Honeys Using NMR Spectroscopy and Chemometrics. Anal Chem. 2013: 1-9.
44. Oksanen I. Ecological and biotechnological aspects of lichens. Applied Microbiol Biotechnol. 2006; 73: 723-734.
45. Olafsdottir ES, Ingólfsdottir K. Polysaccharides from lichens: structural characteristics and biological activity. Planta Medica. 2001; 67: 199-208.
46. Omarsdottir S, Freysdottir J, Olafsdottir ES. Immunomodulating polysaccharides from lichen Thamnolia vermicularis var. subuliformis. Phytomedicine. 2007; 14: 179-184.
47. Peña-Méndez EM, Gajdošová D, Novotná K, PROŠEK P, HAVEL J. Mass spectrometry of humic substances of different origin including those from Antarctica: A comparative study. Talanta. 2010; 67: 880-890.
48. Pereira I, Amaro JM, Astudillo L, Padilla C, Lobos O, Santos LS. Assessment of antibacterial and antifungic activity in four species of Maule region in Chile. Proceedings of the 7th European Workshop of Biotechnologists of microalgae and other phototrophic organisms, Nuthetal, Germany. 2007.
49. Pomerantsev AL, Rodionova OY. Chemometric view on "comprehensive chemometrics." Chemom Intell Lab Syst. 2010; 103: 19-24.
50. Quilhot W, Leighton G, Flores E, Fernandez E, Peña W, Guzman G. Factores Exógenos y Endógenos determinantes de la Acumulación de Acido Usnico en Líquenes. Acta Farm Bonaerense. 1987; 6: 15-22.
51. Radebe N, Rode K, Pizzi A, Pasch H. Microstructure elucidation of polyflavonoid tannis by MALDI-TOF-CID. J Appl Polym Sci. 2013; 127: 1937-1950.
52. Russo A, Piovano M, Lombardo L, Garbarino J, Cardile V. Lichen metabolites prevent UV light and nitric oxide-mediated plasmid DNA damage and induce apoptosis in human melanoma cells. Life Sci. 2008; 83: 468-474.
53. Rustichelli C, Visioli G, Kostecka D, Vurro E, Sanità Di Toppi L, Marmiroli N. Proteomic analysis in the lichen Physcia adscendens exposed to cadmium stress. Environ Pollut. 2008; 156: 1121-1127.
54. Santos LS, Haddad R, Höehr NF, Pilli RA, Eberlin MN. Fast Screening of Low Molecular Weight Compounds by Thin-Layer Chromatography and "On-Spot" MALDI-TOF Mass Spectrometry. Anal Chem. 2004; 76: 2144-2147.
55. Sassaki GL, Gorin PA, Reis RA, Serrato RV, Elífio SL, Iacomini M. Carbohydrate, glycolipid, and lipid components from the photobiont (Scytonema sp.) of the lichen Dictyonema glabratum. Carbohydr Res. 2005; 340: 1808-18017.
56. Schmeda-Hirschmann G, Tapia A, Lima B, Pertino M, Sortino S, Zacchino S. A New Antifungal and Antiprotozoal Depside from the Andean Lichen Protousnea poeppigii. Phytother Res. 2008; 22: 349-355.
57. Scotti L, FERREIRA EI, Da Silva MS, Scotti MT. Chemometric Studies on Natural Products as Potential Inhibitors of the NADH Oxidase from Trypanosoma cruzi Using the VolSurf Approach. Molecules. 2010; 15: 7363-7377.
58. Shukla V, Joshi GP, RAWAT MSM. Lichens as a potential natural source of bioactive compounds: a review. Phytochem Rev. 2010; 9: 303-314.
59. Stocker-Wörgötter E. Metabolic diversity of lichen-forming ascomycetous fungi: culturing, polyketide and shikimate metabolite production, and PKS gene. Nat Prod Rep. 2008; 25:188-200.
60. Tell A, Crespo A, Divakar KPK, Kärnefelt I, Leavitt SD, Lumbsch HT, Seaward MRD. A review of the lichen family Parmeliaceae - history, phylogeny and current taxonomy. Nord J Bot. 2012; 30: 641-664.
61. Trygg J, Holmes E, Lundstedt T. Chemometrics in Metabonomics. J Proteome Res. 2007; 6: 469-479.
62. Vaidyanathan S, Kell DB, Goodacre R. Rapid, high-throughput microbial characterization by metabolite and protein profiling of whole cells using soft-ionization mass spectrometry. Abstr Papers Am Chem Soc. 2002; 224: U199, 011-Biot.
63. Vitikainen O. William Nylander (1822-1899) and lichen chemotaxonomy. Bryologist. 2001; 104: 263-267.
64. Vogels JTWE, Terwel L, Tas AC, Van Den Berg F, Dukel F, Van der Greef F. Detection of Adulteration in Orange Juices by a New Screening Method Using Proton NMR Spectroscopy in Combination with Pattern Recognition Techniques. J Agric Food Chem. 1996; 44: 175-180.
65. Weinmann W, Baumeister K, Kaufmann I, Przybylski M. Separation and characterization of humic acids from Antarctica by capillary electrophoresis and matrix-assisted laser desorption ionization time-of-flight mass spectrometry: Inclusion complexes of humic acids with cyclodextrins. J Chromatogr A. 2003; 1014: 117-127.