Skip to main content

Advertisement

SpringerLink
Log in

Cell wall polysaccharides isolated from the fungus Neotestudina rosatii, one of the etiologic agents of mycetoma in man

  • Published:
Glycoconjugate Journal Aims and scope Submit manuscript

Abstract

The alkali-extractable water-soluble polysaccharides F1SS isolated from the cell wall of two isolates of the pathogen Neotestudina rosatii and one of Pseudophaeotrichum sudanense, which is now considered as a synonym of the former, have been studied by methylation analysis, GC–MS and NMR spectroscopy. The three polysaccharides differ mainly in their content in galactofuranose, and have the following idealized repeating unit:

with m ≈ 19, and p ≈ 6 in all cases, but being n ≈ 1 for N. rosatii CBS 271.75, n ≈ 0.5 for N. rosatii CBS 331.78, and n ≈ 0.15 for P. sudanense.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig 1
Fig 2
Fig 3
Fig 4
Fig 5

Similar content being viewed by others

Abbreviations

CBS:

Centraalbureau voor Schimmelcultures

DEPT:

Distortionless enhancement by polarization transfer

DOSY:

Diffusion ordered NMR spectroscopy

DQF-COSY:

Double quantum filtered correlated spectroscopy

F1SS:

Alkali extractable and water soluble polysaccharide

GC:

gas chromatography

GC–MS:

Gas chromatography–mass spectrometry

HMBC:

Heteronuclear multiple bond correlation

HMQC:

Heteronuclear multiple quantum coherence

NOESY:

Nuclear Overhauser enhancement spectroscopy

SEC:

Size exclusion chromatography

TFA:

Trifluoroacetic acid

TMSi:

Trimethylsilyl

TOCSY:

Totally correlated spectroscopy

References

  1. Fahal, A.H.: Mycetoma: a thorn in the flesh. Trans. R. Soc. Trop. Med. Hyg. 98, 3–11 (2004). doi:10.1016/S0035-9203(03)00009-9

    Article  CAS  PubMed  Google Scholar 

  2. de Hoog, G.S., Adelmann, D., Ahmed, A.O.A., van Belkum, A.: Phylogeny and typification of Madurella mycetomatis, with a comparison of other agents of eumycetoma. Mycoses 47, 121–130 (2004). doi:10.1111/j.1439-0507.2004.00964.x

    Article  PubMed  Google Scholar 

  3. Torres-Rodríguez, J.M., del Palacio-Hernanz, A., Guarro-Artigas, J., Negroni-Briz, R., Pereiro-Miguens, M.: Micología Médica. Masson, S.A., Barcelona (1993)

    Google Scholar 

  4. Bernardo, D., Cabo, A.P., Novaes-Ledieu, M., Mendoza, C.G.: Verticillium disease or “dry bubble” of cultivated mushrooms: the Agaricus bisporus lectin recognizes and binds the Verticillium fungicola cell wall glucogalactomannan. Can. J. Microbiol. 50, 729–735 (2004). doi:10.1139/w04-047

    Article  CAS  PubMed  Google Scholar 

  5. Cutler, J.E.: N-glycosylation of yeast, with emphasis on Candida albicans. Med. Mycol. 39, 75–86 (2001)

    CAS  PubMed  Google Scholar 

  6. Lima, O.C., Figueiredo, C.C., Previato, J.O., Mendonca-Previato, L., Morandi, V., Lopes Bezerra, L.M.: Involvement of fungal cell wall components in adhesion of Sporothrix schenckii to human fibronectin. Infect. Immun. 69, 6874–6880 (2001). doi:10.1128/IAI.69.11.6874-6880.2001

    Article  CAS  PubMed  Google Scholar 

  7. Serrano-Gómez, D., Leal, J.A., Corbí, A.: DC-SIGN mediates the binding of Aspergillus fumigatus and keratinophylic fungi by human dendritic cells. Immunobiology 210, 175–183 (2005). doi:10.1016/j.imbio.2005.05.011

    Article  PubMed  Google Scholar 

  8. Gander, J.E.: Fungal cell wall glycoproteins and peptido-polysaccharides. Annu. Rev. Microbiol. 28, 103–119 (1974). doi:10.1146/annurev.mi.28.100174.000535

    Article  CAS  PubMed  Google Scholar 

  9. Jikibara, T., Takegawa, K., Iwahara, S.: Studies on the uronic acid-containing glycoproteins of Fusarium sp. M7-1: I. Isolation and some properties of the glycoproteins. J. Biochem. (Tokyo) 111, 225–229 (1992)

    CAS  Google Scholar 

  10. Nakajima, T., Yoshida, M., Hiura, N., Matsuda, K.: Structure of the cell wall proteogalactomannan from Neurospora crassa. II. Structural analysis of the polysaccharide part. J. Biochem. 96, 1013–1020 (1984)

    CAS  PubMed  Google Scholar 

  11. Ahrazem, O., Gómez-Miranda, B., Prieto, A., Barasoaín, I., Bernabé, M., Leal, J.A.: An acidic water-soluble cell wall polysaccharide: a chemotaxonomic marker for Fusarium and Gibberella. Mycol. Res. 104, 603–610 (2000). doi:10.1017/S0953756299001550

    Article  CAS  Google Scholar 

  12. Domenech, J., Barasoaín, I., Prieto, A., Gómez-Miranda, B., Bernabé, M., Leal, J.A.: An antigenic water-soluble glucogalactomannan extracted from cell walls of Paecilomyces fumosoroseus and Paecilomyces farinosus. Microbiology 142, 3497–3503 (1996)

    Article  CAS  PubMed  Google Scholar 

  13. Hearn, V.M., Wilson, E.V., Latgé, J.P., Mackenzie, D.W.: Immunochemical studies of Aspergillus fumigatus mycelial antigens by polyacrylamide gel electrophoresis and western blotting techniques. J. Gen. Microbiol. 136, 1525–1535 (1990)

    CAS  PubMed  Google Scholar 

  14. Shibata, N., Kobayashi, H., Okawa, Y., Suzuki, S.: Existence of novel beta-1,2 linkage-containing side chain in the mannan of Candida lusitaniae, antigenically related to Candida albicans serotype A. Eur. J. Biochem. 270, 2565–2575 (2003). doi:10.1046/j.1432-1033.2003.03622.x

    Article  CAS  PubMed  Google Scholar 

  15. Suzuki, S.: Immunochemical study on mannans of genus Candida. I. Structural investigation of antigenic factors 1, 4, 5, 6, 8, 9, 11, 13, 13b and 34. Curr. Top. Med. Microbiol. 8, 57–70 (1997)

    CAS  Google Scholar 

  16. Bernabé, M., Ahrazem, O., Prieto, A., Leal, J.A.: Evolution of polysaccharides F1SS and proposal of their utilisation as antigens for rapid detection of fungal contaminants. EJEAFChe 1 (1). http://ejeafche.uvigo.es, (2002)

  17. Almeida, I.C., Neville, D.C., Mehlert, A., Treumann, A., Ferguson, M.A., Previato, J.O., Travassos, L.R.: Structure of the N-linked oligosaccharide of the main diagnostic antigen of the pathogenic fungus Paracoccidioides brasiliensis. Glycobiology 6, 507–515 (1996). doi:10.1093/glycob/6.5.507

    Article  CAS  PubMed  Google Scholar 

  18. Latgé, J.P., Debeaupuis, J.P., Moutaouakil, M., Diaquin, M., Sarfati, J., Prévost, M.C., Wieruszeski, J.M., Leroy, Y., Fournet, B.: Galactomannan and the circulating antigens of Aspergillus fumigatus. In: Latgé, J.P., Boucias, D. (eds.) Fungal Cell Wall and Immune Response, vol. H 53, pp. 143–155. Springer, Berlin (1991)

    Google Scholar 

  19. Albersheim, P., Darvill, A.G., Davis, K.R., Lau, J.M., McNeil, M., Sharp, J.K., York, W.S.: Why study the structures of biological molecules? The importance of studying the structures of complex carbohydrates. In: Dugger, W.M., Bartnicki-García, S. (eds.) Structure, Function, and Biosynthesis of Plant Cell Walls, pp. 19–51. American Society of Plant Physiologists, Rockville, Maryland (1984)

    Google Scholar 

  20. Hawksworth, D.L.: Ascospore sculpturing and generic concepts in the Testudinaceae (syn. Zopfiaceae). Can. J. Bot. 57, 91–99 (1979). doi:10.1139/b79-017

    Article  Google Scholar 

  21. Gómez-Miranda, B., Moya, A., Leal, J.A.: Differences in the cell wall composition in the type species of Eupenicillium and Talaromyces. Exp. Mycol. 12, 258–263 (1988). doi:10.1016/0147-5975(88)90040-0

    Article  Google Scholar 

  22. Prieto, A., Rupérez, P., Hernández-Barranco, A., Leal, J.A.: Partial characterisation of galactofuranose-containing heteropolysaccharides from the cell walls of Talaromyces helicus. Carbohydr. Res. 177, 265–272 (1988). doi:10.1016/0008-6215(88)85063-8

    Article  CAS  Google Scholar 

  23. Ahrazem, O., Gómez-Miranda, B., Prieto, A., Bernabé, M., Leal, J.A.: Heterogeneity of the genus Myrothecium as revealed by cell wall polysaccharides. Arch. Microbiol. 173, 296–302 (2000). doi:10.1007/s002030000149

    Article  CAS  PubMed  Google Scholar 

  24. Dubois, M., Giller, K.A., Rebers, P.A., Smith, F.A.: Colorimetric method for determination of sugars and related substances. Anal. Chem. 28, 350–356 (1956). doi:10.1021/ac60111a017

    Article  CAS  Google Scholar 

  25. Laine, R.A., Esselman, W.J., Sweeley, C.C.: Gas–liquid chromatography of carbohydrates. Methods Enzymol. 28, 159–167 (1972). doi:10.1016/0076-6879(72)28012-0

    Article  Google Scholar 

  26. Gerwig, G.J., Kamerling, J.P., Vliegenthart, J.F.G.: Determination of the absolute configuration of mono-saccharides in complex carbohydrates by capillary G.L.C.. Carbohydr. Res. 77, 10–17 (1979). doi:10.1016/S0008-6215(00)83788-X

    Article  CAS  PubMed  Google Scholar 

  27. Ciucanu, I., Kerek, F.: A simple and rapid method for the permethylation of carbohydrates. Carbohydr. Res. 131, 209–217 (1984). doi:10.1016/0008-6215(84)85242-8

    Article  CAS  Google Scholar 

  28. Bock, K., Pedersen, C.: Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides. Adv. Carbohydr. Chem. Biochem. 41, 27–66 (1983). doi:10.1016/S0065-2318(08)60055-4

    Article  CAS  Google Scholar 

  29. Prieto, A., Leal, J.A., Poveda, A., Jiménez-Barbero, J., Gómez-Miranda, B., Domenech, J., Ahrazem, O., Bernabé, M.: Structure of complex cell wall polysaccharides isolated from Trichoderma and Hypocrea species. Carbohydr. Res. 304, 281–291 (1997). doi:10.1016/S0008-6215(97)00239-5

    Article  CAS  PubMed  Google Scholar 

  30. Bock, K., Pedersen, C.: A study of 13C–H coupling constants in hexopyranoses. J. Chem. Soc. Perk. Trans. II, 293–297 (1974). doi:10.1039/p29740000293

    Google Scholar 

  31. Stilbs, P.: Molecular self-diffusion coefficients in Fourier transform nuclear magnetic resonance spectrometric analysis of complex mixtures. Anal. Chem. 53, 2135–2137 (1981). doi:10.1021/ac00236a044

    Article  CAS  Google Scholar 

  32. Díaz, M.D., Berger, S.: Studies of the complexation of sugars by diffusion-ordered NMR spectroscopy. Carbohydr. Res. 319, 1–5 (2000). doi:10.1016/S0008-6215(00)00239-1

    Article  Google Scholar 

  33. Pelta, M.D., Morris, G.A., Stchedroff, M.J., Hammond, S.J.: A one-shot sequence for high-resolution diffusion-ordered spectroscopy. Magn. Reson. Chem. 40, S147–S152 (2002). doi:10.1002/mrc.1107

    Article  CAS  Google Scholar 

  34. Bock, K., Pedersen, C., Pedersen, H.: Carbon-13 nuclear magnetic resonance data for oligosaccharides. Adv. Carbohydr. Chem. Biochem. 42, 193–225 (1984). doi:10.1016/S0065-2318(08)60125-0

    Article  CAS  Google Scholar 

  35. Parra, E., Jiménez-Barbero, J., Bernabé, M., Leal, J.A., Prieto, A., Gómez-Miranda, B.: Structural studies of fungal cell-wall polysaccharides from two strains of Talaromyces flavus. Carbohydr. Res. 251, 315–325 (1994). doi:10.1016/0008-6215(94)84294-9

    Article  CAS  PubMed  Google Scholar 

  36. Cyr, N., Perlin, A.S.: The conformations of furanosides. A 13C nuclear magnetic resonance study. Can. J. Chem. 57, 2504–2511 (1979). doi:10.1139/v79-399

    Article  CAS  Google Scholar 

  37. Gómez-Miranda, B., Prieto, A., Leal, J.A., Ahrazem, O., Jiménez-Barbero, J., Bernabé, M.: Differences among the cell wall galactomannans from Aspergilus wentii and Chaetosartorya chrysella and that of Aspergillus fumigatus. Glycoconj. J. 20, 239–246 (2004). doi:10.1023/B:GLYC.0000025818.83019.e4

    Article  PubMed  Google Scholar 

  38. Pereyra, T., Prieto, A., Bernabé, M., Leal, J.A.: Studies of new polysaccharides from Lasallia pustulata (L.) Hoffm. Lichenologist 35, 177–185 (2003). doi:10.1016/S0024-2829(03)00015-X

    Article  Google Scholar 

  39. Prieto, A., Leal, J., Giménez-Abián, M.I., Canales, A., Jiménez-Barbero, J., Bernabé, M.: Isolation and structural determination of a unique polysaccharide containing mannofuranose from the cell wall of the fungus Acrospermum compressum. Glycoconj. J. 24, 421–428 (2007). doi:10.1007/s10719-007-9032-5

    Article  CAS  PubMed  Google Scholar 

  40. Deshpande, N., Wilkins, M.R., Packer, N., Nevalainen, H.: Protein glycosylation pathways in filamentous fungi. Glycobiology 18, 626–637 (2008). doi:10.1093/glycob/cwn044

    Article  CAS  PubMed  Google Scholar 

  41. San Blas, G.: The cell wall of fungal human pathogens: Its possible role in host-parasite relationships. Mycopathologia 79, 159–184 (1982). doi:10.1007/BF01837196

    Article  CAS  PubMed  Google Scholar 

  42. Netea, M.G., Gow, N.A.R., Munro, C.A., Bates, S., Collins, C., Ferwerda, G., Hobson, R.P., Bertram, G., Hughes, H.B., Jansen, T., Jacobs, L., Buurman, E.T., Gijzen, K., Williams, D.L., Torensma, R., McKinnon, A., MacCallum, D.M., Odds, F.C., Van der Meer, J.W.M., Brown, A.J.P., Kullberg, B.J.: Immune sensing of Candida albicans requires cooperative recognition of mannans and glucans by lectin and Toll-like receptors. J. Clin. Invest. 116, 1642–1650 (2006). doi:10.1172/JCI27114

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

The authors thank Mrs. Mónica Fontenla for her technical support. This work was supported by Grant CTQ-2006-10874-C02-01 from Ministerio de Educación y Ciencia of Spain.

Author information

Authors and Affiliations

  1. Centro de Investigaciones Biológicas, CSIC, c/ Ramiro de Maeztu, 9, Ciudad Universitaria, 28040, Madrid, Spain

    Juan Antonio Leal, M. Inmaculada Giménez-Abián, Ángeles Canales, Jesús Jiménez-Barbero & Alicia Prieto

  2. Departamento de Química Orgánica Biológica, Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006, Madrid, Spain

    Manuel Bernabé

Authors
  1. Juan Antonio Leal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Inmaculada Giménez-Abián
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ángeles Canales
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jesús Jiménez-Barbero
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Manuel Bernabé
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Alicia Prieto
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alicia Prieto.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Leal, J.A., Giménez-Abián, M.I., Canales, Á. et al. Cell wall polysaccharides isolated from the fungus Neotestudina rosatii, one of the etiologic agents of mycetoma in man. Glycoconj J 26, 1047–1054 (2009). https://doi.org/10.1007/s10719-008-9224-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10719-008-9224-7

Keywords

Search

Navigation