Novel glycoinositolphosphosphingolipids, basidiolipids, from Agaricus

European Journal of Biochemistry

Volumn 259, Issue 1-2, 1999, Pages 331-338

  Jennemann, Richard ^c   Bauer, Bernhard L ^c   Bertalanffy, Helmut ^c   Geyer, Rudolf ^a   Gschwind, Ruth M ^c   Selmer, Thorsten ^b   Wiegandt, Herbert ^b  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

^c Philipps Universität ^*

Author keywords

Agaricus; Basidiolipids; Glyco inositol phospho ceramides; Glycolipids; Sphingolipids

Indexed keywords

BASIDIOLIPID DERIVATIVE; GLYCOINOSITOLPHOSPHOSPHINGOLIPID DERIVATIVE; GLYCOLIPID; SPHINGOLIPID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG ISOLATION; LIPID ANALYSIS; LIPID COMPOSITION; MUSHROOM; NONHUMAN; PHYTOCHEMISTRY; PRIORITY JOURNAL;

ADJUVANTS, IMMUNOLOGIC; AGARICUS; CARBOHYDRATE SEQUENCE; CERAMIDES; FATTY ACIDS; HYDROXY ACIDS; INOSITOL PHOSPHATES; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHOSPHOLIPIDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPHINGOSINE;

AGARICUS; AGARICUS BISPORUS; AGARICUS CAMPESTRIS; BASIDIOMYCOTA;

EID: 0005519404     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1999.00040.x     Document Type: Article

References (28)

1. Sugita, M., Mizunoma, T., Aoki, K., Dulaney, J.T., Inagaki, F., Suzuki, M., Suzuki, A., Ichikawa, S., Kushida, K. & Ohta, S. (1996) Structural characterization of a novel glycoinositolphospholipid from the parasitic nematode, Ascaris suum. Biochim. Biophys. Acta 1302, 185-192.
2. Laine, R.A., Hsieh, T.C.-Y. 78. American Chemical Society, Washington.
3. Lester, R.L. & Dickson, R.C. (1993) Sphinogolipids with inositolphosphate-containing head groups. Adv. Lipid Res. 26, 253-274.
4. Dennis, R.D., Geyer, R., Egge, H., Menges, H., Stirm, S. & Wiegandt, H. (1985) Glycosphingolipids in insects: Chemical structures of ceramide monosaccharide, disaccharide, and trisaccharide from pupae of Calliphora vicina (Insecta: Diptera). Eur. J. Biochem. 146, 51-58.
5. Geyer, R., Geyer, H., Kühnhardt, S., Mink, W. & Stirm, S. (1982) Capillary gas chromatography of methylhexitol acetates obtained upon methylation of N-glycosidically linked glycoprotein oligosaccharides. Anal. Biochem. 121, 263-274.
6. Paz-Parente, J., Cardon, P., Leroy, Y., Montreuil, J., Fournet, B. & Ricart, G. (1985) A convenient method for methylation of glycoprotein glycans in small amounts by using lithium methylsulfinyl carbanion. Carbohydr. Res. 141, 41-47.
7. Geyer, R., Geyer, H., Kühnhardt, S., Mink, W. & Stirm, S. (1983) Methylation analysis of complex carbohydrates in small amounts: capillary gas chromatography-mass fragmentography of methylalditol actetates obtained from N-glycosidically linked glycoprotein oligosaccharides. Anal. Biochem. 133, 197-207.
8. Geyer, R. & Geyer, H. (1994) Saccharide linkage analysis using methylation and other techniques. Methods Enzymol. 230, 86-108.
9. Keeler, J., Clowes, R.T., Davis, A.L. & Laue, E.D. (1994) Pulsed-field gradients: Theory and practice. Methods Enzymol. 239, 145-207.
10. Bodenhausen, G., Vold, R.L. & Vold, R.R. (1980) Multiple quantum spin-echo spectroscopy. J. Magn. Reson. 37, 93-106.
11. Hurd, R.E. (1990) Gradient-enhanced spectroscopy. J. Magn. Reson. 87, 422-428.
12. Keeler, J., Neuhaus, D. & Titman, J. (1988) A convenient technique for the measurement and assignment of long-range carbon-13 proton coupling constants. Chem. Physics Lett. 146, 545-548.
13. Wilker, W., Leibfritz, D., Kessebaum, R. & Bermerl, W. (1993) Gradient selection in inverse heteronuclear correlation spectroscopy. J. Magn. Reson. 31, 287-292.
14. Wagner, R. & Berger, S. (1996) Gradient-selected NOESY-A fourfold reduction of the measurement time for NOESY experiment. J. Magn. Reson. 123, 119-121.
15. Fäcke, T. & Berger, S. (1995) Application of pulsed-field gradients in an improved selective TOCSY experiment. J. Magn. Reson. 113, 257-259.
16. Hanes, C.S. & Isherwood, F.A. (1949) Separation of the phosphoric esters on the filter paper chromatogram. Nature. 164, 1107-1112.
17. Dabrowski, J. (1994) Two-dimensional and related NMR methods. In: Structural Analysis of Oligosaccharides and Polysaccharides (Croasmun, W.R., Carlson, R.M., eds.), pp. 741-783. Verlag Chemie, Weinheim, Germany.
18. Wang, H.X., Ng, T.B., Ooi, V.E., Liu, W.K. & Chang, S.T. (1996) A polysaccharide-peptide complex from cultured mycelia of the mushroom Tricholoma mongolicum with immunoenhancing and antitumor activities. Biochem. Cell Biol. 74, 95-100.
19. Ito, H., Shimura, K., Itoh, H. & Kawade, M. (1997) Antitumor effects of a new polysaccharide-protein complex (ATOM) prepared from Agaricus blazei (Iwade strain 101) 'Himamatsutake' and its mechanism in tumor-bearing mice. Anticancer Res. 17, 277-184.
20. Mizuno, M., Morimoto, M., Minato, K. & Tsuchida, H. (1998) Polysaccharides from Agaricus blazei stimulate lymphocyte T-cell subsets in mice. Biosci. Biotechnol. Biochem. 62, 434-437.
21. Fujimiya, Y., Suzuki, Y., Oshiman, K., Kobori, H., Moriguchi, K., Nakashima, H., Matumoto, Y., Takahara, S., Ebina, T. & Katakura, R. (1998) Selective tumoricidal effect of soluble proteoglucan extracted from the basidiomycete, Agaricus blazei Murill, mediated via natural killer cell activation and apoptosis. Cancer Immunol. Immunother. 46, 147-159.
22. Brennan, P.J. & Roe, J. (1975) The occurrence of a phosphorylated glycosphingolipid in Aspergillus niger. Biochem. J. 147, 179-180.
23. Barr, Laine, R.A. & Lester, R.L. (1984) Carbohydrate structures of three novel phosphoinositol-containing sphingolipids from the yeast Histoplasma capsulatum. Biochemistry. 23, 5589-5596.
24. Smith, S.W. & Lester, R.L. (1974) Inositol phosphorylceramide, a novel substance and the chief member of a major group of yeast sphingolipids containing a single inositol phosphate. J. Biol. Chem. 249, 3395-3405.
25. Conzelmann, A., Puoti, A. & Lester, & Desponds, C. (1992) Two different types of lipid moieties are present in glycophosphoinositol-anchored membrane proteins of Saccharomyces cerevisiae. EMBO J. 11, 457-466.
26. Hanson, B.A. & Lester, R.L. (1980) The extraction of inositol-containing phospholipids and phosphatidylcholine from Saccharomyces cerevisiae and Neurospora crassa. J. Lipid Res. 21, 309-315.
27. Levery, S.B., Toledo, M.S., Suzuki, E., Salyan, M.E.K., Hakomori, S., Straus, A.H. & Takahashi, H.K. (1996) Structural characterization of a new galactofuranose-containing glycolipid antigen of paracoccidioides brasiliensis. Biochem. Biophys. Res. Commun. 222, 639-645.
28. Wiegandt, H. (1994) Principles of glycosphingolipid-oligosaccharide constitution. Progr. Brain Res. 101, 63-73.