A new phenolic metabolite, involutone, isolated from the mushroom Paxillus involutus

Canadian Journal of Chemistry

Volumn 81, Issue 1, 2003, Pages 118-124

  Antkowiak, Róza ^a   Antkowiak, Wieslaw Z ^a   Banczyk, Izabela ^a   Mikolajczyk, Lucyna ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Brown Roll rim; Enzymic glucosylation and esterification; Glucosides and linoleates; Metabolite isolation; NMR of mushroom pigments; Paxillus involutus; Quaternary hydroxycyclopentanedione; Structure study

Indexed keywords

DERIVATIVES; PHENOLS; SPECTRUM ANALYZERS;

PHENOLIC METABOLITE;

METABOLITES;

5 (3,4 DIHYDROXYPHENYL) 2 (4 HYDROXYPHENYL) 2 HYDROXY 4 CYCLOPENTEN 1,3 DIONE; ALCOHOL; BUTANOL; CROTONIC ACID DERIVATIVE; ERGOSTEROL; GLUCOPYRANOSIDE; INVOLUTIN; INVOLUTONE; LINOLEIC ACID; MANNITOL; METHANOL; PHENOL; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; ENZYME GLYCOSYLATION; ESTERIFICATION; EXTRACTION; ISOLATION PROCEDURE; METABOLITE; MUSHROOM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PAXILLUS INVOLUTUS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037269522     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-194     Document Type: Article

References (46)

1. S. Grzymala. Rocz. Panstw. Zakl. Hig. 9, 277 (1958).
2. W.Z. Antkowiak. The chemistry and toxicology of mushroom alkaloids. In Chemistry and toxicology of diverse classes of alkaloids. Edited by M.S. Blum. Alaken, Inc., Fort Collins. 1996. Chap. 4.
3. W. Lasota and W. Fortak. Acta Pol. Pharm. 23, 81 (1966).
4. W. Lasota, G. Rybarkiewicz, and H. Mlodecki. Acta Pol. Pharm. 24, 75 (1967).
5. M.H. Malone, V.E. Tyler, Jr. and L.R. Brady. Lloydia, 30, 250 (1967).
6. F. Bschor, J. Kohlmeyer, and H.J. Mallach. Z. Pilzkd. 29, 1
7. F. Bschor and H.J. Mallach. Arch. Toxikol. 20, 82 (1963).
8. J. Schmidt, W. Hartmann, A. Würstlin, and H. Deicher. Dtsch. Med. Wochenschr. 96, 1188 (1971).
9. H. Deicher and W. Stangel. Verh. Dtsch. Ges. Inn. Med. 83, 1606 (1977).
10. M. Winkelmann, F. Borchard, W. Stangel, and B. Grabensee. Dtsch. Med. Wochenschr. 107, 1190 (1982).
11. M. Winkelmann, W. Stangel, I. Schedel, and B. Grabensee. Klin. Wochenschr. 64, 935 (1986).
12. W. Lasota. Farm. Pol. 4, 317 (1970).
13. W. Lasota. Zeszyty Naukowe Bromatologii i Chemii Toksykologicznej, 3, 9 (1970).
14. R.L. Edwards, G.C. Elsworthy, and N. Kale. J. Chem. Soc. (C), 405 (1967).
15. R.L. Edwards and M.Gill. J. Chem. Soc. Perkin Trans. 1, 1529 (1973).
16. W. Steglich, A. Thilmann, H. Besl, and A. Bresinsky. Z. Naturforsch. C: J. Biosci. 32C, 46 (1977).
17. M. Gill and W. Steglich. Pigments of fungi (Macromycetes). In Prog. Chem. Org. Nat. Prod. Vol. 51. Edited by W. Herz, H. Grisebach, G.W. Kirby and Ch. Tamm. Springer-Verlag, Wien, New York. 1987. pp. 64 and 67.
18. R. Feling, K. Polborn, W. Steglich, J. Mühlbacher, and G. Bringmann. Tetrahedron, 57, 7857 (2001); corrigendum Tetrahedron, 57, 10 231 (2001).
19. R. Feling, K. Polborn, W. Steglich, J. Mühlbacher, and G. Bringmann. Tetrahedron, 57, 7857 (2001); corrigendum Tetrahedron, 57, 10 231 (2001).
20. (a) J. Zarb and D.R.Walters. Lett. Appl. Microbiol. 18, 5 (1994);
21. (b) S. Fornale, T. Sarjala, and N. Bagni. New Phytol. 143, 581 (1999).
22. M. Stadler and O. Sterner. Phytochemistry, 49, 1013 (1998).
23. (a) N. Mitsuo, H. Takeichi, and T. Satoh. Chem. Pharm. Bull. 32, 1183 (1984);
24. (b) S.L. Flitsch and G.M. Watt. Enzymes in carbohydrate chemistry: formation of glycosidic linkages. In Biotechnology. 2nd ed. Vol. 8b. Edited by H.-J. Rehm and G. Reed. Wiley-VCH, Weinheim, New York. 2000. pp. 243-274.
25. C.-A. Chen and C.J. Sih. J. Org. Chem. 63, 9620 (1998).
26. T. Matsumoto, W. Trueb, R. Gwinner, and C.H. Eugster. Helv. Chim. Acta, 52, 716 (1969).
27. H. Besl, A. Bresinsky, W. Steglich, and K. Zipfel. Chem. Ber. 106, 3223 (1973).
28. M.-H. Chang, G.-J. Wang, Y.-H. Kuo, and C.-K. Lee. J. Chin. Chem. Soc. 47, 1131 (2000).
29. R. Radeglia, H. Poleschner, and M. Heydenrich. Magn. Reson. Chem. 29, 1028 (1991).
30. L.C.D. Stasi, J.C. Gomes, and W. Vilegas. Chem. Pharm. Bull. 47, 890 (1999).
31. S. Murata. Bull. Chem. Soc. Jpn. 57, 3597 (1984).
32. L. Crombie and A.D. Heavers. J. Chem. Soc. Perkin Trans. 1, 1929 (1992).
33. G. Knothe and T.C. Nelsen. J. Chem. Soc. Perkin Trans. 2, 2019 (1998).
34. J.A. Elix and K.L. Gaul. Aust. J. Chem. 39, 613 (1986).
35. (a) The Aldrich library of FT-IR spectra. 2nd ed. 3, 4222 B (1997);
36. (b) The Aldrich library of FT-IR spectra. 1, 270A (1997).
37. 1H FT NMR spectra. 1st ed. 3, 570 B (1993)
38. 1H FT NMR spectra. 1st ed. 1, 289C (1993).
39. W. Zhou and W.D. Nes. Tetrahedron Lett. 41, 2791 (2000).
40. B.W. Sigurskjold, I. Haunstrup, and K. Bock. Acta Chem. Scand. 46, 451 (1992).
41. P.A. Finan, R.I. Reed, W. Snedden, and J.M. Wilson. J. Chem. Soc. 5945 (1963).
42. M. Budesinsky, M. Cerny, I. Cerny, S. Samek, and T. Trnka. Collect. Czech. Chem. Commun. 60, 311 (1995).
43. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, and M. Rossi. Synth. Commun. 30, 1319 (2000).
44. H. Prawat, C. Mahidol, S. Ruchirawat, U. Prawat, P. Tuntiwachwuttikul, U. Tooptakong, W.C. Taylor, C. Pakawatchai, B.W. Skelton, and A.H. White. Phytochemistry, 40, 1167 (1995).
45. A.B. Pomilio, M.D. Gonzalez, and C.C. Eceizabarrena. Phytochemistry, 41, 1393 (1996).
46. M.K. Higgins, R.S. Bly, and S.L. Morgan. Anal. Chem. 66, 2656 (1994).