Preformed azulene pigments ofLactarius indigo (Schw.) Fries (Russulaceae, Basidiomycetes)
- 267 Downloads
The structure of a new naturally-occurring azulene, 1-stearoyloxymethylene-4-methyl-7-isopropenylazulene, obtained from an acetone extract of the blue mushroomLactarius indigo, has been determined by chemical and spectral methods.
KeywordsAcetone Indigo Spectral Method Acetone Extract Azulene
Unable to display preview. Download preview PDF.
- 4.For reviews on naturally-occurring azulenes, see A.J. Haagen-Smith, Fortschr. Chem. org. Nat. Stoffe5, 40 (1948); H. Taube, Chem. Rev.50, 127 (1952); E. Heilbronner, Non-Benzenoid Aromatic Compounds. Ed. D. Ginsburg. Interscience Pub., New York 1959; S. Dev, Recent Progress in the Chemistry of Natural and Synthetic Colouring Matters. Ed. T.S. Gore, B.S. Joshi, S.V. Sunthankar and B.D. Tilak. Academic Press, New York 1962.Google Scholar
- 5.We are aware of only 2 azulenes previously known to occur as such in nature: 1,4-dimethyl- and 1-carbomethoxy-4-methylazulene, which are responsible for the blue color of the oil glands of the liverwort,Calypogeia trichomanis; D. Meuche and S. Huneck, Chem. Ber.99, 2669 (1966).CrossRefGoogle Scholar
- 8.H. Willstaedt, Chem. Ber.68, 333 (1935); P.A. Plattner, E. Heilbronner, R.W. Schmid, R. Sandrin and A. Fürst, Chemistry Industry (London),1954, 1202; E. Heilbronner and R.W. Schmid, Helv. chim. Acta,37, 2018 (1954); F. Šorm, V. Benešová, J. Krupička, V. Šneberk, L. Dolejš, V. Herout and J. Sicher, Coll. czech. chem. Commun.20, 227 (1955).CrossRefGoogle Scholar
- 9.H. Willstaedt, Svensk kem. Tidskr.58, 81 (1946); V. Benešová, V. Herout and F. Šorm, Coll. czech. chem. Commun.20, 510 (1955).Google Scholar
- 12.Large, mature specimens ofL. indigo contain hardly any latex and only small amounts of pigment, which we found quite intractable.Google Scholar
- 13.SinceL. indigo is uncommon in our area, and young mushrooms are quite inconspicous, we were unable, despite much effort, to secure another such specimen. The discrepancy between these early observations and those made more recently with specimens from Florida might be caused by strain differences.Google Scholar
- 14.Collected in July, 1977, by H.E. Barnhart at Gainsville, Florida. We wish to thank Col. Barnhart for his help in collecting and shipping the mushrooms.Google Scholar
- 15.Addition of the hexane extract to the column in the absence of acetone led to an instantaneous color change to dark green.Google Scholar
- 16.Nuclear Magnetic Resonance Spectra, spectrum Nr.9657. Sadtler Research Laboratories, Philadelphia 1972.Google Scholar
- 18.Beilstein's Handbuch der Organischen Chemie, Vol.2, 2nd supplement, p. 346. Springer Verlag, Berlin 1942.Google Scholar
- 19.Beilstein's Handbuch der Organischen Chemie, Vol.2, 2nd supplement, p. 351. Springer Verlag, Berlin 1942.Google Scholar