Preformed azulene pigments ofLactarius indigo (Schw.) Fries (Russulaceae, Basidiomycetes)
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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.
- 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.
- 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).
- Rubber can constitute up to 1.7% of the dry matter of the latex: W.D. Stewart, W.L. Wachtel, J.J. Shipman and J.A. Yanko, Science122, 1271 (1955).
- H. Willstaedt, Chem. Ber.69, 997 (1936); F. Šorm, V. Benešová and V. Herout, Coll. czech. chem. Commun.19, 357 (1954).
- 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).
- H. Willstaedt, Svensk kem. Tidskr.58, 81 (1946); V. Benešová, V. Herout and F. Šorm, Coll. czech. chem. Commun.20, 510 (1955).
- K. Vokáč, Z. Samek, V. Herout and F. Šorm, Coll. czech. chem. Commun.35, 1296 (1970).
- D.J. Bertelli and J.H. Crabtree, Tetrahedron24, 2079 (1968).
- Large, mature specimens ofL. indigo contain hardly any latex and only small amounts of pigment, which we found quite intractable.
- 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.
- 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.
- Addition of the hexane extract to the column in the absence of acetone led to an instantaneous color change to dark green.
- Nuclear Magnetic Resonance Spectra, spectrum Nr.9657. Sadtler Research Laboratories, Philadelphia 1972.
- D. Meuche, B.B. Molloy, D.H. Reid and E. Heilbronner, Helv. chim. Acta46, 2483 (1963).
- Beilstein's Handbuch der Organischen Chemie, Vol.2, 2nd supplement, p. 346. Springer Verlag, Berlin 1942.
- Beilstein's Handbuch der Organischen Chemie, Vol.2, 2nd supplement, p. 351. Springer Verlag, Berlin 1942.
- K. Hafner and C. Bernhard, Justus Liebigs Annln Chem.625, 108 (1959).
- Preformed azulene pigments ofLactarius indigo (Schw.) Fries (Russulaceae, Basidiomycetes)
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