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Velleral

Velleral (2,2,8-trimethyl-3,3a,8,8a-tetrahydro-1H-azulene-5,6-dicarbaldehyde) is a sesquiterpene dialdehyde found in certain mushrooms, like Lactarius torminosus and Lactarius vellereus, after which it was named. The compound is thought to be part of a chemical defense system that protects the mushrooms against predation. First isolated in 1969, and characterized structurally in 1973, velleral has antimicrobial activity. Several syntheses have been devised.

References

References

  1. (1991). "Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms". Planta Medica.
  2. (1984). "Labile toxic compounds of the Lactarii: the role of the laticiferous hyphae as a storage depot for precursors of pungent dialdehydes". Mycologia.
  3. (1976). "Fungal extractives .10. Alternative synthesis of velleral skeleton". Journal of Organic Chemistry.
  4. (1975). "Fungal extractives .9. Synthesis of velleral skeleton and a total synthesis of pyrovellerolactone". Journal of Organic Chemistry.
  5. (1978). "Fungal extractives .12. Construction of vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone – revised structures". Journal of the American Chemical Society.
  6. (1969). "Velleral und iso-Velleral, scharf schmeckende Stoffe aus ''Lactarius vellereus'' FRIES". Archiv der Pharmazie.
  7. (1973). "Fungal extractives .4. Structure of a novel sesquiterpene dialdehyde from ''Lactarius'' by spectroscopic methods". Tetrahedron.
  8. (1985). "The sesquiterpenes of ''Lactarius vellereus'' and their role in a proposed chemical defense system". Journal of Natural Products.
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sesquiterpenes azulenes aldehydes
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