Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms

Publikation: Beiträge in ZeitschriftenZeitschriftenaufsätzeForschung

Authors

  • Veronika Hellwig
  • Johannes Dasenbrock
  • Claudia Gräf
  • Lydia Kahner
  • Susanne Schumann
  • Wolfgang Steglich

Boletus calopus and closely related mushrooms of the Boletus section Calopodes are characterized by their bitter taste, which is caused mainly by O-acetylcyclocalopin A (6a), a member of a series of unique δ-lactone derivatives. Besides the simple lactone calopin (1b) and its O-acetyl derivative la, the more complex cyclocalopins 6-12 have been isolated and their structures elucidated. Cyclocalopin D (10a) is an unprecedented α-glucoside in which the sugar residue is bound to an enolic hydroxy group., The chemical conversion of 6b into la established the same stereochemistry for the calopin and cyclocalopin types of metabolites.

OriginalspracheEnglisch
ZeitschriftEuropean Journal of Organic Chemistry
Jahrgang2002
Ausgabenummer17
Seiten (von - bis)2895-2904
Anzahl der Seiten10
ISSN1434-193X
DOIs
PublikationsstatusErschienen - 09.2002
Extern publiziertJa