73510-14-2Relevant academic research and scientific papers
REARRANGED CARYOPHYLLENES BY BIOTRANSFORMATION WITH CHAETOMIUM COCHLIODES
Abraham, Wolf-Rainer,Ernst, Ludger,Arfmann, Hans-Adolf
, p. 757 - 763 (2007/10/02)
Biotransformation of caryophyllene by Chaetomium cochliodes DSM 1909 (=ATCC 10195) leads to 4,5-epoxy-caryophyllene-7,12-diol as the main product.The hydroxylation of the geminal methyl groups is not very stereospecific, but as with Diploida gossypina the main product possesses the 11R-configuration.Side-reactions are ring contraction or formation of clovanes, probably via epoxide rearrangements.The use of mono- or diepoxy-caryophyllene as the substrate does not increase the yields significantly.Instead, diepoxy-caryophyllene gave a punctatin derivative.The same molecular framework, but with a different configuration, was observed among the fermentation products from Diplodia gossypina, which supports the assumption that a caryophyllane is the precursor of this class of antibiotics.
BIOTRANSFORMATION OF CARYOPHYLLENE BY DIPLODIA GOSSYPINA
Abraham, Wolf-Rainer,Ernst, Ludger,Stumpf, Burghard
, p. 115 - 120 (2007/10/02)
Fermentation of caryophyllene with Diplodia gossypina affords a number of products which are all derived from the 4,5-epoxide.Twelve of these are described here for the first time.The main products are 12-hydroxy-4,5-epoxy-caryophyllene and the corresponding acid.On side reactions additional hydroxylations occured or the exo-methylene group was also epoxidized and further degraded.Two rearranged compounds were found, one resulting from an epoxide rearrangement leading to an eight-membered ring, the other one being a cyclization product possessing the rare skeleton of the punctatin antibiotics.
