Biotransformation of 5α-hydroxycaryophylla-4(12),8(13)-diene withCunninghamella elegansandRhizopus stolonifer

Abstract

Biotransformation of 5 α -hydroxycaryophylla-4(12),8(13)-diene ( 1 ) was studied with Cunninghamella elegans and Rhizopus stolonifer . Incubation of 1 with C. elegans gave regioselective oxidative addition (hydration) and isomerization at the C-4(12) exocyclic double bond and hydroxylation at C-3 and C-15, and thus provided two polar metabolites, (3 Z ),8(14)-caryophylladiene-5 α ,(11 R )-15-diol ( 2 ) and 3 β ,4 β ,5 α -trihydroxycaryophylla-8(13)-ene ( 3 ). Incubation of 1 with R. stolonifer gave a transannular cyclization reaction and afforded 2 β -methoxyclovan-9-one ( 4 ), clovan-2 β -ol-9-one ( 5 ) and 8-methoxycaryolane-5 α ,13 β -diol ( 6 ). Compounds 3 and 6 are new compounds described here for the fi rst time; their structures were deduced with the help of different spectroscopic techniques.

Natural sesquiterpenoids

“…218 Biotransformations of 5a-hydroxycaryophyll-4(12),8(13)-diene with the fungi Cunninghamella elegans and Rhizopus stolonifer have been reported. 219 The rst total synthesis of rumphellaone A has been accomplished. 220 It has been shown that b-caryophyllene and caryophyllene oxide act as phytogrowth and photosynthesis inhibitors.…”

Biotransformation of perfumery terpenoids, (−)-ambrox® by a fungal culture Macrophomina phaseolina and a plant cell suspension culture of Peganum harmala

“…In continuation of our biotransformational studies on bioactive compounds [14-20], structural transformation of (−)-ambrox ( 1 ) with Macrophomina phaseolina and Peganum harmala was studied which afforded nine oxidative metabolites 2 10 . Compounds 2 , 3 , 5 , 6 10 were previously reported as metabolites of compound 1 [18,19,21].…”