Manoyl-Oxide Biotransformations with Filamentous Fungi

Abstract

Microbial transformations of manoyl oxides by filamentous fungi have been used to introduce hydroxyl groups, regio-and stereoselectively, into substrates at positions difficult to achieve by chemical means. The principal objective of most papers published in this field has been to produce new, highly oxygenated, bioactive manoyl-oxide compounds that present a large diversity of biological properties. The manoyl oxides most frequently studied at present are forskolin and its derivatives, the pharmacological activity of which is related to their ability to activate AC (adenylate cyclase), thus generating an increase in intracellular cAMP (cyclic adenosine monophosphate). The microbial hydroxylation of forskolin and 1,9-dideoxyforskolin has been extensively studied, using the fungi Scopuloriopsis sp., Syncephalastrum sp., Neurospora crassa, Mortierella isabellina and several Aspergillus sp.. Other biotransformation studies of natural manoyl oxides and hemi-synthetic enantio derivatives, carried out via the biomimetic cyclization of ent-8 -hydroxylabda-13(16),14-dienes, have used filamentous fungi Curvularia lunata, Cunninghamella elegans, Fusarium moniliforme, Gibberella fujikuroi, Gliocladium roseum, Mucor plumbeus, Rhizopus nigricans and Neurospora crassa. In some cases, the new hydroxylations were introduced at the same positions as in natural forskolin, yielding some noteworthy products that show biological activities.

Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

“…The transformation of 1 with B. bassiana afforded exclusively product 4 in acceptable yield (51.3%), in comparison with other biotransformations. 24 These results gave additional evidences of the importance of the species, strains and media employed in the structural diversity of the products and the yields of the biotransformations.…”

Microbial Transformation of Triterpenoids

“…Several reviews on microbial transformation of terpenoids have been published in recent years [22][23][24]. Biotransformation has also been used to expand the chemical diversity of terpenoids, the largest group of natural products.…”

Terpenoid biotransformations by Mucor species

“…M. plumbeus was also used in diterpenoid biotransformation studies by several other researchers (Hanson et al 2003;García-Granados et al 2007). Thus, in order to obtain homochiral intermediates for the hemisynthesis of biologically relevant molecules, Aranda et al carried out a study of the biotransformation of labdane-derived terpenoids.…”