Biotransformation of ent-6α-acetoxy- and ent-6-ketomanoyl oxides with rhizopus nigricans and curvularia lunata cultures

Garcı́a-Granados, Andrés; Gutiérrez, Juan J.; Martı́nez, Antonio; Rivas, Francisco; Arias, JoséM.

doi:10.1016/s0031-9422(96)00845-x

Cited by 5 publications

(4 citation statements)

References 10 publications

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“…Biotransformation of ketoacetate 186 with R. nigricans gave a 14,15-epoxyderivative (188, 3%), and a derivative of 188 with an ent-3 -hydroxyl group (189, 21%). However, in the biotransformation of the ketoacetate epimer at C-13 (187) only ent-11 -hydroxylation (190, 56%) was achieved [48]. Incubations of the same ketoacetates (186 and 187) with F. moniliforme yielded the same functionalizations regardless of the configuration at C-13.…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

“…These spiran tetrahydrofuran derivatives hydroxylated at C-14 (153 and 155) may result from the epoxidation of the double bond by the microorganism and a subsequent intramolecular cyclization with the participation of the hydroxyl group at C-16 (Scheme 3). Biotransformation of 147, without a hydroxyl group at C-16, by R. nigricans gave only a 14,15-epoxyderivative (156, 6%), while its epimer at C-13 (148) was biohydroxylated at C-11 by the ent-face (157, 29%) [48] (Fig. 12).…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

“…Biotransformation of ketodiol 179 (ent-16,18-dihydroxy-6-oxo-13-epi-manoyl oxide) by R. nigricans gave hydroxylations at C-20 (180, 14%) or, by the ent-face, at C-3 (181, 13%), and at C-11 (182, 4%) [48], whereas its 13-epimer, (183) gave rise only to ent-3 -(184, 12%) or ent-11 -hydroxylations (185, 47%). The incubation of the same ke- [48]. Two 13-epimeric 18-acetoxy-6-oxo ent-manoyl oxides have been produced (186 and 187), using CCL, which improves the yield of these substrates [52].…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

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Manoyl-Oxide Biotransformations with Filamentous Fungi

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et al. 2007

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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.

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Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%