Biotransformations of ent-18-acetoxy-6-ketomanoyl oxides epimers at C-13 with filamentous fungi

Ghoumari, Hanae; Benajiba, Mohamed-Hassan; Garcı́a-Granados, Andrés; Fernández, Antonia; Martı́nez, Antonio; Rivas, Francisco; Arias, J. M.

doi:10.1016/j.phytochem.2006.07.015

Cited by 6 publications

(5 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Filamentous fungi of the genus Fusarium , Beauveria and Botrytis are known for their hydrolytic properties in relation to miscellaneous compounds. Filamentous fungi of the genus Fusarium were often used for biohydroxylation of different substrates such as sesquiterpenoids [ 37 ], diterpenoids [ 37 , 38 , 39 , 40 , 41 ], steroids [ 42 ], sesquiterpene lactones [ 43 , 44 , 45 ], nitriles [ 46 ] and flavonoids [ 47 ]. An interesting example of biohydroxylation is the use of Fusarium oxysporum for the production of α-terpineol (a commonly used fragrance compound) [ 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Grabarczyk

2012

Molecules

View full text Add to dashboard Cite

Bicyclic chloro-, bromo- and iodo-γ-lactones with dimethylcyclohexane rings were used as substrates for bioconversion by several fungal strains (Fusarium, Botrytis and Beauveria). Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into the new compound cis-2-hydroxy-4,6-dimethyl-9-oxabicyclo[4.3.0]- nonan-8-one, mainly the (−)-isomer. When iodo-γ-lactone was used as the substrate, two products were observed: a hydroxy-γ-lactone and an unsaturated lactone. The structures of all substrates and products were established on the basis of their spectral data. The mechanism of dehalogenation of three halolactones was also studied.

show abstract

Section: Introductionmentioning

confidence: 99%

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Grabarczyk

2012

Molecules

View full text Add to dashboard Cite

show abstract

“…In addition, N. crassa originated other metabolites in which the configuration at C-13 influenced the action of the microorganism so that, with the ketoacetate 186, minor hydroxylations were produced by the ent-face, at C-1 (195, 2%) or at C-12 (196, 2%). Meanwhile, an ent-11 -hydroxylation (197, 14%), probably brought about by the reduction of an 11-oxo derivative, also isolated (198, 3%), was achieved with the ketoacetate epimer (187) [52] (Fig. 14).…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

“…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]. 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%).…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

“…Incubations of the same ketoacetates (186 and 187) with F. moniliforme yielded the same functionalizations regardless of the configuration at C-13. The first action of F. moniliforme was the deacetylation of substrates, and afterwards the hydroxylation at C-1 (ent-) (191, 16%; 192, 10%, respectively) or at C-11 (ent-) (193, 6%; 194 9%, respectively) [52] (Fig. 14).…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

See 1 more Smart Citation

Manoyl-Oxide Biotransformations with Filamentous Fungi

Garcı́a-Granados¹,

Martı́nez²,

Parra³

et al. 2007

COC

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…Adicionalmente, algumas reações que não são possíveis de serem realizadas por processos químicos tradicionais são facilmente obtidas com as transformações microbianas (GARCÍA-GRANADOS et al, 2004). Entre as diferentes transformações catalisadas por esses sistemas enzimáticos, a hidroxilação régio e enantioseletiva de carbonos não ativados é particularmente interessante, já que tal transformação é dificilmente obtida a partir dos métodos químicos clássicos (GHOUMARI et al, 2006).…”

Section: íNdice Deunclassified

Estudos sobre o metabolismo microbiano de naftoquinonas e avaliação da citotoxicidade dos metabólitos obtidos

Silva¹

View full text Add to dashboard Cite

Biotransformations of ent-18-acetoxy-6-ketomanoyl oxides epimers at C-13 with filamentous fungi

Cited by 6 publications

References 34 publications

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Manoyl-Oxide Biotransformations with Filamentous Fungi

Estudos sobre o metabolismo microbiano de naftoquinonas e avaliação da citotoxicidade dos metabólitos obtidos

Contact Info

Product

Resources

About