Induction of steroidal hydroxylase activity by plant defence compounds in the filamentous fungus Cochliobolus lunatus

Vitas, Marko; Smith, Kelvin E.; Plavec, Janez; Kesselmeier, J.; Pajič, Tadej; Ferlan, Aleksandra; Žigon, Dušan; Kelly, Steven L.; Komel, Radovan

doi:10.1016/s0045-6535(98)00229-x

Cited by 13 publications

(12 citation statements)

References 23 publications

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“…These hydroxylation sites are distinct from those previously described for Δ 4-5 steroids in reactions with the same fungus, that usually occur at the positions 11β, 14α and 7α. 7,23,24 Such differences may be explained by distinct enzyme/ substrate interactions, arising from the uncommon configuration of digitoxigenin steroidal frame (cis, trans, cis), in comparison to other steroids, or due to the presence of the α,β-unsaturated lactone ring at C-17. Such hypotheses consider that the same hydroxylases do participate in reactions with digitoxigenin and other steroids.…”

Section: Resultsmentioning

confidence: 99%

“…The ecological relations of these organisms include the metabolism of different secondary compounds, a feature sustained by diversified enzymatic systems, both intra and extra cellular, capable of carrying out numerous reactions. [6][7][8] Such attributes suggest fungi as suitable organisms to perform biotransformation reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Difficulties in isolation and stabilization of those enzymes, associated with the necessity of recycling NAD(P)H co-factors, prevent the industrial use of isolated enzymes. 7,10 Intact fungus organisms are therefore alternatively employed in biotransformation reactions. 6,11 The fungus Cochliobolus lunatus and its conidial anamorphous form Curvularia lanata are known for their capacity of hydroxylating Δ 4-5 steroids.…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of digitoxigenin by Cochliobolus lunatus

Pádua¹,

Oliveira²,

Filho³

et al. 2007

J. Braz. Chem. Soc.

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A reação de biotransformação da digitoxigenina (1) por Cochliobolus lunatus foi investigada. Foram realizados experimentos com duração de 4 dias, que resultaram no isolamento de quatro produtos, cujas estruturas químicas foram elucidadas como sendo 1β-hidroxidigitoxigenina (2), 7β-hidroxidigitoxigenina (3), 8β-hidroxidigitoxigenina (4) e digitoxigenona (5). A obtenção desses produtos nas condições empregadas nunca foi anteriormente descrita. A produção da substância 4 em uma reação de biotransformação também é inédita.The biotransformation of digitoxigenin (1) by Cochliobolus lunatus was investigated. The biotransformation reaction was carried out in a 4-day process, resulting in the isolation of four products, whose structures were elucidated as 1β-hydroxydigitoxigenin (2), 7β-hydroxydigitoxigenin (3), 8β-hydroxydigitoxigenin (4) and digitoxigenone (5). The production of these derivatives under the employed conditions has never been described so far. This is also the first report on the production of compound 4 by a biotransformation reaction.Keywords: digitoxigenin, Cochliobolus lunatus, 1β-hydroxydigitoxigenin, 7β-hydroxydigitoxigenin, 8β-hydroxydigitoxigenin, digitoxigenone IntroductionEnzymes are known to possess a wide substrate tolerance by keeping their exquisite catalytic properties with respect to chemo-, regio-and enantio-selectivity, playing an important role in biotransformations. 1 Biotransformation reactions can be accomplished at room temperature and in aqueous medium, presenting itself as a milder alternative to classical chemical reactions, 2-4 being employed for the resolution of racemates and to introduce chiral centers in substrates, among other uses. 5 Fungi are eukaryotic organisms that possess enzyme systems similar to those of mammalians. They usually present highly flexible metabolism, thus accepting varied sources of carbon and nitrogen. The ecological relations of these organisms include the metabolism of different secondary compounds, a feature sustained by diversified enzymatic systems, both intra and extra cellular, capable of carrying out numerous reactions. 6-8 Such attributes suggest fungi as suitable organisms to perform biotransformation reactions.The biotransformation of steroidal compounds by fungi has been extensively evaluated, including reactions with cardiac glycosides (Pádua et al. 9 and references herein; Table 3 of the present work). Digoxin, a Digitalis cardenolide, is still the drug of choice for the treatment of congestive heart failure, acting as a selective inhibitor of the Na + ,K + ATPase enzyme. Biotransformation of cardenolides has been investigated either as a strategy to obtain new derivatives or to convert the A-type cardenolides into the corresponding C-type compounds, which have clinical relevance. 9 The main reactions obtained so far for cardenolide biotransformation were hydroxylation in different positions of the steroidal skeleton, oxidation, glycosylation, epimerization and esterification of the hydroxyl group at C-3 (see Table 3 for references). An...

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biotransformation of digitoxigenin by Cochliobolus lunatus

Pádua¹,

Oliveira²,

Filho³

et al. 2007

J. Braz. Chem. Soc.

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“…CYP51 that impinges on antifungal therapy with CYP51 azole drug inhibitors [44 -46]. In Cochliobolus lunatus, the cytochrome P450 system is of biotechnological interest as the fungus is used in preparation of corticosteroids and CYPs have been associated with detoxification of plant defence compounds [47]. Lah et al [48] reported two CPRs in this fungus where one was associated with primary metabolism and the other with xenobiotic detoxification.…”

Section: Microbial Cytochromes P450 and Their Electron Donorsmentioning

confidence: 99%

Microbial cytochromes P450: biodiversity and biotechnology. Where do cytochromes P450 come from, what do they do and what can they do for us?

Kelly

2013

Phil. Trans. R. Soc. B

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176

131

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The first eukaryote genome revealed three yeast cytochromes P450 (CYPs), hence the subsequent realization that some microbial fungal genomes encode these proteins in 1 per cent or more of all genes (greater than 100) has been surprising. They are unique biocatalysts undertaking a wide array of stereo-and regio-specific reactions and so hold promise in many applications. Based on ancestral activities that included 14a-demethylation during sterol biosynthesis, it is now seen that CYPs are part of the genes and metabolism of most eukaryotes. In contrast, Archaea and Eubacteria often do not contain CYPs, while those that do are frequently interesting as producers of natural products undertaking their oxidative tailoring. Apart from roles in primary and secondary metabolism, microbial CYPs are actual/potential targets of drugs/agrochemicals and CYP51 in sterol biosynthesis is exhibiting evolution to resistance in the clinic and the field. Other CYP applications include the first industrial biotransformation for corticosteroid production in the 1950s, the diversion into penicillin synthesis in early mutations in fungal strain improvement and bioremediation using bacteria and fungi. The vast untapped resource of orphan CYPs in numerous genomes is being probed and new methods for discovering function and for discovering desired activities are being investigated.

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“…It showed a potent inhibitory activity against 11β-hydroxysteroid dehydrogenase, which plays an important role in inflammation, salt retention, hypertension, obesity, diabetes, and occular hypertension [3]. Biotransformation of 11-ketoprogesterone (1) with various microorganisms and plant cell culture has been reported previously [4][5][6][7].…”

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confidence: 96%

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

et al. 2011

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Microbial transformation of 11-ketoprogesterone (1) by the filamentous fungi Fusarium lini was investigated. Biotransformation of 1 with F. lini resulted in the production of ten oxidative metabolites (2-11). Structures of these metabolites were deduced by spectroscopic analysis and seven of them, 5-11, were found to be new metabolites.Keywords: 11-Ketoprogesterone; Steroid; Microbial transformation; Hydroxylation; Filamentous fungi; Fusarium lini.© 2011 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved. doi:10.3329/jsr.v2i2.6221 J. Sci. Res. 3 (2), 347-356 (2011)

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Induction of steroidal hydroxylase activity by plant defence compounds in the filamentous fungus Cochliobolus lunatus

Cited by 13 publications

References 23 publications

Biotransformation of digitoxigenin by Cochliobolus lunatus

Biotransformation of digitoxigenin by Cochliobolus lunatus

Microbial cytochromes P450: biodiversity and biotechnology. Where do cytochromes P450 come from, what do they do and what can they do for us?

Biotransformation of 11-ketoprogesterone by Filamentous Fungus, <i>Fusarium lini</i>

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