Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture

Janeczko, Tomasz; Świzdor, Alina; Dmochowska-Gładysz, Jadwiga; Białońska, Agata; Ciunik, Zbigniew; Kostrzewa-Susłow, Edyta

doi:10.1016/j.molcatb.2012.05.009

Cited by 25 publications

(19 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Steroid compounds are very common in pharmacy and medicine because of their variety of biological activities [ 1 , 2 , 3 ]. Hydroxylation of steroid compounds by microbial monooxygenases, which are similar to mammalian cytochromes P450, is a source of molecules of high biological activity and key intermediates in chemical synthesis [ 4 , 5 , 6 , 7 ]. The first known hydroxylated corticosteroid is cortisol (hydrocortisone), which is produced by the adrenal glands from cortisone by the 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) in response to stress and low blood glucose concentrations.…”

Section: Introductionmentioning

confidence: 99%

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

et al. 2017

Self Cite

View full text Add to dashboard Cite

The catalytic activity of enzymes produced by an entomopathogenic filamentous fungus (Isaria fumosorosea KCh J2) towards selected steroid compounds (androstenedione, adrenosterone, progesterone, 17α-methyltestosterone and dehydroepiandrosterone) was investigated. All tested substrates were efficiently transformed. The structure of the substrate has a crucial impact on regio- and stereoselectivity of hydroxylation since it affects binding to the active site of the enzyme. Androstenedione was hydroxylated in the 7α-position to give a key intermediate in the synthesis of the diuretic-7α-hydroxyandrost-4-ene-3,17-dione with 82% conversion. Adrenosterone and 17α-methyltestosterone were hydroxylated in the 6β-position. Hydroxylated derivatives such as 15β-hydroxy-17α-methyltestosterone and 6β,12β-dihydroxy-17α-methyltestosterone were also observed. In the culture of Isaria fumosorosea KCh J2, DHEA was effectively hydroxylated in the C-7 position and then oxidized to give 7-oxo-DHEA, 3β,7α- and 3β,7β-dihydroxy-17a-oxa-d-homo-androst-5-ene-17-one. We obtained 7β-OH-DHEA lactone with 82% yield during 3 days transformation of highly concentrated (5 g/L) DHEA.

show abstract

Section: Introductionmentioning

confidence: 99%

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…For many years, our team has conducted research on microbial functionalization of compounds of natural origin, including steroid systems . Among these transformations, the hydroxylation reactions in an inactivated position of a transformed compound are of particular importance.…”

mentioning

confidence: 99%

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

2016

Self Cite

View full text Add to dashboard Cite

Metabolism of steroids in healthy and unhealthy human organs is the subject of extensive clinical and biomedical studies. For this kind of investigations, it is essential that the reference samples of new derivatives of natural, physiologically active steroids (especially those difficult to achieve in the chemical synthesis) become available. This study demonstrated for the first time transformation of 7-oxo-DHEA-a natural metabolite of DHEA, using Syncephalastrum racemosum cells. The single-pulse fermentation of substrate produced two new hydroxy metabolites: 1β,3β-dihydroxy-androst-5-en-7,17-dione and 3β,12β-dihydroxy-androst-5-en-7,17-dione, along with the earlier reported 3β,9α-dihydroxy-androst-5-en-7,17-dione and 3β,17β-dihydroxy-androst-5-en-7-one. Simultaneously, the same metabolites, together with small quantities of 7α- and 7β-hydroxy-DHEA, as well as the products of their reduction at the C-17 were obtained after transformation of DHEA under pulse-feeding of the substrate. The observed reactions suggested that this micro-organism contains enzymes exhibiting similar activity to those present in human cells. Thus, the resulting compounds can be considered as potential components of the eukaryotic, including human, metabolome.

show abstract

“…Deformação axial e angular de C-(C=O) Foram encontradas referências para dois estereoisômeros: 7β,15β-di-hidroxiprogesterona 74 …”

unclassified

“…inicalmente proposto pelas análises de RMN com os resultados preliminares que possui discordância entre os valores de deslocamento químico descritos na literatura 74 e experimental para os carbonos C-7 e C-15, mas há concordância entre os valores de deslocamento químico da literatura e experimentais para os hidrogênios H-7β e H-15β. Porém, é maior que 70% a probabilidade de ser o isômero de configuração 7α,15β, segundo mensagem enviada pelo referido pesquisador por correio eletrônico, transcrita abaixo:…”

unclassified

“…Embora a 15β-hidroxiprogesterona seja descrita na literatura 74 Os dados da literatura mostram que as biotransformações do 17α-etinilestradiol são principalmente reações de hidroxilação e os carbonos que sofreram esse tipo de oxidação não tinham algum impedimento estéreo. Reações do tipo Baeyer-Villiger são descritas na literatura 110 , porém produtos deste tipo de oxidação não foram observados nas triagens.…”

unclassified

See 1 more Smart Citation

Estudo da ocorrência de reações de bio-oxidação dos esteroides progesterona e 17α-etinilestradiol por fungos de ambiente marinho

Paula¹

View full text Add to dashboard Cite

Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture

Cited by 25 publications

References 27 publications

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Estudo da ocorrência de reações de bio-oxidação dos esteroides progesterona e 17α-etinilestradiol por fungos de ambiente marinho

Contact Info

Product

Resources

About

Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture

Cited by 25 publications

References 27 publications

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

Isaria fumosorosea KCh J2 Entomopathogenic Strain as an Effective Biocatalyst for Steroid Compound Transformations

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Estudo da ocorrência de reações de bio-oxidação dos esteroides progesterona e 17&#945;-etinilestradiol por fungos de ambiente marinho

Contact Info

Product

Resources

About

Estudo da ocorrência de reações de bio-oxidação dos esteroides progesterona e 17α-etinilestradiol por fungos de ambiente marinho