Acceleration of Microbial Hydroxylations of Digitoxigenin by the Addition of C<sub>21</sub>⊿-3-Ketosteroids

Nozaki, Yoshio; Masuo, Eitarō; Satoh, Daisuke

doi:10.1080/00021369.1962.10857989

Cited by 3 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The extracts were concentrated to dryness in a rotary evaporator, and the residue was dissolved in 5 ml of ethanol. Aliquots (10 ,ul) were spotted on thin-layer plates (Kiesel gel 60 F254; E. Merck AG), which were developed with chloroform-acetone-acetic acid (100:100:1 [vol/vol/ vol]). After drying, the plates were sprayed with concentrated sulfuric acid and heated at 160°C for 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…Screening of microorganisms. Until this study, no fungi have been found that convert LTCA to UDCA, although several have been reported to hydroxylate steroids at the C-7-position: Curvularia lunata converts progesterone to 7a,14adihydroxyprogesterone (14), Curvularia fallax and Curvularia pallescens convert 11-deoxycortisone to 7a,21-dihydroxypregn-4-ene-3,20dione (9), Rhizopus nigricans transforms 4methyltestosterone to 4-methyl-7p-hydroxytestosterone (13), and Rhizopus nigricans ATCC 62276 hydroxylates digitoxigenin to 7,B-hydroxydigitoxigenin (10). None of the steroid-hydroxylating fungi listed in American Type Culture Collection Catalogue ofStrains is registered as a transformer of LTCA to UDCA.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Sawada

Kulprecha

Nilubol

et al. 1982

Appl Environ Microbiol

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Sawada

Kulprecha

Nilubol

et al. 1982

Appl Environ Microbiol

View full text Add to dashboard Cite

show abstract

“…Absidiu orchidis monohydroxylates pregnane derivatives in the 6/3,7cr,l lo-or 1 l/3-position. In cardenolides and bufadienolides the hydroxylation occurs mainly in l/3-and 7/I-position [29]. -(-)-Camphorquinone was transformed to a mixture consisting of 3-endo-hydroxycamphor (40%) 3-exo-hydroxy-camphor (30%), and 2-endo-hydroxy-epi-camphor (30%) by an aqueous suspension of the mycelium of Absidia orchidis [ (t)-Fenchone was hydroxylated by Absidia orchidis to 6-exo-hydroxy-fenchone and to 5-exo-hydroxyfenchone [3 l] (fig.…”

Section: P81-hydroxyl Groups Introduced Are Equatorial and Nearlymentioning

confidence: 99%

Transformation of organic compounds by microbial enzymes

Tamm

1974

FEBS Letters

View full text Add to dashboard Cite

“…Such hypotheses consider that the same hydroxylases do participate in reactions with digitoxigenin and other steroids. In this sense, Nozaki et al 25 improved the 7β hydroxylation of digitoxigenin by Absidia coerulea, Rhizopus oryzae and Rhizopus stolonifer after pre-incubation with progesterone and deoxycorticosterone. Such result demonstrates that monooxygenases induced by Δ 4-5 steroids are also capable of hydroxylating digitoxigenin.…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of digitoxigenin by Cochliobolus lunatus

Pádua¹,

Oliveira²,

Filho³

et al. 2007

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

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...

show abstract

Acceleration of Microbial Hydroxylations of Digitoxigenin by the Addition of C₂₁⊿-3-Ketosteroids

Cited by 3 publications

References 1 publication

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Transformation of organic compounds by microbial enzymes

Biotransformation of digitoxigenin by Cochliobolus lunatus

Contact Info

Product

Resources

About

Acceleration of Microbial Hydroxylations of Digitoxigenin by the Addition of C21⊿-3-Ketosteroids

Cited by 3 publications

References 1 publication

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Transformation of organic compounds by microbial enzymes

Biotransformation of digitoxigenin by Cochliobolus lunatus

Contact Info

Product

Resources

About

Acceleration of Microbial Hydroxylations of Digitoxigenin by the Addition of C₂₁⊿-3-Ketosteroids