Transformations of Cardio-active Steroids by Microorganisms

Nozaki, Yoshio

doi:10.1271/bbb1961.25.890

Cited by 2 publications

(3 citation statements)

References 7 publications

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“…6,7 In the present work, shortening of the biotransformation reaction time to 5 days afforded the products digoxigenin (4), digoxigenone (5) and digitoxigenone (6) (Figure 3). In order to explain these results, we decided to investigate the biotransformation kinetics of the reaction.…”

Section: Resultsmentioning

confidence: 54%

“…Although we did not detect the transformation of compound 4 into 5, in our 5 days process, digoxigenone (5) seems to be the final transformation product of digitoxigenin (1) by F. ciliatum, once it has been previously obtained in a 100% yield, employing a 11 days process. 6,7 A triangular hydroxylation model has been proposed for the biotransformation of 5-androstanes by F. ciliatum (syn. Calonectria decora) wherein one of the triangle vertices is the electron rich group and the two others are the sites for hydroxylation.…”

Section: Resultsmentioning

confidence: 99%

“…3 The capacity of Fusarium lini and F. ciliatum to promote digitoxigenin hydroxylation at 12 -position has been demonstrated. [4][5][6][7] The second species also promoted oxidation of the C-3 OH and digoxigenone was obtained. 6 F. lini was also investigated for the biotransformation of digitoxin, without success, 5 whereas no report was found on the transformation of this substrate by F. ciliatum.…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of digitoxigenin by Fusarium ciliatum

Pádua¹,

Oliveira²,

Filho³

et al. 2005

J. Braz. Chem. Soc.

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A biotransformação da digitoxigenina (1) por Fusarium ciliatum foi investigada. O cardenolídeo 1 foi obtido a partir da hidrólise ácida da digitoxina e a reação também forneceu os produtos secundários 14-15 -digitoxigenina (2) e 8-14 -digitoxigenina (3). A reação de biotransformação foi realizada em um período de 5 dias e três produtos foram isolados e identificados a partir de análises espectrométricas: digoxigenina (4), digoxigenona (5) e digitoxigenona (6). A obtenção dos dois últimos cardenolídeos nas condições empregadas é inédita. A investigação da cinética da reação de biotransformação indicou 6 como o primeiro produto a ser formado, seguido dos derivados hidroxilados 4 e 5, sugerindo o envolvimento de enzima distintas na hiroxilação em 12 e na oxidação em C-3 da digitoxigenina (1). A reação de biotransformação também foi realizada com a digitoxina, mas F. ciliatum se mostrou incapaz de promover sua hidroxilação.The biotransformation of digitoxigenin (1) by Fusarium ciliatum was investigated. The cardenolide 1 was obtained by the acid hydrolysis of digitoxin and the reaction also afforded two side products, identified as [14][15] -digitoxigenin (2) and 8-14 -digitoxigenin (3) by spectroscopic analysis. The biotransformation reaction was carried out in a 5 days process and three products were isolated and had their structures elucidated as digoxigenin (4), digoxigenone (5) and digitoxigenone (6). The investigation of the biotransformation kinetics disclosed 6 as the first derivative to be formed, followed by the more polar hydroxylated products 4 and 5, suggesting the involvement of different enzymes in 12 hydroxylation and C-3 oxydation of digitoxigenin (1). The production of 5 and 6 under the employed conditions has never been reported. The biotransformation reaction was also undertaken with digitoxin, but F. ciliatum has been unable to promote its hydroxylation.

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Section: Resultsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 99%