Microbiological reduction of steroidal ketones using the thermophilic bacteriumCaldariella acidophila

Sodano, G.; Trabucco, Armando E.; Rosa, Mario De; Gambacorta, Agata

doi:10.1007/bf01954920

Cited by 9 publications

(4 citation statements)

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“…Several thermophilic bacterial species have been reported to carry out distinct structural modifications of steroids [19][20][21]47], while sterol degradation by thermophilic microorganisms has not been studied so far. As shown in this research, thermophilic S. hirsuta transformed cholesterol (Figure 1).…”

Section: Discussionmentioning

confidence: 99%

“…Besides, higher steroid solubility at elevated temperatures is favorable for steroid bioconversion performance. However, data on steroid bioconversion by thermophilic bacteria are scarce and pertain mainly to distinct reactions, such as progesterone conversion by Bacillus thermoglucosidasius (=Parageobacillus thermoglucosidasius) [19] and Geobacillus kaustophilus [20] and reduction of the 3-keto group as well as the ∆ 4 -double bond in various steroid ketones by the extremely thermophilic bacterium Calderiella acidophila [21].…”

Section: Introductionmentioning

confidence: 99%

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Steroid Metabolism in Thermophilic Actinobacterium Saccharopolyspora hirsuta VKM Ac-666T

et al. 2021

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The application of thermophilic microorganisms opens new prospects in steroid biotechnology, but little is known to date on steroid catabolism by thermophilic strains. The thermophilic strain Saccharopolyspora hirsuta VKM Ac-666T has been shown to convert various steroids and to fully degrade cholesterol. Cholest-4-en-3-one, cholesta-1,4-dien-3-one, 26-hydroxycholest-4-en-3-one, 3-oxo-cholest-4-en-26-oic acid, 3-oxo-cholesta-1,4-dien-26-oic acid, 26-hydroxycholesterol, 3β-hydroxy-cholest-5-en-26-oic acid were identified as intermediates in cholesterol oxidation. The structures were confirmed by 1H and 13C-NMR analyses. Aliphatic side chain hydroxylation at C26 and the A-ring modification at C3, which are putatively catalyzed by cytochrome P450 monooxygenase CYP125 and cholesterol oxidase, respectively, occur simultaneously in the strain and are followed by cascade reactions of aliphatic sidechain degradation and steroid core destruction via the known 9(10)-seco-pathway. The genes putatively related to the sterol and bile acid degradation pathways form three major clusters in the S. hirsuta genome. The sets of the genes include the orthologs of those involved in steroid catabolism in Mycobacterium tuberculosis H37Rv and Rhodococcus jostii RHA1 and related actinobacteria. Bioinformatics analysis of 52 publicly available genomes of thermophilic bacteria revealed only seven candidate strains that possess the key genes related to the 9(10)-seco pathway of steroid degradation, thus demonstrating that the ability to degrade steroids is not widespread among thermophilic bacteria.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Steroid Metabolism in Thermophilic Actinobacterium Saccharopolyspora hirsuta VKM Ac-666T

et al. 2021

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“…Another thermophilic bacterium was reported to perform reduction of the progesterone C20 carbonyl group to 20α-or 20β-hydroxy group along with the hydroxylation at C6 (Smith et al 1992). Regio-and stereospeci c reduction of the 3-keto group as well as the Δ4-double bond in various steroid ketones of the androstane and pregnane series was carried out by the extremely thermophilic bacterium Calderiella acidophila (Sodano et al 1982). The strain of Geobacillus kaustophilus hydroxylated progesterone and testosterone (Al-Tamimi et al 2010).…”

Section: Read Full License Introductionmentioning

confidence: 99%

Steroid Metabolism In Thermophilic Actinobacteria Saccharopolyspora Hirsuta Subsp. Hirsuta VKM Ac-666T

Lobastova

Фокина

Tarlachkov

et al. 2021

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Application of thermophile microorganisms opens new prospects in steroid biotechnology, however little is known on steroid catabolism by the thermophile strains.The thermophilic Saccharopolyspora hirsuta subsp. hirsuta strain VKM Ac-666T is capable of structural modification of different steroids, and fully degrades cholesterol. The intermediates of the cholesterol degradation pathway were identified as cholest-4-en-3-one, cholesta-1,4-dien-3-one, 26-hydroxycholest-4-en-3-one, 3-oxo-cholest-4-en-26-oic acid, 3-oxo-cholesta-1,4-dien-26-oic acid, 26-hydroxycholesterol, 3β-hydroxy-cholest-5-en-26-oic acid by MS, and H1- and C13-NMR analyses. The data evidence sterol degradation by the strain occurs simultaneously through the aliphatic side chain hydroxylation at C26 and the A-ring modification that are putatively catalyzed by cytochrome P450 monooxygenase CYP125 and cholesterol oxidase, respectively.The genes orthologous to those related to the sterol side chain degradation, steroid core rings A/B and C/D disruption and the steroid uptake were revealed. Most of the genes related to steroid degradation are grouped in three clusters. The sets of the genes putatively involved in steroid catabolism and peculiarities of their organization in S. hirsuta are discussed.Despite steroids abundancy in the environments, the ability to degrade them is not widespread among thermophilic bacteria as follows from the bioinformatic analysis of 52 publicly available genomes. Only seven candidate strains were revealed to possess the key genes related to the only known 9(10)-seco pathway of steroid degradation.The results contribute to the knowledge on diversity of microbial steroid degraders, the features of sterol catabolism by thermophilic actinobacteria and could be useful for application in the pharmaceutical and environmental biotechnology.

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“…Однако сообщения об использовании термофильных бактерий, способных специфически модифицировать стероидные соединения, крайне редки (3). Сообщалось о способности лишь некоторых термофильных микроорганизмов модифицировать стероиды (4)(5)(6)(7)(8)(9). Умеренно термофильный актинобактериальный штамм Saccharopolyspora hirsuta subsp.…”

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Полногеномное секвенирование термофильного штамма Saccharopolyspora hirsuta subsp. hirsuta ВКМ Ac-666T, перспективного для биотехнологии стероидов

Фокина¹,

Lobastova²,

Брагин³

et al. 2019

VI Пущинская Школа-Конференция «Биохимия, Физиология И Биосферная Роль Микроорганизмов»: Сборник Тезисов

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Microbiological reduction of steroidal ketones using the thermophilic bacteriumCaldariella acidophila

Cited by 9 publications

References 5 publications

Steroid Metabolism in Thermophilic Actinobacterium Saccharopolyspora hirsuta VKM Ac-666T

Steroid Metabolism in Thermophilic Actinobacterium Saccharopolyspora hirsuta VKM Ac-666T

Steroid Metabolism In Thermophilic Actinobacteria Saccharopolyspora Hirsuta Subsp. Hirsuta VKM Ac-666T

Полногеномное секвенирование термофильного штамма Saccharopolyspora hirsuta subsp. hirsuta ВКМ Ac-666T, перспективного для биотехнологии стероидов

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