Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1

Wu, Yan; Li, Hui; Zhang, Xiaomei; Gong, Jin‐Song; Rao, Zhiming; Shi, Jin‐Song; Xu, Zhenghong

doi:10.1016/j.molcatb.2015.07.003

Cited by 17 publications

(3 citation statements)

References 35 publications

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“…Its 11α hydroxylation is a key step in synthesising prednisone and prednisolone or dexamethasone, and Rhizopus nigricans is the most widely used microorganism for industry purposes [48]. Other possible hydroxylation positions of this compound are 8β [49], 11β [50], 15β [49] and 15α [51]. A similar transformation to 6β,11α-dihydroxy-16α,17α-epoxyprogesterone was described for Aspergillus ochraceus ATCC 1008 [52].…”

Section: Discussionmentioning

confidence: 99%

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Kozłowska

Sycz

Janeczko

2022

IJMS

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Progesterone biotransformation is worth studying because of the high industrial value of its derivatives. This study investigated the catalytic ability of the entomopathogenic filamentous fungus strain Isaria farinosa KCh KW1.1 to transform progesterone derivatives: 11α-hydroxyprogesterone, 17α-hydroxyprogesterone, 16α,17α-epoxyprogesterone and pregnenolone. In the culture of Isaria farinosa KCh KW1.1, 11α-hydroxyprogesterone was effectively transformed into only one product: 6β,11α-dihydroxyprogesterone. Transformation of 17α-hydroxyprogesterone gave three hydroxy derivatives: 6β,17α-dihydroxyprogesterone, 12β,17α-dihydroxyprogesterone and 6β,12β,17α-trihydroxyprogesterone. Two products: 6β-hydroxy-16α,17α-epoxyprogesterone and 6β,11α-dihydroxy-16α,17α-epoxyprogesterone, were obtained from the 16α,17α-epoxyprogesterone transformation. We isolated two compounds from the biotransformation medium with pregnenolone: 11α-hydroxy-7-oxopregnenolone and 5α,6α-epoxy-3β,11α-dihydroxypregnan-7,20-dione. In this study, we observed only mono- and dihydroxy derivatives of the tested substrates, and the number of obtained products for each biotransformation did not exceed three.

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Section: Discussionmentioning

confidence: 99%

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Kozłowska

Sycz

Janeczko

2022

IJMS

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“…Incubation of 1 resulted in the isolation of 14. Wu et al [80] concluded that the different hydroxylation sites between 11 and 12 suggested that the hydroxyl group or carbonyl group on the substrate at C-17 had influence on the location of introduced hydroxyl groups (Figure 15).…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

“…From the biotransformation of 203 using Corynespora cassiicola, 9α-hydroxycanrenone Biotransformation of Steroids Using Different Microorganisms DOI: http://dx.doi.org /10.5772/intechopen.85849 (208, 30%) was obtained, [96]. Conversion of canrenone (203) by Colletotrichum lini ST-1 gave two hydroxyl compounds, 15α-hydroxy-canrenone (209, 22%) and 11α,15α-dihydroxy-canrenone (210, 47%) ( Figure 27) [80].…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

Biotransformation of Steroids Using Different Microorganisms

Cano-Flores¹,

Gómez²,

Ramos³

2020

Chemistry and Biological Activity of Steroids

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The introduction of a hydroxyl group "biohydroxylation" in the steroid skeleton is an important step in the synthesis of new steroids used physiologically as hormones and active drugs. There are currently about 300 known steroid drugs whose production constitutes the second category within the pharmaceutical market after antibiotics. Several biotransformations at industrial scale have been applied in the production of steroid hormones and drugs, which have functionalized different types of raw materials by means of chemo-, regio-, and stereoselective reactions (hydroxylation, Baeyer-Villiger oxidation, oxidation reactions, reduction of group carbonyl, isomerization, and Michael additions, condensation reactions, among others). In Green Chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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Ultrasonic Cell Grinder Extraction of Cyperenoic Acid from Crotonis Crassifolii Radix and the Activity Assay of the Extract

Jiang

et al. 2022

ChemistrySelect

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It is of great significance to achieve a high‐value usage of Chinese medicine residues. This study developed a green ultrasonic cell grinder extraction (UCGE) method has been developed for cyperenoic acid extraction from water decocted Crotonis Crassifolii Radix. The response surface methodology was introduced for the experimental design. The optimum conditions were as follows: 52 % ethanol concentration, 28 : 1 mL/g ratio of solution‐to‐solid, 500 W extraction power, and 28 min extraction time. Anti‐inflammatory test was performed to investigate the medicinal uses of the extract from the herb residue. The microstructure of the extracted samples was also investigated using scanning electron microscopy to understand the extraction mechanism. A higher extraction yield of 1.016 mg/g and better anti‐inflammatory activity were obtained under UCGE compared to a conventional solvent extraction. Meanwhile, the sample structure was seriously damaged by UCGE. The results show that UCGE is a promising green and efficient technology for extracting functional components, and has great potential in recycling waste resources.

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Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1

Cited by 17 publications

References 35 publications

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Hydroxylation of Progesterone and Its Derivatives by the Entomopathogenic Strain Isaria farinosa KCh KW1.1

Biotransformation of Steroids Using Different Microorganisms

Ultrasonic Cell Grinder Extraction of Cyperenoic Acid from Crotonis Crassifolii Radix and the Activity Assay of the Extract

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