Microbial transformation of oral contraceptive ethisterone by Aspergillus niger and Cunninghamella blakesleeana

Aziz, Ambreen; Bano, Saira; Atia-tul-Wahab, *; Choudhary, Muhammad Iqbal

doi:10.1016/j.steroids.2019.108467

Cited by 8 publications

(4 citation statements)

References 15 publications

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“…In the course of their investigations, the researchers successfully synthesized silylated derivatives of ethisterone, a pharmacological agent used in the treatment of gynecological disorders. [152] From a mechanistic perspective, the process initiates with the excitation of the photocatalyst by light, leading to the formation of an excited state, which is subsequently quenched by quinuclidine to generate a hydrogen atom transfer (HAT) reagent and a highly reducible [4CzIPN] *À species. The HAT reagent, derived from quinuclidine, initiates a radical reaction with the silane, generating a silyl radical.…”

Section: From Hydrosilanesmentioning

confidence: 99%

“…Notably, not only tertiary silanes but also dihydrosilanes such as diphenylsilane and di‐ tert ‐butylsilane exhibited reactivity, affording the desired products with (phenylethynyl) sulfonyl benzene in yields of 76% and 70%, respectively. In the course of their investigations, the researchers successfully synthesized silylated derivatives of ethisterone, a pharmacological agent used in the treatment of gynecological disorders [152] …”

Section: Synthesis Of 1‐silyl‐1‐alkynesmentioning

confidence: 99%

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Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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This contribution offers a comprehensive overview of methods for forging sp C–Si bonds. Over time, alkynylsilanes (silylacetylenes), once considered mere byproducts of hydrosilylation processes, have become essential building blocks in organic synthesis. This literature review traces the evolution of their synthesis, from traditional methodologies relying on organolithium and organomagnesium compounds to more advanced cross‐coupling reactions involving hydro‐ and carbosilanes. Focused primarily on the past 25 years (2000‐2024), it also extensively references significant historical breakthroughs. By analyzing synthetic methodologies, the review not only offers a comprehensive survey of the current state of knowledge but also identifies areas for improvement. Furthermore, to emphasize the importance of 1‐alkynylsilanes (1‐silyl‐1‐alkynes), selected applications of these compounds are highlighted, confirming their significant potential in organic synthesis.

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Section: From Hydrosilanesmentioning

confidence: 99%

Section: Synthesis Of 1‐silyl‐1‐alkynesmentioning

confidence: 99%

Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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“…Generally, supplementary methods can be used to obtain a sufficient sample amount of metabolites, including chemical methods [11] and small experimental animal models [15], microsomal preparations [16,17], enzyme-catalyzed reactions [18,19], microbial transformation [11,20] and so on. Compared with other methods, microbial transformation is more convenient and economical, especially with the advantages of in vitro large-scale preparation [20][21][22][23][24]. In particular, the filamentous zygote fungus C. elegans has been shown to possess a human-like cytochrome P450 monooxygenase system, including the CYP509A1 isoenzyme that is similar to the CYP51 family, thus producing similar metabolic profiles to mammalian animals [25,26].Sufficient samples for structural characterization based on NMR techniques as well as the evaluation of bioactivity and toxicity can thus be acquired.…”

Section: Introductionmentioning

confidence: 99%

Comprehensive Metabolic Profiling of Euphorbiasteroid in Rats by Integrating UPLC-Q/TOF-MS and NMR as Well as Microbial Biotransformation

Xiao¹,

Wei

Xin

et al. 2022

Metabolites

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Euphorbiasteroid, a lathyrane-type diterpene from Euphorbiae semen (the seeds of Euphorbia lathyris L.), has been shown to have a variety of pharmacological effects such as anti-tumor and anti-obesity. This study aims to investigate the metabolic profiles of euphorbiasteroid in rats and rat liver microsomes (RLMs) and Cunninghamella elegans bio-110930 by integrating ultra-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry (UPLC-Q/TOF-MS), UNIFI software, and NMR techniques. A total of 31 metabolites were identified in rats. Twelve metabolites (M1–M5, M8, M12–M13, M16, M24–M25, and M29) were matched to the metabolites obtained by RLMs incubation and the microbial transformation of C. elegans bio-110930 and their structures were exactly determined through analysis of NMR spectroscopic data. In addition, the metabolic pathways of euphorbiasteroid were then clarified, mainly including hydroxylation, hydrolysis, oxygenation, sulfonation, and glycosylation. Finally, three metabolites, M3 (20-hydroxyl euphorbiasteroid), M24 (epoxylathyrol) and M25 (15-deacetyl euphorbiasteroid), showed significant cytotoxicity against four human cell lines with IC50 values from 3.60 μM to 40.74 μM. This is the first systematic investigation into the in vivo metabolic pathways of euphorbiasteroid and the cytotoxicity of its metabolites, which will be beneficial for better predicting the metabolism profile of euphorbiasteroid in humans and understanding its possible toxic material basis.

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“…Compared with other methods, microbial biotransformation is more convenient and cost-effective, especially with the advantage of large-scale preparation in vitro. [17][18][19][20][21] Particularly, the fungus Cunninghamella elegans has been shown to possess the cytochrome P450 monooxygenase system similar to mammals, which could promote the reactions catalyzed by human CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A4, thus producing similar metabolic proles to mammals. 22,23 However, the presence and abundance of the metabolites determined by microbial transformation may not be an out-and-out representation of in vivo metabolites.…”

Section: Introductionmentioning

confidence: 99%