Cascate reactions of progesterone by mycelia and culture broth from marine-derived fungus Aspergillus sydowii CBMAI 935

Paula, Samuel Filipe Cardoso de; Porto, André Luiz Meleiro

doi:10.1016/j.bcab.2020.101546

Cited by 8 publications

(4 citation statements)

References 35 publications

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“…Hydroxylation occurs mainly at the 6β and/or 11α positions [1,4,5,24,[29][30][31][32][33][34][35][36][37], but hydroxylation at the 14α [29,31,[33][34][35][36]38,39], 7α [33][34][35]38,39], 7β [34], 11β [30,38], 17α [24,30,32], 9α [31], 8β [31], 16α [32], 15α [32,33,40], 15β [33,34], 21 [1,36] and 12β [24,25] positions is also possible in the fungal cultures. The Baeyer-Villiger oxidation of progesterone is possible for biotransformation by some Aspergillus or Penicillium species [41][42][43][44].…”

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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“…Testololactone is also a steroidal compound used to treat breast cancer, prostate cancer and prostatic hyperplasia. 182 In 2020, Paula et al reported the biosynthesis of testosterone and testololactone by utilizing Baeyer–Villiger oxidation as a key reaction. 182 The conversion was proceeded with the formation of testosterone 216 from progesterone 215 by using Baeyer–Villiger monooxygenase followed by hydrolysis.…”

Section: Review Of Literaturementioning

confidence: 99%

“… 182 In 2020, Paula et al reported the biosynthesis of testosterone and testololactone by utilizing Baeyer–Villiger oxidation as a key reaction. 182 The conversion was proceeded with the formation of testosterone 216 from progesterone 215 by using Baeyer–Villiger monooxygenase followed by hydrolysis. Then, compound 216 further delivered testololactone 3 via dehydrogenation and Baeyer–Villiger oxidation using BVMO ( Scheme 30 ).…”

Section: Review Of Literaturementioning

confidence: 99%

Baeyer–Villiger oxidation: a promising tool for the synthesis of natural products: a review

Fatima,

Zahoor,

Khan

et al. 2024

RSC Adv.

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“…In a good yield, this fungus was able to oxidize progesterone at the C17-site, resulting in the two major products testololactone and testosterone. Additionally, this Baeyer–Villiger reaction-based bio-oxidation revealed the existence of crucial enzymes in this fungus that can aid in related steroid biotransformation [ 121 ]. A. sydowii CBMAI-935 only produced 2′,4-dihydroxy-dihydrochalcone with a yield of 26% from 2′,4-dihydroxy-dihydrochalcone [ 122 ].…”

Section: Industrial and Biotechnological Applicationsmentioning

confidence: 99%

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

Ibrahim,

Mohamed,

Alsaadi

et al. 2023

Marine Drugs

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Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine ecosystems. This fungus can cause aspergillosis in sea fan corals leading to sea fan mortality with subsequent changes in coral community structure. Interestingly, A. sydowi is a prolific source of distinct and structurally varied metabolites such as alkaloids, xanthones, terpenes, anthraquinones, sterols, diphenyl ethers, pyrones, cyclopentenones, and polyketides with a range of bioactivities. A. sydowii has capacity to produce various enzymes with marked industrial and biotechnological potential, including α-amylases, lipases, xylanases, cellulases, keratinases, and tannases. Also, this fungus has the capacity for bioremediation as well as the biocatalysis of various chemical reactions. The current work aimed at focusing on the bright side of this fungus. In this review, published studies on isolated metabolites from A. sydowii, including their structures, biological functions, and biosynthesis, as well as the biotechnological and industrial significance of this fungus, were highlighted. More than 245 compounds were described in the current review with 134 references published within the period from 1975 to June 2023.

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Cascate reactions of progesterone by mycelia and culture broth from marine-derived fungus Aspergillus sydowii CBMAI 935

Cited by 8 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

Baeyer–Villiger oxidation: a promising tool for the synthesis of natural products: a review

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

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