Antimicrobial chloro-hydroxylactones derived from the biotransformation of bicyclic halolactones by cultures of Pleurotus ostreatus

Grabarczyk, Małgorzata; Mączka, Wanda; Wińska, Katarzyna; Żarowska, Barbara; Maciejewska, Gabriela; Gębarowska, Elżbieta; Pietr, S J

doi:10.1016/j.bioorg.2020.104250

Cited by 4 publications

(8 citation statements)

References 31 publications

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“…It is worth noting that in this case, the conformation of the cyclohexane ring changed. Similar reactions were previously observed when the fungi Pleurotus ostreatus or Absidia cylindrospora AM336 were used as a biocatalyst [22,23].…”

Section: Discussionsupporting

confidence: 80%

New Hydroxylactones and Chloro-Hydroxylactones Obtained by Biotransformation of Bicyclic Halolactones and Their Antibacterial Activity

Grabarczyk,

Duda-Madej,

Romanenko

et al. 2024

Molecules

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The aim of this study was to obtain new halolactones with a gem-dimethyl group in the cyclohexane ring (at the C-3 or C-5 carbon) and a methyl group in the lactone ring and then subject them to biotransformations using filamentous fungi. Halolactones in the form of mixtures of two diasteroisomers were subjected to screening biotransformations, which showed that only compounds with a gem-dimethyl group located at the C-5 carbon were transformed. Strains from the genus Fusarium carried out hydrolytic dehalogenation, while strains from the genus Absidia carried out hydroxylation of the C-7 carbon. Both substrates and biotransformation products were then tested for antimicrobial activity against multidrug-resistant strains of both bacteria and yeast-like fungi. The highest antifungal activity against C. dubliniensis and C. albicans strains was obtained for compound 5b, while antimicrobial activity against S. aureus MRSA was obtained for compound 4a.

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Section: Discussionsupporting

confidence: 80%

New Hydroxylactones and Chloro-Hydroxylactones Obtained by Biotransformation of Bicyclic Halolactones and Their Antibacterial Activity

Grabarczyk,

Duda-Madej,

Romanenko

et al. 2024

Molecules

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“…In the next step, the enantiomeric excesses of these compounds were determined using a column with chiral filling (Supplementary Materials, Figures S41-S43). The retention times of the analyzed compounds were consistent with our previous experience with structurally similar compounds [20,26]. The results are presented in Table 3.…”

Section: Preparative Biotransformation Of Halolactones 5 and 6 Analys...supporting

confidence: 88%

“…The second time, the microorganisms inducing the formation of such compounds were edible fungi of the genus Pleurotus ostreatus. At that time, the only effectively transformed substrate was chlorolactone with four methyl groups, two at C-4 carbon one each at C-6 and C-7 carbon [26].…”

Section: Preparative Biotransformation Of Halolactones 5 and 6 Analys...mentioning

confidence: 99%

“…As a result, hydroxylactones with a different conformation than halolactones obtained by chemical synthesis were obtained. It is also possible to obtain halo-hydroxylactones, compounds in which the halogen atom remains intact, and additionally a hydroxyl group is introduced [20,25,26]. It is worth emphasizing that, due to the variety of enzymes capable of catalyzing the hydroxylation of xenobiotics, it is not possible to predict the position of hydroxylation without experimental basic research.…”

Section: Introductionmentioning

confidence: 99%

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New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

et al. 2021

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The subject of the research was to determine the ability of the filamentous fungi to biotransform bicyclic halolactones containing two methyl groups in their structure. By chemical synthesis three bicyclic halolactones with two methyl groups, one in the cyclohexane ring and one in the lactone ring, were obtained: 2-chloro-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, 2-bromo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, and 2-iodo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one. These compounds were formed as mixtures of two diastereoisomers. The obtained halolactones (as mixture of two diastereoisomers) were subjected to screening biotransformation with the use of eight strains of filamentous fungi: Fusarium culmorum AM10, F. avenaceum AM12, F. semitectum AM20, F. solani AM203, Absidia coerulea AM93, A. cylindrospora AM336, Penicillium chermesinum AM113, P. frequentans AM351. Two of the substrates, 2-bromo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one and 2-iodo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, were hydroxylated without removing the halogen atom from the molecule, giving 2-bromo-7-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, 2-bromo-5-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, and 2-iodo-7-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one as products. The hydroxylation capacity was demonstrated by strains of Absidia cylindrospora AM336, Fusarium avenaceum AM12, and F. solani AM203. The structures of all lactones were determined on the basis spectroscopic data.

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“…Removal efficiency of bicalutamide, lamotrigine, and metformin was 43%, 73%, and 59%, respectively, from water [91] Chloro-hydroxyl-actones Culture medium for 72 h Mushroom bio-transformed bicyclic halolactones to chlorolactones [92] Triclosan (5, 10, 20, 30,…”

Section: Pollutant Details Growth Conditionsmentioning

confidence: 99%

Green Biotechnology of Oyster Mushroom (Pleurotus ostreatus L.): A Sustainable Strategy for Myco-Remediation and Bio-Fermentation

et al. 2022

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The field of biotechnology presents us with a great chance to use many organisms, such as mushrooms, to find suitable solutions for issues that include the accumulation of agro-wastes in the environment. The green biotechnology of mushrooms (Pleurotus ostreatus L.) includes the myco-remediation of polluted soil and water as well as bio-fermentation. The circular economy approach could be effectively achieved by using oyster mushrooms (Pleurotus ostreatus L.), of which the substrate of their cultivation is considered as a vital source for producing biofertilizers, animal feeds, bioenergy, and bio-remediators. Spent mushroom substrate is also considered a crucial source for many applications, including the production of enzymes (e.g., manganese peroxidase, laccase, and lignin peroxidase) and bioethanol. The sustainable management of agro-industrial wastes (e.g., plant-based foods, animal-based foods, and non-food industries) could reduce, reuse and recycle using oyster mushrooms. This review aims to focus on the biotechnological applications of the oyster mushroom (P. ostreatus L.) concerning the field of the myco-remediation of pollutants and the bio-fermentation of agro-industrial wastes as a sustainable approach to environmental protection. This study can open new windows onto the green synthesis of metal-nanoparticles, such as nano-silver, nano-TiO2 and nano-ZnO. More investigations are needed concerning the new biotechnological approaches.

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Antimicrobial chloro-hydroxylactones derived from the biotransformation of bicyclic halolactones by cultures of Pleurotus ostreatus

Cited by 4 publications

References 31 publications

New Hydroxylactones and Chloro-Hydroxylactones Obtained by Biotransformation of Bicyclic Halolactones and Their Antibacterial Activity

New Hydroxylactones and Chloro-Hydroxylactones Obtained by Biotransformation of Bicyclic Halolactones and Their Antibacterial Activity

New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

Green Biotechnology of Oyster Mushroom (Pleurotus ostreatus L.): A Sustainable Strategy for Myco-Remediation and Bio-Fermentation

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