Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives

Microbial strains of the genera Dietzia , Micrococcus , Pseudomonas , Rhodococcus , Gordonia , Streptomyces , Pseudomonas , Bacillus , Penicillium , Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction....

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Published in:	Applied microbiology and biotechnology Vol. 100; no. 19; pp. 8371 - 8384
Main Authors:	Stompor, Monika, Kałużny, Mateusz, Żarowska, Barbara
Format:	Journal Article
Language:	English
Published:	Berlin/Heidelberg Springer Berlin Heidelberg 01-10-2016 Springer Springer Nature B.V
Subjects:	Alcohol Analysis Aromatic compounds Bacillus Biomedical and Life Sciences Biotechnological Products and Process Engineering Biotechnology Biotransformation Cancer Chalcone - metabolism Chemical properties Chemical structure Dehydrogenases Dietzia Flavonoids Gordonia Lactobacillus Lactobacillus - metabolism Life Sciences Magnetic Resonance Spectroscopy Metabolism Metabolites Microbial Genetics and Genomics Microbiology Micrococcus Microorganisms Oxidation-Reduction Penicillium Probiotics Pseudomonas Rhodococcus Rhodococcus - metabolism Rhodotorula Rhodotorula - metabolism Rhodotorula rubra Streptomyces Studies United States Dihydrochalcones Microbial reduction Chalcones Rhodococcus Gordonia Lactobacillus
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Abstract	Microbial strains of the genera Dietzia , Micrococcus , Pseudomonas , Rhodococcus , Gordonia , Streptomyces , Pseudomonas , Bacillus , Penicillium , Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2′-hydroxychalcone and 4′-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure–activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4′-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4′- O -methylphenyl)-2-propan-1-ol, respectively, which was confirmed by 1 H NMR and 13 C NMR analysis.
AbstractList	Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2'-hydroxychalcone and 4'-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure-activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4'-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4'-O-methylphenyl)-2-propan-1-ol, respectively, which was confirmed by .sup.1H NMR and .sup.13C NMR analysis. Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2'-hydroxychalcone and 4'-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure-activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4'-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4'-O-methylphenyl)-2-propan-1-ol, respectively, which was confirmed by (1)H NMR and (13)C NMR analysis. Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2'-hydroxychalcone and 4'-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure-activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4'-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4'-O-methylphenyl)-2-propan-1-ol, respectively, which was confirmed by 1H NMR and 13C NMR analysis. Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2'-hydroxychalcone and 4'-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure-activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4'-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4'-O-methylphenyl)-2-p ropan-1-ol, respectively, which was confirmed by super(1)H NMR and super(13)C NMR analysis. Microbial strains of the genera Dietzia , Micrococcus , Pseudomonas , Rhodococcus , Gordonia , Streptomyces , Pseudomonas , Bacillus , Penicillium , Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2′-hydroxychalcone and 4′-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure–activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4′-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4′- O -methylphenyl)-2-propan-1-ol, respectively, which was confirmed by 1 H NMR and 13 C NMR analysis.
Audience	Academic
Author	Żarowska, Barbara Stompor, Monika Kałużny, Mateusz
Author_xml	– sequence: 1 givenname: Monika surname: Stompor fullname: Stompor, Monika email: monika.stompor@gmail.com organization: Centre for Innovative Research in Medical and Natural Sciences, Faculty of Medicine, University of Rzeszów, Department of Chemistry, Wrocław University of Environmental and Life Sciences – sequence: 2 givenname: Mateusz surname: Kałużny fullname: Kałużny, Mateusz organization: Department of Chemistry, Wrocław University of Environmental and Life Sciences – sequence: 3 givenname: Barbara surname: Żarowska fullname: Żarowska, Barbara organization: Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences
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Publisher	Springer Berlin Heidelberg Springer Springer Nature B.V
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Snippet	Microbial strains of the genera Dietzia , Micrococcus , Pseudomonas , Rhodococcus , Gordonia , Streptomyces , Pseudomonas , Bacillus , Penicillium ,... Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and...
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SubjectTerms	Alcohol Analysis Aromatic compounds Bacillus Biomedical and Life Sciences Biotechnological Products and Process Engineering Biotechnology Biotransformation Cancer Chalcone - metabolism Chemical properties Chemical structure Dehydrogenases Dietzia Flavonoids Gordonia Lactobacillus Lactobacillus - metabolism Life Sciences Magnetic Resonance Spectroscopy Metabolism Metabolites Microbial Genetics and Genomics Microbiology Micrococcus Microorganisms Oxidation-Reduction Penicillium Probiotics Pseudomonas Rhodococcus Rhodococcus - metabolism Rhodotorula Rhodotorula - metabolism Rhodotorula rubra Streptomyces Studies
Title	Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives
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