Non-terpenoid biotransformations by Mucor species

Silva, Eliane de Oliveira; Furtado, Niege Araçari Jacometti Cardoso; Aleu, Josefina; Collado, Isidro González

doi:10.1007/s11101-014-9374-0

Cited by 16 publications

(8 citation statements)

References 74 publications

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“…Because of the promising biological activities of diterpenes, there is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures, which are difficult to achieve using chemical reactions [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

An Overview of Biotransformation and Toxicity of Diterpenes

2018

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Diterpenes have been identified as active compounds in several medicinal plants showing remarkable biological activities, and some isolated diterpenes are produced at commercial scale to be used as medicines, food additives, in the synthesis of fragrances, or in agriculture. There is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures. Biotransformation processes also have a crucial role in drug development and/or optimization. The understanding of the metabolic pathways for both phase I and II biotransformation of new drug candidates is mandatory for toxicity and efficacy evaluation and part of preclinical studies. This review presents an overview of biotransformation processes of diterpenes carried out by microorganisms, plant cell cultures, animal and human liver microsomes, and rats, chickens, and swine in vivo and highlights the main enzymatic reactions involved in these processes and the role of diterpenes that may be effectively exploited by other fields.

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Section: Introductionmentioning

confidence: 99%

An Overview of Biotransformation and Toxicity of Diterpenes

2018

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“…Further reduction of the hemiketal and O-methylation of the hydroxyl group could explain how the fungus converted the 3,4,5-trimethyoxyphenyl group of 16 into the methoxy group of the metabolite 16a. In addition, the trypanocidal activities of (-)-grandisin (16) and its metabolite (16a) were evaluated and demonstrated to be quite similar. This finding highlights that the elimination of one of the 3,4,5-trimethoxyphenyl rings did not hinder trypanocidal activity, which may be important for the synthetic planning of new drug candidates.…”

Section: Biotransformation Reactions Catalyzed By Brazilian Endophytimentioning

confidence: 99%

“…Nova Figure 5. Bioactive compounds used as substrates (16)(17)(18)(19)(20)(21)(22) in biotransformations by Brazilian endophytic fungi and their derivatives…”

Section: Biotransformation Reactions Catalyzed By Brazilian Endophytimentioning

confidence: 99%

“…Biotransformations catalyzed by filamentous fungi are considered economically competitive technologies for the modification of chemicals, leading to structural diversification of drugs or other bioactive substances. 16 The reactions catalyzed by filamentous fungi have a high degree of selectivity and attend to the Green Chemistry principles. When biotransformation reactions using fungi are employed in modifications of the chemical structures of natural products, limitations associated with the obtaining such substances on low yields can be circumvented.…”

Section: Introductionmentioning

confidence: 99%

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Endophytic Fungi From the Brazilian Flora and Their Employment in Biotransformation Reactions

Santos¹,

Silva²

2019

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The biotransformation reactions are used as a successful alternative to derivatization by the traditional chemistry because they conduct to uncommon reactions, which would hardly be carried out by chemical synthesis. A wide diversity of compounds may be metabolized by fungi, leading to chemical derivatives through selective reactions that work under ecofriendly conditions. Endophytic fungi live in symbiosis with health tissues of plants. The employment of endophytic fungi as enzymatic sources to biotransformation reactions is very promising since these microorganisms came from uncommon and underexplored habitat. The environmental conditions directly influence the composition of the endophytic microbiota and its genetic expression, which could change also the production of the enzymes. The extraordinary richness of the Brazilian biodiversity is a key factor in the diversification of the endophytic community. The present review presents a mapping of the biotransformation reactions catalyzed by Brazilian endophytic fungi. Our findings contribute both to the appreciation of these fungi in the chemical derivatization and for the preservation of the Brazilian species.

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“…Biotransformation processes have an interesting diversity, which allows for diverse products to be obtained from a single substrate [20]. Moreover, some chemical transformations that cannot be performed through the traditional synthetic methods are readily obtained using the biotransformation approach in ecofriendly reactions [21]. Within this context, the microbiological transformation of diterpenes has been studied to achieve the specific hydroxylation of unactivated C–H bonds, which is difficult to prepare using chemical methods [22].…”

Section: Introductionmentioning

confidence: 99%

Mapping the Biotransformation of Coumarins through Filamentous Fungi

et al. 2019

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Natural coumarins are present in remarkable amounts as secondary metabolites in edible and medicinal plants, where they display interesting bioactivities. Considering the wide enzymatic arsenal of filamentous fungi, studies on the biotransformation of coumarins using these microorganisms have great importance in green chemical derivatization. Several reports on the biotransformation of coumarins using fungi have highlighted the achievement of chemical analogs with high selectivity by using mild and ecofriendly conditions. Prompted by the enormous pharmacological, alimentary, and chemical interest in coumarin-like compounds, this study evaluated the biotransformation of nine coumarin scaffolds using Cunninghamella elegans ATCC 10028b and Aspergillus brasiliensis ATCC 16404. The chemical reactions which were catalyzed by the microorganisms were highly selective. Among the nine studied coumarins, only two of them were biotransformed. One of the coumarins, 7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, was biotransformed into the new 7,9-dihydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one, which was generated by selective hydroxylation in an unactivated carbon. Our results highlight some chemical features of coumarin cores that are important to biotransformation using filamentous fungi.

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Non-terpenoid biotransformations by Mucor species

Cited by 16 publications

References 74 publications

An Overview of Biotransformation and Toxicity of Diterpenes

An Overview of Biotransformation and Toxicity of Diterpenes

Endophytic Fungi From the Brazilian Flora and Their Employment in Biotransformation Reactions

Mapping the Biotransformation of Coumarins through Filamentous Fungi

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