Biotransformation of agallochaexcoerin A by<i>Aspergillus flavus</i>

Sura, Madhu Babu; Ankireddy, Madhu; Ponnapalli, Mangala Gowri

doi:10.1080/14786419.2014.989845

Cited by 9 publications

(10 citation statements)

References 9 publications

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“…1). This result is the first report of A. flavus-a fungal strain with probed capability to biotransfom natural products [29,30]-catalyzing an oxidative decarboxylation reaction, which is in agreement with early studies made by Buswell et al for several lignin-degrading white-rot and brown-rot fungi [31,32]. Since A. flavus transformed 4a with growing cultures but not with resting cells, it could be assumed that the oxidative decarboxylation pathway is triggered only under primary metabolism conditions.…”

Section: Microbial Screeningsupporting

confidence: 91%

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Palazzolo

Mascotti

Lewkowicz

et al. 2015

Journal of Industrial Microbiology and Biotechnology

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Aromatic carboxylic acids are readily obtained from lignin in biomass processing facilities. However, efficient technologies for lignin valorization are missing. In this work, a microbial screening was conducted to find versatile biocatalysts capable of transforming several benzoic acids structurally related to lignin, employing vanillic acid as model substrate. The wild-type Aspergillus flavus growing cells exhibited exquisite selectivity towards the oxidative decarboxylation product, 2-methoxybenzene-1,4-diol. Interestingly, when assaying a set of structurally related substrates, the biocatalyst displayed the oxidative removal of the carboxyl moiety or its reduction to the primary alcohol whether electron withdrawing or donating groups were present in the aromatic ring, respectively. Additionally, A. flavus proved to be highly tolerant to vanillic acid increasing concentrations (up to 8 g/L), demonstrating its potential application in chemical synthesis. A. flavus growing cells were found to be efficient biotechnological tools to perform self-sufficient, structure-dependent redox reactions. To the best of our knowledge, this is the first report of a biocatalyst exhibiting opposite redox transformations of the carboxylic acid moiety in benzoic acid derivatives, namely oxidative decarboxylation and carboxyl reduction, in a structure-dependent fashion.

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Section: Microbial Screeningsupporting

confidence: 91%

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Palazzolo

Mascotti

Lewkowicz

et al. 2015

Journal of Industrial Microbiology and Biotechnology

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“…Sura et al [ 58 ] studied the biotransformation of agallochaexcoerin A (compound 12 in Figure 13 ). The incubation of 12 with the pathogenic fungus Aspergillus flavus afforded the novel agallochaexcoerin G (compound 12.1 , Figure 13 ) via microbial biodehydration.…”

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“… Biotransformation of agallochaexcoerin A ( 12 ) in agallochaexcoerin G ( 12.1 ) by Aspergillus flavus [ 58 ]. …”

Section: Figurementioning

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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“…As part of our ongoing program on the isolation − and biotransformation , of bioactive compounds, we carried out biotransformation of artemisinin ( 1 ), which afforded four metabolites. They were identified as a new 14-hydroxydeoxyartemisinin ( 2 ) and three known metabolites ( 3 – 5 , Figure ).…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, direct microbial production of 1 represents the most desirable approach for the conversion of artemisinic acid to 1. 9 As part of our ongoing program on the isolation 10−12 and biotransformation 13,14 of bioactive compounds, we carried out biotransformation of artemisinin (1), which afforded four metabolites. They were identified as a new 14-hydroxydeoxyartemisinin (2) and three known metabolites (3−5, Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by Aspergillus flavus

Ponnapalli

Sura

Sudhakar

et al. 2018

J. Agric. Food Chem.

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The biotransformation of the front-line antimalarial drug, artemisinin (1) by the filamentous fungus Aspergillus flavus MTCC-9167 was investigated. Incubation of compound 1 with A. flavus afforded a new hydroxy derivative (2) along with three known metabolites (3-5). The new compound was characterized as 14-hydroxydeoxyartemisinin (2) by extensive spectroscopic data analysis (IR, H andC NMR, HSQC, HMBC, COSY, NOESY, and HR-ESIMS). The known metabolites were identified as deoxyartemisinin (3), artemisinin G (4), and 4α-hydroxydeoxyartemisinin (5). This is the first report of hydroxylation of a secondary methyl of artemisinin at C-14 by the fungus A. flavus, which is synthetically not accessible. In addition, these compounds were evaluated for their in vitro antiplasmodial activity. Artemisinin G (4) exhibited IC values in the submicromolar range, which was better than those of the nonperoxidic metabolites.

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Biotransformation of agallochaexcoerin A byAspergillus flavus

Cited by 9 publications

References 9 publications

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

Self-sufficient redox biotransformation of lignin-related benzoic acids with Aspergillus flavus

An Overview of Biotransformation and Toxicity of Diterpenes

Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by Aspergillus flavus

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