Comparative study of the bioconversion process using R-(+)- and S-(–)-limonene as substrates for Fusarium oxysporum 152B

Bution, Murillo Lino; Bicas, Juliano Lemos; Dolder, Mary Anne Heidi; Pastore, Gláucia Maria

doi:10.1016/j.foodchem.2014.11.059

Cited by 38 publications

(28 citation statements)

References 34 publications

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“…However, during co-cultivation on split-plates, the headspace concentration of nearly all compounds was already lower very early at day 3 and 7 compared to the concentration found in solitary cultures of A. alternata . Because border effects were similar for both setups during this early stage, an active/passive adsorption of compounds in F. oxysporum mycelia is probable, especially because strains of F. oxysporum can transform terpenes 39 40 and various fungi are known to grow with terpenes or similar compounds as a sole carbon source 41 . Another possibility is the reduced production of sesquiterpenes by A. alternata after recognition of F. oxysporum volatiles (i.e., δ-elemene).…”

Section: Discussionmentioning

confidence: 94%

Sesquiterpene emissions from Alternaria alternata and Fusarium oxysporum: Effects of age, nutrient availability and co-cultivation

Weikl

Ghirardo

Schnitzler

et al. 2016

Sci Rep

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Alternaria alternata is one of the most studied fungi to date because of its impact on human life – from plant pathogenicity to allergenicity. However, its sesquiterpene emissions have not been systematically explored. Alternaria regularly co-occurs with Fusarium fungi, which are common plant pathogens, on withering plants. We analyzed the diversity and determined the absolute quantities of volatile organic compounds (VOCs) in the headspace above mycelial cultures of A. alternata and Fusarium oxysporum under different conditions (nutrient rich and poor, single cultures and co-cultivation) and at different mycelial ages. Using stir bar sorptive extraction and gas chromatography–mass spectrometry, we observed A. alternata to strongly emit sesquiterpenes, particularly during the early growth stages, while emissions from F. oxysporum consistently remained comparatively low. The emission profile characterizing A. alternata comprised over 20 sesquiterpenes with few effects from nutrient quality and age on the overall emission profile. Co-cultivation with F. oxysporum resulted in reduced amounts of VOCs emitted from A. alternata although its profile remained similar. Both fungi showed distinct emission profiles, rendering them suitable biomarkers for growth-detection of their phylotype in ambient air. The study highlights the importance of thorough and quantitative evaluations of fungal emissions of volatile infochemicals such as sesquiterpenes.

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Section: Discussionmentioning

confidence: 94%

Sesquiterpene emissions from Alternaria alternata and Fusarium oxysporum: Effects of age, nutrient availability and co-cultivation

Weikl

Ghirardo

Schnitzler

et al. 2016

Sci Rep

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“…In the case of ( S )-(−)-limonene, the 1,2 double bond is epoxidized and the oxirane ring is opened to form the diol by an oxidation process leading to energy production. ( R )-(+)-Limonene is converted to α-terpineol, in a process independent of oxygen, which can be seen as a process of medium detoxification [ 29 ]. Scheme 1 and Scheme 2 , Table 1 .…”

Section: Limonenementioning

confidence: 99%

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

et al. 2020

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The main objective of this article was to present the possibilities of using the enzymatic system of microorganisms and insects to transform small molecules, such as monoterpenes. The most important advantage of this type of reaction is the possibility of obtaining derivatives that are not possible to obtain with standard methods of organic synthesis or are very expensive to obtain. The interest of industrial centers focuses mainly on obtaining particles of high optical purity, which have the desired biological properties. The cost of obtaining such a compound and the elimination of toxic or undesirable chemical waste is important. Enzymatic reactions based on enzymes alone or whole microorganisms enable obtaining products with a specific structure and purity in accordance with the rules of Green Chemistry.

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“…130 g L −1 of product after 96 h of biotransformation (Bicas et al 2010b; Resch and Hanefeld 2015). Additionally, several studies on the oxygen-independent biotransformation of limonene by F. oxysporum indicated stereoselective formation of α-terpineol by a hydratase (Maróstica and Pastore 2006; Bicas et al 2010a; Molina et al 2015). Both limonene isomers were converted; but the activity for (4 R )-(+)-limonene was 10-fold higher than for the S -enantiomer.…”

Section: Enzymes For Hydration and Their Propertiesmentioning

confidence: 99%

On the current role of hydratases in biocatalysis

Engleder

Pichler

2018

Appl Microbiol Biotechnol

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Water addition to carbon-carbon double bonds provides access to value-added products from inexpensive organic feedstock. This interesting but relatively little-studied reaction is catalysed by hydratases in a highly regio- and enantiospecific fashion with excellent atom economy. Considering that asymmetric hydration of (non-activated) carbon-carbon double bonds is virtually impossible with current organic chemistry, enzymatic hydration reactions are highly attractive for industrial applications. Hydratases have been known for several decades but their biocatalytic potential has only been explored over the past 15 years. As a result, a considerable amount of information on this enzyme group has become available, enabling their development for practical applications. This review focuses on hydratases catalysing water addition to non-activated carbon-carbon double bonds, and examines hydratases from a biochemical, structural and mechanistic angle. Current challenges and opportunities in hydration biocatalysis are discussed, and, ultimately, their potential for organic synthesis is highlighted.

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Comparative study of the bioconversion process using R-(+)- and S-(–)-limonene as substrates for Fusarium oxysporum 152B

Cited by 38 publications

References 34 publications

Sesquiterpene emissions from Alternaria alternata and Fusarium oxysporum: Effects of age, nutrient availability and co-cultivation

Sesquiterpene emissions from Alternaria alternata and Fusarium oxysporum: Effects of age, nutrient availability and co-cultivation

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

On the current role of hydratases in biocatalysis

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