Monoterpene biotransformation by Colletotrichum species

Sales, Adones; Afonso, Luana Ferreira; Americo, Juliana Alves; Rebelo, Mauro de Freitas; Pastore, Gláucia Maria; Bicas, Juliano Lemos

doi:10.1007/s10529-017-2503-2

Cited by 27 publications

(14 citation statements)

References 15 publications

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“…Remarkably, the antifungal activity of these essential oils and their main volatiles was less effective than that of L. virginicum and phenylacetonitrile. Other studies revealed that isolates of Colletotrichum acutatum are able to transform limonene and linalool into limonene‐1,2‐diol, and linalool oxides, respectively [17] . This data and the MIC obtained in this work for both monoterpenes, suggest that C. acutatum is resistant to limonene and linalool.…”

Section: Resultssupporting

confidence: 75%

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum)

Pacheco‐Hernández

Santamaría-Juárez

Hernández-Silva

et al. 2021

Chemistry & Biodiversity

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The essential oil from the annual plant Lepidium virginicum L. was chemically characterized in three consecutive years (2018–2020). The essential oils were evaluated in vitro and in situ on the causal agent of anthracnose in tamarillo fruits (Solanum betaceum). The main volatile constituents were phenylacetonitrile (>60 %), linalool (>10 %), limonene (>7 %) and α‐terpineol (>5 %). The essential oil (MIC, 19–30 μg mL−1), phenylacetonitrile (MIC, 45 μg mL−1) and α‐terpineol (MIC, 73 μg mL−1) caused a significant inhibition in the conidial viability from a wild strain of Colletotrichum acutatum, which was isolated and identified as a causal agent of anthracnose. The inoculation of conidia from C. acutatum in non‐symptomatic tamarillo fruits, followed by the in situ treatment with different concentrations of the essential oil (>30 μg mL−1), phenylacetonitrile and α‐terpineol, significantly (p<0.01) avoided the degradation of anthocyanins (delphinidin 3‐O‐rutinoside, cyanidin 3‐O‐rutinoside and pelargonidin 3‐O‐rutinoside) and carotenoids (β‐cryptoxanthin and β‐carotene) as well as retarded yellowing and necrosis triggered by anthracnose at least for 10 days. Our results suggest the potential use of the essential oil from L. virginicum as a natural component to preserve the nutraceutical content of tamarillo fruits against C. acutatum infection.

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Section: Resultssupporting

confidence: 75%

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum)

Pacheco‐Hernández

Santamaría-Juárez

Hernández-Silva

et al. 2021

Chemistry & Biodiversity

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“…On the other hand, a similar pro le was observed when (S)-(-)-limonene was applied as substrate and C. acutatum and C. nymphaeae were used as biocatalysts. Higher amounts of limonene-1,2-diol were produced (3.08 g/L -1 and 0.06 g/L -1 , respectively), which were accumulated after 192 h (Sales et al 2018b).…”

Section: Fungal Biotransformation Of Limonene For the Production Of Aroma Compoundsmentioning

confidence: 96%

“…Limonene-1,2-diol has been associated with a signi cant inhibitory effect on the pro-in ammatory activities of CD4 + and CD8 + T lymphocytes; a potential anticancer activity. It also has insect-attractant properties besides being used as avoring for beverages, chewing gum, gelatins, and puddings (Molina et al 2015b;Sales et al 2018b;Sales 2019c).…”

Section: Fungal Biotransformation Of Limonene For the Production Of Aroma Compoundsmentioning

confidence: 99%

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

Sevalho

Paulino

Souza

et al. 2021

Preprint

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The number of aroma compounds obtained by biotechnological process has increased tremendously in recent years and, as a result, are now being extensively employed in order to make products more attractive for consumers. In the present review, we inten to assess the wide range of reactions are catalyzed by fungal strains in regards to biotransformation of limonene and pinene for the aroma compounds production, their production rates/maximum concentrations and their biological potential. We comprehensively summarized in this review available data (2000–2021) regarding fungal biotransformation of limonene and pinene as biotechnological processes. Over the past years, has been paid to the biotransformation processes due to mild and environmentally friendly conditions applied. This review has shown that reports on the application of the fungi as a promising source of biocatalysts, mainly for stereoselective reactions such as hydroxylation and epoxidation. Studies have demonstrated the existence of promising monoterpenes used as substrates, which could be important from an industrial standpoint since this increases their importance as starting materials for obtaining aromatic molecules new. Moreover, biological (e.g.,antioxidant, anticancer) activities attributed to some monoterpene biotransformation products are increasingly being reported, indicating that their applications may transcend food, cosmetic and pharmaceutical industry.

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“…Limonene isomers are the most abundant monoterpene hydrocarbons found in nature. (+)-(R)-limonene is the major constituent of the essential oil obtained from citrus peels [83]. A 50-year literature review shows that the biotransformation of limonene by different types of microorganisms (bacteria, filamentous fungi, and yeasts) produces carveol, carvone, perillyl alcohol, isopiperitenol, α-terpineol, and limonene 1,2-diol [83][84][85] as main components.…”

Section: Terpenesmentioning

confidence: 99%

“…(+)-(R)-limonene is the major constituent of the essential oil obtained from citrus peels [83]. A 50-year literature review shows that the biotransformation of limonene by different types of microorganisms (bacteria, filamentous fungi, and yeasts) produces carveol, carvone, perillyl alcohol, isopiperitenol, α-terpineol, and limonene 1,2-diol [83][84][85] as main components. The biotransformation products of limonene generated by bacteria are mainly perillaldehyde, perillic acid, limonene-1,2-epoxide, and limonene-8,9-epoxide, while isopiperitenone, limonene-4-ol, and cis/trans-mentha-2,8-dienol are commonly generated by filamentous fungi and yeasts.…”

Section: Terpenesmentioning

confidence: 99%

Fermentation as an Alternative Process for the Development of Bioinsecticides

et al. 2020

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Currently, insect pest control is carried out through the application of synthetic insecticides which have been related to harmful effects on both human and environmental health, as well as to the development of resistant pest populations. In this context, the development of new and natural insecticides is necessary. Agricultural and forestry waste or by-products are very low-cost substrates that can be converted by microorganisms into useful value-added bioactive products through fermentation processes. In this review we discuss recent discoveries of compounds obtained from fermented substrates along with their insecticidal, antifeedant, and repellent activities. Fermentation products obtained from agricultural and forestry waste are described in detail. The fermentation of the pure secondary metabolite such as terpenes and phenols is also included.

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Monoterpene biotransformation by Colletotrichum species

Abstract: This is the first report on the biotransformation of these terpenes by Colletotrichum spp. and the biotransformation of limonene to limonene-1,2-diol possibly involves enzymes similar to those found in Grosmannia clavigera.

Cited by 27 publications

References 15 publications

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum)

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum)

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

Fermentation as an Alternative Process for the Development of Bioinsecticides

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