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      Transformation of trans-Anethole using the plant pathogenic fungus Colletotrichum acutatum as biocatalyst Translated title: Transformación de trans-Anetol usando el hogo fitopatogénico Colletotrichum acutatum como biocatalizador

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          Abstract

          Microbial transformation of propenylbenzenes may offer a cleaner and cheaper alternative to natural production of flavors and fragrances. In the present study, the biotransformation of trans-anethole using cells of a Colombian strain of the fungus Colletotrichum acutatum was investigated. Initially, fungitoxicity of this compound against C. acutatum was evaluated; trans-anethole displayed a relatively weak toxiciiy against the microorganism (<70%, at 200 μg/mL and after 48 hours) and apparently a detoxification mechanism was present. Then, the microorganism was incubated with the substrate atroom conditions, using three different culture media (Czapek-Dox, Sabouraud and PDB). Results show that trans-anethole is mainly degraded through an epoxide-diol pathway (trans-anethole to anethole-epoxide, then to syn- and anti-anethole-diol, p-anisaldehyde, p-anisic acid and p-anisic alcohol). However, other minor metabolites [e.g. 3-(4-methoxyphenyl)-1-propanol, 1-(4-methoxyphenyl)-2-propanol, ethyl ester of anisic acid], possibly proceeding from other metabolic pathways were also found. Additionally, it was demonsfrated that: the concenfration of metabolic products is dependent on culture medium used, being anethole-diol the mapr product obtained in all media used. Interestingly, some of the compounds generated in the biotransformation have been utilized as flavors and fragrances. Based on the identified metabolites, a possible metabolic pathway of the biotransformation of trans-anethole by C. acutatum was proposed.

          Translated abstract

          La transformación microbiana de propenilbencenos puede ofrecer una alternativa más limpia y económica para la producción natural de aromas y fragancias. En el presente estudio se investigó la biotransformación de trans-anetol usando células de una cepa colombiana del hongo Colletotrichum acutatum. Inicialmente, se evaluó la toxicidad de este compuesto contra C. acutatum; trans-anetol exhibió una toxicidad relativamente baja contra el microorganismo (<70%, a 200 μ/mL y 48 horas) y aparentemente se presentó un mecanismo de desintoxicación. Luego, el microorganismo se incubó con el sustrato a condiciones ambientales, usando tres medios de cultivo (Czapek-Dox, Sabouraud y PDB). Los resultados muestran que trans-anetol es degradado principalmente a través de una ruta epóxido-diol (trans-anetol a anetol-epóxido, luego a syn- y anti-anetol-diol, p-anisaldehido, ácido p-anísico y alcohol p-anísico). Sin embargo, también se encontraron otros metabolitos minoritarios [por ejemplo, 3-(4-metoxifenil)-1-propanol, 1-(4-metoxifenil)-2-propanol, éster etílico del ácido anísico], posiblemente procedentes de otras rutas metabólicas. Adicionalmente, se demostró que la concentración de los productos metabólicos es dependiente del medio de cultivo usado, siendo anetol-diol el producto mayoritario obtenido en todos los medios. Interesantemente, algunos compuestos generados en la biotransformación se han utilizado como aromas y fragancias. Basados en los metabolitos identificados, se propuso una posible ruta metabólica para la biotransformación de trans-anetol por C. acutatum.

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          Production of methoxyphenol-type natural aroma chemicals by biotransformation of eugenol with a new Pseudomonas sp.

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            Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent

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              Production of natural value-added compounds: an insight into the eugenol biotransformation pathway.

              During the past few years, the production of natural value-added compounds from microbial sources has gained tremendous importance. Due to an increase in consumer demand for natural products, various food and pharmaceutical industries are continuously in search of novel metabolites obtained from microbial biotransformation. The exploitation of microbial biosynthetic pathways is both feasible and cost effective in the production of natural compounds. The environmentally compatible nature of these products is one major reason for their increasing demand. Novel approaches for natural product biogeneration will take advantage of the current studies on biotechnology, biochemical pathways and microbiology. The interest of the scientific community has shifted toward the use of microbial bioconversion for the production of valuable compounds from natural substrates. The present review focuses on eugenol biotransformation by microorganisms resulting in the formation of various value-added products such as ferulic acid, coniferyl alcohol, vanillin and vanillic acid.
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                Author and article information

                Contributors
                Role: ND
                Role: ND
                Role: ND
                Role: ND
                Role: ND
                Journal
                rmiq
                Revista mexicana de ingeniería química
                Rev. Mex. Ing. Quím
                UAM, Unidad Iztapalapa, División de Ciencias Básicas e Ingeniería
                1665-2738
                December 2015
                : 14
                : 3
                : 653-666
                Affiliations
                [1 ] Universidad Complutense de Madrid España
                [2 ] Universidad Nacional de Colombia Colombia
                [3 ] Universidad Nacional de Colombia Colombia
                Article
                S1665-27382015000300009
                2980d6d5-d40c-42ce-b441-90a4135cca71

                This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

                History
                Categories
                Chemistry, Applied
                Engineering, Chemical

                General engineering,Industrial chemistry
                fungitoxicidad,biotransformación,C. acutatum,ruta metabólica,medios de cultivo,fungitoxicity,biotransformation,metabolic pathway,culture media

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