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Redalyc.Microorganisms Screening for Limonene Oxidation Ciência e Tecnologia de Alimentos ISSN: 0101-2061 [email protected] Sociedade Brasileira de Ciência e Tecnologia de Alimentos Brasil LERIN, Lindomar; TONIAZZO, Geciane; de OLIVEIRA, Débora; ROTTAVA, Leda; DARIVA, Cláudio; CANSIAN, Rogério Luis; TREICHEL, Helen; PADILHA, Francine; Ceva ANTUNES, Octávio Augusto Microorganisms screening for limonene oxidation Ciência e Tecnologia de Alimentos, vol. 30, núm. 2, abril-junio, 2010, pp. 399-405 Sociedade Brasileira de Ciência e Tecnologia de Alimentos Campinas, Brasil Available in: http://www.redalyc.org/articulo.oa?id=395940100017 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Ciência e Tecnologia de Alimentos ISSN 0101-2061 Microorganisms screening for limonene oxidation Seleção de microrganismos para oxidação de limoneno Original Lindomar LERIN1, Geciane TONIAZZO2, Débora de OLIVEIRA2*, Leda ROTTAVA1, Cláudio DARIVA3, Rogério Luis CANSIAN2, Helen TREICHEL2, Francine PADILHA3, Octávio Augusto Ceva ANTUNES1 Abstract Limonene is a monoterpene obtained in large amounts from essential oils and is used as a raw material for the synthesis of flavors and fine chemicals. Several pathways or routes for the microbial degradation of limonene making use of the cytochrome P450-dependent monooxygenases have been described. In this study, we present a fermentative screening of microorganisms in order to verify their ability to perform the desirable conversion. In parallel, the PCR technique was used to select the microorganisms that contain the limC gene, which is responsible for the conversion of carveol to carvone. The microorganisms selected by PCR were not able to bioconvert limonene. From this result, we can suppose that these strains do not have the gene that codifies the enzyme responsible for the transformation of limonene into carveol. The results obtained in the fermentative screening showed that 4 microorganisms were able to bioconvert limonene into carveol. In addition, the amplification results showed the presence of fragments of 800 pb, expected for the limC gene. Therefore, the results obtained in the bioconversion and evaluation of the limC gene did not allow a correlation showing that these strains do not contain all the enzymes responsible for the conversion of limonene to carvone. Keywords: CDH (carveol dependent dehydrogenase); carveol; carvone; PCR; fermentative screening. Resumo O limoneno é um monoterpeno obtido em grandes quantidades a partir de óleos essenciais, podendo ser utilizado como matéria- prima na síntese de flavours e compostos para química fina. Várias rotas para a degradação microbiológica do limoneno fazendo uso da monoxigenase dependente do citocromo P450 têm sido propostas. Neste trabalho, são apresentados dados obtidos no screening fermentativo de microrganismos visando verificar suas habilidades em realizar a conversão desejada. Em paralelo, a técnica do PCR foi também utilizada visando selecionar microrganismos que apresentam o gene limC, responsável pela conversão de carveol a carvona. Os microrganismos selecionados por PCR não foram capazes de bioconverter o limoneno. A partir dos resultados obtidos pode-se supor que estas cepas não possuem o gene que codifica a enzima responsável pela etapa de transformação do limoneno a carveol. Os resultados obtidos no screening fermentativo mostraram que 4 microrganismos foram capazes de bioconverter o limoneno. Além disso, o resultado da amplificação mostrou a presença de fragmentos de 800 pb, esperados para o gene limC. Desta forma, os resultados obtidos na bioconversão e avaliação do gene limC gene não permitiram obter uma correlação, mostrando que as cepas testadas não possuem todas as enzimas responsáveis pelas etapas de conversão do limoneno a carvona. Palavras-chave: CDH (dehidrogenase dependente do carveol); carveol; carvona; PCR; screening. 1 Introduction The essential oils are a source of volatile terpenes, (-)-4S-limonene, is hydroxylated exclusively at C3 position substances widely distributed in nature. Spearmint (Mentha producing (-)-trans-isopiperitenol, which is subsequently spicata) and peppermint (Mentha piperita) are species used converted into a complex mixture of compounds of peppermint for the commercial production of essential oils. Their distinct oil. In spearmint, the limonene is hydroxylated exclusively at characteristics are based on the oxygenation position of the C6 position producing (-)-trans-carveol and, following the constituent monoterpenoid ρ-mentane. Peppermint produces oxidation, (-)-carvone. This region-specific hydroxylation almost exclusive monoterpenes with oxygen C3 position (such is mediated by two cytochrome P450 enzymes, limonene- as (-)-menthol, which is responsible for the cold sensation of 6-hydroxylase (CYP71D18) and limonene-3-hydroxylase the peppermint). The spearmint produces a monoterpene with (CYP71D13) (SCHALK; CROTEAU, 2000). oxygen at the C6 allylic position (such as (-)-carvone, which is responsible for the typical note of the spearmint) (LAWRENCE, Kubota et al. (2005) showed that the cytochrome P450 1981). The precursor olefin of the bioconversion reaction, (CYP153A), heme alkane hydroxylase, from Alcanivorax sp. Recebido para publicação em 16/4/2008 Aceito para publicação em 4/1/2009 (003440) 1 Departamento de Bioquímica, Instituto de Química, Universidade Federal do Rio de Janeiro – UFRJ, CEP 21949-900, Cidade Universitária, Rio de Janeiro - RJ, Brasil 2 Departamento de Engenharia de Alimentos, Universidade Regional Integrada – URI, Campus de Erechim, CEP 99700-000, Av. Sete de Setembro, 1621, Erechim, RS, Brasil, E-mail: [email protected] 3 Instituto de Pesquisa e Tecnologia, Universidade Tiradentes – UNIT, CEP 49032-490, Campus Farolândia, Av. Murilo Dantas, 300, Aracaju - SE, Brasil *A quem a correspondência deve ser enviada Ciênc. Tecnol. Aliment., Campinas, 30(2): 399-405, abr.-jun. 2010 399 Screening for limonene oxidation mediates the oxidation reactions of various hydrocarbons, used to select the microorganisms that contain the limC gene, including not only n-alkanes but also a cycle-alkane and aromatic responsible for the conversion of carveol to carvone. hydrocarbons. This P450 gene was also used as a scaffold in the study in order to build the 5’- and 3’-arm segments for cassette 2 Materials and methods Polymerase Chain Reaction (PCR) for expressing functionally new P450 genes isolated from various environments. Escherichia 2.1 Cell production coli cells expressing these self-sufficient P450 chimerical genes able to convert n-alkanes, cycle-hexane, 1-octene, n-butyl- A total of 17 microorganisms were used in this study. benzene, and 4-phenyl-1-butene to 1-alkanols, cycle-hexanol, The strains of microorganisms belonging to different genera 1,2-epoxyoctane, 1-pheny-4-butanol, and 2-phenethyl-oxirane, were obtained from different institutions, as shown in Table 1. respectively. Many studies have been carried out about the All the strains were generously supplied by those respective oxygenases cytochrome P450 SINCE these enzymes play an institutions. Table 1 also presents the culture medium used for important role in the metabolism of the terpenoids mould and each microorganism. Fungi were cultivated in PD, YM, Malt, stabilize the oxygenation of many types of carbon skeleton, and Czapek Dox at 25 °C for 72 hour; except for Paecilomyces These enzymes begin the subsequent redox transformation and variotii that was cultivated for 120 hours. Yeasts were cultivated reactions of the conjugated that contribute significantly for the in YM at 25 °C for 24 hours and the bacteria were cultivated structural diversity and the great number of natural products in LB at 28 °C for 24 hours. Stock cultures of organisms were derivative of this class (LUPIEN et al., 1999). maintained in medium slants and stored at 4 °C after growth. Cytochrome P450-dependent hydroxylases play a pivotal role in the biosynthesis of several hundred naturally occurring 2.2 Screening experiments oxygenated monoterpenes (e.g., menthol, carvone, thujone, pinocamphone), which are largely responsible for the flavor For the biotransformation experiments, the reactions were and fragrance of plant-derived essential oils (BAUER; GARBE; started 3 days after inoculation for the fungi and 24 hours for SURBURG, 1990). Most oxygenated monoterpenes are formed bacteria and yeasts by adding 300 µL of the substrate directly by the initial cyclization of the precursor geranyl-diphosphate to the culture flasks with 30 mL of medium. The substrates to an olefin that defines the structural family of the metabolites were added as solutions in absolute ethanol (1:1 v/v). It was produced, followed by the regio- and stereoespecifc cytochrome used 1% (v/v) of substrate in 1% (v/v) of EtOH, at 25 °C and P450–dependent allylic hydroxylation of the parent olefin, 150 rpm for 6 days in all experiments. The media and cultivation which determines the oxygenation pattern of the derived time used for each microorganism are presented in Table 1. metabolites (KARP; CROTEAU, 1988). All experiments were carried out in parallel with controls and under the same experimental conditions without the presence Several pathways for the microbial degradation of limonene of microorganism. The experiments (duplicate runs were have been described so far, but most of them have not been conducted
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