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Revista Mexicana de Ingeniería Química ISSN: 1665-2738 [email protected] Universidad Autónoma Metropolitana Unidad Iztapalapa México Velasco-Bucheli, R.; Gil, J.H.; García, C.M.; Durango, D.L. TRANSFORMATION OF CINNAMYL ALCOHOL USING IMMOBILIZED Colletotrichum acutatum CELLS AS CATALYST Revista Mexicana de Ingeniería Química, vol. 16, núm. 1, 2017, pp. 55-65 Universidad Autónoma Metropolitana Unidad Iztapalapa Distrito Federal, México Available in: http://www.redalyc.org/articulo.oa?id=62049878007 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 Vol. 16, No. 1 (2017) 55-65 Revista Mexicana de Ingeniería Química TRANSFORMATION OF CINNAMYLCONTENIDO ALCOHOL USING IMMOBILIZED Colletotrichum acutatum CELLS AS CATALYST Volumen 8, número 3, 2009 / Volume 8, number 3, 2009 TRANSFORMACI ON´ DE ALCOHOL CINAMILICO´ EMPLEANDO COMO CATALIZADOR CELULAS´ INMOVILIZADAS DE Colletotrichum acutatum 1 ∗ 2 3 3 213 DerivationR. and Velasco-Bucheli application of the Stefan-Maxwell, J.H. Gil , C.M. equations Garc ´ıa , D.L. Durango 1Universidad Complutense de Madrid, Departamento de Bioqu´ımicay Biolog´ıaMolecular I, Facultad de Biolog´ıa,Madrid, (Desarrollo y aplicación de las ecuacionesEspa˜na. de Stefan-Maxwell) 2 Universidad Nacional Stephen deColombia-Sede Whitaker Medell´ın,Facultad de Ciencias Agrarias, Departamento de Ingenier´ıaAgr´ıcolay Alimentos, Medell´ın,Colombia. 3Universidad Nacional de Colombia-Sede Medell´ın,Facultad de Ciencias, Escuela de Qu´ımica,Grupo de Qu´ımicade los Biotecnología / BiotechnologyProductos Naturales y los Alimentos, Medell´ın,Colombia. Received June 19, 2016; Accepted December 21, 2016 245 Modelado de la biodegradación en biorreactores de lodos de hidrocarburos totales del petróleo Abstract intemperizados en suelos y sedimentos The reusability and influence of three supports (calcium alginate, chitosan and polyurethane foam) in the biotransformation of cinnamyl alcohol (Biodegradation by the spores modeling and whole of sludge cells bioreactors from the of Colombian total petroleum native hydrocarbons fungus Colletotrichum weathering in acutatumsoil was evaluated. The metabolicand sediments) products cinnamaldehyde, 3-phenylpropanal, 3-phenyl-1-propanol, 1-phenylpropane-1,3- diol, 3-hydroxy-1-phenyl-1-propanone,S.A. Medina-Moreno, S. hydrocinnamic Huerta-Ochoa, acid,C.A. 2-phenylethanol,Lucho-Constantino, 1-phenylethane-1,2-diol, L. Aguilera-Vázquez, A. Jiménez- cinnamyl acetate, cinnamic acid andGonzález 3-phenyl y M. propyl Gutiérrez-Rojas acetate were detected by GC-MS. The concentration of these products was clearly dependent on support. Thus, the bioprocesses with immobilized spores or whole cells into polyurethane foam were more 259 Crecimiento, sobrevivencia y adaptación de Bifidobacterium infantis a condiciones ácidas efficient to obtain 1-phenylpropane-1,3-diol, and allowed reusing the support at least 3 or 4 times without significant loss of activity. However, (Growth, under survival the same and adaptation conditions, of alginateBifidobacterium and chitosan infantis were to acidic inadequate conditions) supports for this purpose, and instead, 3-phenyl-1-propanolL. Mayorga-Reyes, and cinnamic P. Bustamante-Camilo, acid were the major A. Gutiérrez-Nava, metabolic compounds. E. Barranco-Florido Therefore, y the A. biotransformationAzaola- of cinnamyl alcohol using immobilized C. acutatum cells in polyurethane foam can potentially offer a simple and efficient Espinosa way to obtain 1-phenylpropane-1,3-diol. 265 Statistical approach to optimization of ethanol fermentation by Saccharomyces cerevisiae in the Keywords: phytopathogenic fungus, metabolic pathway, immobilization, reuse, 1-phenylpropane-1,3-diol. Resumen presence of Valfor® zeolite NaA Se evaluo´ la reutilizacion´ e influencia de tres soportes (alginato de calcio, quitosano, y espuma de poliuretano) en la (Optimización estadística de la fermentación etanólica de Saccharomyces cerevisiae en presencia de biotransformacion´ de alcohol cinam´ılico por esporas y celulas´ completas del hongo nativo colombiano Colletotrichum zeolita Valfor® zeolite NaA) acutatum. Se detectaron por CG-EM los productos metabolicos´ cinamaldeh´ıdo, 3-fenilpropanal, 3-fenil-1-propanol, 1- fenil-1,3-propanodiol,G. Inei-Shizukawa, 3-hidroxi-1-fenil-1-propanona, H. A. Velasco-Bedrán,acido´ G. hidrocinF. Gutiérrez-Lópezamico,´ 2-feniletanol, and H. Hernández-Sánchez 1-fenil-1,2-etanodiol, acetato de cinamilo, acido´ cinamico´ y acetato de 3-fenilpropanol. La concentracion´ de estos productos fue claramente dependiente del soporte. AsIngeniería´ı, los bioprocesos de procesos con / Process esporas engineering o celulas´ completas inmovilizadas en la espuma de poliuretano fueron mas´ eficientes para271 obtener Localización 1-fenil-1,3-propanodiol, de una planta industrial: y permitieron Revisión su crítica reutilizaci y adecuaciónon´ al menos de 3los o criterios 4 veces sinempleados perdida´ en significativa de la actividad. Sin embargo, bajo las mismas condiciones, alginato y quitosano no fueron soportes adecuados para este esta decisión proposito,´ y en su lugar, 3-fenil-1-propanol y acido´ cinamico´ fueron los compuestos metabolicos´ mayoritarios. Por lo tanto, la biotransformaci on´(Plant de alcoholsite selection: cinam Critical´ılico usando review candelulas´ adequation de C. acutatum criteria usedinmovilizadas in this decision) enespuma de poliuretano puede ofrecer potencialmenteJ.R. Medina, una v´ıa R.L. simple Romero y eficiente y G.A. Pérez para obtener 1-fenil-1,3-propanodiol. Palabras clave : hongo fitopatogeno,´ ruta metabolica,´ inmovilizacion,´ reutilizacion,´ 1-fenil-1,3-propanodiol. 1 Introduction Phytopathogen fungi of the genus Colletotrichum free whole cells of Colletotrichum acutatum as are known for their abilities to transform natural biocatalyst (Velasco et al., 2010). The substrate compounds. In a previous report, we have described was mainly converted to 3-phenyl-1-propanol (B), 3- the biotransformation of cinnamyl alcohol (A) using phenyl propyl acetate (C), hydrocinnamic acid (D), ∗ *Corresponding author. E-mail: [email protected]; Tel. +34-91-394-41-50, Fax +34-91-394-46-72 Publicado por la Academia Mexicana de Investigacion´ y Docencia en Ingenier´ıa Qu´ımica A.C. 55 Velasco-Bucheli et al./ Revista Mexicana deIngenier ´ıaQu ´ımica Vol. 16, No. 1 (2017) 55-65 2-phenylethanol (E), 1-phenyl-1,2-ethanediol (F), and Leica CME 1349521X. 1-phenylpropane-1,3-diol (G). We have also shown that the relative abundance of metabolic compounds 2.2 Biological and chemical materials was dependent not only on the biotransformation time, but also on the type of culture medium used. Dr. Afanador-Kafuri (Afanador-Kafuri et al., 2003) Interestingly, some of the metabolic compounds from kindly donated the strain of C. acutatum. The the biotransformation of cinnamyl alcohol by C. microorganism was conserved and freshly subcultured acutatum have been widely used in the food, beverage, on PDA before use. Fungal spores were stored cosmetic, chemical and pharmaceutical sector as in 20% (w/v) glycerol at -20oC. Cinnamyl alcohol flavor and fragrance (Sun et al., 2016; Tian et al., (A) of analytical grade and chitosan were purchased 2015; Velasco et al., 2015; Behan et al., 1996; Savina from Sigma-Aldrich Co. (St. Louis, MO, USA). et al., 1999; Sendovski et al., 2010). Furthermore, the Bacto Agar was obtained from Becton, Dickinson compound 1-phenylpropane-1,3-diol is an important and Co. (Franklin Lakes, NJ, USA). Calcium intermediate in the synthesis of therapeutic agents chloride dihydrate and anhydrous alpha-D(+)-glucose for the treatment of psychiatric disorders (depression, were acquired from Merck KGaA (Darmstadt, anxiety, alcoholism) and metabolic problems (obesity Germany) and Acros Organics (Fair Lawn, NJ, USA), and bulimia), such as fluoxetine and norfluoxetina respectively. Alginic acid (sodium salt) of very low (Kumar et al., 2004). Also 1-phenylpropane-1,3- viscosity was from Alfa Aesar (Ward Hill, MA, USA). diol has been suggested as starting material to obtain The polyurethane foam (PUF) employed was Scotch- tolterodine, a drug for the treatment of urinary Brite 3M. incontinence (De Castro and Rhee, 2008). Here we describe the biotransformation of cinnamyl alcohol by 2.3 Isolation of C. acutatum spores immobilized spores and whole cells of Colletotrichum acutatum, and the reusability of some supports (i:e:, Petri dishes cultivated with the fungus for 8 days calcium alginate, chitosan and polyurethane foam) on Potato Dextrose Agar (PDA) were washed with under repeated batch biotransformation conditions as distilled water (2x2 mL). The suspension was filtered well. A special attention was paid to the production of on Whatman No. 1 filter paper. Then, the filtrate was 1-phenylpropane-1,3-diol. centrifuged at 10000 rpm for 5 min and the supernatant was eliminated; this procedure was repeated two times. The spores (precipitate) were recollected, 2 Materials and methods suspended in 20% (w/v) glycerol, and stored at −20◦C until used; the colony-forming units (CFU) were 2.1 Analytical methods counted in a Neubauer chamber by microscopy after staining with lactophenol blue. The solution was Gas chromatography was developed on a homogenized at room temperature and used in the Hewlett-Packard 6890 (Agilent Technologies) gas immobilization and biotransformation
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    Proc. Natl. Acad. Sci. USA Vol. 95, pp. 12803–12808, October 1998 Biochemistry NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamyl- alcohol dehydrogenase and cinnamoyl-CoA reductase (monolignolygenetic modificationyantisense RNAyconiferyl alcoholyferuloyl-CoA) JOHN RALPH*†‡,RONALD D. HATFIELD*, JOE¨L PIQUEMAL§,NABILA YAHIAOUI§,MICHEL PEAN¶, i CATHERINE LAPIERRE , AND ALAIN M. BOUDET§ *United States Dairy Forage Research Center, United States Department of Agriculture, Agricultural Research Service, Madison, WI 53706-1108; †Department of Forestry, University of Wisconsin, Madison, WI 53706-1598; §Unite´Mixte de Recherche, Centre National de la Recherche Scientifique 5546, Centre de Biologie et Physiologie Ve´ge´tale, Universite´Paul Sabatier Baˆt.4R1, 118 route de Narbonne, F-31062 Toulouse Cedex, France; ¶Commissariat a`l’Energie Atomique, De´partementd’Ecophysiologie Ve´ge´tale et Microbiologie, Cadarache, Baˆt.177, F-13108 Saint Paul lez Durance Cedex, France; and iInstitut National de la Recherche Agronomique, Laboratoire de Chimie Biologique, F-78850 Thiverval-Grignon, France Communicated by Ron Sederoff, North Carolina State University, Raleigh, NC, July 29, 1998 (received for review May 13, 1998) OHO OS OH OH ABSTRACT Homologous antisense constructs were CoA used to down-regulate tobacco cinnamyl-alcohol dehydro- CCL' CCR' CAD' p-Coumaryl genase (CAD; EC 1.1.1.195) and cinnamoyl-CoA reductase alcohol (CCR; EC 1.2.1.44) activities in the lignin monomer biosyn- OH OH OH OH 1) HYD1' 1) HYD2' 1) HYD3' 1) HYD4' thetic pathway. CCR converts activated cinnamic acids 2) OMT1' 2) OMT2' 2) OMT3' 2) OMT4' OHO OS OH OH (hydroxycinnamoyl–SCoAs) to cinnamaldehydes; cinnama- CoA CCR CAD ldehydes are then reduced to cinnamyl alcohols by CAD.
  • Effects of Cinnamon (Cinnamomum Spp.) in Dentistry

    Effects of Cinnamon (Cinnamomum Spp.) in Dentistry

    molecules Review Effects of Cinnamon (Cinnamomum spp.) in Dentistry: A Review Spartak Yanakiev Medical College Y. Filaretova, Medical University—Sofia, Yordanka Filaretova Street 3, 1000 Sofia, Bulgaria; [email protected]fia.bg; Tel.: +35-98-8644-5108 Received: 26 July 2020; Accepted: 11 September 2020; Published: 12 September 2020 Abstract: Dental medicine is one of the fields of medicine where the most common pathologies are of bacterial and fungal origins. This review is mainly focused on the antimicrobial effects of cinnamon essential oil (EO), cinnamon extracts, and pure compounds against different oral pathogens and the oral biofilm and the possible effects on soft mouth tissue. Basic information is provided about cinnamon, as is a review of its antimicrobial properties against the most common microorganisms causing dental caries, endodontic and periodontal lesions, and candidiasis. Cinnamon EO, cinnamon extracts, and pure compounds show significant antimicrobial activities against oral pathogens and could be beneficial in caries and periodontal disease prevention, endodontics, and candidiasis treatment. Keywords: cinnamon essential oil; dentistry; oral pathogens; oral biofilm; candida; antimicrobial effect; dental caries; endopathogens; cinnamaldehyde; eugenol 1. Introduction Dental medicine is one of the fields of medicine where the most common pathologies are of bacterial and fungal origins. Widely spread diseases like dental caries, periodontal disease, and endodontic lesions are caused by well-known bacterial and fungal pathogens: Streptococcus mutans, Streptococcus salivarius, Streptococcus sanguinis, Porfiromonas gingivalis, Prevotella intermedia, Actinobacilus actinomycetemcomitans, Enterococcus faecalis, Candida albicans, etc. [1]. Preventive medicine relies mostly upon reducing the bacterial biofilm via oral hygiene. The most often used active ingredients in mouth rinses and toothpastes are chlorhexidine, hyaluronic acid, and fluorides.