ABSTRACT Isoflavonoid composition of freshly harvested soy sprouts of six cultivars grown in Colombia was analyzed. Evaluations on the effect of storage time at 12 °C and exogenous application of the elicitor 2,6-dichloro isonicotinic acid (INA) were carried out to establish their influence in the ability of soy sprouts for synthesizing isoflavonoids. In addition, elicited and non-elicited sprouts of soy cultivar Soy SK-7 was assessed for total phenolic content and antioxidant activity according to the growth stage (VE, VC, and V1) and tissues (cotyledon-epicotyl and hypocotyl-root). Isoflavonoid content and antioxidant capacity were dependent on the cultivar, growth stage, tissue, and storage time at 12 °C. Growth stages VE and V1 and the hypocotyl-root exhibited the highest total phenolic content and antioxidant activity. In general, 6”-O-malonylgenistin, daidzin and genistin were the major constituents in the cultivars. Soy SK-7 and Panorama 358 displayed the highest amounts of 6”-O-malonylgenistin (155.9 µg/g) and daidzin (83.5 µg/g), respectively. Results showed that the isoflavonoids and phenolic contents and antioxidant activity were significantly increased by application of INA. This information can be useful to produce soybean sprouts with increased amounts of bioactive compounds and improved response to abiotic and biotic stresses. analyzed 1 C 2,6dichloro 26dichloro dichloro 2,6 2 6 INA (INA addition nonelicited non SK7 SK 7 SK- VE, (VE VC V cotyledonepicotyl cotyledon epicotyl hypocotylroot. hypocotylroot hypocotyl root . hypocotyl-root) tissue general 6Omalonylgenistin, 6Omalonylgenistin Omalonylgenistin O malonylgenistin, malonylgenistin 35 155.9 1559 155 9 (155. µg/g µgg µg g 83.5 835 83 5 (83. µg/g, , respectively stresses 6dichloro 26 2, 3 155. 15 (155 83. 8 (83 (15 (8 (1 (

RESUMEN Se evaluó el efecto de extractos, el aceite esencial y los componentes principales del perejil (Petroselinum crispum (Mill.) Fuss.) contra el hongo fitopatógeno Collectotrichum acutatum mediante el método del agar envenenado. Los resultados mostraron que todos los extractos, junto con el aceite esencial, inhibieron significativamente el crecimiento radial de C. acutatum en concentraciones superiores a 100 μg mL-1. La mayor actividad se encontró para el aceite esencial, seguido por el extracto de n-hexano. El análisis por cromatografía de gases con espectroscopia de masas (CG-EM) del extracto de n-hexano y el aceite esencial de P. crispum mostró que los componentes principales corresponden a los fenilpropanoides miristicina y parsley-apiol. Ambos compuestos fueron aislaron por técnicas cromatográficas convencionales y sus estructuras elucidadas por métodos espectroscópicos. La miristicina y el parsley-apiol mostraron un efecto inhibidor significativo contra C. acutatum. La actividad fungistática más alta se encontró para parsley-apiol con un valor CI50 de 40 μg mL-1. En conclusión, el perejil puede ser una buena fuente de compuestos antimicóticos para controlar el C. acutatum.

ABSTRACT The effect of extracts, essential oil, and their major constituents from parsley (Petroselinum crispum (Mill.) Fuss.) against the phytopathogenic fungus Collectotrichum acutatum was evaluated by the poisoned agar method. Results showed that all extracts, along with the essential oil, significantly inhibit the radial growth of C. acutatum at concentrations higher than 100 μg mL-1. The higher activity was found for the essential oil followed by the n-hexane extract. Analysis by gas chromatography with mass spectroscopy (GC-MS) of n-hexane extract and the essential oil of P. crispum showed that the major components correspond to the phenylpropanoids myristicin and parsley-apiole. Both compounds were isolated by conventional chromatographic techniques and their structures elucidated by spectroscopic methods. Myristicin and parsley-apiole displayed a significant inhibitory effect against C. acutatum. The highest fungistatic activity was found to parsley-apiole with IC50 value of 40 μg mL-1. In conclusion, parsley may be a good source of antifungal compounds to control C. acutatum.

Abstract Time-course and dose-response experiments were carried out to establish the ability for synthesizing isoflavonoids of soybean seedlings (cv. Soyica P34) treated with salicylic (SA) and isonicotinic acids (INA). Then, 25 structurally-related compounds were evaluated for their isoflavonoid-eliciting activity. Next, the antimicrobial and antioxidant activities of EtOAc-soluble fraction from soybean seedlings treated with some synthetic elicitors were determined. Results showed that the concentration of isoflavonoids in soybean seedlings was significantly increased by the application of SA and INA. The major isoflavonoids detected were the malonyl-glycosidic isoflavones, followed by genistin and daidzin. The isoflavone aglycones (genistein, daidzein, and formononetin), coumestrol and glyceollins were found in lower concentrations. Maximum accumulation of glyceollins was detected after 48 and 144 h in soybean seedlings treated with 1.6 mM INA and SA, respectively. EtOAc-extracts from soybean seedlings treated with two structurally-related compounds to INA displayed a significant antimicrobial and antioxidant activity. Therefore, INA, SA and structurally-related compounds can be used to increase the amounts of natural antioxidant or antimicrobial compounds in soybean, either to protect the plant directly against pathogens or as a natural source for subsequent isolation of isoflavonoids or bioactive extracts, which have potential application in functional foods or pharmaceutical and personal care products.

El propóleo es un antimicrobiano natural que puede ser usado como bioaditivo en recubrimientos para controlar pérdidas en la calidad de frutas. Se evaluó el efecto de dos recubrimientos, control (quitosano, 1%) y tratamiento (quitosano, 1%; conteniendo extracto etanólico de propóleos, 5%), sobre las propiedades microbiológicas y fisicoquímicas de frutos de papaya. El perfil químico del propóleo reveló la presencia de ácidos grasos y sus ésteres, carbohidratos, ácidos diterpénicos, y triterpenos pentacíclicos. Los frutos recubiertos con el tratamiento mostraron un índice de deterioro y un diámetro de la infección del hongo Colletotrichum gloeosporioides inferior al de las papayas control, extendiéndose en dos días la aparición de daños. Adicionalmente, el tratamiento no afectó significativamente las propiedades fisicoquímicas de la papaya, en comparación con el control. En conclusión, el recubrimiento formulado con propóleos exhibió un efecto fungistático y bacteriostático in situ, sin alterar los cambios fisiológicos de los frutos de papaya durante el almacenamiento.

Propolis is a natural antimicrobial that can be used as a bioadditive in coatings to control fruit quality losses. The effect of two coatings was evaluated, a control (chitosan, 1%) and a treatment (chitosan, 1%; containing propolisethanolic extract, 5%), on the microbiological and physicochemical properties of papaya fruits. The chemical profile of the propolis revealed the presence of fatty acids and their esters, carbohydrates, diterpenic acids, and pentacyclic triterpenes. The fruits covered with the treatment demonstrated a reduced deterioration index and infection diameter of the fungus Colletotrichum gloeosporioides, as compared to the control papayas, postponing the appearance of damage by two days. Additionally, the treatment did not significantly affect the physicochemical properties of the papaya, as compared to the control. In conclusion, the coating formulated with propolis exhibited an in situ fungicidal and bactericidal effect without altering the physiological changes of the papaya fruit during storage.

Se realizó una comparación de las propiedades fisicoquímicas de los propóleos recolectados en los municipios de Galapa, Sabanalarga, Santo Tomás y Juan de Acosta, del departamento del Atlántico (Colombia). Adicionalmente, se estableció la actividad antioxidante in vitro de los extractos etanólicos de propóleos (EEP), mediante las técnicas de DPPH, ABTS, FRAP y ORAC. El análisis fisicoquímico de los propóleos mostró valores de 8,48 - 24,21%, 1,77 - 6,07%, 55,57 - 77,93%, 5,74 - 11,69% y 0,35 - 3,86%, para el EEP, ceras, insolubles, humedad y cenizas, respectivamente. La determinación para los fenoles totales, se encuentra entre 63,72 y 94,55mg, de ácido gálico/g de muestra. Las absorbancias específicas de los EEP estuvieron dentro del rango de 26 a 96 y el contenido de flavonoides totales mostró valores entre 1,90 y 3,36mg, de quercetina/g de muestra. De los extractos, el que presentó mayor capacidad antioxidante fue el propóleos, recolectado en el municipio de Galapa, con los siguientes valores DPPH: 190,41 TEAC (µmol/g), ABTS: 1918,41 TEAC (µmol/g) y FRAP: 321,27 AEAC (µmol/g) y el segundo valor más alto en ORAC (1964,80 µmol Trolox/g de propóleos). Los resultados obtenidos indican que los propóleos estudiados presentaron variación en las propiedades fisicoquímicas. Los valores de algunos de los parámetros fisicoquímicos estimados no cumplieron con las normativas de calidad establecidas internacionalmente; no obstante, los extractos etanólicos de propóleos evaluados presentaron un alto contenido de fenoles, los cuales, están relacionados con las propiedades antioxidantes encontradas experimentalmente.

A comparison of the physicochemical properties of the propolis collected in the Galapa, Sabanalarga, Santo Tomás and Juan de Acosta's municipalities of the Atlantic department (Colombia) was made. Additionally, the in vitros antioxidant activity of ethanol extracts of propolis (EEP) through the DPPH, ABTS, FRAP and ORAC methods was established. The physicochemical analysis of propolis indicated values between 8.48 - 24.21%, 1.77 - 6.07%, 55.57 - 77.93%, 5.74 - 11.69% and 0.35 - 3.86%, for EEP, waxes, insoluble residues, humidity and ashes respectively. The determination for the total phenolic content was between 63.72 and 94.55mg of gallic acid/g of sample. The EEP's specific absorbance ranged from 26 to 96 and the total flavonoid content showed values between 1.90 and 3.36mg of quercetin/g of sample. The extract that showed the highest antioxidant capacity was the propolis collected in the municipality of Galapa with the following values, DPPH: 190,41 TEAC (µmol/g), ABTS: 1918,41 TEAC (µmol/g), FRAP: 321,27 AEAC (µmol/g), and the second highest value in ORAC (1964,80 µmol TROLOX/g of propolis). The results obtained indicated that the propolis studied showed a variation in its physicochemical properties. Some of the estimated physicochemical parameter values did not fulfill the established international quality regulations. Nevertheless, the ethanol extracts of the evaluated propolis presented a high content of phenols, related with the antioxidant properties found experimentally.

Fungal growth in fruits may cause spoilage and result in a reduction of their quality and quantity. The aim of the current study was to investigate the antifungal activity and the metabolism of thymol and carvacrol by Colletotrichum acutatum and Botryodiplodia theobromae. The results showed that both compounds provided relatively good control against these plant pathogenic fungi. Mycelial growth of C. acutatum and B. theobromae was inhibited at 50 µg/mL and above. At 150 µg/mL, thymol and carvacrol inhibited the radial growth of fungi completely and this effect remained for 240 h. Furthermore, thymol and carvacrol were metabolized by the plant pathogenic fungi in low proportion to several compounds, including thymoquinone, thymohydroquinone, thymyl- and carvacryl acetate, thymyl- and carvacryl methyl ether. The transformations affect the structural requirements of thymol and carvacrol related to their antimicrobial activity and mode of action. The relatively high antifungal activity of thymol and carvacrol against C. acutatum and B. theobromae and the low levels of microbial transformation indicate that both compounds could be an alternative to traditional chemical fungicides for control of pre- and postharvest phytopathogenic fungi on fruits or vegetables.

El crecimiento de los hongos en frutas puede causar el deterioro de los alimentos y resultar en una reducción de la calidad y la productividad. El objetivo del presente estudio fue investigar la actividad antifúngica, y el metabolismo de timol y carvacrol por Colletotrichum acutatum y Botryodiplodia theobromae. Los resultados muestran que ambos compuestos despliegan un relativo buen control contra los hongos fitopatogénicos; el crecimiento micelial de C. acutatum y B. theobromae se inhibió a concentraciones de 50 µg/mL y mayores. A 150 µg/mL, timol y carvacrol inhibieron el crecimiento radial de los hongos completamente y este efecto permaneció durante 240 h. Además, los hongos fitopatogénicos metabolizaron timol y carvacrol a varios compuestos en una baja proporción, incluyendo timoquinona, timohidroquinona, timil- y carvacril acetato, timil- y carvacril metil eter, entre otros. Las transformaciones afectan los requerimientos estructurales del timol y carvacrol relacionados con su actividad antimicrobiana y modo de acción. La actividad antifúngica relativamente alta de timol y carvacrol contra C. acutatum and B. theobromae y los niveles de transformación microbiana bajos, indican que ambos compuestos pueden ser una alternativa a los fungicidas químicos tradicionales para el control de los hongos fitopatogénicos en pre- y poscosecha de frutas y vegetales.

En los últimos años, la agroindustria de cítricos nacional ha mostrado un dinamismo significativo, originado por la expansión del mercado de los derivados de frutas. Esta actividad ha conllevado a la generación de una gran cantidad de residuos, los cuales tienen potencialidad como material de partida para la elaboración de productos comerciales con alto valor agregado como: aceites esenciales (AE), aceites fijos y fibras entre otros. Los AE tienen una importante demanda en la industria de alimentos, farmacéutica y de cosméticos. Este trabajo describe la extracción y caracterización del AE de mandarina obtenido, mediante arrastre con vapor, a partir de desechos agroindustriales. Se evaluó el efecto de la presión de vapor, el espesor y el número de capas del material vegetal, sobre el rendimiento y calidad del AE. Las condiciones de operación fueron ajustadas de acuerdo con las características de diseño de la planta de extracción de una industria local.

In recent years, citrus national agro-industries have shown a significant momentum, led by the market expansion of fruit derivatives. This activity has resulted in the generation of large amounts of waste, which could have a potential as starting material for the development of commercial products with high added value such as essential oils (EO), fixed oils, and fibres among others. The EO have a strong demand in the food industry, pharmaceuticals, and cosmetics. This paper describes the extraction and characterization of mandarin EO obtained through steam distillation, of agro-industrial waste. The effect of vapour pressure, thickness, and the number of layers of plant material, were evaluated on the yield and quality of EO. The operating conditions were adjusted in accordance to the design characteristics of the extraction plant of a local company.

The aims of the present study were to evaluate the antifungal properties of Colombian propolis extracts against Colletotrichum gloeosporioides and Botryodiplodia theobromae, and to isolate and identify the main constituents from the active extracts. Therefore, propolis samples were thoroughly extracted with n-hexane/methanol (EPEM), dichloromethane, ethyl acetate, and methanol. Experimental results indicated that mycelial growth of all selected microorganisms was reduced in culture media containing EPEM and dichloromethane fractions. Furthermore, through antifungal bioassay-guided fractionation, three known labdane-type diterpenes: isocupressic acid (1), (+)-agathadiol (2) and epi-13-torulosol (3) were isolated as the main constituents from the active fractions.

En este estudio se evaluaron las biotransformaciones realizadas por el hongo fitopatógeno Colletotrichum acutatum, sobre los sustratos 2-feniletanol 1 y acetofenona 2; los procesos se realizaron en el medio de cultivo líquido Czapeck-Dox a temperatura promedio de 24 oC, humedad relativa entre 45 y 60%, y agitación a 150 rpm en un agitador orbital tipo shaker. En la biotransformación a partir del sustrato 1 se obtuvieron los productos metabólicos 1-fenil-1,2-etanodiol 3, (2-metoxietil) benceno 4 y acetato de 2-feniletilo 5, y desde el sustrato 2 los compuestos 1-fenil-1,2-etanodiol 3, 1-feniletanol 6 y 2-feniletanol 1. Los productos de la transformación microbiana se identificaron mediante cromatografía de gases acoplada a espectrometría de masas (CG-EM), y resonancia magnética nuclear de protón y carbono (RMN 1H y 13C). Se observó una tendencia marcada del patógeno a producir hidroxilaciones sobre el sustituyente del anillo aromático; igualmente, tiene la capacidad de reducir el grupo carbonilo y esterificar los grupos hidroxilo de alcoholes primarios. Se discute una posible ruta metabólica para la transformación de los sustratos.

The microbial transformation of 2-phenilethanol 1 and acetophenone 2 was investigated using the plant pathogenic fungus Colletotrichum acutatum; the process was carried out in liquid media culture Czapeck-Dox at an average temperature of 24 oC, a relative humidity between 45% and 60% and with agitation in a shaker at 150 rpm. The biotransformation of the substrate 1 produced the metabolic products 1-phenyl-1,2-ethanediol 3, (2- methoxyethyl)benzen 4 and 2-phenylethyl acetate 5, and from substrate 2 were obtained the compounds 1-phenyl- 1,2-ethanediol 3, 1-phenylethanol 6 and 2-phenylethanol 1. The structures of metabolic products were determined by gas chromatography coupled with mass spectrometry (GC-MS) and nuclear magnetic resonance of proton and of carbon (1H and 13C NMR). The process has a strong tendency of the pathogen to produce hydroxylations on the substituents attached to the aromatic ring. Additionally, C. acutatum was effective to reduce the carbonyl group and produce esterification reactions in the hydroxyl groups from primary alcohols. The metabolic pathway of both substrates is discussed.

Neste estudo foi analisada as biotransformaçoes feitas pelo fungos fitopatogênico Colletotrichum acutatum, nos substratos 2-feniletanol 1 e acetofenona 2; os processos forem feitos no meio de cultura Czapeck-Dox a uma temperatura média de 24 °C, umidade relativa entre 45 e 60% e agitação 150 rpm em um agitador orbital tipo shaker. Na biotransformaçao do substrato 1 é obtido os produtos metabólicos 1-fenil-1,2-etanodiol 3, (2-metoxietil) benceno 4 e acetato de 2-feniletilo 5, e do substrato 2 os compostos 1-fenil- 1,2-etanodiol 3, 1-feniletanol 6 e 2- feniletanol 1. Os produtos da transformação microbial forem identificados por meio do cromatografia de gás acoplada ao espectrometria da massas (CG-EM) e ressonância magnética nuclear de hidrogênio e de carbono (RMN 1H e 13C). Uma tendência marcada do patógeno é observada para produzir hidroxilaçoes na cadeia lateral do anel aromático; também tem a capacidade de reduzir ao grupo carbonilo e esterificar dos grupos hidroxilo da função álcool primária. Uma rota metabólica possível para a transformação das substratos é discutida.

Se evaluaron las propiedades del color y la estabilidad a diferentes factores (temperatura y pH) de soluciones de los antranoides prenilados ferruginina A (FRA) y ?-hidroxiferruginina A (HFA), obtenidos a partir de las bayas de las especies Vismia guianensis y V. baccifera ssp. ferruginea. El estudio de la influencia de la temperatura sobre las características espectrales reveló que las soluciones en propilenglicol de la FRA y la HFA son relativamente estables al calor a las temperaturas de 50 y 80 °C , mientras que a 100 y 150 °C presentaron cambios ligeros en la intensidad (e) y tonalidad (?vis-max, coordenadas colorimétricas CIE L* a* b*). Adicionalmente, las variaciones del color (?vis-max, e) para los antranoides en el rango de pH 1,0-11,0 durante 60 días de almacenamiento a 4 y 25 °C , demostraron una mayor estabilidad del color en condiciones de refrigeración y pH 6,0 y 8,0, la cual fue superior para las soluciones de HFA. Las buenas características de los compuestos los hacen potencialmente útiles como colorantes naturales en la industria de los cosméticos, textil y farmacológica.

Colour properties and stability to different factors (temperature and pH) of solutions of prenylated anthranoids ferruginin A (FRA) and ? -hydroxyferruginin A (HFA), obtained from berries of Vismia guianensis and V. baccifera ssp. ferruginea, were evaluated. Spectral characteristics influenced by different temperatures, revealed that the solutions in propylenglycol of the FRA and HFA were relatively stable to the heat to temperatures of the 50 and 80 °C , whereas to temperatures of 100 and 150 °C they displayed slight changes in the intensity ( e ) and tonality ( ? vis-max, colorimetric co-ordinates in the CIE L* a* b* scale). Additionally, colour variation ( ? vis-max, e ) for both anthranoids in the pH range 1.0 - 11.0 during a period of 60 days storage at 4 and 25 °C , showed higher colour stability in refrigerated conditions and pH values of 6.0 and 8.0, being better for solutions of HFA. The good characteristics of compounds make them potentially useful like natural colourants in the textile, cosmetic and pharmacological industry.

Foram avaliadas as propriedades da cor e a estabilidade de fatores diferentes (temperatura e pH) de soluções dos antranoides prenilados ferruginina A (FRA) e ? -hidroxiferruginina A (HFA), obtidos das bagas das espécies Vismia guianensis e V. baccifera ssp. ferruginea. O estudo da influência da temperatura nas características espectrais mostra que as soluções em etilenglicol da FRA e a HFA foram relativamente estáveis ao calor para as temperaturas de 50 e 80 °C , enquanto para temperaturas de 100 e 150 °C apresentaram mudanças leves na intensidade ( e ) e tonalidade ( ? vis-max, coordenadas CIE L* a* b*). Além do mais, as variações da cor ( ? vis-max, e ) dos antranoides no rango de pH 1,0-11,0 durante 60 dias de armazenamento a 4 e 25 °C mostraram uma estabilidade maior em condições refrigerasão e em valores de pH de 6,0 e de 8,0, sendo melhor para soluções do HFA. As características boas dos compostos os fazem potencialmente úteis como corantes naturais nas indústrias das cosméticas, têxtil e farmacêutica.