Antifungal compounds in Prosopis ruscifolia: Analysis and identificationof its use to control toxigenic species of Aspergillus

Se requieren nuevos agentes antifúngicos capaces de controlar a los hongos del género Aspergillus que provocan pudriciones en maíz especialmente en los granos almacenados, contaminándolos con aflatoxinas. La ingestión de estas micotoxinas puede ocasionar intoxicaciones en humanos y animales. El control químico de especies de Aspergillus se restringe al uso de preservantes de grado limenticio, los cuales son fungistáticos, pueden alterar las características organolépticas del grano y en dosis subinhibitorias del crecimiento micelial pueden estimular a producción de aflatoxinas. Plantas autóctonas del Noroeste de Argentina (NOA) conocidas popularmente por sus propiedades antisépticas podrían proveer metabolitos secundarios capaces de detener el progreso de estos hongos. El objetivo de este trabajo fue determinar la actividad antifúngica de extractos de vinal (Prosopis ruscifolia) sobre especies de Aspergillus e identificar los metabolitos responsables. Partes aéreas de P. ruscifolia se extrajeron secuencialmente con hexano, diclorometano, acetato de etilo y metanol. La actividad antifúngica de estos extractos se ensayó sobre seis cepas de Aspergillus por bioautografía de siembra puntual y por microdilución, loque permitió determinar que solo el extracto metanólico (fMeOH) presentó actividad antifúngica sobre las especies de Aspergillus ensayadas. Las dosis mínimas inhibitorias del crecimiento fúngico (DIM) fueron de 50-200 µg/ml y las concentraciones inhibitorias del 50 % y 100 % del crecimiento fúngico (CI50 y CIM) fueron 60-297 µg/ml y 50-1500 µg/ml respectivamente. Los constituyentes del fMeOH se separaron mediante cromatografía en columna de sílica gel y por cromatografía preparativa en capa fina. Las moléculas antifúngicas se estudiaron mediante revelados específicos en cromatografía en capa fina y por espectrometría de resonancia magnética nuclear (RMN), identificándose los compuestos como alcaloides (juliflorina y juliprosineno), un ciclitol (pinitol) y una saponina triterpénica. El fMeOH de parte aéreas de P. ruscifolia no manifestó toxicidad sobre Artemia salina (CL5O > 1000 ppm), lo cual indica que el extracto no presenta citotoxicidad en eucariontes.New antifungals are needed to control Aspergillus which contaminates stored maize grains with aflatoxins toxic for humans and animals. Food additives are applied against the Aspergillus species. Nevertheless, they fungistatic, can change grain organoleptic properties and can stimulate aflatoxin production at sub-inhibitory levels. Native plants used in popular medicine as antiseptics could provide antimicrobials useful in the control of Aspergillus. The aim of this work was to determine the antifungal activity of extracts from “vinal” (Prosopis ruscifolia) against Aspergillus species and to identify its antifungal metabolites. Aerial parts of P. ruscifolia were sequentially extracted with hexane, dichloromethane, ethyl acetate and methanol. Antifungal activity of these extracts was tested against six strains of Aspergillus by dot blot bioautography and the mi-crodilution method. These data were used to calculate the minimum inhibitory dose of fungal growth (MID) 38Gómez y col.are fungistatic, can change grain organoleptic properties and can stimulate aflatoxin production at sub-inhibi-tory levels. Native plants used in popular medicine as antiseptics could provide antimicrobials useful in the control of Aspergillus. The aim of this work was to determine the antifungal activity of extracts from “vinal” (Prosopis ruscifolia) against Aspergillus species and to identify its antifungal metabolites. Aerial parts of P. ruscifolia were sequentially extracted with hexane, dichloromethane, ethyl acetate and methanol. Antifungal activity of these extracts was tested against six strains of Aspergillus by dot blot bioautography and the mi-crodilution method. These data were used to calculate the minimum inhibitory dose of fungal growth (MID) and the concentrations required to inhibit 50 % (IC50) and 100 % (MIC) of the fungal growth. Constituents of the bioactive extract was separated by column chromatography and preparative thin layer chromatography (PTLC) in silica gel. Antifungal molecules were preliminarily identified by TLC and subsequently by nuclear magnetic resonance (NMR) spectroscopy. Only the methanolic extract showed antifungal activity against Aspergillus strains (IC50 of 60-297 micrograms per mililiter. Antifungal components were identified as alkaloids (juliflorine and prosoflorine), cyclitol (pinitol) and triterpene saponins.Fil: Gomez, Analía de los Ángeles. Universidad Nacional de Tucumán; ArgentinaFil: Sampietro, Diego Alejandro. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Mandova, Tsvetelina. Universidad Paris Descartes; FranciaFil: Grougnet, Raphael. Universidad Paris Descartes; FranciaFil: Kritsanida, Marina. Universidad Paris Descartes; FranciaFil: Vattuone, Marta Amelia. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentin

Antifungal activity of Bignoniaceae plants on Aspergillus carbonarius and Aspergillus niger

Twenty four extracts from Bignoniaceae plants of northwest Argentina were tested for antifungal activity against Aspergillus species responsible of the grape black rot. Stems and leaves of Amphilophium cynanchoides, Macfadyena cynanchoides, Tecoma stans and Jacaranda mimosifolia were separately extracted with solvents of increasing polarity to obtain the dichloromethane (fCH2Cl2), ethyl acetate (fEtOAc) and methanol extracts (fMeOH). The fCH2Cl2 from stem of M. cynanchoides had the lowest IC50 (1.0-1.2 mg/mL) and MID values (0.6-1.2 mg) and the highest ID values (5.0-6.8 mm) on A. niger and A. carbonarius. The main contributors of the antifungal activity of fCH2Cl2 were identified as lapachol (MIC = 0.25-1.00 mg/ml) and 1-hydroxy-4-methylanthraquinone (MIC = 0.0625-0.125 mg/mL). These compounds synergized the antifungal activity of sodium metabisulfite and showed an additive effect in mixtures with propiconazol. They might be used as additives of commercial antifungals to protect grapes against A. niger and A. carbonarius.Fil: Apud, Gisselle Raquel. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Universidad San Pablo Tucumán; ArgentinaFil: Aredes Fernández, Pedro Adrián. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet Noa Sur. Instituto Superior de Investigaciones Biologicas. Grupo de Investigacion y Desarrollo del Noroeste Argentino | Universidad Nacional de Tucuman. Instituto Superior de Investigaciones Biologicas. Grupo de Investigacion y Desarrollo del Noroeste Argentino.; ArgentinaFil: Kritsanida, Marina. Universite de Paris, Descartes; FranciaFil: Grougnet, Raphael. Universite de Paris, Descartes; FranciaFil: Sampietro, Diego Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentin

Compuestos Antifúngicos en Prosopis ruscifolia: identificación y análisis de su utilidad en el control de especies toxigénicas de Aspergillus

Se requieren nuevos agentes antifúngicos capaces de controlar a hongos del género Aspergillus que provocan pudriciones en maíz especialmente en granos almacenados, contaminándolos con aflatoxinas. La ingestión de estas micotoxinas puede ocasionar intoxicaciones en humanos y animales. El control químico de especies de Aspergillus se restringe al uso de preservantes de grado alimenticio, los cuales son fungistáticos, pueden alterar las características organolépticas del grano y en dosis subinhibitorias del crecimiento micelial pueden estimular la producción de aflatoxinas. Plantas autóctonas del NOA conocidas popularmente por sus propiedades antisépticas podrían proveer metabolitos secundarios capaces de detener el progreso de estos hongos. El objetivo de este trabajo fue determinar la actividad antifúngica de extractos de vinal (Prosopis ruscifolia) sobre especies de Aspergillus e identificar los metabolitos responsables. Partes aéreas de P. ruscifolia se extrajeron secuencialmente con hexano, diclorometano, acetato de etilo y metanol. La actividad antifúngica de estos extractos se ensayó sobre seis cepas de Aspergillus por bioautografía de siembra puntual y por microdilución, lo que permitió determinar que solo el extracto metanólico (fMeOH) presentó actividad antifúngica sobre las especies de Aspergillus ensayadas. Las dosis mínimas inhibitorias del crecimiento fúngico (DIM) fueron de 50-200 µg/ml y las concentraciones inhibitorias del 50% y 100% del crecimiento fúngico (CI50 y CIM) fueron 60-297 µg/ml y 50-1500 µg/ml respectivamente. Los constituyentes del fMeOH se separaron mediante cromatografía en columna de sílica gel y por cromatografía preparativa en capa fina. Las moléculas antifúngicas se estudiaron mediante revelados específicos en CCF y por espectrometría de resonancia magnética nuclear (RMN), identificándose los mismos como alcaloides (Juliflorina y Juliprosineno), un ciclitol (Pinitol) y una saponina triterpénica. El fMeOH de parte aéreas de P. ruscifolia no manifestó toxicidad sobre A. salina (CL5O > 1000 ppm), lo cual indica que el mismo no presenta citotoxicidad en eucarionates.

Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides

It is now widely-recognized that the view that herbal remedies have no adverse effects and/or toxicity is incorrect; some traditionally-used plants can present toxicity. The well-established popular use of Ageratum conyzoides has led to its inclusion in a category of medicinal crude drugs created by the Brazilian Health Surveillance Agency. Ageratum belongs to the Eupatorieae tribe, Asteraceae, and is described as containing toxic pyrrolizidine alkaloids. Aqueous extracts of Ageratum conyzoides L. harvested in Brazil (commercial, flowering and non-flowering samples) were prepared according to the prescribed method and analyzed by HPLC-HRMS. The pyrrolizidine alkaloids lycopsamine, dihydrolycopsamine, and acetyl-lycopsamine and their N-oxides, were detected in the analyzed extracts, lycopsamine and its N-oxide being known hepatotoxins and tumorigens. Together with the pyrrolizidine alkaloids identified by HPLC-HRMS, thirteen phenolic compounds were identified, notably, methoxylated flavonoids and chromenes. Toxicological studies on A. conyzoides are necessary, as is monitoring of its clinical use. To date, there are no established safety guidelines on pyrrolizidine alkaloids-containing plants, and their use in Brazil

Antifungal and antimycotoxigenic metabolites from native plants of northwest Argentina: isolation, identification and potential for control of Aspergillus species

Extracts from aerial parts of Prosopis ruscifolia, Bidens pilosa, Cercidium praecox and Phoradendron liga were assayed against toxigenic Aspergillus species. They were obtained by sequential extraction of the aerial parts with hexane (fHex), dichloromethane (fDCM), ethyl acetate (fEtOAc) and methanol (fMeOH). The fMeOH from P. ruscifolia showed the highest antifungal spectrum (MIC = 750–1500 µg mL−1; MID = 50–200 µg; DI = 1.7–3.0 mm). Indolizidine alkaloids (juliflorine and juliprosine) and tryptamine were identified with strong (MIC = 188 µg mL−1) and moderate antifungal activities (MIC = 750 µg mL−1), respectively, towards A. parasiticus and A. flavus. The fMeOH, the indolizidine alkaloids and tryptamine synergized the fungitoxic effect of potassium sorbate and propiconazole. They completely suppressed the biosynthesis of aflatoxins at concentrations of 47, 94 and 375 µg mL−1, respectively. Our results indicate that fMeOH and its identified alkaloids are promisory additives of commercial antifungals and are antiaflatoxigenic agents at concentrations below of those required for complete suppression of fungal growth.Fil: Gómez, Analia de Los Angeles. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Terán Baptista, Zareath Pamela. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Mandova ,Tzvetelina. 2laboratoire de Pharmacognosie, Umr/cnrs 8638 Comete, U; FranciaFil: Barouti,Angeliki. 2laboratoire de Pharmacognosie, Umr/cnrs 8638 Comete, U; FranciaFil: Kritsanida, Marina. 2laboratoire de Pharmacognosie, Umr/cnrs 8638 Comete, U; FranciaFil: Grougnet Raphael. 2laboratoire de Pharmacognosie, Umr/cnrs 8638 Comete, U; FranciaFil: Vattuone, Marta Amelia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Sampietro, Diego Alejandro. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentin

Chemical composition, antibacterial screening and cytotoxic activity of Chiliadenus antiatlanticus (Asteraceae) essential oil

The chemical composition and in vitro antibacterial and cytotoxic activities of the essential oil (EO) of Chiliadenus antiatlanticus (Emb. & Maire) Gomiz, an asteraceous species endemic to the southwest of Morocco, were investigated. The EO yield was 1.07 +/- 0.28 %, twenty-seven metabolites were identified representing more than 96.4 % of the total composition. Camphor (35.7 %) and derivatives, borneol (4.9 %) and camphene (4.2 %) together with intermedeol (19.9 %), alpha-pinene (15.5 %) and (E)-pinocarveol (4.1 %) were the major constituents. An antibacterial activity was noticed against 24 strains (all Gram-positive) out of 71 at MICs values=100 mu g/mL. The EO also showed significant toxicity towards liver HepG2 (55.8 % of cell viability) and melanoma B16 4A5 (41.6 % of cell viability) tumor cell lines at 100 mu g/mL.University of Paris; Ibn Zohr University; Fundacao para a Ciencia e a Tecnologia (FCT)Portuguese Foundation for Science and TechnologyEuropean Commissio

A review of phototoxic plants, their phototoxic metabolites, and possible developments as photosensitizers.

International audienceThis study provides a comprehensive overview of the current knowledge regarding phototoxic terrestrial plants and their phototoxic and photosensitizing metabolites. Within the 435,000 land plant species, only around 250 vascular plants have been documented as phototoxic or implicated in phototoxic occurrences in humans and animals. This work compiles a comprehensive catalog of these phototoxic plant species, organized alphabetically based on their taxonomic family. The dataset encompasses meticulous details including taxonomy, geographical distribution, vernacular names, and information on the nature and structure of their phototoxic and photosensitizing molecule(s). Subsequently, this study undertook an in‐depth investigation into phototoxic molecules, resulting in the compilation of a comprehensive and up‐to‐date list of phytochemicals exhibiting phototoxic or photosensitizing activity synthesized by terrestrial plants. For each identified molecule, an extensive review was conducted, encompassing discussions on its phototoxic activity, chemical family, occurrence in plant families or species, distribution within different plant tissues and organs, as well as the biogeographical locations of the producer species worldwide. The analysis also includes a thorough discussion on the potential use of these molecules for the development of new photosensitizers that could be used in topical or injectable formulations for antimicrobial and anticancer phototherapy as well as manufacturing of photoactive devices