Zanthosimuline and Related Pyranoquinolines as Antifungal Agents for Postharvest Fruit Disease Control

The natural product zanthosimuline and its 18 analogues were easily prepared from simple starting materials and evaluated in vitro against postharvest fruit fungal pathogens. The panel included Penicillium digitatum, Botrytis cinerea, Monilinia fructicola, and Rhizopus stolonifer; all of them causing relevant economic losses worldwide. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were determined, and the main structure?activity relationships were established. The biological activity observed was strongly increased by maintaining the prenyl side chain of zanthosimuline in an N-demethylated derivative. In addition, the compound that is the most active in the in vitro evaluation was tested in freshly harvested peaches exhibiting a promising brown rot control profile, comparable to the commercial agent carbendazim but demonstrating less toxicity against human liver cell lines.Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Caldo, Agustín J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; ArgentinaFil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentin

Botanical control of citrus green mold and peach brown rot on fruits assays using a persicaria acuminata phytochemically characterized extract

Persicaria acuminata (Polygonaceae) is a perennial herb that grows in the central area of Argentina and it is commonly used by native populations to heal infected wounds and other conditions related to fungal infections. In this article, we explored the in vitro antifungal activity of its ethyl acetate extract against a panel of three fruit phytopathogenic fungi including: Penicillium digitatum, P. italicum, and Monilinia fructicola. The sesquiterpenes isolated from the extract were also evaluated against these strains, demonstrating that the dialdehyde polygodial was the responsible for this activity. In order to encourage the use of the extract rather than the pure compound, we displayed ex vivo assays using fresh oranges and peaches inoculated with P. digitatum and M. fructicola, respectively, and subsequently treated by immersion with an extract solution of 250 and 62.5 µg/mL, respectively. There were no statistically significant differences between the treatments with commercial fungicides and the extract over the control of both fruit rots. The concentration of the active compound present in the extract used on fruit experiments was determined by Gas Chromatography-Mass Spectroscopy. Finally, cytotoxicity evaluation against Huh7 cells showed that P. acuminata extract was less cytotoxic than the commercial fungicides at the assayed concentrations. After these findings we could conclude that a chemically characterized extract of P. acuminata should be further developed to treat fungal diseases in fruits from an agro-ecological model.Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Seimandi, Gisela Marisol. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias Agropecuarias del Litoral. - Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral.; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Fernandez, Laura Noemí. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias Agropecuarias del Litoral. - Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral.; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Ruiz, Verónica Eugenia. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Instituto de Ciencias Agropecuarias del Litoral. - Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral.; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; Argentin

Control of Brown Rot Produced by Monilinia fructicola in Peaches Using a Full-Spectrum Extract of Zuccagnia punctata Cav

Brown rot of stone fruit, caused by Monilinia spp., is one of the most important diseases worldwide, causing significant production losses. Currently, the standard practices for controlling this infection consist of repetitive use of synthetic fungicides. The global tendency encourages the demand for high-quality food products harmless to health and the environment, leading to a reduction in the use of these types of substances. Zuccagnia punctata (Fabaceae) is a perennial shrub extensively used for the treatment of fungal and bacterial infections in Argentinean traditional medicine. In this study, we isolated and characterized (morphologically and molecularly) a pathogenic and virulent strain of Monilinia fructicola, which is the most hostile species of the genus. Consequently, we explored the in vitro antifungal activity of the ethanolic extract of Z. punctata against this phytopathogen. The chalcones 2′,4′-dihydroxy-3′-methoxychalcone and 2′,4′-dihydroxychalcone were isolated from the extract and evaluated against M. fructicola demonstrating that they were responsible for this activity. To promote full-spectrum extract rather than pure compounds, we performed ex-vivo assays using fresh peaches inoculated with the pathogen, and then treated by immersion in an extract solution of 250 µg/mL concentration. Treatment with Z. punctata extract did not show a statistically significant difference from commercial fungicides in the control of fruit rot. In addition, Huh7 cell cytotoxicity evaluation showed that Z. punctata extract was less cytotoxic than commercial fungicides at the assayed concentrations. Based on our research, this plant extract could potentially offer a safer alternative to commercial fungicides for treating peach brown rot.Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Stegmayer, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias Agropecuarias del Litoral. Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral; ArgentinaFil: Fernandez, Laura Noemí. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias Agropecuarias del Litoral. Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral; ArgentinaFil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; ArgentinaFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Ciencias Agropecuarias del Litoral. Universidad Nacional del Litoral. Instituto de Ciencias Agropecuarias del Litoral; Argentin

Evaluation of Argentinean medicinal plants and isolation of their bioactive compounds as an alternative for the control of postharvest fruits phytopathogenic fungi

One of the main problems that fruit health goes through in recent years is the difficult eradication of their fungal pathogens after harvesting. This concern to the whole world because it represents huge losses of production, fruit export restrictions and consumers distrust. One of the alternatives to solve this problem could be the exploration of plants and their active compounds, which have proven to be antifungal against human pathogens, but now applied to the treatment of fruits health. In this work, eighteen plant species that grow in Argentina were evaluated against four phytopathogenic fungi that greatly affect the postharvest stage of fruits commercially important to our country. All the species studied were at least active against one fungus of the panel, while three of them displayed high antifungal properties inhibiting the growth of selected pathogens. In addition, bio-guided fractionation of these most active extracts, led to the isolation of some compounds which proved to be responsible for their antifungal activity. Although they are known compounds and were previously isolated from other natural sources, this is the first time that they are evaluated for their phytopathogenic activities against this panel of fungi.Fil: Di Liberto, Melina Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Stegmayer, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; Argentin

Role of essential oils for the cure of human pathogenic fungal infections

Essential oils (EOs) are complex mixtures of low molecular weight compounds isolated from several plant families, mainly obtained by steam distillation and other simple techniques. The major components that provide the characteristic fragrance and biological properties to EOs are terpenoids and phenylpropanoid derivatives from mevalonic and shikimic acid pathway, respectively. They have been used by different medical traditional systems to treat a large number of diseases related to infections since ancient times. Many pharmaceutical and biological activities like, antibacterial, antifungal, anticancer, antimutagenic, antidiabetic, antiviral, anti-inflammatory, and antiprotozoal properties are assigned to them. Chemical characterization of EOs is extremely important since they often exhibit variations in their composition depending on different factors like plant variety, nutrition, application of fertilizers, climate, geographic location, seasonal variations, etc. The current status of human diseases produced by fungi, as well as a deep revision of drugs used to treat them and trends in the pharmaceutical industry for searching new antifungal drugs, are covered in this chapter. EOs as antifungal agents against human pathogens have also been discussed as alternative to drugs clinically used nowadays. We also provide the mechanism of antifungal action of these natural products.Fil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Castelli, Maria Victoria. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Rai, Mahendra. Sant Gadge Baba Amravati University; IndiaFil: Derita, Marcos Gabriel. Universidad Nacional del Litoral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentin

Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships

The antifungal activity of a library of twenty-four aromatic methoximes was examined against five representative postharvest phytopathogenic fungi. The panel included Penicillium digitatum, Penicillium italicum, Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, all of which cause relevant economic losses worldwide as a result of affecting harvested fruits. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were defined and the main structure?activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime was examined microscopically and the compound was also tested in freshly harvested peaches and oranges, exhibiting promising control profiles in both fruits, similar to those of the commercial agents Imazalil and Carbendazim.Fil: Cortés, Iván. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Derita, Marcos Gabriel. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Bracca, Andrea Beatriz Juana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentin

Plant phenolics and terpenoids as adjuvants of antibacterial and antifungal drugs

Background The intensive use of antibacterial and antifungal drugs has dramatically increased the microbial resistance and has led to a higher number of difficult-to-eradicate infections. Combination therapy with two or more antimicrobial drugs has emerged some years ago to overcome the issue, but it has proven to be not completely effective. Natural secondary metabolites of MW ≤ 500 represent promising adjuvants for antimicrobials and have been the object of several researches that have increased in the last two decades. Purpose The purpose of this Review is to do a literature search of the natural compounds that showed high enhancing capacity of antibacterials’ and antifungals’ effects against planktonic bacteria and fungi and to analyze which are the natural products most used in combination with a focus on polyphenols and terpenoids. Results One hundred of papers were collected for reviewing. Fifty six (56) of them deal with combinations of low MW natural products with antibacterial drugs against planktonic bacteria and forty four (44) on natural products with antifungal drugs against planktonic fungi. Of the antibacterial adjuvants, 41 (73%) were either polyphenols (27; 48%) or terpenes (14; 25%). The remaining 15 papers (27%), deal with different class of natural products. Since most natural potentiators belong to the terpene or phenolic structural types, a more detailed description of the works dealing with these type of compounds is provided here. Bacterial and fungal resistance mechanisms, the modes of action of the main classes of antibacterial and antifungal drugs and the methodologies most used to assess the type of interactions in the combinations were included in the Review too. Conclusions and perspectives Several promising results on the potentiation effects of antifungals’ and antibacterials’ activities by low MW natural products mainly on polyphenols and terpenes were reported in the literature and, in spite of that most works included only in vitro assays, this knowledge opens a wide range of possibilities for the combination antimicrobial therapy. Further research including in vivo assays and clinical trials are required to determine the relevance of these antimicrobial enhancers in the clinical area and should be the focus of future studies in order to develop new antimicrobial combination agents that overpass the drawbacks of the existing antibiotics and antifungals in clinical use.Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Raimondi, Marcela. Universidad Nacional de Rosario. Facultad de Ciencias Médicas; ArgentinaFil: Postigo, Agustina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Micología; Argentin

Activity of the pterophyllins 2 and 4 against postharvest fruit pathogenic fungi. Comparison with a synthetic analog and related intermediates

The antifungal activity of pterophyllin 2, pterophyllin 4, a 5-desmethyl analog of the latter and some of their synthetic intermediates, against three postharvest phytopathogenic fungi, was evaluated. The target fungi were Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, which affect fruits worldwide, causing important economic losses. The tests were carried out with imazalil and carbendazim as positive controls. Minimum inhibitory concentrations and minimum fungicidal concentrations were determined, and the morphology of the colonies was examined microscopically. In liquid medium, it was found that pterophyllin 4 exhibited selective fungicidal activity toward M. fructicola, whereas its congener pterophyllin 2 proved to be less potent and not selective and the 5-desmethyl analog of pterophyllin 4 displayed a different activity profile. Morphological changes were observed in the colonies exposed to pterophyllin 4. The results highlighted the importance of small structural features for the antifungal behavior and also suggested that, in Nature, the pterophyllins may act as plant defenses against pathogens.Fil: Pergomet, Jorgelina Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Bracca, Andrea Beatriz Juana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentin

Incidence of water in the concentration of anticancer secondary metabolites present in Catharanthus roseus (VINCA)

Las moléculas derivadas del metabolismo secundario de plantas han sido objeto de estudio por su utilidad contra enfermedades que afectan al ser humano. En este sentido, la planta de Catharanthus roseus (Vinca) sintetiza alcaloides indólicos terpénicos como vincristina y vinblastina (dímeros de sus precursores catarantina y vindolina), que desde la década del 80 se utilizan en terapia oncológica...Fil: Alvarez, Norma Hortensia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Stegmayer, María Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Di Liberto, Melina Gabriela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Alesso, Carlos Agustín. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Bouzo, CarloS. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; ArgentinaFil: Derita, Marcos Gabriel. Universidad Nacional del Litoral. Facultad de Ciencias Agrarias; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaXXXII Reunión Argentina, XVI Congreso Latinoamericano de Fisiología VegetalCórdobaArgentinaSociedad Argentina de Fisiología Vegeta