Insecticidal activity of paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Agricultural and Food Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html.[EN] Paraherquamide H (1) and paraherquamide 1 (2), two new compounds of the paraherquamide (PHQ) family, together with the already known paraherquamide A (3), paraherquamide B (4), paraherquamide E (5), VM55596 (N-oxide paraherquamide) (6), paraherquamide VM55597 (7), and five known diketopiperazines (8-12) have been isolated from the culture broth of Penicillium cluniae Quintanilla. The structure of 1 and 2, on the basis of NMR and MS analysis, was established. It is worth noticing that, in both cases, an unusual oxidative substitution in C-16 was found, which had only previously been detected in PHQ 7. Isolated compounds were tested for insecticidal activity against the hemipteran Oncopeltus fasciatus Dallas. Mortality data have allowed preliminary structure activity relationships to be proposed. The most potent product was 5 with a LD50 of 0.089,mu g/nymph.The authors acknowledge the Conselleria de Educación y Ciencia de la C. Valenciana for the doctoral grant to M. P. L, the Fundación José y Ana Royo, the Comisión Interministerial de Ciencia y Tecnología (CICYT) and the Conselleria de Agricultura, P. y A. de la C. Valenciana, for financial supportLópez-Gresa, MP.; Gonzalez Más, MC.; Ciavatta, ML.; Ayala Mingol, I.; Moya, P.; Primo, J. (2006). Insecticidal activity of paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae. Journal of Agricultural and Food Chemistry. 54(8):2921-2925. https://doi.org/10.1021/jf0530998S2921292554

Isolation and Structural Elucidation of Eight New Related Analogues of the Mycotoxin (-)-Botryodiplodin from Penicillium coalescens

[EN] Bioassay-guided fractionation of the organic extract derived from the terrestrial fungus Penicillium coalescens led to the isolation of the known mycotoxin (-)-botryodiplodin (1) and eight new structurally related analogues (2-9). The structures of the novel compounds were determined by MS and NMR studies, including 1D and 2D NMR. A likely biogenetic pathway from the aldehydic open form of 1 (C-7 unit, U1) is proposed for these metabolites. Among all the isolated metabolites, only (-)-1 showed antifungal, antibacterial, and insecticidal activity. This latter activity appears to be a new property attributed to (-)-1.Cabedo Escrig, N.; López-Gresa, MP.; Primo, J.; Ciavatta, ML.; Gonzalez Más, MC. (2007). Isolation and Structural Elucidation of Eight New Related Analogues of the Mycotoxin (-)-Botryodiplodin from Penicillium coalescens. Journal of Agricultural and Food Chemistry. 55(17):6977-6983. doi:10.1021/jf071568vS69776983551

New bioactive hydrogenated linderazulene-derivatives from the gorgonian Echinogorgia complexa

[EN] Chemical analysis of the secondary metabolite pattern of the gorgonian Echinogorgia complexa, collected along South Indian coasts, showed the presence of two new tricyclic guaiane furanosesquiterpenes, iso-echinofuran (3) and 8,9-dihydro-linderazulene (4), co-occurring with the known echinofuran (5) and structurally related to the pigment linderazulene (1). The unprecedented molecules 3 and 4 were characterized by spectral methods, mainly by NMR techniques. Compounds 3¿5 displayed moderate activity in the mitochondrial respiratory chain inhibition assay.Manzo, E.; Ciavatta, ML.; López-Gresa, MP.; Gavagnin, M.; Villani, G.; Naik, CG.; Cimino, G. (2007). New bioactive hydrogenated linderazulene-derivatives from the gorgonian Echinogorgia complexa. Tetrahedron Letters. 48(14):2569-2571. https://doi.org/10.1016/j.tetlet.2007.02.020S25692571481

Aceites esenciales: productos antimicrobianos y antioxidantes naturales en la industria agroalimentaria

[ES] Los consumidores son conscientes del peligro derivado del uso de antioxidantes y antimicrobianos sintéticos en la industria agroalimentaria, demandando alternativas más seguras y ecológicas. En este estudio, se ha determinado la actividad antioxidante de aceites esenciales comerciales mediante el método DPPH y su efecto antimicrobiano frente a la bacteria Pseudomonas syringae y el hongo fitopatógeno Fusarium oxysporum a través del empleo del método estandarizado de disco. Los aceites esenciales de clavo, ajedrea, canela y orégano, así como carvacrol, mostraron la máxima actividad antioxidante, comparable a antioxidantes establecidos. El aceite esencial de gaulteria fue el más potente inhibidor del crecimiento de P. syringae en las dosis más altas (20 y 10 µL) ensayadas. El aceite esencial de orégano, así como su componente principal carvacrol, detuvieron el crecimiento de la bacteria incluso a la dosis más baja ensayada (1 µL). Los aceites esenciales de canela, orégano y menta inhibieron el desarrollo de F. oxysporum en todas las dosis (20, 10 y 5 µL) aplicadas. En general, la mayoría de aceites esenciales mostraron más actividad antifúngica que antibacteriana y antioxidante.[EN] Consumers are aware of the dangers arising from the use of synthetic antioxidants and antimicrobials in the agrifood industry, demanding safer and "greener" alternatives. In this study, the antioxidant activity of commercial essential oils through DPPH method, their antimicrobial effects against the bacterium Pseudomonas syringae and the phytopathogenic fungus Fusarium oxysporum by means of the standardized disk method were determined. Clove along with winter savory, cinnamon and oregano essential oils as well as carvacrol showed the highest antioxidant activity comparable to reference standards. Wintergreen essential oil was the most potent inhibitor against P. syringae growth at the highest doses (20 and 10 µL). Oregano essential oil and its main component carvacrol were able to stop the bacterium growth even at the lowest treatment (1 µL). Cinnamon, oregano and peppermint essential oils inhibited F. oxysporum development at all doses (20, 10 and 5 µL) assayed. In general, most of the essential oils displayed more antifungal than antibacterial and antioxidant activities.Ibáñez, MD.; López-Gresa, MP.; Lisón, P.; Rodrigo Bravo, I.; Belles Albert, JM.; González-Mas, MC.; Blázquez, MA. (2020). Essential oils as natural antimicrobial and antioxidant products in the Agrifood Industry. Nereis. Revista Iberoamericana Interdisciplinar de Métodos, Modelización y Simulación. (12):55-69. https://doi.org/10.46583/nereis_2020.12.585S55691

Distinctive physiological and molecular responses to cold stress among cold-tolerant and cold-sensitive Pinus halepensis seed sources

Background: Forest species ranges are confined by environmental limitations such as cold stress. The natural range shifts of pine forests due to climate change and proactive-assisted population migration may each be constrained by the ability of pine species to tolerate low temperatures, especially in northern latitudes or in high altitudes. The aim of this study is to characterize the response of cold-tolerant versus cold-sensitive Pinus halepensis (P. halepensis) seedlings at the physiological and the molecular level under controlled cold conditions to identify distinctive features which allow us to explain the phenotypic difference. With this objective gas-exchange and water potential was determined and the photosynthetic pigments, soluble sugars, glutathione and free amino acids content were measured in seedlings of different provenances under control and cold stress conditions. Results: Glucose and fructose content can be highlighted as a potential distinctive trait for cold-tolerant P. halepensis seedlings. At the amino acid level, there was a significant increase and accumulation of glutathione, proline, glutamic acid, histidine, arginine and tryptophan along with a significant decrease of glycine. Conclusion: Our results established that the main difference between cold-tolerant and cold-sensitive seedlings of P. halepensis is the ability to accumulate the antioxidant glutathione and osmolytes such as glucose and fructose, proline and arginine.This study is a part of the research project: “Application of molecular biology techniques in forest restoration in Mediterranean environments, PAID-05-11” funded by the Universitat Politècnica de València (UPV), program for supporting R&D of new multidisciplinary research lines. The authors are grateful to the Ministerio de Economía y Competitividad AGL2014–57431-P and BIO2016–77776-P. AV was supported by project Survive-2 (CGL2015–69773-C2–2-P MINECO/FEDER) by the Spanish Government and Prometeo program (DESESTRES Generalitat Valenciana). CEAM is funded by Generalitat Valenciana

Wild edible fool’s watercress, a potential crop with high nutraceutical properties

Background Fool’s watercress (Apium nodiflorum) is an edible vegetable with potential as a new crop. However, little information is available regarding the antioxidant properties of the plant and the individual phenolics accounting for this capacity are unknown. Methods The antioxidant properties of twenty-five wild populations were analysed and individual phenolics present in the species reported and compared with celery and parsley. The antioxidant activity was measured as the 2,2-diphenyl-1-picrylhydrazyl hydrate (DPPH) free radical scavenging capacity, and the total phenolics content (TPC) via the Folin-Ciocalteu procedure. The individual phenolics constituents were determined via high performance liquid chromatography (HPLC) as aglycones. Results The average DPPH and TPC of fool’s watercress were 28.1 mg Trolox g−1 DW and 22.3 mg of chlorogenic acid equivalents g−1 DW, respectively, much higher than those of celery and parsley. Significant differences for both DPPH and TPC, which may be explained by either genotype or environmental factors, were detected among groups established according to geographical origin. Quercetin was identified as the major phenolic present in the leaves of the species, unlike parsley and celery, in which high amounts of apigenin and luteolin were determined. Quercetin represented 61.6% of the phenolics targeted in fool’s watercress, followed by caffeic acid derivatives as main hydroxycinnamic acids. Discussion The study reports the high antioxidant properties of fool’s watercress based on a large number of populations. Results suggest that quercetin accounts for an important share of the antioxidant capacity of this potential new crop. The study also provides a basis for future breeding programs, suggesting that selection by geographical locations may result in differences in the antioxidant properties

Editorial: Flavonoids: From Biosynthesis and Metabolism to Health Benefits

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New C-21 Delta(20) pregnanes, inhibitors of mitochondrial respiratory chain, from Indopacific octocoral Carijoa sp

[EN] Two new compounds, pregnanes 1 and 2, the known pregnane 3 and a series of known chlorinated prostanoids (4¿9) have been isolated from the Indian octocoral Carijoa sp. Their structures have been elucidated by spectroscopic methods, mainly by 1D and 2D NMR. The new compounds were potent inhibitors of the mitochondrial respiratory chain.Ciavatta, ML.; López-Gresa, MP.; Manzo, E.; Gavagnin, M.; Wahidulla, S.; Cimino, G. (2004). New C-21 Delta(20) pregnanes, inhibitors of mitochondrial respiratory chain, from Indopacific octocoral Carijoa sp. Tetrahedron Letters. 45(41):7745-7748. https://doi.org/10.1016/j.tetlet.2004.08.061S77457748454

Accumulation of phenolic compounds in Money Maker plants infected with citrus exocortis viroid (CEVd) or tomato spotted wilt virus (TSWV).

<p>Levels of free <b>A)</b> and total <b>B)</b> gentisic acid (GA) and salicylic acid (SA) in mock-inoculated and infected Money Maker tomato leaves. Plants were inoculated with either CEVd or TSWV and samples were collected at the indicated times (weeks post-inoculation, wpi) for both infected (I) and mock-inoculated (M) leaves, and then analyzed by HPLC-fluorescence detection. Total SA is the sum of free SA and SA glucoside and total GA is the sum of free GA and GA xyloside. Data correspond to the mean ± SD of three biological replicates of one representative experiment. The experiments were repeated at least 3 times.</p

Accumulation of Pathogenesis-Related (PR) proteins in Money Maker and NahG tomato plants upon viroid and virus infection.

<p>Plants were inoculated with either Citrus Exocortis Viroid (CEVd, <b>A)</b> or Tomato Spotted Wilt Virus (TSWV, <b>B)</b>, and samples were collected at the indicated times (weeks post-inoculation, wpi) for both infected and mock-inoculated plants. Crude extracts were separated by SDS-PAGE and the presence of PR1 and P23 was detected by immunoblot. Upper panels correspond to Coomassie Blue stained SDS-PAGE gels (14% acrylamide). Lower panels show the immunostaining of P23 (23 kDa) and PR1 (14 kDa).</p