74 research outputs found
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
Ethylene is Involved in Symptom Development and Ribosomal Stress of Tomato Plants upon Citrus Exocortis Viroid Infection
[EN] Citrus exocortis viroid (CEVd) is known to cause different symptoms in citrus trees, and its mechanism of infection has been studied in tomato as an experimental host, producing ribosomal stress on these plants. Some of the symptoms caused by CEVd in tomato plants resemble those produced by the phytohormone ethylene. The present study is focused on elucidating the relationship between CEVd infection and ethylene on disease development. To this purpose, the ethylene insensitive Never ripe (Nr) tomato mutants were infected with CEVd, and several aspects such as susceptibility to infection, defensive response, ethylene biosynthesis and ribosomal stress were studied. Phenotypic characterization revealed higher susceptibility to CEVd in these mutants, which correlated with higher expression levels of both defense and ethylene biosynthesis genes, as well as the ribosomal stress marker SlNAC082. In addition, Northern blotting revealed compromised ribosome biogenesis in all CEVd infected plants, particularly in Nr mutants. Our results indicate a higher ethylene biosynthesis in Nr mutants and suggest an important role of this phytohormone in disease development and ribosomal stress caused by viroid infection.Vázquez Prol, F.; López-Gresa, MP.; Rodrigo Bravo, I.; Belles Albert, JM.; Lisón, P. (2020). Ethylene is Involved in Symptom Development and Ribosomal Stress of Tomato Plants upon Citrus Exocortis Viroid Infection. Plants. 9(5):1-15. https://doi.org/10.3390/plants9050582S11595Flores, R., Hernández, C., Alba, A. E. M. de, Daròs, J.-A., & Serio, F. D. (2005). Viroids and Viroid-Host Interactions. Annual Review of Phytopathology, 43(1), 117-139. doi:10.1146/annurev.phyto.43.040204.140243Adkar‐Purushothama, C. R., & Perreault, J. (2019). Current overview on viroid–host interactions. WIREs RNA, 11(2). doi:10.1002/wrna.1570Di Serio, F., Flores, R., Verhoeven, J. T. J., Li, S.-F., Pallás, V., Randles, J. W., … Owens, R. A. (2014). Current status of viroid taxonomy. Archives of Virology, 159(12), 3467-3478. doi:10.1007/s00705-014-2200-6Verhoeven, J. th. j., Jansen, C. C. C., Willemen, T. M., Kox, L. F. F., Owens, R. A., & Roenhorst, J. W. (2004). Natural infections of tomato by Citrus exocortis viroid, Columnea latent viroid, Potato spindle tuber viroid and Tomato chlorotic dwarf viroid. European Journal of Plant Pathology, 110(8), 823-831. doi:10.1007/s10658-004-2493-5López-Gresa, M. P., Lisón, P., Yenush, L., Conejero, V., Rodrigo, I., & Bellés, J. M. (2016). Salicylic Acid Is Involved in the Basal Resistance of Tomato Plants to Citrus Exocortis Viroid and Tomato Spotted Wilt Virus. PLOS ONE, 11(11), e0166938. doi:10.1371/journal.pone.0166938Wang, Y., Wu, J., Qiu, Y., Atta, S., Zhou, C., & Cao, M. (2019). Global Transcriptomic Analysis Reveals Insights into the Response of ‘Etrog’ Citron (Citrus medica L.) to Citrus Exocortis Viroid Infection. Viruses, 11(5), 453. doi:10.3390/v11050453Jia, C., Zhang, L., Liu, L., Wang, J., Li, C., & Wang, Q. (2013). Multiple phytohormone signalling pathways modulate susceptibility of tomato plants to Alternaria alternata f. sp. lycopersici. Journal of Experimental Botany, 64(2), 637-650. doi:10.1093/jxb/ers360Van Loon, L. C., Geraats, B. P. J., & Linthorst, H. J. M. (2006). Ethylene as a modulator of disease resistance in plants. Trends in Plant Science, 11(4), 184-191. doi:10.1016/j.tplants.2006.02.005Bellés, J. M., & Conejero, V. (1989). Ethylene Mediation of the Viroid-Like Syndrome Induced by Ag+Ions inGynura aurantiacaDC Plants. Journal of Phytopathology, 124(4), 275-284. doi:10.1111/j.1439-0434.1989.tb04924.xDubois, M., Van den Broeck, L., & Inzé, D. (2018). The Pivotal Role of Ethylene in Plant Growth. Trends in Plant Science, 23(4), 311-323. doi:10.1016/j.tplants.2018.01.003Yang, S. F., & Hoffman, N. E. (1984). Ethylene Biosynthesis and its Regulation in Higher Plants. 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Prunus persica
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Native-Invasive Plants vs. Halophytes in Mediterranean Salt Marshes: Stress Tolerance Mechanisms in Two Related Species
Dittrichia viscosa is a Mediterranean ruderal species that over the last decades has expanded into new habitats, including coastal salt marshes, ecosystems that are per se fragile and threatened by human activities. To assess the potential risk that this native-invasive species represents for the genuine salt marsh vegetation, we compared its distribution with that of Inula crithmoides, a taxonomically related halophyte, in three salt marshes located in “La Albufera” Natural Park, near the city of Valencia (East Spain). The presence of D. viscosa was restricted to areas of low and moderate salinity, while I. crithmoides was also present in the most saline zones of the salt marshes. Analyses of the responses of the two species to salt and water stress treatments in controlled experiments revealed that both activate the same physiological stress tolerance mechanisms, based essentially on the transport of toxic ions to the leaves—where they are presumably compartmentalized in vacuoles—and the accumulation of specific osmolytes for osmotic adjustment. The two species differ in the efficiency of those mechanisms: salt-induced increases in Na+ and Cl− contents were higher in I. crithmoides than in D. viscosa, and the osmolytes (especially glycine betaine, but also arabinose, fructose and glucose) accumulated at higher levels in the former species. This explains the (slightly) higher stress tolerance of I. crithmoides, as compared to D. viscosa, established from growth inhibition measurements and their distribution in nature. The possible activation of K+ transport to the leaves under high salinity conditions may also contribute to salt tolerance in I. crithmoides. Oxidative stress level—estimated from malondialdehyde accumulation—was higher in the less tolerant D. viscosa, which consequently activated antioxidant responses as a defense mechanism against stress; these responses were weaker or absent in the more tolerant I. crithmoides. Based on these results, we concluded that although D. viscosa cannot directly compete with true halophytes in highly saline environments, it is nevertheless quite stress tolerant and therefore represents a threat for the vegetation located on the salt marshes borders, where several endemic and threatened species are found in the area of study.Work in the UPV laboratories was partly funded by a grant to OV from the Spanish Ministry of Science and Innovation (Project CGL2008-00438/BOS), with contribution from the European Regional Development Fund.Peer reviewedPeer Reviewe
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
Induction of gentisic acid 5-O-beta-xylopyranoside in tomato and cucumber plants infected by different pathogens
[EN] Tomato plants infected with the citrus exocortis viroid exhibited strongly elevated levels of a compound identified as 2,5-dihydroxy-benzoic acid (gentisic acid, GA) 5-O-beta-D-xylopyranoside. The compound accumulated early in leaves expressing mild symptoms from both citrus exocortis viroid-infected tomato, and prunus necrotic ringspot virus-infected cucumber plants, and progressively accumulated concomitant with symptom development. The work presented here demonstrates that GA, mainly associated with systemic infections in compatible plant-pathogen interactions (Belles, J.M., Garro, R., Fayos, J., Navarro, P., Primo, J., Conejero, V., 1999. Gentisic acid as a pathogen-inducible signal, additional to salicylic acid for activation of plant defenses in tomato. Mol. Plant-Microbe Interact. 12, 2272351, is conjugated to xylose. Notably, this result contrasts with those previously found in other plant-pathogen interactions in which phenolics analogues of GA as benzoic or salicylic acids, are conjugated to glucose. (c) 2005 Elsevier Ltd. All rights reserved.This work has been supported by Grant #BMC2000-1136 from Comisión Interministerial de Ciencia y Tecnología, Spanish Ministry of Science and Technology.Fayos Febrer, J.; Belles Albert, JM.; López-Gresa, MP.; Primo Millo, J.; Conejero Tomás, V. (2006). Induction of gentisic acid 5-O-beta-xylopyranoside in tomato and cucumber plants infected by different pathogens. Phytochemistry. 67(2):142-148. doi:10.1016/j.phytochem.2005.10.014S14214867
Salicylic Acid Is Involved in the Basal Resistance of Tomato Plants to Citrus Exocortis Viroid and Tomato Spotted Wilt Virus
[EN] Tomato plants expressing the NahG transgene, which prevents accumulation of endogenous salicylic acid (SA), were used to study the importance of the SA signalling pathway in basal defence against Citrus Exocortis Viroid (CEVd) or Tomato Spotted Wilt Virus (TSWV). The lack of SA accumulation in the CEVd- or TSWV-infected NahG tomato plants led to an early and dramatic disease phenotype, as compared to that observed in the corresponding parental Money Maker. Addition of acibenzolar-S-methyl, a benzothiadiazole (BTH), which activates the systemic acquired resistance pathway downstream of SA signalling, improves resistance of NahG tomato plants to CEVd and TSWV. CEVd and TSWV inoculation induced the accumulation of the hydroxycinnamic amides p-coumaroyltyramine, feruloyltyramine, caffeoylputrescine, and feruloylputrescine, and the defence related proteins PR1 and P23 in NahG plants earlier and with more intensity than in Money Maker plants, indicating that SA is not essential for the induction of these plant defence metabolites and proteins. In addition, NahG plants produced very high levels of ethylene upon CEVd or TSWV infection when compared with infected Money Maker plants, indicating that the absence of SA produced additional effects on other metabolic pathways. This is the first report to show that SA is an important component of basal resistance of tomato plants to both CEVd and TSWV, indicating that SA-dependent defence mechanisms play a key role in limiting the severity of symptoms in CEVd- and TSWV-infected NahG tomato plants.This work was supported by grant BIO2012-33419 from the Spanish Ministry of Economy and Competitiveness received by JMB. The funder had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.López-Gresa, MP.; Lisón, P.; Yenush, L.; Conejero Tomás, V.; Rodrigo Bravo, I.; Belles Albert, JM. (2016). Salicylic Acid Is Involved in the Basal Resistance of Tomato Plants to Citrus Exocortis Viroid and Tomato Spotted Wilt Virus. PLoS ONE. 11(11). https://doi.org/10.1371/journal.pone.0166938S111
Tomato glycosyltransferase Twi1 plays a role in flavonoid glycosylation and defence against virus
[EN] Background: Secondary metabolites play an important role in the plant defensive response. They are produced as
a defence mechanism against biotic stress by providing plants with antimicrobial and antioxidant weapons. In
higher plants, the majority of secondary metabolites accumulate as glycoconjugates. Glycosylation is one of the
commonest modifications of secondary metabolites, and is carried out by enzymes called glycosyltransferases.
Results: Here we provide evidence that the previously described tomato wound and pathogen-induced
glycosyltransferase Twi1 displays in vitro activity toward the coumarins scopoletin, umbelliferone and esculetin, and the
flavonoids quercetin and kaempferol, by uncovering a new role of this gene in plant glycosylation. To test its activity
in vivo, Twi1-silenced transgenic tomato plants were generated and infected with Tomato spotted wilt virus. The Twi1-
silenced plants showed a differential accumulation of Twi1 substrates and enhanced susceptibility to the virus.
Conclusions: Biochemical in vitro assays and transgenic plants generation proved to be useful strategies to assign a
role of tomato Twi1 in the plant defence response. Twi1 glycosyltransferase showed to regulate quercetin and
kaempferol levels in tomato plants, affecting plant resistance to viral infection.This work was supported by grant BIO2012-33419 from the Direccion General de Programas y Transferencia de Conocimiento, Spanish Ministry of Science and Innovation, and grant AICO/2017/048 from the Valencian Local Government (Generalitat Valenciana, Spain). LC was supported by a predoctoral fellowship (ACIF/2010/231) from the Valencian Local Government (Generalitat Valenciana, Spain). None of the funding bodies was involved in the design of the study, the collection, analysis, and interpretation of the data, nor in the writing of the manuscript, which was made entirely by the authors.Campos Beneyto, L.; López-Gresa, MP.; Fuertes, D.; Belles Albert, JM.; Rodrigo Bravo, I.; Lisón, P. (2019). Tomato glycosyltransferase Twi1 plays a role in flavonoid glycosylation and defence against virus. BMC Plant Biology. 19:1-17. https://doi.org/10.1186/s12870-019-2063-9S11719Kliebenstein DJ. 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(Z)-3-Hexenyl Butyrate induces stomata closure and ripening in Vitis vinifera
[EN] Agronomy solutions for modifying pre-harvest grape ripening are needed for a more sustainable viticulture. Field experiments were performed inVitis viniferaL. vines to study the effect of the previously described stomata-closing compound (Z)-3-hexenyl butyrate (HB). Exogenous treatments at different doses were periodically carried out using a randomized block design. Firstly, we observed that HB was able to induce stomatal closure in grapevine plants. Under field conditions, the application of HB around veraison induced a higher color intensity in berries, and vines treated at higher doses reached this stage earlier than the un-treated controls. There was also a clear increase in both grape anthocyanin concentration and total soluble solids without having a negative impact on total yield. We therefore, confirm the role of HB as a universal natural stomatal closure compound and propose a new use for HB in viticulture as a ripening inducer, by accelerating anthocyanin accumulation.This research was funded by Grant INNVAL10/18/005 from the Agencia Valenciana de la Innovacio (Spain). C.P. was a recipient of a predoctoral contract of the Generalitat Valenciana (ACIF/2019/187). D.S.I. is supported by AEI-FEDER grant AGL2017-83738-C3-3-R.Payá Montes, C.; López-Gresa, MP.; Intrigliolo, DS.; Rodrigo Bravo, I.; Belles Albert, JM.; Lisón, P. (2020). (Z)-3-Hexenyl Butyrate induces stomata closure and ripening in Vitis vinifera. Agronomy. 10(8):1-12. https://doi.org/10.3390/agronomy10081122S112108Zoccatelli, G., Zenoni, S., Savoi, S., Dal Santo, S., Tononi, P., Zandonà, V., … Tornielli, G. B. (2013). Skin pectin metabolism during the postharvest dehydration of berries from three distinct grapevine cultivars. 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Induction of cinnamate 4-hydroxylase and phenylpropanoids in virus-infected cucumber and melon plants
[EN] In the present work, we have looked for the nature of the phenylpropanoids biosynthesized during the plant-pathogen reaction of two systems, Cucumis sativus and Cucumis melo infected with either prunus necrotic ringspot virus (PNRSV) or melon necrotic spot virus (MNSV), respectively. An accumulation of p-coumaric, caffeic and/or ferulic acids was observed in infected plant extracts hydrolysed with P-glucosidase or esterase. Analysis of undigested samples by HPLC/ESI revealed that these compounds are mainly forming esters with glucose: 1-O-coumaroyl-beta-glucose, 1-O-caffeoyl-beta-glucose, and 1-O-fer-uloyl-beta-glucose. Cinnamic acid 4-hydroxylase (C4H, EC 1.14.13.11), the second enzyme of the plant phenylpropanoid pathway, plays a pivotal role in the synthesis of these hydroxycinnamic acids. Thus, we have isolated and characterised a cDNA clone encoding this enzyme from PNRSV-infected cucumber, and a partial cDNA from MNSV-infected melon leaves. The deduced amino acid sequence revealed a notable degree of identity with homologous C4H enzymes from other plant species. In agreement with the induction of the phenylpropanoids presently described, it is reported that in cucumber and melon leaves, both viral infections studied induced C4H mRNA expression. A similar induction was observed for the first pherylpropanoid biosynthetic enzyme, phyenylalanine ammonia-lyase (PAL, EC 4.3.1.5), and for chitinase and peroxidase defence-related genes.We gratefully acknowledge Dr. Lynne Yenush for critical
reading of the manuscript and helpful discussions, and L.
Latorre, and L. Coracha´n for the technical support in the
greenhouse. The authors want to acknowledge the detailed
suggestions of the referees. This work was supported by Grant
BMC2000-1136 from Comisio´n Interministerial de Ciencia y
Tecnologı´a, Spanish Ministry of Science and TechnologyS52453317
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