Secondary metabolite profiles of small-spored Alternaria support the new phylogenetic organization of the genus

The group of the small-spored Alternaria species is particularly relevant in foods due to its high frequency and wide distribution in different crops. These species are responsible for the accumulation of mycotoxins and bioactive secondary metabolites in food. The taxonomy of the genus has been rece...

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Autor principal: Patriarca, A.
Otros Autores: da Cruz Cabral, L., Pavicich, M.A, Nielsen, K.F, Andersen, B.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier B.V. 2019
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024 7 |2 scopus  |a 2-s2.0-85057167106 
024 7 |2 cas  |a alternariol, 641-38-3; tenuazonic acid, 610-88-8, 75652-74-3; lactone, 1338-03-0; altenuene; alternariol; alternariol monomethyl ether; Lactones; Mycotoxins; Peptides, Cyclic; tentoxin; Tenuazonic Acid 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a IJFMD 
100 1 |a Patriarca, A. 
245 1 0 |a Secondary metabolite profiles of small-spored Alternaria support the new phylogenetic organization of the genus 
260 |b Elsevier B.V.  |c 2019 
270 1 0 |m Patriarca, A.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pabellón II, 3° Piso, Intendente Güiraldes 2160, Argentina; email: andreap@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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504 |a Chulze, S.N., Torres, A.M., Dalcero, A.M., Etcheverry, M.G., Ramirez, M.L., Farnochi, M.C., Alternaria mycotoxins in sunflower seeds: incidence and distribution of the toxins in oil and meal (1995) J. Food Prot., 58, pp. 1133-1134 
504 |a da Cruz Cabral, L., Terminiello, L., Fernández Pinto, V., Nielsen, K.F., Patriarca, A., Natural occurrence of mycotoxins and toxigenic capacity of Alternaria strains from mouldy peppers (2016) Int. J. Food Microbiol., 236, pp. 155-160 
504 |a da Cruz Cabral, L., Rodriguero, M., Stenglein, S., Nielsen, K.F., Patriarca, A., Characterization of small-spored Alternaria from Argentinean crops through a polyphasic approach (2017) Int. J. Food Microbiol., 257, pp. 206-215 
504 |a Dugan, F.M., Peever, T.L., Morphological and cultural differentiation of described species of Alternaria from Poaceae (2002) Mycotaxon, 83, pp. 229-264 
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504 |a Frisvad, J.C., Andersen, B., Thrane, U., The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi (2008) Mycol. Res., 112, pp. 231-240 
504 |a Gannibal, P.B., Lawrence, D.P., Distribution of Alternaria species among sections. 3. Sections Infectoriae and Pseudoalternaria (2016) Mycotaxon, 131, pp. 781-790 
504 |a Geiseler, O., Podlech, J., Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8, 9‑dehydroxylarone, and nectriapyrone (2012) Tetrahedron, 68, pp. 7280-7287 
504 |a Greco, M., Patriarca, A., Terminiello, L., Pinto, V.F., Pose, G., Toxigenic Alternaria species from Argentinean blueberries (2012) Int. J. Food Microbiol., 154, pp. 187-191 
504 |a Gu, W., Bioactive metabolites from Alternaria brassicicola ML-P08, an endophytic fungus residing in Malus halliana (2009) World J. Microbiol. Biotechnol., 25, p. 1677 
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504 |a Hickert, S., Bergmann, M., Ersen, S., Cramer, B., Humpf, H.U., Survey of Alternaria toxin contamination in food from the German market, using a rapid HPLC–MS/MS approach (2016) Mycotoxin Res., 32, pp. 7-18 
504 |a Ivanova, L., Petersen, D., Uhlig, S., Phomenins and fatty acids from Alternaria infectoria (2010) Toxicon, 55, pp. 1107-1114 
504 |a Kildgaard, S., Mansson, M., Dosen, I., Klitgaard, A., Frisvad, J.C., Larsen, T.O., Nielsen, K.F., Accurate dereplication of bioactive secondary metabolites from marine-derived fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library (2014) Mar. Drugs, 12, pp. 3681-3705 
504 |a Königs, P., Rinker, B., Maus, L., Nieger, M., Rheinheimer, J., Waldvogel, S., Structural revision and synthesis of altechromone A (2010) J. Nat. Prod., 73, pp. 2064-2066 
504 |a Larsen, T.O., Perry, N.B., Andersen, B., Infectopyrone, a potential mycotoxin from Alternaria infectoria (2003) Tetrahedron Lett., 44, pp. 4511-4513 
504 |a Lawrence, D.P., Gannibal, P.B., Peever, T.L., Pryor, B., The sections of Alternaria: formalizing species-group concepts (2013) Mycologia, 105 (3), pp. 530-546 
504 |a Lawrence, D.P., Gannibal, P.B., Dugan, F.M., Pryor, B.M., Characterization of Alternaria isolates from the infectoria species-group and a new taxon from Arrhenatherum, Pseudoalternaria arrhenatheria sp. nov (2014) Mycol. Prog., 13, pp. 257-276 
504 |a Lawrence, D.P., Rotondo, F., Gannibal, P.B., Biodiversity and taxonomy of the pleomorphic genus Alternaria (2016) Mycol. Prog., 15 (3), pp. 1-22 
504 |a López, P., Venema, D., de Rijk, T., de Kok, A., Scholten, J.M., Mol, H.G.J., de Nijs, M., Occurrence of Alternaria toxins in food products in the Netherlands (2016) Food Control, 60, pp. 196-204 
504 |a Nemecek, G., Cudaj, J., Podlech, J., Revision of the structure and total synthesis of altenuisol (2012) Eur. J. Org. Chem., 2012, pp. 3863-3870 
504 |a Nielsen, K.F., Larsen, T.O., The importance of mass spectrometric dereplication in fungal secondary metabolite analysis (2015) Front. Microbiol., 6 (71), pp. 1-15 
504 |a Oviedo, M., Barros, G., Chulze, S., Ramirez, M., Natural occurrence of alternariol and alternariol monomethyl ether in soya beans (2012) Mycotoxin Res., 28, pp. 169-174 
504 |a Patriarca, A., Alternaria in food products (2016) Curr. Opin. Food Sci., 11, pp. 1-9 
504 |a Patriarca, A., Azcarate, M., Terminiello, L., Pinto, V.F., Mycotoxin production by Alternaria strains isolated from Argentinean wheat (2007) Int. J. Food Microbiol., 119, pp. 219-222 
504 |a Pedras, M.S.C., Chumala, P.B., Phomapyrones from blackleg causing phytopathogenic fungi: isolation, structure determination, biosyntheses and biological activity (2005) Phytochemistry, 66, pp. 81-87 
504 |a Pedras, M.S.C., Park, M.R., Metabolite diversity in the plant pathogen Alternaria brassicicola: factors affecting production of brassicicolin A, depudecin, phomapyrone A and other metabolites (2015) Mycologia, 107, pp. 1138-1150 
504 |a Peres, N.A.R., Agostini, J.P., Timmer, L.W., Outbreaks of Alternaria brown spot of citrus in Brazil and Argentina (2003) Plant Dis., 87, p. 750 
504 |a Pero, R.W., Posner, H., Blois, M., Harvan, D., Spalding, J.W., Toxicity of metabolites produced by the “Alternaria” (1973) Environ. Health Perspect., 4, pp. 87-94 
504 |a Pitt, J.I., Hocking, A.D., Fungi and Food Spoilage (2009), Springer Boston, MA; Pose, G., Ludemann, V., Segura, J., Fernández Pinto, V., Mycotoxin production by Alternaria strains isolated from tomatoes affected by Blackmold in Argentina (2004) Mycotoxin Res., 20, p. 80 
504 |a Pose, G.N., Ludemann, V., Fernandez, D., Segura, J.A., Pinto, V.F., Alternaria species associated with ‘moldy heart’ on peaches in Argentina (2010) Trop. Plant Pathol., 35, pp. 174-177 
504 |a Robiglio, A.L., Lopez, S.E., Mycotoxin production by Alternaria alternata strains isolated from red delicious apples in Argentina (1995) Int. J. Food Microbiol., 24, pp. 413-417 
504 |a Rychlik, M., Lepper, H., Weidner, C., Asam, S., Risk evaluation of the Alternaria mycotoxin tenuazonic acid in foods for adults and infants and subsequent risk management (2016) Food Control, 68, pp. 181-185 
504 |a Samson, R.A., Houbraken, J., Thrane, U., Frisvad, J.C., Andersen, B., Food and Indoor Fungi (2010) CBS Laboratory Manual Series 2, , CBS-Fungal Biodiversity Centre Utrecht 
504 |a Sato, H., Konoma, K., Sakamura, S., Three new phytotoxins produced by Pyrenochaeta terrestris: pyrenochaetic acids A, B and C (1981) Agric. Biol. Chem., 45, pp. 1675-1679 
504 |a Serdani, M., Ji-Chuan, K.A.N.G., Andersen, B., Crous, P.W., Characterisation of Alternaria species-groups associated with core rot of apples in South Africa (2002) Mycol. Res., 106, pp. 561-569 
504 |a Simmons, E.G., Alternaria taxonomy: Current status, viewpoint, challenge (1992) Alternaria: Biology, Plant Diseases, and Metabolites, pp. 1-35. , J. Chelkowski A. Visconti Elsevier New York 
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504 |a Solfrizzo, M., Recent advances on Alternaria mycotoxins (2017) Curr. Opin. Food Sci., 17, pp. 57-61 
504 |a Terminiello, L., Patriarca, A., Pose, G., Fernández Pinto, V., Occurrence of alternariol, alternariol monomethyl ether and tenuazonic acid in Argentinean tomato puree (2006) Mycotoxin Res., 22, pp. 236-240 
504 |a Vargas Trinidad, A., Ganoza, F.Q., Fernández Pinto, V., Patriarca, A., Determination of mycotoxin profiles characteristic of Alternaria strains isolated from Malbec grapes (2015) BIO Web of Conferences, p. 02004. , EDP Sciences 
504 |a Walravens, J., Mikula, H., Rychlik, M., Asam, S., Ediage, E.N., Di Mavungu, J.D., Van Landschoot, A., De Saeger, S., Development and validation of an ultra-high-performance liquid chromatography tandem mass spectrometric method for the simultaneous determination of free and conjugated Alternaria toxins in cereal-based foodstuffs (2014) J. Chromatogr. A, 1372, pp. 91-101 
504 |a Webley, D.J., Jackson, K.L., Mullins, J.D., Hocking, A.D., Pitt, J.I., Alternaria toxins in weather-damaged wheat and sorghum in the 1995–1996 Australian harvest (1997) Aust. J. Agric. Res., 48, pp. 1249-1256 
504 |a Woudenberg, J.H.C., Groenewald, J.Z., Binder, M., Crous, P.W., Alternaria redefined (2013) Stud. Mycol., 75, pp. 171-212 
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504 |a Zwickel, T., Klaffke, H., Richards, K., Rychlik, M., Development of a high performance liquid chromatography tandem mass spectrometry based analysis for the simultaneous quantification of various Alternaria toxins in wine, vegetable juices and fruit juices (2016) J. Chromatogr. A, 1455, pp. 74-85 
504 |a Zwickel, T., Kahl, S.M., Rychlik, M., Müller, M.E.H., Chemotaxonomy of mycotoxigenic small-spored Alternaria fungi – do multitoxin mixtures act as an indicator for species differentiation? (2018) Front. Microbiol., 9, p. 1368 
520 3 |a The group of the small-spored Alternaria species is particularly relevant in foods due to its high frequency and wide distribution in different crops. These species are responsible for the accumulation of mycotoxins and bioactive secondary metabolites in food. The taxonomy of the genus has been recently revised with particular attention on them; several morphospecies within this group cannot be segregated by phylogenetic methods, and the most recent classifications proposed to elevate several phylogenetic species-groups to the taxonomic status of section. The purpose of the present study was to compare the new taxonomic revisions in Alternaria with secondary metabolite profiles with special focus on sections Alternaria and Infectoriae and food safety. A total of 360 small-spored Alternaria isolates from Argentinean food crops (tomato fruit, pepper fruit, blueberry, apple, wheat grain, walnut, pear, and plum) was morphologically identified to species-group according to Simmons (2007), and their secondary metabolite profile was determined. The isolates belonged to A. infectoria sp.-grp. (19), A. tenuissima sp.-grp. (262), A. arborescens sp.-grp. (40), and A. alternata sp.-grp. (7); 32 isolates, presenting characteristics overlapping between the last three groups, were classified as Alternaria sp. A high chemical diversity was observed; 78 different metabolites were detected, 31 of them of known chemical structure. The isolates from A. infectoria sp.-grp. (=Alternaria section Infectoriae) presented a specific secondary metabolite profile, different from the other species-groups. Infectopyrones, novae-zelandins and phomapyrones were the most frequent metabolites produced by section Infectoriae. Altertoxin-I and alterperylenol were the only compounds that these isolates produced in common with members of section Alternaria. None of the well-known Alternaria toxins, considered relevant in foods, namely alternariol (AOH), alternariol monomethyl ether (AME), tenuazonic acid (TeA), tentoxin (TEN) or altenuene (ALT), were produced by isolates of this section. On the other hand, strains from section Alternaria (A. tenuissima, A. arborescens, and A. alternata sp.-grps.) shared a common metabolite profile, indistinguishable from each other. AOH, AME, ALT, TEN, and TeA were the most frequently mycotoxins produced, together with pyrenochaetic acid A and altechromone A. Alternaria section Alternaria represents a substantial risk in food, since their members in all types of crops are able to produce the toxic metabolites. © 2018 Elsevier B.V.  |l eng 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica 
536 |a Detalles de la financiación: Universidad de Buenos Aires, UBACYT 20020130200262BA 
536 |a Detalles de la financiación: Ministerio de Ciencia, Tecnología e Innovación Productiva, PICT-2015-2228 
536 |a Detalles de la financiación: This work was supported by Universidad de Buenos Aires [ UBACYT 20020130200262BA ] and Agencia Nacional de Promoción Científica y Tecnológica , MINCYT [ PICT-2015-2228 ]. 
593 |a Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Laboratorio de Microbiología de Alimentos. CONICET, Instituto de Micología y Botánica (INMIBO), Buenos Aires, Argentina 
593 |a Department of Biotechnology and Biomedicine, Technical University of Denmark, Kgs. Lyngby, DK-2800, Denmark 
690 1 0 |a ALTERNARIA 
690 1 0 |a FOOD SAFETY 
690 1 0 |a SECONDARY METABOLITE PROFILES 
690 1 0 |a SECTION ALTERNARIA 
690 1 0 |a SECTION INFECTORIAE 
690 1 0 |a ALTENUENE 
690 1 0 |a ALTERNARIOL 
690 1 0 |a ALTERNARIOL MONOMETHYL ETHER 
690 1 0 |a ALTERPERYLENOL 
690 1 0 |a ALTERTOXIN I 
690 1 0 |a INFECTOPYRONE DERIVATIVE 
690 1 0 |a MYCOTOXIN 
690 1 0 |a NATURAL PRODUCT 
690 1 0 |a NOVAE ZELANDIN DERIVATIVE 
690 1 0 |a PHOMAPYRONE DERIVATIVE 
690 1 0 |a TENTOXIN 
690 1 0 |a TENUAZONIC ACID 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a CYCLOPEPTIDE 
690 1 0 |a LACTONE 
690 1 0 |a MYCOTOXIN 
690 1 0 |a TENUAZONIC ACID 
690 1 0 |a ALTERNARIA 
690 1 0 |a ALTERNARIA ALTERNATA 
690 1 0 |a ALTERNARIA ARBORESCENS 
690 1 0 |a ALTERNARIA INFECTORIA 
690 1 0 |a ALTERNARIA TENUISSIMA 
690 1 0 |a APPLE 
690 1 0 |a ARTICLE 
690 1 0 |a BLUEBERRY 
690 1 0 |a FOOD CROP 
690 1 0 |a FOOD SAFETY 
690 1 0 |a FUNGAL STRAIN 
690 1 0 |a FUNGUS ISOLATION 
690 1 0 |a GENUS 
690 1 0 |a GRAIN 
690 1 0 |a METABOLITE 
690 1 0 |a MORPHOSPECIES 
690 1 0 |a NONHUMAN 
690 1 0 |a PEAR 
690 1 0 |a PEPPER 
690 1 0 |a PHYLOGENY 
690 1 0 |a PLUM 
690 1 0 |a TEA 
690 1 0 |a TOMATO 
690 1 0 |a WALNUT 
690 1 0 |a WHEAT 
690 1 0 |a ALTERNARIA 
690 1 0 |a ANALYSIS 
690 1 0 |a BLACK PEPPER 
690 1 0 |a CLASSIFICATION 
690 1 0 |a CROP 
690 1 0 |a FOOD CONTAMINATION 
690 1 0 |a FOOD CONTROL 
690 1 0 |a FRUIT 
690 1 0 |a MALUS 
690 1 0 |a METABOLISM 
690 1 0 |a MICROBIOLOGY 
690 1 0 |a PYRUS 
690 1 0 |a SECONDARY METABOLISM 
690 1 0 |a ALTERNARIA 
690 1 0 |a BLUEBERRY PLANTS 
690 1 0 |a CROPS, AGRICULTURAL 
690 1 0 |a FOOD CONTAMINATION 
690 1 0 |a FOOD MICROBIOLOGY 
690 1 0 |a FRUIT 
690 1 0 |a JUGLANS 
690 1 0 |a LACTONES 
690 1 0 |a LYCOPERSICON ESCULENTUM 
690 1 0 |a MALUS 
690 1 0 |a MYCOTOXINS 
690 1 0 |a PEPTIDES, CYCLIC 
690 1 0 |a PHYLOGENY 
690 1 0 |a PIPER NIGRUM 
690 1 0 |a PRUNUS DOMESTICA 
690 1 0 |a PYRUS 
690 1 0 |a SECONDARY METABOLISM 
690 1 0 |a TENUAZONIC ACID 
690 1 0 |a TRITICUM 
651 4 |a ARGENTINA 
651 4 |a ARGENTINA 
700 1 |a da Cruz Cabral, L. 
700 1 |a Pavicich, M.A. 
700 1 |a Nielsen, K.F. 
700 1 |a Andersen, B. 
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