logo

OR SEARCH CITATIONS

My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2005, 53, 24, 9431-9435
RETURN TO ISSUEPREVArticleNEXT

Novel Chemotaxonomic Markers of the Alternaria infectoria Species-Group

View Author Information
Center for Microbial Biotechnology, BioCentrum-DTU, Søltofts Plads, Building 221, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark, Plant Extracts Research Unit, New Zealand Institute for Crop & Food Research Limited, and Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand
Cite this: J. Agric. Food Chem. 2005, 53, 24, 9431–9435
Publication Date (Web):October 26, 2005
https://doi.org/10.1021/jf0513213
Copyright © 2005 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
454
Altmetric
-
Citations
33
LEARN ABOUT THESE METRICS
Read OnlinePDF (79 KB)
Get e-Alerts
SUBJECTS:

Abstract

Two new structurally related metabolites, novae-zelandin A (1) and novae-zelandin B (2), as well as the novel metabolite 4Z-infectopyrone (3) were purified from extracts of filamentous fungi belonging to the Alternaria infectoria species-group. The structures were elucidated by a combination of 1D and 2D NMR spectroscopic data and MS data. 1−3 are important chemotaxonomic markers of the A. infectoria species-group and exhibit structures similar to those of known biologically active compounds, suggesting that they could be potential phytotoxins.

Keywords: Alternaria; chemotaxonomy; α-pyrone; infectopyrone; novae-zelandin; phytotoxin

†

 Technical University of Denmark.

‡

 Department of Chemistry, Plant Extracts Research Unit, University of Otago.

§

 Department of Chemistry, University of Otago.

*

 Corresponding author. Phone:  +45 4525 2632. Fax:  +45 4588 4922. E-mail:  [email protected]

Cited By

This article is cited by 33 publications.

  1. Shotaro Hoshino, Takaaki Mitsuhashi, Takashi Kikuchi, Chin Piow Wong, Hiroyuki Morita, Takayoshi Awakawa, Makoto Fujita, Ikuro Abe. Structural Elucidation of Tenebrathin: Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius. Organic Letters 2019, 21 (16) , 6519-6522. https://doi.org/10.1021/acs.orglett.9b02443
  2. Ubonta Sommart, Vatcharin Rukachaisirikul, Saowanit Saithong, Souwalak Phongpaichit, Jariya Sakayaroj, Sita Preedanon, Kittipong Chainok, Teerayut Khunrong. 2-Oxaspiro[4.5]decane and α -pyrenocine derivatives from the endophytic fungus Roussoella sp. PSU-H51. Natural Product Research 2021, , 1-10. https://doi.org/10.1080/14786419.2021.1910692
  3. Antonio Gallo, Francesca Ghilardelli, Alberto Stanislao Atzori, Severino Zara, Barbara Novak, Johannes Faas, Francesco Fancello. Co-Occurrence of Regulated and Emerging Mycotoxins in Corn Silage: Relationships with Fermentation Quality and Bacterial Communities. Toxins 2021, 13 (3) , 232. https://doi.org/10.3390/toxins13030232
  4. Ming-Fang Liao, Kai Wang, Jin-Wei Ren, Li Liu, Lei Cai, Jun-Jie Han, Hong-Wei Liu. 2 H -Pyranone and isocoumarin derivatives isolated from the plant pathogenic fungus Leptosphaena maculans. Journal of Asian Natural Products Research 2019, 21 (10) , 939-946. https://doi.org/10.1080/10286020.2018.1485661
  5. Stefania Somma, Maria Teresa Amatulli, Mario Masiello, Antonio Moretti, Antonio Francesco Logrieco. Alternaria species associated to wheat black point identified through a multilocus sequence approach. International Journal of Food Microbiology 2019, 293 , 34-43. https://doi.org/10.1016/j.ijfoodmicro.2019.01.001
  6. Javier Moraga, Wesley Gomes, Cristina Pinedo, Jesús M. Cantoral, James R. Hanson, María Carbú, Carlos Garrido, Rosa Durán-Patrón, Isidro G. Collado. The current status on secondary metabolites produced by plant pathogenic Colletotrichum species. Phytochemistry Reviews 2019, 18 (1) , 215-239. https://doi.org/10.1007/s11101-018-9590-0
  7. Andrea Patriarca, Lucía da Cruz Cabral, María Agustina Pavicich, Kristian Fog Nielsen, Birgitte Andersen. Secondary metabolite profiles of small-spored Alternaria support the new phylogenetic organization of the genus. International Journal of Food Microbiology 2019, 291 , 135-143. https://doi.org/10.1016/j.ijfoodmicro.2018.11.022
  8. Teresa Romero-Cortes, Víctor Hugo Pérez España, Pablo Antonio López Pérez, Guadalupe Del Carmen Rodríguez-Jimenes, Víctor J. Robles-Olvera, José Esteban Aparicio Burgos, Jaime Alioscha Cuervo-Parra. Antifungal activity of vanilla juice and vanillin against Alternaria alternata. CyTA - Journal of Food 2019, 17 (1) , 375-383. https://doi.org/10.1080/19476337.2019.1586776
  9. Theresa Zwickel, Sandra M. Kahl, Michael Rychlik, Marina E. H. Müller. Chemotaxonomy of Mycotoxigenic Small-Spored Alternaria Fungi – Do Multitoxin Mixtures Act as an Indicator for Species Differentiation?. Frontiers in Microbiology 2018, 9 https://doi.org/10.3389/fmicb.2018.01368
  10. Alireza Poursafar, Youbert Ghosta, Alexandra S. Orina, Philipp B. Gannibal, Mohammad Javan-Nikkhah, Daniel P. Lawrence. Taxonomic study on Alternaria sections Infectoriae and Pseudoalternaria associated with black (sooty) head mold of wheat and barley in Iran. Mycological Progress 2018, 17 (3) , 343-356. https://doi.org/10.1007/s11557-017-1358-1
  11. Kresten Jon Kromphardt Olsen, Amy Rossman, Birgitte Andersen. Metabolite production by species of Stemphylium. Fungal Biology 2018, 122 (2-3) , 172-181. https://doi.org/10.1016/j.funbio.2017.12.012
  12. Hong-Chuan Song, Dan Qin, Mei-Jun Han, Ling Wang, Kuo Zhang, Jin-Yan Dong. Bioactive 2-pyrone metabolites from an endophytic Phomopsis asparagi SWUKJ5.2020 of Kadsura angustifolia. Phytochemistry Letters 2017, 22 , 235-240. https://doi.org/10.1016/j.phytol.2017.06.020
  13. Virginia Elena Fernández Pinto, Andrea Patriarca. Alternaria Species and Their Associated Mycotoxins. 2017,,, 13-32. https://doi.org/10.1007/978-1-4939-6707-0_2
  14. Morten Hertz, Iben Ravnborg Jensen, Laura Østergaard Jensen, Søren Nøhr Thomsen, Jacob Winde, Morten Simonsen Dueholm, Lydia Henriette Sørensen, Rasmus Dam Wollenberg, Hans Otto Sørensen, Teis Esben Sondergaard, Jens Laurids Sørensen. The fungal community changes over time in developing wheat heads. International Journal of Food Microbiology 2016, 222 , 30-39. https://doi.org/10.1016/j.ijfoodmicro.2016.01.018
  15. Daniel P. Lawrence, Francesca Rotondo, Philipp B. Gannibal. Biodiversity and taxonomy of the pleomorphic genus Alternaria. Mycological Progress 2016, 15 (1) https://doi.org/10.1007/s11557-015-1144-x
  16. S.M. Kahl, A. Ulrich, A.A. Kirichenko, M.E.H. Müller. Phenotypic and phylogenetic segregation of Alternaria infectoria from small-spored Alternaria species isolated from wheat in Germany and Russia. Journal of Applied Microbiology 2015, 119 (6) , 1637-1650. https://doi.org/10.1111/jam.12951
  17. Antonio Gallo, Gianluca Giuberti, Jens Frisvad, Terenzio Bertuzzi, Kristian Nielsen. Review on Mycotoxin Issues in Ruminants: Occurrence in Forages, Effects of Mycotoxin Ingestion on Health Status and Animal Performance and Practical Strategies to Counteract Their Negative Effects. Toxins 2015, 7 (8) , 3057-3111. https://doi.org/10.3390/toxins7083057
  18. Zhijun Yang, LiXia Bao, Yu Yin, Gang Ding, Mei Ge, Daijie Chen, Xiuping Qian. Pyrenocines N–O: two novel pyrones from Colletotrichum sp. HCCB03289. The Journal of Antibiotics 2014, 67 (11) , 791-793. https://doi.org/10.1038/ja.2014.59
  19. Ahmed M. Metwaly, Frank R. Fronczek, Guoyi Ma, Hazem A. Kadry, Atef A. El-Hela, Abd-Elsalam I. Mohammad, Stephen J. Cutler, Samir A. Ross. Antileukemic α-pyrone derivatives from the endophytic fungus Alternaria phragmospora. Tetrahedron Letters 2014, 55 (24) , 3478-3481. https://doi.org/10.1016/j.tetlet.2014.04.085
  20. Daniel P. Lawrence, Philipp B. Gannibal, Frank M. Dugan, Barry M. Pryor. Characterization of Alternaria isolates from the infectoria species-group and a new taxon from Arrhenatherum, Pseudoalternaria arrhenatheria sp. nov.. Mycological Progress 2014, 13 (2) , 257-276. https://doi.org/10.1007/s11557-013-0910-x
  21. Thiago M. Casella, Véronique Eparvier, Hugues Mandavid, Audrey Bendelac, Guillaume Odonne, Laura Dayan, Christophe Duplais, Laila S. Espindola, Didier Stien. Antimicrobial and cytotoxic secondary metabolites from tropical leaf endophytes: Isolation of antibacterial agent pyrrocidine C from Lewia infectoria SNB-GTC2402. Phytochemistry 2013, 96 , 370-377. https://doi.org/10.1016/j.phytochem.2013.10.004
  22. Makoto Hashimoto, Satomi Ishida, Yasuyo Seshime, Katsuhiko Kitamoto, Isao Fujii. Aspergillus oryzae type III polyketide synthase CsyB uses a fatty acyl starter for the biosynthesis of csypyrone B compounds. Bioorganic & Medicinal Chemistry Letters 2013, 23 (20) , 5637-5640. https://doi.org/10.1016/j.bmcl.2013.08.036
  23. Jingfeng Lou, Linyun Fu, Youliang Peng, Ligang Zhou. Metabolites from Alternaria Fungi and Their Bioactivities. Molecules 2013, 18 (5) , 5891-5935. https://doi.org/10.3390/molecules18055891
  24. Birgit Jensen, Inge M.B. Knudsen, Birgitte Andersen, Kristian Fog Nielsen, Ulf Thrane, Dan Funck Jensen, John Larsen. Characterization of microbial communities and fungal metabolites on field grown strawberries from organic and conventional production. International Journal of Food Microbiology 2013, 160 (3) , 313-322. https://doi.org/10.1016/j.ijfoodmicro.2012.11.005
  25. Miguel Ángel Pavón, Agustín Luna, Silvia de la Cruz, Isabel González, Rosario Martín, Teresa García. PCR-based assay for the detection of Alternaria species and correlation with HPLC determination of altenuene, alternariol and alternariol monomethyl ether production in tomato products. Food Control 2012, 25 (1) , 45-52. https://doi.org/10.1016/j.foodcont.2011.10.009
  26. Richard K. Phipps, Charlotte H. Gotfredsen, Søren R. Paludan, Jens C. Frisvad, Kathrine Eriksen, Bent O. Petersen, Jens Ø. Duus, Thomas O. Larsen. Hesseltins B–G, novel meroterpenoids from a new Penicillium species. Tetrahedron Letters 2011, 52 (5) , 598-601. https://doi.org/10.1016/j.tetlet.2010.11.140
  27. Miguel Ángel Pavón, Isabel González, Nicolette Pegels, Rosario Martín, Teresa García. PCR detection and identification of Alternaria species-groups in processed foods based on the genetic marker Alt a 1. Food Control 2010, 21 (12) , 1745-1756. https://doi.org/10.1016/j.foodcont.2010.08.004
  28. Lada Ivanova, Dirk Petersen, Silvio Uhlig. Phomenins and fatty acids from Alternaria infectoria. Toxicon 2010, 55 (6) , 1107-1114. https://doi.org/10.1016/j.toxicon.2009.12.017
  29. Birgitte Andersen, Jens Laurids Sørensen, Kristian Fog Nielsen, Bert Gerrits van den Ende, Sybren de Hoog. A polyphasic approach to the taxonomy of the Alternaria infectoria species–group. Fungal Genetics and Biology 2009, 46 (9) , 642-656. https://doi.org/10.1016/j.fgb.2009.05.005
  30. A. O. Berestetskiy. A review of fungal phytotoxins: from basic studies to practical use. Applied Biochemistry and Microbiology 2008, 44 (5) , 453-465. https://doi.org/10.1134/S0003683808050013
  31. Jens C. Frisvad, Birgitte Andersen, Ulf Thrane. The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi. Mycological Research 2008, 112 (2) , 231-240. https://doi.org/10.1016/j.mycres.2007.08.018
  32. A. Perelló, M. Sisterna. Formation of Lewia infectoria , the teleomorph of Alternaria infectoria , on wheat in Argentina. Australasian Plant Pathology 2008, 37 (6) , 589. https://doi.org/10.1071/AP08060
  33. S Arunmozhi Balajee, Kieren A Marr. Phenotypic and genotypic identification of human pathogenic aspergilli. Future Microbiology 2006, 1 (4) , 435-445. https://doi.org/10.2217/17460913.1.4.435

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE