Gulypyrones A and B and Phomentrioloxins B and C Produced by Diaporthe gulyae, a Potential Mycoherbicide for Saffron Thistle (Carthamus lanatus)
Article
Andolfi, Anna, Boari, Angela, Evidente, Marco, Cimmino, Alessio, Vurro, Maurizio, Ash, Gavin and Evidente, Antonio. 2015. "Gulypyrones A and B and Phomentrioloxins B and C Produced by Diaporthe gulyae, a Potential Mycoherbicide for Saffron Thistle (Carthamus lanatus)." Journal of Natural Products. 78 (4), pp. 623-629. https://doi.org/10.1021/np500570h
| Article Title | Gulypyrones A and B and Phomentrioloxins B and C Produced by Diaporthe gulyae, a Potential Mycoherbicide for Saffron Thistle (Carthamus lanatus) |
|---|---|
| ERA Journal ID | 40471 |
| Article Category | Article |
| Authors | Andolfi, Anna (Author), Boari, Angela (Author), Evidente, Marco (Author), Cimmino, Alessio (Author), Vurro, Maurizio (Author), Ash, Gavin (Author) and Evidente, Antonio (Author) |
| Journal Title | Journal of Natural Products |
| Journal Citation | 78 (4), pp. 623-629 |
| Number of Pages | 7 |
| Year | Apr 2015 |
| Place of Publication | United States |
| ISSN | 0163-3864 |
| 1520-6025 | |
| Digital Object Identifier (DOI) | https://doi.org/10.1021/np500570h |
| Web Address (URL) | https://pubs.acs.org/doi/10.1021/np500570h |
| Abstract | A virulent strain of Diaporthe gulyae, isolated from stem cankers of sunflower and known to be pathogenic to saffron thistle, has been shown to produce both known and previously undescribed metabolites when grown in either static liquid culture or a bioreactor. Together with phomentrioloxin, a phytotoxic geranylcyclohexenetriol recently isolated from a strain of Phomopsis sp., two new phytotoxic trisubstituted α-pyrones, named gulypyrones A and B (1 and 2), and two new 1,O- and 2,O-dehydro derivatives of phomentrioloxin, named phomentrioloxins B and C (3 and 4), were isolated from the liquid culture filtrates of D. gulyae. These four metabolites were characterized as 6-[(2S)2-hydroxy-1-methylpropyl]-4-methoxy-5-methylpyran-2-one (1), 6-[(1E)-3-hydroxy-1-methylpropenyl]- 4-methoxy-3-methylpyran-2-one (2), 4,6-dihydroxy-5-methoxy-2-(7-methyl-3-methyleneoct-6-en-1-ynyl)cyclohex-2-enone (3), and 2,5-dihydroxy-6-methoxy-3-(7-methyl-3-methyleneoct-6-en-1-ynyl)cyclohex-3-enone (4) using spectroscopic and chemical methods. The absolute configuration of the hydroxylated secondary carbon of the 2-hydroxy-1-methylpropyl side chain at C-6 of gulypyrone A was determined as S by applying a modified Mosher’s method. Other well-known metabolites were also isolated including 3-nitropropionic, succinic, and p-hydroxy- and p-methylbenzoic acids, p-hydroxybenzaldehyde, and nectriapyrone. When assayed using a 5 mM concentration on punctured leaf disks of weedy and crop plants, apart from 3-nitropropionic acid (the main metabolite responsible for the strong phytotoxicity of the culture filtrate), phomentrioloxin B caused small, but clear, necrotic spots on a number of plant species, whereas gulypyrone A caused leaf necrosis on Helianthus annuus plantlets. All other compounds were weakly active or inactive. |
| Keywords | Ascomycota; Australia; Benzaldehydes; Carthamus; Cyclohexanols; Herbicides; Molecular Structure; Nitro Compounds; Propionates; Pyrones |
| Contains Sensitive Content | Does not contain sensitive content |
| ANZSRC Field of Research 2020 | 310803. Plant cell and molecular biology |
| Public Notes | Files associated with this item cannot be displayed due to copyright restrictions. |
| Byline Affiliations | University of Naples Federico II, Italy |
| Institute of Sciences and Food Production, Italy | |
| Charles Sturt University | |
| Institution of Origin | University of Southern Queensland |
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Adorada, Dante L., Stodart, Benjamin J., Tpoi, Roni P., Costa, Severino S. and Ash, Gavin J.. 2013. "Bacteria associated with sheath browning and grain discoloration of rice in East Timor and implications for Australia’s biosecurity." Australasian Plant Disease Notes. 8 (1), pp. 43-47. https://doi.org/10.1007/s13314-013-0092-zDevelopment of a genomics-based LAMP (loop-mediated isothermal amplification) assay for detection of Pseudomonas fuscovaginae from rice
Ash, Gavin J., Lang, Jillian M., Triplett, Lindsay R., Stodart, Benjamin J., Verdier, Valerie, Vera Cruz, Casiana, Rott, Philippe and Leach, Jan E.. 2014. "Development of a genomics-based LAMP (loop-mediated isothermal amplification) assay for detection of Pseudomonas fuscovaginae from rice ." Plant Disease: an international journal of applied plant pathology. 98 (7), pp. 909-915. https://doi.org/10.1094/PDIS-09-13-0957-REIdentification of virulence associated loci in the emerging broad host range plant pathogen Pseudomonas fuscovaginae
Patel, Hitendra Kumar, Matiuzzo, Maura, Bertani, Iris, Bigirimana, Vincent De Paul, Ash, Gavin J., Hofte, Monica and Venturi, Vittoria. 2014. "Identification of virulence associated loci in the emerging broad host range plant pathogen Pseudomonas fuscovaginae." BMC Microbiology. 14 (274), pp. 1-13. https://doi.org/10.1186/s12866-014-0274-7Identification of QTLs associated with resistance to phomopsis pod blight (Diaporthe toxica) in Lupinus albus
Cowley, Raymond, Luckett, David J., Ash, Gavin J., Harper, John D. I., Vipin, Cina A., Raman, Harsh and Ellwood, Simon. 2014. "Identification of QTLs associated with resistance to phomopsis pod blight (Diaporthe toxica) in Lupinus albus." Breeding Science. 64 (1), pp. 83-89. https://doi.org/10.1270/jsbbs.64.83Prioritising plant-parasitic nematode species biosecurity risks using self organising maps
Singh, Sunil K., Paini, Dean R., Ash, Gavin J. and Hodda, Mike. 2014. "Prioritising plant-parasitic nematode species biosecurity risks using self organising maps." Biological Invasions. 16 (7), pp. 1515-1530. https://doi.org/10.1007/s10530-013-0588-7Responses of physiological indexes and leaf epicuticular waxes of Brassica napus to Sclerotinia sclerotiorum infection
Ni, Y., Guo, Y. -J., Wang, J., Xia, R. -E., Wang, X. -Q., Ash, G. and Li, J. -N.. 2014. "Responses of physiological indexes and leaf epicuticular waxes of Brassica napus to Sclerotinia sclerotiorum infection." Plant Pathology. 63 (1), pp. 174-184. https://doi.org/10.1111/ppa.12060The genome sequence of the biocontrol fungus Metarhizium anisopliae and comparative genomics of Metarhizium species
Pattemore, Julie A., Hane, James K., Williams, Angela H., Wilson, Bree A. L., Stodart, Ben J. and Ash, Gavin J.. 2014. "The genome sequence of the biocontrol fungus Metarhizium anisopliae and comparative genomics of Metarhizium species." BMC Genomics. 15 (1), pp. 1-15. https://doi.org/10.1186/1471-2164-15-660Keeping ‘one step ahead’ of invasive species: using an integrated framework to screen and target species for detailed biosecurity risk assessment
Singh, Sunil K., Ash, Gavin J. and Hodda, Mike. 2015. "Keeping ‘one step ahead’ of invasive species: using an integrated framework to screen and target species for detailed biosecurity risk assessment." Biological Invasions. 17 (4), pp. 1069-1086. https://doi.org/10.1007/s10530-014-0776-0Implications of bacterial contaminated seed lots and endophytic colonization by Pseudomonas fuscovaginae on rice establishment
Adorada, D. L., Stodart, B. J., Pangga, I. B. and Ash, G. J.. 2015. "Implications of bacterial contaminated seed lots and endophytic colonization by Pseudomonas fuscovaginae on rice establishment." Plant Pathology. 64 (1), pp. 43-50. https://doi.org/10.1111/ppa.12243Hierarchical genetic variation of Botryosphaeriaceae species associated with decline and dieback of grapevine in south-eastern Australia
Qui, Y., Steel, C. C., Ash, G. J. and Savocchia, S.. 2015. "Hierarchical genetic variation of Botryosphaeriaceae species associated with decline and dieback of grapevine in south-eastern Australia." Australian Journal of Grape and Wine Research. 21 (3), pp. 458-467. https://doi.org/10.1111/ajgw.12144Structure and Absolute Configuration of Kongiidiazadione, a NewPhytotoxic 3-Substituted-5-Diazenylcyclopentendione Produced by Diaporthe Kongii
Evidente, Marco, Boari, Angela, Vergura, Stefania, Cimmino, Alessio, Vurro, Maurizio, Ash, Gavin, Superchi, Stefano and Evidente, Antonio. 2015. "Structure and Absolute Configuration of Kongiidiazadione, a NewPhytotoxic 3-Substituted-5-Diazenylcyclopentendione Produced by Diaporthe Kongii." Chirality: the pharmacological, biological, and chemical consequences of molecular asymmetry. 27 (9), pp. 557-562. https://doi.org/10.1002/chir.22466Whole genome phylogeny of Bacillus by feature frequency profiles (FFP)
Wang, Aisuo and Ash, Gavin J.. 2015. "Whole genome phylogeny of Bacillus by feature frequency profiles (FFP)." Scientific Reports. 5, pp. 1-14. https://doi.org/10.1038/srep13644Biological control of sclerotinia stem rot of canola using antagonistic bacteria
Kamal, M. M., Lindbeck, K. D., Savocchia, S. and Ash, G. J.. 2015. "Biological control of sclerotinia stem rot of canola using antagonistic bacteria ." Plant Pathology. 64 (6), pp. 1375-1384. https://doi.org/10.1111/ppa.12369Biology and biocontrol of Sclerotinia sclerotiorum (Lib.) de Bary in oilseed Brassicas
Kamal, Mohd. Mostofa, Savocchia, Sandra, Lindbeck, Kurt D. and Ash, Gavin J.. 2016. "Biology and biocontrol of Sclerotinia sclerotiorum (Lib.) de Bary in oilseed Brassicas." Australasian Plant Pathology. 45 (1), pp. 1-14. https://doi.org/10.1007/s13313-015-0391-2Loop-mediated isothermal amplification for the detection of Pseudomonas fuscovaginae
Ash, G. J., Lang, J. M., Triplett, L. R., Stodart, B. J., Verdier, V. and Leach, J. E.. 2013. "Loop-mediated isothermal amplification for the detection of Pseudomonas fuscovaginae." 2013 APS-MSA Joint Meeting. United States 10 - 14 Aug 2013 United States. American Phytopathological Society.Phomentrioloxin: A Phytotoxic Pentasubstituted Geranylcyclohexentriol Produced by Phomopsis sp., a Potential Mycoherbicide for Carthamus lanatus Biocontrol
Cimmino, Alessio, Andolfi, Anna, Zonno, Maria C., Troise, Ciro, Santini, Antonello, Tuzi, Angela, Vurro, Maurizio, Ash, Gavin and Evidente, Antonio. 2012. "Phomentrioloxin: A Phytotoxic Pentasubstituted Geranylcyclohexentriol Produced by Phomopsis sp., a Potential Mycoherbicide for Carthamus lanatus Biocontrol." Journal of Natural Products. 75 (6), pp. 1130-1137. https://doi.org/10.1021/np300200jThe science, art and business of successful bioherbicides
Ash, G. J.. 2010. "The science, art and business of successful bioherbicides." Biological Control. 52 (3), pp. 230-240. https://doi.org/10.1016/j.biocontrol.2009.08.007The characterization and diversity of bacterial endophytes of grapevine
West, E. R., Cother, E. J., Steel, C. C. and Ash, G. J.. 2010. "The characterization and diversity of bacterial endophytes of grapevine." Canadian Journal of Microbiology. 56 (3), pp. 209-216. https://doi.org/10.1139/W10-004Australia and New Zealand biocontrol conference: Emerging themes, future prospects
Gurr, Geoff M.., Horne, Paul, Page, Jessica, Ash, Gavin J. and Pilkington, Leigh J.. 2010. "Australia and New Zealand biocontrol conference: Emerging themes, future prospects." Biological Control. 52 (3), pp. 195-197. https://doi.org/10.1016/j.biocontrol.2010.01.001Genotypic analysis of Mucor from the platypus in Australia
Connolly, J. H., Stodart, B. J. and Ash, G. J.. 2010. "Genotypic analysis of Mucor from the platypus in Australia." Journal of Wildlife Diseases. 46 (1), pp. 55-69. https://doi.org/10.7589/0090-3558-46.1.55Development of strain specific molecular markers for the Sclerotinia minor bioherbicide strain IMI 344141
Pan, L., Ash, G. J., Ahn, B. and Watson, A. K.. 2010. "Development of strain specific molecular markers for the Sclerotinia minor bioherbicide strain IMI 344141." Biocontrol Science and Technology. 20 (9), pp. 939-959. https://doi.org/10.1080/09583157.2010.491895Evidence that Diaporthe toxica infection of Lupinus albus is an emerging concern for the Australian lupin industry
Cowley, R. B., Ash, G. J., Harper, J. D. I. and Luckett, D. J.. 2010. "Evidence that Diaporthe toxica infection of Lupinus albus is an emerging concern for the Australian lupin industry." Australasian Plant Pathology. 39 (2), pp. 146-153. https://doi.org/10.1071/AP09067Physiological characterization of the dandelion bioherbicide, Sclerotinia minor IMI 344141
Shaheen, In'aam Y., Abu-Dieyeh, Mohammed H., Ash, Gavin J. and Watson, Alan K.. 2010. "Physiological characterization of the dandelion bioherbicide, Sclerotinia minor IMI 344141." Biocontrol Science and Technology. 20 (1), pp. 57-76. https://doi.org/10.1080/09583150903419520Influence of cultural and environmental conditions on conidial production, conidial germination and infectivity of Rhynchosporium alismatis, a candidate mycoherbicide
Jahromi, F. G., Ash, G. J. and Cother, E. J.. 1998. "Influence of cultural and environmental conditions on conidial production, conidial germination and infectivity of Rhynchosporium alismatis, a candidate mycoherbicide." Australasian Plant Pathology. 27 (3), pp. 180-185. https://doi.org/10.1071/AP98020Suppressive effects of Rhynchosporium alismatis on different growth stages of Damasonium minus
Jahromi, F. G., Ash, G. J., Cother, E. J. and SOC ESPANOLA MALHERBOLOGIA. 1997. "Suppressive effects of Rhynchosporium alismatis on different growth stages of Damasonium minus." 1997 Congress of the Sociedad-Espanola-de-Malherbologia. Spain 24 - 26 Nov 1997 Spain.Phomopsis spp. associated with die-back of saffron thistle (Carthamus lanatus)
Crump, N. S., Ash, G. J. and Nikandrow, A.. 1996. "Phomopsis spp. associated with die-back of saffron thistle (Carthamus lanatus)." Australasian Plant Pathology. 25 (2), p. 143. https://doi.org/10.1071/AP96025Effect of Post-Inoculation Temperature and Light Intensity on Expression of Resistance to Stripe Rust in Some Australian Wheat Cultivars
Ash, G. J. and Rees, R. G.. 1994. "Effect of Post-Inoculation Temperature and Light Intensity on Expression of Resistance to Stripe Rust in Some Australian Wheat Cultivars." Australian Journal of Agricultural Research. 45 (7), pp. 1379-1386. https://doi.org/10.1071/AR9941379Effects of temperature on the response of some Australian wheat cultivars to Puccinia striiformis f. sp. tritici
Park, Robert F., Ash, Gavin J. and Rees, Robert G.. 1992. "Effects of temperature on the response of some Australian wheat cultivars to Puccinia striiformis f. sp. tritici." Mycological Research. 96 (3), pp. 166-170. https://doi.org/10.1016/S0953-7562(09)80961-1Yield losses in wheat caused by stripe rust (Puccinia striiformis West.) in northern New South Wales
Ash, G J.. and Brown, J. F.. 1990. "Yield losses in wheat caused by stripe rust (Puccinia striiformis West.) in northern New South Wales." Australian Journal of Experimental Agriculture. 30 (1), pp. 103-108. https://doi.org/10.1071/EA9900103This item comprises data from the following sources: Web of Science