519
Views
21
CrossRef citations to date
0
Altmetric
Plant Pathogens

Secondary metabolites produced by grapevine strains of Lasiodiplodia theobromae grown at two different temperatures

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 466-476 | Received 19 Oct 2018, Accepted 25 Mar 2019, Published online: 26 Apr 2019

LITERARURE CITED

  • Albuquerque P, Casadevall A. 2012. Quorum sensing in fungi−a review. Medical Mycology 50:337−345.
  • Aldridge DC, Galt S, Giles D, Turner WB. 1971. Metabolites of Lasiodiplodia theobromae. Journal of the Chemical Society C 1623–1627.
  • Ammerman NC, Beier-Sexton M, Azad AF. 2008. Growth and maintenance of vero cell lines. Current Protocols in Microbiology S1: A.4E.1–A.4E.7.
  • Andolfi A, Basso S, Giambra S, Conigliano G, Lo Piccolo S, Alves A, Burruano S. 2016. Lasiolactols A and B produced by the grapevine fungal pathogen Lasiodiplodia mediterranea. Chemistry & Biodiversity 13:395–402.
  • Andolfi A, Maddau L, Cimmino A, Linaldeddu BT, Basso S, Deidda A, Serra S, Evidente A. 2014. Lasiojasmonates A–C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen. Phytochemistry 103:145–153.
  • Andolfi A, Maddau L, Cimmino A, Linaldeddu BT, Franceschini A, Serra S, Basso S, Melck D, Evidente A. 2012. Cyclobotryoxide, a phytotoxic metabolite produced by the plurivorous pathogen Neofusicoccum australe. Journal of Natural Products 75:1785–1791.
  • Andolfi A, Mugnai L, Luque J, Surico G, Cimmino A, Evidente A. 2011. Phytotoxins produced by fungi associated with grapevine trunk diseases. Toxins 3:1569–1605.
  • Auger J, Esterio M, Ricke G, Pérez I. 2004. Black dead arm and basal canker of Vitis vinifera cv. Red Globe caused by Botryosphaeria obtusa in Chile. Plant Disease 88: 1286.
  • Cabras A, Mannoni MA, Serra S, Andolfi A, Fiore M, Evidente A. 2006. Occurrence, isolation and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic fungus of Pinus radiata. European Journal of Plant Pathology 115:187–193.
  • Capasso R, Cristinzio G, Evidente A, Scognamiglio F. 1992. Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochemistry 31:4125–4128.
  • Carvajal M, Espinoza L, Caggia S, Cardile V, Garbarino JA, Peña-Cortés H, Russo A. 2011. New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells. Electronic Journal of Biotechnology 14:7.
  • Chanclud E, Morel JB. 2016. Plant hormones: a fungal point of view. Molecular Plant Pathology 17:1289–1297.
  • D’Souza AD, Ramesh M. 2002. Senescence in fungi. Resonance 7:51–55.
  • da Cunha MAA, Turmina, JA, Ivanov RC, Barroso RR, Marques PT, Fonseca EAI, Fortes ZB, Dekker RFH, Khaper N, Barbosa AM. 2012. Lasiodiplodan, an exocellular (1-6)-β-D-glucan from Lasiodiplodia theobromae MMPI: production on glucose, fermentation kinetics, rheology and anti-proliferative activity. Journal of Industrial Microbiology and Biotechnology 39:1179–1188.
  • De Buyck L, Forzato C, Ghelfi F, Mucci A, Nitti P, Pagnoni UM, Parsons AF, Pitacco G, Roncaglia F. 2006. A new and effective route to (+/−)-botryodiplodin and (+/−)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization. Tetrahedron Letters 47:7759–7762.
  • Dias M, Souza DS. 1998. Principais doenças da videira. Informe Agropecuário, Belo Horizonte 194:76–84.
  • Dimitriadis C, Gill M, Harte MF. 1997. The first stereospecific approach to both enantiomers of mellein. Tetrahedron: Asymmetry 8:2153–2158.
  • Duarte AS, Cavaleiro E, Pereira C, Merino S, Esteves AC, Duarte EP, Tomás JM, Correia AC. 2015. Aeromonas piscicola AH-3 expresses an extracellular collagenase with cytotoxic properties. Letters in Applied Microbiology 60:288–297.
  • Dzoyem JP, Melong R, Tsamo AT, Maffo T, Kapche DG, Ngadjui BT, McGaw LJ, Eloff JN. 2017. Cytotoxicity, antioxidant and antibacterial activity of four compounds produced by an endophytic fungus Epicoccum nigrum associated with Entada abyssinica. Revista Brasileira de Farmacognosia 27:251–253.
  • Félix C, Duarte AS, Vitorino R, Guerreiro AC, Domingues P, Correia AC, Alves A, Esteves AC. 2016. Temperature modulates the secretome of the phytopathogenic fungus Lasiodiplodia theobromae. Frontiers in Plant Sciences 7:1096.
  • Félix C, Salvatore MM, DellaGreca M, Meneses R, Duarte AS, Salvatore F, Naviglio D, Gallo M, Jorrín-Novo JV, Alves A, Andolfi A, Esteves AC. 2018. Production of toxic metabolites by two strains of Lasiodiplodia theobromae, isolated from coconut tree and human patient. Mycologia 110:642–653.
  • Forzato C, Furlan G, Nitti P, Pitacco G, Marchesan D, Coriani S, Valentin E. 2005. A combined experimental and computational strategy in the assignment of absolute configurations of 4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acids and their esters. Tetrahedron: Asymmetry 16:3011–3023.
  • Guida M, Salvatore MM, Salvatore F. 2015. A Strategy for GC/MS quantification of polar compounds via their silylated surrogates: silylation and quantification of biological amino acids. Journal of Analytical and Bioanalytical Techniques 6:263–279.
  • Husain A, Ahmad A, Agrawal PK. 1993. (−)-Jasmonic acid, a phytotoxic substance from Botryodiplodia theobromae: characterization by NMR spectroscopic methods. Journal of Natural Products 56:2008–2011.
  • Jami F, Slippers B, Wingfield MJ, Gryzenhout M. 2013. Greater Botryosphaeriaceae diversity in healthy than associated diseased Acacia karroo tree tissues. Australasian Plant Pathology 42:421–430.
  • Kitaoka N, Nabeta K, Matsuura H. 2009. Isolation and structural elucidation of a new cyclohexenone compound from Lasiodiplodia theobromae. Bioscience, Biotechnology, and Biochemistry 73:1890–1892.
  • Masi M, Cimmino A, Reveglia P, Mugnai L, Surico G, Evidente A. 2018. Advances on fungal phytotoxins and their role in grapevine trunk diseases. Journal of Agricultural and Food Chemistry 66:5948–5958.
  • Miranda CCBO, Dekker RFH, Serpeloni JM, Fonseca EAI, Cólus, IMS, Barbosa AM. 2008. Anticlastogenic activity exhibited by botryosphaeran, a new exopolysaccharide produced by Botryosphaeria rhodina MAMB-05. International Journal of Biological Macromolecules 42:172–177.
  • Moreau S, Lablache-Combier A, Biguet J, Foulon C, Delfosse M. 1982. Botryodiplodin, a mycotoxin synthesized by a strain of P. roqueforti. The Journal of Organic Chemistry 47:2358–2359.
  • Nouguier R, Gastaldi S, Stien D, Bertrand M, Villar F, Andrey O, Renaud P. 2003. Synthesis of (±)- and (−)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals. Tetrahedron: Asymmetry 14:3005–3018.
  • Pandi M, Manikandan R, Muthumary J. 2010. Anticancer activity of fungal taxol derived from Botryodiplodia theobromae Pat., an endophytic fungus, against 7,12-dimethyl benz(a)anthracene (DMBA)-induced mammary gland carcinogenesis in Sprague Dawley rats. Biomedicine & Pharmacotherapy 64:48–53.
  • Paolinelli-Alfonso M, Villalobos-Escobedo JM, Rolshausen P, Herrera-Estrella A, Galindo-Sánchez C, López-Hernández J, Hernandez-Martinez R. 2016. Global transcriptional analysis suggests Lasiodiplodia theobromae pathogenicity factors involved in modulation of grapevine defensive response. BMC Genomics 17:615.
  • Phillips AJL. 2002. Botryosphaeria species associated with diseases of grapevines in Portugal. Phytopathologia Mediterranea 41:3–18.
  • Pitt WM, Huang R, Steel CC, Savocchia S. 2010. Identification, distribution and current taxonomy of Botryosphaeriaceae species associated with grapevine decline in New South Wales and South Australia. Australian Journal of Grape and Wine Research 16:258–271.
  • Qian CD, Fu YH, Jiang FS, Xu ZH, Cheng DQ, Ding B, Gao CX, Ding ZS. 2014. Lasiodiplodia sp. ME4-2, an endophytic fungus from the floral parts of Viscum coloratum, produces indole-3-carboxylic acid and other aromatic metabolites. BMC Microbiology 14: 297.
  • Ramezani M, Shier WT, Abbas H K, Tonos JL, Baird RE, Sciumbato GL. 2007. Soybean charcoal rot disease fungus Macrophomina phaseolina in Mississippi produces the phytotoxin (−)-botryodiplodin but no detectable phaseolinone. Journal of Natural Products 70:128–129.
  • Ravi BN, Armstrong RW, Faulkner DJ. 1979. Some aromatic compounds from the marine sponge Plakortis halichondrioides. The Journal of Organic Chemistry 44:3109–3113.
  • Rehnberg N, Magnusson G. 1990. Total synthesis of (−)- and (+)-botryodiplodin and (+)- and (−)-epibotryodiplodin. Acta Chemica Scandinavica 44:377–383.
  • Rodriguez-Galvez E, Maldonado E, Alves A. 2015. Identification and pathogenicity of Lasiodiplodia theobromae causing dieback of table grapes in Peru. European Journal of Plant Pathology 141:477–489.
  • Saeed A. 2016. Isocoumarins, miraculous natural products blessed with diverse pharmacological activities. European Journal of Medicinal Chemistry 116:290–317.
  • Saha S, Sengupta J, Banerjee D, Khetan A. 2012. Lasiodiplodia theobromae keratitis: a case report and review of literature. Mycopathologia 174:335–339.
  • Sakai K, Amemiya S, Inoue K, Kojima K. 1979. The conversion of methylenomycin A to natural botryodiplodin and their absolute configurations. Tetrahedron Letters 20:2365–2368.
  • Salvatore MM, DellaGreca M, Nicoletti R, Salvatore F, Vinale F, Naviglio D, Andolfi A. 2018a. Talarodiolide, a new 12-membered macrodiolide, and GC/MS investigation of culture filtrate and mycelial extracts of Talaromyces pinophilus. Molecules 23:950.
  • Salvatore, MM, Nicoletti, R, Salvatore, F, Naviglio, D, Andolfi, A. 2018b. GC–MS approaches for the screening of metabolites produced by marine-derived Aspergillus. Marine Chemistry, doi:10.1016/j.marchem.2018.08.003
  • Savocchia S, Steel CC, Stodart BJ, Somers A. 2007. Pathogenicity of Botryosphaeria species isolated from declining grapevines in subtropical regions of Eastern Australia. Vitis 46:27–32.
  • Spagnolo A, Mondello V, Larignon P, Villaume S, Rabenoelina F, Clément C, Fontaine F. 2017. Defence responses in grapevine (cv. Mourvèdre) after inoculation with the botryosphaeria dieback pathogens Neofusicoccum parvum and Diplodia seriata and their relationship with flowering. International Journal of Molecular Sciences 18:393.
  • Úrbez-Torres JR, Leavitt GM, Voegel TM, Gubler WD. 2006. Identification and distribution of Botryosphaeria spp. associated with grapevine cankers in California. Plant Disease 90:1490–1503.
  • Úrbez-Torres JR, Leavitt GM, Guerrero JC, Guevara J, Gubler WD. 2008. Identification and pathogenicity of Lasiodiplodia theobromae and Diplodia seriata, the causal agents of bot canker disease of grapevines in Mexico. Plant Disease 92:519–529.
  • Úrbez-Torres JR, Gubler WD. 2009. Pathogenicity of Botryosphaeriaceae species isolated from grapevine cankers in California. Plant Disease 93:584–592.
  • Úrbez-Torres JR. 2011. The status of Botryosphaeriaceae species infecting grapevine. Phytopathologia Mediterranea 50:S5–S45.
  • Van Niekerk JM, Crous PW, Groenewald JZ, Fourie PH, Halleen F. 2004. DNA phylogeny, morphology and pathogenicity of botryosphaeria species on grapevines. Mycologia 96:781–798. doi:10.1080/15572536.2005.11832926
  • Van Niekerk JM, Fourie PH, Halleen F, Crous PW. 2006. Botryosphaeria spp. as grapevine trunk disease pathogens. Phytopathologia Mediterranea 45:S43–S54.
  • Yang Q, Asai, M, Matsuura H, Yoshihara T. 2000. Potato micro-tuber inducing hydroxylasiodiplodins from Lasiodiplodia theobromae. Phytochemistry 54:489– 494.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.