title: A novel fungal metabolite with beneficial properties for agricultural applications.
abstract: Trichoderma are ubiquitous soil fungi that include species widely used as biocontrol agents in agriculture. Many isolates are known to secrete several secondary metabolites with different biological activities towards plants and other microbes. Harzianic acid (HA) is a T. harzianum metabolite able to promote plant growth and strongly bind iron. In this work, we isolated from the culture filtrate of a T. harzianum strain a new metabolite, named isoharzianic acid (iso-HA), a stereoisomer of HA. The structure and absolute configuration of this compound has been determined by spectroscopic methods, including UV-Vis, MS, 1D and 2D NMR analyses. In vitro applications of iso-HA inhibited the mycelium radial growth of Sclerotinia sclerotiorum and Rhizoctonia solani. Moreover, iso HA improved the germination of tomato seeds and induced disease resistance. HPLC-DAD experiments showed that the production of HA and iso HA was affected by the presence of plant tissue in the liquid medium. In particular, tomato tissue elicited the production of HA but negatively modulated the biosynthesis of its analogue iso-HA, suggesting that different forms of the same Trichoderma secondary metabolite have specific roles in the molecular mechanism regulating the Trichoderma plant interaction.
authors.affiliation: Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy. f.vinale@ipp.cnr.it.
authors.forename: Francesco
authors.initials: F
authors.lastname: Vinale
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Gelsomina
authors.initials: G
authors.lastname: Manganiello
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Nigro
authors.affiliation: Centro Interdipartimentale di Spettroscopia di Risonanza Magnetica Nucleare (CERMANU), Università degli Studi di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Pierluigi
authors.initials: P
authors.lastname: Mazzei
authors.affiliation: Centro Interdipartimentale di Spettroscopia di Risonanza Magnetica Nucleare (CERMANU), Università degli Studi di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Piccolo
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Pascale
authors.affiliation: Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy.
authors.forename: Michelina
authors.initials: M
authors.lastname: Ruocco
authors.affiliation: Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Marra
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Nadia
authors.initials: N
authors.lastname: Lombardi
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Stefania
authors.initials: S
authors.lastname: Lanzuise
authors.affiliation: Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy.
authors.forename: Rosaria
authors.initials: R
authors.lastname: Varlese
authors.affiliation: Dipartimento di Fisica, Università di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy.
authors.forename: Pierpaolo
authors.initials: P
authors.lastname: Cavallo
authors.affiliation: Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy.
authors.forename: Matteo
authors.initials: M
authors.lastname: Lorito
authors.affiliation: Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy.
authors.forename: Sheridan L
authors.initials: SL
authors.lastname: Woo
mesh_terms: D000383:Agriculture; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry / Q000378:metabolism*; D018525:Germination / Q000187:drug effects; D006885:Hydroxybutyrates / Q000737:chemistry / Q000378:metabolism; D018551:Solanum lycopersicum / Q000254:growth & development; D055432:Metabolomics; D010572:Pest Control, Biological; D010937:Plant Growth Regulators / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011758:Pyrroles / Q000737:chemistry / Q000378:metabolism; D064210:Secondary Metabolism; D012988:Soil Microbiology; D014242:Trichoderma / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D006885:Hydroxybutyrates; D010937:Plant Growth Regulators; D011758:Pyrroles; C088506:harzianic acid