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Molecules 2014, 19(7), 9760-9772; doi:10.3390/molecules19079760

A Novel Fungal Metabolite with Beneficial Properties for Agricultural Applications

1
Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche, via Università 133, 80055 Portici, Italy
2
Dipartimento di Agraria, Università di Napoli 'Federico II', Portici, 80055 Naples, Italy
3
Centro Interdipartimentale di Spettroscopia di Risonanza Magnetica Nucleare (CERMANU), Università degli Studi di Napoli 'Federico II', Portici, 80055 Naples, Italy
4
Dipartimento di Fisica, Università di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 5 March 2014 / Revised: 26 June 2014 / Accepted: 1 July 2014 / Published: 8 July 2014
(This article belongs to the Section Metabolites)
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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. View Full-Text
Keywords: Trichoderma; secondary metabolites; isoharzianic acid; harzianic acid; plant growth promotion; disease resistance Trichoderma; secondary metabolites; isoharzianic acid; harzianic acid; plant growth promotion; disease resistance
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MDPI and ACS Style

Vinale, F.; Manganiello, G.; Nigro, M.; Mazzei, P.; Piccolo, A.; Pascale, A.; Ruocco, M.; Marra, R.; Lombardi, N.; Lanzuise, S.; Varlese, R.; Cavallo, P.; Lorito, M.; Woo, S.L. A Novel Fungal Metabolite with Beneficial Properties for Agricultural Applications. Molecules 2014, 19, 9760-9772.

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