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Background: Genus Trichoderma of fungal kingdom are largely used as biological control agents due to broad-spectrum activity against plant pathogens. Objective: This study aimed to investigate Trichoderma harzianum, an endophytic fungus obtained from ginger (Zingiber officinale) leaves. Methods: The chemical structures of the isolated compounds were deduced on the basis of UV, 1H NMR and MS data analyses, as well as comparison with literature. Results: Two known tetramic acid derivatives were isolated from this fungus, including harzianic acid (A) and isoharzianic acid (B). Compound B inhibited the growth of a corn pathogenic fungus, Ustilago maydis, with inhibition zone diameter (39 ± 0.33 mm) larger than nystatin (29 mm). Additionally, iso-HA (B) revealed antibacterial effect towards Staphylococcus aureus with MIC value of 25 µM. However, both compounds showed no cytotoxicity against human cervical and ovarian cancer cell lines. Conclusion: T. harzianum produced antimicrobial compound like iso-HA which has potential application either in agricultural or health.

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.

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. [ABSTRACT FROM AUTHOR]