Citrus black spot (CBS) and post-bloom fruit drop (PFD), caused by Phyllosticta citricarpa and Colletotrichum abscissum, respectively, are two important citrus diseases worldwide. CBS depreciates the market value and prevents exportation of citrus fruits to Europe. PFD under favorable climatic conditions can cause the abscission of flowers, thereby reducing citrus production by 80%. An ecofriendly alternative to control plant diseases is the use of endophytic microorganisms, or secondary metabolites produced by them. Strain LGMF1631, close related to Diaporthe cf. heveae 1, was isolated from the medicinal plant Stryphnodendron adstringens and showed significant antimicrobial activity, in a previous study. In view of the potential presented by strain LGMF1631, and the absence of chemical data for secondary metabolites produced by D. cf. heveae, we decided to characterize the compounds produced by strain LGMF1631. Based on ITS, TEF1, and TUB phylogenetic analysis, strain LGMF1631 was confirmed to belong to D. cf. heveae 1. Chemical assessment of the fungal strain LGMF1631 revealed one new seco-dihydroisocoumarin [cladosporin B (1)] along with six other related, already known dihydroisocoumarin derivatives and one monoterpene [(-)-(1S,2R,3S,4R)-p-menthane-1,2,3-triol (8)]. Among the isolated metabolites, compound 5 drastically reduced the growth of both phytopathogens in vitro and completely inhibited the development of CBS and PFD in citrus fruits and flowers. In addition, compound 5 did not show toxicity against human cancer cell lines or citrus leaves, at concentrations higher than used for the inhibition of the phytopathogens, suggesting the potential use of (-)-(3R,4R)-cis-4-hydroxy-5-methylmellein (5) to control citrus diseases.

Department of Genetics Universidade Federal do Parana Av Coronel Francisco Heráclito dos Santos 210 Curitiba PR 81531 970 Brazil

Department of Genetics Universidade Federal do Parana Av Coronel Francisco Heráclito dos Santos 210 Curitiba PR 81531 970 Brazil Department of Pharmaceutical Sciences College of Pharmacy University of Kentuck Lexington KY 40536 USA

Department of Pathology Universidade Federal do Parana Av Coronel Francisco Heráclito dos Santos 210 Curitiba PR 81531 970 Brazil

Department of Pharmaceutical Sciences College of Pharmacy University of Kentuck Lexington KY 40536 USA

Department of Pharmaceutical Sciences College of Pharmacy University of Kentuck Lexington KY 40536 USA Center for Pharmaceutical Research and Innovation College of Pharmacy University of Kentucky Lexington KY 40536 USA

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