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Planta Med 2023; 89(12): 1178-1189
DOI: 10.1055/a-2063-5481
Natural Product Chemistry and Analytical Studies
Original Papers

Paecilins Q and R: Antifungal Chromanones Produced by the Endophytic Fungus Pseudofusicoccum stromaticum CMRP4328

Jucélia Iantas‡
1   Postgraduate Program in Microbiology, Department of Pathology, Federal University of Paraná (UFPR), Curitiba, Brazil
2   Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
3   Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Kentucky, United States
,
Daiani Cristina Savi
4   Postgraduate Program in Genetics, Department of Genetics, Federal University of Paraná (UFPR), Curitiba, Brazil
5   Department of Biomedicine, Centro Universitário Católica de Santa Catarina, Joinville, Brazil
,
Larissa V. Ponomareva
2   Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
3   Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Kentucky, United States
,
Jon S. Thorson
2   Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
3   Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Kentucky, United States
,
Jürgen Rohr
2   Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
,
Chirlei Glienke
1   Postgraduate Program in Microbiology, Department of Pathology, Federal University of Paraná (UFPR), Curitiba, Brazil
4   Postgraduate Program in Genetics, Department of Genetics, Federal University of Paraná (UFPR), Curitiba, Brazil
,
Khaled A. Shaaban  ‡
2   Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, United States
3   Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Kentucky, United States
› Author AffiliationsSupported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico 309971/2016-0
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico 424738/2016-3
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico INCT Citrus 465440/2014-2
Supported by: Center of Biomedical Research Excellence (COBRE) in Pharmaceutical Research and Innovation CPRI, NIH P20 GM130456
Supported by: National Center for Advancing Translational Sciences UL1TR000117
Supported by: National Center for Advancing Translational Sciences UL1TR001998
Supported by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior 001
Supported by: National Institutes of Health R01 CA243529
Supported by: National Institutes of Health R01 GM115261
› Further Information
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Abstract

Chemical investigation of the endophyte Pseudofusicoccum stromaticum CMRP4328 isolated from the medicinal plant Stryphnodendron adstringens yielded ten compounds, including two new dihydrochromones, paecilins Q (1) and R (2). The antifungal activity of the isolated metabolites was assessed against an important citrus pathogen, Phyllosticta citricarpa. Cytochalasin H (6) (78.3%), phomoxanthone A (3) (70.2%), phomoxanthone B (4) (63.1%), and paecilin Q (1) (50.5%) decreased in vitro the number of pycnidia produced by P. citricarpa, which are responsible for the disease dissemination in orchards. In addition, compounds 3 and 6 inhibited the development of citrus black spot symptoms in citrus fruits. Cytochalasin H (6) and one of the new compounds, paecilin Q (1), appear particularly promising, as they showed strong activity against this citrus pathogen, and low or no cytotoxic activity. The strain CMRP4328 of P. stromaticum and its metabolites deserve further investigation for the control of citrus black spot disease.

Key words

Pseudofusicoccum stromaticum - Phyllosticta citricarpa - Stryphnodendron adstringens - fungal metabolites - dihydrochromones - phytopathogenic fungi

Supporting Information

    General experimental procedures, cancer cell line viability assay, physicochemical properties of compounds 3 – 10, workup scheme for compound isolation, UV-vis spectra of compounds 1 – 5, chemical structures of compounds 11 – 13, antifungal activity of compounds 2, 5, and 7 – 10, 1H,1H-COSY, TOCSY, HMBC, and NOESY correlations of compounds 6 – 10, HPLC/UV, HPLC/MS, HRMS and NMR spectra of all isolated compounds are available as Supporting Information.

  • Supporting Information


Publication History

Received: 01 November 2022

Accepted after revision: 23 March 2023

Accepted Manuscript online:
28 March 2023

Article published online:
28 June 2023

© 2023. Thieme. All rights reserved.

Georg Thieme Verlag KG
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