Planta Med 2010; 76 - P48
DOI: 10.1055/s-0030-1251810

Bioactive 1,4-Dihydroxy-5-phenyl-2-pyridinone Alkaloids from Septoria pistaciarum (Ascomycetes)

M Kumarihamy 1, 2, FR Fronczek 3, D Ferreira 1, 2, MR Jacob 1, SI Khan 1, NPD Nanayakkara 1
  • 1National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, Mississippi 38677
  • 2Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677
  • 3Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803

Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids (1–4) were isolated from an EtOAc extract of a culture medium of Septoria pistaciarum, the causative agent for Septoria leaf and fruit spot disease of pistachio (Pistachia vera) in the US[1] and Mediterranean[2] countries. The structures of these compounds were determined by spectroscopic methods, and the absolute configuration of the major compound 1 by X-ray crystallographic analysis. Compound 1 exhibited moderate in vitro antimalarial activities against chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum and cytotoxic activity to Vero cells. Compound 2 was moderately active against both methicillin-sensitive and methicillin-resistant Staphylococcus aureus.

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Acknowledgements: This work was supported by the National Institutes of Health (R21 A1061431–01) and in part by the United States Department of Agriculture, ARS, Specific Cooperative Agreement No. 58–6408–2-009. The authors sincerely thank Dr. Bharathi Avula and Mr. Frank T. Wiggers for recording the MS and 1H NMR spectra, and Ms. Marsha Wright and Mr. John Trott for biological testing. References: [1] Young DJ, Michailides TJ (1989) Plant Disease, 73: 775. [2] Eskalen A, Küsek M, et al. (1999) Fungal Diseases in Pistachio Trees in East-Mediterranean and Southeast Anatolian Regions. 11 GREMPA Seminar on Pistachios and Almonds, Sanliurfa (Turkey), 1–4 Sep 1999. Publication located at http://ressources.ciheam.org/om/pdf/c56/01600187.pdf.