Antileukemic α-pyrone derivatives from the endophytic fungus Alternaria phragmospora

Ahmed M Metwaly; Frank R Fronczek; Guoyi Ma; Hazem A Kadry; Atef A El-Hela; Abd-Elsalam I Mohammad; Stephen J Cutler; Samir A Ross

doi:10.1016/j.tetlet.2014.04.085

Antileukemic α-pyrone derivatives from the endophytic fungus Alternaria phragmospora

Tetrahedron Lett. 2014 Jun 11;55(24):3478-3481. doi: 10.1016/j.tetlet.2014.04.085.

Authors

Ahmed M Metwaly¹, Frank R Fronczek², Guoyi Ma³, Hazem A Kadry⁴, Atef A El-Hela⁴, Abd-Elsalam I Mohammad⁴, Stephen J Cutler⁵, Samir A Ross⁶

Affiliations

¹ National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Department of Pharmacognosy, Faculty of Pharmacy, University of Al-Azhar, Cairo, Egypt.
² Department of Chemistry, College of Science, Louisiana State University, Baton Rouge, LA 70803, USA.
³ National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
⁴ Department of Pharmacognosy, Faculty of Pharmacy, University of Al-Azhar, Cairo, Egypt.
⁵ National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
⁶ National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.

Abstract

Four new (1-4) and two known (5 and 6) α-pyrone derivatives have been isolated from Alternaria phragmospora, an endophytic fungus from Vinca rosea, leaves. The isolated compounds were chemically identified to be 5-butyl-4-methoxy-6-methyl-2H-pyran-2-one (1), 5-butyl-6-(hydroxymethyl)-4-methoxy-2H-pyran-2-one (2), 5-(1-hydroxybutyl)-4-methoxy-6-methyl-2H-pyran-2-one (3), 4-methoxy-6-methyl-5-(3-oxobutyl)-2H-pyran-2-one (4), 5-(2-hydroxyethyl)-4-methoxy-6-methyl-2H-pyran-2-one (5), and 5-[(2E)-but-2-en-1-yl]-4-methoxy-6-methyl-2H-pyran-2-one (6). Compounds 2 and 4 showed moderate antileukemic activities against HL60 cells with IC₅₀ values of 2.2 and 0.9 μM and against K562 cells with IC₅₀ values of 4.5 and 1.5 μM, respectively.

Keywords: Alternaria phragmospora; Antileukemic; Endophytic fungi; α-Pyrone derivatives.

Abstract

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