Shepherd, Robert A.;
Earp, Cody E.;
Cank, Kristof B.;
Raja, Huzefa A.;
Burdette, Joanna;
Maher, Steven P.;
Marin, Adriana A.;
Ruberto, Anthony A.;
Mai, Sarah Lee;
Darveaux, Blaise A.;
Kyle, Dennis E.;
Pearce, Cedric J.;
Oberlies, Nicholas H.
Sheptide A: an antimalarial cyclic pentapeptide from a fungal strain in the Herpotrichiellaceae
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Medientyp:
E-Artikel
Titel:
Sheptide A: an antimalarial cyclic pentapeptide from a fungal strain in the Herpotrichiellaceae
Beteiligte:
Shepherd, Robert A.;
Earp, Cody E.;
Cank, Kristof B.;
Raja, Huzefa A.;
Burdette, Joanna;
Maher, Steven P.;
Marin, Adriana A.;
Ruberto, Anthony A.;
Mai, Sarah Lee;
Darveaux, Blaise A.;
Kyle, Dennis E.;
Pearce, Cedric J.;
Oberlies, Nicholas H.
Erschienen:
Springer Science and Business Media LLC, 2023
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>As part of ongoing efforts to isolate biologically active fungal metabolites, a cyclic pentapeptide, sheptide A (<jats:bold>1</jats:bold>), was discovered from strain MSX53339 (<jats:italic>Herpotrichiellaceae</jats:italic>). The structure and sequence of <jats:bold>1</jats:bold> were determined primarily by analysis of 2D NMR and HRMS/MS data, while the absolute configuration was assigned using a modified version of Marfey’s method. In an in vitro assay for antimalarial potency, <jats:bold>1</jats:bold> displayed a pEC<jats:sub>50</jats:sub> value of 5.75 ± 0.49 against malaria-causing <jats:italic>Plasmodium falciparum</jats:italic>. Compound <jats:bold>1</jats:bold> was also tested in a counter screen for general cytotoxicity against human hepatocellular carcinoma (HepG2), yielding a pCC<jats:sub>50</jats:sub> value of 5.01 ± 0.45 and indicating a selectivity factor of ~6. This makes <jats:bold>1</jats:bold> the third known cyclic pentapeptide biosynthesized by fungi with antimalarial activity.</jats:p>