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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Media type:
E-Article
Title:
Sheptide A: an antimalarial cyclic pentapeptide from a fungal strain in the Herpotrichiellaceae
Contributor:
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.
Published:
Springer Science and Business Media LLC, 2023
Published in:
The Journal of Antibiotics, 76 (2023) 11, Seite 642-649
Description:
AbstractAs part of ongoing efforts to isolate biologically active fungal metabolites, a cyclic pentapeptide, sheptide A (1), was discovered from strain MSX53339 (Herpotrichiellaceae). The structure and sequence of 1 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, 1 displayed a pEC50 value of 5.75 ± 0.49 against malaria-causing Plasmodium falciparum. Compound 1 was also tested in a counter screen for general cytotoxicity against human hepatocellular carcinoma (HepG2), yielding a pCC50 value of 5.01 ± 0.45 and indicating a selectivity factor of ~6. This makes 1 the third known cyclic pentapeptide biosynthesized by fungi with antimalarial activity.