Delitpyrones: a-Pyrone Derivatives from a Freshwater Delitschia sp.

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Rick L. Bunch, Professor and Director of Center for GIScience (Creator)
Tyler Graf, Research Scientist (Creator)
Nicholas Oberlies, Patricia A. Sullivan Distinguished Professor of Chemistry (Creator)
Huzefa A. Raja, Postdoctoral Fellow (Creator)
Institution
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/

Abstract: In research focused on the discovery of new chemical diversity from freshwater fungi, a peak library was built and evaluated against a prostate cancer cell line, E006AA-hT, which was derived from an African American, as this population is disproportionately affected by prostate cancer. The chemical study of the bioactive sample accessioned as G858 (Delitschia sp.) led to the isolation of eight new a-pyrone derivatives (1?–?7, and 11), as well as the new 3S*,4S*-7-ethyl-4,8-dihydroxy-3,6-dimethoxy-3,4-dihydronaphthalen-1(2H)-one (15). In addition, the known compounds 5-(3-S-hydroxybutyl)-4-methoxy-6-methyl-2H-pyran-2-one (8), 5-(3-oxobutyl)-4-methoxy-6-methyl-2H-pyran-2-one (9), pyrenocine I (10), 5-butyl-6-(hydroxymethyl)-4-methoxy-2H-pyran-2-one (12), sporidesmin A (13), 6-ethyl-2,7-dimethoxyjuglone (14), artrichitin (16), and lipopeptide 15G256e (17) were also obtained. The structures of the new compounds were elucidated using a set of spectroscopic (NMR) and spectrometric (HRMS) methods. The absolute configuration of the most abundant member of each subclass of compounds was assigned through a modified Mosher's ester method. For 15, the relative configuration was assigned based on analysis of 3 J values. Compounds 1, 2, 5?–?14, 16, and 17 were evaluated against the cancer cell line E006AA-hT under hypoxic conditions, where compound 13 inhibited cell proliferation at a concentration of 2.5?µM.

Additional Information

Publication
Planta Medica. 85(1): 62 – 71.
Language: English
Date: 2018
Keywords
peak library, prostate cancer, cell proliferation, freshwater fungi, delitpyrones, Delitschia sp.

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