Planta Med 2019; 85(01): 62-71
DOI: 10.1055/a-0654-5850
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

José Rivera-Chávez
1  Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
6  Current address: Department of Natural Products, Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
,
Tamam El-Elimat
2  Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid, Jordan
,
Jacklyn M. Gallagher
1  Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
,
Tyler N. Graf
1  Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
,
Jacques Fournier
3  Los Muros, Rimont, France
,
Gati K. Panigrahi
4  Department of Cancer Biology and Comprehensive Cancer Center, Wake Forest Baptist Medical Center & Wake Forest School of Medicine, Winston-Salem, North Carolina, USA
,
Gagan Deep
4  Department of Cancer Biology and Comprehensive Cancer Center, Wake Forest Baptist Medical Center & Wake Forest School of Medicine, Winston-Salem, North Carolina, USA
,
Rick L. Bunch
5  Department of Geography, Environment, and Sustainability, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
,
Huzefa A. Raja
1  Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
,
Nicholas H. Oberlies
1  Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
› Author Affiliations
Further Information

Publication History

received 28 March 2018
revised 15 June 2018

accepted 29 June 2018

Publication Date:
17 July 2018 (online)

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 α-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 15G256ε (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 Mosherʼs 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.

Supporting Information