title: Greensporones: resorcylic acid lactones from an aquatic Halenospora sp.
abstract: Fourteen new resorcylic acid lactones (1-14) were isolated from an organic extract of a culture of a freshwater aquatic fungus Halenospora sp. originating from a stream in North Carolina. The structures were elucidated using a set of spectroscopic and spectrometric techniques. The absolute configuration of one representative member of the compounds (7) was assigned using X-ray crystallography of an analogue that incorporated a heavy atom, whereas for compounds 8-11, a modified Mosher's ester method was utilized. The relative configurations of compounds 12-14 were determined on the basis of NOE data. Compounds 12-14 were proposed as artifacts produced by intramolecular cycloetherification of the ε-hydroxy-α,β-unsaturated ketone moieties of the parent compounds during the purification processes. The isolated compounds, except for 8 and 12, were tested against the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compound 5 was the most potent, with IC50 values of 2.9 and 7.5 μM, respectively. The compounds were evaluated as TAK1-TAB1 inhibitors but were found to be inactive.
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro , Greensboro, North Carolina 27402, United States.
authors.forename: Tamam
authors.initials: T
authors.lastname: El-Elimat
authors.forename: Huzefa A
authors.initials: HA
authors.lastname: Raja
authors.forename: Cynthia S
authors.initials: CS
authors.lastname: Day
authors.forename: Wei-Lun
authors.initials: WL
authors.lastname: Chen
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: Nicholas H
authors.initials: NH
authors.lastname: Oberlies
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D005618:Fresh Water; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D009657:North Carolina; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones
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