title: Noreupenifeldin, a tropolone from an unidentified ascomycete.
abstract: Noreupenifeldin ( 2), a new monotropolone derivative of the bistropolone eupenifeldin ( 1), was isolated from an unidentified ascomycete by bioassay-guided fractionation as part of our search for new anthelmintics. The structure of 1 was confirmed by comparison with literature data. The structure of 2 was elucidated from MS and 1D and 2D NMR data. Compounds 1 and 2 are diastereomers of pycnidione ( 3) and epolone A ( 4), respectively. Compounds 1- 3 were evaluated for their anthelmintic activity against the parasitic worm Hemonchus contortus. Compounds 1 and 3 exhibited modest in vitro activity, showing EC 90 50 and 83 microg/mL, respectively, in reducing motility of L3 larvae of H. contortus. Compound 2 was inactive, indicating that the second tropolone moiety is required for activity.
authors: Merck Research Laboratories, Rahway, New Jersey 07065, USA.
authors: Sloan
authors: S
authors: Ayers
authors: Deborah L
authors: DL
authors: Zink
authors: Joanne S
authors: JS
authors: Powell
authors: Christine M
authors: CM
authors: Brown
authors: Alan
authors: A
authors: Grund
authors: Gerald F
authors: GF
authors: Bills
authors: Gonzalo
authors: G
authors: Platas
authors: Donald
authors: D
authors: Thompson
authors: Sheo B
authors: SB
authors: Singh
mesh_terms: D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D006189:Haemonchus / Q000187:drug effects; D015394:Molecular Structure; D014334:Tropolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C529039:noreupenifeldin; D014334:Tropolone