Noreupenifeldin, a tropolone from an unidentified ascomycete

被引:18
作者
Ayers, Sloan [1 ]
Zink, Deborah L. [1 ]
Powell, Joanne S. [2 ]
Brown, Christine M. [2 ]
Grund, Alan [3 ]
Bills, Gerald F. [4 ]
Platas, Gonzalo [4 ]
Thompson, Donald [2 ]
Singh, Sheo B. [1 ]
机构
[1] Merck Res Labs, Nat Prod Chem, Rahway, NJ 07065 USA
[2] Merck & Co Inc, Branchburg Farm, Somerville, NJ 08876 USA
[3] Biotechn Resources, Manitowoc, WI 54220 USA
[4] CIBE, Merck Sharp & Dohme Espana, Madrid 28027, Spain
来源
JOURNAL OF NATURAL PRODUCTS | 2008年 / 71卷 / 03期
关键词
D O I
10.1021/np070513k
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
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 pyenidione (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 mu g/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.
引用
收藏
页码:457 / 459
页数:3
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