J. Nat. Prod., 60 (12), 1281 -1286, 1997. np970251u S0163-3864(97)00251-6

Copyright © 1997 American Chemical Society and American Society of Pharmacognosy

Bioactive and Other Sesquiterpenes from Chiloscyphus rivularis

Chongming Wu, A. A. Leslie Gunatilaka,^,1 Francis L. McCabe, Randall K. Johnson, Richard W. Spjut, and David G. I. Kingston*

Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061-0212, Research and Development, SmithKline Beecham Pharmaceuticals, P.O. Box 1539, King of Prussia, Pennsylvania 19406-0939, and World Botanical Associates, P.O. Box 2829, Laurel, Maryland 20709-0829

Received May 14, 1997

Abstract:

Bioassay-directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded five new sesquiterpenes, 12-hydroxychiloscyphone (2), chiloscypha-2,7-dione (3), 12-hydroxychiloscypha-2,7-dione (4), chiloscypha-2,7,9-trione (5), and rivulalactone (6) in addition to the known sesquiterpenes, 4-hydroxyoppositan-7-one (7), chiloscyphone (1), and isointermedeol (8). The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpene, was confirmed by its synthesis starting from 1. Compound 2 showed selective bioactivity in our yeast-based DNA-damaging assay and cytotoxicity to human lung carcinoma cells.

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