Bioactive and other sesquiterpenes from Chiloscyphus rivularis

Chongming Wu, Leslie Gunatilaka, Francis L. McCabe, Randall K. Johnson, Richard W. Spjut, David G I Kingston

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)1281-1286
Number of pages6
JournalJournal of Natural Products
Volume60
Issue number12
DOIs
StatePublished - Dec 1997

Fingerprint

Sesquiterpenes
sesquiterpenoids
Stereochemistry
Bioassay
stereochemistry
Cytotoxicity
Fractionation
Bioactivity
ketones
Biological Assay
Yeast
carcinoma
cytotoxicity
Assays
fractionation
bioassays
Yeasts
lungs
Cells
yeasts

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Wu, C., Gunatilaka, L., McCabe, F. L., Johnson, R. K., Spjut, R. W., & Kingston, D. G. I. (1997). Bioactive and other sesquiterpenes from Chiloscyphus rivularis. Journal of Natural Products, 60(12), 1281-1286. https://doi.org/10.1021/np970251u

Bioactive and other sesquiterpenes from Chiloscyphus rivularis. / Wu, Chongming; Gunatilaka, Leslie; McCabe, Francis L.; Johnson, Randall K.; Spjut, Richard W.; Kingston, David G I.

In: Journal of Natural Products, Vol. 60, No. 12, 12.1997, p. 1281-1286.

Research output: Contribution to journalArticle

Wu, C, Gunatilaka, L, McCabe, FL, Johnson, RK, Spjut, RW & Kingston, DGI 1997, 'Bioactive and other sesquiterpenes from Chiloscyphus rivularis', Journal of Natural Products, vol. 60, no. 12, pp. 1281-1286. https://doi.org/10.1021/np970251u
Wu, Chongming ; Gunatilaka, Leslie ; McCabe, Francis L. ; Johnson, Randall K. ; Spjut, Richard W. ; Kingston, David G I. / Bioactive and other sesquiterpenes from Chiloscyphus rivularis. In: Journal of Natural Products. 1997 ; Vol. 60, No. 12. pp. 1281-1286.
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