Isolation and structure of ruprechstyril from Ruprechtia tangarana

George Pettit, Yanhui Meng, Delbert L. Herald, Keith A N Graham, Robin Pettit, Dennis L. Doubek

Research output: Contribution to journalArticle

61 Scopus citations

Abstract

Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2′-O-methylevernic acid (3), 3,3′,4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3β,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.

Original languageEnglish (US)
Pages (from-to)1065-1069
Number of pages5
JournalJournal of Natural Products
Volume66
Issue number8
DOIs
StatePublished - Aug 1 2003

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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