Novel oligorhamnosides from the stem bark of Cleistopholis glauca

Veronique Seidel, François Bailleul, Peter G. Waterman

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

A reinvestigation of the stem bark of Cleistopholis glauca yielded 14 compounds, of which seven were either novel or had not been previously reported from this species. These were identified as the farnesane sesquiterpene methyl-(2E,6E)-10-oxo-3,7,11-trimethyl-dodeca-2,6-dienoate (1); the azaanthracene alkaloid cleistopholine (4); two partially acetylated oligorhamnoside derivatives, 1-O-dodecanyl-2,3,4-tri-O-acetyl-α-rhamnopyranosyl-(1→3)-2,4-di-O-acetyl-α-rhamnopyranosyl-(1→3)-4-O-acetyl-α-rhamnopyranosyl-(1→4)-α-rhamnopyranoside (6) and 1-O-dodecanyl-2,4-di-O-acetyl-α-rhamnopyranosyl-(1→3)-2,4-di-O-acetyl-α-rhamnopyranosyl-(1→3)-4-O-acetyl-α-rhamnopyranosyl-(1→4)-α-rhamnopyranoside (8), for which the trivial names cleistetroside-7 and cleistetroside-6 were assigned, respectively; the dihydrobenzofuran neolignan rel-(2α,3β)-7-O-methylcedrusin (12); and the flavonoids dihydroquercetin (13) and quercetin (14). Structure assignments of all compounds were established by spectroscopic methods and comparison with published data. The chemosystematic significance of the occurrence of the isolated components is mentioned. Compounds 1, 6, and 8 are novel natural products.
Original languageEnglish
Pages (from-to)6-11
Number of pages6
JournalJournal of Natural Products
Volume63
Issue number1
Early online date3 Dec 1999
DOIs
Publication statusPublished - 2000

Keywords

  • stem bark
  • cleistopholis glauca
  • sesquiterpene
  • alkaloid
  • simple aromatic compounds
  • neolignan
  • flavonoids
  • oligosaccharide derivatives

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