Khayanolides from African mahogany Khaya senegalensis (Meliaceae): A revision

Huaping Zhang, Junjie Tan, Don VanDerveer, Xi Wang, Michael J. Wargovich, Feng Chen

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

Five khayanolides (1-O-acetylkhayanolide B 1, khayanolide B 2, khayanolide E 3, 1-O-deacetylkhayanolide E 4, 6-dehydroxylkhayanolide E 5) were isolated from the stem bark of African mahogany Khaya senegalensis (Meliaceae). Their structures and absolute configurations were determined through extensive spectroscopic analyses including MS, NMR, and single-crystal X-ray diffraction experiments. The results established that two previously reported khayanolides, 1α-acetoxy-2β,3α,6,8α,14β-pentahydroxy-[4.2. 110,30.11,4]-tricyclomeliac-7-oate 6 and 1α,2β,3α,6,8α,14β-hexahydroxy-[4.2.110, 30.11,4]-tricyclomeliac-7-oate 7, were, in fact, 1-O-acetylkhayanolide B 1 and khayanolide B 2, and that the two reported phragmalin derivatives, methyl 1α-acetoxy-6,8α,14β,30β-tetrahydroxy-3-oxo- [3.3.110,2.11,4]-tricyclomeliac-7-oate 8 and methyl 1α,6,8α,14β,30β-pentahydroxy-3-oxo-[3.3.110,2 .11,4]-tricyclomeliac-7-oate 9, were, in fact, khayanolide E 3 and 1-O-deacetylkhayanolide E 4, respectively. Based on the results from this study and consideration of the biogenetic pathway, the methyl 6-hydroxyangolensate in African mahogany K. senegalensis should have a C-6 S configuration while methyl 6-hydroxyangolensate in genuine mahogany Swietenia species should have a C-6 R configuration.

Original languageEnglish (US)
Pages (from-to)294-299
Number of pages6
JournalPhytochemistry
Volume70
Issue number2
DOIs
StatePublished - Jan 1 2009
Externally publishedYes

Keywords

  • 1-O-acetylkhayanolide B
  • 1-O-deacetylkhayanolide E
  • 6-Dehydroxylkhayanolide E
  • African mahogany
  • Khaya senegalensis
  • Khayanolide
  • Khayanolide B
  • Khayanolide E
  • Limonoid
  • Meliaceae
  • Methyl 6-hydroxyangolensate
  • Structure revision

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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