6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae): Isolation and its crystal structure

Huaping Zhang, Don Vanderveer, Xi Wang, Feng Chen, Xiao M. Androulakis, Michael J. Wargovich

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Khayanone was isolated from the stem bark of African mahogany, Khaya senegalensis (Meliaceae), and characterized as 6S,8α-dihydroxy-14,15- dihydrocarapin on the basis of spectral analysis and single crystal X-ray diffraction study. The compound crystallizes in the tetragonal space group P4 1 2 1 2 with unit cell parameters: a = 13.2315(19) Å, c = 29.118(6) Å, Z = 8. The crystal structure has been solved by direct methods and refined to R = 0.0375 for 4552 unique reflections. The six-membered rings A and B exist in boat conformations, rings C and D in chair conformations, and the furan ring is planar. The crystal structure is stabilized by O-H•••O and C-H•••O interactions. This is the first report about 6S configuration of mexicanolide revealed by X-ray diffraction analysis. The configuration of oxygenated C-6 in mexicanolide-group limonoids is discussed.

Original languageEnglish (US)
Pages (from-to)463-467
Number of pages5
JournalJournal of Chemical Crystallography
Volume37
Issue number7
DOIs
StatePublished - Jul 1 2007

Keywords

  • African mahogany
  • Configuration
  • Crystal structure
  • Direct method
  • Khaya senegalensis
  • Khayanone
  • Limonoid
  • Meliaceae
  • Mexicanolide

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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