Xylomexicanins E-H, new limonoids from Xylocarpus granatum

Yi Bing Wu, Xia Qing, Chang Hong Huo, Hui Min Yan, Qing Wen Shi, Françoise Sauriol, Yu Cheng Gu, Hiromasa Kiyota

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Four novel tetranortriterpenoids, xylomexicanins E-H (1-4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9-C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC50 value of 18.83 and 15.83 μM.

Original languageEnglish
Pages (from-to)4557-4562
Number of pages6
JournalTetrahedron
Volume70
Issue number30
DOIs
Publication statusPublished - Jul 29 2014

    Fingerprint

Keywords

  • Azaspiro compounds
  • Cytotoxicity
  • Limonoids
  • Structure elucidation
  • Xylocarpus granatum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Wu, Y. B., Qing, X., Huo, C. H., Yan, H. M., Shi, Q. W., Sauriol, F., Gu, Y. C., & Kiyota, H. (2014). Xylomexicanins E-H, new limonoids from Xylocarpus granatum. Tetrahedron, 70(30), 4557-4562. https://doi.org/10.1016/j.tet.2014.04.062