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

Limonins
Nuclear magnetic resonance
Biosynthetic Pathways
Skeleton
Inhibitory Concentration 50
Mass spectrometry
Seed
Mass Spectrometry
Seeds
Cells

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Wu, Y. B., Qing, X., Huo, C. H., Yan, H. M., Shi, Q. W., Sauriol, F., ... 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

Xylomexicanins E-H, new limonoids from Xylocarpus granatum. / Wu, Yi Bing; Qing, Xia; Huo, Chang Hong; Yan, Hui Min; Shi, Qing Wen; Sauriol, Françoise; Gu, Yu Cheng; Kiyota, Hiromasa.

In: Tetrahedron, Vol. 70, No. 30, 29.07.2014, p. 4557-4562.

Research output: Contribution to journalArticle

Wu, YB, Qing, X, Huo, CH, Yan, HM, Shi, QW, Sauriol, F, Gu, YC & Kiyota, H 2014, 'Xylomexicanins E-H, new limonoids from Xylocarpus granatum', Tetrahedron, vol. 70, no. 30, pp. 4557-4562. https://doi.org/10.1016/j.tet.2014.04.062
Wu YB, Qing X, Huo CH, Yan HM, Shi QW, Sauriol F et al. Xylomexicanins E-H, new limonoids from Xylocarpus granatum. Tetrahedron. 2014 Jul 29;70(30):4557-4562. https://doi.org/10.1016/j.tet.2014.04.062
Wu, Yi Bing ; Qing, Xia ; Huo, Chang Hong ; Yan, Hui Min ; Shi, Qing Wen ; Sauriol, Françoise ; Gu, Yu Cheng ; Kiyota, Hiromasa. / Xylomexicanins E-H, new limonoids from Xylocarpus granatum. In: Tetrahedron. 2014 ; Vol. 70, No. 30. pp. 4557-4562.
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