Bioactive rearranged limonoids from the Chinese mangrove Xylocarpus granatum Koenig

Zhen Fang Zhou, Hai Li Liu, Wen Zhang, Tibor Kurtán, Attila Mándi, Attila Bényei, Jia Li, Orazio Taglialatela-Scafati, Yue Wei Guo

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Two new pyridine-containing limonoids, xylogranatopyridines A and B (1 and 2) and their formal precursor, prexylogranatopyridine (3) were isolated from the twigs and leaves of the Chinese mangrove, Xylocarpus granatum. Xylogranatopyridine B (2) possesses an unprecedented rearranged B-ring together with a seco-ring A, supporting the biogenetic connection of 1-2 with 3. The chemical structures were elucidated by means of detailed spectroscopic analysis and X-ray single-crystal diffraction. The absolute configurations were assigned using electronic solid-state circular dichroism (ECD) supported by time-dependent density functional theory (TDDFT) ECD calculations and X-ray analysis. Xylogranatopyridine A (1) exhibited a significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 22.9 μM. This is the first report of PTP1B inhibitory activity of limonoids.

Original languageEnglish
Pages (from-to)6444-6449
Number of pages6
JournalTetrahedron
Volume70
Issue number37
DOIs
Publication statusPublished - Sep 16 2014

Keywords

  • ECD calculation
  • Limonoid
  • PTP1B inhibition
  • Xylocarpus granatum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Zhou, Z. F., Liu, H. L., Zhang, W., Kurtán, T., Mándi, A., Bényei, A., Li, J., Taglialatela-Scafati, O., & Guo, Y. W. (2014). Bioactive rearranged limonoids from the Chinese mangrove Xylocarpus granatum Koenig. Tetrahedron, 70(37), 6444-6449. https://doi.org/10.1016/j.tet.2014.07.027