Four phragmalin orthoesters from the Chinese mangrove Xylocarpus granatum

Zhen Fang Zhou, Ling Yi Kong, Tibor Kurtán, Hai Li Liu, Attila Mándi, Jia Li, Yu Cheng Gu, Yue Wei Guo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Four new 8,9,30-phragmalin orthoesters (1-4), along with six related known compounds, namely xyloccensins O-S (5-9) and V (10), were isolated and characterized from the twigs and leaves of the Chinese mangrove Xylocarpus granatum. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis and by comparison with those of related known compounds in the literature. The absolute configuration of xyloccensin Q (7) was revised as its enantiomer by X-ray diffraction analysis employing graphite monochromated Cu Kα radiation (λ = 1.54 178 Å) with a Flack parameter of - 0.04 and was further secured by a time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculation. Consequently, the absolute configurations of xyloccensins O (5), P (6), R (8), S (9), and V (10) were all corrected as their corresponding enantiomers, respectively. Xyloccensin S (9) exhibited inhibitory activity against protein tyrosine phosphatase 1B, a potential drug target for the treatment of type II diabetes and obesity, with an IC50 value of 8.72 μg/mL 7

Original languageEnglish
Pages (from-to)949-954
Number of pages6
JournalPlanta Medica
Volume80
Issue number11
DOIs
Publication statusPublished - Jul 2014

Keywords

  • Meliaceae
  • Xylocarpus granatum
  • biological activity
  • configuration determination
  • phragmalin orthoesters

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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  • Cite this

    Zhou, Z. F., Kong, L. Y., Kurtán, T., Liu, H. L., Mándi, A., Li, J., Gu, Y. C., & Guo, Y. W. (2014). Four phragmalin orthoesters from the Chinese mangrove Xylocarpus granatum. Planta Medica, 80(11), 949-954. https://doi.org/10.1055/s-0034-1382840