• DOI:10.1055/s-0034-1382840
• Corpus ID: 20480567

Four phragmalin orthoesters from the Chinese mangrove Xylocarpus granatum.

@article{Zhou2014FourPO,
  title={Four phragmalin orthoesters from the Chinese mangrove Xylocarpus granatum.},
  author={Zhen-Fang Zhou and Lingyi Kong and Tibor Kurt{\'a}n and Hai-li Liu and Attila M{\'a}ndi and Jia Li and Yucheng Gu and Yue‐Wei Guo},
  journal={Planta medica},
  year={2014},
  volume={80 11},
  pages={
          949-54
        }
}

• Zhen-Fang Zhou, L. Kong, +5 authors Yue‐Wei Guo
• Published 1 July 2014
• Chemistry
• Planta medica

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=1.54178 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.