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Psammaplin A, a chitinase inhibitor isolated from the Fijian marine sponge Aplysinella rhax

  • J. N. Tabudravu
  • , V. G.H. Eijsink
  • , G. W. Gooday
  • , M. Jaspars*
  • , D. Komander
  • , M. Legg
  • , B. Synstad
  • , D. M.F. Van Aalten
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Several brominated tyrosine derived compounds, psammaplins A (1), K (2) and (3) as well as bisaprasin (4) were isolated from the Fijian marine sponge Aplysinella rhax during a bioassay guided isolation protocol. Their structures were determined using NMR and MS techniques. Psammaplin A was found to moderately inhibit chitinase B from Serratia marcescens, the mode of inhibition being non-competitive. Crystallographic studies suggest that a disordered psammaplin A molecule is bound near the active site. Interestingly, psammaplin A was found to be a potent antifungal agent.

Original languageEnglish
Pages (from-to)1123-1128
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume10
Issue number4
DOIs
Publication statusPublished - 21 Feb 2002

Funding

J.T. wishes to thank Ratu Isoa Bulikiobo and Ratu Dovibua Tagivetaua for permission to collect samples, Usaia Tabudravu and Inosa Qativi for sample collections, Akihiro Yokoyama, Mamoru Endo and Yoshikazu Shizuri of MBI for bioassay procedure and technical help, the Government of Fiji and the ORS for a scholarship. M.J. wishes to thank Gary Duncan for mass spectra and Alan McGown for anticancer bioassays. Aberdeen University Chemistry Department is thanked for the provision of NMR facilities. We thank the ESRF, Grenoble, for the time at beamline BM14. D.v.A. is supported by a Wellcome Trust Career Development Research Fellowship. The structure factors and coordinates have been deposited with the PDB (entry 1GPF).

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

  1. SDG 14 - Life Below Water
    SDG 14 Life Below Water

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