New bromotyrosine derivatives from an association of two sponges, Jaspis wondoensis and Poecillastra wondoensis

J Nat Prod. 2003 Nov;66(11):1495-8. doi: 10.1021/np030162j.

Abstract

Three new bromotyrosine derivatives (4-6) were isolated from an association of two sponges, Jaspis wondoensis and Poecillastra wondoensis, along with the previously described (E,E)-psammaplin A (1), (E,Z)-psammaplin A (2), psammaplin D (3), bisaprasin (7), and (3-bromo-4-hydroxyphenyl)acetonitrile (8). The structures of the new compounds were established on the basis of NMR and MS spectroscopic analysis. The compounds 1, 3, and 5-7 displayed significant cytotoxicity against human lung (A549), ovarian (SK-OV-3), skin (SK-MEL-2), CNS (XF498), and colon (HCT15) cancer cell lines. Compounds 3-7 were further evaluated for antibacterial activity against methicillin- or ofloxacin-resistant Staphylococcus strains. Compound 4 exhibited more potent antibacterial activity than meropenem against several strains.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Central Nervous System Neoplasms
  • Colonic Neoplasms
  • Disulfides / chemistry
  • Disulfides / isolation & purification
  • Disulfides / pharmacology
  • Drug Screening Assays, Antitumor
  • Electron Spin Resonance Spectroscopy
  • Female
  • Humans
  • Korea
  • Lung Neoplasms
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Ofloxacin / pharmacology
  • Ovarian Neoplasms
  • Porifera / chemistry*
  • Skin Neoplasms
  • Staphylococcus / drug effects
  • Tumor Cells, Cultured / drug effects
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry
  • Tyrosine / isolation & purification
  • Tyrosine / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Disulfides
  • bromotyrosine
  • psammaplin A
  • Tyrosine
  • Ofloxacin