Antineoplastic agents. 397: Isolation and structure of sesterstatins 4 and 5 from Hyrtios erecta (the Republic of Maldives)

Bioorg Med Chem Lett. 1998 Aug 18;8(16):2093-8. doi: 10.1016/s0960-894x(98)00373-4.

Abstract

The wide ranging marine sponge Hyrtios erecta is the source of the spongistatins, a new class of macrocyclic lactone antineoplastic agents. Continuation of a detailed investigation of cancer cell growth inhibitory (P388 lymphocytic leukemia) fractions (trace) from H. erecta has revealed the presence (10(-5) to 10(-7)% yield) of cytotoxic pentacyclic sesterterpenes. Employing P388 leukemia and human tumor cell line-guided bioassay techniques, two new moderate inhibitors of cancer cells were isolated and named sesterstatins 4 (1a, P388 ED50 4.9 micrograms/mL) and 5 (1b, DU-145 prostate GI50 1.9 micrograms/mL). Similar to other sesterterpenes, sesterstatin 5 inhibited growth of a Gram-positive bacterium. High field (500 MHz) 2-D NMR techniques were primarily employed for initial structural assignments, and structural assignments were confirmed by X-ray crystal structure determination of sesterstatin 4 (1a) and 5 (1b).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / toxicity
  • Cell Division / drug effects
  • Cell Survival / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Indian Ocean Islands
  • Leukemia P388
  • Male
  • Mice
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Porifera*
  • Structure-Activity Relationship
  • Terpenes / chemistry*
  • Terpenes / isolation & purification*
  • Terpenes / toxicity
  • Tumor Cells, Cultured

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Terpenes
  • sesterstatin 4
  • sesterstatin 5