Endolides A and B, Vasopressin and Serotonin-Receptor Interacting N-Methylated Peptides from the Sponge-Derived Fungus Stachylidium sp

Org Lett. 2016 Feb 5;18(3):528-31. doi: 10.1021/acs.orglett.5b03553. Epub 2016 Jan 15.

Abstract

The marine-derived fungus Stachylidium sp. was isolated from the sponge Callyspongia sp. cf. C. flammea. Culture on a biomalt medium supplemented with sea salt led to the isolation of two new, most unusual N-methylated peptides, i.e., the tetrapeptides endolide A and B (1 and 2). Both of these contain the very rare amino acid 3-(3-furyl)-alanine. In radioligand binding assays endolide A (1) showed affinity to the vasopressin receptor 1A with a Ki of 7.04 μM, whereas endolide B (2) exhibited no affinity to the latter receptor, but was selective toward the serotonin receptor 5HT2b with a Ki of 0.77 μM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Callyspongia / chemistry
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology*
  • Porifera / microbiology*
  • Receptor, Serotonin, 5-HT2B / drug effects
  • Serotonin / metabolism
  • Vasopressins

Substances

  • Peptides, Cyclic
  • Receptor, Serotonin, 5-HT2B
  • endolide A
  • endolide B
  • Vasopressins
  • Serotonin