Psammocindoles A-C: Isolation, Synthesis, and Bioactivity of Indole-γ-lactams from the Sponge Psammocinia vermis

Org Lett. 2021 Jun 18;23(12):4667-4671. doi: 10.1021/acs.orglett.1c01410. Epub 2021 Jun 1.

Abstract

Psammocindoles A-C (1-3), a new class of indole alkaloids, were isolated from a Psammocinia vermis sponge. By combined spectroscopic analyses, the structures of these compounds were determined to be the indole-γ-lactams derived from three amino acid residues. In addition, an enantiomer psammocindole D (4), and the N-lactam isomers isopsammocindoles A-D (5-8) were also synthesized. These natural products and synthetic analogues were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Products
  • Humans
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Lactams / chemistry*
  • Lactams / isolation & purification
  • Mesenchymal Stem Cells / chemistry
  • Mesenchymal Stem Cells / drug effects*
  • Molecular Structure
  • Porifera / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Indole Alkaloids
  • Lactams