Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

Bioorg Med Chem Lett. 2020 Feb 15;30(4):126946. doi: 10.1016/j.bmcl.2019.126946. Epub 2020 Jan 7.

Abstract

Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(l-Leu1-l-Pro1-l-Pro2-l-Leu2-l-Ile1-l-Pro3-l-Val1-l-Ile2) and cyclo-(l-Leu1-l-Pro1-l-Pro2-l-Leu2-l-Ile1-l-Pro3-l-Val1-l-Val2) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.

Keywords: Cyclic peptides; Mariannaea elegans NBRC102301; Mariannamides A-B; Sirtuin 1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Bacteria / drug effects
  • Cell Line
  • Fungi / drug effects
  • Hypocreales / metabolism*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Oligopeptides / chemistry
  • Oligopeptides / isolation & purification
  • Oligopeptides / metabolism*
  • Oligopeptides / pharmacology
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / metabolism*
  • Peptides, Cyclic / pharmacology
  • RNA, Messenger / metabolism
  • Sirtuin 1 / genetics
  • Sirtuin 1 / metabolism
  • Up-Regulation / drug effects

Substances

  • Oligopeptides
  • Peptides, Cyclic
  • RNA, Messenger
  • Sirtuin 1

Supplementary concepts

  • Mariannaea elegans