Retinestatin, a Polyol Polyketide from a Termite Nest-Derived Streptomyces sp

J Nat Prod. 2024 Mar 22;87(3):591-599. doi: 10.1021/acs.jnatprod.3c01043. Epub 2024 Mar 5.

Abstract

A new polyol polyketide, named retinestatin (1), was obtained and characterized from the culture of a Streptomyces strain, which was isolated from a subterranean nest of the termite Reticulitermes speratus kyushuensis Morimoto. The planar structure of 1 was elucidated on the basis of the cumulative analysis of ultraviolet, infrared, mass spectrometry, and nuclear magnetic resonance spectroscopic data. The absolute configuration of 1 at 12 chiral centers was successfully assigned by employing a J-based configuration analysis in combination with ROESY correlations, a quantum mechanics-based computational approach to calculate NMR chemical shifts, and a 3 min flash esterification by Mosher's reagents followed by NMR analysis. Biological evaluation of retinestatin (1) using an in vitro model of Parkinson's disease revealed that 1 protected SH-SY5Y dopaminergic cells from MPP+-induced cytotoxicity, indicating its neuroprotective effects.

MeSH terms

  • Animals
  • Humans
  • Isoptera*
  • Molecular Structure
  • Neuroblastoma*
  • Polyketides* / chemistry
  • Polymers*
  • Streptomyces* / chemistry

Substances

  • Polyketides
  • polyol
  • Polymers