Cyclic Steroid Glycosides from the Starfish Echinaster luzonicus: Structures and Immunomodulatory Activities

J Nat Prod. 2015 Jun 26;78(6):1397-405. doi: 10.1021/acs.jnatprod.5b00332. Epub 2015 Jun 11.

Abstract

Five new steroid glycosides, luzonicosides B-E (2-5), belonging to a rare structure group of marine glycosides, containing carbohydrate moieties incorporated into a macrocycle, and a related open carbohydrate chain steroid glycoside, luzonicoside F (6), were isolated from the starfish Echinaster luzonicus along with the previously known cyclic steroid glycoside luzonicoside A (1). The structures of compounds 2-6 were established by extensive NMR and ESIMS techniques as well as chemical transformations. Luzonicoside A (1) at concentrations of 0.01-0.1 μM was shown to be potent in lysosomal activity stimulation, intracellular ROS level elevation, and NO synthesis up-regulation in RAW 264.7 murine macrophages. Luzonicoside D (4) was less active in these biotests.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Immunologic Factors / chemistry
  • Immunologic Factors / isolation & purification*
  • Immunologic Factors / pharmacology*
  • Macrophages / drug effects
  • Marine Biology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Reactive Oxygen Species / analysis
  • Starfish / chemistry*
  • Steroids / chemistry
  • Steroids / isolation & purification*
  • Steroids / pharmacology*

Substances

  • Glycosides
  • Immunologic Factors
  • Reactive Oxygen Species
  • Steroids
  • Nitric Oxide