6-Deoxy- and 11-Hydroxytolypodiols: Meroterpenoids from the Cyanobacterium HT-58-2

J Nat Prod. 2020 May 22;83(5):1691-1695. doi: 10.1021/acs.jnatprod.9b00844. Epub 2020 Apr 13.

Abstract

Chemical investigation of cyanobacterial strain HT-58-2, which most closely aligns with the genus Brasilomena, has led to the isolation of two compounds related to tolypodiol. The structures and absolute configuration of 6-deoxytolypodiol (1) and 11-hydroxytolypodiol (2) were elucidated by spectroscopic and spectrometric analysis. While tolypodiol previously showed anti-inflammatory activity in a mouse ear edema assay, only 2 reduced in vitro thromboxane B2 and superoxide anion (O2-) generation from Escherichia coli lipopolysaccharide-activated rat neonatal microglia to any appreciable degree.

Publication types

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

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cyanobacteria / chemistry*
  • Diterpenes / chemistry*
  • Ear Diseases / drug therapy*
  • Edema
  • Escherichia coli / chemistry*
  • Lipopolysaccharides / chemistry*
  • Mice
  • Rats
  • Superoxides / chemistry*
  • Thromboxane B2 / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Lipopolysaccharides
  • tolypodiol
  • Superoxides
  • Thromboxane B2