Four new briarane diterpenoids from Taiwanese gorgonian Junceella fragilis

Mar Drugs. 2013 Jun 10;11(6):2042-53. doi: 10.3390/md11062042.

Abstract

Four new 8-hydroxybriarane diterpenoids, frajunolides P-S (1-4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Crystallography, X-Ray
  • Cytochalasin B / analogs & derivatives
  • Cytochalasin B / pharmacology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Humans
  • N-Formylmethionine Leucyl-Phenylalanine / pharmacology
  • Neutrophils / drug effects
  • Neutrophils / metabolism
  • Pancreatic Elastase / metabolism
  • Spectrum Analysis
  • Superoxides / metabolism
  • Taiwan

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Superoxides
  • dihydrocytochalasin B
  • Cytochalasin B
  • N-Formylmethionine Leucyl-Phenylalanine
  • Pancreatic Elastase