An unreported bis-abeo cembrane-type diterpenoid with antioxidative and anti-lipoxygenase activities from the muricid gastropod mollusc Chicoreus ramosus

Nat Prod Res. 2020 Jun;34(12):1678-1686. doi: 10.1080/14786419.2018.1527833. Epub 2018 Dec 22.

Abstract

The chemical analyses of ethyl acetate-methanol (EtOAc-MeOH) extract of muricid gastropod mollusk, Chicoreus ramosus from the southeastern coast of Indian peninsular led to the identification of unprecedented cembrane-type diterpenoid, which was characterized as (3E, 6E, 10E)-8a-butoxy-17(15→14), 20(12→11)-bis-abeo-cembra-3,6,10,14(17),15-pentaene (1). The structure of the studied cembrane was unambiguously assigned through the extensive spectroscopic experimentations. The antioxidant potentials of the bis-abeo cembrane as determined by in vitro 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid diammonium salt radical quenching potentials were greater (IC50 < 0.40 mg/mL) related to α-tocopherol (IC50 > 0.60 mg/mL). The pro-inflammatory anti-5-lipoxygenase potential of studied cembrane was higher (IC50 < 0.80 mg/mL) related to those demonstrated by ibuprofen and sodium salicylate (IC50 > 0.90 mg/mL).

Keywords: Chicoreus ramosus; Gastropod mollusc; anti-inflammatory; bis-abeo cembrane-type diterpenoid; muricidae.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology
  • Biphenyl Compounds
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Gastropoda / chemistry*
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / isolation & purification*
  • Lipoxygenase Inhibitors / pharmacology
  • Mollusca / chemistry*
  • Sulfonic Acids / chemistry

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Biphenyl Compounds
  • Diterpenes
  • Lipoxygenase Inhibitors
  • Sulfonic Acids
  • cembrane
  • diphenyl