Amomaxins A and B, two unprecedented rearranged labdane norditerpenoids with a nine-membered ring from Amomum maximum

Org Lett. 2013 Apr 5;15(7):1572-5. doi: 10.1021/ol400348a. Epub 2013 Mar 8.

Abstract

Amomaxins A (1) and B (2), featuring an unprecedented rearranged labdane norditerpene skeleton with a nine-membered ring, along with their biosynthetic related known compound isocoronarin D (3) were isolated from the roots of Amomum maximum. Their structures with absolute configurations were determined by spectroscopic data, CD experimentation, and single-crystal X-ray diffraction. Compound 2 showed an inhibitory effect on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amomum / chemistry*
  • Animals
  • Crystallography, X-Ray
  • Cytotoxins / chemistry*
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry

Substances

  • Cytotoxins
  • Diterpenes
  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • amomaxin A
  • amomaxin B
  • Nitric Oxide