Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions

J Nat Prod. 2003 Jun;66(6):844-50. doi: 10.1021/np0204949.

Abstract

Ten new compounds, eight of them pimarane derivatives (1-8), together with a menthane dimer (9) and a totarane diterpenoid (10), were isolated from the leaves and wood of Tetraclinis articulata. The structures of 1-10 were established by using spectroscopic techniques, including 2D NMR spectra. Pimaranes 1-5 were found to possess an unusual cis interannular union of the B and C rings, which, from a biogenetic perspective, could be derived from the hydration of a carbocation at C-8. Compounds 4-6 and a mixture of 7 and 11 modulated different human leukocyte functions at a concentration of 10 microM, mainly the degranulation process measured as myeloperoxidase release and, to a lesser extent, the superoxide production measured by chemiluminescence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cupressaceae / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Humans
  • Leukocytes / drug effects*
  • Leukocytes / enzymology*
  • Luminescent Measurements
  • Molecular Structure
  • Morocco
  • Neutrophils / enzymology
  • Nuclear Magnetic Resonance, Biomolecular
  • Pancreatic Elastase / drug effects
  • Pancreatic Elastase / metabolism
  • Peroxidase / drug effects
  • Peroxidase / metabolism
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Wood

Substances

  • Diterpenes
  • Peroxidase
  • Pancreatic Elastase