Diterpenoids from Tetraclinis articulata that inhibit various human leukocyte functions.
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.
Barrero
Alejandro F
AF
Departamento de Química Orgánica, Instituto de Biotecnología, Facultad de Ciencias, Universidad de Granada, Campus Fuentenueva s/n, 18071-Granada, Spain. afbarre@goliat.ugr.es
Quílez del Moral
José F
JF
Lucas
Rut
R
Payá
Miguel
M
Akssira
Mohamed
M
Akaad
Said
S
Mellouki
Fouad
F
D029779:Cupressaceae / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007962:Leukocytes / Q000187:drug effects* / Q000201:enzymology*; D008163:Luminescent Measurements; D015394:Molecular Structure; D009018:Morocco; D009504:Neutrophils / Q000201:enzymology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010196:Pancreatic Elastase / Q000187:drug effects / Q000378:metabolism; D009195:Peroxidase / Q000187:drug effects / Q000378:metabolism; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014934:Wood
D004224:Diterpenes; D009195:Peroxidase; D010196:Pancreatic Elastase