Stereostructure and anti-inflammatory activity of three diastereomers of ocobullenone from Ocotea bullata.
A novel diastereomer of ocobullenone. designated as sibyllenone, was isolated from the stem bark of mature Ocotea bullata in the course of a search for anti-inflammatory compounds from this plant. The stereostructure was established by X-ray crystallography and corroborated by NOESY analysis. Ocobullenone, obtained previously, was re-isolated and crystallised successfully for X-ray analysis, thus making possible an accurate spatial comparison of ocobullenone, iso-ocobullenone and the new stereoisomer. Tested pharmacologically for cyclooxygenase-1 and 2, and 5-lipoxygenase inhibition, sibyllenone was the only compound from O. bullata which showed good inhibitory activity towards 5-lipoxygenase.
Zschocke
S
S
Research Centre for Plant Growth and Development, School of Botany and Zoology, University of Natal Pietermaritzburg, Scottsville, South Africa.
van Staden
J
J
Paulus
K
K
Bauer
R
R
Horn
M M
MM
Munro
O Q
OQ
Brown
N J
NJ
Drewes
S E
SE
D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification*; D001094:Arachidonate 5-Lipoxygenase / Q000737:chemistry; D018360:Crystallography, X-Ray; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification; D004146:Dioxanes / Q000737:chemistry / Q000302:isolation & purification*; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D019770:Lauraceae / Q000737:chemistry*; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases; D013237:Stereoisomerism
D000893:Anti-Inflammatory Agents; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D004146:Dioxanes; D007527:Isoenzymes; D016859:Lipoxygenase Inhibitors; C420976:ocobullenone; D001094:Arachidonate 5-Lipoxygenase; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases