New acetylenes isolated from the bark of Heisteria acuminata.
Five new linear acetylenic compounds, namely, pentadeca-6,8,10-triynoic acid (1), octadeca-8,10,12-triynoic acid (2), trans-pentadec-10-en-6,8-diynoic acid (3), cis-hexadec-11-en-7,9-diynoic acid (4), and cis-octadec-12-en-7,9-diynoic acid (5), were isolated from the bark of Heisteria acuminata by bioassay-guided fractionation, using cyclooxygenase (COX) and 5-lipoxygenase (5-LO) assays as models for antiinflammatory activity. The structures of compounds 1-5 were established by NMR, MS, IR, and Raman spectroscopy. These isolated compounds were found to be potent inhibitors of COX. Compounds 4 and 5 were the most potent inhibitors of 5-LO, whereas the other compounds only showed a weak inhibition at the same concentration.
Kraus
C M
CM
Institute of Pharmaceutical Biology, University of Munich, Germany.
Neszmélyi
A
A
Holly
S
S
Wiedemann
B
B
Nenninger
A
A
Torssell
K B
KB
Bohlin
L
L
Wagner
H
H
D000114:Acetylene / Q000031:analogs & derivatives* / Q000302:isolation & purification* / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000302:isolation & purification* / Q000494:pharmacology; D016861:Cyclooxygenase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology; D004484:Ecuador; D016859:Lipoxygenase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D019441:Plant Epidermis / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013256:Steroids
D000893:Anti-Inflammatory Agents; D016861:Cyclooxygenase Inhibitors; D016859:Lipoxygenase Inhibitors; D010936:Plant Extracts; D013256:Steroids; D000114:Acetylene