New Acetylenes Isolated from the Bark of Heisteria acuminata

• Published in: Journal of natural products (Washington, D.C.) D.C.), 1998-04, Vol.61 (4), p.422-427
• Main Authors: Kraus, Christina M, Neszmélyi, András, Holly, Sándor, Wiedemann, Beate, Nenninger, Anneli, Torssell, Kurt B. G, Bohlin, Lars, Wagner, Hildebert
• Format: Article
• Language: English
• Subjects: Acetylene - analogs & derivatives; Acetylene - isolation & purification; Acetylene - pharmacology; ALKYNES; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; ANTIINFLAMMATOIRE; ANTIINFLAMMATORY AGENTS; ANTINFLAMATORIOS; BARK; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CORTEZA; CYCLOOXYGENASE; Cyclooxygenase Inhibitors - isolation & purification; Cyclooxygenase Inhibitors - pharmacology; DRUG PLANTS; ECORCE; ECUADOR; ENZYME INHIBITORS; EQUATEUR; ESPECTROMETRIA; ESTRUCTURA QUIMICA; FARMACI; General pharmacology; HIDROCARBUROS; HYDROCARBONS; HYDROCARBURE; INHIBIDORES DE ENZIMAS; INHIBITEUR D'ENZYME; LIPOXIGENASA; LIPOXYGENASE; Lipoxygenase Inhibitors - isolation & purification; Lipoxygenase Inhibitors - pharmacology; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; OLACACEAE; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; PHARMACY; Plant Epidermis - chemistry; Plant Extracts - chemistry; Plant Extracts - pharmacology; PLANTAS MEDICINALES; PLANTE MEDICINALE; Plants, Medicinal - chemistry; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Steroids; STRUCTURE CHIMIQUE
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/np970357p

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.