Anti-inflammatory 5-(11'Z-heptadecenyl)- and 5-(8'Z,11'Z-heptadecadienyl)-resorcinols from mango (Mangifera indica L.) peels.
Bioassay directed extraction and purification of mango peels revealed the 5-(11'Z-heptadecenyl)-resorcinol (1) and the known 5-(8'Z,11'Z-heptadecadienyl)-resorcinol (2) previously not described in Mangifera indica L. The structures of both compounds were determined by extensive 1D and 2D NMR studies and MS. Both compounds exhibited potent cyclooxygenase (COX)-1 and COX-2 inhibitory activity with IC(50) values ranging from 1.9 (2) to 3.5 microM (1) and from 3.5 (2) to 4.4 (1) microM, respectively, coming close to the IC(50) values of reference drugs. 5-Lipoxygenase (5-LOX) catalyzed leukotriene formation was only slightly inhibited. Structure-activity studies by referring to synthetic saturated homologues indicated that the degree of unsaturation in the alkyl chain plays a key role for COX inhibitory activity, whereas the influence of chain length was less significant.
D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology; D051545:Cyclooxygenase 1 / Q000378:metabolism; D051546:Cyclooxygenase 2 / Q000378:metabolism; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D020024:Leukotriene Antagonists / Q000737:chemistry / Q000494:pharmacology; D015289:Leukotrienes / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D031022:Mangifera / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D012118:Resorcinols / Q000737:chemistry* / Q000494:pharmacology
C530253:5-(11'Z-heptadecenyl)resorcinol; C530254:5-(8'Z,11'Z-heptadecadienyl)resorcinol; D000893:Anti-Inflammatory Agents; D016861:Cyclooxygenase Inhibitors; D020024:Leukotriene Antagonists; D015289:Leukotrienes; D010936:Plant Extracts; D012118:Resorcinols; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C031389:resorcinol