Myo-inositol-derived glycolipids with anti-inflammatory activity from Solanum lanceolatum.
Lanceolitols A1-A7 (1-7) and B1-B7 (9-15), two series of new myo-inositol-derived glycolipid analogues, in which a sugar moiety is replaced by a fatty acid esterified myo-inositol moiety, were isolated from the leaves of Solanum lanceolatum. Their structures were elucidated on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS), as well as chemical analysis. All the compounds showed in vivo anti-inflammatory activity against ear edema in mice produced by 12-O-tetradecanoylphorbol-13-acetate (TPA). In vitro enzyme inhibition studies showed that the mixture of lanceolitols A1-A7 inhibited by 58.56% phospholipase A2 from bee venom, while the mixture of lanceolitols B1-B7 was cyclooxygenase-2 (COX-2) inhibitors (IC50 = 237 microM).
Herrera-Salgado
Yesenia
Y
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, 62210, Cuernavaca, Morelos, México.
Garduño-Ramírez
María Luisa
ML
Vázquez
Lorena
L
Rios
María Yolanda
MY
Alvarez
Laura
L
D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D007294:Inositol / Q000737:chemistry; D008565:Membrane Proteins; D010741:Phospholipases A / Q000037:antagonists & inhibitors*; D054467:Phospholipases A2; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases / Q000187:drug effects*; D032322:Solanum / Q000737:chemistry*
D000893:Anti-Inflammatory Agents; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D006017:Glycolipids; D008565:Membrane Proteins; D007294:Inositol; D051546:Cyclooxygenase 2; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases; D010741:Phospholipases A; D054467:Phospholipases A2