Myo-inositol-derived glycolipids with anti-inflammatory activity from Solanum lanceolatum

J Nat Prod. 2005 Jul;68(7):1031-6. doi: 10.1021/np050054s.

Abstract

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / isolation & purification*
  • Cyclooxygenase Inhibitors / pharmacology
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification*
  • Glycolipids / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Inositol / chemistry
  • Membrane Proteins
  • Phospholipases A / antagonists & inhibitors*
  • Phospholipases A2
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Prostaglandin-Endoperoxide Synthases / drug effects*
  • Solanum / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Glycolipids
  • Membrane Proteins
  • Inositol
  • Cyclooxygenase 2
  • PTGS2 protein, human
  • Prostaglandin-Endoperoxide Synthases
  • Phospholipases A
  • Phospholipases A2