Anti-inflammatory activity of pectolinarigenin and pectolinarin isolated from Cirsium chanroenicum.
In order to identify the active anti-inflammatory ingredient(s) in Cirsium chanroenicum (Compositae), its methanol extract and several solvent fractions were prepared; the methanol extract and the ethylacetate fraction inhibited cyclooxygenase-2 (COX-2)-mediated prostaglandin E2 (PGE2) and 5-lipoxygenase (5-LOX)-mediated leukotriene (LT) production in lipopolysaccharide-treated RAW 264.7 cells and A23187-treated rat basophilic leukemia (RBL-1) cells, respectively. Further bioactivity-guided fractionation of the ethylacetate fraction using column chromatography led to the isolation of pectolinarigenin (5,7-dihydroxy-4',6-dimethoxyflavone), along with pectolinarin [pectolinarigenin 7-rhamnosyl-(1-->6)-glucoside]. Pectolinarigenin strongly inhibited COX-2-mediated PGE2 and 5-LOX-mediated LT production at >1 microM, indicating that it is a dual inhibitor of COX-2/5-LOX. However, pectolinarigenin did not affect COX-2 expression or nuclear transcription factor (NF-kappaB) activation. In addition, in vivo studies demonstrated that oral administration of these two compounds at 20-100 mg/kg resulted in similar inhibitory activities against several animal models of inflammation/allergy: arachidonic acid-induced mouse ear edema, carrageenan-induced mouse paw edema and passive cutaneous anaphylaxis. All of these results suggest that pectolinarigenin and pectolinarin possess anti-inflammatory activity and that they may inhibit eicosanoid formation in inflammatory lesions. These activities certainly contribute to the anti-inflammatory mechanism of C. chanroenicum.
Lim
Hyun
H
College of Pharmacy, Kangwon National University, Chunchon, Korea.
Son
Kun Ho
KH
Chang
Hyeun Wook
HW
Bae
Kihwan
K
Kang
Sam Sik
SS
Kim
Hyun Pyo
HP
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism; D015153:Blotting, Western; D045744:Cell Line, Tumor; D002867:Chromones / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D031180:Cirsium / Q000737:chemistry*; D051546:Cyclooxygenase 2 / Q000096:biosynthesis; D015232:Dinoprostone / Q000037:antagonists & inhibitors / Q000378:metabolism; D004487:Edema / Q000532:radiotherapy; D024202:Electrophoretic Mobility Shift Assay; D015289:Leukotrienes / Q000378:metabolism; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D008297:Male; D051379:Mice; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D010323:Passive Cutaneous Anaphylaxis / Q000187:drug effects; D051381:Rats; D017207:Rats, Sprague-Dawley
D000894:Anti-Inflammatory Agents, Non-Steroidal; D002867:Chromones; D015289:Leukotrienes; D016328:NF-kappa B; C528671:pectolinarigenin; C052786:pectolinarin; D001094:Arachidonate 5-Lipoxygenase; D051546:Cyclooxygenase 2; D015232:Dinoprostone