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In vitro screening of 17 Alpine lichen species for their inhibitory activity against 5-lipoxygenase, microsomal prostaglandin E 2  synthase-1 and nuclear factor kappa B revealed  Cetrelia monachorum  (Zahlbr.) W.L. Culb. & C.F. Culb. As conceivable source for novel anti-inflammatory compounds. Phytochemical investigation of the ethanolic crude extract resulted in the isolation and identification of 11 constituents, belonging to depsides and derivatives of orsellinic acid, olivetolic acid and olivetol. The two depsides imbricaric acid ( 4 ) and perlatolic acid ( 5 ) approved dual inhibitory activities on microsomal prostaglandin E 2  synthase-1 (IC 50  = 1.9 and 0.4 µM, resp.) and on 5-lipoxygenase tested in a cell-based assay (IC 50  = 5.3 and 1.8 µM, resp.) and on purified enzyme (IC 50  = 3.5 and 0.4 µM, resp.). Additionally, these two main constituents quantified in the extract with 15.22% ( 4 ) and 9.10% ( 5 ) showed significant inhibition of tumor necrosis factor alpha-induced nuclear factor kappa B activation in luciferase reporter cells with IC 50  values of 2.0 and 7.0 µM, respectively. In a murine  in vivo  model of inflammation,  5  impaired the inflammatory, thioglycollate-induced recruitment of leukocytes to the peritoneum.   The potent inhibitory effects on the three identified targets attest  4  and  5  a pronounced multi-target anti-inflammatory profile which warrants further investigation on their pharmacokinetics and  in vivo  efficacy.

Imbricaric Acid and Perlatolic Acid: Multi-Targeting Anti-Inflammatory Depsides from Cetrelia monachorum