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

PLoS ONE

Volumn 8, Issue 10, 2013, Pages

  Oettl, Sarah K ^a   Gerstmeier, Jana ^b   Khan, Shafaat Y ^c   Wiechmann, Katja ^b   Bauer, Julia ^d   Atanasov, Atanas G ^e   Malainer, Clemens ^e   Awad, Ezzat M ^c   Uhrin, Pavel ^c   Heiss, Elke H ^e   Waltenberger, Birgit ^a   Remias, Daniel ^a   Breuss, Johannes M ^c   Boustie, Joel ^f   Dirsch, Verena M ^e   Stuppner, Hermann ^a   Werz, Oliver ^b   Rollinger, Judith M ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c MEDICAL UNIVERSITY OF VIENNA   (Austria)

^d UNIVERSITY OF TÜBINGEN   (Germany)

^e UNIVERSITY OF VIENNA   (Austria)

^f UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 O METYLOLIVETOLCARBOXYLIC ACID; ANTIINFLAMMATORY AGENT; ARACHIDONATE 5 LIPOXYGENASE; ATRANORIN; DEPSIDE; DIVARINOL; ETHYL 4 O METHYLOLIVETOLCARBOXYLATE; ETHYL HAEMATOMMATE; ETHYL OLIVETOLATE; IMBRICARIC ACID; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; METHYLBETAORCINOLCARBOXYLATE; OLIVETOL; OLIVETOLMONOMETHYL ETHER; PERLATOLIC ACID; PROSTAGLANDIN E SYNTHASE 1; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CETRELIA MONACHORUM; CONTROLLED STUDY; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; IC 50; IN VIVO STUDY; LEUKOCYTE COUNT; LICHEN (ORGANISM); MALE; MOUSE; NEUTROPHIL CHEMOTAXIS; NONHUMAN; PERITONITIS; PHYTOCHEMISTRY; PILOT STUDY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ASCOMYCOTA; BENZOATES; DEPSIDES; DRUG EVALUATION, PRECLINICAL; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LEUKOCYTES; MALE; MICE; MICE, INBRED C57BL; PERITONEUM;

EID: 84885113540     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0076929     Document Type: Article

References (35)

1. Huneck S, (1999) The significance of lichens and their metabolites. Naturwissenschaften 86: 559-570. doi:10.1007/s001140050676. PubMed: 10643590.
2. Manojlović N, Ranković B, Kosanić M, Vasiljević P, Stanojković T, (2012) Chemical composition of three Parmelia lichens and antioxidant, antimicrobial and cytotoxic activities of some their major metabolites. Phytomedicine 19: 1166-1172. doi:10.1016/j.phymed.2012.07.012. PubMed: 22921748.
3. Sokolov DN, Zarubaev VV, Shtro AA, Polovinka MP, Luzina OA, et al. (2012) Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009. Bioorg Med Chem Lett 22: 7060-7064. doi:10.1016/j.bmcl.2012.09.084. PubMed: 23099095.
4. Bucar F, Schneider I, Ogmundsdóttir H, Ingólfsdóttir K, (2004) Anti-proliferative lichen compounds with inhibitory activity on 12(S)-HETE production in human platelets. Phytomedicine 11: 602-606. doi:10.1016/j.phymed.2004.03.004. PubMed: 15636173.
5. Einarsdóttir E, Groeneweg J, Björnsdóttir GG, Hardardottir G, Omarsdóttir S, et al. (2010) Cellular Mechanisms of the Anticancer Effects of the Lichen Compound Usnic Acid. Planta Med 76: 969-974. doi:10.1055/s-0029-1240851. PubMed: 20143294.
6. Okuyama E, Umeyama K, Yamazaki M, Kinoshita Y, Yamamoto Y, (1995) Usnic Acid and Diffractaic Acid as Analgesic and Antipyretic Components of Usnea diffracta. Planta Med 61: 113-115. doi:10.1055/s-2006-958027. PubMed: 7753915.
7. Boustie J, Tomasi S, Grube M, (2011) Bioactive lichen metabolites: alpine habitats as an untapped source. Phytochem Rev 10: 287-307. doi:10.1007/s11101-010-9201-1.
8. Bauer J, Waltenberger B, Noha SM, Schuster D, Rollinger JM, et al. (2012) Discovery of Depsides and Depsidones from Lichen as Potent Inhibitors of Microsomal Prostaglandin E2 Synthase-1 Using Pharmacophore Models. Chemmedchem 7: 2077-2081. doi:10.1002/cmdc.201200345. PubMed: 23109349.
9. Murakami M, Naraba H, Tanioka T, Semmyo N, Nakatani Y, et al. (2000) Regulation of prostaglandin E2 biosynthesis by inducible membrane-associated prostaglandin E2 synthase that acts in concert with cyclooxygenase-2. J Biol Chem 275: 32783-32792. doi:10.1074/jbc.M003505200. PubMed: 10869354.
10. Koeberle A, Zettl H, Greiner C, Wurglics M, Schubert-Zsilavecz M, et al. (2008) Pirinixic Acid Derivatives as Novel Dual Inhibitors of Microsomal Prostaglandin E-2 Synthase-1 and 5-Lipoxygenase. J Med Chem 51: 8068-8076. doi:10.1021/jm801085s. PubMed: 19053751.
11. Rådmark O, Samuelsson B, (2010) Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer. J Intern Med 268: 5-14. PubMed: 20497297.
12. Obermayer W, Mayrhofer H, (2007) Hunting for Cetrelia chicitae (lichenized Ascomycetes) in the eastern European Alps. Phyton-Ann Rei Bot 47: 231-290.
13. Wirth V, (1995) Flechtenflora. Stuttg Ulmer: pp. 661.
14. Fischer L, Szellas D, Rådmark O, Steinhilber D, Werz O, (2003) Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors. FASEB J 17: 949-951. PubMed: 12670876.
15. Rozema E, Atanasov AG, Fakhrudin N, Singhuber J, Namduang U, et al. (2012) Selected Extracts of Chinese Herbal Medicines: Their Effect on NF-kappa B, PPAR alpha and PPAR gamma and the Respective Bioactive Compounds. Evid Based Complement Alternat Med.
16. Vogl S, Atanasov AG, Binder M, Bulusu M, Zehl M, et al. (2013) The Herbal Drug Melampyrum pratense. p. pp. L. (Koch): Isolation and Identification of Its Bioactive Compounds Targeting Mediators of Inflammation. Evidence-Based Complementary and Alternative Medicine.
17. Johnson-Lyles DN, Peifley K, Lockett S, Neun BW, Hansen M, et al. (2010) Fullerenol cytotoxicity in kidney cells is associated with cytoskeleton disruption, autophagic vacuole accumulation, and mitochondrial dysfunction. Toxicol Appl Pharmacol 248: 249-258. doi:10.1016/j.taap.2010.08.008. PubMed: 20713077.
18. Markasz L, Stuber G, Vanherberghen B, Flaberg E, Olah E, et al. (2007) Effect of frequently used chemotherapeutic drugs on the cytotoxic activity of human natural killer cells. Mol Cancer Ther 6: 644-654. doi:10.1158/1535-7163.MCT-06-0358. PubMed: 17308061.
19. Stern ST, Zolnik BS, McLeland CB, Clogston J, Zheng JW, et al. (2008) Induction of autophagy in porcine kidney cells by quantum dots: A common cellular response to nanomaterials? Toxicol Sci 106: 140-152. doi:10.1093/toxsci/kfn137. PubMed: 18632727.
20. Werz O, Steinhilber D, (2005) Development of 5-lipoxygenase inhibitors- lessons from cellular enzyme regulation. Biochem Pharmacol 70: 327-333. doi:10.1016/j.bcp.2005.04.018. PubMed: 15907806.
21. Huneck S, Yoshimura I, (1996) Identification of Lichen Substances. Berlin Heidelberg: Springer-Verlag. 493 pp.
22. Koeberle A, Werz O, (2009) Inhibitors of the Microsomal Prostaglandin E-2 Synthase-1 as Alternative to Non Steroidal Anti-Inflammatory Drugs (NSAIDs)- A Critical Review. Curr Med Chem 16: 4274-4296. doi:10.2174/092986709789578178. PubMed: 19754418.
23. Werz O, Steinhilber D, (2006) Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol Therapeutics 112: 701-718. doi:10.1016/j.pharmthera.2006.05.009. PubMed: 16837050.
24. Noha SM, Atanasov AG, Schuster D, Markt P, Fakhrudin N, et al. (2011) Discovery of a novel IKK-beta inhibitor by ligand-based virtual screening techniques. Bioorg Med Chem Lett 21: 577-583. doi:10.1016/j.bmcl.2010.10.051. PubMed: 21078555.
25. Henderson RB, Hobbs JAR, Mathies M, Hogg N, (2003) Rapid recruitment of inflammatory monocytes is independent of neutrophil migration. Blood 102: 328-335. doi:10.1182/blood-2002-10-3228. PubMed: 12623845.
26. Brandão LFG, Alcantara GB, Matos MDC, Bogo D, Freitas DD, et al. (2013) Cytotoxic Evaluation of Phenolic Compounds from Lichens against Melanoma Cells. Chem Pharm Bull 61: 176-183. doi:10.1248/cpb.c12-00739. PubMed: 23207680.
27. Schneider I, Bucar F, (2005) Lipoxygenase inhibitors from natural plant sources. Part 1: Medicinal plants with inhibitory activity on arachidonate 5-lipoxygenase and 5-lipoxygenase/cyclooxygenase. Phytother Res 19: 81-102. doi:10.1002/ptr.1603. PubMed: 15852496.
28. Bugni TS, Andjelic CD, Pole AR, Rai P, Ireland CM, et al. (2009) Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation. Fitoterapia 80: 270-273. doi:10.1016/j.fitote.2009.03.003. PubMed: 19289158.
29. Ingolfsdottir K, Gissurarson SR, Müller-Jakic B, Breu W, Wagner H, (1996) Inhibitory effects of the lichen metabolite lobaric acid on arachidonate metabolism in vitro. Phytomedicine 2: 243-246. doi:10.1016/S0944-7113(96)80049-3. PubMed: 23194623.
30. Ingólfsdóttir K, Wiedemann B, Birgisdóttir M, Nenninger A, Jónsdóttir S, et al. (1997) Inhibitory effects of baeomycesic acid from the lichen Thamnolia subuliformis on 5-lipoxygenase in vitro. Phytomedicine 4: 125-128. doi:10.1016/S0944-7113(97)80056-6. PubMed: 23195399.
31. Liu YQ, Hu XY, Lu T, Cheng YN, Young CYF, et al. (2012) Retigeric Acid B Exhibits Antitumor Activity through Suppression of Nuclear Factor-kappa B Signaling in Prostate Cancer Cells in Vitro and in Vivo. PLOS ONE 7.
32. Jin JQ, Li CQ, He LC, (2008) Down-regulatory Effect of Usnic Acid on Nuclear Factor-kB-dependent Tumor Necrosis Factor-a and Inducible Nitric Oxide Synthase Expression in Lipopolysaccharide-stimulated Macrophages RAW. Phytother Res 264.7: 22: 1605- 1609.
33. Saadane A, Masters S, DiDonato J, Li JF, Berger M, (2007) Parthenolide inhibits I kappa B kinase, NF-kappa B activation, and inflammatory response in cystic fibrosis cells and mice. Am J Respir Cell Mol Biol 36: 728-736. doi:10.1165/rcmb.2006-0323OC. PubMed: 17272824.
34. Segal BH, Kuhns DB, Ding L, Gallin JI, Holland SM, (2002) Thioglycollate peritonitis in mice lacking. p. C5, 5-lipoxygenase, or p47(phox): complement, leukotrienes, and reactive oxidants in acute inflammation. Journal of Leukocyte Biology 71: 410-416.
35. Seidman MA, Chew TW, Schenkel AR, Muller WA, (2009) PECAM-Independent Thioglycollate Peritonitis Is Associated With a Locus on Murine Chromosome 2. PLOS ONE 4: e4316. PubMed: 19180231.