Discovery of cyclooxygenase inhibitors from medicinal plants used to treat inflammation

Pharmacological Research

Volumn 61, Issue 6, 2010, Pages 519-524

  Cao, Hongmei ^a   Yu, Rui ^a   Choi, Yongsoo ^a   Ma, Zhong Ze ^b   Zhang, Hongjie ^a   Xiang, Wei ^a   Lee, David Yue Wei ^b   Berman, Brian M ^c   Moudgil, Kamal D ^c   Fong, Harry H S ^a   van Breemen, Richard B ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF MARYLAND SCHOOL OF MEDICINE   (United States)

Author keywords

Botanical dietary supplements; COX 2; Cryptotanshinone; Cyclooxygenase; Drug discovery; Senkyunolide O

Indexed keywords

ACETYL 11 OXO BETA BOSWELLIC ACID; ACETYL ALPHA BOSWELLIC ACID; ACETYL BETA BOSWELLIC ACID; BETA BOSWELLIC ACID; BETULIC ACID; CHINESE DRUG; CRYPTOTANSHINONE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; GLYCYRRHETINIC ACID; HERBACEOUS AGENT; HUO LUO XIAO LING DAN; ISOIMPERATORIN; ISOLIQUIRITIGENIN; LINARIGENIN; NOTOPTEROL; OSTRUTHIN; PHENETHYL FERULATE; PROSTAGLANDIN SYNTHASE INHIBITOR; ROBURIC ACID; SENKYUNOLIDE O; SITOSTEROL; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHINESE MEDICINE; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; IC 50; INFLAMMATION; LIGAND BINDING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MEDICINAL PLANT; PRIORITY JOURNAL; ULTRAFILTRATION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DRUGS, CHINESE HERBAL; HUMANS;

EID: 77952886752     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2010.02.007     Document Type: Article

References (33)

1. Kvien T.K. Epidemiology and burden of illness of rheumatoid arthritis. Pharmacoeconomics 2004, 22:1-12.
2. Zhang R.X., Fan A.Y., Zhou A.N., Moudgil K.D., Ma Z.Z., Lee D.Y., et al. Extract of the Chinese herbal formula Huo Luo Xiao Ling Dan inhibited adjuvant arthritis in rats. J Ethnopharmacol 2009, 121:366-371.
3. Barnes P.M., Powell-Griner E., McFann K., Nahin R.L. Complementary and alternative medicine use among adults: United States, 2002. Adv Data 2004, 343:1-19.
4. Ho L.J., Lai J.H. Chinese herbs as immunomodulators and potential disease-modifying antirheumatic drugs in autoimmune disorders. Curr Drug Metab 2004, 5:181-192.
5. Lao L., Fan A.Y., Zhang R.X., Zhou A., Ma Z.Z., Lee D.Y., et al. Anti-hyperalgesic and anti-inflammatory effects of the modified Chinese herbal formula Huo Luo Xiao Ling Dan (HLXL) in rats. Am J Chin Med 2006, 34:833-844.
6. Chadwick L.R., Fong H.H.S. Quality assurance and standardization in herb-drug interaction evaluation and documentation. Herbal supplement-drug interactions: scientific and regulatory perspectives 2006, 191-204. Taylor & Francis, New York. Y.W.F. Lam, S.-M. Huang, S.D. Hall (Eds.).
7. Fong H.H.S., Pauli G.F., Bolton J.L., van Breemen R.B., Banuvar S., Shulman L., et al. Chapter 2: evidence-based herbal medicine: challenges in efficacy and safety assessments. Annals of traditional Chinese medicine-vol. 2, current review of Chinese medicine: quality control of herbs and herbal medicine 2006, 11-26. World Scientific, New Jersey. P.C. Leung, H. Fong, C.C. Xue (Eds.).
8. van Breemen R.B., Fong H.H., Farnsworth N.R. The role of quality assurance and standardization in the safety of botanical dietary supplements. Chem Res Toxicol 2007, 20:577-582.
9. van Breemen R.B., Huang C.R., Nikolic D., Woodbury C.P., Zhao Y.Z., Venton D.L. Pulsed ultrafiltration mass spectrometry: a new method for screening combinatorial libraries. Anal Chem 1997, 69:2159-2164.
10. Zhao Y.Z., van Breemen R.B., Nikolic D., Huang C.R., Woodbury C.P., Schilling A., et al. Screening solution-phase combinatorial libraries using pulsed ultrafiltration/electrospray mass spectrometry. J Med Chem 1997, 40:4006-4012.
11. Nikolic D., van Breemen R.B. Screening for inhibitors of dihydrofolate reductase using pulsed ultrafiltration mass spectrometry. Comb Chem High Throughput Screen 1998, 1:47-55.
12. Nikolic D., Habibi-Goudarzi S., Corley D.G., Gafner S., Pezzuto J.M., van Breemen R.B. Evaluation of cyclooxygenase-2 inhibitors using pulsed ultrafiltration-mass spectrometry. Anal Chem 2000, 72:3853-3859.
13. Gu C., Nikolic D., Lai J., Xu X., van Breemen R.B. Assays of ligand-human serum albumin binding using pulsed ultrafiltration and liquid chromatography-mass spectrometry. Comb Chem High Throughput Screen 1999, 2:353-359.
14. Sun Y., Gu C., Liu X., Liang W., Yao P., Bolton J.L., et al. Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors. J Am Soc Mass Spectrom 2005, 16:271-279.
15. Liu D., Guo J., Luo Y., Broderick D.J., Schimerlik M.I., Pezzuto J.M., et al. Screening for ligands of human retinoid X receptor-α using ultrafiltration mass spectrometry. Anal Chem 2007, 79:9398-9402.
16. Noreen Y., Ringbom T., Perera P., Danielson H., Bohlin L. Development of a radiochemical cyclooxygenase-1 and -2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis. J Nat Prod 1998, 61:2-7.
17. Belsner K., Buchele B., Werz U., Syrovets T., Simmet T. Structural analysis of pentacyclic triterpenes from the gum resin of Boswellia serrata by NMR spectroscopy. Magn Reson Chem 2003, 41:115-122.
18. Culioli G., Mathe C., Archier P., Vieillescazes C. A lupane triterpene from frankincense (Boswellia sp., Burseraceae). Phytochemistry 2003, 62:537-541.
19. Peng C., Bodenhausen G., Qiu S., Fong H., Farnsworth N., Yuan S., et al. Computer-assisted structure elucidation: application of CISOC-SES to the resonance assignment and structure generation of betulinic acid. Magn Reson Chem 1998, 36:267-278.
20. Naito T., Katsuhara T., Niitsu K., Ikeya Y., Okada M., Mitsuhashi H. Phthalide dimers from Ligusticum chuangxiong Hort. Heterocycles 1991, 32:2433-2442.
21. Chen Q.L., Shi Z.Y., Tu G.Z., Sun W.J. Studies on the chemical constituents in root of Gentiana macrophylla from Shaanxi. Zhongguo Zhong Yao Za Zhi 2005, 30:1519-1522.
22. Zdero C., Jakupovic J., Bohlmann F. Diterpenes and other constituents from Pteronia Species. Phytochemistry 1990, 29:1231-1245.
23. Sairafianpour M., Christensen J., Staerk D., Budnik B.A., Kharazmi A., Bagherzadeh K., et al. Leishmanicidal, antiplasmodial, and cytotoxic activity of novel diterpenoid 1,2-quinones from Perovskia abrotanoides: new source of tanshinones. J Nat Prod 2001, 64:1398-1403.
24. Cuendet M., Mesecar A.D., DeWitt D.L., Pezzuto J.M. An ELISA method to measure inhibition of the COX enzymes. Nat Protoc 2006, 1:1915-1921.
25. 2 production in biological fluids. Anal Biochem 2008, 372:41-51.
26. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., et al. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, Celecoxib). J Med Chem 1997, 40:1347-1365.
27. Marnett L.J., Kalgutkar A.S. Cyclooxygenase 2 inhibitors: discovery, selectivity and the future. Trends Pharmacol Sci 1999, 20:465-469.
28. Gierse J.K., Koboldt C.M., Walker M.C., Seibert K., Isakson P.C. Kinetic basis for selective inhibition of cyclo-oxygenases. Biochem J 1999, 339:607-614.
29. Kang S.S., Cuendet M., Endringer D.C., Croy V.L., Pezzuto J.M., Lipton M.A. Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB. Bioorg Med Chem 2009, 17:1044-1054.
30. Siemoneit U., Hofmann B., Kather N., Lamkemeyer T., Madlung J., Franke L., et al. Identification and functional analysis of cyclooxygenase-1 as a molecular target of boswellic acids. Biochem Pharmacol 2008, 75:503-513.
31. Yogeeswari P., Sriram D. Betulinic acid and its derivatives: a review on their biological properties. Curr Med Chem 2005, 12:657-666.
32. Zschocke S., Lehner M., Bauer R. 5-Lipoxygenase and cyclooxygenase inhibitory active constituents from Qianghuo (Notopterygium incisum). Planta Med 1997, 63:203-206.
33. Jin D.Z., Yin L.L., Ji X.Q., Zhu X.Z. Cryptotanshinone inhibits cyclooxygenase-2 enzyme activity but not its expression. Eur J Pharmacol 2006, 549:166-172.