LC-MS method for the simultaneous quantitation of the anti-inflammatory constituents in oregano (Origanum Species)

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 12, 2010, Pages 7119-7125

  Shen, Diandian ^a   Pan, Min Hsiung ^b   Wu, Qing Li ^a   Park, Chung Heon ^a   Juliani, H Rodolfo ^a   Ho, Chi Tang ^c   Simon, James E ^a  

^a Rutgers University   (United States)

^b NATIONAL KAOHSIUNG UNIVERSITY OF APPLIED SCIENCES   (Taiwan)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

Anti inflammation; LC MS; Oleanolic acid; Oregano; Rosmarinic acid; Ursolic acid

Indexed keywords

ANTIINFLAMMATORY AGENT; CINNAMIC ACID DERIVATIVE; DEPSIDE; OLEANOLIC ACID; PLANT EXTRACT; ROSMARINIC ACID; TRITERPENE; URSOLIC ACID;

ARTICLE; CHEMISTRY; EVALUATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; OREGANO; EVALUATION STUDY; ORIGANUM; PROCEDURES;

ANTI-INFLAMMATORY AGENTS; CHROMATOGRAPHY, LIQUID; CINNAMATES; DEPSIDES; MASS SPECTROMETRY; OLEANOLIC ACID; ORIGANUM; PLANT EXTRACTS; TRITERPENES;

ORIGANUM; ORIGANUM SYRIACUM; ORIGANUM VULGARE;

EID: 77953631826     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf100636h     Document Type: Article

References (41)

1. Asero, R. Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update Allergy Asthma Clin. Immunol. 2007, 3, 24-30
2. Goldkind, L.; Laine, L. A systematic review of NSAIDs withdrawn from the market due to hepatotoxicity: lessons learned from the bromfenac experience Pharmacoepidemiol. Drug Saf. 2006, 15, 213-220
3. Singh, G.; Triadafilopoulos, G. Epidemiology of NSAID induced gastrointestinal complications J. Rheumatol. 1999, 26 (Suppl.) 18-24
4. Adam, K.; Sivropoulou, A.; Kokkini, S.; Lanaras, T.; Arsenakis, M. Antifungal activities of Origanum vulgare subsp. hirtum, Mentha spicata, Lavandula angustifolia, and Salvia fruticosa essential oils against human pathogenic fungi J. Agric. Food Chem. 1998, 46, 1739-1745
5. Kulisic, T.; Radonic, A.; Katalinic, V.; Milos, M. Use of different methods for testing antioxidative activity of oregano essential oil Food Chem. 2004, 85, 633-640
6. 2 J. Agric. Food Chem. 2004, 52, 3042-3047
7. Velluti, A.; Sanchis, V.; Ramos, A. J.; Marin, S. Effect of essential oils of cinnamon, clove, lemon grass, oregano and palmarosa on growth of and fumonisin B1 production by Fusarium verticillioides in maize J. Sci. Food Agric. 2004, 84, 1141-1146
8. Calpouzos, L. Botanical aspects of oregano. J Econ. Bot. 1954, 8, 222-233
9. Lemay, M. Anti-inflammatory phytochemicals: in vitro and ex vivo evaluation. In Phytochemicals; Meskin, M. S.; Bidlack, W. R.; Randolph, R. K., Eds.; CRC Press: Boca Raton, FL, 2006; pp 41 -60.
10. Yoshino, K.; Higashi, N.; Koga, K. Antioxidant and antiinflammatory activities of oregano extract J. Health Sci. 2006, 52, 169-173
11. Koukoulitsa, C.; Zika, C.; Hadjipavlou-Litina, D.; Demopoulos, V. J.; Skaltsa, H. Inhibitory effect of polar oregano extracts on aldose reductase and soybean lipoxygenase in vitro Phytother. Res. 2006, 20, 605-606
12. Ismaili, H.; Tortora, S.; Sosa, S.; Fkih-Tetouani, S.; Ilidrissi, A.; Della Loggia, R.; Tubaro, A.; Aquino, R. Topical anti-inflammatory activity of Thymus willdenowii J. Pharm. Pharmacol. 2001, 53, 1645-1652
13. Petersen, M.; Simmonds, M. S. J. Rosmarinic acid Phytochemistry 2003, 62, 121-125
14. Nakamura, Y.; Ohto, Y.; Murakami, A.; Ohigashi, H. Superoxide scavenging activity of rosmarinic acid from Perilla frutescens Britton var. acuta F. viridis J. Agric. Food Chem. 1998, 46, 4545-4550
15. Fuhrman, B.; Volkova, N.; Rosenblat, M.; Aviram, M. Lycopene synergistically inhibits LDL oxidation in combination with vitamin E, glabridin, rosmarinic acid, carnosic acid, or garlic acid Antioxid. Redox Signal. 2000, 2, 491-506
16. Parnham, M. J.; Kesselring, K. Rosmarinic acid Drugs Future 1985, 10, 756-757
17. Yamamoto, H.; Sakakibara, J.; Nagatsu, A.; Sekiya, K. Inhibitors of arachidonate lipoxygenase from defatted perilla seed J. Agric. Food Chem. 1998, 46, 862-865
18. Liu, J. Pharmacology of oleanolic acid and ursolic acid J. Ethnopharmacol. 1995, 49, 57-68
19. Chen, L.; Zhang, Y.; Kong, X.; Peng, S.; Tian, J. Synthesis and biological evaluation of nitric oxide-releasing derivatives of oleanolic acid as inhibitors of HepG2 cell apoptosis Bioorg. Med. Chem. Lett. 2007, 17, 2979-2982
20. Price, K. R.; Johnson, I. T.; Fenwick, G. R. The chemistry and biological significance of saponins in foods and feeding stuffs Crit. Rev. Food Sci. Nutr. 1987, 26, 27-135
21. Mahato, S. B.; Sarkar, S. K.; Poddar, G. Triterpenoid saponins Phytochemistry 1988, 27, 3037-3067
22. Dai, Y.; Hang, B. Q.; Li, P. Z.; Tan, L. W. Effects of oleanolic acid on immune system and type I allergic reaction Acta Pharmacol. Sin. 1989, 10, 381-384
23. Tsuruga, T.; Chun, Y. T.; Ebizuka, Y.; Sankawa, U. Biologically active constituents of Melaleuca leucadendron: inhibitors of induced histamine release from rat mast cells Chem. Pharmacol. Bull. 1991, 39, 3276-3278
24. Simon, A.; Najid, A.; Chulia, A. J.; Delage, C.; Rigaud, M. Inhibition of lipoxygenase activity and HL60 leukemic cell proliferation by ursolic acid isolated from heather flowers (Calluna vulgaris) Biochim. Biophys. Acta 1992, 1125, 68-72
25. Najid, A.; Simon, A.; Cook, J.; Chable-Rabinovitch, H.; Delage, C.; Chulia, A. J.; Rigaud, M. Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL 60 leukemic cells FEBS J. 1992, 299, 213-217
26. Zhou, C.; Sun, X.; Liu, W.; Shi, H.; Gao, H.; Miao, Y. Effects of oleanolic acid on the immune complex allergic reaction and inflammation J. Clin. Pharmacol. Sci. 1993, 2, 69-79
27. Ying, Q. L.; Rinehart, A. R.; Simon, S. R.; Cheronis, J. C. Inhibition of human leucocyte elastase by ursolic acid Biochem. J. 1991, 277, 521-526
28. Dai, Y.; Hang, B. Q.; Tan, L. W. Anti-inflammatory effect of oleanolic acid Chin. J. Pharmacol. Toxicol. 1989, 3, 96-99
29. Kapil, A.; Shanna, S. Anti-complement activity of oleanolic acid: an inhibitor of C3 tonvertase of the classical complement pathway J. Pharm. Pharmacol. 1994, 46, 922-923
30. Chen, J. H.; Xia, Z. H.; Tan, R. X. High-performance liquid chromatographic analysis of bioactive triterpenes in Perilla frutescens J. Pharm. Biomed. Anal. 2003, 32, 1175-1179
31. Altinier, G.; Sosa, S.; Aquino, R. P.; Mencherini, T.; Della Loggia, R.; Tubaro, A. Characterization of topical antiinflammatory compounds in Rosmarinus officinalis L J. Agric. Food Chem. 2007, 55, 1718-1723
32. Kim, H.; Lee, H. S.; Chang, K. T.; Ko, T. H.; Baek, K. J.; Kwon, N. S. Chloromethyl ketones block induction of nitric oxide synthase in murine macrophages by preventing activation of nuclear factor-κB J. Immunol. 1995, 154, 4741-4748
33. Pan, M. H.; Lin-Shiau, S. Y.; Ho, C. T.; Lin, J. H.; Lin, J. K. Suppression of lipopolysaccharide-induced nuclear factor-κB activity by theaflavin-3,30-digallate from black tea and other polyphenols through down-regulation of IκB kinase activity in macrophages Biochem. Pharmacol. 2000, 59, 357-367
34. Exarchou, V.; Nenadis, N.; Tsimidou, M.; Gerothanassis, I. P.; Troganis, A.; Boskou, D. Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory J. Agric. Food Chem. 2002, 50, 5294-5299
35. Hideyuki, M.; Hideyuki, C.; Chikako, A.; Midori, A.; Teruhiko, Y.; Junya, M. DPPH radical scavengers from dried leaves of oregano (Origanum vulgare) Biosci.,Biotechnol.,Biochem. 2003, 67, 2311-2316
36. Seto, H.; Otake, N.; Luo, S. Q.; Jin, H. F. Studies on chemical constituents of Bupleurum genus. Part I. A new triterpenoid glycoside from Bupleurum chinense DC Agric. Biol. Chem. 1986, 50, 939-942
37. Ahmad, V. U.; Noorwala, M.; Mohammad, F. V.; Sener, B. A new triterpene glycoside from the roots of Symphytum officinale J. Nat. Prod. 1993, 56, 329-334 (Pubitemid 23104343)
38. Huang, P.; Wang, L.; Lin, C. New triterpenoids of Mallotus repandus J. Nat. Prod. 1999, 62, 891-892
39. 13C NMR spectra of four triterpenes of the ursane, artane, lupane and friedelane groups Magn. Reson. Chem. 2000, 38, 201-206
40. Yang, M.; Fazio, S.; Munch, D.; Drumm, P. Impact of methanol and acetonitrile on separations based on p-p interactions with a reversed-phase phenyl column J. Chromatogr., A 2005, 1097, 124-129
41. Dogan, S.; Arslan, O.; Ozen, F. Polyphenol oxidase activity of oregano at different stages Food Chem. 2005, 91, 341-345