Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from rosmarinus officinalis leaves

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 8, 2011, Pages 3674-3685

  Kuo, Chia Feng ^a   Su, Jeng De ^b   Chiu, Chun Hung ^c   Peng, Chiung Chi ^d   Chang, Chi Huang ^c   Sung, Tzu Ying ^b   Huang, Shiau Huei ^c   Lee, Wen Chin ^e   Chyau, Charng Cherng ^c  

^a SHIH CHIEN UNIVERSITY   (Taiwan)

^b TUNGHAI UNIVERSITY   (Taiwan)

^c HUNGKUANG UNIVERSITY   (Taiwan)

^d CHINA MEDICAL UNIVERSITY   (Taiwan)

^e SHOW CHWAN MEMORIAL HOSPITAL   (Taiwan)

Author keywords

anti inflammatory activity; carnosic acid; HPLC MS MS; murine macrophage cell line RAW 264.7; Rosemary; supercritical carbon dioxide extraction

Indexed keywords

ANTI-INFLAMMATORY ACTIVITY; CARNOSIC ACID; HPLC-MS/MS; MURINE MACROPHAGE CELL LINE RAW 264.7; ROSEMARY; SUPERCRITICAL CARBON DIOXIDE EXTRACTION;

CARBON DIOXIDE; CELL CULTURE; EFFLUENT TREATMENT; MACROPHAGES; NITRIC OXIDE; PHENOLS; PHOSPHORYLATION; SUPERCRITICAL FLUIDS;

SUPERCRITICAL FLUID EXTRACTION;

ABIETANE DERIVATIVE; ANTIINFLAMMATORY AGENT; CARBON DIOXIDE; PLANT EXTRACT; SALVIN;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PLANT LEAF; ROSEMARY; TANDEM MASS SPECTROMETRY;

ANTI-INFLAMMATORY AGENTS; CARBON DIOXIDE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DITERPENES, ABIETANE; PLANT EXTRACTS; PLANT LEAVES; ROSMARINUS; TANDEM MASS SPECTROMETRY;

MURINAE; ROSMARINUS OFFICINALIS;

EID: 79955007157     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104837w     Document Type: Article

References (39)

1. Takaki, I.; Bersani-Amado, L. E.; Vendruscolo, A.; Sartoretto, S. M.; Diniz, S. P.; Bersani-Amado, C. A.; Cuman, R. K. N. Anti-inflammatory and antinociceptive effects of Rosmarinus officinalis L. essential oil in experimental animal models J. Med. Food 2008, 11, 741-746
2. Richheimer, S. L.; Bernart, M. W.; King, G. A.; Kent, M. C.; Bailey, D. T. Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary J. Am. Oil. Chem. Soc. 1996, 73, 507-514 (Pubitemid 126547289)
3. Bai, N.; He, Kan.; Roller, M.; Lai, C.-S.; Shao, X.; Pan, M.-H.; Ho, C.-T. Flavonoids and phenolic compounds from Rosmarinus officinalis J. Agric. Food Chem. 2010, 58, 5363-5367
4. Aruoma, O. I.; Haliwell, B.; Aeschbach, R.; Loligers, J. Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid Xenobiotica 1992, 22, 257-268
5. Bicchi, C.; Binello, A.; Rubiolo, P. Determination of phenolic diterpene antioxidant in rosemary (Rosmarinus officinalis L.) with different methods of extraction and analysis Phytochem. Anal. 2000, 11, 236-242 (Pubitemid 30479779)
6. Tena, M. T.; Valcárcel, M.; Hidalgo, P. J.; Ubera, J. L. Supercritical fluid extraction of natural antioxidants from rosemary: comparison with liquid solvent sonication Anal. Chem. 1997, 69, 521-526
7. Wellwood, C. R. L.; Col, R. A. Relevance of carnosic acid concentrations to the selection of rosemary, Rosmarinus officinalis (L.), accessions for optimization of antioxidant yield J. Agric. Food Chem. 2004, 52, 6101-6107
8. Masuda, Y.; Inaba, Y.; Takeda, Y. Antioxidant mechanism of carnosic acid: structural identification of two oxidation products J. Agric. Food Chem. 2001, 49, 5560-5565 (Pubitemid 33089708)
9. Señoráns, F. J.; Ibañez, E.; Cavero, S.; Tabera, J.; Reglero, G. Liquid chromatographic-mass spectrometric analysis of supercritical-fluid extracts of rosemary plants J. Chromatogr., A 2000, 870, 491-499 (Pubitemid 30077454)
10. Ramírez, P.; Señoráns, F. J.; Ibañez, E.; Reglero, G. Separation of rosemary antioxidant compounds by supercritical fluid chromatography on coated packed capillary columns J. Chromatogr., A 2004, 1057, 241-245 (Pubitemid 39463090)
11. 2 extract from the leaves of rosemary Nat. Prod. Res. 2008, 22, 76-90 (Pubitemid 350153974)
12. Ross, R. Atherosclerosis-an inflammatory disease New Engl. J. Med. 1999, 340, 115-126
13. Ohshima, H.; Tatemichi, M.; Sawa, T. Chemical basis of inflammation-induced carcinogenesis Arch. Biochem. Biophys. 2003, 417, 3-11 (Pubitemid 36960042)
14. Poeckel, D.; Greiner, C.; Verhoff, M.; Rau, O.; Tausch, L.; Hornig, C.; Steinhilber, D.; Schubert-Zsilavecz, M.; Werz, O. Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes Biochem. Pharmacol. 2008, 76, 91-97
15. Lo, A. H.; Liang, Y. C.; Lin-Shiau, S. Y.; Ho, C. T.; Lin, J. K. Carnosol, an antioxidant in rosemary, suppresses inducible nitric oxide synthase through down-regulating nuclear factor-κB in mouse macrophages Carcinogenesis 2002, 23, 983-991
16. Peng, C. H.; Su, J. D.; Chyau, C. C.; Sung, T. Y.; Ho, S. S.; Peng, C. C.; Peng, R. Y. Supercritical fluid extracts of rosemary leaves exhibit potent anti-inflammation and anti-tumor effects Biosci. Biotechnol. Biochem. 2007, 71, 2223-32 (Pubitemid 350113116)
17. Bailey, D. T.; Richheimer, S. L.; Bank, V. R.; King, B. T. High Purity Carnosic Acid from Rosemary and Sage Extracts by pH-Controlled Precipitation. US Patent 5,859,293, 1999.
18. Cuvelier, M. E.; Berset, C.; Richard, H. Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary J. Am. Oil Chem. Soc. 1996, 73, 645-652 (Pubitemid 126606659)
19. Zielinski, H.; Kozlowska, H. Antioxidant activity and total phenolics in selected cereal grains and their different morphological fractions J. Agric. Food Chem. 2000, 48, 2008-2016 (Pubitemid 30431180)
20. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63 (Pubitemid 14203433)
21. Chen, Q.; Shi, H.; Ho, C.-T. Effects of rosemary extracts and major constituents on lipid oxidation and soybean lipoxygenase activity J. Am. Oil Chem. Soc. 1992, 69, 999-1002
22. Grayer, R. J.; Bryan, S. E.; Veitch, N. C.; Goldstone, F. J.; Paton, A.; Wollenweber, E. External flavones in sweet basil, Ocimum basilicum, and related taxa Photochemistry 1996, 43, 1041-1047
23. Hase, T.; Ohtani, K.; Kasai, R.; Yamasaki, K.; Picheansoonthon, C. Revised structure for hortensin, a flavonoid from Millingtonia hortensis Phytochemistry 1995, 40, 287-290
24. Gilmore, T. D. Introduction to NF-κB: players, pathways, perspectives Oncogene 2006, 25, 6680-6684 (Pubitemid 44657845)
25. Ibañez, E.; Kubatova, A.; Senorans, F. J.; Cavero, S.; Reglero, G.; Hawthorne, S. B. Subcritical water extraction of antioxidant compounds from rosemary plants J. Agric. Food. Chem. 2003, 51, 375-382
26. Almela, L.; Sánchez-Muñoz, B.; Fernández- López, J. A.; Roca, M. J.; Rabe, V. Liquid chromatograpic-mass spectrometric analysis of phenolics and free radical scavenging activity of rosemary extract from different raw material J. Chromatogr., A 2006, 1120, 221-229 (Pubitemid 43866768)
27. Hasrat, J. A.; Pieters, L.; Claeys, M.; Vlietinck, A. Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis J. Nat. Prod. 1997, 60, 638-641 (Pubitemid 27274390)
28. Huck, W. C.; Huber, G. C.; Ongania, K. H.; Bonn, K. G. Isolation and characterization of methoxylated flavones in the flowers of Primula veris by liquid chromatography and mass spectrometry J. Chromatogr., A 2000, 870, 453-462
29. Santoyo, S.; Cavero, S.; Jaime, L.; Ibañez, E.; Señoráns, F. J.; Reglero, G. Chemical composition and antimicrobial activity of Rosmarinus officinalis L. essential oil obtained via supercritical fluid extraction J. Food Prot. 2005, 68, 790-795 (Pubitemid 40518852)
30. Ramirez, P.; Garcia-Risco, M. R.; Santoyo, S.; Seronans, F. J.; Ibañez, E.; Reglero, G. Isolation of functional ingredients from rosemary by preparative-supercritical fluid (Prep-SFC) J. Pharm. Biomed. Anal. 2006, 41, 1606-1613 (Pubitemid 44247460)
31. Mata, A. T.; Proenc, C.; Ferreira, A. R.; Serralheiro, M. L. M.; Nogueira, J. M. F.; Araujo, M. E. M. Antioxidant and antiacetylcholinesterase activities of five plants used as Portuguese food spices Food Chem. 2007, 103, 778-786 (Pubitemid 46283223)
32. Moon, J. K.; Shibamoto, T. Antioxidant assays for plant and food components J. Agric. Food Chem. 2009, 57, 1655-1666
33. Cavero, S.; Jaime, L.; Martín-Álvarez, P. J.; Señoráns, F. J.; Reglero, G.; Ibañez, E. In vitro antioxidant analysis of supercritical fluid extracts from rosemary (Rosmarinus officinalis L.) Eur. Food Res. Technol. 2005, 221, 478-486 (Pubitemid 41203832)
34. Ono, M.; Morinaga, H.; Masuoka, C.; Ikeda, T.; Okawa, M.; Kinjo, J.; Nohra, T. New bisabolane-type sesquiterpenes from the aerial parts of Lippia dulcis Chem. Pharm. Bull. 2005, 53, 1175-1177 (Pubitemid 41330485)
35. Yin, Y.; Gong, F. Y.; Wu, X. X.; Sun, Y.; Li, Y. H.; Chen, T.; Xu, Q. Anti-inflammatory and immunosuppressive effect of flavones isolated from Artemisia vestita J. Ethnopharmacol. 2006, 120, 1-6
36. Schroeder, R. A.; Kuo, P. C. Nitric oxide: physiology and pharmacology Anesth Analg. (Hagerstown, MD, U. S.) 1995, 81, 1052-1059
37. Locksley, R. M.; Killeen, N.; Lenardo, M. J. The TNF and TNF receptor superfamilies: integrating mammalian biology Cell 2001, 104, 487-501 (Pubitemid 32201945)
38. Smith, W. L.; Langenach, R. Why there are two cyclooxygenase isozymes J. Clin. Invest. 2001, 107, 1491-1495 (Pubitemid 32574631)
39. Baldwin, A. S., Jr. The NF-κB and IκB proteins: new discoveries and insights Annu. Rev. Immunol. 1996, 14, 649-681 (Pubitemid 126664210)