Stability studies on trans-rosmarinic acid and GC-MS analysis of its degradation product

Journal of Pharmaceutical and Biomedical Analysis

Volumn 55, Issue 5, 2011, Pages 1010-1016

  Razboršek, Maša Islamčević ^a  

^a UNIVERSITY OF MARIBOR   (Slovenia)

Author keywords

Cis rosmarinic acid; Gas chromatography; Mass spectrometry; Stability tests; Trans rosmarinic acid

Indexed keywords

ALCOHOL; METHANOL; OXIDIZING AGENT; ROSMARINIC ACID; ROSMARINUS OFFICINALIS EXTRACT; SOLVENT; TETRAHYDROFURAN;

ACCURACY; ANALYSIS; ANGIOSPERM; ARTICLE; CONTROLLED STUDY; DARKNESS; DRUG DEGRADATION; DRUG DETERMINATION; DRUG STRUCTURE; GAS CHROMATOGRAPHY; HUMIDITY; ISOMER; ISOMERIZATION; LIMIT OF DETECTION; LIMIT OF QUANTITATION; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; ROSEMARY; SOLID STATE; STRESS; SUNLIGHT; TEMPERATURE; VALIDATION PROCESS;

CALIBRATION; CHEMISTRY TECHNIQUES, ANALYTICAL; CHEMISTRY, PHARMACEUTICAL; CINNAMATES; DEPSIDES; ETHANOL; FURANS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOMERISM; LIMIT OF DETECTION; METHANOL; MODELS, CHEMICAL; REPRODUCIBILITY OF RESULTS; SOLVENTS; TEMPERATURE;

EID: 79956120312     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.04.003     Document Type: Article

References (35)

1. Petersen M., Simmonds M.S.J. Rosmarinic acid. Phytochemistry 2003, 62:12-125.
2. Boyadzhiev L., Dimitrova V. Extraction and liquid membrane preconcentration of rosmarinic acid from lemon balm (Melissa officinalis L.). Sep. Sci. Technol. 2006, 41:877-886.
3. Tóth J., Mrlianová M., Tekeľová D., Koreňová M. Rosmarinic acid - an important phenolic active compound of lemon balm (Melissa officinalis L.). Acta Fac. Pharm. Univ. Comen. 2003, 50:139-146.
4. Reschke Z. Capillargaschromatographische Bestimmung der Rosmarinsaure in Blattgewurzen. Z. Lebensm. Unters. Forsch. 1983, 176:116-119.
5. Al-Sereiti M.R., Albu-Amer K.M., Sen P. Pharmacology of rosemary (Rosmarinus officinalis Linn.) and its therapeutic potentials. Indian J. Exp. Biol. 1999, 37:124-131.
6. Osakabe N., Takano H., Sanbongi C., Yasuda A., Yanagisawa R., Inoue K., Yoshikawa T. Anti-inflammatory and anti-allergic effect of rosmarinic acid (RA); inhibition of seasonal allergic rhinoconjunctivitis (SAR) and its mechanism. BioFactors 2004, 21:127-131.
7. Takeda H., Tsuji M., Inazu M., Egashira T., Matsumiya T. Rosmarinic acid and caffeic acid produce antidepressive-like effect in the forced swimming test in mice. Eur. J. Pharmacol. 2002, 449:261-267.
8. Erkan N., Ayranci G., Ayranci E. Antioxidant activities of rosemary (Rosmarinus officinalis L.) extract blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol. Food Chem. 2008, 110:76-82.
9. Hooker C.W., Lott W.B., Harrich D. Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription. J. Virol. 2001, 75:3095-3104.
10. Sanbongi C., Takano H., Osakabe N., Sasa N., Natsume M., Yanagisawa R., Inoue K.I., Sadakane K., Ichinose T., Yoshikawa T. Rosmarinic acid in perilla extract inhibits allergic inflammation induced by mite allergen, in a mouse model. Clin. Exp. Allergy 2004, 34:971-977.
11. Lee J., Kim Y.S., Park D. Rosmarinic acid induces melanogenesis through protein kinase A activation signalling. Biochem. Pharmacol. 2007, 74:960-968.
12. Osakabe N., Yasuda A., Natsume M., Yoshikawa T. Rosmarinic acid inhibits epidermal inflammatory responses: anti-carcinogenenic effects of Perilla frutescens extract in the murine two-stage skin mode. Carcinogenesis 2004, 25:549-557.
13. Caniova E., Brandsteterova J. HPLC analysis of phenolic acids in Melissa officinalis. J. Liq. Chromatogr. Relat. Technol. 2001, 24:2647-2659.
14. Areias F.M., Valentão P., Andrade P.B., Moreira M.M., Amaral J., Seabra R.M. HPLC/DAD analysis of phenolic compounds from lavender and its application to quality control. J. Liq. Chromatogr. Relat. Technol. 2000, 23:2563-2572.
15. Brandšteterová E., Žiaková-Čaniová A. Phenolic acids in natural plants: analysis by HPLC. Encyclopedia of Chromatography 2002, 115-151. Marcel Dekker Inc., New York. J. Cazes (Ed.).
16. Del Baño M.J., Lorente J., Castillo J., Benavente-García O., del Río J.A., Ortuño A., Quirin K.W., Gerard D. Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity. J. Agric. Food Chem. 2003, 51:4247-4253.
17. Wang H., Provan G.J., Helliwell K. Determination of rosmarinic acid and caffeic acid in aromatic herbs by HPLC. Food Chem. 2004, 87:307-311.
18. Bandoniene D., Murkovic M. The detection of radical scavenging compounds in crude extract of borage (Borago officinalis L.) by using an on-line HPLC-DPPH method. J. Biochem. Biophys. Methods 2002, 53:45-49.
19. Čuláková V., Máriássyová M., Heilerová L. Comparison of sources of rosmarinic acid. Chem. Listy 2005, 99:s277-s278.
20. Troncoso N., Sierra H., Carvajal L., Delpiano P., Günther G. Fast high performance liquid chromatography and ultraviolet-visible quantification of principal phenolic antioxidants in fresh rosemary. J. Chromatogr. A 2005, 1100:20-25.
21. Zgórka G., Głowniak K. Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family. J. Pharm. Biomed. Anal. 2001, 26:79-87.
22. Liu A.H., Li L., Xu M., Lin Y.H., Guo H.Z., Guo D.A. Simultaneous quantification of six major phenolic acids in the roots of Salvia miltiorrhiza and four related Chinese medicinal preparations by HPLC-DAD method. J. Pharm. Biomed. Anal. 2006, 41:48-56.
23. Razboršek M.I., Brodnjak-Vončina D., Doleček V., Vončina E. Determination of oleanolic, betulinic and ursolic acid in Lamiaceae and mass spectral fragmentation of their trimethylsilylated derivatives. Chromatographia 2008, 67:433-440.
24. Robbins R.J. Phenolic acids in foods: an overview of analytical methodology. J. Agric. Food Chem. 2003, 51:2866-2887.
25. Tsao R., Deng Z. Separation procedures for naturally occurring antioxidant phytochemicals. J. Chromatogr. B 2004, 812:85-99.
26. Molnár-Perl I., Horváth K., Bartha R. GC-MS quantitation of benzoic and aralkyl carboxylic acids as their trimethylsilyl derivatives: in model solutions I. Chromatographia 1998, 48:101-110.
27. Proestos C., Sereli D., Komaitis M. Determination of phenolic compounds in aromatic plants by RP-HPLC and GC-MS. Food Chem. 2006, 95:44-52.
28. Buiarelli F., Cartoni G., Coccioli F., Levetsovitou Z. Determination of phenolic acids in wine by high-performance liquid chromatography with a microbore column. J. Chromatogr. A 1995, 695:229-235.
29. Chu T.Y., Chang C.H., Liao Y.C., Chen Y.C. Microwave-accelerated derivatization processes for the determination of phenolic acids by gas chromatography-mass spectrometry. Talanta 2001, 54:1163-1171.
30. Mallouchos A., Georgios L., Komaitis M. A rapid microwave-assisted derivatization process for the determination of phenolic acids in brewer's spent grains. Food Chem. 2007, 102:606-611.
31. Kivilompolo M., Obůrka V., Hyötyläinen T. Comparison of GC-MS and LC-MS methods for the analysis of antioxidant phenolic acids in herbs. Anal. Bioanal. Chem. 2007, 388:881-887.
32. Antolovich M., Prenzler P., Robards K., Ryan D. Sample preparation in the determination of phenolic compounds in fruits. Analyst 2000, 125:989-1009.
33. Trute A., Nahrstedt A. Separation of rosmarinic acid enantiomers by three different chromatographic methods (HPLC, CE, GC) and determination of rosmarinic acid in Hedera helix L. Phytochem. Anal. 1996, 7:204-208.
34. U.S. Food and Drug Administration, ICH Guidelines on Validation of Analytical Procedures: Text and Methodology Q2 (R1), Federal Register, FDA, Silver Spring, 2005.
35. International Federation of Pharmaceutical Manufactures & Associations, ICH Stability Testing of New Drug Substances and Products Q1A (R2), International Conference on Harmonization, Geneva, 2003.