Abstract
Phytochemical investigations of different species of Lamiaceae family (rosemary-Rosmarinus officinalis L., sage-Salvia officinalis L., winter savory-Satureja montana L., clary sage-Salvia sclarea L. and sticky sage-Salvia glutinosa L.), using gas chromatography and mass spectrometry (GC-MS) were performed. The studies were focused on oleanolic, betulinic and ursolic acid. Since oleanolic and ursolic acid are position isomers with very similar structures, the difficulties in their separation and identification have been reported by several authors. However, both compounds can be well distinguished by order of elution during gas chromatography and by intensities of the fragment ion signals in their mass spectra, where the retro-Diels-Alder reaction was primarily observed. A combination of ultrasonic extraction, solid phase extraction, size exclusion chromatography, trimethylsilylation, and GC-MS resulted in simultaneous separation, identification and quantification of the mentioned compounds. The compounds have been identified by retention time and comparison of mass spectra with those of pure standards. The mass spectral fragmentation behavior of all three derivatised acids was investigated. The obtained characteristic fragment patterns are discussed in the presented work. Good linearity over the concentration range 1–50 mg L−1 for all three compounds was confirmed. The correlation coefficients (r 2) were in the range of 0.9980–0.9983. Quantitative analyses of different Lamiaceae extracts showed that the oleanolic acid content ranged from 0.09 to 0.9% dry weight, content of betulinic acid ranged from traces to 0.6%, and that of ursolic acid varied from 0.09 to 1.6% dry weight.
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References
Suhaj M (2006) J Food Compos Anal 19:531–537
Brglez T (2002) Master Degree Thesis, University of Ljubljana
Freire CSR, Silvestre AJD, Neto CP, Cavaleiro JAS (2002) Holzforschung 56:372–379
Gbaguidi F, Accrombessi G, Moudachirou M, Quetin-Leclercq J (2005) J Pharm Biomed Anal 39:990–995
Janicsák G, Veres K, Kakasy AZ, Máthé I (2006) Biochem Syst Ecol 34:392–396
Janicsák G, Veres K, Kállai M, Máthé I (2003) Chromatographia 58:295–299
Liao LP, Li SL, Li P (2005) J Sep Sci 28:2061–2066
Liu J (1995) J Ethnopharmacol 49:57–68
Ghosh A, Misra S, Dutta AK, Choudhury A (1985) Phytochemistry 24:1725–1727
Burnouf-Radosevich M, Delfel NE, England R (1985) Phytochemistry 24:2063–2066
Claude B, Morin Ph, Lafosse M, Andre P (2004) J Chromatogr A 1049:37–42
Chen JH, Xia ZH, Tan RX (2003) J Pharm Biomed Anal 32:1175–1179
Kessler JH, Mullauer FB, De Roo GM, Medema JP (2007) Cancer Lett 251:132–145
Burnouf-Radosevich M, Delfel NE (1984) J Chromatogr A 292:403–409
Zhao G, Yan W, Cao D (2007) J Pharm Biomed Anal 43:959–962
De Oliveira BH, Santos CAM, Espindola APDM (2002) Phytochem Anal 13:95–98
Cui T, Li JZ, Kayahara H, Ma L, Wu LX, Nakamura K (2006) J Agric Food Chem 54:4574–4581
Van der Doelen GA, Van den Berg KJ, Boon JJ, Shibayama N, De la Rie ER, Genuit WJL (1998) J Chromatogr A 809:21–37
Shin YG, Cho KH, Chung SM, Graham J, Das Gupta TK, Pezzuto JM (1999) J Chromatogr B 732:331–336
Lacikova L, Abdel-Hamid ME, Novotny L, Masterova I, Grancai D (2006) Chromatographia 63:117–122
Razboršek MI, Brodnjak-Vončina D, Doleček V, Vončina E (2007) Acta Chim Slov 54:60–67
Mathe C, Culioli G, Archier P, Vieillescazes C (2004) J Chromatogr A 1023:277–285
Galgon T, Höke D, Dräger B (1999) Phytochem Anal 10:187–190
Colombini MP, Modugno F, Giannarelli S, Fuoco R, Matteini M (2000) Microchem J 67:385–396
Pérez-Camino MC, Cert A (1999) J Agric Food Chem 47:1558–1562
Taipale HT, Lapinjoki SP (1991) Phytochem Anal 2:84–86
Vilegas JHY, Lanças FM, Vilegas W, Pozetti GL (1997) J Braz Chem Soc 8:529–535
Oleszek (2002) J Chromatogr A 967:147–162
Mathe C, Culioli G, Archier P, Vieillescazes C (2004) Chromatographia 60:493–499
Berangere C, Caussarieu N, Morin P, Morin-Allory L, Lafosse M (2004) J Sep Sci 27:964–970
Cheng X, Shin YG, Levine BS, Smith AC, Tomaszewski JE, Van Breemen RB (2003) Rapid Commun Mass Spectrom 17:2089–2092
Budzikiewicz H, Djerassi C, Williams DH (1964) Pentacyclic triterpenes. In: Structure elucidation of natural products by mass spectrometry. Holden-day, San Francisco, pp 121–140
McLafferty FW, Tureček F (1993) Basic mechanisms of ion fragmentation. In: Kelly A (ed) Interpretation of mass spectra. University Science Books, California, pp 51–83
Enzell CR, Wahlberg I (1980) Terpenes and terpenoids. In: Waller GR, Dermer OC (eds) Biochemical applications of mass spectrometry. Wiley-Interscience, New York, pp 311–406
Munné-Bosch S, Alegre L (2001) Plant Physiol 125:1094–1102
Del Baño MJ, Lorente J, Castillo J, Benavente-García O, Marín MP, del Río JA, Ortuño A, Ibarra I (2004) J Agric Food Chem 51:4247–4253
Munné-Bosch S, Alegre L, Schwarz K (2000) Eur Food Res Technol 210:263–267
Raffo A, la Malfa G, Fogliano V, Maiani G, Quaglia G (2006) J Food Compos Anal 19:11–19
Antolovich M, Prenzler P, Robards K, Ryan D (2000) Analyst 125:989–1009
Brandšteterová E, Žiaková-Čaniová A (2002) Phenolic acids in natural plants: analysis by HPLC. In: Cazes J (ed) Encyclopedia of chromatography. Marcel Dekker, New York, pp 115–151
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Razboršek, M.I., Vončina, D.B., Doleček, V. et al. Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives. Chroma 67, 433–440 (2008). https://doi.org/10.1365/s10337-008-0533-6
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DOI: https://doi.org/10.1365/s10337-008-0533-6