Comparison between methyl and trimethylsilyl ester derivatives in the separation and GC quantification of triterpene acids in Eugenia brasiliensis leaf extract

Chromatographia

Volumn 77, Issue 7-8, 2014, Pages 629-635

  Lima, Adélia Mara Belém ^a   D'Avila, Luiz Antonio ^b   Siani, Antonio Carlos ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Eugenia brasiliensis; Gas chromatography; Methyl ester derivatives; Trimethylsilyl derivatives; Triterpene acids; Ursolic acid

Indexed keywords

ALCOHOL; BETULIC ACID; ESTER DERIVATIVE; METHYL ESTER; OLEANOLIC ACID; PLANT EXTRACT; SODIUM HYDROXIDE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL ESTER; TRITERPENE; UNCLASSIFIED DRUG; URSOLIC ACID;

ARTICLE; CHEMICAL STRUCTURE; EUGENIA; GAS CHROMATOGRAPHY; NONHUMAN; PLANT LEAF; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ROOM TEMPERATURE; SEPARATION TECHNIQUE; TANDEM MASS SPECTROMETRY;

EID: 84897523333     PISSN: 00095893     EISSN: 16121112     Source Type: Journal    
DOI: 10.1007/s10337-014-2659-z     Document Type: Article

References (28)

1. Liu J (2005) Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol 100:92-94
2. Laszczyk MN, Jäger S, Simon-Haarthaus B, Scheffler A, Schempp CM (2006) Physical, chemical and pharmacological characterization of new oleogel-forming triterpene extract from the outer bark birch (Betula cortex). Planta Med 72:1389-1395
3. Jäger S, Laszczyk MN, Strüh CM, Martin SF, Scheffler A (2008) Triterpenes from natural sources for parenteral and topical application. Planta Med 74:1119
4. Jäger S, Trojan H, Kopp T, Laszczyk MN, Scheffler A (2009) Pentacyclic triterpene distribution in various plants-rich sources for a new group of multi-potent plant extracts. Molecules 14:2016-2031
5. Szakiel A, Czkowski P, Pensec F, Bertsch C (2012) Fruit cuticular waxes as a source of biologically active triterpenoids. Phytochem Rev 11(2-3):263-284
6. Gu J-Q, Wang Y, Franzblau SG, Montenegro G, Timmermann BN (2006) Dereplication of pentacyclic triterpenoids in plants by GC-EI/MS. Phytochem Anal 17:102-106
7. Zhang Y, Xue K, Zhao EY, Li Y, Yao L, Yang X, Xie X (2013) Determination of oleanolic acid and ursolic acid in Chinese medicinal plants using HPLC with PAH polymeric C18. Pharmacogn Mag 9(36):19-24
8. Galgon T, Höke D, Dräger B (1999) Identification and quantification of betulinic acid. Phytochem Anal 10:187-190
9. Janicsák G, Veres K, Kállai M, Máthé I (2003) Gas chromatography method for routine determination of oleanolic and ursolic acids in medicinal plants. Chromatographia 58:295-299
10. Burnouf-Radosevich M, Delfel NE, England R (1985) Gas chromatography-mass spectrometry of oleanane- and ursane-type triterpenes - application to Chenopodium quinoa triterpenes. Phytochemistry 24:2063-2066
11. Razborsek MI, Voncina DB, Dolecek V, Voncina E (2008) Determination of oleanolic, betulinic and ursolic acid in Lamiaceae and mass spectral fragmentation of their trimethylsilylated derivatives. Chromatographia 67:433-440
12. Frighetto N, Welendorf MR, Silva AMP, Nakamura MJ, Siani AC (2005) Aplicação de cromatografia centrífuga de contra-corrente na purificação de ácido ursólico das folhas de Eugenia brasiliensis Lam. Rev Bras Farmacogn 15:338-343
13. Frighetto RTS, Welendorf RM, Nigro EM, Frighetto N, Siani AC (2007) Isolation of ursolic acid from apple peels by high speed counter-current chromatography. Food Chem 106:767-771
14. Assimopoulou AN, Papageorgiou VP (2005) GC-MS analysis of penta- and tetracyclic triterpenes from resins of Pistacia species. Part I Pistacia lentiscus var. Chia. Biomed Chromatogr 19:285-311
15. Ávila NS, Capote FP, de Castro MDL (2007) Ultrasound-assisted extraction and silylation prior to gas chromatography-mass spectrometry for the characterization of the triterpene fraction in olive leaves. J Chromatogr A 1165:158-165
16. Guinda A, Rada M, Delgado T, Gutierrez-Adanez P, Castellano JM (2010) Pentacyclic triterpenoids from olive fruit and leaf. J Agric Food Chem 58:9685-9691
17. Guinda A, Rada M, Delgado T, Castellano JM (2011) Pentacyclic triterpenic acids from Argania spinosa. Eur J Lipid Sci Technol 113:231-237
18. Pérez-Camino MC, Cert A (1999) Quantitative determination of hydroxypentacyclic triterpene acids in vegetable oils. J Agric Food Chem 47:1558-1562
19. Razborsek MI, Voncina DB, Dolecek V, Voncina E (2007) Determination of major phenolic acids, phenolic diterpenes and triterpenes in rosemary (Rosmarinus officinalis L.) by gas chromatography and mass spectrometry. Acta Chim Slov 54:60-67
20. Jäger S, Winkler K, Pfüller U, Scheffler A (2007) Solubility studies of oleanolic acid and betulinic acid in aqueous solutions and plant extracts of Viscum album L. Planta Med 73:157-162
21. Huelin FE (1959) Studies on the natural coating of apples. IV. The nature of cutin. Aust J Biol Sci 12:175-180
22. Magina MDA, Dalmarco EM, Dalmarco JB, Colla G, Pizzolatti MG, Brighente MC (2012) Bioactive triterpenes and phenolics of leaves of Eugenia brasiliensis. Quím Nova 35:1184-1188
23. Lima AB, Siani AC, Tappin MR, Nakamura MJ, D'avila LA. (2013) Método em CG-DIC para quantificar ácidos triterpênicos em extratos vegetais utilizando N-(trimetilsilil)imidazol. Congresso XXII SPMB, Brasil. http://www.ufrgs.br/spmb2012/porAutor.html. Accessed 01 Jan 2014
24. Hinshaw JV (2004) Optimization of separation and computer assistance. In: Grob RL, Barry EF (eds) Modern practice of gas chromatography, 4th edn. Wiley, New York
25. Glen AT, Lawrie W, Mclean J, El-Garby Younes M (1967) Triterpenoid constituents of Rose-bay Willow-herb. J Chem Soc C 1967:510-515
26. Younes M (1970) Isolation of 2 alpha-hydroxyursolic acid from the leaves of Backhousia angustifolia F. muell. Indian J Chem 8(9):853-854
27. Pereira SI, Freire CS, Pascoal Neto C, Silvstre AJ, Silva AM (2005) Chemical composition of the epicuticular wax from the fruits of Eucalyptus globulus. Phytochem Anal 16(5):364-369
28. Ellgardt K. (2006) Triterpenes in apple cuticle of organically and IP cultivated apples. Alnarp, Sweden. http://exepsilon.slu.se:8080/archive/ 00001291/01/Karin-Ellgardt-Bachelor.pdf. Accessed 16 Jan 2014