Effect of the solvent and the sample preparation on the determination of triterpene compounds in two-phase olive-mill-waste samples

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 17, 2015, Pages 4269-4275

  Fernández Hernández, Antonia ^a   Martinez, Antonio ^b   Rivas, Francisco ^b   García Mesa, Jose A ^a   Parra, Andres ^b  

^a IFAPA CENTRO EL TORUÑO   (Spain)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

linoleic acid; maslinic acid; oleanolic acid; triterpene diols; two phase olive mill waste alperujo; ursolic acid

Indexed keywords

CARBOXYLIC ACIDS; DRYING; FATTY ACIDS; LINOLEIC ACID; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHANOL; OIL SHALE; OLIVE OIL; VOLATILE FATTY ACIDS;

MASLINIC ACIDS; OLEANOLIC ACIDS; TRITERPENES; TWO-PHASE OLIVE MILL WASTE; URSOLIC ACID;

EXTRACTION;

PLANT EXTRACT; TRITERPENE; WASTE;

ANALYSIS; CHEMISTRY; DEVICES; EVALUATION STUDY; FOOD HANDLING; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; OLIVE TREE; PROCEDURES; WASTE;

CHEMICAL FRACTIONATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOOD HANDLING; MASS SPECTROMETRY; OLEA; PLANT EXTRACTS; TRITERPENES; WASTE PRODUCTS;

EID: 84928920224     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf506171y     Document Type: Article

References (33)

1. FAOSTAT Resource Statistics; FAOSTAT: Rome, 2014. faostat3.fao.org (accessed December 2014).
2. López-Piñeiro, A.; Albarrán, A.; Rato Nunes, J. M.; Peña, D.; Cabrera, D. Long-term impacts of de-oiled two-phase olive mill waste on soil chemical properties, enzyme activities, and productivity in an olive grove Soil Tillage Res. 2011, 114, 175-182
3. Roig, A.; Cayuela, M. L.; Sánchez-Monedero, M. A. An overview on olive mil wastes and their valorisation methods Waste Manage. 2006, 26, 960-969
4. Sabatini, N. Recent patents in olive oil industry: New technologies for the recovery of phenols compounds from olive oil, olive oil industrial byproducts, and waste waters Recent Pat. Food, Nutr. Agric. 2010, 2, 154-159
5. Fernández-Bolaños, J.; Rodríguez, G.; Rodríguez, R.; Guillén, R.; Jiménez, A. Extraction of interesting organic compounds from olive oil waste Grasas Aceites 2006, 57, 95-106
6. Bouzid, O.; Navarro, D.; Roche, M.; Asther, M.; Haon, M.; Delattre, M.; Lorquin, J.; Laba, M.; Asther, M.; Lesage-Meessen, L. Fungal enzymes as a powerful tool to release simple phenolic compounds from olive oil byproduct Process Biochem. 2005, 40, 1855-1862
7. Fernández-Bolaños, J.; Rodríguez, G.; Gómez, E.; Guillén, R.; Jiménez, A.; Heredia, A.; Rodríguez, R. Total recovery of the waste of two-phase olive oil processing: Isolation of added-value compounds J. Agric. Food Chem. 2004, 52, 5849-5855
8. Cardoso, A. M.; Coimbra, M. A.; Da Silva, J. A. L. Calcium-mediated gelation of an olive pomace pectic extract Carbohydr. Polym. 2003, 52, 125-133
9. Garcia-Granados, A. Preparation of mannitol and its derivatives from branches, leaves, juice, and peduncles of olives. Spanish Patent 2056745, 1994.
10. Calero, J.; Martínez, L.; Garcia-Granados, A. Countercurrent extraction process for recovering acids, phenols, alcohols, and their derivatives, from olive-pressing waste. Spanish Patent 2051238, 1994.
11. Sanchez-Quesada, C.; Lopez-Biedma, A.; Warleta, F.; Campos, M.; Beltran, G.; Gaforio, J. J. Bioactive properties of the main triterpenes found in olives, virgin olive oil, and leaves of Olea europaea J. Agric. Food Chem. 2013, 61, 12173-12182
12. Garcia-Granados, A. Process for the industrial recovery of oleanolic and maslinic acids contained in the olive milling subproducts. PCT Int. Appl. 9804331, 1998.
13. Parra, A.; López, P. E.; Garcia-Granados, A. Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive-oil industry Chem. Biodivers. 2010, 7, 421-439
14. Salvador, J. A. R.; Leal, A. S.; Alho, D. P. S.; Goncalves, B. M. F.; Valdeira, A. S.; Mendes, V. I. S.; Jing, Y. Highlights of pentacyclic triterpenoids in the cancer settings Stud. Nat. Prod. Chem. 2014, 41, 33-73
15. Parikh, N. R.; Mandal, A.; Bhatia, D.; Siveen, K. S.; Sethi, G.; Bishayee, A. Oleanane triterpenoids in the prevention and therapy of breast cancer: Current evidence and future perspectives Phytochem. Rev. 2014, 13, 793-810
16. Wolska, K. I.; Grudniak, A. M.; Fiecek, B.; Kraczkiewicz-Dowjat, A.; Kurek, A. Antibacterial activity of oleanolic and ursolic acids and their derivatives Cent. Eur. J. Biol. 2010, 5, 543-553
17. Fernandez-Navarro, M.; Peragon, J.; Esteban, F. J.; Amores, V.; de la Higuera, M.; Lupianez, J. A. Maslinic acid: A component of olive oil on growth and protein-turnover rates. In Olives and Olive Oil in Health and Disease Prevention; Preedy, V. R.; Watson, R. R., Eds.; Elsevier: London, 2010; pp 1415-1421.
18. Rodriguez-Rodriguez, R.; Ruiz-Gutierrez, V. Vasorelaxant effects of oleanolic acid and erythrodiol in pomace olive oil. In Olives and Olive Oil in Health and Disease Prevention; Preedy, V. R.; Watson, R. R., Eds.; Elsevier: London, 2010; pp 813-820.
19. Ikeda, Y.; Murakami, A.; Ohigashi, H. Ursolic acid: An anti- and pro-inflammatory triterpenoid Mol. Nutr. Food Res. 2008, 52, 26-42
20. Sultana, N.; Ata, A. Oleanolic acid and related derivatives as medicinally important compounds J. Enzyme Inhib. Med. Chem. 2008, 23, 739-756
21. Zhang, S.; Sun, Y.; Sun, Z.; Wang, X.; You, J.; Suo, Y. Determination of triterpenic acids in fruits by a novel high performance liquid chromatography method with high sensitivity and specificity Food Chem. 2014, 146, 264-269
22. Hao, Y.; Chen, X.; Hu, S.; Bai, X. Solvent bar microextraction with HPLC for determination and protein-binding characteristics of oleanolic acid and ursolic acid Chromatographia 2014, 77, 359-363
23. Wójciak-Kosior, M.; Sowa, I.; Kocjan, R.; Nowak, R. Effect of different extraction techniques on quantification of oleanolic and ursolic acid in Lamii albi flos Ind. Crops Prod. 2013, 44, 373-377
24. Xu, H.; Shi, X. W.; Ji, X.; Du, Y.; Zhu, H.; Zhang, L. A rapid method for simultaneous determination of triterpenoid saponins in Pulsatilla turczaninovii using microwave-assisted extraction and high performance liquid chromatography-tandem mass spectrometry Food Chem. 2012, 135, 251-258
25. Pollier, J.; Goossens, A. Oleanolic acid Phytochem. 2012, 77, 10-15
26. Li, G. L.; You, J. M.; Song, C. H.; Xia, L.; Zheng, J.; Suo, Y. R. Development of a new HPLC method with precolumn fluorescent derivatization for rapid, selective, and sensitive detection of triterpenic acids in fruits J. Agric. Food Chem. 2011, 59, 2972-2979
27. Guo, S.; Duan, J.; Tang, Y.; Qian, Y.; Zhao, J.; Qian, D.; Su, S.; Shang, E. Simultaneous qualitative and quantitative analysis of triterpenic acids, saponins, and flavonoids in the leaves of two Ziziphus species by HPLC-PDA-MS/ELSD J. Pharm. Biomed. Anal. 2011, 56, 264-270
28. Sánchez-ávila, N.; Priego-Capote, F.; Ruiz-Jiménez, J.; Luque de Castro, M. D. Fast and selective determination of triterpenic compounds in olive leaves by liquid chromatography-tandem mass spectrometry with multiple reaction monitoring after microwave-assisted extraction Talanta 2009, 78, 40-48
29. Goulas, V.; Manganaris, G. A. Towards an efficient protocol for the determination of triterpenic acids in olive fruit: A comparative study of drying and extraction methods Phytochem. Anal. 2011, 23, 444-449
30. Romero, C.; García, A.; Medina, E.; Ruíz-Méndez, M. V.; de Castro, A.; Brenes, M. Triterpenic acids in table olives Food Chem. 2010, 118, 670-674
31. Guinda, A.; Rada, M.; Delgado, T.; Gutierrez-Adánez, P.; Castellano, J. M. Pentacyclic triterpenoids from olive fruit and leaf J. Agric. Food Chem. 2010, 58, 9658-9691
32. Parra, A.; Rivas, F.; López, P. E.; Garcia-Granados, A.; Martinez, A.; Albericio, F.; Marquez, N.; Muñoz, E. Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides Bioorg. Med. Chem. 2009, 17, 1139-1145
33. Tarvainen, M.; Suomela, J. P.; Kallio, H.; Yang, B. Triterpenic acids in Plantago major: Identification, quantification, and comparison of different extraction methods Chromatographia 2010, 71, 279-284