Time course of pentacyclic triterpenoids from fruits and leaves of olive tree (Olea europaea L.) cv. Picual and cv. Cornezuelo during ripening

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 27, 2013, Pages 6671-6678

  Peragón, Juan ^a  

^a UNIVERSITY OF JAÉN   (Spain)

Author keywords

erythrodiol; maslinic acid; Olea europaea; oleanolic acid; pentacyclic triterpenoids; ripening; ursolic acid; uvaol

Indexed keywords

ERYTHRODIOL; MASLINIC ACIDS; OLEA EUROPAEA; OLEANOLIC ACIDS; PENTACYCLIC TRITERPENOIDS; RIPENING; URSOLIC ACID; UVAOL;

FORESTRY; PLANTS (BOTANY);

FRUITS;

PENTACYCLIC TRITERPENE; PLANT EXTRACT;

ARTICLE; CHEMISTRY; FRUIT; GROWTH, DEVELOPMENT AND AGING; METABOLISM; OLIVE TREE; PLANT LEAF; TIME;

FRUIT; OLEA; PENTACYCLIC TRITERPENES; PLANT EXTRACTS; PLANT LEAVES; TIME FACTORS;

FORESTRY; FRUITS; PLANTS; RIPENING;

EID: 84880021398     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401495t     Document Type: Article

References (32)

1. Stiti, N.; Triki, S.; Hartmann, M.-A. Formation of triterpenoids throughout Olea europaea fruit ontogeny Lipids 2007, 42, 55-67
2. Wang, D.; Xia, M.; Cui, Z. New triterpenoids isolated from the root bark of Ulmus pumila L Chem. Pharm. Bull. 2006, 54, 775-778
3. Sultana, N.; Lee, N. H. Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa Phytother. Res. 2007, 21, 1171-1176
4. Montilla, M. P.; Agil, A.; Navarro, M. C.; Jiménez, M. I.; García-Granados, A.; Parra, A.; Cabo, M. M. Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea Planta Med. 2003, 69, 472-474
5. Yang, Z. G.; Li, H. R.; Wang, L. Y.; Li, Y. H.; Lu, S. G.; Wen, X. F.; Wang, J.; Daikonya, A.; Kitanaka, S. Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities Chem. Pharm. Bull. 2007, 55, 15-18
6. Márquez-Martín, A.; de la Puerta-Vázquez, R.; Fernández-Arche, A.; Ruíz-Gutiérrez, V. Suppressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages Free Radical Res. 2006, 40, 295-302
7. García-Granados, A.; Martínez, A.; Parra, A.; Rivas, F.; Osuna, A.; Mascaró, C. Use of Maslinic Acid as Inhibitor of Serine Proteases for Treatment of Diseases Caused by Cryptosporidium parasites, Spanish Patent P9701029, 1999.
8. Xu, H. X.; Zeng, F. Q.; Wan, M.; Sim, K. Y. Anti-HIV triterpene acids from Geum japonicum J. Nat. Prod. 1996, 59, 643-645
9. Rivas, F.; Osuna, A.; Mascaró, C.; Nájera, R. Use of Maslinic Acid as Protease Inhibitor in the Treatment of Diseases Caused by the HIV Virus. Spanish patent P2140329; Chem. Abstr. 2000, 135, 483.
10. Reyes-Zurita, F. J.; Centelles, J. J.; Lupiáñez, J. A.; Cascante, M. 2α,3β)-2,3-Dihydroxyolean-12-en-28-oic acid, a new natural triterpene from Olea europea, induce caspase dependent apoptosis selectively in colon adenocarcinoma cells FEBS Lett. 2006, 580, 6302-6310
11. Reyes-Zurita, F. J.; Rufino-Palomares, E. E.; Lupiáñez, J. A.; Cascante, M. Maslinic acid, a natural triterpene from Olea europaea L., induces apoptosis in HT29 human colon-cancer cells via the mitochondrial apoptotic pathway Cancer Lett. 2009, 273, 44-54
12. Kim, K. H.; Seo, H. S.; Choi, H. S.; Choi, I.; Shin, Y. C.; Ko, S. G. Induction of apoptotic cell death by ursolic acid through mitochondrial death pathway and extrinsic death receptor pathway in MDA-MB-231 Cells Arch. Pharm. Res. 2011, 34, 1363-1372
13. Zhou, R.; Zhang, Z.; Zhao, L.; Jia, C.; Xu, S.; Mai, Q.; Lu, M.; Huang, M.; Wang, L.; Wang, X.; Jin, D.; Bai, X. Inhibition of mTOR signaling by oleanolic acid contributes to its anti-tumor activity in osteosarcoma cells J. Orthop. Res. 2011, 29, 846-852
14. Allouche, Y.; Warleta, F.; Campos, M.; Sánchez-Quesada, C.; Uceda, M.; Beltrán, G.; Gaforio, J. J. Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage J. Agric. Food Chem. 2011, 59, 121-130
15. Liby, K. T.; Yore, M. M.; Sporn, M. B. Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer Nat. Rev. Cancer 2007, 7, 357-369
16. Vázquez, A.; Janer, M. L. ácidos triterpénicos del olivo Grasas Aceites (Sevilla, Spain) 1969, 20, 133-137
17. Bianchi, G.; Pozzi, N.; Vlahov, G. Pentacyclic triterpenes acids in olives Phytochemistry 1994, 32, 49-52
18. Guinda, A.; Rada, M.; Delgado, T.; Gutiérrez-Adánez, P.; Castellano, J. M. Pentacyclic triterpenoids from olive fruit and leaf J. Agric. Food. Chem. 2010, 58, 9685-9691
19. Albi, T.; Guinda, A.; Lanzón, A. Procedimiento de obtención y determinación de ácidos triterpénicos de la hoja de olivo Grasas Aceites (Sevilla, Spain) 2001, 52, 275-278
20. Ortega-García, F.; Peragón, J. Phenylalanine ammonia-lyase, polyphenol oxidase and phenols concentration in fruits of Olea europaea L. cv. Picual, Verdial, Arbequina, and Frantoio during ripening J. Agric. Food Chem. 2009, 57, 10331-10340
21. Ortega-García, F.; Peragón, J. HPLC analysis of oleuropein, hydroxytyrosol, and tyrosol in stems and roots of Olea europaea L. cv. Picual during ripening J. Sci. Food Agric. 2010, 90, 2295-2300
22. Ortega-García, F.; Peragón, J. Phenol metabolism in the leaves of the olive tree (Olea europaea L.) cv. Picual, Verdial, Arbequina, and Frantoio during ripening J. Agric. Food Chem. 2010, 58, 12440-12448
23. Uceda, M.; Frías, L. Harvest Dates: Evolution of the Fruit Oil Content, Oil Composition and Oil Quality. In Proceedings of the II Seminario Oleícola Internacional; Consejo Oleícola Internacional: Córdoba, Spain, 1975; pp 125-130.
24. 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
25. 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
26. Van der Heijden, R.; Threlfall, D. R.; Verpoorte, R.; Whitehead, I. M. Regulation and enzymology of pentacyclic triterpenoid phytoalexin biosynthesis in cell suspension cultures of Tabernaemontana divaricate Phytochemistry 1989, 28, 2981-2988
27. Papadopoulou, K.; Melton, R. E.; Leggett, M.; Daniels, M. J.; Osbourn, A. E. Compromised disease resistance in saponin-deficient plants Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12923-12928
28. Bauer, S.; Schulte, E.; Thier, H. P. Composition of the surface wax from tomatoes Eur. Food Res. Technol. 2004, 219, 223-228
29. Mintz-Oron, S.; Mandel, T.; Rogachev, I.; Feldberg, L.; Lotan, O.; Yativ, M.; Wang, Z.; Jetter, R.; Venger, I.; Adato, A.; Aharoni, A. Gene expression and metabolism in tomato fruit surface tissues Plant Physiol. 2008, 147, 823-851
30. Shan, H.; Wilson, W. K.; Phillips, D. R.; Bartel, B.; Matsuda, S. P. Trinorlupeol: a major nonsterol triterpenoid in Arabidopsis Org. Lett. 2008, 10, 1897-1900
31. Rodríguez-Rodríguez, R.; Ruiz-Gutiérrez, V. Functional Properties of Pentacyclic Triterpenes Contained in Pomace Olive Oil. In Olives and Olive Oil in Health and Disease Prevention; Preedy, V. R.; Watson, R. R., Eds.; Academic Press/Elsevier Inc.: London, 2010; pp 1431-1438.
32. Stiti, N.; Hartman, M.-A. Nonsterol triterpenoids as major constituents of Olea europaea J. Lipids. 2012, 10.1155/2012/476595