Isolation and characterization of phenolic compounds and anthocyanins from murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity

Molecules

Volumn 20, Issue 4, 2015, Pages 5698-5713

  Junqueira Gonçalves, Maria Paula ^a   Yáñez, Lina ^a   Morales, Carolina ^a   Navarro, Muriel ^a   Contreras, Rodrigo A ^a   Zúñiga, Gustavo E ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

Anthocyanins; Antibacterial activity; Antioxidant activity; HPLC ESI MS; Phenolics; Ugni molinae Turcz

Indexed keywords

ANTHOCYANIN; ANTIOXIDANT; DELPHINIDIN 3-O-GLUCOPYRANOSIDE; GLUCOSIDE; PELARGONIDIN; PHENOL DERIVATIVE; PLANT EXTRACT;

CHEMISTRY; DRUG EFFECTS; ESCHERICHIA COLI; FRUIT; HUMAN; ISOLATION AND PURIFICATION; MYRTACEAE;

ANTHOCYANINS; ANTIOXIDANTS; ESCHERICHIA COLI; FRUIT; GLUCOSIDES; HUMANS; MYRTACEAE; PHENOLS; PLANT EXTRACTS;

EID: 84928812015     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20045698     Document Type: Article

References (55)

1. Paredes-López, O.; Cervantes-Ceja, M.; Vigna-Pérez, M.; Hernández-Pérez, T. Berries: Improving human health and healthy aging, and promoting quality life - A review. Plant Foods Hum. Nutr. 2010, 65, 299-308.
2. Arancibia-Avila, P.; Toledo, F.; Werner, E.; Suhaj, M.; Leontowicz, H.; Leontowicz, M.; Martinez-Ayala, A.L.; Paśko, P.; Gorinstein, S. Partial characterization of a new kind of Chilean murtilla-like berries. Food Res. Int. 2011, 44, 2054-2062.
3. Ruiz, A.; Hermosín-Gutiérrez, I.; Mardones, C.; Vergara, C.; Herlitz, E.; Vega, M.; Dorau, C.; Winterhalter, P.; von Baer, D. Polyphenols and antioxidant activity of calafate (Berberis microphylla) fruits and other native berries from Southern Chile. J. Agric. Food Chem. 2010, 58, 6081-6089.
4. Johnson, M.; Wesely, E.G.; Zahir, H.M.I.; Selvan, N. In vivo and in vitro phytochemical and antibacterial efficacy of Baliospermum montanum (Wïlld.) Muell. Arg. Asian Pac. J. Trop. Med. 2010, 3, 894-897.
5. Zia-Ul-Haq, M.; Ahmad, M.; Mehjabeen; Jehan, N.; Ahmad, S.; Qayum, M.; Marwat, K.I. Antimicrobial screening of selected flora of Pakistan. Arch. Biol. Sci. 2011, 63, 691-695.
6. Machiex, J. -J.; Fleuriet, A.; Billot, J. Importance and roles of phenolic compounds in fruits. In Fruit Phenolics; CRC Press: Boca Raton, FL, USA, 1990.
7. Cao, G.; Sofic, E.; Prior, R. Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radic. Biol. Med. 1997, 22, 749-760.
8. Serrano, M.; Díaz-Mula, H.M.; Valero, D. Antioxidant compounds in fruits and vegetables and changes during postharvest storage and processing. Stewart Posthar. Rev. 2011, 7, 1-10.
9. Pazmiño-Durán, E.A.; Giusti, M.M.; Wrolstad, R.E.; Gloria, M.B.A. Anthocyanins from Oxalis triangularis as potential food colorants. Food Chem. 2001, 75, 211-216.
10. Longo, L.; Vasapollo, G. Extraction and Identification of anthocyanins from Smilax aspera L. berries. Food Chem. 2006, 94, 226-231.
11. Tsai, P.J.; McIntosh, J.; Pearce, P.; Camden, B.; Jordan, B.R. Anthocyanins and antioxidants capacity in Roselle (Hibiscus sabdariffa L.) extract. Food Res. Int. 2002, 35, 351-356.
12. Prior, X.L.; Wu, X. Anthocyanins: Structural characteristics that result in unique metabolic patterns and biological activities. Free Radic. Res. 2006, 40, 1014-1028.
13. Wu, X.; Beecher, G.; Holden, J.; Haytowitz, D.; Gebhardt, S.E.; Prior, R.L. Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. J. Agric. Food Chem. 2004, 52, 4026-4037.
14. Muñoz, M.; Muñoz, C.; Godoy, I. Especie nativa con potencial como frutales arbustivos. Investig. Prog. Agropecu. Carillanca 1996, 5, 32-35.
15. Montenegro, G. Nuestra Flora Útil; Ediciones Universidad Católica de Chile: Santiago, Chile, 2000.
16. Pastenes, C.; Santa-María, E.; Infante, R.; Franck, N. Domestication of the Chilean guava (Ugni molinae Turcz.), a forest under storey shrub, must consider light intensity. Sci. Hortic. 2003, 98, 71-84.
17. Scheuermann, E.; Seguel, I.; Montenegro, A.; Bustos, R.O.; Hormazabal, E.; Quiroz, A. Evolution of aroma compounds of murtilla fruits (Ugni molinae Turcz) during storage. J. Sci. Food Agric. 2008, 88, 485-492.
18. Taboada, E.; Fisher, P.; Jara, R.; Zuñiga, E.; Gidekel, M.; Cabrera, J.C.; Pereira, E.; Gutiérrez-Moraga, A.; Villalonga, R.; Cabrera, G. Isolation and characterisation of pectic substances from murta (Ugni molinae Turcz) fruits. Food Chem. 2010, 123, 669-678.
19. Avello, M.; Pastene, E. Actividad antioxidante de infusos de Ugni molinae Turcz. ("Murtilla"). Blacpma 2005, 4, 33-39.
20. Rubilar, M.; Pinelo, M.; Ihl, M.; Scheuermann, E.; Sineiro, J.; Nuñez, M.J. Murta leaves (Ugni molinae Turcz) as a source of antioxidant phenols. J. Agric. Food Chem. 2006, 54, 59-64.
21. Shene, C.; Reyes, A.; Villarroel, M.; Sineiro, J.; Pinelo, M.; Rubilar, M. Plant location and extraction procedure strongly alter the antimicrobial activity of murta extracts. Eur. Food Res. Technol. 2009, 228, 467-475.
22. Rubilar, M.; Jara, C.; Poo, P.; Acevedo, F.; Gutierrez, C.; Sineiro, J.; Shene, C. Extracts of Maqui (Aristotelia chilensis) and Murta (Ugni molinae Turcz.): Sources of Antioxidant Compounds and α-Glucosidase/α-Amylase Inhibitors. J. Agric. Food Chem. 2011, 59, 1630-1637.
23. Sasaki, H.; Nishimura, H.; Morota, T.; Chin, M.; Mitsuhashi, H.; Komatso, Y.; Maruyama, H.; Tu, G.R.; Wei, H.; Xiong, Y.L. Immunosuppressive principle of Rehmannia glutinosa var. hueichingensis. Planta Med. 1989, 55, 458-462.
24. Scalbert, A.; Williamson, G. Dietary intake and bioavailability of polyphenols. J. Nutr. 2000, 130, 2073-2085.
25. Formica, J.V.; Regelson, W. Review of the biology of quercetin and related bioflavonoids. Food Chem. Toxicol. 1995, 33, 1061-1080.
26. Middleton, E., Jr.; Kandaswami, C.; Theoharides, T.C. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52, 673-751.
27. Harborne, J.B.; Williams, C.A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55, 481-504.
28. Walsky, R.L.; Gaman, E.A.; Obach, R.S. Examination of 209 drugs for inhibition of cytochrome P450 2C8. J. Clin. Pharmacol. 2005, 45, 68-78.
29. Otake, Y.; Nolan, A.L.; Walle, U.K.; Walle, T. Quercetin and resveratrol potently reduce estrogen sulfotransferase activity in normal human mammary epithelial cells. J. Steroid Biochem. Mol. Biol. 2000, 63, 265-270.
30. Huang, S.L.; Hsu, C.L.; Yen, G.C. Growth inhibitory effect of quercetin on SW 872 human liposarcoma cells. Life Sci. 2006, 79, 203-209.
31. Hollman, P.C.; van Trijp, J.M.; Buysman, M.N.; van der Gaag, M.S.; Mengelers, M.J.; de Vries, J.H.; Katan, M.B. Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 1997, 418, 152-156.
32. Leighton, T.; Ginther, C.; Fluss, L.; Harter, W.K.; Cansado, J.; Notario, V. Molecular Characterization of Quercetin and Quercetin Glycosides in Allium Vegetables. In Phenolic Compounds in Food and Their Effects on Health II; American Chemical Society: Washington, DC, USA, 1992; pp. 220-238.
33. Yang, R.-Y.; Lin, S.; Kuo, G. Content and distribution of flavonoids among 91 edible plant species. Asia Pac. J. Clin. Nutr. 2008, 17, 275-279.
34. Goet, R.K.; Pandey, V.B.; Dwivedi, S.P.D.; Rao, Y.V. Antiinflammatory and antiulcer effects of kaempferol, a flavone, isolated from Rhamnus procumbens. Indian J. Exp. Biol. 1988, 26, 121-124.
35. Wilhelm, K.P.; Biel, S.; Siegers, C.P. Role of flavonoids in controlling the phototoxicity of Hypericum perforatum extract. Phytomedicine 2001, 8, 306-309.
36. Arima, H.; Ashida, H.; Danno, G. Rutin-enhanced antibacterial activities of flavonoids against Bacillus cereus and Salmonella enteritidis. Biosci. Biotechnol. Biochem. 2002, 66, 1009-1014.
37. De Medina, F.S.; Vera, B.; Galvez, J.; Zarzuelo, A. Effect of quercitrin on the early stages of hapten induced colonic inflammation in the rat. Life Sci. 2001, 70, 3097-3108.
38. Pati, S.; Losito, I.; Gambacorta, G.; La Notte, E.; Palmisano, F.; Zambonin, P.G. Simultaneous separation and identification of oligomeric procyanidins and anthocyanin-derived pigments in raw red wine by HPLC-UV-ESI-MSn. J. Mass Spectrom. 2006, 41, 861-871.
39. De Pascual-Teresa, S.; Sanchez-Ballesta, M.T. Anthocyanins: From plant to health. Phytochem. Rev. 2008, 7, 281-299.
40. Aguirre, M.C.; Delporte, C.; Backhouse, N.; Erazo, S.; Letelier, M.E.; Cassels, B.K.; Silva, X.; Alegría, S.; Negrete, R. Topical anti-inflammatory activity of 2a-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae. Bioorganic Med. Chem. 2006, 14, 5673-5677.
41. Delporte, C.; Backhouse, N.; Inostroza, V.; Aguirre, M.C.; Peredo, N.; Silva, X. Analgesic activity of Ugni molinae (murtilla) in mice models of acute pain. J. Ethnopharmacol. 2007, 112, 162-165.
42. Capecka, E.; Mareczek, A.; Leja, M. Antioxidant activity of fresh and dry herbs of some Lamiaceae species. Food Chem. 2005, 93, 223-226.
43. Lopez, M.; Martinez, F.; Del Valle, C.; Ferrit, M.; Luque, R. Study of phenolic compounds as natural antioxidants by a fluorescence method. Talanta 2005, 6, 609-616.
44. Aberoumand, A.; Deokule, S.S. Comparison of Phenolic Compounds of Some Edible Plants of Iran and India. Pak. J. Nutr. 2008, 7, 582-585.
45. Nascimento, P.L.A.; Nascimento, T.C.E.S.; Ramos, N.S.M.; Silva, G.R.; Galindo Gomes, J.E.; Falcão, R.E.A.; Moreira, K.A.; Porto, A.L.F.; Silva, T.M.S. Quantification, antioxidant and antimicrobial activity of phenolics isolated from different extracts of Capsicum frutescens (Pimenta Malagueta). Molecules 2014, 19, 5434-5447.
46. Wang, S.Y.; Chen, C.-T.; Sciarappa, W.; Wang, C.Y.; Camp, M.J. Fruit Quality, Antioxidant Capacity, and Flavonoid Content of Organically and Conventionally Grown Blueberries. J. Agric. Food Chem. 2008, 56, 5788-5794.
47. Turgis, M.; Borsa, J.; Millette, M.; Salmieri, S.; Lacroix, M. Effect of selected plant essential oils or their constituents and modified atmosphere packaging on the radio sensitivity of Escherichia coli O157:H7 and Salmonella Typhi in ground beef. J. Food Prot. 2008, 71, 516-521.
48. Avello, M.; Valdivia, R.; Sanzana, R.; Mondaca, M.A.; Mennickent, S.; Aeschlimann, M.; Bittner, M.; Becerra, J. Extractos antioxidantes y antimicrobianos de Aristotelia chilensis y Ugni molinae y sus aplicaciones como preservantes en productos cosméticos. Bol. Latinoam. Caribe Plantas Med. Aromát. 2009, 8, 479-486.
49. Mølgaard, P.; Hollera, J.G.; Asarb, B.; Libernaa, I.; Rosenbæka, L.B.; Jebjerga, C.P.; Jørgensen, L.; Lauritzen, J.; Guzman, A.; Adsersen, A.; et al. Antimicrobial evaluation of Huilliche plant medicine used to treat wounds. J. Ethnopharmacol. 2011, 138, 219-227.
50. Venkata, S.P.; Murali, M.C.; Prameela, K.; Sravani, R.; Raju, B.A. Screening of Antimicrobial and Antioxidant Potentials of Acacia caesia, Dillenia pentagyna and Buchanania lanzan from Maredumilli Forest of India. J. Pharm. Res. 2012, 5, 1734-1738.
51. Fuleki, T.; Francis, F.J. Quantitative methods for anthocyanins. IN. Extraction and determination of total anthocyanin in Cranberries. J. Food Sci. 1968, 33, 72-77.
52. Bravo, L.; Goya, L.; Lucumberri, E. LC/MS characterization of phenolic constituents of mate (Ilex paraguariensis, St. Hil.) and its antioxidant activity compared to commonly consumed beverages. Food Res. Int. 2007, 40, 393-405.
53. Qin, C.G.; Li, Y.; Zhang, R.J.; Niu, W.N.; Ding, Y. Separation and elucidation of anthocyanins in fruit of mockstrawberry (Duchesnea indica Focke). Nat. Product Res. 2009, 23, 1589-1598.
54. Shyu, Y.- S.; Lin, J.-T.; Chang, Y.- T.; Chiang, C.- J.; Yang, D.-J. Evaluation of antioxidant ability of ethanolic extract from dill (Anethum graveolens L.) flower. Food Chem. 2009, 115, 515-521.
55. Alarcón, E.; Campos, A.M.; Edwards, A.M.; Lissi, E.; López-Alarcón, C. Antioxidant capacity of herbal infusions and tea extracts: A comparison of ORAC-fluorescein and ORAC-pyrogallol red methodologies. Food Chem. 2008, 107, 1114-1122.