Chemical composition and antioxidant activity of Algerian propolis

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 21, 2013, Pages 5080-5088

  Piccinelli, Anna Lisa ^a   Mencherini, Teresa ^a   Celano, Rita ^a   Mouhoubi, Zina ^b   Tamendjari, Azeddine ^b   Aquino, Rita Patrizia ^a   Rastrelli, Luca ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF BEJAIA   (Algeria)

Author keywords

Algerian propolis; diterpenes; HPLC ESI MS; HPLC PDA; NMR spectroscopy; phenolic compounds

Indexed keywords

ALGERIAN PROPOLIS; DITERPENES; HPLC-ESI MS; HPLC-PDA; PHENOLIC COMPOUNDS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPIC ANALYSIS;

CHROMATOGRAPHY;

ANTIOXIDANT; FLAVONOID; PLANT EXTRACT; PROPOLIS;

ALGERIA; ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY;

ALGERIA; ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; PLANT EXTRACTS; PROPOLIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84878399131     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf400779w     Document Type: Article

References (44)

1. Salatino, A.; Fernandes-Silva, C. C.; Righi, A. A.; Salatino, M. L. F. Propolis research and the chemistry of plant products Nat. Prod. Rep. 2011, 28, 925-936
2. Banskota, A. H.; Tezuka, Y.; Kadota, S. Recent progress in pharmacological research of propolis Phytother. Res. 2001, 15, 561-571
3. Tosi, E. A.; Ré, E.; Ortega, M. E.; Cazzoli, A. F. Food preservative based on propolis: bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli Food Chem. 2007, 104, 1025-1029
4. Bankova, V. S.; De Castro, S. L.; Marcucci, M. C. Propolis: recent advances in chemistry and plant origin Apidologie 2000, 31, 3-15
5. Cuesta-Rubio, O.; Piccinelli, A. L.; Rastrelli, L. Tropical propolis: advances in chemical components and botanical origin. In Medicinal Plants: Biodiversity and Drugs; Rai, M. K.; Cordell, G. A.; Martinez, J. L.; Marinoff, M.; Rastrelli, L., Eds.; Taylor & Francis: New York, 2012; pp 209-240.
6. Gómez-Caravaca, A. M.; Gómez-Romero, M.; Arráez-Román, D.; Segura-Carretero, A.; Fernández- Gutiérrez, A. Advances in the analysis of phenolic compounds in products derived from bees J. Pharm. Biomed. Anal. 2006, 41, 1220-1234
7. Marquez, H. I.; Cuesta-Rubio, O.; Campo, F. M.; Rosado, P. A.; Montes De Oca, P. R.; Piccinelli, A. L; Rastrelli, L. Studies on the constituents of yellow Cuban propolis: GC-MS determination of triterpenoids and flavonoids J. Agric. Food Chem. 2010, 58, 4725-4730
8. Marcucci, M. C. Propolis: Chemical composition, biological properties and therapeutic activity Apidologie 1995, 26, 83-99
9. Valcic, S.; Montenegro, G.; Timmermann, B. N. Lignans from Chilean propolis J. Nat. Prod. 1998, 61, 771-775
10. Piccinelli, A. L.; Campo, F. M.; Cuesta-Rubio, O.; Marquez, H. I.; De Simone, F.; Rastrelli, L. Isoflavonoids isolated from Cuban propolis J. Agric. Food Chem. 2005, 53, 9010-9016
11. Awale, S.; Li, F.; Onozuka, H.; Esumi, H.; Tezuka, Y.; Kadota, S. Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition Bioorg. Med. Chem. 2008, 16, 181-189
12. Cuesta-Rubio, O.; Piccinelli, A. L.; Campo, F. C.; Marquez, H. I.; Rosado, A.; Rastrelli, L. Chemical characterization of Cuban propolis by HPLC-PDA, HPLC-MS, and NMR: the brown, red, and yellow Cuban varieties of propolis J. Agric. Food Chem. 2007, 55, 7502-7509
13. Bankova, V. Chemical diversity of propolis and the problem of standardization J. Ethnopharmacol. 2005, 100, 114-117
14. Lahouel, M.; Boutabet, K.; Kebsa, W.; Alyane, M. Polyphenolic fractions of Algerian propolis reverses doxorubicin induced acute renal oxidative stress Afr. J. Pharm. Pharmacol. 2010, 4, 712-720
15. Alyane, M.; Benguedouar, L.; Kebsa, W.; Boussenane, H. N.; Rouibah, H.; Lahouel, M. Cardioprotective effects and mechanism of action of polyphenols extracted from propolis against doxorubicin toxicity Pak. J. Pharm. Sci. 2008, 21, 201-209
16. Segueni, N.; Magid, A. A.; Decarme, M.; Rhouati, S.; Lahouel, M.; Antonicelli, F.; Lavaud, C.; Hornebeck, W. Inhibition of stromelysin-1 by caffeic acid derivatives from a propolis sample from Algeria Planta Med. 2011, 77, 999-1004
17. Segueni, N.; Zellagui, A.; Moussaoui, F.; Lahouel, M.; Rhouati, S. Flavonoids from Algerian propolis Arab. J. Chem. 2013, 10.1016/j.arabjc.2011.05. 013
18. Velikova, M.; Bankova, V.; Sorkun, K.; Houcine, S.; Tsvetkova, I.; Kujumgiev, A. Propolis from the Mediterranean region: chemical composition and antimicrobial activity Z. Naturforsch. C 2000, 55, 790-793
19. Piccinelli, A. L.; Lotti, C.; Campone, L.; Cuesta-Rubio, O.; Campo, F. M.; Rastrelli, L. Cuban and Brazilian red propolis: botanical origin and comparative analysis by high-performance liquid chromatography photodiode array detection/electrospray ionization tandem mass spectrometry J. Agric. Food Chem. 2011, 59, 6484-6491
20. Bankova, V. S. Synthesis of natural esters of substituted cinnamic acids J. Nat. Prod. 1990, 53, 821-824
21. Greenaway, W.; Whatley, F. R. Synthesis of esters of acetyloxycaffeic acids and their occurrence in poplar bud exudates J. Chromatogr. A 1991, 543, 113-121
22. Grunberger, D.; Banerjee, R.; Eisinger, K.; Oltz, E. M.; Efros, L.; Caldwell, M.; Estevez, V.; Nakanishi, K. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis Experientia 1988, 44, 230-232
23. 1H-NMR simultaneous identification of health-relevant compounds in propolis extracts Phytochem. Anal. 2012, 23, 260-266
24. Kuroyanagi, M.; Yamamoto, Y.; Fukushima, S.; Ueno, A.; Noro, T.; Miyase, T. Chemical studies on the constituents of Polygonum nodosum Chem. Pharm. Bull. 1982, 30, 1602-1608
25. Tran, V. H.; Duke, R. K.; Abu-Mellal, A.; Duke, C. C. Propolis with high flavonoid content collected by honey bees from Acacia paradoxa Phytochemistry 2012, 81, 126-132
26. Shi, C.; Xu, M. J.; Bayer, M.; Deng, Z. W.; Kubbutat, M. H.; Wätjen, W.; Proksch, P.; Lin, W. H. Phenolic compounds and their anti-oxidative properties and protein kinase inhibition from the Chinese mangrove plant Laguncularia racemosa Phytochemistry 2010, 71, 435-442
27. Mangoni, L.; Belardini, M. Components of Cupressus sempervirens resin. I. Communic acid, cupressic acid, and isocupressic acid Gazz. Chim. Ital. 1964, 94, 1108-1121
28. Woo, K. W.; Choi, S. U.; Park, J. C.; Lee, K. R. A new lignan glycoside from Juniperus rigida Arch. Pharm. Res. 2011, 34, 2043-2049
29. Hanari, N.; Yamamoto, H.; Kuroda, K. Comparison of terpenes in extracts from the resin and the bark of the resinous stem canker of Chamaecyparis obtusa and Thujopsis dolabrata var. hondae J. Wood Sci. 2002, 48, 56-63
30. Khamidullina, E. A.; Vereshchagin, A. L.; Medvedeva, S. A. Structure of a new diterpene alcohol from Pinus sibirica buds Chem. Nat. Compd. 2005, 41, 426-428
31. Chiang, Y. M.; Liu, H. K.; Lo, J. M.; Chien, S. C.; Chan, Y. F.; Lee, T. H.; Su, J. K.; Kuo, Y. H. Cytotoxic constituents of the leaves of Calocedrus formosana J. Chin. Chem. Soc. 2003, 50, 161-166
32. Kalpoutzakis, E.; Aligiannis, N.; Skaltsounis, A. L.; Mitakou, S. cis-Clerodane type diterpenes from Cistus monspeliensis J. Nat. Prod. 2003, 66, 316-319
33. Martos, I.; Cossentini, M.; Ferreres, F.; Tomás-Barberán, F. A. Flavonoid composition of Tunisian honeys and propolis J. Agric. Food Chem. 1997, 45, 2824-2829
34. Mencherini, T.; Picerno, P.; Scesa, C.; Aquino, R. P. Triterpene antioxidant and antimicrobial compounds from Melissa officinalis J. Nat. Prod. 2007, 70, 1889-1894
35. Gardana, C.; Scaglianti, M.; Pietta, P. G.; Simonetti, P. Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography-tandem mass spectrometry J. Pharm. Biom. Anal. 2007, 45, 390-399
36. Falcão, S. I.; Vilas-Boas, M.; Estevinho, L. M.; Barros, C.; Domingues, M. R.; Cardoso, S. M. Phenolic characterization of Northeast Portuguese propolis: usual and unusual compounds Anal. Bioanal. Chem. 2010, 396, 887-897
37. Pratsinis, H.; Kletsas, D.; Melliou, E.; Chinou, I. Antiproliferative activity of Greek propolis J. Med. Food 2010, 13, 286-290
38. Banskota, A. H.; Tezuka, Y.; Prasain, J. K.; Matsushige, K.; Saiki, I.; Kadota, S. Chemical constituents of Brazilian propolis and their cytotoxic activity J. Nat. Prod. 1998, 61, 896-900
39. Bankova, V.; Marcucci, M. C.; Simova, S.; Nikolova, N.; Kujumigiev, A. Antibacterial diterpenic acids from Brazilian propolis Z. Naturforsch. C 1996, 51, 227-280
40. Sulamain, G. M.; Al Sammarrae, K. W.; A'dhiah, A. H.; Zucchetti, M.; Frapolli, R.; Bello, E.; Erba, E.; D'Incalci, M.; Bagnati, R. Chemical characterization of Iraqi propolis samples and assessing their antioxidant potentials Food Chem. Toxicol. 2011, 49, 2415-2421
41. Mitamura, T.; Matsuno, T.; Sakamoto, S.; Maemura, M.; Kudo, H.; Suzuki, S.; Kuwa, K.; Yoshimura, S.; Sassa, S. Effects of a new clerodane diterpenoid isolated front propolis on chemically induced skin tumors in mice Anticancer Res. 1996, 16, 2669-2672
42. Kumazawa, S.; Hamasaka, T.; Nakayama, T. Antioxidant activity of propolis of various geographic origins Food Chem. 2004, 84, 329-339
43. Gregoris, E.; Stevanato, R. Correlations between polyphenolic composition and antioxidant activity of Venetian propolis Food Chem. Toxicol. 2010, 48, 76-82
44. Yang, H.; Dong, Y.; Du, H.; Shi, H.; Peng, Y.; Li, X. Antioxidant compounds from propolis collected in Anhui, China Molecules 2011, 16, 3444-3455