Comparative chemistry of propolis from eight brazilian localities

Evidence-based Complementary and Alternative Medicine

Volumn 2013, Issue , 2013, Pages

  Righi, A A ^a   Negri, G ^b   Salatino, A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYLCHROMENE DERIVATIVE; ALCOHOL; ALPHA AMYRIN; BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; CHLOROFORM; ERGOSTEROL; FERULIC ACID; FLAVANONE DERIVATIVE; HEXADECANE; METHANOL; OLEIC ACID; PALMITIC ACID; PARA COUMARIC ACID; PROPOLIS; TARAXERONE;

ARTICLE; BRAZIL; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG DETERMINATION; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL;

EID: 84877289689     PISSN: 1741427X     EISSN: 17414288     Source Type: Journal    
DOI: 10.1155/2013/267878     Document Type: Article

References (60)

1. Lustosa S. R., Galindo A. B., Nunes L. C. C., Randau K. P., Neto P. J. R., Propolis: updates on chemistry and pharmacology. Brazilian Journal of Pharmacognosy 2008 18 3 447 454 2-s2.0-55849121963 10.1590/S0102- 695X2008000300020
2. Bankova V., Recent trends and important developments in propolis research. Evidence-Based Complementary and Alternative Medicine 2005 2 1 29 32 2-s2.0-23044479136 10.1093/ecam/neh059 (Pubitemid 41399511)
3. Yang S. Z., Peng L. T., Su X. J., Chen F., Cheng Y. J., Fan G., Pan S. Y., Bioassay-guided isolation and identification of antifungal components from propolis against Penicillium italicum. Food Chemistry 2011 127 1 210 215 2-s2.0-79951509444 10.1016/j.foodchem.2010.12.011
4. Vardar-Unlu G., Silici S., Unlu M., Composition and in vitro antimicrobial activity of Populus buds and poplar-type propolis. World Journal of Microbiology and Biotechnology 2008 24 7 1011 1017 2-s2.0-44649102648 10.1007/s11274-007-9566-5 (Pubitemid 351782202)
5. Bastos E. M. A. F., Simone M., Jorge D. M., Soares A. E. E., Spivak M., In vitro study of the antimicrobial activity of Brazilian propolis against Paenibacillus larvae. Journal of Invertebrate Pathology 2008 97 3 273 281 2-s2.0-39449108393 10.1016/j.jip.2007.10.007 (Pubitemid 351273724)
6. Paulino N., Abreu S. R. L., Uto Y., Koyama D., Nagasawa H., Hori H., Dirsch V. M., Vollmar A. M., Scremin A., Bretz W. A., Anti-inflammatory effects of a bioavailable compound, Artepillin C, in Brazilian propolis. European Journal of Pharmacology 2008 587 1-3 296 301 2-s2.0-44149099992 10.1016/j.ejphar.2008.02.067
7. Jung W. K., Lee D. Y., Choi Y. H., Yea S. S., Choi I., Park S. G., Seo S. K., Lee S. W., Lee C. M., Kim S. K., Jeon Y. J., Choi I. W., Caffeic acid phenethyl ester attenuates allergic airway inflammation and hyperresponsiveness in murine model of ovalbumin-induced asthma. Life Sciences 2008 82 13-14 797 805 2-s2.0-40649123732 10.1016/j.lfs.2008.01.014
8. Xi J., Shouqin Z., Antioxidant activity of ethanolic extracts of propolis by high hydrostatic pressure extraction. International Journal of Food Science and Technology 2007 42 11 1350 1356 2-s2.0-35448968912 10.1111/j.1365-2621.2006. 01339.x (Pubitemid 47628699)
9. Wu W. M., Lu L., Long Y., Wang T., Liu L., Chen Q., Wang R., Free radical scavenging and antioxidative activities of caffeic acid phenethyl ester (CAPE) and its related compounds in solution and membranes: a structure-activity insight. Food Chemistry 2007 105 1 107 115 2-s2.0-34347351367 10.1016/j.foodchem.2007.03.049 (Pubitemid 47016817)
10. De Barros M. P., Sousa J. P. B., Bastos J. K., de Andrade S. F., Effect of Brazilian green propolis on experimental gastric ulcers in rats. Journal of Ethnopharmacology 2007 110 3 567 571 2-s2.0-33847703665 10.1016/j.jep.2006.10. 022 (Pubitemid 46386368)
11. Orsolic N., Basic I., Water-soluble derivative of propolis and its polyphenolic compounds enhance tumoricidal activity of macrophages. Journal of Ethnopharmacology 2005 102 1 37 45 2-s2.0-25444450345 10.1016/j.jep.2005.05.036 (Pubitemid 41375936)
12. Salatino A., Fernandes-Silva C. C., Righi A. A., Salatino M. L. F., Propolis research and the chemistry of plant products. Natural Product Reports 2011 28 5 925 936 2-s2.0-79955035707 10.1039/c0np00072h
13. Hrobonova K., Lehotay J., Cizmarik J., Determination of some phenolic acids in propolis by an HPLC method. Journal of Liquid Chromatography and Related Technologies 2008 31 8 1213 1226 2-s2.0-41349105465 10.1080/ 10826070802000822 (Pubitemid 351451785)
14. Gardana C., Scaglianti M., Pietta P., Simonetti P., Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography-tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2007 45 3 390 399 2-s2.0-35348888888 10.1016/j.jpba.2007.06. 022 (Pubitemid 47588764)
15. 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. Bioorganic and Medicinal Chemistry 2008 16 1 181 189 2-s2.0-38049034385 10.1016/j.bmc.2007.10.004
16. Li F., Awale S., Tezuka Y., Kadota S., Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship. Bioorganic and Medicinal Chemistry 2008 16 10 5434 5440 2-s2.0-43749087342 10.1016/j.bmc.2008.04.016 (Pubitemid 351694485)
17. Sahinler N., Kaftanoglu O., Natural product propolis: chemical composition. Natural Product Research 2005 19 2 183 188 2-s2.0-13244291451 10.1080/14786410410001704877 (Pubitemid 40185887)
18. Abu-Mellal A., Koolaji N., Duke R. K., Tran V. H., Duke C. C., Prenylated cinnamate and stilbenes from Kangoroo Island propolis and their antioxidant activity. Phytochemistry 2012 77 251 259
19. Bankova V. S., de Castro S. L., Marcucci M. C., Propolis: recent advances in chemistry and plant origin. Apidologie 2000 31 1 3 15 2-s2.0-0033976532 (Pubitemid 30106313)
20. Popova M. P., Graikou K., Chinou I., Bankova V. S., GC-MS profiling of diterpene compounds in mediterranean propolis from Greece. Journal of Agricultural and Food Chemistry 2010 58 5 3167 3176 2-s2.0-77949401327 10.1021/jf903841k
21. Chen C.-N., Wu C.-L., Shy H.-S., Lin J.-K., Cytotoxic prenylflavanones from Taiwanese propolis. Journal of Natural Products 2003 66 4 503 506 2-s2.0-0037998235 10.1021/np0203180 (Pubitemid 36531897)
22. Kumazawa S., Goto H., Hamasaka T., Fukumoto S., Fujimoto T., Nakayama T., A new prenylated flavonoid from propolis collected in Okinawa, Japan. Bioscience, Biotechnology and Biochemistry 2004 68 1 260 262 2-s2.0-2442529445 10.1271/bbb.68.260 (Pubitemid 39251598)
23. Popova M. P., Chinou I. B., Marekov I. N., Bankova V. S., Terpenes with antimicrobial activity from Cretan propolis. Phytochemistry 2009 70 10 1262 1271 2-s2.0-69249141909 10.1016/j.phytochem.2009.07.025
24. Teixeira E. W., Message D., Negri G., Salatino A., Stringheta P. C., Seasonal variation, chemical composition and antioxidant activity of brazilian propolis samples. Evidence-Based Complementary and Alternative Medicine 2010 7 3 307 315 2-s2.0-77953859590 10.1093/ecam/nem177
25. Trusheva B., Popova M., Bankova V., Simova S., Marcucci M. C., Miorin P. L., Pasin F. D. R., Tsvetkova I., Bioactive constituents of Brazilian red propolis. Evidence-Based Complementary and Alternative Medicine 2006 3 2 249 254 2-s2.0-33745698152 10.1093/ecam/nel006
26. Righi A. A., Alves T. R., Negri G., Marques L. M., Breyer H., Salatino A., Brazilian Red Propolis: unreported substances, antioxidant and antimicrobial activities. Journal of the Science of Food and Agriculture 2011 91 13 2363 2370
27. Ishida V. F. C., Negri G., Salatino A., Bandeira M. F. C. L., A new type of Brazilian propolis: prenylated benzophenones in propolis from Amazon and effects against cariogenic bacteria. Food Chemistry 2011 125 3 966 972 2-s2.0-78149414317 10.1016/j.foodchem.2010.09.089
28. Salatino A., Teixeira E. W., Negri G., Message D., Origin and chemical variation of Brazilian propolis. Evidence-based Complementary and Alternative Medicine 2005 2 1 33 38 2-s2.0-24344444003 10.1093/ecam/neh060 (Pubitemid 41399512)
29. Sorkun K., Suer B., Salih B., Determination of chemical composition of Turkish propolis. Zeitschrift fur Naturforschung C 2001 56 7-8 666 668 2-s2.0-0034887114 (Pubitemid 32745298)
30. Bankova V., Popova M., Bogdanov S., Sabatini A. G., Chemical composition of European propolis: expected and unexpected results. Zeitschrift fur Naturforschung C 2002 57 5-6 530 533 2-s2.0-0036560363 (Pubitemid 34775948)
31. Negri G., Salatino M. L. F., Salatino A., 'Green propolis': unreported constituents and a novel compound from chloroform extracts. Journal of Apicultural Research 2003 42 3 39 41 2-s2.0-0347278526 (Pubitemid 39622676)
32. Negri G., Salatino M. L. F., Salatino A., Unusual chemical composition of a sample of Brazilian propolis, as assessed by analysis of a chloroform extract. Journal of Apicultural Research 2003 42 4 53 56 2-s2.0-0347028437 (Pubitemid 38075013)
33. Marcucci M. C., Rodriguez J., Ferreres F., Bankova V., Groto R., Popov S., Chemical composition of Brazilian propolis from Sao Paulo State. Zeitschrift fur Naturforschung C 1998 53 1-2 117 119 2-s2.0-0031952347 (Pubitemid 28111166)
34. Teixeira E. W., Message D., Negri G., Salatino A., Stringheta P. C., Seasonal variation, chemical composition and antioxidant activity of Brazilian propolis samples. Evidence-Based Complementary and Alternative Medicine 2010 7 3 307 315 2-s2.0-77953859590 10.1093/ecam/nem177
35. Piccinelli A. L., Lotti C., Campone L., Cuesta-Rubio O., Fernandez M. C., 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. Journal of Agricultural and Food Chemistry 2011 59 12 6484 6491 2-s2.0-79959196128 10.1021/jf201280z
36. Negri G., Marcucci M. C., Salatino A., Salatino M. L. F., Comb and propolis waxes from Brazil (States of São Paulo and Paraná). Journal of the Brazilian Chemical Society 2000 11 5 453 457 2-s2.0-0034367791
37. Woisky R. G., Salatino A., Analysis of propolis: some parameters and procedures for chemical quality control. Journal of Apicultural Research 1998 37 2 99 105 2-s2.0-0032348647 (Pubitemid 128371948)
38. Nagy M., Grančai D., Colorimetric determination of flavanones in propolis. Pharmazie 1996 51 2 100 101 2-s2.0-0029932683 (Pubitemid 26078095)
39. MacLafferty S. W., Stauffer D. B., The Wiley/NBS Registry of Mass Espectral Data 1989 New York, NY, USA John Wiley
40. Swofford DL. PAUP: Phylogenetic Analysis Using Parsimony (other methods), version 4.0b10. Sinauer Associates, Sunderland, Mass, USA, 2002
41. Custodio A. R., Ferreira M. M. C., Negri G., Salatino A., Clustering of comb and propolis waxes based on the distribution of aliphatic constituents. Journal of the Brazilian Chemical Society 2003 14 3 354 357 2-s2.0-0038729207 (Pubitemid 36791563)
42. Teixeira E. W., Negri G., Meira R. M. S. A., Message D., Salatino A., Plant origin of green propolis: bee behavior, plant anatomy and chemistry. Evidence-Based Complementary and Alternative Medicine 2005 2 1 85 92 2-s2.0-24344458459 10.1093/ecam/neh055 (Pubitemid 41399518)
43. Bankova V., Marcucci M. C., Simova S., Nikolova N., Kujumgiev A., Popov S., Antibacterial diterpenic acids from Brazilian propolis. Zeitschrift fur Naturforschung C 1996 51 5-6 277 280 2-s2.0-0030152164
44. Li F., Awale S., Tezuka Y., Esumi H., Kadota S., Study on the constituents of mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells. Journal of Natural Products 2010 73 4 623 627 2-s2.0-77951523025 10.1021/np900772m
45. Moura S. A. L., Negri G., Salatino A., Aqueous extract of Brazilian Green Propolis: primary components, evaluation of inflammation and wound healing by using subcutaneous implanted sponges. Evidence-Based Complementary and Alternative Medicine 2011 2011 8 748283 10.1093/ecam/nep112
46. Takemura T., Urushisaki T., Fukuoka M., 3,4-Dicaffeoylquinic acid, a major constituent of Brazilian propolis, increases TRAIL expression and extends the lifetime of mica infected with influenza virus. Evidence-Based Complementary and Alternative Medicine 2012 2012 7 946867 10.1155/2012/946867
47. Truchado P., Vit P., Ferreres F., Tomas-Barberan F., Liquid chromatography tandem mass spectrometry analysis allows the simultaneous characterization of C-glycosyl and O-glycosyl flavonoids in stingless bee honeys. Journal of Chromatography A 2011 1218 7601 7607
48. Truchado P., Ferreres F., Tomas-Barberan F. A., Liquid chromatography-tandem mass spectrometry reveals the widespread occurrence of flavonoid glycosides in honey, and their potential as floral origin markers. Journal of Chromatography A 2009 1216 43 7241 7248 2-s2.0-74049097552 10.1016/j.chroma.2009.07.057
49. Piccinelli A. L., Mesa M. G., Armenteros D. M., Alfonso M. A., Arevalo A. C., Campone L., Rastrelli L., HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. Journal of Agricultural and Food Chemistry 2008 56 5 1574 1581 2-s2.0-41949106350 10.1021/jf073485k (Pubitemid 351506865)
50. Barreca D., Bellocco E., Caristi C., Leuzzi U., Gattuso G., Flavonoid profile and radical-scavenging activity of Mediterranean sweet lemon (Citrus limetta Risso) juice. Food Chemistry 2011 129 2 417 422 2-s2.0-79959966025 10.1016/j.foodchem.2011.04.093
51. Figueirinha A., Paranhos A., Pérez-Alonso J. J., Santos-Buelga C., Batista M. T., Cymbopogon citratus leaves: characterization of flavonoids by HPLC-PDA-ESI/MS/MS and an approach to their potential as a source of bioactive polyphenols. Food Chemistry 2008 110 3 718 728 2-s2.0-42649102637 10.1016/j.foodchem.2008.02.045
52. Abad-García B., Berrueta L. A., Garmón-Lobato S., Gallo B., Vicente F., A general analytical strategy for the characterization of phenolic compounds in fruit juices by high-performance liquid chromatography with diode array detection coupled to electrospray ionization and triple quadrupole mass spectrometry. Journal of Chromatography A 2009 1216 28 5398 5415 2-s2.0-66649087396 10.1016/j.chroma.2009.05.039
53. Ferreres F., Sousa C., Valentao P., Andrade P. B., Seabra R. M., Gil-Izquierdo A., New C -deoxyhexosyl flavones and antioxidant properties of Passiflora edulis leaf extract. Journal of Agricultural and Food Chemistry 2007 55 25 10187 10193 2-s2.0-38049063049 10.1021/jf072119y
54. Djoukeng J. D., Arbona V., Argamasilla R., Gomez-Cadenas A., Flavonoid profiling in leaves of citrus genotypes under different environmental situations. Journal of Agricultural and Food Chemistry 2008 56 23 11087 11097 2-s2.0-58949089570 10.1021/jf802382y
55. Marcucci M. C., Propolis: chemical composition, biological properties and therapeutic activity. Apidologie 1995 26 2 83 99 2-s2.0-34047229759
56. Banskota A. H., Tezuka Y., Prasain J. K., Matsushige K., Saiki I., Kadota S., Chemical constituents of Brazilian propolis and their cytotoxic activities. Journal of Natural Products 1998 61 7 896 900 2-s2.0-0031904151 10.1021/np980028c (Pubitemid 28354527)
57. Banskota A. H., Tezuka Y., Adnyana I. K., Ishii E., Midorikawa K., Matsushige K., Kadota S., Hepatoprotective and anti-Helicobacter pylori activities of constituents from Brazilian propolis. Phytomedicine 2001 8 1 16 23 2-s2.0-0035086627 (Pubitemid 32242087)
58. Popova M., Trusheva B., Antonova D., Cutajar S., Mifsud D., Farrugia C., Tsvetkova I., Najdenski H., Bankova V., The specific chemical profile of Mediterranean propolis from Malta. Food Chemistry 2011 126 3 1431 1435 2-s2.0-78751584747 10.1016/j.foodchem.2010.11.130
59. Kumazawa S., Nakamura J., Murase M., Miyagawa M., Ahn M. R., Fukumoto S., Plant origin of Okinawan propolis: honeybee behavior observation and phytochemical analysis. Naturwissenschaften 2008 95 8 781 786 2-s2.0-46749126543 10.1007/s00114-008-0383-y
60. Yazaki K., Sasaki K., Tsurumaru Y., Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 2009 70 15-16 1739 1745 2-s2.0-70350722384 10.1016/j.phytochem.2009.08.023