Partial identification of antifungal compounds from Punica granatum peel extracts

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 19, 2012, Pages 4841-4848

  Glazer, Ira ^a,c   Masaphy, Segula ^a,d   Marciano, Prosper ^a,d   Bar Ilan, Igal ^a,d   Holland, Doron ^b   Kerem, Zohar ^c   Amir, Rachel ^a,d  

^a MIGAL GALILEE TECHNOLOGY CENTER   (Israel)

^b VOLCANI CENTER   (Israel)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^d TEL HAI COLLEGE   (Israel)

Author keywords

antifungal activity; hydrolyzable tannins; polyphenol; pomegranate; Punica granatum L.; punicalagin

Indexed keywords

ANTI-FUNGAL ACTIVITY; HYDROLYZABLE TANNINS; POLYPHENOLS; POMEGRANATE; PUNICA GRANATUM L.; PUNICALAGIN;

FUNGI; LIQUID CHROMATOGRAPHY;

SOLVENT EXTRACTION;

FUNGICIDE; PLANT EXTRACT; PUNICALAGIN; TANNIN;

ALTERNARIA; ARTICLE; ASCOMYCETES; CHEMISTRY; DRUG EFFECT; FRUIT; FUSARIUM; ISOLATION AND PURIFICATION; LYTHRACEAE; MICROBIOLOGY; PHYSIOLOGY; PLANT DISEASE;

ALTERNARIA; ASCOMYCOTA; FRUIT; FUNGICIDES, INDUSTRIAL; FUSARIUM; HYDROLYZABLE TANNINS; PLANT DISEASES; PLANT EXTRACTS; PUNICACEAE;

ALTERNARIA ALTERNATA; FUNGI; FUSARIUM; LYTHRACEAE; PLEOSPORA TARDA; PUNICA GRANATUM;

EID: 84861167205     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf300330y     Document Type: Article

References (46)

1. Samy, R. P.; Gopalakrishnakone, P. Therapeutic potential of plants as anti-microbials for drug discovery Evidence-Based Compl. Alt. Med. 2008, 7, 283-294
2. Wu, F.; Munkvold, G. P. Mycotoxins in ethanol co-products: modeling economic impacts on the livestock industry and management strategies J. Agric. Food Chem. 2008, 56, 3900-3911
3. Falandysz, J. Residues of hexachlorobenzene in baltic fish and estimation of daily intake of this compound and pentachlorobenzene with fish and fishery products in Poland Pol. J. Environ. Stud. 2000, 9, 377-383
4. Unnikrishnan, V.; Nath, B. Hazardous chemicals in foods Indian J. Dairy Biosci. 2002, 11, 155-158
5. Tripathi, P.; Dubey, N. K. Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of fruit and vegetables Postharvest Biol. Technol. 2004, 32, 235-245
6. Abou-Jawdah, Y.; Sobh, H.; Salameh, A. Antimycotic activities of selected plant flora, growing wild in Lebanon, against phytopathogenic fungi J. Agric. Food Chem. 2002, 50, 3208-3213
7. Al-Zoreky, N. S. Antimicrobial activity of pomegranate (Punica granatum L.) fruit peels Int. J. Food Microbiol. 2009, 134, 244-248
8. Braga, L. C.; Shupp, J. W.; Cummings, C.; Jett, M.; Takahashi, J. A.; Carmo, L. S.; Chartone-Souza, E.; Nascimento, A. M. Pomegranate extract inhibits Staphylococcus aureus growth and subsequent enterotoxin production J. Ethnopharmacol. 2005, 96, 335-339
9. Fazeli, M. R.; Bahmani, S.; Jamalifar, H.; Samadi, N. Effect of probiotication on antioxidant and antibacterial activities of pomegranate juices from sour and sweet cultivars Nat. Prod. Res. 2011, 25, 288-297
10. Navarro, V.; Villarreal, M. L.; Rojas, G.; Lozoya, X. Antimicrobial evaluation of some plants used in Mexican traditional medicine for the treatment of infectious diseases J. Ethnopharmacol. 1996, 53, 143-147
11. Reddy, M. K.; Gupta, S. K.; Jacob, M. R.; Khan, S. I.; Ferreira, D. Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L Planta Med. 2007, 73, 461-467
12. Vasconcelos, L. C.; Sampaio, F. C.; Sampaio, M. C.; Pereira Mdo, S.; Higino, J. S.; Peixoto, M. H. Minimum inhibitory concentration of adherence of Punica granatum Linn (pomegranate) gel against S. mutans, S. mitis and C. albicans Braz. Dent. J. 2006, 17, 223-227
13. Vasconcelos, L. C.; Sampaio, M. C.; Sampaio, F. C.; Higino, J. S. Use of Punica granatum as an antifungal agent against candidosis associated with denture stomatitis Mycoses 2003, 46, 192-196
14. Voravuthikunchai, S.; Lortheeranuwat, A.; Jeeju, W.; Sririrak, T.; Phongpaichit, S.; Supawita, T. Effective medicinal plants against enterohaemorrhagic Escherichia coli O157:H7 J. Ethnopharmacol. 2004, 94, 49-54
15. Duman, A. D.; Ozgen, M.; Dayisoylu, K. S.; Erbil, N.; Durgac, C. Antimicrobial activity of six pomegranate (Punica granatum L.) varieties and their relation to some of their pomological and phytonutrient characteristics Molecules 2009, 14, 1808-1817
16. Azzouz, M. A.; Bullerman, L. B. Comparative antimycotic effects of selected herbs, spices, plant components and commercial antifungal agents J. Food Prot. 1982, 45, 1298-1306
17. Tayel, A. A.; El-Baz, A. F.; Salem, M. F.; El-Hadary, M. H. Potential applications of pomegranate peel extract for the control of citrus green mold J. Plant Dis. Prot. 2009, 116, 252-256
18. Tayel, A. A.; Salem, M. F.; El-Tras, W. F.; Brimer, L. Exploration of islamic medicine plant extracts as powerful antifungals for the prevention of mycotoxigenic Aspergilli growth in organic silage J. Sci. Food Agric. 2011, 91, 2160-2165
19. Jayaprakasha, G. K.; Negi, P. S.; Jena, B. S. Antimicrobial activities of pomegranate. In Pomegranates: Ancient Roots to Modern Medicine; Seeram, N. P.; Schulman, R. N.; Heber, D., Eds.; CRC Press: Boca Raton, FL, 2006; pp 167-183.
20. Osorioa, E.; Floresa, M.; Hernndeza, D.; Venturab, J.; Rodrgiez, R.; Aguilar, C. N. Biological efficiency of polyphenolic extracts from pecan nuts shell (Carya Illinoensis), pomegranate husk (Punica granatum) and creosote bush leaves (Larrea tridentata Cov.) against plant pathogenic fungi Ind. Crops Prod. 2010, 31, 153-157
21. Tehranifar, A.; Selahvarzi, Y.; Kharrazi, M.; Bakhsh, V. J. High potential of agro-industrial by-products of pomegranate (Punica granatum L.) as the powerful antifungal and antioxidant substances Ind. Crops Prod. 2011, 34, 1523-1527
22. Tzulker, R.; Glazer, I.; Bar-Ilan, I.; Holland, D.; Aviram, M.; Amir, R. Antioxidant activity, polyphenol content, and related compounds in different fruit juices and homogenates prepared from 29 different pomegranate accessions J. Agric. Food Chem. 2007, 55, 9559-9570
23. Holland, D.; Hatib, K.; Bar-Ya'akov, I. Pomegranate: botany, horticulture, breeding. In Horticultural Reviews; Wiley: 2009; pp 127-191.
24. Ben Nasr, C.; Ayed, N.; Metche, M. Quantitative determination of the polyphenolic content of pomegranate peel Z. Lebensm. Unters. Forsch. 1996, 203, 374-378
25. Runyoro, D. K. B; Matee, M. I.; Ngassapa, O. D.; Joseph, C. C; Mbwambo, Z. H. Screening of Tanzanian medicinal plants for anti- Candida activity BMC Compl. Alt. Med. 2006, 6, 11-12
26. Endo, E. H.; Cortez, D. A.; Ueda-Nakamura, T.; Nakamura, C. V.; Dias Filho, B. P. Potent antifungal activity of extracts and pure compound isolated from pomegranate peels and synergism with fluconazole against Candida albicans Res. Microbiol. 2010, 161, 534-540
27. Ishida, K.; de Mello, J. C.; Cortez, D. A.; Filho, B. P.; Ueda-Nakamura, T.; Nakamura, C. V. Influence of tannins from Stryphnodendron adstringens on growth and virulence factors of Candida albicans J. Antimicrob. Chemother. 2006, 58, 942-949
28. Gil, M. I.; Tomas-Barberan, F. A.; Hess-Pierce, B.; Holcroft, D. M.; Kader, A. A. Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing J. Agric. Food Chem. 2000, 48, 4581-4589
29. Labuda, R.; Hudec, K.; Pieckova, E.; Mezey, J.; Bohovic, R.; Mateova, S.; Lukac, S. S. Penicillium implicatum causes a destructive rot of pomegranate fruits Mycopathologia 2004, 157, 217-223
30. Dafny-Yalin, M.; Glazer, I.; Bar-Ilan, I.; Kerem, Z.; Holland, D.; Amir, R. Color, sugars and organic acids composition in aril juices and peel homogenates prepared from different pomegranate accessions J. Agric. Food Chem. 2010, 58, 4342-4352
31. Seeram, N. P.; Zhang, Y.; Reed, J. D.; Krueger, C. G.; Vaya, J. Pomegranate phytochemicals. In Pomegranates: Ancient Roots to Modern Medicine; Seeram, N. P.; Heber, D., Eds.; Taylor and Francis Group: New York, 2006; pp 3-29.
32. Buzzini, P.; Arapitsas, P.; Goretti, M.; Branda, E.; Turchetti, B.; Pinelli, P.; Ieri, F.; Romani, A. Antimicrobial and antiviral activity of hydrolysable tannins Mini Rev. Med. Chem. 2008, 8, 1179-1187
33. Latte, K. P.; Kolodziej, H. Antifungal effects of hydrolysable tannins and related compounds on dermatophytes, mould fungi and yeasts Z. Naturforsch. C 2000, 55, 467-472
34. Puupponen-Pimia, R.; Nohynek, L.; Alakomi, H. L.; Oksman-Caldentey, K. M. Bioactive berry compounds - novel tools against human pathogens Appl. Microbiol. Biotechnol. 2005, 67, 8-18
35. Yegen, O.; Berger, B.; Heitefuss, R. Investigations on the fungitoxicity of extracts of 6 selected plants from Turkey against phytopathogenic fungi J. Plant Dis. Prot. 1992, 99, 349-359
36. Seeram, N. P.; Henning, S. M.; Zhang, Y.; Suchard, M.; Li, Z.; Heber, D. Pomegranate juice ellagitannin metabolites are present in human plasma and some persist in urine for up to 48 h J. Nutr. 2006, 136, 2481-2485
37. Machado, T. B.; Pinto, A. V.; Pinto, M. C.; Leal, I. C.; Silva, M. G.; Amaral, A. C.; Kuster, R. M.; Netto-dosSantos, K. R. In vitro activity of Brazilian medicinal plants, naturally occurring naphthoquinones and their analogues, against methicillin-resistant Staphylococcus aureus Int. J. Antimicrob. Agents 2003, 21, 279-284
38. Asres, K.; Bucar, F.; Edelsbrunner, S.; Kartnig, T.; Hoger, G.; Thiel, W. Investigations on antimycobacterial activity of some Ethiopian medicinal plants Phytother. Res. 2001, 15, 323-326
39. Burapadaja, S.; Bunchoo, A. Antimicrobial activity of tannins from Terminalia citrina Planta Med. 1995, 61, 365-366
40. Machado, T. B.; Leal, I. C.; Amaral, A. C.; dos Santos, K. R.; da Silva, M. G.; Kuster, R. M. Antimicrobial ellagitannin of Punica granatum fruits J. Braz. Chem. Soc. 2002, 13, 606-610
41. Taguri, T.; Tanaka, T.; Kouno, I. Antimicrobial activity of 10 different plant polyphenols against bacteria causing food-borne disease Biol. Pharm. Bull. 2004, 27, 1965-1969
42. Voravuthikunchai, S. P.; Sririrak, T.; Limsuwan, S.; Supawita, T.; Iida, T.; Honda, T. Inhibitory effects of active compounds from Punica granatum pericarp on verocytotoxin production by enterohemorrhagic Escherichia coli O157:H7 J. Health Sci. 2005, 51, 590-596
43. Naz, S.; Siddiqi, R.; Ahmad, S.; Rasool, S. A.; Sayeed, S. A. Antibacterial activity directed isolation of compounds from Punica granatum J. Food Sci. 2007, 72, M341-M345
44. Jacob, M. R.; Walker, L. A. Natural products and antifungal drug discovery. In Antifungal Agents: Methods and Protocols; Ernst, E. J.; Rogers, P. D., Eds.; Humana: Totowa, NJ, 2005; Vol. 118, pp 83-109.
45. Kolodzeij, H.; Kayser, O.; Latte, K. P.; Ferreira, D. Evaluation of the antimicrobial potency of tannins and related compounds using the microdilution broth method Planta Med. 1999, 65, 444-446
46. Lin, L. T.; Chen, T. Y.; Chung, C. Y.; Noyce, R. S.; Grindley, T. B.; McCormick, C.; Lin, T. C.; Wang, G. H.; Lin, C. C.; Richardson, C. D. Hydrolyzable tannins (chebulagic acid and punicalagin) target viral glycoprotein-glycosaminoglycan interactions to inhibit herpes simplex virus 1 entry and cell-to-cell spread J. Virol. 2011, 85, 4386-4398