A prenylated flavanone from Dalea elegans inhibits rhodamine 6 G efflux and reverses fluconazole-resistance in Candida albicans

Planta Medica

Volumn 78, Issue 10, 2012, Pages 981-987

  Peralta, Mariana A ^a   Calise, Maximiliano ^b   Fornari, M Cecilia ^b   Ortega, M Gabriela ^a   Diez, Roberto A ^b   Cabrera, José L ^a   Pérez, Cristina ^b  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

antifungal activity; azole resistant Candida albicans; Dalea elegans; Fabaceae; prenylated flavonoid; reversion of fluconazole resistance; rhodamine efflux inhibition

Indexed keywords

2',4' DIHYDROXY 5' (1''',1''' DIMETHYLALLYL) 6 PRENYLPINOCEMBRIN; 6 PRENYLPINOCEMBRIN; ABC TRANSPORTER; FLAVONOID; FLUCONAZOLE; HESPERETIN; NARINGENIN; PINOCEMBRINE; RHODAMINE 6G; UNCLASSIFIED DRUG; VERAPAMIL;

ANTIFUNGAL ACTIVITY; ANTIFUNGAL RESISTANCE; ARTICLE; CANDIDA ALBICANS; CDR1P GENE; CDR2P GENE; CELL GROWTH; CONCENTRATION RESPONSE; CONTROLLED STUDY; DALEA ELEGANS; DRUG EFFECT; DRUG INHIBITION; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; FABACEAE; GENE; GENE EXPRESSION; GROWTH INHIBITION; IC 50; MDR1P GENE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRENYLATION;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; COLONY COUNT, MICROBIAL; DRUG RESISTANCE, FUNGAL; FABACEAE; FLAVANONES; FLUCONAZOLE; FUNGAL PROTEINS; HUMANS; INHIBITORY CONCENTRATION 50; MEMBRANE TRANSPORT PROTEINS; MICROBIAL SENSITIVITY TESTS; PLANT COMPONENTS, AERIAL; PLANT ROOTS; PRENYLATION; RHODAMINES; VERAPAMIL;

CANDIDA ALBICANS; DALEA; FABACEAE; STAPHYLOCOCCUS AUREUS;

EID: 84863583908     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0031-1298627     Document Type: Article

References (20)

1. Cafaratti M, Ortega MG, Scarafia ME, Ariza Espinar L, Juliani H. Prenylated flavanones from Dalea elegans. Phytochemistry: 1994; 36 1083 1084 (Pubitemid 2107528)
2. Ortega MG, Scarafia ME, Juliani HR. Antimicrobial agents in Dalea elegans. Fitoterapia: 1996; 67 81 (Pubitemid 26104676)
3. Pérez C, Tiraboschi IN, Ortega MG, Agnese AM, Cabrera JL. Further antimicrobial studies of 2,4-dihidroxy-5-(1,1-dimethylallyl)-6-prenylpinocembrin from Dalea elegans. Pharm Biol: 2003; 41 171
4. Elingold I, Isollabella MP, Casanova M, Celentano AM, Pérez C, Cabrera JL, Diez RA, Dubin M. Mitochondrial toxicity and antioxidant activity of a prenylated flavonoid isolated from Dalea elegans. Chem Biol Interact: 2008; 171 294 305
5. Kim J, Sudbery P. Candida albicans, a major human fungal pathogen. J Microbiol: 2011; 49 171 177
6. White T, Holleman S, Dy F, Mirels L, Stevens D. Resistance mechanisms in clinical isolates of Candida albicans. Antimicrob Agents Chemother: 2002; 46 1704 1713 (Pubitemid 34535186)
7. Vandeputte P, Larcher G, Berges T, Renier G, Chabasse D, Bouchara JP. Mechanisms of azole resistance in a clinical isolate of Candida tropicalis. Antimicrob Agents Chemother: 2005; 49 4608 4615 (Pubitemid 41552590)
8. National Committee for Clinical and Laboratory Standards Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard M27-A, Vol. 17 Villanova National Committee for Clinical and Laboratory Standards: 1997
9. Marchetti O, Moreillon P, Glauser M, Bille J, Sanglard D. Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans. Antimicrob Agents Chemother: 2000; 44 2373 2381 (Pubitemid 30650882)
10. Sharma M, Manoharlal R, Shukla S, Puri N, Prasad T, Ambudkar S, Prasad R. Curcumin modulates efflux mediated by yeast ABC multidrug transporters and is synergistic with antifungals. Antimicrob Agents Chemother: 2009; 53 3256 3265
11. Belofsky G, Percivill D, Lewis K, Tegos GP, Ekart J. Phenolic metabolites of Dalea versicolor that enhance antibiotic activity against model pathogenic bacteria. J Nat Prod: 2004; 67 481 484 (Pubitemid 38405723)
12. Nanayakkara NPD, Burandt CL Jr., Jacob MR. Flavonoids with activity against methicillin-resistant Staphylococcus aureus from Dalea scandens var. paucifolia. Planta Med: 2002; 68 519 522 (Pubitemid 34774747)
13. Maesaki S, Marichal P, Vanden Bossche H, Sanglard D, Kohno S. Rhodamine 6 G-efflux for the detection of CDR1-overexpressing azole-resistant Candida albicans strains. J Antimicrob Chemother: 1999; 44 27 31 (Pubitemid 29353679)
14. Sanglard D, Ischer F, Monod M, Bille J. Cloning of Candida albicans genes conferring resistance to azole antifungal agents: characterization of CDR2, a new multidrug ABC transporter gene. Microbiology: 1997; 143 405 416 (Pubitemid 27092176)
15. Comte G, Daskiewicz JB, Bayet B, Conseil G, Viornery-Vanier A, Dumontet C, Di Pietro A, Barron D. C -Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance. J Med Chem: 2001; 44 763 768 (Pubitemid 32171672)
16. Ahmed-Belkacem A, Pozza A, Muñoz-Martinez F, Bates S, Castanys S, Gamarro F, Di Pietro A, Pérez-Victoria J. Flavonoid structure-activity studies identify 6-prenylchrysin and tectochrysin as potent and specific inhibitors of breast cancer resistance protein ABCG2. Cancer Res: 2005; 65 4852 4860 (Pubitemid 40740824)
17. Conseil G, Decottignies A, Jault JM, Comte G, Barron D, Goffeau A, Di Pietro A. Prenyl-flavonoids as potent inhibitors of the Pdr5 p multidrug ABC transporter from Saccharomyces cerevisiae. Biochemistry: 2000; 39 6910 6917 (Pubitemid 30390384)
18. Hansen TS, Nilsen OG. Echinacea purpurea and P-glycoprotein drug transport in Caco-2 cells. Phytother Res: 2009; 23 86 91
19. Pina-Vaz C, Goncalves Rodrigues A, Costa-de-Oliveira S, Ricardo E, Mardh P. Potent synergic effect between ibuprofen and azoles on Candida resulting from blockade of efflux pumps as determined by FUN-1 staining and flow cytometry. J Antimicrob Chemother: 2005; 56 678 685 (Pubitemid 41487768)
20. Wesoowska O, Wisniewski J, Środa K, Krawczenko A, Bielawska-Pohl A, Paprocka M, Duś D, Michalak K. 8-Prenylnaringenin is an inhibitor of multidrug resistance-associated transporters P-glycoprotein and MRP1. Eur J Pharmacol: 2010; 644 32 40