Acyclic sesquiterpenes released by Candida albicans inhibit growth of dermatophytes

Medical Mycology

Volumn 52, Issue 1, 2014, Pages 46-55

  Brasch, Jochen ^a   Horter, Felix ^a   Fritsch, Daniel ^a   Beck Jendroschek, Vera ^a   Tröger, Armin ^b   Francke, Wittko ^b  

^a UNIVERSITY HOSPITAL SCHLESWIG HOLSTEIN   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

antifungals; dihydrofarnesol; enantiomers; farnesol; Fungi; semiochemicals

Indexed keywords

2,3 DIHYDROFARNESOL; BETA FARNESENE; FARNESOL; FLUCONAZOLE; NEROLIDOL; SESQUITERPENE; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; DERMATOPHYTE; DRUG SYNTHESIS; ENANTIOMER; FUNGUS GROWTH; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MICROSPORUM CANIS; MICROTITER PLATE ASSAY; TRICHOPHYTON MENTAGROPHYTES; TRICHOPHYTON RUBRUM; ANTIBIOSIS; ARTHRODERMATACEAE; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MASS FRAGMENTOGRAPHY; METABOLISM; MICROBIAL SENSITIVITY TEST;

ANTIBIOSIS; ANTIFUNGAL AGENTS; ARTHRODERMATACEAE; CANDIDA ALBICANS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; SESQUITERPENES;

EID: 84942125055     PISSN: 13693786     EISSN: 14602709     Source Type: Journal    
DOI: 10.3109/13693786.2013.814174     Document Type: Article

References (37)

1. Schaufuss P, Brasch J, Steller U. Dermatophytes can trigger cooperative (CAMP-like) haemolytic reactions. Brit J Dermatol 2005; 153: 584-590.
2. de Hoog GS, Guarro J, Gene J, Figueras MJ. Atlas of Clinical Fungi, 2nd edn. Utrecht, The Netherlands: Centraalbureau voor Schimmelcultures, and Reus, Spain: Universitat Rovira i Virgili, 2000.
3. Pawliszyn J. Solid Phase Microextraction: Theory and Practice, 1997: New York: Wiley.
4. Bergström G, Kullenberg B, Ställberg-Stenhagen S et al. Studies on natural compounds II. Identification of a 2, 3-dihydrofarnesol as the main component of the marking perfume of male bumble bees of the speciesBombus terrestris L. Arkiv for Kemi 1968; 28: 453-469.
5. Ahlquist L, Ställberg-Stenhagen S. Studies on natural odoriferous compounds III. Synthesis of (+)-and (-)-3, 7, 11-trimethyl-6-trans-10- dodecadien-1-ol. Acta Chem Scand 1971; 25: 1685-1694.
6. Takaya H, Ohta T, Sayo N et al. Enantioselective hydrogenation of allylic and homoallylic alcohols. J Amer Chem Soc 1987; 109: 1596-1597.
7. Mashima K, Kusano K, Ohta T et al. Synthesis of new cationic BINAP-ruthenium(II)complexes and their use in asymmetric hydrogenation[BINAP = 2, 2'-bis(diphenylphosphino)-1, 1'-binaphthyl]. J Chem Soc Chem Commun 1989; 15: 1208-1210.
8. Fritz P, Beck-Jendroschek V, Brasch J. Inhibition of dermatophytes by the antimicrobial peptides human ß-defensin-2, ribonuclease 7 and psoriasin. Med Mycol 2012; 50: 579-584.
9. Ramage G, Saville SP, Wickes BL et al. Inhibition of Candida albicans biofilm formation by farnesol, a quorum-sensing molecule. Appl Environ Microbiol 2002; 68: 5459-5463.
10. Davis-Hanna A, Piispanen AE, Stateva LI et al. Farnesol and dodecanol effects on the Candida albicans Ras1-cAMP signalling pathway and the regulation of morphogenesis. Mol Microbiol 2008; 67: 47-62.
11. De Sordi L, Mühlschlegel FA. Quorum sensing and fungal-bacterial interactions in Candida albicans: a communicative network regulating microbial coexistence and virulence. FEMS Yeast Res 2009; 9: 990-999.
12. Cugini C, Morales DK, Hogan DA. Candida albicans-produced farnesol stimulates Pseudomonas quinolone signal production in LasR-defective Pseudomonas aeruginosa strains. Microbiology 2010; 156: 3096-3107.
13. Lindsay AK, Deveau A, Piispanen AE et al. Farnesol and cyclic AMP signaling effects on the hypha-to-yeast transition in Candida albicans. Eukaryot Cell 2012; 11: 1219-1225.
14. Albuquerque P, Casadevall A. Quorum sensing in fungi-a review. Med Mycol 2012; 50: 337-345.
15. Weber K, Schulz B, Ruhnke M. The quorum-sensing molecule E, E-farnesol-its variable secretion and its impact on the growth and metabolism of Candida species. Yeast 2010; 27: 727-739.
16. Akiyama H, Oono T, Huh WK et al. Actions of farnesol and xylitol against Staphylococcus aureus. Chemotherapy 2002; 48: 122-128.
17. Inoue Y, Shiraishi A, Hada T et al. The antibacterial effects of terpene alcohols on Staphylococcus aureus and their mode of action. FEMS Microbiol Lett 2004; 237: 325-331.
18. Semighini CP, Hornby JM, Dumitru R et al. Farnesol-induced apoptosis in Aspergillus nidulans reveals a possible mechanism for antagonistic interactions between fungi. Mol Microbiol 2006; 59: 753-764.
19. Jabra-Rizk MA, Meiller TF, James CE et al. Effect of farnesol on Staphylococcus aureus biofilm formation and antimicrobial susceptibility. Antimicrob Agents Chemother 2006; 50: 1463-1469.
20. Weber K, Sohr R, Schulz B, Fleischhacker M et al. Secretion of E, E-farnesol and biofilm formation in eight different Candida species. Antimicrob Agents Chemother 2008; 52: 1859-1861.
21. Derengowski LS, De-Souza-Silva C, Braz SV et al. Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis. Ann Clin Microbiol Antimicrob 2009; 8: 13.
22. Dinamarco TM, Goldman MH, Goldman GH. Farnesol-induced cell death in the filamentous fungus Aspergillus nidulans. Biochem Soc Trans 2011; 39: 1544-1548.
23. Sharma M, Prasad R. The quorum-sensing molecule farnesol is a modulator of drug efflux mediated by ABC multidrug transporters and synergizes with drugs in Candida albicans. Antimi-crob Agents Chemother 2011; 55: 4834-4843.
24. Cordeiro RA, Teixeira CE, Brilhante RS et al. Minimum inhibitory concentrations of amphotericin B, azoles and caspofun-gin against Candida species are reduced by farnesol. Med Mycol 2013; 51: 53-59.
25. Reisch J, Bergenthal D, Adesina SK et al. Constituents of Fa-gara macrophylla and Zanthoxylum rigidifolcum pericarps. J Nat Prod 1986; 49: 1169-1171.
26. Knudsen JT, Eriksson R, Gershenzon J et al. Diversity and distribution of floral scent. The Bot Rev 2006; 72: 1-20.
27. El-Sayed AM. 2012. The Pherobase: database of insect pheromones and semiochemicals. http://www.pherobase.com
28. Goodwin TE, Rasmussen EL, Guinn AC et al. African elephant sesquiterpenes. J Nat Prod 1999; 62: 1570-1572.
29. Bagnères AG, Billen J, Morgan ED. Volatile secretion of Dufour gland of workers of an army ant, Dorylus (annoma) molestus. J Chem Ecol 1991; 17: 1633-1639.
30. Keegans SJ, Billen J, Morgan ED et al. Volatile glandular secretions of three species of new world army ants, Ecitón burchelli, Labidus coecus, and Labidus praedator. J Chem Ecol 1993; 19: 2705-2719.
31. Francke W, Lübke G, Schröder W et al. Identification of oxygen containing volatile cephalic secretions of workers of Brazilian stingless bees. J Braz Chem Soc 2000; 11: 562-571.
32. Bergström G, Bergmann P, Schmidt JO. Labial gland chemistry of three species of bumble bees (Hymenoptera: Apidae) from North America. Bioorg Med Chem 1996; 4: 515-519.
33. Urbanová K, Halík J, Hovorka O et al. Marking pheromones of the cuckoo bumble bee males (Hymenoptera, Apoidea, Bombus Latreille): composition of labial gland secretions of six species found in the Czech Republic. Biochem System Ecol 2004; 32: 1025-1045.
34. Luxová A, Urbanová K, Valterová I et al. Absolute configuration of chiral terpenes in marking pheromones of bumble bees and cuckoo bumble bees. Chirality 2004; 16: 228-233.
35. Harada M, Matsuda H, Yamamoto T. Takasago Inter. Corp. Tokyo 17.10.2002. Document Identification DE 6962 1673T2 EP Nr. 073 1160.
36. Mori K. Significance of chirality in pheromone science. Bioorg Med Chem 2007; 15: 7505-7523.
37. Mori K. Bioactive natural products and chirality. Chirality 2011; 23: 449-462.