Formation of 6-n-pentyl-2H-pyran-2-one (6-PAP) and other volatiles by different Trichoderma species

Mycological Progress

Volumn 13, Issue 3, 2014, Pages 589-600

  Jeleń, Henryk ^a   Błaszczyk, Lidia ^b   Chełkowski, Jerzy ^b   Rogowicz, Katarzyna ^a   Strakowska, Judyta ^b  

^a POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

^b INSTITUTE OF PLANT GENETICS   (Poland)

Author keywords

6 n pentyl 2H pyran 2 one; Antifungal compounds; Metabolic diversity; Solid phase microextraction; Trichoderma; Volatiles

Indexed keywords

SOLANUM TUBEROSUM; TRICHODERMA; TRICHODERMA ATROVIRIDE; TRICHODERMA CITRINOVIRIDE; TRICHODERMA HAMATUM; TRICHODERMA VIRIDE;

EID: 84905026575     PISSN: 1617416X     EISSN: 18618952     Source Type: Journal    
DOI: 10.1007/s11557-013-0942-2     Document Type: Article

References (65)

1. Al-Heeti MB, Sinclair JB (1988) Antagonism between Gliocladium roseum, Trichoderma harzianum, or Trichothecium roseum and Phytophthora megasperma f. sp. glycinea. Mycopathologia 103: 135-140.
2. Benítez T, Rincón AM, Limón MC, Codón AC (2004) Biocontrol mechanisms of Trichoderma strains. Int Microbiol 7: 249-260.
3. Błaszczyk L, Popiel D, Chełkowski J, Koczyk G, Samuels GJ, Sobieralski K, Siwulski M (2011) Species diversity of Trichoderma in Poland. J Appl Genet 52: 233-243.
4. Bonnarme P, Djian A, Latrasse A, Feron G, Ginies C, Durand A, Le Quéré JL (1997) Production of 6-pentyl-a-pyrone by Trichoderma sp. from vegetable oils. J Biotechnol 156: 143-150.
5. Bruce A, Wheatley RE, Humphris SN, Hackett CA, Florence MEJ (2000) Production of volatile organic compounds by Trichoderma in media containing different amino acids and their effect on selected wood decay fungi. Holzforschung 54: 481-486.
6. Buśko M, Chełkowski J, Popiel D, Perkowski J (2008) Solid substrate bioassay to evaluate impact of Trichoderma on trichothecene mycotoxin production by Fusarium species. J Sci Food Agric 87: 536-541.
7. Citron CA, Riclea R, Brock NL, Dickschat JS (2011) Biosynthesis of acorane sesquiterpenes by Trichoderma. RSC Adv 1: 290-297.
8. Claydon N, Allan M, Hanson JR, Avent AG (1987) Antifungal alkyl pyrones of Trichoderma harzianum. Trans Br Mycol Soc 88: 503-513.
9. Collins RP, Halim AF (1972) Characterization of the major aroma constituent of the fungus Trichoderma viride (Pers.). J Agric Food Chem 20: 437-438.
10. Cooney JM, Lauren DR, Jensen DJ, Perry-Meyer LJ (1997a) Effect of harvest time, temperature, light, and spore inoculums concentration on 6-n-pentyl-2H-pyran-2-one production by Trichoderma spp. J Agric Food Chem 45: 2802-2806.
11. Cooney JM, Lauren DR, Jensen DJ, Perry-Meyer LJ (1997b) Effect of solid substrate, liquid supplement, and harvest time on 6-n-pentyl-2H-pyran-2-one (6PAP) production by Trichoderma spp. J Agric Food Chem 45: 531-534.
12. Cooney JM, Laurent DR, Di Menna ME (2001) Impact of competitive fungi on trichothecene production by Fusarium graminearum. J Agric Food Chem 49: 522-526.
13. Cutler HG, Cox RH, Crumley FG, Cole PD (1986) 6-pentyla-pyrone from Trichoderma harzianum: its plant growth inhibitory and antimicrobial properties. Agric Biol Chem 50: 2943-2945.
14. Dodd S, Lieckfeldt E, Samuels G (2003) Hypocrea atroviridis sp. nov., the teleomorph of Trichoderma atroviride. Mycologia 95: 27-40.
15. Doohan FM, Parry DW, Jenkinson P, Nicholson P (1998) The use of species-specific PCR-based assays to analyse Fusarium ear blight of wheat. Plant Pathol 47: 197-205.
16. Druzhinina IS, Kopchinskiy AG, Komoń M, Bissett J, Szakacs G, Kubicek CP (2005) An oligonucleotide barcode for species identification in Trichoderma and Hypocrea. Fungal Genet Biol 42: 813-828.
17. Druzhinina IS, Seidl-Seiboth V, Herrera-Estrella A, Horwitz BA, Kenerley CM, Monte E, Mukherjee PK, Zeilinger S, Grigoriev IV, Kubicek CP (2011) Trichoderma: the genomics of opportunistic success. Nat Rev Microbiol 16: 749-759.
18. El-Hasan A, Walker F, Schoene J, Buchenauer H (2007) Antagonistic effect of 6-pentyl-alpha-pyrone produced by Trichoderma harzianum toward Fusarium moniliforme. J Plant Dis Prot 114: 62-68.
19. El-Hassan A, Buchennauer H (2009) Action of 6-penthyl-alpha pyrone in controlling seedling blight incited by Fusarium moniliforme and inducing defence responces in maize. J Phytopathol 157: 697-707.
20. Fiedler K, Schütz E, Geh S (2001) Detection of microbial volatile organic compounds (MVOCs) produced by moulds on various materials. Int J Hyg Environ Health 204: 111-121.
21. Friedl MA, Druzhinina IS (2012) Taxon-specific metagenomics of Trichoderma reveals a narrow community of opportunistic species that regulate each other's development. Microbiology 158: 69-83.
22. Gams W, Bisset J (1998) Morphology and identification of Trichoderma. In: Harman GE, Kubicek CP (eds) Trichoderma and Gliocladium, vol 1. Taylor and Francis, London, pp 3-34.
23. Ghisalberti EL, Narbey MJ, Dewan MM, Sivasithamparam K (1990) Variability among strains of Trichoderma harzianum in their ability to reduce take-all and to produce pyrones. Plant Soil 121: 287-291.
24. Ghisalberti EL, Hockless DCR, Rowland C, White AH (1992) Harziandione, a new class of diterpene from Trichoderma harzianum. J Nat Prod 55: 1690-1694.
25. Harman G, Kubicek C (1998) Gliocladium and Trichoderma Vol 1. Basic biology, taxonomy and genetics. Taylor and Francis, London.
26. Harman GE, Howell CR, Viterbo A, Chet I, Lorito M (2004) Trichoderma species -opportunistic, avirulent plant symbionts. Nat Rev Microbiol 2: 43-56.
27. Howell CR (1998) The role of antibiosis in biocontrol. In: Harman GE, Kubicek CP (eds) Trichoderma and Gliocladium, vol 1. Taylor and Francis, London, pp 173-184.
28. Jaklitsch WM (2009) European species of Hypocrea Part I. The green-spored species. Stud Mycol 63: 1-91.
29. Jeleń H (2002) Volatile sesquiterpene hydrocarbons characteristic for Penicillium roqueforti strains producing PR toxin. J Agric Food Chem 50: 6569-6574.
30. Jeleń H (2003) Use of solid phase microextraction (SPME) for profiling fungal volatile metabolites. Lett Appl Microbiol 36: 263-267.
31. Klein D, Eveleigh DE (1998) Tichoderma and Gliocladium. In: Harman GE, Kubicek CP (eds) Trichoderma and Gliocladium, vol 1. Taylor and Francis, London, pp 57-69.
32. Kopchinskiy A, Komon M, Kubicek CP, Druzhinina IS (2005) TrichoBLAST: a multilocus database for Trichoderma and Hypocrea identifications. Mycol Res 109: 657-660.
33. Korpi A, Järnberg J, Pasanen AL (2009) Microbial volatile organic compounds. Crit Rev Toxicol 39: 139-193.
34. Kubicek CP, Komon-Zelazowska M, Druzhinina IS (2008) Fungal genus Hypocrea/Trichoderma: from barcodes to biodiversity. J Zhejiang Univ Sci B 9: 753-763.
35. Lloyd SW, Grimm CC, Klich MA, Beltz SB (2005) Fungal infections of fresh-cut fruit can be detected by the gas chromatographye mass spectrometric identification of microbial volatile organic compounds. J Food Prot 68: 1211-1216.
36. Mannina L, Segre AL, Ritieni A, Fogliano V, Vinale F, Randazzo G, Maddau L, Bottalico A (1997) A new fungal growth inhibitor from Trichoderma viride. Tetrahedron 53: 3135-3144.
37. Mauriello G, Marino R, D'Auria M, Cerone G, Rana GL (2004) Determination of volatile organic compounds from truffles via SPME-GC-MS. J Chromatogr Sci 42: 299-305.
38. Müller A, Faubert P, Hagen M, Zu Castell W, Polle A, Schnitzler JP, Rosenkranz M (2013) Volatile profiles of fungi - Chemotyping of species and ecological functions. Fungal Genet Biol 54: 25-33.
39. Nemčovič M, Jakubíková L, Víden I, Vladimír F (2008) Induction of conidiation by endogenous volatile compounds in Trichoderma spp. FEMS Microbiol Lett 284: 231-236.
40. Nirenberg HI (1976) Untersuchungen über die morphologische und biologische Differenzierung in der Fusarium-Sektion Liseola. Mitt Biol Bund Land-Forst Berlin-Dahlem 169: 1-117.
41. Papavizas GC (1985) Trichoderma and Gliocladium: biology, ecology and potential for biocontrol. Annu Rev Phytopathol 23: 23-54.
42. Polizzi V, Adams A, Picco AM, Adriaens E, Lenoir J, van Peteghem C, De Saeger S, De Kimpe N (2011) Influence of environmental conditions on production of volatiles by Trichoderma atroviride in relation with the sick building syndrome. Build Environ 46: 945-954.
43. Polizzi V, Adams A, Malysheva SV, De Saeger S, van Peteghem C, Moretti A, Picco AM, De Kimpe N (2012) Identification of volatile markers for indoor fungal growth and chemotaxonomic classification of Aspergillus species. Fungal Biol 116: 941-953.
44. Poole PR, Ward BG, Whitaker G (1998) The effects of topical treatment with 6-pentyl-2-pyrone and structural analogues on stem and postharvest rots in kiwifruit due to Botrytis cinerea. J Sci Food Agric 77: 81-86.
45. Popiel D, Kwaśna H, Chełkowski J, Ste{ogonek}pień S, Laskowska M (2008) Impact of selected antagonistic fungi on Fusarium species - toxigenic cereal pathogens. Acta Mycol 43: 29-40.
46. Ramos AS, Fiaux SB, Leite SGF (2008) Production of 6-pentyl-α-pyrone by Trichoderma harzianum in solid-state fermentation. Braz J Microbiol 39: 712-717.
47. Reino JL, Guerrero RF, Galan RH, Collado IG (2008) Secondary metabolites from species of the biocontrol agent Trichoderma. Phytochem Rev 7: 89-123.
48. Reithner B, Brunner K, Schuhmacher R, Peissl P, Seidl V, Krska R, Zeilinger S (2005) The G protein α subunit Tga1 of Trichoderma atroviride is involved in chitinase formation and differential production of antifungal metabolites. Fungal Genet Biol 42: 749-760.
49. Reithner B, Schuhmacher R, Stoppacher N, Pucher M, Brunner K, Zeilinger S (2007) Signaling via the Trichoderma atroviride mitogen-activated protein kinase Tmk1 differentially affects mycoparasitism and plant protection. Fungal Genet Biol 44: 1123-1133.
50. Samuels GJ (2006) Trichoderma: systematics, the sexual state, and ecology. Phytopathology 96: 195-206.
51. Scarselletti R, Faull JL (1994) In vitro activity of 6-pentyl-a-pyrone, a metabolite of Trichoderma harzianum, in the inhibition of Rhizoctonia solani and Fusarium oxysporum f. sp. lycopersici. Mycol Res 98: 1207-1209.
52. Serrano-Carreon L, Hathout Y, Bensoussan M, Belin JM (1992) Production of 6-pentyl-α-pyrone by Trichoderma harzianum from 18: n fatty acids methyl esters. Biotechnol Lett 14: 1019-1024.
53. Siddiquee S, Umi KY, Kausar H, Sarwar J (2009) In vitro studies on the potential Trichoderma harzianum for antagonistic properties against Ganoderma boninense. J Food Agric Environ 7: 970-976.
54. Siddiquee S, Cheong BE, Taslima K, Kausar H, Hasan MM (2012) Separation and identification of volatile compounds from liquid cultures of Trichoderma harzianum by GC-MS using three different capillary columns. J Chromatogr Sci 50: 358-367.
55. Simon A, Dunlop RW, Ghisalberti EL, Sivasithamparam K (1988) Trichoderma koningii produces a pyrone compound with antibiotic properties. Soil Biol Chem 20: 263-264.
56. Ste{ogonek}pień Ł, Popiel D, Koczyk G, Chełkowski J (2008) Wheat-infecting Fusarium species in Poland-their chemotypes and frequencies revealed by PCR assay. J Appl Genet 49: 433-441.
57. Ste{ogonek}pień Ł, Koczyk G, Waśkiewicz A (2011) Genetic variation of Fusarium proliferatum isolates from different host species - analysis of growth rate and fumonisin production. J Appl Genet 52: 487-496.
58. Stoppacher N, Kluger B, Zeilinger S, Krska R, Schuhmacher R (2010) Identification and profiling of volatile metabolites of the biocontrol fungus Trichoderma atroviride by HS-SPME-GC-MS. J. Microbiol Methods 81: 187-193.
59. Sunesson AL, Vaes WHJ, Nilson CA, Blomquist G, Anderson B, Carlson R (1995) Identification of volatile metabolites from five fungal species cultivated on two media. Appl Environ Microbiol 61: 2911-2918.
60. Tarus PK, Lang'at-Thoruwa CC, Wanyonyi AW, Chhabra SC (2003) Bioactive metabolites from Trichoderma harzianum and Trichoderma longibrachiatum. Bull Chem Soc Ethiop 17: 185-190.
61. Verma M, Brar SK, Tyagi RD, Surampalli RY, Valéro JR (2007) Antagonistic fungi, Trichoderma spp.: panoply of biological control. Biochem Eng J 37: 1-20.
62. Vinale F, Sivasithamparam K, Ghisalberti EL, Marra R, Woo SL, Lorito M (2008) Trichoderma- plant-pathogen interactions. Soil Biol Biochem 40: 1-10.
63. Wheatley R, Hackett C, Bruce A, Kundzewicz A (1997) Effect of substrate composition on production of volatile organic compounds from Trichoderma spp. Inhibitory to wood decay fungi. Int Biodeterior Biodegrad 39: 199-205.
64. 14C]-6-pentyl-2-pyrone in liquid cultures of Trichoderma harzianum. J Agric Food Chem 46: 3747-3749.
65. Worasatit N, Sivasithamparam K, Ghisalberti EL, Rowland C (1994) Variation in pyrone production, lytic enzymes and control of Rhizoctonia root rot of wheat among single-spore isolates of Trichoderma koningii. Mycol Res 98: 1357-1363.