Abstract
Both fungi and bacteria emit many volatile organic compounds (VOCs) as mixtures of low molecular mass alcohols, aldehydes, esters, terpenoids, thiols, and other small molecules that easily volatilize. Most determination (separation and identification) of VOCs now relies on gas chromatography–mass spectrometry (GC-MS) but developments in “electronic nose” technology promise to revolutionize the field. Microbial VOC profiles are both complex and dynamic: the compounds produced and their abundance vary with the producing species, the age of the colony, water availability, the substrate, the temperature, and other environmental parameters. The single most commonly reported volatile from fungi is 1-octen-3-ol which is a breakdown product of linoleic acid. It functions as a hormone within many fungal species, serves as both an attractant and deterrent for certain species of arthropods, and exhibits toxicity at relatively low concentrations in model systems. Bacterial and fungal VOCs have been studied by scientists from a broad range of subdisciplines in both theoretical and applied contexts. VOCs are exploited for their food and flavor properties, their use as indirect indicators of microbial growth, their ability to stimulate plant growth, and their ability to attract insect pests. Because these compounds can diffuse a long way from their point of origin, they are excellent chemical signaling molecules (semiochemicals) in non-aqueous habitats and facilitate the ability of microbes to engage in “chemical conversations.” The physiological effects of bacterial and fungal VOCs in host–pathogen relationships and in mediating interspecific associations in natural ecosystem functioning is an emerging frontier for future research.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Abramson D, Sinha RN, Mills JT (1980) Mycotoxin and odor formation in moist cereal grain during granary storage. Cereal Chem 57:346–351
Abramson D, Sinha RN, Mills JT (1983) Mycotoxin and odor formation in barley stored at 16 and 20 % moisture in Manitoba. Cereal Chem 60:350–355
Agrios GN (2008) Plant pathology, 5th edn. Academic, San Diego
Aldrich JR (1988) Chemical ecology of the heteroptera. Annu Rev Entomol 33:211–238
Allen PJ (1957) Properties of a volatile fraction of uredospores of Puccinia graminis var. tritici affecting their germination and development. I. Biological activity. Plant Physiol 32:385–389
Arora K, Chand S, Malhotra BD (2006) Recent developments in bio-molecular electronics techniques for food pathogens. Anal Chim Acta 568:259–274
Assaf S, Hadar Y, Dosoretz CG (1997) 1-Octen-3-ol and 13-hydroperoxylinoleate are products of distinct pathways in the oxidative breakdown of linoleic acid by Pleurotus pulmonarius. Enzyme Microb Technol 21:484–490
Atmosukarto I, Castillo U, Hess W, Sears J, Strobel G (2005) Isolation and characterization of Muscodor albus I-41.3s, a volatile antibiotic producing fungus. Plant Sci 169:854–861
Bacon CW, White JW (eds) (2000) Microbial endophytes. Dekker, New York
Baldwin IT, Halitschke R, Paschold A, von Dahl CC, Preston CA (2006) Volatile signaling in plant-plant interactions: “talking trees” in the genomics era. Science 311:812–815
Banchio E, Xie X, Zhang H, Paré PW (2009) Soil bacteria elevate essential oil accumulation and emissions in sweet basil. J Agric Food Chem 57:653–657
Bassler BL, Losick R (2006) Bacterially speaking. Cell 125:237–246
Bennett JW (1983) Differentiation and secondary metabolism in mycelial fungi. In: Bennett JW, Ciegler A (eds) Secondary metabolism and differentiation in fungi. Dekker, New York, pp 1–32
Bennett JW, Bentley R (1989) What’s In a name? – microbial secondary metabolism. Adv Appl Microbiol 34:1–28
Bennett JW, Feibelman T (2001) Fungal bacterial interactions. In: Hock B (ed) The mycota, vol IX. Springer, Berlin, pp 229–240
Bentley R, Maganathan R (1981) Geosmin and methylisoborneol biosynthesis in Streptomycetes. Evidence for an isoprenoid pathway and its absence in nondifferentiating isolates. FEBS Lett 125:220–222
Berg JM, Tymoch JL, Stryer L (2007) Biochemistry. Freeman, New York
Berger RG, Drawert F, Tiefel P (1992) Naturally occurring flavours from fungi, yeasts, and bacteria. In: Patterson RLS, Charlwood BV, MacLeod G, Williams AA (eds) Bioinformation of flavours. Royal Chemistry Society, Cambridge, pp 1–20
Bloch E, Deorazio R (1994) Chemistry in a salad bowl: comparative organosulfur chemistry of garlic, onion, and shitake mushrooms. Pure Appl Chem 66:2205–2206
Bohbot JD, Dickens JC (2009) Characterization of an enantioselective odorant receptor in the yellow fever mosquito Aedes aegypti. PLoS One 4:7032
Borg-Karlson A-K, Englund F, Unelius CR (1994) Dimethyl oligosulphides, major volatiles released from Sauromatum guttatum and Phallus impudicus. Phytochemistry 35:321–323
Börjesson T, Stöllman UM, Adamek P, Kaspersson A (1989) Analysis of volatile compounds for detection of molds in stored cereals. Cereal Chem 66:300–304
Börjesson T, Stöllman UM, Schnürer J (1993) Off-odorous compounds produced by molds on oatmeal agar: identification and relation to other growth characteristics. J Agric Food Chem 41:2104–2111
Breheret S, Talou T, Rapior S, Bessiere J-M (1997) Monoterpenes in the aromas of fresh wild mushrooms. J Agric Food Chem 45:831–836
Brodhagen M, Tsitsigiannis DI, Hornung E, Goebel C, Feussner I, Keller NP (2008) Reciprocal oxylipin-mediated cross-talk in the Aspergillus–seed pathosystem. Mol Microbiol 67:378–391
Brodhun F, Feussner I (2011) Oxylipins in fungi. FEBS J 278:1047–1063
Brown WL (1968) An hypothesis concerning the function of the metapleural glands in ants. Am Nat 102:188–191
Bruce A, Verrall S, Hackett CA, Wheatley RE (2004) Identification of volatile organic compounds (VOCs) from bacteria and yeast causing growth inhibition of sapstain fungi. Holzforschung 58:193–198
Burge PS (2004) Studies on the role of fungi in sick building syndrome. Occup Environ Med 61:185–190
Camilli A, Bassler BL (2006) Bacterial small-molecule signaling pathways. Science 311:1113–1116
Champe SP, el-Zayat AA (1989) Isolation of a sexual sporulation hormone from Aspergillus nidulans. J Bacteriol 171:3982–3988
Champe SP, Rao P, Chang A (1987) An endogenous inducer of sexual development in Aspergillus nidulans. J Gen Microbiol 133:1383–1387
Chiron N, Michelot D (2005) Odeurs de champignons: chimie et rôle dans les interactions biotiques – une revue. Cryptogam Mycol 26:299–364
Chitarra GS, Abee T, Rombouts FM, Posthumus MA, Dijksterhuis J (2004) Germination of Penicillium paneum conidia is regulated by 1-octen-3-ol, a volatile self-inhibitor. Appl Environ Microbiol 70:2823–2829
Chitarra GS, Abee T, Rombouts FM, Dijksterhuis J (2005) 1-Octen-3-ol inhibits conidia germination of Penicillium paneum despite of mild effects on membrane permeability, respiration, intracellular pH, and changes the protein composition. FEMS Microbiol Ecol 54:67–75
Cho IH, Namgung H-J, Choi H-K, Kim YS (2008) Volatiles and key odorants in the pileus and stipe of pine-mushroom (Tricholoma matsutake sing). Food Chem 106:71–76
Choudhary DK, Johri BN, Prakash A (2008) Volatiles as priming agents that initiate plant growth and defence responses. Curr Sci 94:595–604
Claeson A-S, Levin J-O, Gr B, Sunesson A-L (2002) Volatile metabolites from microorganisms grown on humid building materials and synthetic media. J Environ Monit 4:667–672
Clough SJ, Schell MA, Denny TP (1994) Evidence for involvement of a volatile extracellular factor in Pseudomonas solonacearum virulence gene expression. MPMI 7:621–630
Cole R, Schweikert M (2003) Handbook of secondary fungal metabolites, vol 1–3. Academic, Amsterdam
Combet E, Henderson J, Eastwood DC, Burton KS (2006) Eight-carbon volatiles in mushrooms and fungi: properties, analysis, and biosynthesis. Mycoscience 47:317–326
Cronin DA, Ward MK (1971) The characterisation of some mushroom volatiles. J Sci Food Agric 22:477–479
de Pinho PG, Ribeiro B, Goncalves RF, Baptista P, Valentao P, Seabra RM, Andrade PB (2008) Correlation between the pattern volatiles and the overall aroma of wild edible mushrooms. J Agric Food Chem 56:1704–1712
Dicke M, Sabelis MW (1988) Infochemical terminology: based on cost–benefit analysis rather than origin of compounds? Funct Ecol 2:131–139
Dickschat JS, Martens R, Brinkhoff T, Simon M, Schulz S (2005a) Volatiles releases by Streptomyces species isolated from the North Sea. Chem Biodivers 2:837–865
Dickschat JS, Wenzel SC, Bode HB, Müller R, Schulz S (2005b) Biosynthesis of volatiles by the Myxobacterium Myxococcus xanthus. Chembiochem 5:778–787
Dowd PF, Bartelt RJ (1991) Host-derived volatiles as attractants and pheromone synergists for dried fruit beetle, Carpophilus hemipterus. J Chem Ecol 17:285–308
Dunkel M, Schmidt U, Struck S, Berger L, Gruening B, Hossbach J, Jaeger IS, Effmert U, Piechulla B, Eriksson R, Knudsen J, Preissner R (2009) SuperScent – a database of flavors and scents. Nucleic Acids Res 37(Database Issue):D291–D294
Eberhard A, Burlingame AL, Eberhard C, Kenyon GL, Nealson KH, Oppenheimer NJ (1981) Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry 20:2444–2449
Eisner T (2003) For love of insects. Harvard University Press, Cambridge
Ellis DI, Broadhurst D, Kell DB, Rowland JJ, Goodacre R (2002) Rapid and quantitative detection of the microbial spoilage of meat by Fourier transform infrared spectroscopy and machine learning. Appl Environ Microbiol 68:2822–2828
Fäldt J, Jonsell M, Nordlander G, Borg-Karlson A-K (1999) Volatiles of bracket fungi Fomitopsis pinicola and Fomes fomentarius and their functions as insect attractants. J Chem Ecol 25:567–590
Farag MA, Ryu CM, Sumner LW, Pare PW (2006) GC-MS SPME profiling of rhizobacterial volatiles reveals prospective inducers of growth promotion and induced systemic resistance in plants. Phytochemistry 67:2262–2268
Fernando WGD, Ramarathnam R, Krishnamoorthy AS, Savchuk SC (2005) Identification and use of potential bacterial organic antifungal volatiles in biocontrol. Soil Biol Biochem 37:955–964
Fiedler N, Laumbach R, Kelly-McNeil K, Lioy P, Fan Z-H, Zhang J, Ottenweller J, Ohman-Strickland P, Kipen H (2005) Health effects of a mixture of indoor air volatile organics, their ozone oxidation products, and stress. Environ Health Perspect 113:1542–1548
Fischer G, Schwalbe R, Möller M, Ostrowski R, Dott W (1999) Species-specific production of microbial volatile organic compounds (MVOC) by airborne fungi from a compost facility. Chemosphere 39:779–810
Flavier AB, Ganova-Raeva LM, Schell MA, Denny TP (1997) Hierarchial autoinduction in Ralstonia solanacearum: control of actyl- homoserine lactone production by a novel autoregulatory system responsive to 30- hydroxypalmitic acid methyl ester. J Bacteriol 179:7089–7097
Fraatz MA, Zorn H (2010) Fungal flavours. In: Hofrichter M (ed) The Mycota X: industial applications, vol X, 2nd edn, Industrial applications. Springer, Berlin Heidelberg New York, pp 249–264
Fuqua WC, Winans SC, Greenberg EP (1994) Quorum sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulators. J Bacteriol 176:269–275
Gallois A, Langlois D (1990) New results in the volatile odorous compounds of French cheeses. Lait 70:89–106
Griffin MA, Spakowicz DJ, Gianoulis TA, Strobel SA (2010) Volatile organic compound production by organisms in the genus Ascocoryne and a re-evaluation of myco-diesel production by NRRL 50072. Microbiology 156:3814–3829
Griffith RT, Jayachandran K, Shetty KG, Whitstine W, Furton KG (2007) Differentiation of toxic molds via headspace SPME-GC/MS and canine detection. Sensors 7:1496–1508
Gutiérrez-Luna FM, López-Bucio J, Altamirano-Hernández J, Valencia-Cantero E, Cruz HR, Macías-Rodríguez L (2010) Plant growth-promoting rhizobacteria modulate root-system architecture in Arabidopsis thaliana through volatile organic compound emission. Symbiosis 51:75–83
Harrison MJ (2005) Signaling in the arbuscular mycorrhizal symbiosis. Annu Rev Microbiol 59:19–42
Herrero-Garcia E, Garzia A, Cordobés S, Espeso EA, Ugalde U (2011) 8-Carbon oxylipins inhibit germination and growth, and stimulate aerial conidiation in Aspergillus nidulans. Fungal Biol 115:393–400
Hogan DA (2006) Talking to themselves: autoregulation and quorum sensing in fungi. Eukaryot Cell 5:613–619
Hooper AM, Pickett JA (2004) Semiochemistry. In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry, vol 2. Dekker, New York, pp 1270–1277
Horswill A, Stoodley P, Stewart P, Parsek M (2007) The effect of the chemical, biological, and physical environment on quorum sensing in structured microbial communities. Anal Bioanal Chem 387:371–380
Howe GA, Jander G (2008) Plant immunity to insect herbivores. Annu Rev Plant Biol 59:41–66
Hutchinson SA (1973) Biological activities of volatile fungal metabolites. Annu Rev Phytopathol 11:223–246
Inamdar AA, Masurekar P, Bennett JW (2010) Neurotoxicity of fungal volatile organic compounds in Drosophila melanogaster. Toxicol Sci 117:418–426
Inamdar AA, Moore JC, Cohen RI, Bennett JW (2011) A model to evaluate the cytotoxicity of the fungal volatile organic compound 1-octen-3-ol in human embryonic stem cells. Mycopathologia 173:13–20
IOM (2004) Damp indoor spaces and health. National Academies, Washington
Jarvis BB, Miller JD (2005) Mycotoxins as harmful indoor air contaminants. Appl Microbiol Biotechnol 66:367–372
Jeleń HH (2003) Use of solid phase microextraction (SPME) for profiling fungal volatile metabolites. Lett Appl Microbiol 36:263–267
Joblin Y, Moularat S, Anton R, Bousta F, Orial G, Robine E, Picon O, Bourouina T (2010) Detection of moulds by volatile organic compounds; application to heritage conservation. Int Biodeterior Biodegrad 64:210–217
Kai M, Haustein M, Molina F, Petri A, Scholz B, Piechulla B (2009) Bacterial volatiles and their action potential. Appl Microbiol Biotechnol 81:1001–1012
Kaminski E, LIbbey LM, Stawicki S, Wasowicz E (1972) Identification of the predominant volatile compounds produced by Aspergillus flavus. Appl Microbiol 24:721–726
Kaplan HB, Greenberg EP (1985) Diffusion of autoinducer is involved in regulation of the Vibrio fischeri luminescence system. J Bacteriol 163:1210–1214
Karahadian C, Josephson DB, Lindsay RC (1985) Contribution of Penicillium sp. to the flavour of Brie and Camembert cheese. J Dairy Sci 68:1865–1877
Karlovsky P (ed) (2008) Secondary metabolites in soil ecology. Springer, Berlin Heidelberg New York
Karlshøj K, Nielsen PV, Larsen TO (2007) Fungal volatiles biomarkers of good and bad food quality. In: Dijksterhuis J, Samson RA (eds) Food mycology. CRC, Boca Raton, pp 279–302
Karlson P, Luscher M (1959) ‘Pheromones’: a new term for a class of biologically active substances. Nature 183:55–56
Keller NP, Turner G, Bennett JW (2005) Fungal secondary metabolism – from biochemistry to genomics. Nat Rev Microbiol 3:937–947
Kesselmeier J, Staudt M (1999) Biogenic volatile organic compounds (VOC): an overview on emission, physiology and ecology. J Atmos Chem 33:23–88
Kishimoto K, Matsui K, Ozawa R, Takabayashi J (2007) Volatile 1-octen-3-ol induces a defensive response in Arabidopsis thaliana. J Gen Plant Pathol 73:35–37
Kline D, Allan SA, Bernier UR, Welch CH (2007) Evaluation of the enantiomers of 1-octen-3-ol and 1-octyn-3-ol as attractants for mosquitoes associated with a freshwater swamp in Florida, USA. Med Vet Entomol 21:323–331
Kolter R, Greenberg EP (2006) Microbial sciences: the superficial life of microbes. Nature 441:300–302
Korpi A, Jarnberg J, Pasanen A-L (2009) Microbial volatile organic compounds. Crit Rev Toxicol 39:139–193
Kües U, Navarro-González M (2009) Communication of fungi on individual, species, kingdom, and above kingdom levels. In: Anke T, Weber D (eds) The Mycota XV. Physiology and genetics. Springer, Berlin Heidelberg New York, pp 79–106
Kuske M, Romain A-C, Nicolas J (2005) Microbial volatile organic compounds as indicators of fungi. Can an electronic nose detect fungi in indoor environments? Build Environ 40:824–831
La Camera S, Gouzerh G, Sandrine D, Laurent H, Bernard F, Michel F, Thierry H (2004) Metabolic reprogramming in plant innate immunity: the contributions of phenylpropanoid and oxylipin pathways. Immunol Rev 198:267–284
Lam K, Tsang M, Labrie A, Gries R, Gries G (2010) Semiochemical-mediated oviposition avoidance by female house flies, Musca domestica, on animal feces colonized with harmful fungi. J Chem Ecol 36:141–147
Larsen TO, Frisvad JC (1995) Comparison of different methods for collection of volatile chemical markers from fungi. J Microbiol Methods 24:135–144
Lax AR, Templeton GE, Meyer WL (1985) Isolation, purification, and biological activity of a self-inhibotor from conidia of Colletotrichum gloeosporioides. Phytopathology 75:386–390
Lee SO, Kim HY, Choi GJ, Lee HB, Jang KS, Choi YH, Kim JC (2009) Mycofumigation with Oxyporus latemarginatus EF069 for control of postharvest apple decay and Rhizoctonia root rot on moth orchid. J Appl Microbiol 106:1213–1219
Leeder AC, Palma-Guerrero J, Glass NL (2011) The social network: deciphering fungal language. Nat Rev Microbiol 9:440–451
Li DW, Yang CS (2004) Fungal contamination as a major contributor to sick building syndrome. Adv Appl Microbiol 55:31–112
Liu W, Mu W, Zhu B, Liu F (2008) Antifungal activities and components of VOCs produced by Bacillus subtilis G8. Curr Res Bacteriol 1:28–34
Lugtenberg B, Kamilova F (2009) Plant-growth-promoting rhizobacteria. Annu Rev Microbiol 63:541–556
Luntz AJ (2003) Arthropod semiochemicals: mosquitoes, midges and sealice. Biochem Soc Trans 31:128–133
Mackie AE, Wheatley RE (1999) Effects and incidence of volatile organic compound interactions between soil bacterial and fungal isolates. Soil Biol Biochem 31:375–385
Mattheis JP, Roberts RG (1992) Identification of geosmin as a volatile metabolite of Penicillium expansum. Appl Environ Microbiol 58:3170–3172
Matysik S, Herbarth O, Mueller A (2008) Determination of volatile metabolites originating from mould growth on wall paper and synthetic media. J Microbiol Methods 75:182–187
Matysik S, Herbarth O, Mueller A (2009) Determination of microbial volatile organic compounds (MVOCs) by passive sampling onto charcoal sorbents. Chemosphere 76:114–119
Mau J-L, Beelman RB, Ziegler GR (1992) Effect of 10-oxo-trans-8-decenoic acid on growth of Agaricus bisporus. Phytochemistry 31:4059–4064
Mau J-L, Chyau C-C, Li J-Y, Tseng Y-H (1997) Flavor compounds in straw mushrooms Volvariella volvacea harvested at different stages of maturity. J Agric Food Chem 45:4726–4729
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
McFee DR, Zavon P (1988) Solvents. In: Plog BA (ed) Fundamentals of industrial hygiene, 3rd edn. National Safety Council, Chicago, pp 95–121
McNeal KS, Herbert BE (2009) Volatile organic metabolites as indicators of soil microbial activity and community composition shifts. Soil Sci Soc Am J 73:579–588
Meilgaard MC (1975a) Flavor chemistry of beer. I. Flavor interaction between principal volatiles. Tech Q Master Brewers Assoc Am 12:107–117
Meilgaard MC (1975b) Flavor chemistry of beer. II. Flavor and threshold of 239 aroma volatiles. Tech Q Master Brewers Assoc Am 12:151–168
Mercier J, Jiménez JI (2004) Control of fungal decay of apples and peaches by the biofumigant fungus Muscodor albus. Postharvest Biol Tec 31:1–8
Mercier J, Manker D (2005) Biocontrol of soil-borne diseases and plant growth enhancement in greenhouse soilless mix by the volatile-producing fungus Muscodor albus. Crop Prot 24:355–362
Minerdi D, Bossi S, Gullino ML, Garibaldi A (2009) Volatile organic compounds: a potential direct long-distance mechanism for antagonistic action of Fusarium oxysporum strain MSA 35. Environ Microbiol 11:844–854
Mølhave L (2009) Volatile organic compounds and the sick building syndrome. In: Lippmann M (ed) Environmental toxicants: human exposures and their health effects, 3rd edn. Wiley-Interscience, New York, pp 241–256
Morey P, Wortham A, Weber A, Horner E, Black M, Muller W (1997) Microbial VOCs in moisture damaged buildings. Health Build 1:245–250
Mosandl A, Heusinger G, Gessner M (1986) Analytical and sensory differentiation of 1-octen-3-ol enantiomers. J Agric Food Chem 34:119–122
Nealson KH, Hastings JW (1979) Bacterial bioluminescence: its control and ecological significance. Microbiol Rev 43:496–518
Nealson KH, Platt T, Hastings JW (1970) Cellular control of the synthesis and activity of the bacterial luminescent system. J Bacteriol 104:313–322
Nemcovic M, Jakubikova L, Viden I, Farkas V (2008) Induction of conidiation by endogenous volatile compounds in Trichoderma spp. FEMS Microbiol Lett 284:231–236
Nilssen AC (1998) Effect of 1-octen-3-ol in field trapping Aedes spp. (Dipt., Culicidae) and Hybomitra spp. (Dipt., Tabanidae) in subartic Norway. J Appl Entomol 122:465–468
Nilsson A, Kihlstrom E, Lagesson V, Wessen B, Szponar B, Larsson L, Tagesson C (2004) Microorganisms and volatile organic compounds in airborne dust from damp residences. Indoor Air 14:74–82
Niu Q, Huang X, Zhang L, Xu J, Yang D, Wei K, Niu X, An Z, Bennett JW, Zou C, Yang J, Zhang KQ (2010) A Trojan horse mechanism of bacterial pathogenesis against nematodes. Proc Natl Acad Sci USA 107:16631–16636
Noble R, Dobrovin-Pennington A, Hobbs PJ, Pederby J, Rodger A (2009) Volatile C8 compounds and pseudomonads influence primordium formation of Agaricus bisporus. Mycologia 101:583–591
Nordlund DA, Lewis WJ (1976) Terminology of chemical releasing stimuli in intraspecific and interspecific interactions. J Chem Ecol 2:211–220
Noverr MC, Erb-Downward JR (2003) Production of eicosanoids and other oxylipins by pathogenic eukaryotic microbes. Clin Microbiol Rev 16:517–533
Okull DO, Beelman RB, Gourama H (2003) Antifungal activity of 10-oxo-trans-8-decenoic acid and 1-octen-3-ol against Penicillium expansum in potato dextrose agar medium. J Food Prot 66:1503–1505
Oldroyd GED, Downie JA (2004) Calcium, kinases and nodulation signalling in legumes. Nat Rev Mol Cell Biol 5:566–576
Ômura H, Kuwahara Y, Tanabe T (2002) 1-Octen-3-ol together with geosmin: new secretion compounds from a polydesmid millipede, Niponia nodulosa. J Chem Ecol 28:2601–2612
Ortiz-Castro R, Contreras-Cornejo H, Macias-Rodriguez L, Lopez-Bucio J (2009) The role of microbial signals in plant growth and development. Plant Signal Behav 4:701–712
Palkova Z, Forstova J (2000) Yeast colonies synchronise their growth and development. J Cell Sci 113:1923–1928
Palkova Z, Janderova B, Gabriel J, Zikanova B, Pospisek M, Forstova J (1997) Ammonia mediates communication between yeast colonies. Nature 390:532–536
Palkova Z, Devaux F, Icicova M, Minarikova L, Le Crom S, Jacq C (2002) Ammonia pulses and metabolic oscillations guide yeast colony development. Mol Biol Cell 13:3901–3914
Pasanen P, Korpi A, Kalliokosi P, Pasanen AL (1997) Growth and volatile metabolite production of Aspergillus versicolor in house dust. Environ Int 23:425–432
Pavlou AD, Turner AP (2000) Sniffing out the truth: clinical diagnosis using the electronic nose. Clin Chem Lab Med 38:99–112
Pelaez F (2005) Biological activities of fungal metabolites. In: An Z (ed) Handbook of industrial mycology. Dekker, New York, pp 49–92
Pierce AM, Pierce HD, Borden JH, Oehlschlager AC (1991a) Fungal volatiles: semiochemicals for stored-product beetles (Coleoptera: Cucujidae). J Chem Ecol 3:567–579
Pierce AM, Pierce HD, Oehlschlager AC, Borden JH (1991b) 1-Octen-3-ol, attractive semiochemical for foreign grain beetle, Ahasverus adevna (Waltl) (Coleoptera: Cucujidae). J Chem Ecol 3:567–579
Poland TM, Pureswaran DS, Ciaramitaro TM, Borden JH (2009) 1-Octen-3-ol is repellent to Ips pini (Coleoptera: Curculionidae: Scolytinae) in the Midwestern United States. Can Entomol 141:158–160
Ramoni R, VIncent F, Grolli S, Conti V, Malosse C, Boyer F, Nagnan-Le Meillour P, Spinelli S, Cambillau C, Tegoni M (2001) The insect attractant 1-octen-3-ol is the natural ligand of bovine odorant-binding protein. J Biol Chem 276:7150
Rapior S, Breheret S, Talou T, Pelissier Y, Bessiere JM (2002) The anise-like odor of Clitocybe odora, Lentinellus cochleatus, and Agaricus essettie. Mycologia 94:373–376
Robinson J (ed) (2006) The Oxford companion to wine, 3rd edn. Oxford, Oxford University Press
Rodriguez RJ, White JF, Arnold AE, Redman RS (2009) Fungal endophytes: diversity and functional roles. New Phytol 182:314–330
Rude MA, Schirmer A (2009) New microbial fuels: a biotech perspective. Curr Opin Microbiol 12:274–281
Rumbaugh KP, Griswold JA, Hamood AN (2000) The role of quorum sensing in the in vivo virulence of Pseudomonas aeruginosa. Microbes Infect 2:1721–1731
Ryu C-M, Farag MA, Hu C-H, Reddy MS, Wei H-X, Paré PW, Kloepper JW (2003) Bacterial volatiles promote growth in Arabidopsis. Proc Natl Acad Sci USA 100:4927–4932
Ryu C-M, Farag MA, Paré PW, Kloepper JW (2005) Invisible signals from the underground: bacterial volatiles elicit plant growth promotion and induce systemic resistance. Plant Pathol J 21:7–12
Schnürer J, Olsson J, Börjesson T (1999) Fungal volatiles as indicators of food and feeds spoilage. Fungal Genet Biol 27:209–217
Schöller CEG, Gürtler H, Petersen R, Molin S, Wilkins K (2002) Volatile metabolites from Actinomycetes. J Agric Food Chem 50:2615–2621
Schreier P (1992) Bioflavours: an overview. In: Patterson RLS, Charlwood BV, MacLeod G, Williams AA (eds) Bioinformation of flavours. Royal Society of Chemistry, Cambridge, pp 1–20
Schulz S, Dickschat JS (2007) Bacterial volatiles: the smell of small organisms. Nat Prod Rep 24:814–842
Shapiro JA (1998) Thinking about bacterial populations as multicellular organisms. Annu Rev Microbiol 52:81–104
Shimkets LJ (1999) Intercellular signaling during fruiting-body development of Myxococcus xanthus. Annu Rev Microbiol 53:525–549
Singh SK, Strobel GA, Knighton B, Geary B, Sears J, Ezra D (2011) An endophytic Phomopsis sp. possessing bioactivity and fuel potential with its volatile organic compounds. Microb Ecol 61:729–739
Sneeden EY, Harris HH, Pickering J, Prince RC, Johnson S, Li X, Block E, George GH (2004) The sulfur chemistry of shitake mushroom. J Am Chem Soc 126:458–459
Splivallo R, Bossi S, Maffei M, Bonfante P (2007a) Discrimination of truffle fruiting body versus mycelial aromas by stir bar sorptive extraction. Phytochemistry 68:2584–2598
Splivallo R, Novero M, Bertea CM, Bossi S, Bonfante P (2007b) Truffle volatiles inhibit growth and induce an oxidative burst in Arabidopsis thaliana. New Phytol 175:417–424
Stinson M, Ezra D, Hess WM, Sears J, Strobel G (2003) An endophytic Gliocladium sp. of Eucryphia cordifolia producing selective volatile antimicrobial compounds. Plant Sci 165:913–922
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
Straus DC (2009) Molds, mycotoxins, and sick building syndrome. Toxicol Ind Health 25:617–635
Straus DC, Cooley JD, Wong WC, Jumper CA (2003) Studies on the role of fungi in sick building syndrome. Arch Environ Health 58:475–478
Strobel GA, Dirkse E, Sears J, Markworth C (2001) Volatile antimicrobials from Muscodor albus a novel endophytic fungus. Microbiology 147:2943–2950
Strobel GA, Knighton B, Kluck K, Ren Y, Livinghouse T, Griffin M, Spakowicz D, Sears J (2008) The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072). Microbiology 154:3319–3328
Strobel GA, Singh SK, Riyaz-Ul-Hassan S, Mitchell AM, Geary B, Sears J (2011) An endophytic/pathogenic Phoma sp. from creosote bush producing biologically active volatile compounds having fuel potential. FEMS Microbiol Lett 320:87–94
Ström G, West J, Wessen B, Palmgren U (1994) Health implications of fungi in indoor environments: quantitative analysis of microbial volatiles in damp Swedish houses. Air Qual Monogr 2:291–305
Sunesson AL, Vaes WHJ, Nilsson CA, Blomquist G, Andersson B, Carlson R (1995) Identification of volatile metabolites from five fungal species cultivated on two media. Appl Environ Microbiol 61:2911–2918
Sunesson AL, Nilsson CA, Andersson B, Blomquist G (1996) Volatile metabolites produced by two fungal species cultivated on building materials. Ann Occup Hyg 40:397–410
Takahashi N (1986) Chemistry of plant hormones. CRC, Boca Raton
Tan RX, Zou WV (2001) Endophytes: a rich source of functional metabolites. Nat Prod Rep 18:448–459
Tarkka MT, Piechulla B (2007) Aromatic weapons: truffles attack plants by the production of volatiles. New Phytol 175:381–383
Thomson NR, Crow MA, McGowan SJ, Cox A, Salmond GPC (2000) Biosynthesis of carbapenem antibiotic and prodigiosin pigment in Serratia is under quorum sensing control. Mol Microbiol 36:539–556
Thorn J (2001) The inflammatory response in humans after inhalation of bacterial endotoxin: a review. Inflamm Res 50:254–261
Tirillini B, Verdelli G, Paolocci F, Ciccioli P, Frattoni M (2000) The volatile organic compounds from the mycelium of Tuber borchii Vitt. Phytochemistry 55:983–985
Trinci APJ, Whittaker C (1968) Self-inhibition of spore germination in Aspergillus nidulans. Trans Br Mycol Soc 51:594–596
Tsitsigiannis DI, Keller NP (2007) Oxylipins as developmental and host-fungal communication signals. Trends Microbiol 15:109–118
Tsurushima T, Ueno T, Fukami H, Irie H, Inoue M (1995) Germination self-inhibitors from Colletotrichum gloeosporioides f.sp jussiaea. Mol Plant Microbe Interact 8:652–657
Turner WB (1971) Fungal metabolites. Academic, London
Turner WB, Aldridge DC (1983) Fungal metabolites II. Academic, London
Van Delden C, Iglewski BH (1998) Cell-to-cell signaling and Pseudomonas aeruginosa infections. Emerg Infect Dis 4:551–560
Vespermann A, Kai M, Piechulla B (2007) Rhizobacterial volatiles affect the growth of fungi and Arabidopsis thaliana. Appl Environ Microbiol 73:5639–5641. doi:10.1128/AEM.01078-07
von Bodman SB, Bauer WD, Coplin DL (2003) Quorum sensing in plant-pathogenic bacteria. Annu Rev Phytopathol 41:455–482
Walinder R, Ernstgard L, Johanson G, Venge P, Wieslander G (2005) Acute effects of a fungal volatile compound. Environ Health Perspect 113:1775–1778
Waters CM, Bassler BL (2005) Quorum sensing: cell-to-cell communication in bacteria. Annu Rev Cell Dev Biol 21:319–346
Watson SB, Brownlee B, Satchwill T, Hargesheimer EE (2000) Quantitative analysis of trace levels of geosmin and MIB in source and drinking water using headspace SPME. Water Res 34:2818–2828
Weeks EN, Birkett MA, Cameron MM, Pickett JA, Logan JG (2011) Semiochemicals of the common bed bug, Cimex lectularius L. (Hemiptera: Cimicidae), and their potential for use in monitoring and control. Pest Manag Sci 67:10–20
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
Whipps JM (2001) Microbial interactions and biocontrol in the rhizosphere. J Exp Bot 52(Suppl 1):487–511
Whitehead NA, Barnard ANL, Slater H, Simpson NJL, Salmond GPC (2001) Quorum-sensing in Gram-negative bacteria. FEMS Microbiol Rev 25:365–404
Whittaker RH, Feeny PP (1971) Allelochemics: chemical interactions between species. Science 171:757–770
WHO (2009) Guidelines for indoor air quality: dampness and mold. Druckpartner Moser, Germany
Wilkins K, Larsen K, Simkus M (2000) Volatile metabolites from mold growth on building materials and synthetic media. Chemosphere 41:437–446
Wilson AD, Baietto M (2009) Applications and advances in electronic-nose technologies. Sensors 9:5099–5148
Wilson AD, Baietto M (2011) Advances in electronic-nose technologies developed for biomedical applications. Sensors 11:1105–1176
Wood WF, Fesler M (1986) Mushroom odors: student synthesis of the odoriferous compounds of the matsutake mushroom. J Chem Educ 63:92
Wurzenberger M, Grosch W (1984) The formation of 1-octen-3-ol from the 10-hydroperoxide isomer of linoleic acid by a hydroperoxide lyase in mushrooms (Psalliota bispora). Biochim Biophys Acta Lipids Lipid Metab 794:25–30
Xie X, Zhang H, Pare P (2009) Sustained growth promotion in Arabidopsis with long-term exposure to the beneficial soil bacterium Bacillus subtilis (GB03). Plant Signal Behav 4:948–953
Zhang Z, Li G (2010) A review of advances and new developments in the analysis of biological volatile organic compounds. Microchem J 95:127–139
Zhang QH, Schlyter F (2004) Olfactory recognition and behavioural avoidance of angiosperm nonhost volatiles by conifer-inhabiting bark beetles. Agric For Entomol 6:1–19
Zhang Y-Q, Wilkinson H, Keller NP, Tsitsigiannis D (2005) Secondary metabolite gene clusters. In: An Z (ed) Handbook of industrial microbiology. Dekker, New York, pp 355–386
Zhang H, Kim M-S, Krishnamachari V, Payton P, Sun Y, Grimson M, Farag M, Ryu C-M, Allen R, Melo I, Paré P (2007) Rhizobacterial volatile emissions regulate auxin homeostasis and cell expansion in Arabidopsis. Planta 226:839–851
Zhang H, Xie X, Kim MS, Kornyeyev DA, Holaday S, Pare PW (2008) Soil bacteria augment Arabidopsis photosynthesis by decreasing glucose sensing and abscisic acid levels in planta. Plant J 56:264–273
Zhang CL, Wang GP, Mao LJ, Komon-Zelazowska M, Yuan ZL, Lin FC, Druzhinina IS, Kubicek CP (2010) Muscodor fengyangensis sp. nov. from southeast China: morphology, physiology and production of volatile compounds. Fungal Biol 114:797–808
Zogorski JS, Carter JM, Ivahnenko T, Lapham WW, Moran MJ, Rowe BL, Squillace PJ, Toccalino PL (2006) The quality of our nation’s waters – volatile organic compounds in the nation’s ground water and drinking-water supply wells. US Geological Survey Circular 1292. US Geological Survey, Reston
Acknowledgements
We thank Arati Inamdar, James Mauro, Prakash Masurekar, Shannon Morath, David Pu, and Alisa Schink for their intellectual insights on fungal VOCs; we thank Natalie Naranjo and Shannon Morath for their help with the references, Karl Esser for his mentorship, Berthold Hock for his editorial support, and the Rutgers University Research Fund for financial support.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Bennett, J.W., Hung, R., Lee, S., Padhi, S. (2012). 18 Fungal and Bacterial Volatile Organic Compounds: An Overview and Their Role as Ecological Signaling Agents. In: Hock, B. (eds) Fungal Associations. The Mycota, vol 9. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-30826-0_18
Download citation
DOI: https://doi.org/10.1007/978-3-642-30826-0_18
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-30825-3
Online ISBN: 978-3-642-30826-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)