Abstract
Truffles (Tuber spp.) belong to the fruiting bodies of certain hypogeous ascomycetes, which may grow in ectomycorrhizal symbioses with specified shrub and tree species. Some truffles, notably Tuber melanosporum and T. aestivum, form ‘burnt’ area, also known as ‘burn’ or ‘brûlé’ around their symbiotic hosts. Increasingly focused interest has been centred on an in-depth research and study of truffle methanolic extracts and their fatty acid allelochemicals. These metabolites have been recognised as biochemical and have great influence in the burnt formation. This present chapter contributes the knowledge of truffle methanolic extracts and fatty acids regarding allelopathic activity to understand the applicability and sustainability of truffles in agricultural practices for the management of weed and plant pathogens. However, it will also be helpful to the companies specialising in the processing of truffle and the recovery and reinsertion of waste truffles through the production process for the isolation of important allelopathic compounds.
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References
An M (2005) Mathematical modelling of dose-response relationship (hormesis) in allelopathy and its application. Nonlinearity Biol Toxicol Med 3:153–172
Angelini P, Granetti B (2001) Individuation and micropropagation of some clones of Populus alba L. envisaging their use in truffle cultivation. In: Proceedings of the Fifth International Congress on the Science and cultivation of truffles, French Federation of Trufficulteurs. pp 289–292
Angelini P, Costamagna L, Ciani M (1998) Bacterial ecology of ascocarps of the Tuber sp.pl.: characterization of functional groups and their capability to metabolize sulfite and organic sulfur compounds. Ann Microbiol 48:59–65
Angelini P, Granetti B, Pagiotti R (2008) Effect of antimicrobial activity of Melaleuca alternifolia essential oil on antagonistic potential of Pleurotus species against Trichoderma harzianum in dual culture. World J Microbiol Biotechnol 24:197–202
Angelini P, Pagiotti R, Venanzoni R, Granetti B (2009) Antifungal and allelopathic effects of Asafoetida against Trichoderma harzianum and Pleurotus spp. Allelopathy J 23:357–368
Angelini P, Venanzoni R, Pagiotti R, Tirillini B, Granetti B, Donnini D (2010) Attività allelopatica, antibatterica ed antiossidante di estratti metanolici di Tuber magnatum e T. melanosporum. In: Proceeding of the 3rd International Congress on Truffle, Umbria Region, Communities of the Martani, Serano and Subasio Mountains, Spoleto, Italy, 25–28 Nov 2008. Federici typography, Terni, Italy, pp 308–314
Angelini P, Venanzoni R, Pagiotti R, Tirillini B, Granetti B, Donnini D (2010b) Biological activities of methanolic extract from Tuber aestivum, T. borchii, and T. brumale f. moschatum. Osterr Z Pilzk 19:281–290
Angelini P, De Angelis MC, Guerzoni RP, Gigante D, Rubini A, Properzi P, Venanzoni R (2014a) Wood identification of pile dwellings from the Bronze Age San Savino site (Lake Trasimeno, central Italy). Plant Biosyst 148:713–722
Angelini P, Bricchi E, Gigante D, Poponessi S, Spina A, Venanzoni R (2014b) Pollen morphology of some Amaranthaceae common in Italy. Flora Medit 24:247–272
Angelini P, Compagno R, Arcangeli A, Bistocchi G, Gargano ML, Venanzoni R, Venturella G (2016) Macrofungal diversity and ecology in two Mediterranean forest types. Plant Biosyst. doi:10.1080/11263504.2014.987844
Angelini P, Tirillini B, Properzi A, Rol C, Venanzoni R (2015) Identification and bioactivity of the growth inhibitors in Tuber spp. methanolic extracts. Plant Biosyst 149:1000–1009. doi:10.1080/11263504.2014.983575
Ashrafi ZY, Rahnavard A, Sadeghi S, Alizade HM, Mashhadi HR (2008) Study of the allelopathic potential of extracts of Azadirachta indica (Neem). Online J Biol Sci 8:57–61
Azul AM, Nunes J, Ferreira I, Coelho AS, Veríssimo P, Trovão J, Campos A, Castro P, Freitas H (2014) Valuing native ectomycorrhizal fungi as a Mediterranean forestry component for sustainable and innovative solutions. Botany 92:161–171
Belfiori B, Riccioni C, Tempesta S, Pasqualetti M, Paolocci F, Rubini A (2012) Comparison of ectomycorrhizal communities in natural and cultivated Tuber melanosporum truffle grounds. FEMS Microbiol Ecol 81:547–561
Berestetskiy AO (2008) A review of fungal phytotoxins: from basic studies to practical use. Appl Biochem Microbiol 44:453–465
Bertholdsson NO (2012) Allelopathy—a tool to improve the weed competitive ability of wheat with herbicide-resistant black-grass (Alopecurus myosuroides Huds.). Agron J 2:284–294
Bhadoria PBS (2011) Allelopathy: a natural way towards weed management. Am J Exp Agric 1:7–20
Bhattacharya SK (2013) Recent advances in shotgun lipidomics and their implication for vision research and ophthalmology. Curr Eye Res 38:417–427
Bonito G, Smith ME, Brenneman T, Rytas Vilgalys R (2012) Assessing ectomycorrhizal fungal spore banks of truffle producing soils with pecan seedling trap-plants. Plant Soil 356:357–366
Bonnet JL, Bonnemoy F, Dusser M, Bohatier J (2007) Assessment of the potential toxicity of herbicides and their degradation products to non target cells using two microorganisms, the bacteria Vibrio fischeri and the ciliate Tetrahymena pyriformis. Environ Toxicol 22:78–91
Brenna JT (2013) Fatty acid analysis by high resolution gas chromatography and mass spectrometry for clinical and experimental applications. Curr Opin Clin Nutr Metab Care 16:548–554
Büntgen U, Egli S, Camarero JM, Fischer EM, Stobbe U, Kauserud H, Tegel W, Sproll L, Stenseth NC (2012) Drought-induced decline in Mediterranean truffle harvest. Nat Clim Change 2:827–829
Busi R, Vila-Aiub MM, Beckie HJ, Gaines TA, Goggin DE, Kaundun SS, Lacoste M, Neve P, Nissen SJ, Norsworthy JK, Renton M, Shaner DL, Tranel PJ, Wright T, Yu Q, Powles SB (2013) Herbicide-resistant weeds: from research and knowledge to future needs. Evol Appl 6:1218–1221
Busse MD, Fiddler GO, Ratcliff AW (2004) Ectomycorrhizal formation in herbicide-treated soils of differing clay and organic matter content. Water Air Soil Pollut 152:23–34
Cahill JF (1999) Fertilization effects on interactions between above-and belowground competition in an old field. Ecology 80:466–480
Chandra S, Chatterjee P, Dey P, Bhattacharya S (2012) Allelopathic effect of Ashwagandha against the germination and radicle growth of Cicer arietinum and Triticum aestivum. Pharma Res 4:166–169
Chevalier G (1979) L’Espece Tuber aestivum Vitt.: II—Ecologie. The International Society for Mushroom. Science 10:977–993
Chevalier G (2010) La truffe d’Europe (Tuber aestivum): limites geographiques, ecologie et culture. Aust J Mycol 19:249–259
Chou CH (1999) Roles of allelopathy in plant biodiversity and sustainable agriculture. Crit Rev Plant Sci 18:609–636
Christopolous V, Psoma P, Diamandis S (2013) Site characteristics of Tuber magnatum in Greece. Acta Mycol 48:27–32
Comandini O, Contu M, Rinaldi AC (2006) An overview of Cistus ectomycorrhizal fungi. Mycorrhiza 16:381–395
Cruz-Ortega R, Lara-Núñez A, Anaya AL (2007) Allelochemical stress can trigger oxidative damage in receptor plants: mode of action of phytotoxicity. Plant Signal Behav 2:269–270
Cullere L, Ferreira V, Chevret B, Venturini ME, Sánchez-Gimeno AC, Blanco D (2010) Characterisation of aroma active compounds in black truffles (Tuber melanosporum) and summer truffles (Tuber aestivum) by gas chromatography-olfactometry. Food Chem 122:300–306
Desbois AD, Smith VJ (2010) Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential. Appl Microbiol Biotechnol 85:1629–1642
Duke SO, Scheffler BE, Dayan FE (2001) Allelochemicals as herbicides. In: Bonjoch NP, Reigosa MJ (eds). 1st European OECD Allelopathy Symposium: Physiological aspects of allelopathy, Vigo, Spain. Printed by Gamesal, SA. pp 47–59
Duke SO, Bajsa J, Pan Z (2013) Omics methods for probing the mode of action of natural and synthetic phytotoxins. J Chem Ecol 39:333–347
Eaton G, Ayres M (2002) Plasticity and constraint in growth and protein mineralization of ectomycorrhizal fungi under simulated nitrogen deposition. Mycologia 94:921–932
Figliuolo G, Trupo G, Mang S (2013) A realized Tuber magnatum niche in the upper Sinni area (South Italy). Open J Genet 3:102–110
Fouillen L, Colsch B, Lessire R (2013) The lipid world concept of plant lipidomics. Adv Bot Res 67:331–376
Garcia-Montero LG, Moreno D, Monleon VJ, Arredondo-Ruiz F (2014) Natural production of Tuber aestivum in central Spain: Pinus spp. versus Quercus spp. brûles. For Syst 23:394–399
Gerke J, Braus GH (2014) Manipulation of fungal development as source of novel secondary metabolites for biotechnology. Appl Microbiol Biotechnol 98:8443–8455
Gezer K, Kaygusuz O, Çelik A, Işiloğlu M (2014) Ecological characteristics of truffles growing in Denizli Province, Turkey. J Food Agric Environ 12:1105–1109
Gogan AC, Nagy Z, Dégi Z, Bagi I, Dimény J (2012) Ecological characteristics of a Hungarian summer truffle (Tuber aestivum Vittad.) producing area. Acta Mycol 47:133–138
Granetti B, De Angelis A, Materozzi G (2005) Umbria terra di tartufi. Assessorato Regionale Agricoltura, Foreste, Caccia e Pesca, Umbra, p 303
Gryndler M, Hršelová H, Soukupová L, Streiblová E, Valda S, Borovička J, Gryndlerová H, Gažo J, Miko M (2011) Detection of summer truffle (Tuber aestivum Vittad.) in ectomycorrhizae and in soil using specific primers. FEMS Microbiol Lett 318:84–91
Hall IR, Brown GT, Zambonelli A (2007) Taming the truffle, the history, lore and science of the ultimate mushroom. Timber Press, Portland
Han X, Yang K, Gross RW (2012) Multi-dimensional mass spectrometry-based shotgun lipidomics and novel strategies for lipidomic analyses. Mass Spectrom Rev 31:134–178
Hartler J, Tharakan R, Köfeler HC, Graham DR, Thallinger GG (2013) Bioinformatics tools and challenges in structural analysis of lipidomics MS/MS data. Brief Bioinform 14:375–390
Heisey RM, Deprank J, Putnam AR (1985) A survey of soil microorganisms for herbicidal activity. In: Thompson AC (ed) The chemistry of allelopathy. American Chemical Society, Washington, DC
Hilszczanska D, Rosa-Gruszecka A, Szmidla H (2014) Characteristic of Tuber spp. localities in natural stands with emphasis on plant species composition. Acta Mycol 49:267–277
Iotti M, Lancellotti E, Hall I, Zambonelli A (2010) The ectomycorrhizal community in natural Tuber borchii grounds. FEMS Microbiol Ecol 72:250–260
Iotti M, Leonardi M, Oddis M, Salerni E, Baraldi E, Zambonelli A (2012) Development and validation of a real-time PCR assay for detection and quantification of Tuber magnatum in soil. BMC Microbiol 12:1471–2180
Iotti M, Leonardi M, Lancellotti E, Salerni E, Oddis M, Leonardi P, Perini C, Pacioni G, Zambonelli A (2014) Spatio-temporal dynamic of Tuber magnatum mycelium in natural truffle grounds. PLoS One 9:e115921
Jeandroz S, Murat C, Wang Y, Bonfante P, Le Tacon F (2008) Molecular phylogeny and historical biogeography of the genus Tuber, the ‘true truffles’. J Biogeogr 35:815–829
Kakisawa H, Asari F, Kusumi T, Toma T, Sakurai T, Oohusa T, Hara Y, Chihara M (1988) An allelopathic fatty-acid from the brown alga Cladosiphon okamuranus. Phytochemistry 27:731–735
Keller NP, Turner G (2012) Fungal secondary metabolism: methods and protocols, methods in molecular biology, vol 944. Springer, New York
Khaliq A, Matloob A, Aslam F, Mushtaq MN, Khan MB (2012) Toxic action of aqueous wheat straw extract on horse e purslane. Planta Daninha 30:269–278
Khanh TD, Elzaawely AA, Chung IM, Ahn JK, Tawata S, Xuan TD (2007) Role of allelochemical for weed management in rice. Allelopathy J 19:85–96
Kim KW, Kim KU (2000) Searching for rice allelochemicals. In: Kim KU, Shin DH (eds), Proceedings of the international workshop on rice allelopathy, Tageu, Korea, pp 73–78
Lam SM, Shui G (2013) Lipidomics as a principal pool for advancing biomedical research. J Genet Genomics 40:375–390
Lawrynowicz M, Krzyszczyk T, Faldziński M (2008) Occurrence of black truffles in Poland. Acta Mycol 43:143–151
Le Tacon F, Zeller B, Plain C, Hossann C, Bréchet C, Robin C (2013) Carbon transfer from the host to Tuber melanosporum mycorrhizas and ascocarps followed using a 13C pulse-labeling technique. PLoS One 8:e64626
Li ZH, Wang Q, Xiao R, Pan CD, Jiang DA (2010) Phenolics and plant allelopathy. Molecules 15:8933–8952
Li M, Zhou Z, Nie H, Bai Y, Liu H (2011) Recent advances of chromatography and mass spectrometry in lipidomics. Anal Bioanal Chem 399:243–249
Lynch JM, Clark SJ (1984) Effects of microbial colonization of barley (Hordeum vulgare L.) roots on seedling growth. J Appl Bacteriol 56:47–52
Macias FA, Chinchilla N, Varela RM, Molinillo JMG (2006) Bioactive steroids from Oryza sativa L. Steroids 71:603–608
Mamoun M, Olivier JM (1997) Mycorrhizal inoculation of cloned hazels by Tuber melanosporum: effect of soil disinfestation and co-culture with Festuca ovina. Plant Soil 188:221–226
Mardani R, Yousefi AR, Fotovat R, Oveisi M (2014) New bioassay method to find the allelopathic potential of wheat cultivars on rye (Secale cereale L.) seedlings. Allelopathy J 33:53–62
Martin JF, García-Estrada C, Zeilinger S (2014) Biosynthesis and molecular genetics of fungal secondary metabolites. Springer, New York
Milenkovic M, Marjanović Ž, Grebenc T, Glišić A (2009) Ecological specifity and molecular diversity of truffles (genus Tuber) originating from mid-west of the Balkan Peninsula. Sidowia 62:67–87
Molisch H (1937) The influence of one plant on another: allelopathy. Scientific Publishers, India
Mominul Islam AKM, Kato-Noguchi H (2013) Plant growth inhibitory activity of medicinal plant Hyptis suaveolens: could allelopathy be a cause. Emir J Food Agric 25:692–701
Muller CH (1966) The role of chemical inhibition (allelopathy) in vegetational composition. Bull Torrey Bot Club 93:332–351
Murat C, Rubini A, Riccioni C, De la Varga H, Akroume E, Belfiori B, Guaragno M, Le Tacon F, Robin C, Halkett F, Martin F, Paolocci F (2013) Fine-scale spatial genetic structure of the black truffle (Tuber melanosporum) investigated with neutral microsatellites and functional mating type genes. New Phytol 199:176–187
Noguchi HK (2008) Allelochemicals released from rice plants. Jpn J Plant Sci 2:18–25
Olivera A, Fischer CR, Bonet JA, Martìnez de Aragòn J, Oliach D, Colinas C (2011) Weed management and irrigation are key treatment in emerging black truffle (Tuber melanosporum) cultivation. New For 42:227–239
Olivera A, Bonet JA, Palacio L, Liu B, Colinas C (2014) Weed control modified Tuber melanosporum mycelial expansion in young oak plantations. Ann For Sci 71:495–504
Olivier JPM, Savignac JC, Sourzat P (2012) Truffe et trufficulture. Fanlac, Périgueux, France, p 398
Otsing E, Tedersoo L (2015) Temporal dynamics of ectomycorrhizal fungi and persistence of Tuber melanosporum in inoculated Quercus robur seedlings in North Europe. Mycorrhiza 25:61–66
Pagiotti R, Angelini P, Rubini A, Tirillini B, Granetti B, Venanzoni R (2011) Identification and characterisation of human pathogenic filamentous fungi and susceptibility to Thymus schimperi essential oil. Mycoses 54:e364–e376
Parlade J, De la Varga H, De Miguel AM, Sáez R, Pera J (2013) Quantification of extraradical mycelium of Tuber melanosporum in soils from truffle orchards in northern Spain. Mycorrhiza 23:99–106
Payen T, Murat C, Bonito G (2014) Truffle phylogenomics: new insights into truffle evolution and truffle life cycle. In: Martin F (ed) Advances in botanical research, vol 70. Elsevier Academic Press, London, pp 211–234
Perotto S, Angelini P, Bianciotto V, Bonfante P, Girlanda M, Kull T, Mello A, Pecoraro L, Perini C, Persiani A, Saitta A, Sarrocco S, Vannacci G, Venanzoni R, Venturella G, Selosse MA (2013) Interactions of fungi with other organisms. Plant Biosyst 147:208–218
Picco AM, Angelini P, Ciccarone C, Franceschini A, Ragazzi A, Rodolfi M, Varese GC, Zotti M (2011) Biodiversity of emerging pathogenic and invasive fungi in plants, animals and humans in Italy. Plant Biosyst 145:988–996
Piltaver A, Ratosa I (2006) A contribution to better knowledge of hypogeous fungi in Slovenia. J For 64:303–312
Quintana N, Kassis EG, Stermitz FR, Vivanco JM (2009) Phytotoxic compounds from roots of Centaurea diffusa Lam. Plant Signal Behav 4:9–14
Reicosky DC, Allmaras RR, Shrestha A (2003) Advances in tillage research in North American cropping systems. In: Shrestha A (ed) Cropping systems: trends and advances. Part I. Haworth, New York, pp 75–125
Reigosa MJ, Pedrol N, González L (2006) Allelopathy: a physiological process with ecological implications. Springer, Dordrecht, The Netherlands, pp 451–463
Reyna S, Garcia-Barreda S (2014) Black truffle cultivation: a global reality. For Syst 23:317–328
Ribeiro B, de Pinho PG, Andrade PB, Baptista P, Valentão P (2009) Fatty acid composition of wild edible mushrooms species: a comparative study. Microchem J 93:29–35
Ricard JM, Bergounoux F, Callot G, Chevalier G, Olivier JM, Pargney JC, Sourzat P (2003) La Truffe. Guide technique de trufficulture. Centre Technique Interprofessionnel Fruits Légumes, Paris
Rice EL (1984) Allelopathy, 2nd edn. Academic, London, UK, p 422
Rice EL (1995) Biological control of weeds and plant diseases: advances in applied allelopathy. University of Oklahoma Press, Oklahoma
Rubini A, Paolocci F, Riccioni C, Vendramin GG, Arcioni S (2005) Genetic and phylogeographic structures of the symbiotic fungus Tuber magnatum. Appl Environ Microbiol 71:6584–6589
Rubini A, Belfiori B, Riccioni C, Arcioni S, Martin F, Paolocci F (2011) Tuber melanosporum: mating type distribution in a natural plantation and dynamics of strains of different mating types on the roots of nursery-inoculated host plants. New Phytol 189:723–735
Salam MA, Kato-Noguchi H (2010) Allelopathic potential of methanol extract of Bangladesh rice seedlings. Asian J Crop Sci 2:70–77
Salerni E, Gardin L, Baglioni F, Perini C (2013) Effects of wild boar grazing on the yield of summer truffle (Tuscany, Italy). Acta Mycol 48:73–80
Sancholle M, Weete JD, Kulifaj M, Montant C (1988) Changes in lipid composition during ascocarp development of the truffle Tuber melanosporum. Mycologia 80:900–903
Schone C, Höfler H, Walch A (2013) MALDI imaging mass spectrometry in cancer research: combining proteomic profiling and histological evaluation. Clin Biochem 46:539–545
Selim SM, Zayed MS, Atta HM (2012) Evaluation of phytotoxicity of compost during composting process. J Nat Sci 10:69–77
Splivallo R (2008) Biological significance of truffle secondary metabolites. In: Karlowsky P (ed) Secondary metabolites in soil ecology Part III. Springer, Berlin, pp 141–165
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 C, Bossi S, Bonfante P (2007b) Truffle volatiles inhibit growth and induce an oxidative burst in Arabidopsis thaliana. New Phytol 175:417–424
Splivallo R, Ottonello S, Mello A, Karlovsky P (2011) Truffle volatiles: from chemical ecology to aroma biosynthesis. New Phytol 189:688–699
Stobbe U, Stobbe A, Sproll L, Tegel W, Peter M, Büntgen U, Egli S (2013) New evidence for the symbiosis between Tuber aestivum and Picea abies. Mycorrhiza 23:669–673
Storch J, McDermott L (2009) Structural and functional analysis of fatty acid-binding proteins. J Lipid Res 50S:S126–S131
Streiblova E, Gryndlerová H, Valda S, Gryndler M (2010) Tuber aestivum—hypogeous fungus. Czech Mycol 61:163–173
Streiblova E, Gryndlerová H, Gryndler M (2012) Truffle brûlé: an efficient fungal life strategy. FEMS Microbiol Ecol 80:1–8
Tang Y, Li YY, Li HM, Wan DJ, Tang YJ (2011) Comparison of lipid content and fatty acid composition between Tuber fermentation mycelia and natural fruiting bodies. J Agric Food Chem 59:4736–4742
Taschen E, Sauve M, Taudiere A, Parlade J, Selosse M, Richard F (2015) Whose truffle is this. Distribution patterns of ECM fungal diversity in Tuber melanosporum brûlés developed in multi-host Mediterranean plant communities. Environ Microbiol 17:2747–2761
Ullrich F, Grosch W (1987) Identification of the most intense volatile flavour compounds formed during autoxidation of linoleic acid. Eur Food Res Technol 184:277–282
Weden C, Chevalier G, Danell E (2004) Tuber aestivum (syn. T. uncinatum) biotopes and their history on Gotland, Sweden. Mycol Res 108:304–310
Yun W, Liu PG (2009) Achievements and challenges of research on truffles in China. Acta Bot Yunnanica 16S:1–9
Zacchi L, Vaughan-Martini A, Angelini P (2003) Yeast distribution in a truffle field ecosystem. Ann Microbiol 53:275–282
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Angelini, P. et al. (2016). Isolation and Identification of Allelochemicals from Ascocarp of Tuber Species. In: Hakeem, K., Akhtar, M. (eds) Plant, Soil and Microbes. Springer, Cham. https://doi.org/10.1007/978-3-319-29573-2_11
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