O-coumaric acid ester, a potential early signaling molecule in Pinus pinea and Pisolithus arhizus symbiosis established in vitro

References

• Abdul-Raman AA, Habib SA. 1989. Allelopathic effects of alfalfa (Medicago sativa) on bladygrass (Imperata cylindrica). J Chem Ecol. 15:2289–2300. doi:10.1007/BF01012082
   PubMed Web of Science ®Google Scholar
• Amalesh S, Gouranga D, Sanjoy KD. 2011. Roles of flavonoids in plants. Int J Pharm Sci Tech. 6:12–35.
   Google Scholar
• Atoui AK, Mansouri A, Boskou G, Kefalas P. 2005. Tea and herbal infusions: their antioxidant activity and phenolic profile. Food Chem. 89:27–36.
   Web of Science ®Google Scholar
• Bais HP, Loyola Vargas VM, Flores HE, Vivanco JM. 2001. Root specific metabolism: the biology and biochemistry of underground organs. In Vitro Cell Dev Biol-Plant. 37:730–741.
   Web of Science ®Google Scholar
• Bais HP, Prithiviraj B, Jha AK, Ausubel FM, Vivanco JM. 2005. Mediation of pathogen resistance by exudation of antimicrobials from roots. Nature. 434:217–221.
   PubMed Web of Science ®Google Scholar
• Barghini P, Montebove F, Ruzzi M, Schisser A. 1998. Optimal conditions for bioconversion of ferulic acid into vanillic acid by Pseudomonas fluorescens BF13 cells. Appl Microbiol Biothechnol. 49:309–314.
   Google Scholar
• Bonfante P, Genre A. 2010. Mechanisms underlying beneficial plant-fungus interactions in mycorrhizal symbiosis. Nat Commun. 4: 1–11. doi:10.1038/ncomms1046
   Web of Science ®Google Scholar
• Canuto KM, Lima MA, Silveira ER. 2010. Amburosides C-H and 6-o-protocatechuoyl coumarin from Amburana cearensis. J Braz Chem Soc. 21:1746–1753.
   Web of Science ®Google Scholar
• Castro MR, Ragonezi C, Oliveira P, Zavattieri A. 2012. Patent - method for extraction of metabolic root exudates from in vitro plant cultures of Pinus pinea L. National Institute of Industrial Property Portugal (INPI) No. 105239.
   Google Scholar
• Chambers SM, Cairney JWG. 1999. Pisolithus. In: Cairney JWG, Chambers SM, editors. Ectomycorrhizal fungi. Key genera in profile. Berlin: Springer; p. 1–31.
   Google Scholar
• Estabrook EM, Yoder JI. 1998. Plant-plant communications: rhizosphere signaling between parasitic angiosperms and their hosts. Plant Physiol. 116:1–7.
   Web of Science ®Google Scholar
• Graham TL. 1991. A rapid, high resolution high performance liquid chromatography profiling procedure for plant and microbial aromatic secondary metabolites. Plant Physiol. 95:584–593.
   PubMed Web of Science ®Google Scholar
• Harrison MJ, Dixon RA. 1993. Isoflavonoid accumulation and expression of defense gene transcripts during the establishment of vesicular-arbuscular mycorrhizal associations in roots of Medicago truncatula. Mol Plant Microbe Interact. 6:643–54.
   Web of Science ®Google Scholar
• Hassan S, Mathesius U. 2012. The role of flavonoids in root-rhizosphere signalling opportunities and challenges for improving plant–microbe interactions. J Exp Bot. 63:3429–3444. doi:10.1093/jxb/err430
   PubMed Web of Science ®Google Scholar
• Kefeli VI, Kalevitch MV, Borsari B. 2003. Phenolic cycle in plants and environment. J Cell Mol Biol. 2:13–18.
   Google Scholar
• Lagrange H, Jay-Allgmand C, Lapeyrie F. 2001. Rutin, the phenolglycoside from eucalyptus root exudates, stimulates Pisolithus hyphal growth at picomolar concentrations. New Phytol. 149:349–355.
   PubMed Web of Science ®Google Scholar
• Lloyd G, McCown, B. 1981. Commercially feasible micropropagation of mountain laurel, Kalmia latifolia, by the use of shoot tip culture. Proc Plant Prop Soc. 30:421–427.
   Google Scholar
• Lynn DG, Chang M. 1990. Phenolic signals in combination: implications for plant development. Annu Rev Plant Physiol Plant Mol Biol. 41:497–526.
   Web of Science ®Google Scholar
• Mandal SM, Chakraborty D, Dey S. 2010. Phenolic acids act as signaling molecules in plant–microbe symbioses. Plant Signal Behav. 5:359–368.
   PubMed Web of Science ®Google Scholar
• Martin F, Duplessis S, Ditengou F, Lagrange H, Voiblet C, Lapeyrie F. 2001. Developmental cross talking in the ectomycorrhizal symbiosis: signals and communication genes. New Phytol. 151:145–154.
   PubMed Web of Science ®Google Scholar
• Münzenberger B, Hammer E, Wray V, Schauer F, Schmidt J, Strack D. 2003. Detoxification of ferulic acid by ectomycorrhizal fungi. Mycorrhiza. 13:117–121.
   PubMed Web of Science ®Google Scholar
• Münzenberger B, Kotte I, Oberwinkler F. 1995. Reduction of phenolics in mycorrhizas of Larix decidua Mill. Tree Physiol. 15:191–196.
   PubMed Web of Science ®Google Scholar
• Ngoc TM, Lee I, Ha DT, Kim HJ, Min BS, Bae K. 2009. Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia. J Nat Prod. 72:1205–1208.
   PubMed Web of Science ®Google Scholar
• Niemi K, Julkunen-Tiitto R, Häggman H, Sarjala T. 2007. Suillus variegatus causes significant changes in the content of individual polyamines and flavonoids in Scots pine seedlings during mycorrhiza formation in vitro. J Exp Bot. 58:391–401.
   PubMed Web of Science ®Google Scholar
• Niemi K, Salonen M, Ernstsen A, Heinonen-Tanski H, Häggman H. 2000. Application of ectomycorrhizal fungi in rooting of Scots pine fascicular shoots. Can J For Res. 30:1221–1230.
   Web of Science ®Google Scholar
• Oliveira P, Barriga J, Cavaleiro C, Peixe A, Potes AZ. 2003. Sustained in vitro root development obtained in Pinus pinea inoculated with ectomycorrhizal fungi. Forestry. 76:579–587.
   Web of Science ®Google Scholar
• Peters NK, Frost JW, Long SR. 1986. A plant flavones, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science. 233:977–980.
   PubMed Web of Science ®Google Scholar
• Plazonić A, Bucar F, Maleš Z, Mornar A, Nigović B, Kujundžić N. 2009. Identification and Quantification of Flavonoids and Phenolic Acids in Burr Parsley (Caucalis platycarpos L.), Using High-Performance Liquid Chromatography with Diode Array Detection and Electrospray Ionization Mass Spectrometry. Molecules. 14:2466–2490.
   PubMed Web of Science ®Google Scholar
• Plett JM, Martin F. 2012. Poplar root exudates contain compounds that induce the expression of MiSSP7 in Laccaria bicolor. Plant Signal Behav. 17:12–5.
   Google Scholar
• Ragonezi C, Caldeira AT, Martins MR, Dias LS, Santos-Silva C, Ganhão E, Miralto O, Pereira I, Louro R, Klimaszewska K, Zavattieri MA. 2012. Pisolithus arhizus (Scop.) Rauschert improves growth of adventitious roots and acclimation on in vitro regenerated plantlets of Pinus pinea. Propag Ornam Plants. 12:139–147.
   Web of Science ®Google Scholar
• Ruzzi M, Barghini P, Montebove F, Schiesser Ponente A. 1997. Effect of the carbon source on the utilization of ferulic, m- and p-coumaric acids by a Pseudomonas fluorescens strain. Annali Di Microbiologia Ed Enzimologia. 47:87–96.
   Google Scholar
• Scervino J, Ponce M, Erra-Balsells R, Vierheilig H, Ocampo JA, Godeas A. 2005a. Flavonoids exclusively present in mycorrhizal roots of white clover exhibit a different effect on arbuscular mycorrhizal fungi than flavonoids exclusively present in non-mycorrhizal roots of white clover. J Plant Interact. 1:15–22.
   Web of Science ®Google Scholar
• Scervino J, Ponce M, Erra-Balsells R, Vierheilig H, Ocampo JA, Godeas A. 2005b. Flavonoids exhibit fungal species and genus specific effects on the presymbiotic growth of Gigaspora and Glomus. Mycol Res. 109:789–794.
   PubMed Web of Science ®Google Scholar
• Schützendübel A, Polle A. 2002. Plant responses to abiotic stress: heavy metal-induced oxidative stress and protection by mycorrhization. J Exp Bot. 53:1351–1365.
   PubMed Web of Science ®Google Scholar
• Seddas P, Gianinazzi-Pearson V, Schoefs B, Küster H, Wipf, D, Balu F. 2009. Communication and signaling in the plant–fungi symbiosis: the mycorrhiza. In: Baluška F, editor. Plant-environment interactions. Signaling and communication in plants. Berlin, Heidelberg: Springer; p. 45–71.
   Google Scholar
• Sellami IH, Maamouri E, Chahed T, Wannes WA, Kchouk ME, Marzouk B. 2009. Effect of growth stage on the content and composition of the essential oil and phenolic fraction of sweet marjoram (Origanum majorana L.). Ind Crop Prod. 30:395.
   Web of Science ®Google Scholar
• Siqueira JO, Safir GR, Nair MG. 1991. Stimulation of vesicular-arbuscular mycorrhizae formation by flavonoid compounds. New Phytol. 118:87–93.
   Web of Science ®Google Scholar
• Tsai SM, Phillips DA. 1991. Flavonoids released naturally from alfalfa promote development of symbiotic Glomus spores in vitro. Appl Environ Microbiol. 57:1485–1488.
   PubMed Web of Science ®Google Scholar
• Vega M, De Carvalho M, Vieira I, Braz-filho R. 2008. Chemical constituents from the Paraguayan medicinal plant, Eupatorium macrocephalum Less. J Nat Med. 62:122–123
   PubMed Web of Science ®Google Scholar
• Walker TS, Bais HP, Grotewold E, Vivanco JM. 2003. Root exudation and rhizosphere biology. Plant Physiol. 132:55–51.
   Web of Science ®Google Scholar
• Zheng G, Jia Y, Zhao X, Zhang F, Luo S, Li S, Li W. 2012. O-Coumaric acid from invasive Eupatorium adenophorum is a potent phytotoxin. Chemoecology. 22:131–138.
   Web of Science ®Google Scholar
• Zeng R, Mallik A. 2006. Selected ectomycorrhizal fungi of black spruce (Picea mariana) can detoxify phenolic 484 compounds of Kalmia angustifolia. J Chem Ecol. 32:1473–1489.
   PubMed Web of Science ®Google Scholar