Truffles contain endocannabinoid metabolic enzymes and anandamide

Phytochemistry

Volumn 110, Issue , 2015, Pages 104-110

  Pacioni, Giovanni ^a   Rapino, Cinzia ^b,c,e   Zarivi, Osvaldo ^a   Falconi, Anastasia ^b   Leonardi, Marco ^a   Battista, Natalia ^b,d   Colafarina, Sabrina ^a   Sergi, Manuel ^b   Bonfigli, Antonella ^a   Miranda, Michele ^a   Barsacchi, Daniela ^b   Maccarrone, Mauro ^d,e  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b UNIVERSITY OF TERAMO   (Italy)

^c Stem TeCh Group   (Italy)

^d IRCCS FONDAZIONE SANTA LUCIA   (Italy)

^e UNIVERSITY CAMPUS BIO MEDICO   (Italy)

Author keywords

Endocannabinoids; Evolution; Food intake; Maturation; Reward; Truffle

Indexed keywords

ASCOMYCOTA; FUNGI; TUBER (TRUFFLE); TUBER MELANOSPORUM;

2-ARACHIDONYLGLYCEROL; ACYLGLYCEROL; AMIDE; ANANDAMIDE; ARACHIDONIC ACID DERIVATIVE; ENDOCANNABINOID;

ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; ISOLATION AND PURIFICATION; ITALY;

ARACHIDONIC ACIDS; ASCOMYCOTA; ENDOCANNABINOIDS; GLYCERIDES; ITALY; MOLECULAR STRUCTURE; POLYUNSATURATED ALKAMIDES;

EID: 84921496853     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.11.012     Document Type: Article

References (61)

1. M. Bari, M. Tedesco, N. Battista, N. Pasquariello, M. Pucci, V. Gasperi, M.L. Scaldaferri, D. Farini, M. De Felici, and M. Maccarrone Characterization of the endocannabinoid system in mouse embryonic stem cells Stem Cells Dev. 20 2011 139 147
2. N. Battista, M. Di Tommaso, M. Bari, and M. Maccarrone The endocannabinoid system: an overview Front. Behav. Neurosci. 6 2012 9
3. A.A. Bell, J.E. Puhalla, W.J. Tolmsoff, and R.D. Stipanovic Use of mutants to establish (+)-scytalone as an intermediate in melanin biosynthesis by Verticillium dahliae Can. J. Microbiol. 22 1976 787 799
4. G. Bonito, M.E. Smith, M. Nowak, R.A. Healy, G. Guevara, E. Cázares, A. Kinoshita, E.R. Nouhra, L.S. Domínguez, L. Tedersoo, C. Murat, Y. Wang, B.A. Moreno, D.H. Pfister, K. Nara, A. Zambonelli, J.M. Trappe, and R. Vilgalys Historical biogeography and diversification of truffles in the Tuberaceae and their newly identified southern hemisphere sister lineage PLoS One 8 2013 e52765
5. D. Czesnik, D. Schild, J. Kuduz, and I. Manzini Cannabinoid action in the olfactory epithelium Proc. Natl. Acad. Sci. U. S. A. 104 2007 2967 2972
6. C. D'Addario, M.V. Milioni Di Bonaventura, M. Pucci, A. Romano, S. Gaetani, R. Ciccocioppo, C. Cifani, and M. Maccarrone Endocannabinoid signaling and food addiction Neurosci. Biobehav. Rev. 47C 2014 203 224
7. F. De Angelis, A. Arcadi, F. Marinelli, M. Paci, D. Botti, G. Pacioni, and M. Miranda Partial structures of truffle melanins Phytochemistry 43 1996 1103 1106
8. M.A. De Luca, M. Solinas, Z. Bimpisidis, S.R. Goldberg, and G. Di Chiara Cannabinoid facilitation of behavioral and biochemical hedonic taste responses Neuropharmacology 63 2012 161 168
9. V. Di Marzo, and L. De Petrocellis Endocannabinoids as regulators of transient receptor potential (TRP) channels: a further opportunity to develop new endocannabinoid-based therapeutic drugs Curr. Med. Chem. 17 2010 1430 1449
10. M.R. Elphick, Y. Satou, and N. Satoh The invertebrate ancestry of endocannabinoid signalling: an orthologue of vertebrate cannabinoid receptors in the urochordate Ciona intestinalis Gene 302 2003 95 101
11. M.R. Elphick The evolution and comparative neurobiology of endocannabinoid signalling Philos. Trans. R. Soc. Lond. B Biol. Sci. 367 2012 3201 3215
12. I. Engh, M. Nowrousian, and U. Kück Regulation of melanin biosynthesis via the dihydroxynaphthalene pathway is dependent on sexual development in the ascomycete Sordaria macrospora FEMS Microbiol. Lett. 275 2007 62 70
13. K. Esser Phenol oxidases and morphogenesis in Podospora anserina Genetics 60 1968 281 288
14. E. Fride, T. Bregman, and T.C. Kirkham Endocannabinoids and food intake: newborn suckling and appetite regulation in adulthood Exp. Biol. Med. (Maywood) 230 2005 225 234
15. I. Galve-Roperh, V. Chiurchiù, J. Díaz-Alonso, M. Bari, M. Guzmán, and M. Maccarrone Cannabinoid receptor signaling in progenitor/stem cell proliferation and differentiation Prog. Lipid Res. 52 2013 633 650
16. V. Gasperi, E. Dainese, S. Oddi, A. Sabatucci, and M. Maccarrone GPR55 and its interaction with membrane lipids: comparison with other endocannabinoid-binding receptors Curr. Med. Chem. 20 2013 64 78
17. C. Gerdermann, C. Eicken, and B. Krebs The crystal structure of catechol oxidase: new insight into the function of type-3 copper proteins Acc. Chem. Res. 35 2002 183 191
18. E. Harki, T. Talou, and R. Dargent Purification, characterization and analysis of melanin extracted from Tuber melanosporum Vitt. Food Chem. 58 1997 69 73
19. E. Harki, D. Bouya, and R. Dargent Maturation-associated alterations of the biochemical characteristics of the black truffle Tuber melanosporum Vitt. Food Chem. 99 2006 394 400
20. L.J. Heung, A.E. Kaiser, C. Luberto, and M. Del Poeta The role and mechanism of diacylglycerol-protein kinase C1 signaling in melanogenesis by Cryptococcus neoformans J. Biol. Chem. 280 2005 28547 28555
21. H.M. Hirsh Environmental factors influencing the differentiation of protoperithecia and their relation to tyrosinase and melanin formation in Neurospora crassa Physiol. Plant 7 1954 72 97
22. N.H. Horowitz, H.M. Feldman, and M.L. Pall Derepression of tyrosinase in Neurospora crassa by cycloheximide, actinomycin D and puromycin J. Biol. Chem. 245 1970 2784 2788
23. A.C. Howlett, P.H. Reggio, S.R. Childers, R.E. Hampson, N.M. Ulloa, and D.G. Deutsch Endocannabinoid tone versus constitutive activity of cannabinoid receptors Br. J. Pharmacol. 163 2011 1329 1343
24. T.C. Kirkham, C.M. Williams, F. Fezza, and V. Di Marzo Endocannabinoid levels in rat limbic forebrain and hypothalamus in relation to fasting, feeding and satiation: stimulation of eating by 2-arachidonoyl glycerol Br. J. Pharmacol. 136 2002 550 557
25. T.C. Kirkham, and C. Williams Endogenous cannabinoids and appetite Nutr. Res. Rev. 14 2004 65 86
26. -ΔΔCT method Methods 25 2001 402 408
27. M. Maccarrone, G.A. Veldink, and J.F. Vliegenthart Thermal injury and ozone stress affect soybean lipoxygenases expression FEBS Lett. 309 1992 225 230
28. M. Maccarrone, E. Dainese, and S. Oddi Intracellular trafficking of anandamide: new concepts for signaling Trends Biochem. Sci. 35 2010 601 608
29. M. Maccarrone, V. Gasperi, M.V. Catani, T.A. Diep, E. Dainese, H.S. Hansen, and L. Avigliano The endocannabinoid system and its relevance for nutrition Annu. Rev. Nutr. 30 2010 423 440
30. M. Maccarrone Endocannabinoid signaling in cancer: a rather complex puzzle Trends Pharmacol. Sci. 34 2013 426 427
31. F. Martin, A. Kohler, C. Murat, R. Balestrini, P.M. Coutinho, O. Jaillon, B. Montanini, E. Morin, B. Noel, R. Percudani, B. Porcel, A. Rubini, A. Amicucci, J. Amselem, V. Anthouard, S. Arcioni, F. Artiguenave, J.M. Aury, P. Ballario, A. Bolchi, A. Brenna, A. Brun, M. Buée, B. Cantarel, G. Chevalier, A. Couloux, C. Da Silva, F. Denoeud, S. Duplessis, S. Ghignone, B. Hilselberger, M. Iotti, B. Marçais, A. Mello, M. Miranda, G. Pacioni, H. Quesneville, C. Riccioni, R. Ruotolo, R. Splivallo, V. Stocchi, E. Tisserant, A.R. Viscomi, A. Zambonelli, E. Zampieri, B. Henrissat, M.H. Lebrun, F. Paolocci, P. Bonfante, S. Ottonello, and P. Wincker Périgord black truffle genome uncovers evolutionary origins and mechanisms of symbiosis Nature 464 2010 1033 1038
32. J.M. McPartland, I. Matias, V. Di Marzo, and M. Glass Evolutionary origins of the endocannabinoid system Gene 370 2006 64 74
33. J.M. McPartland, R.W. Norris, and C.W. Kilpatrick Coevolution between cannabinoid receptors and endocannabinoid ligands Gene 397 2007 126 135
34. M. Miranda, O. Zarivi, A. Bonfigli, R. Porretta, P. Aimola, G. Pacioni, and A.M. Ragnelli White truffles, like black ones, are tyrosinase positive Plant Sci. 120 1996 29 36
35. M. Miranda, O. Zarivi, A. Bonfigli, F. Amicarelli, P. Aimola, A.M. Ragnelli, and G. Pacioni Melanogenesis, tyrosinase expression, and reproductive differentiation in black and white truffles (Ascomycotina) Pigment Cell Res. 10 1997 46 53
36. J.D. Nosanchuk, and A. Casadevall The contribution of melanin to microbial pathogenesis Cell. Microbiol. 5 2003 203 223
37. G. Pacioni, M.A. Bologna, and M. Laurenzi Insect attraction by Tuber: a chemical explication Mycol. Res. 95 1991 1359 1363
38. G. Pacioni, A.M. Ragnelli, and M. Miranda Truffle Development and Interactions with the Biotic Environment V. Stocchi, P. Bonfante, M. Nuti, Biotechnology of Ectomycorrhizae 1995 Plenum Press New York 213 227
39. N. Pasquariello, G. Catanzaro, V. Marzano, D. Amadio, D. Barcaroli, S. Oddi, G. Federici, A. Urbani, A. Finazzi Agrò, and M. Maccarrone Characterization of the endocannabinoid system in human neuronal cells and proteomic analysis of anandamide-induced apoptosis J. Biol. Chem. 284 2009 29413 29426
40. R.G. Pertwee Receptors and channels targeted by synthetic cannabinoid receptor agonists and antagonists Curr. Med. Chem. 17 2010 1360 1381
41. W.M. Pfaffl Relative quantification T. Dorak, Real-time PCR 2007 International University Line La Jolla, CA 63 82
42. R.A. Prade, A.K. Cruz, and H.F. Terenzi Regulation of tyrosinase during the vegetative and sexual life cycle of Neurospora crassa Arch. Microbiol. 140 1984 236 242
43. M. Pucci, N. Pasquariello, N. Battista, M. Di Tommaso, C. Rapino, F. Fezza, M. Zuccolo, R. Jourdain, A. Finazzi Agrò, L. Breton, and M. Maccarrone Endocannabinoids stimulate human melanogenesis via type-1 cannabinoid receptor J. Biol. Chem. 287 2012 15466 15478
44. M. Pucci, C. Rapino, A. Di Francesco, E. Dainese, C. D'Addario, and M. Maccarrone Epigenetic control of skin differentiation genes by phytocannabinoids Br. J. Pharmacol. 170 2013 581 591
45. R.A. Ross The enigmatic pharmacology of GPR55 Trends Pharmacol. Sci. 30 2009 156 163
46. J. Sambrook, and D.W. Russell Molecular Cloning: A Laboratory Manual third ed. 2001 Cold Spring Harbor New York
47. P. Seyeon, C. Hana, and K. Yun Joo Inhibition of isorhamnetin on β-catenin/Tcf signaling and β-catenin-activated melanogenesis J. Basic Appl. Sci. 9 2013 401 409
48. J.D. Simon, D. Peles, K. Wakamatsu, and S. Ito Current challenges in understanding melanogenesis: bridging chemistry, biological control, morphology, and function Pigm. Cell Melanoma Res. 22 2009 563 579
49. K. Soderstrom, Q. Tian, M. Valenti, and V. Di Marzo Endocannabinoids link feeding state and auditory perception-related gene expression J. Neurosci. 24 2004 10013 10021
50. M. Solinas, S.R. Goldberg, and D. Piomelli The endocannabinoid system in brain reward processes Br. J. Pharmacol. 154 2008 369 383
51. R. Splivallo, S. Ottonello, A. Mello, and P. Karlovsky Truffle volatiles: from chemical ecology to aroma biosynthesis New Phytol. 189 2011 688 699
52. G. Tanda, and S.R. Goldberg Cannabinoids: reward, dependence, and underlying neurochemical mechanisms - a review of recent preclinical data Psychopharmacology 169 2003 115 134
53. J.M. Trappe, and A.W. Claridge The hidden life of truffles Sci. Am. 302 2010 78 82
54. M. Valenti, E. Cottone, R. Martinez, N. De Pedro, M. Rubio, M.P. Viveros, M.F. Franzoni, M.J. Delgado, and V. Di Marzo The endocannabinoid system in the brain of Carassius auratus and its possible role in the control of food intake J. Neurochem. 95 2005 662 672
55. M. van der Stelt, J.A. van Kuik, M. Bari, G. van Zadelhoff, B.R. Leeflang, G.A. Veldink, A. Finazzi-Agrò, J.F. Vliegenthart, and M. Maccarrone Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase J. Med. Chem. 45 2002 3709 3720
56. O. Zarivi, A. Bonfigli, S. Colafarina, P. Aimola, A.M. Ragnelli, G. Pacioni, and M. Miranda Tyrosinase expression during black truffle development: from free living mycelium to ripe fruit body Phytochemistry 72 2011 2317 2324
57. C. Zimmerman, R.A. Blanchette, T.A. Burnes, and R.L. Farrel Melanin and perithecial development in Ophiostoma piliferum Mycologia 87 1995 857 863
58. S. Xapelli, F. Agasse, L. Sardà-Arroyo, L. Bernardino, T. Santos, F.F. Ribeiro, J. Valero, J. Bragança, C. Schitine, R.A. de Melo Reis, A.M. Sebastião, and J.O. Malva Activation of type 1 cannabinoid receptor (CB1R) promotes neurogenesis in murine subventricular zone cell cultures PLoS One 8 2013 e63529
59. H. Wang, M.J. Moore, P.S. Soltis, C.D. Bell, S.F. Brockington, R. Alexandre, C.C. Davis, M. Latvis, S.R. Manchester, and D.E. Soltis Rosid radiation and the rapid rise of angiosperm-dominated forests Proc. Natl. Acad. Sci. U. S. A. 106 2009 3853 3858
60. M.H. Wheeler Comparisons of fungal melanin biosynthesis in ascomycetous, imperfect and basidiomycetous fungi Trans. Br. Mycol. Soc. 81 1983 29 36
61. N. Wikström, V. Savolainen, and M.W. Chase Evolution of the angiosperms: calibrating the family tree Proc. Biol. Sci. 268 2001 2211 2220