Stilbene polyphenols in the brown red wood of Vitis vinifera cv. Sangiovese affected by "esca proper"

Phytopathologia Mediterranea

Volumn 50, Issue SUPPL., 2011, Pages

  Amalfitano, Carmine ^a   Agrelli, Diana ^a   Arrigo, Alessandro ^a   Mugnai, Laura ^b   Surico, Giuseppe ^b   Evidente, Antonio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Phaeoacremonium aleophilum; Phaeomoniella chlamydospora; Viniferins; Vitis vinifera

Indexed keywords

FOMITIPORIA MEDITERRANEA; PHAEOACREMONIUM ALEOPHILUM; PHAEOMONIELLA CHLAMYDOSPORA; VITACEAE; VITIS VINIFERA;

EID: 84857819650     PISSN: 00319465     EISSN: 15932095     Source Type: Journal    
DOI: None     Document Type: Article

References (62)

1. Agrelli D., C. Amalfitano, P. Conte and L. Mugnai, 2009. Chemical and spectroscopic characteristics of the wood of Vitis vinifera cv. Sangiovese affected by esca disease. Journal of Agriculture and Food Chemistry 24, 11469-11475.
2. Amalfitano C., A. Evidente, G. Surico, S. Tegli, E. Bertelli and L. Mugnai, 2000. Phenols and stilbene polyphenols in the wood of esca-diseased grapevines. Phytopatologia Mediterranea 39, 178-183.
3. Amalfitano C., R. Pengue, A. Andolfi, M. Vurro, M.C. Zonno and A. Evidente, 2002. HPLC analysis of fusaric acid, 9,10-dehydrofusaric acid and their methyl esters, toxic metabolites from weed pathogenic Fusarium species. Phytochemical Analysis 13, 277-282.
4. Amalfitano C., D. Agrelli, and A. Evidente, 2010. Risposta di difesa al mal dell'esca nella zona di infezione. In: Il Mal dell'esca della Vite. Interventi di Ricerca e Sperimentazione per il Contenimento della Malattia. (Surico G., Mugnai L., ed.). ARSIA Regione Toscana, Firenze, Italy, 296-303.
5. Bala A.E.A., A. Kollmann, P.H. Ducrot, A. Majira, L. Kerhoas, P. Leroux, R. Delorme and J. Einhorn, 2000. Cis- ε-viniferin: a new antifungal resveratrol dehydrodimer from Cyphostemma crotalarioides roots. Journal of Phytopathology 18, 29-32.
6. Barjot C., M. Tournaire, C. Castagnino, C. Vigor, J. Vercauteren and J.F. Rossi, 2007. Evaluation of antitumor effects of two vine stalk oligomers of resveratrol on a panel of lymphoid and myeloid cell lines: Comparison with resveratrol. Life Sciences 81 (23-24), 1565-1574.
7. Bavaresco L., C. Fregoni, E. Cantù and M. Trevisan, 1999. Stilbene compounds: from the grapevine to wine. Drugs Under Experimental and Clinical Research 25, 57-63.
8. Borie B., P. Jeandet, A. Parize, R. Bessis and M. Adrian, 2004. Resveratrol and Stilbene Synthase mRNA Production in Grapevine Leaves Treated with Biotic and Abiotic Phytoalexin Elicitors. American Journal of Enology and Viticulture 55, 60-64.
9. Bruno G. and L. Sparapano, 2006. Effect of three esca associated fungi on Vitis vinifera L.: III. Enzymes produced by the pathogens and their role in fungus-to-plant or in fungus-to-fungus interactions. Physiological and Molecular Plant Pathology 69, 182-194.
10. Cichewicz, R. H. and S.A. Kouzi, 2002. Resveratrol oligomers: Structure, chemistry, and biological activity. In: Studies in Natural Products Chemistry. (Atta-ur-Rahman, ed.), Elsevier Science B.V., Amsterdam, Netherlands, Vol. 26, 507-579.
11. Dawidar A.M., J. Jakupovic, M. Abdel-Mogip and I.A. Mashaly, 1994. Prenylstilbenes and prenylflavanones from Schoenus nigricans. Phytochemistry 36, 803-806.
12. Deacon J.L., 2000. Micologia Moderna. Edagricole, Bologna, Italy.
13. Deak M. and H. Falk, 2003. On the chemistry of the resveratrol diastereomers. Monatshefte fuer Chemie 134, 8883-888.
14. Delaunay J., C. Castagnono, C. Chèze and J. Vercauteren, 2002. Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography. Journal of Chromatography A 964, 123-128.
15. Edwards J, I.G. Pascoe and S. Salib, 2007. Impairment of grapevine xylem function by Phaeomoniella chlamydospora infection is due to more than physical blockage of vessels with "goo". Phytopathologia Mediterranea 46, 87-90.
16. Evidente A., L. Sparapano., A. Andolfi., G. Bruno, 2000. Two naphthalenone pentaketides from liquid cultures of Phaeoacremonium aleophilum, a fungus associated with esca of grapevine. Phytopathologia Mediterranea 39, 162-168.
17. Goodell b., J. Jellison, J. Liu, G. Daniel, A. Paszczynski, F. Fekete, S. Krishnamurth, L. Jun and G. Xu, 1997. Low molecular weight chelators and phenolic compounds isolated from wood decay fungi and their role in the fungal biodegradation of wood. Journal of Biotecnology, 53, 133-162.
18. Gottstein D. and D. Gross, 1992. Phytoalexins of woody plant. Trees 6, 55-68.
19. Ito J., M. Niwa and Y. Oshima, 1997. A new hydroxystilbene tetramer named isohopephel from Vitis vinifera Kyohou. Heterocycles 45, 1809-1813.
20. Ito J., K. Gobaru, R. Shimamura and M. Niwa, 1998. Absolute configuration of some oligostilbenes from Vitis coignetiae and Vitis vinifera Kyohou. Tetrahedron 54, 6651-6660.
21. Jeandet P., R. Bessis and B. Gautheron, 1991. The production of resveratrol (3,5,4'-trihydroxystilbene) by grape berries in different developmental stages. American Journal of Enology and Viticulture 42, 41-46.
22. Jeandet P., A. Douillet-Breuil, R. Bessis, S. Debord, M. Sbaghi and M. Adrian, 2002. Phytoalexins from the vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. Journal of Agricultural and Food Chemistry 50, 2731-2741.
23. Keckeis, K., S.D. Sarker and L. Dinan, 2000. Resveratrol-type oligostilbenes from Iris clarkei antagonize 20-hydroxyecdysone action in the Drosophila melanogaster BII cell line. Cellular and Molecular Life Sciences 57, 333-336.
24. Khan M.A., S.G. Nabi, S. Prakash and A. Zaman, 1986. Pallidol, a resveratrol dimer from Cissua pallida. Phytochemistry 25, 1945-1948.
25. Kitakana S., T. Ikezawa, K. Yslkawa, S. Yamanouchl, M. Takido, H. Kìl Sung and H. Kim, 1990. (+)-α-Viniferin, an anti-inflammatory compound from Caragana chamlagu root. Chemical and Pharmaceutical Buletin 38, 432-435.
26. Kurihara H., J. Kawabata, S. Ichikawa and J. Mizutani, 1990. (-)-ε-Viniferin and related oligostilbenes from Carex pumila Thunb. (Cyperaceae). Agricultural and Biological Chemistry 54, 1097-1099.
27. Kurihara H., J. Kawabata, S. Ichikawa, M. Mishima and J. Mizutani, 1991. Oligostilbenes from Carex kobomugi. Phytochemistry 30, 649-653.
28. Langcake P., 1981. Disease resistance of Vitis spp. and the production of the stress metabolites resveratrol, α-viniferin, ε-viniferin and pterostilbene. Physiological Plant Pathology 18, 213-226.
29. Langcake P. and W.V. McCarty, 1979. The relationship of resveratrol production to infection of grapevine leaves by Botrytis cinerea. Vitis 18, 244-253.
30. Langcake P. and R.J. Pryce, 1976. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection. Physiological Plant Pathology 9, 77-86.
31. Langcake P. and R.J. Pryce, 1977. The production of resveratrol and viniferins by grapevines in response to ultra-violet irradiations. Phytochemistry 16, 1193-1196.
32. Luini E., P. Fleurat-Lessard, L. Rousseau, G. Roblin and J.M. Berjeaud, 2010. Inhibitory effects of polypeptides secreted by the grapevine pathogens Phaeomoniella chlamydospora and Phaeoacremonium aleophilum on plant cell activities. Physiological and Molecular Plant Pathology 74, 403-411.
33. Marchi G., S. Roberti, R. D'Ovidio, L. Mugnai and G. Surico, 2001. Pectic enzymes production by Phaeomoni-ella chlamydospora. Phytopathologia Mediterranea 40, S407-S416.
34. Massarini E., 1957. Ulteriori ricerche sopra derivati stilbenici e difeniletanici. Il Farmaco XII, 5, 380-386.
35. Meng Y., P. Bourne, P. Whiting, V. Sik and L. Dinan, 2001. Identification and ecdysteroid antagonist activity of three oligostilbenes from the seeds of Carex pendula (Cyperaceae). Phytochemistry 57 (3), 393-400.
36. Mittler R., 2002. Oxidative stress, antioxidants and stress tolerance. Trends in Plant Science, 7, 405-410.
37. Mugnai L., E. Bertelli., G. Surico and E. Bruno, 1997. Effetto di alcune sostanze fenoliche sulla crescita di funghi del legno di viti colpite dal "mal dell'esca". Petria, 11, 35-46.
38. Mugnai L., A. Graniti and G. Surico, 1999. Esca (black measles) and brown wood-streaking: two old and elusive diseases of grapevines. Plant Disease 83, 404-418.
39. Ohyama M., T. Tanaka and M. Iinuma, 1995. Five resveratrol oligomers from roots of Sophora leachiana. Phytochemistry 38 (3), 733-740.
40. Oshima Y. and Y. Ueno, 1993. Ampelopsins D, E, H and cis-ampelopsin E, oligostilbenes from Ampelopsis brevipeduncolata var. Hancei roots. Phytochemistry 33, 179-182.
41. Pearce R.B., 1996. Tansley Review No. 87, Antimicrobial defences in the wood of living trees. New Phytologist 132, 203-233.
42. Péros J-P., G. Berger and I. Jamaux-Despréaux, 2008. Symptoms, wood lesions and fungi associated with esca in organic vineyards in Languedoc-Roussillon (France). Journal of Phytopathology 156, 297-303.
43. Plomion C., G. Leprovost and A. Stokes, 2001. Wood formation in trees. Plant Physiology, 127, 1513-1523.
44. Pool R.M., L.L. Creasy and A.S. Frackelton, 1981. Resveratrol and viniferins, their application to screening for disease resistance in grape breeding programs. Vitis 20, 136-145.
45. Pryce R.J., and P. Langcake, 1977. α-Viniferin an antifungal resveratrol trimer from grapevines. Phytochemistry 16, 1452-1454.
46. Reniero F., M. Rudolph, A. Angioni, A. Bernreuther, P. Cabras and F. Mattivi, 1996. Identification of two stilbenoids from Vitis roots. Vitis 35, 125-127.
47. Sakihama Y., M.F. Cohen, S.C. Grace and H. Yamasaki, 2002. Plant phenolic antioxidant and prooxidant activities: phenolics-induced oxidative damage mediated by metals in plants. Toxicology 177, 67-80.
48. Santos C., S. Fragoerio, H. Valentim and A. Phillips, 2006. Phenotypic characterisation of Phaeoacremonium and Phaeomoniella strain isolated from grapevine: enzymes production and virulence of extra-cellular filtrate on grapevine calluses. Scientia Horticulturae 107, 123-130.
49. Sarig P., Y. Zutkhi, A. Monjauze, N. Lisker and R. Ben- Arie, 1997. Phytoalexin elicitation in grape berries and their susceptibility to Rhizopus stolonifer. Physiological and Molecular Plant Pathology 50, 337-347.
50. Shortle W.C. and E.B. Cowling, 1978. Interaction of live sapwood and fungi commonly found in discolored and decayed wood. Phytopathology 68, 617-623.
51. Soleas G.J., E.P. Diamandis and D.M. Goldberg, 1997. Resveratrol: a molecule whose time has come? And gone? Clinical Biochemistry 30, 91-113.
52. Sparapano L., G. Bruno, C. Ciccarone and A. Graniti, 2000. Infection of grapevines with some esca-disease associated fungi. II. Interaction among Fomitiporia punctata, Phaeoacremonium chlamydosporum and P. aleophilum. Phytopathologia Mediterranea 39, 53-58.
53. Surico G., 2009. Towards a redefinition of the diseases within the esca complex of grapevine. Phytopathologia Mediterranea 48, 5-10.
54. Surico G., L. Mugnai and G. Marchi, 2006. Older and more recent observations on esca, a critical overview. Phytopathologia Mediterranea 45, S68-S86.
55. Tabacchi R., A. Fkyerat, C. Poliart and G.M. Dubin, 2000. Phytotoxins from fungi of esca of grapevine. Phyto-pathologia Mediterranea 39, 156-161.
56. Takaya Y., K. Yan, K. Terashima, J. Ito, Y. He, M. Tateoka, N. Yamaguchi and M. Niwa, 2005. Biomimic transformation of resveratrol. Tetrahedron 61, 10285-10290.
57. Takaya Y., K. Yan, K. Terashima, Y. He and M. Niwa, 2002. Biogenetic reactions on stilbene tetramers from Vitaceaeous plants. Tetrahedron 58, 9265-9271.
58. Trela B.C and A.L. Waterhouse, 1996. Resveratrol: isomeric molar absoptivities and stability. Journal of Agricultural and Food Chemistry 44, 1253-1257.
59. Troccoli L., R. Calamassi, B. Mori, L. Mugnai and G. Surico, 2001. Phaeomoniella chlamydospora-grapevine interaction: histochemical reactions to fungal infection. Phytopathologia Mediterranea 40, S400-S406.
60. Úrbez-Torres J.R., G.M. Leavitt, T.M. Voegel and W.D. Gubler, 2006. Identification and distribution of Botryo-sphaeria spp. associated with grapevine cankers in California. Plant Disease 90, 1490-1503.
61. Valtaud C., P. Larignon, G. Roblin and P. Fleurat-Lessard, 2009. Developmental and ultrastructural features of Phaeomoniella chlamydospora and Phaeoacremonium aleophilum in relation to xylem degradation in esca disease of the grapevine. Journal of Plant Pathology 91, 37-51.
62. Van Etten H.D., J.W. Mansfield, J.A. Bailey and E.E. Farmer, 1994. Two classes of plant antibiotics: phytoalexins versus "phytoanticipins". The Plant Cell 6, 1191-1192.