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Quantificazione Di Resveratrolo, Piceide, Pterostilbene E 11 Viniferine Indotte Da P

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Quantificazione Di Resveratrolo, Piceide, Pterostilbene E 11 Viniferine Indotte Da P L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 DOCUMENTO TECNICO 1Urska Vrhovsek 1Giulia Malacarne 1Domenico Masuero 2Luca Zulini Graziano Guella 1Marco Stefanini 1Riccardo Velasco 1Fulvio Mattivi 1Fondazione Edmund Mach, Centro Ricerca ed Innovazione - San Michele all’Adige (TN) 2Laboratorio di Chimica Bio-organica, Dipartimento di Fisica, Università di Trento U. Vrhovsek QUANTIFICAZIONE DI RESVERATROLO, PICEIDE, PTEROSTILBENE E 11 VINIFERINE INDOTTE DA P. VITICOLA IN FOGLIE DI VITI RESISTENTI Questo è il primo articolo che riporta una analisi metabolica dettagliata, con identificazione e quantificazione, delle principali viniferine presenti in foglie di vite dopo infezione con Plasmopara viticola, mediante uso degli standard corrispondenti. Lʼanalisi è stata condotta mediante LC-MS, utilizzando una colonna a fase inversa. Introduzione essere costitutiva (Pezet e et al. 1997), in particolare Pont 1988, Korhammer et al. Langcake e Pryce (1977) Gli stilbenoidi sono fenoli 1995, Mattivi et al. 1995) o hanno caratterizzato una serie derivanti dalla via metabolica indotta in risposta a stress bio- di fitoalessine con attività dei fenilpropanoidi e dell’ace- tici ed abiotici (Langcake e antifungina in diverse specie tato-malonato, che è presente Pryce 1976 Langcake e Pryce del genere Vitis. Inoltre è stato in molte famiglie di piante. 1977, Adrian et al. 1996, dimostrato che la presenza di All’interno delle Vitaceae, gli Sarig et al. 1997, Douillet- resveratrolo è strettamente stilbenoidi costituiscono un Breuil et al 1999, Cantos et al. correlata alla resistenza alle gruppo relativamente ristretto 2001) o da elicitori (Bru et al. malattie in molte specie di di molecole che derivano 2006, Zamboni et al. 2006). vite (Dercks e Creasy 1989, dalla struttura del trans-resve- Gli stilbeni hanno suscitato Adrian et al. 1997). Oltre al Parole chiave: stilbenoidi, vi- ratrolo e rappresentano le grande interesse a causa delle resveratrolo, anche altri stilbe- niferine, HPLC-DAD-MS, principali fitoalessine note. La loro proprietà antifungine noidi derivanti dalla sua dime- Vitaceae, Plasmopara viticola sintesi di stilbeni nell’uva può (Hoos e Blaich 1990, Adrian rizzazione ossidativa, sono 85 L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 Tab. 1 - Valore medio determinato sperimentalmente del coefficiente di utilizzato è il sistema di sepa- estinzione molare e picco di assorbanza degli oligomeri usati come stan- razione HPLC, accoppiato dard esterni per la quantificazione con diversi tipi di rivelatori come DAD (Jeandet et al. peak N° name Maximal Average molar 1997, Vitrac et al. 2005), fluo- absorbance extinction coefficient rescenza (Jeandet et al. 1997) (nm) at maximal absorbance e più recentemente spettrome- 1 trans-caffeic acid and (+)-catechin tri di massa (Pezet et al 2003, condensation product 281 7340 Jean-Denis et al 2007, Jerko- vic et al 2007, Godard et al 3 ampelopsin D + quadrangularin A 314 24570 2009). La maggiore difficoltà 4 isohopeaphenol 281 10930 nell’analisi delle viniferine è la mancanza di standard 5 Z-ε-viniferin 280 9920 disponibili in commercio. 6 ampelopsin H 281 12710 Questo articolo descrive lo 7 vaticanol C-like 281 14830 sviluppo di un nuovo metodo per la separazione cromato- 8(+)-E-ε-viniferin 319 30630 grafica e quantificazione 9 Z-miyabenol C 282 14030 accurata delle viniferine. A nostra conoscenza è il primo 11 Z+E-ω-viniferin 295 13950 lavoro che descrive un’analisi 12 α-viniferin 283 6270 capace di identificare e quan- tificare con accuratezza le 13 E-cis-miyabenol C 321 11100a principali viniferine accumu- late in foglie di vite in seguito ad infezione con Plasmopara Tab. 2 - Soglia di rilevabilità (LOD) e soglia di quantificazione (LOQ) per la viticola grazie all’utilizzo dei misura in UV-Vis (i valori sono espressi in mg/g fw) rispettivi standard precedente- mente isolati e caratterizzati LOD (S/N> 3) LOQ (S/N> 10) nel nostro laboratorio (Mattivi et al., 2011). trans-piceid 0.02 0.08 trans-resveratrol 0.01 0.05 Materiali pallidol (as Ampelopsin H) 0.15 0.51 ampelopsin D+ quadrangularin A (1:1) 0.05 0.15 e metodi isohopeaphenol 0.20 0.67 È stata utilizzata una popo- ampelopsin H 0.23 0.78 lazione F1 derivante dall’in- crocio interspecifico tra vaticanol C isomer (as Ampelopsin H) 0.15 0.51 Merzling (M) (un ibrido com- (+)-E-ε-viniferin 0.08 0.26 plesso di V. vinifera derivante Z-miyabenol C 0.03 0.09 da Vitis rupestris e Vitis lin- cecumii) e la cultivar di V. E-miyabenol C 0.05 0.15 vinifera Teroldego (T), che Z-ω-viniferin 0.29 0.97 sono rispettivamente parzial- E-ω-viniferin 0.15 0.49 mente resistente e suscettibile a Plasmopara viticola. Nel α-viniferin 0.41 1.36 primo anno, Merzling e gli individui F1 21/122 e 21/103 sono stati selezionati e utiliz- attivi contro vari patogeni fun- di stilbene (Stein et al. 1985). zati per ottimizzare un meto- gini della vite (Jeandet 2002). La tossicità di questi composti do per l’analisi del contenuto La variabilità nella produ- è risultata essere correlata alla di stilbeni nelle foglie dopo zione di stilbeni è anche loro struttura chimica. In par- inoculazione con P. viticola. influenzata dal genotipo e ticolare si è constatato che δ- I genotipi selezionati sono dallo stadio di sviluppo della viniferina, un dimero di ossi- stati replicati mediante talee vite (Barlass et al. 1987, dazione del resveratrolo, e innestate sul portinnesto Ko- Dercks e Creasy 1989, Sbaghi pterostilbene, e l’analogo 3,5- ber 5BB, che sono state man- et al. 1995, Gatto et al. 2008) dimetossi del resveratrolo, tenute in una camera di cre- o dall’età della foglia (Stein et sono gli stilbeni più tossici in scita in vasi da 1 litro piene al. 1985). In particolare, le termini di mobilità e sviluppo di terriccio:sabbia:tor-ba:ver- foglie molto vecchie e le della malattia causata dall’oo- miculite (3:1:3:3). Per F1 foglie più giovani sembrano micete Plasmopara viticola 21/103 sono state eseguite sintetizzare meno stilbeni (Pezet et al 2004a, 2004b, due ripetizioni, mentre per rispetto alle altre a causa della Schmidlin et al. 2008). F1 21/22 e Merzling sono maggior chiusura stomatica In letteratura si trovano state eseguite tre ripetizioni. che limita l’entrata del patoge- diversi metodi analitici per Gli individui F1 21/74 e F1 no e, indirettamente, la sintesi l’analisi delle viniferine, il più 21/103 sono stati campionati 86 L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 anche nelle due annate se- Tab. 3 - Accumulo di viniferine nelle foglie di 3 genotipi a diversi tempi dal- guenti per studiare la riprodu- l’infezione con P. viticola. I valori sono espressi in ug/g fw (n=3) cibilità in tre annate diverse. 0 2 dpi 6 dpi Inoculo fungino ed infe- zione delle piante. F1 genotype 21/122 average sd average sd average sd Sporangi di P. viticola trans-piceid nd nd 0.8 1.4 5.3 0.8 (Berk. e Curt) Berl. et De trans-resveratrol 0.2 0.4 1.73.0 8.1 1.1 Toni sono stati raccolti da foglie infette di V. vinifera pallidol (ampelopsin H) nd nd nd nd 19.24 10.70 cv Pinot Gris. Le macchie ampelopsin D+ bianche di sporulazione pre- quadrangularin A (1:1) nd nd 1.6 1.5 11.1 6.4 senti sulla pagina inferiore delle foglie sono state spaz- isohopeaphenol nd nd 12.28.8 118.1 97.5 zolate con acqua bidistillata ampelopsin H + vaticanol per ottenere una sospensione C isomer (ampelopsin H) nd nd 3.1 2.9 57.2 23.1 4 5 di conidi di 10 /10 spore/ml. (+)-E-ε-viniferin nd nd 11.1 10.8 34.5 3.4 L’inoculazione delle pian- te è stata ottenuta spruzzando Z+E-miyabenol C (Zmiyabenol C) nd nd 10.6 10.5 51.2 29.4 la sospensione di conidi sulla Z+E-ω-viniferin (E-ω-viniferin) nd nd 8.6 9.0 47.9 24.8 superficie inferiore di tutte le foglie completamente espan- α-viniferin nd nd 2.8 3.6 68.578.1 se in una camera climatica a E-cis-miyabenol C nd nd 3.9 3.4 49.4 46.9 24 ° C con 80% di umidità trans-pterostilbene relativa. (trans-resveratrol) nd nd 0.9 1.0 8.0 6.0 L’esperimento di infezione è stato eseguito in tre repli- F1 genotype 21/103 che. Le foglie di ogni replica trans-piceid nd nd nd nd 8.8 8.0 sono state raccolte a 0 ore, 2 giorni e 6 giorni dopo l’infe- trans-resveratrol nd nd nd nd 21.1 13.6 zione (dpi) con P. viticola. pallidol (ampelopsin H) nd nd nd nd 53.42 11.16 Tutte le foglie raccolte sono ampelopsin D+ state conservate a -20 °C quadrangularin A (1:1) nd nd nd nd 67.6 17.5 fino all’analisi. isohopeaphenol nd nd nd nd 1311.7 81.5 Reagenti chimici. ampelopsin H + vaticanol Acetonitrile, metanolo ed C isomer (ampelopsin H) nd nd nd nd 453.6 83.2 acido acetico per HPLC sono (+)-E-ε-viniferin nd nd nd nd 98.2 28.6 stati acquistati da Carlo Erba (Italia), acetato di etile da Z+E-miyabenol C (Zmiyabenol C) nd nd nd nd 121.3 26.4 BDH e acido fosforico da Z +E-ω-viniferin (E-ω-viniferin) nd nd nd nd 127.1 40.2 Merck. Il trans-resveratrolo è stato acquistato da Sigma, il α-viniferin nd nd nd nd 120.3 6.8 trans-4-hydroxystilbene da E-cis-miyabenol C nd nd nd nd 148.6 38.5 Aldrich, il cis-resveratrolo è trans-pterostilbene stato preparato dal trans- (trans-resveratrol) nd nd nd nd nd nd resveratrolo standard tramite fotoisomerizzazione (Mattivi Merzling et al., 1995), il trans-piceide trans-piceid nd nd nd nd 2.7 0.4 (trans-resveratrolo-3-O-β-D- glucopiranoside) è stato isola- trans-resveratrol nd nd nd nd 5.7 3.6 to dalle radici di Polygonum pallidol (ampelopsin H) nd nd nd nd 30.22 16.04 cuspidatum.
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