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Gli Oligomeri Del Resveratrolo Nelle Foglie Delle Viti Resistenti (Merzling X Teroldego) Infettate Da P

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Gli Oligomeri Del Resveratrolo Nelle Foglie Delle Viti Resistenti (Merzling X Teroldego) Infettate Da P L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 DOCUMENTO TECNICO 1Fulvio Mattivi 1Urska Vrhovsek 1Giulia Malacarne 1Domenico Masuero 1Luca Zulini 1Marco Stefanini 1Claudio Moser 1Riccardo Velasco 2Graziano Guella 1Fondazione Edmund Mach, Centro Ricerca ed Innovazione - San Michele all’Adige (TN) 2Laboratorio di Chimica Bio-orga- nica, Dipartimento di Fisica, Università di Trento F. Mattivi GLI OLIGOMERI DEL RESVERATROLO NELLE FOGLIE DELLE VITI RESISTENTI (MERZLING X TEROLDEGO) INFETTATE DA P. VITICOLA Scopo di questo studio era la caratterizzazione strutturale delle viniferine che si accumulano nelle foglie dei genotipi resistenti di Vitis vinifera se infettati con Plasmopara viticola. Sono state evidenziate 15 viniferine, delle quali 10 nuove per la vite, assieme ad un dimero che deriva dalla condensazione della (+)-catechina con lʼacido trans-caffeico. Introduzione merizzazione ossidativa, sono gli stilbeni maggiormen- denominate viniferine (2). te tossici verso la mobilità e All’interno delle Vitaceae, Alcune di queste sono state sviluppo dell’oomycete P. le viniferine rappresentano un dimostrare agire biologica- viticola (2,5). gruppo relativamente ristretto mente contro diversi patogeni Gli studi pioneristici di di composti fenolici di basso fungini della vite (3-4). È Langcake e Pryce (3) hanno peso molecolare costituito da stato osservato che la tossicità chiarito le strutture di trans- derivati del trans-resveratrolo delle fitoalessine stilbeniche resveratrolo, α-viniferin ed ε- dotati di proprietà antifungi- verso i funghi è strettamente viniferin, osservando la pre- ne, che permettono alla pianta correlata alla loro struttura senza di altri composti carat- di contrastare l’attacco dei chimica. In particolare, è stato teristici della famiglia delle Parole chiave: Vitis vinifera, patogeni (1). Nella vite, la riportato che γ-viniferin, Vitaceae simili alle viniferine Plasmopara viticola, stilbe- produzione di resveratrolo dimero ossidativo del resvera- ma non caratterizzati (β-vini- ni, stilbenoidi, NMR, spet- porta alla formazione di fitoa- trolo, e pterostilbene, analogo ferin e γ-viniferin). Hanno trometria di massa lessine che derivano da oligo- metilato del resveratrolo, descritto inoltre la formazione 71 L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 Tab. 1 - Nome, quantità isolata e dati MS dei composti ottenuti da foglie di vite infettate con P. viticola. frazione tempo quantità taglia nome formula MM ione molecolareosservato Δ massa ritenz. (min) (mg) molecolare calcolata (M-H)- (M-H)- (ppm) 1.1 17,4 0,13 di- Z-ε-viniferin (1) C28H22O6 454,1416 453,1337 453,1340 -0,7 1.2 17,9 2,80 di- E-ε-viniferin (2) C28H22O6 454,1416 453,1337 453,1323 3,1 1.4 18,5 n.a. di- E-ω-viniferin (3) C28H22O6 454,1416 453,1337 453,1340 -0,7 1.4 18,5 n.a. di- Z-ω-viniferin (4) C28H22O6 454,1416 453,1337 453,1338 -0,2 2.1 13,5 1,10 di- caffeic acid and C24H20O9 452,1107 451,1028 451,1021 1,6 catechin condensation product (5) 2.2 14,8 1,39 di- pallidol (6) C28H22O6 454,1416 453,1337 453,1317 4,4 3.1 15,4 0,61 tri- ampelopsin D (7) C28H22O6 454,1416 453,1337 453,1340 -0,7 + quadrangularin A (8) 3.2 18,9 1,13 tri- α-viniferin (9) C42H30O9 678,1890 677,1811 677,1818 -1,0 4.1 19,1 0,59 tri- E-cis-miyabenol C (10) C42H32O9 680,2046 679,1967 679,1979 -1,8 5.1 17,9 0,54 tri- Z-miyabenol C (11) C42H32O9 680,2046 679,1967 679,1974 -1,0 5.2 18,1 1,55 tri- E-miyabenol C (12) C42H32O9 680,2046 679,1967 679,1969 -0,3 6.1 16,8 5,46 tetra- isohopeaphenol (13) C56H42O12 906,2676 905,2597 905,2617 -2,2 7.1 17,5 1,04 tetra- ampelopsin H (14) C56H42O12 906,2676 905,2597 905,2620 -2,5 7.2 17,5 0,90 tetra- vaticanol C-like (15) C56H42O12 906,2676 905,2597 905,2635 -4,2 di un deidrodimero di trans- una più ampia ricerca finaliz- to (UV), dicroismo circolare Pinot Grigio. La muffa bianca resveratrolo (che successiva- zata a stabilire il ruolo dell’in- (CD) e proprietà ottiche, è emergente dalla parte inferio- mente ha preso il nome di δ- tera classe delle viniferine stato possibile identificare le re delle foglie è stata spazzo- viniferin) ad opera della nella difesa della vite nei con- dieci principali viniferine, lata in acqua bidistillata fino perossidasi da rafano e della fronti di P. viticola. Uno come pure tre viniferine ad ottenere una sospensione di 4 5 H2O2. Successivamente a que- screening preliminare condot- minori e un polifenolo dimero conidi con 10 /10 spore/mL. sti lavori c’è stato poco pro- to per mezzo di HPLC-DAD- presenti nelle foglie infettate. L’infezione delle piante è gresso nella caratterizzazione MS aveva mostrato che il Calcoli di meccanica moleco- stata ottenuta spruzzando la strutturale di questi composti 17% dei genotipi in una lare (MM) sono inoltre stati sospensione di conidi fredda bioattivi inducibili nelle foglie popolazione segregante condotti su tutti i composti sulla superficie inferiore di di vite. Altri stilbeni identifi- (Merzling x Vitis vinifera qui riportati, per individuarne tutte le foglie completamente cati in foglie infettate con P. Teroldego) presenta nelle la conformazione più stabile. estese, in una camera climati- viticola sono il monomero foglie una quantità elevata ca mantenuta a 24 °C e 80% pterostilbene (2) ed il dimero rispetto ai parentali, ed un RH. δ-viniferin (sinonimo: trans- complesso profilo di viniferi- Materiali resveratrol dehydrodimer), ne della vite note ed ignote, e metodi Composti chimici. Aceto- che sono stati descritti essere successivamente alla infezio- nitrile, metanolo e acido ace- le principali viniferine sinte- ne con P. viticola. Viti. Per l’isolamento delle tico sono stati acquistati da tizzate in foglie di V. vinifera viniferine sono stati scelti 18 Carlo Erba, etile acetato da var. Chasselas infettate da P. genotipi dai vigneti sperimen- BDH ed acido fosforico da viticola o soggette a radiazio- Scopo tali della Fondazione Edmund Merck. L’acqua era di grado ne ultravioletta (5), mentre lo del lavoro Mach in San Michele all’Adi- milliQ. I composti trans- stilbenoide α-viniferin non è ge, da una popolazione F1 resveratrolo e trans-4-hydro- più stato osservato nei lavori Lo scopo principale di que- che deriva da incrocio tra xystilbene sono stati ottenuti seguenti. La maggior parte sto studio era quindi l’isola- Merzling e V. vinifera cv da Sigma Aldrich, cis-resve- degli studi disponibili si sono mento e caratterizzazione Teroldego. Le 10 foglie api- ratrolo è stato preparato via focalizzati su presenza e ruolo strutturale delle viniferine cali di 2-3 germogli sono foto-isomerizzazione di stan- funzionale delle strutture note, presenti in alcuni genotipi state infettate con P. viticola, dard di trans-resveratrolo, concentrandosi soprattutto selezionati della popolazione e dopo 6 giorni campionate, mentre trans-piceid (trans- sugli oligomeri che manten- di viti resistente alla P. vitico- congelate e conservate a -20 resveratrol-3-O-β-D-glucopy- gono nella struttura il doppio la. Attraverso tecniche avan- °C. ranoside) era stato isolato legame stilbenico, denominati zate di spettrometria di massa dalle radici anidre di Poly- oligostilbeni (1,6) piuttosto (LC-ESI-MS e LC-ESI-Q- Infezione delle piante. gonum cuspidatum (7). La che su quei composti che la TOF) e misure estensive di Sporangiospore di P. viticola purezza di ogni monomero è hanno persa nella polimeriz- risonanza magnetica nucleare (Berk. e Curt) Berl. et De stata controllata per HPLC e zazione, detti stilbenoidi. (NMR) mono e bidimensio- Toni sono state raccolte da l’identità confermata in ac- Questo articolo è parte di nali, spettrometria ultraviolet- piante infette di V. vinifera cv cordo con Mattivi et al. (8). 72 L’ENOLOGO ❏ LUGLIO/AGOSTO 2013 Estrazione. Il processo è Fig. 1 - Purificazione dell’estratto grezzo sulla colonna diolo stato condotto sotto azoto, al buio e in assenza di acidi minerali, per prevenire la pro- duzione di artefatti dovuto ad ossidazione, foto-isomerizza- zione ed idrolisi. Le foglie sono state pesate (517 g), macinate ed estratte per 48 h a temperatura ambiente in metanolo (10 L). Il materiale solido è stato rimosso ed il volume di estratto ridotto a 500 mL in evaporatore rotan- te a 35 °C. Cromatografia preparati- va. Sia la cromatografia flash in bassa pressione che la cro- matografia liquida ad altra pressione sono state realizzate con un sistema HPLC prepa- rativo Shimadzu SCL-10 AVP. Per guidare l’estrazio- ne, sia l’estratto grezzo che ogni frazione intermedia sono state analizzate per HPLC- DAD-MS. Cromatografia flash su per HPLC-DAD-MS. La fra- tate a secco e sciolte in 100 così ottenute sono state porta- Isolute ENV+. Il primo pas- zione C, con tutti i composti mL di metanolo. Questa fra- te a 1.5 mL in acetone per la saggio nella purificazione di nostro interesse, veniva zione purificata risultava ulte- caratterizzazione preliminare dell’estratto è stato condotto selezionata per ulteriore lavo- riormente arricchita nei com- con NMR. con una colonna a siringa razione, mente le altre veni- posti desiderati. Isolute da 150 mL per croma- vano eliminate. Cromatografia preparati- tografia flash, impaccata con Cromatografia preparati- va in fase inversa. Una 20 g di assorbente ENV+ Cromatografia flash su va in fase normale. Per il colonna Discovery HS-C18, Isolute con diametro di 40-70 HW40S. Una seconda purifi- frazionamento dei diversi oli- 250 x 21.2 mm, 5 μm, veniva μm e dimensione media dei cazione è stata condotta sulla gomeri è stata scelta una condizionata con acqua, con pori di 60 μm, chiuso alle due stessa apparecchiatura, usan- colonna diolo, Develosil flusso 10 mL/min e collegata estremità con i dischi acces- do 20 g di resina HW40S 100DIOL-5, 300 x 20 mm.
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