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Stilbene Oligomer Phytoalexins in Grape As a Response to Aspergillus Carbonarius Infection

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Stilbene Oligomer Phytoalexins in Grape As a Response to Aspergillus Carbonarius Infection Physiological and Molecular Plant Pathology 93 (2016) 112e118 Contents lists available at ScienceDirect Physiological and Molecular Plant Pathology journal homepage: www.elsevier.com/locate/pmpp Stilbene oligomer phytoalexins in grape as a response to Aspergillus carbonarius infection * Riccardo Flamini a, , Alessandro Zanzotto a, Mirko de Rosso a, Gianluca Lucchetta a, Antonio Dalla Vedova a, Luigi Bavaresco b a Council for Agricultural Research and Economics e Viticulture and Oenology (CREA), Viale XXVIII Aprile 26, 31015 Conegliano (TV), Italy b Department of Sustainable Crop Production, Pomology and Viticulture Section, Universita Cattolica S.C., Via Emilia Parmense 84, 29122 Piacenza, Italy article info abstract Article history: Stilbenes are grapevine phytoalexins elicited by biotic and abiotic agents; Aspergillus carbonarius is a Received 29 September 2015 widespread ochratoxin A producing fungus present in warm conditions, such as in Southern Italy. To Received in revised form increase the knowledge on biosynthesis of stilbene oligomers induced by A. carbonarius infection, grape 20 January 2016 berries of the Southern Italian grape cv. Negro Amaro were inoculated. Significant increase of trans- Accepted 31 January 2016 resveratrol and resveratrol dimers and oligomers, such as caraphenol, E-ε-viniferin, u-viniferin, d-vin- Available online 4 February 2016 iferin, a-viniferin, E-miyabenol C, and two tetramers, was observed, and concomitant decrease of glycoside derivatives. These findings improve the knowledge on the phytoalexin production as response Keywords: Stilbene phytoalexins against this pathogen. © A. carbonarius 2016 Elsevier Ltd. All rights reserved. Negro Amaro V. vinifera grape In-vitro infection Time of flight mass spectrometry 1. Introduction demonstrated the anti-cancer, anti-oxidant, anti-inflammatory and cardio-protective proprieties of resveratrol, and its platelet aggre- A number of stilbene derivatives were identified in grapevine gation inhibition [14-19]; piceatannol blocks LMP2A, a viral organs and those produced in soft tissues act as phytoalexins under protein-tyrosine kinase implicated in leukemia, non-Hodgkin's the elicitation of biotic and/or abiotic agents through the activation lymphoma and other diseases associated with the EBV virus, and of stilbene synthase gene (STS) [1]. Several organisms, such as acts on human melanoma cells [20-22]. Transfer of these com- Botrytis cinerea [2-4], Plasmopara viticola [5], Erysiphe necator [6], pounds to the wines enhances the healthy proprieties of the esca disease fungi [7], Rhizopus stolonifer [8], Aspergillus sp. [9,10], products [1]. can induce the production of stilbene phytoalexins. E and Z isomers Two types of stilbene phytoalexins can be synthesized after a of ε-viniferin and u-viniferin, and resveratrol oligomers, such as biotic elicitation: “inducible” viniferins and oligomers, which arise ampelopsin D, quadrangularin A, a-viniferin, E and Z miyabenol C, from the trans-resveratrol oligomerization and are markers of isohopeaphenol, ampelopsin H, vaticanol C-like, were identified in active defense of the plant, and “metabolized” viniferins produced vine leaves, roots, clusters and stems [11], as well as E-ampelopsin by enzymes released from the pathogen attempting to eliminate E, eamurensin B, E-resveratroloside, E-3,5,40-trihydroxystilbene 2- toxic compounds [23]. C-glucoside, Z-ampelopsin E, scirpusin A, E and Z vitisin B in vine For example, formation of six oxidized resveratrol dimers (A-C canes [12]. restrytisols, d-viniferin, leachinol F and pallidol) after incubation of Principal stilbenes identified in grape are trans-resveratrol B. cinerea in the presence of resveratrol was observed, and the (3,5,4'-trihydroxystilbene), piceatannol (3,4,30,5'-tetrahydroxy- pathogenicity of different B. cinerea strains was directly correlated trans-stilbene), cis and trans piceid (resveratrol glucoside), and to their capacity to degrade the grape viniferins [24,25]. A scheme some resveratrol dimers (viniferins) [13]. Several in-vitro studies of formation of resveratrol trimers and tetramers is shown in Fig. 1. STS-gene expression in grapes after inoculation with Aspergillus carbonarius was studied Vezzulli and collaborators: as expected, higher gene expression and resveratrol synthesis was observed in a * Corresponding author. E-mail address: riccardo.fl[email protected] (R. Flamini). disease resistant variety (Castor) with respect to a susceptible http://dx.doi.org/10.1016/j.pmpp.2016.01.011 0885-5765/© 2016 Elsevier Ltd. All rights reserved. R. Flamini et al. / Physiological and Molecular Plant Pathology 93 (2016) 112e118 113 HO HO HO O OH HO HO HO O OH H H O HO H OH H H H OH OH H HO H H H OH H H HO H H H H OH HO H OH OH HO O OH OH OH OH HO OH OH 5 4 3 11 OH OH HO HO OH OH OH HO O OH HO H O H OH H H H O * H H H H * HO OH H O H H HO H H H H HO OH OH OH HO O HOHO OH OH HO O 6 1 2 10 HO OH HO OH HO HO O OH O H O OH H OH H H H OH H HO HO H HO H H H H H H H H H OH HO O HO O OH HO O OH HO OH HO OH HO 7 8 9 Fig. 1. Scheme of formation of viniferins and resveratrol oligomers in grape: (1) trans-resveratrol, (2) ε-viniferin (Eand Z)/u-viniferin, (3) pallidol, (4) caraphenol B, (5) d-viniferin (E and Z), (6) a-viniferin, (7) isohopeaphenol, (8) E-miyabenol C, (9) Z-miyabenol C, (10) vaticanol C isomer, (11) ampelopsin H. cultivar, like Barbera [10]. the basis of their isotopic pattern and by performing multiple mass A. carbonarius is a warm climate widespread species present in spectrometry (MS/MS) analysis, including several viniferins and Southern Italy vineyards due to the favorable climatic conditions some resveratrol trimers and tetramers (E and Z miyabenol C, [26]. Ability of many A. carbonarius strains to produce ochratoxin A hopheapenol, an ampelopsin H-like compound) [32]. In the present (OTA) was proven by various studies and it poses serious concerns work, the production of stilbenes in Negro Amaro grape berries because OTA is a IARC Group 2B carcinogen [27-29]. The biosyn- infected with A. carbonarius was studied by these methods, to thetic pathway of the toxin has not been clarified yet, even if a expand the knowledge on the phytoalexin production as defense polyketide synthase and - more recently e non ribosomal peptide against this pathogen and investigate possible diagnostic markers synthetase (NRPS) genes were reported in OTA production by of the infection. A. carbonarius [30]. Most of the studies about optimal conditions for A. carbonarius mycelial growth and OTA production were per- 2. Materials and methods formed in-vitro conditions. Other studies on the effects of Merlot and Barbera berry inoculation with A. carbonarius, considered the 2.1. Grape samples and A. carbonarius inoculation variation of trans-resveratrol, piceid, piceatannol, and ε-viniferins during the veraison [9,31]; no data on the production of other Grape berries of cv. Negro Amaro were collected in 2012 at resveratrol dimers and oligomers are so far available in the ripening (grape must parameters: Brix ¼ 17.1, total acidity ¼ 10.7, literature. pH ¼ 3.14) from the CREA-VIT Germplasm Collection (Susegana, Some studies showed that the extent of OTA contamination Treviso, Italy). depends on the grape variety: e.g., lower OTA contamination was Uninfected berries with intact cuticle were detached with the found in Malvasia Nera, Pampanuto, Uva di Troia and Negro Amaro pedicel, soaked in a 2% sodium hypochlorite solution (2 min) and grape berries artificially inoculated with A. carbonarius with respect rinsed twice with sterile distilled water (10e15 min in orbital to other varieties, such as Cabernet Sauvignon and Verdeca [27,29]. shaker). Inoculum was prepared by growing a OTA-producing Negro Amaro is a red grape variety cultivated in Southern Italy, strain of A. carbonarius (ITEM 7444, CNR-ISPA, Bari, Italy) on PDA especially in Apulia region, and is used to produce red and rose (Potato Dextrose Agar) plates, at 25 C for 7 days. After incubation, wines characterized by a good structure and fruity and spicy the plates were rinsed with 10 ml of a 0.02% Tween solution and the flavors. suspension was adjusted with sterile distilled water to obtain a Recently, analytical methods by ultra-high performance liquid final concentration of 106 conidia/ml, measured with a Thoma cell chromatography/quadrupole-time of flight mass spectrometry counting chamber. The study of i) damaged and uninfected berries (UHPLC/QTOF MS) were developed to study stilbenes in grape and and ii) damaged and infected berries, was performed. Berries with wine [32,33]. These modern analytical approaches allow identifi- pedicel were wounded under sterile conditions, puncturing the cation of many compounds including those whose standards are cuticle with a 0.5 mm needle. Grape berries with pedicel were not yet available. E.g., in Raboso Piave and Primitivo grapes ten inoculated by soaking in the conidial suspension on orbital shaker resveratrol derivatives from dimers to tetramers were identified on for 5 min. The berries were placed on a metal net, in an aluminum Download English Version: https://daneshyari.com/en/article/2836224 Download Persian Version: https://daneshyari.com/article/2836224 Daneshyari.com.
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