Resveratrol and piceid isomers concentrations in grapevine shoots, leaves, and tendrils

https://doi.org/10.17221/258/2014-HORTSCICitation:Lachman J., Kotíková Z., Hejtmánková A., Pivec V., Pšeničnaja O., Šulc M., Střalková R., Dědina M. (2016): Resveratrol and piceid isomers concentrations in grapevine shoots, leaves, and tendrils. Hort. Sci. (Prague), 43: 25-32.
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The objective of this study was to evaluate the levels of cis- and trans-isomers of resveratrol and piceid contained in the shoots, leaves and tendrils of six grapevine varieties and three locations processed under two different drying conditions. The highest trans-resveratrol content was found in the shoots; trans-piceid was contained in lesser amounts (7%) and cis-forms only in very small amounts (~1%). In leaves, both forms of piceid were dominant, while in tendrils trans- and cis-forms of piceid were dominant in samples dried in the laboratory oven at 40°C. Pinot Noir differed from other varieties with a high trans-resveratrol amount. Growing location affected trans-resveratrol levels. Our results suggest that the trimmed clippings might be used as a valuable and inexpensive source of stilbenes. Clippings preserved by drying might be further processed to nutraceuticals or as an additive to the feed.
References:
Aaviksaar A., Haga M., Pussa T., Roasto M., Tsoupras G. (2003): Purification of resveratrol from vine stems. Proceedings of the Estonian Academy of Sciences, Chemistry, 52: 155–164.
 
Adrian M., Jeandet P., Bessis R., Joubert J. M. (1996): Induction of Phytoalexin (Resveratrol) Synthesis in Grapevine Leaves Treated with Aluminum Chloride (AlCl 3 ). Journal of Agricultural and Food Chemistry, 44, 1979-1981  https://doi.org/10.1021/jf950807o
 
Aggarwal B.B., Bhardway A., Aggarwa R.S., Seeram N.P., Shishodia S., Takada Y. (2004): Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Research, 24: 2783–2840.
 
Alonso Ángeles M., Guillén Dominico A., Barroso Carmelo G., Puertas Belén, García Alberto (2002): Determination of Antioxidant Activity of Wine Byproducts and Its Correlation with Polyphenolic Content. Journal of Agricultural and Food Chemistry, 50, 5832-5836  https://doi.org/10.1021/jf025683b
 
Anastasiadi Maria, Pratsinis Harris, Kletsas Dimitris, Skaltsounis Alexios-Leandros, Haroutounian Serkos A. (2012): Grape stem extracts: Polyphenolic content and assessment of their in vitro antioxidant properties. LWT - Food Science and Technology, 48, 316-322  https://doi.org/10.1016/j.lwt.2012.04.006
 
Barros A., Gironés-Vilaplana A., Teixeira A., Collado-González J., Moreno D.A., Gilo-Izquiredo A., Rosa E., Domínguez-Perles R. (2014): Evaluation of grape (Vitis vinifera L.) stems from Portuguese varieties as a source of (poly)phenolic compounds: A comparative study. In: Abstracts Book of 8th ISANH Congress on Polyphenols Applications, ISANH, Lisbon.
 
Bavaresco L., Mattivi F., De Rosso M., Flamini R. (2012): Effect of elicitors, viticultural factors, and enological practises on resveratrol and stilbenes in grapevine and wine. Medicinal Chemistry, 12: 1366–1381.
 
Çetin Emine Sema, Altinöz Duygu, Tarçan Ecehan, Göktürk Baydar Nilgün (2011): Chemical composition of grape canes. Industrial Crops and Products, 34, 994-998  https://doi.org/10.1016/j.indcrop.2011.03.004
 
Chong Julie, Poutaraud Anne, Hugueney Philippe (2009): Metabolism and roles of stilbenes in plants. Plant Science, 177, 143-155  https://doi.org/10.1016/j.plantsci.2009.05.012
 
Doshi Pooja, Adsule Pandurang, Banerjee Kaushik (2006): Phenolic composition and antioxidant activity in grapevine parts and berries (Vitis vinifera L.) cv. Kishmish Chornyi (Sharad Seedless) during maturation. International Journal of Food Science and Technology, 41, 1-9  https://doi.org/10.1111/j.1365-2621.2006.01214.x
 
Fernández-Mar M.I., Mateos R., García-Parrilla M.C., Puertas B., Cantos-Villar E. (2012): Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review. Food Chemistry, 130, 797-813  https://doi.org/10.1016/j.foodchem.2011.08.023
 
Garrido Jorge, Borges Fernanda (2013): Wine and grape polyphenols — A chemical perspective. Food Research International, 54, 1844-1858  https://doi.org/10.1016/j.foodres.2013.08.002
 
González-Barrio Rocío, Beltrán David, Cantos Emma, Gil María I., Espín Juan Carlos, Tomás-Barberán Francisco A. (2006): Comparison of Ozone and UV-C Treatments on the Postharvest Stilbenoid Monomer, Dimer, and Trimer Induction in Var. ‘Superior' White Table Grapes. Journal of Agricultural and Food Chemistry, 54, 4222-4228  https://doi.org/10.1021/jf060160f
 
Gorena Tamara, Saez Vania, Mardones Claudia, Vergara Carola, Winterhalter Peter, von Baer Dietrich (2014): Influence of post-pruning storage on stilbenoid levels in Vitis vinifera L. canes. Food Chemistry, 155, 256-263  https://doi.org/10.1016/j.foodchem.2014.01.073
 
Ji Mei, Li Qiang, Ji Hua, Lou Hongxiang (2014): Investigation of the distribution and season regularity of resveratrol in Vitis amurensis via HPLC–DAD–MS/MS. Food Chemistry, 142, 61-65  https://doi.org/10.1016/j.foodchem.2013.06.131
 
Karacabey Erkan, Mazza Giuseppe (2008): Optimization of Solid−Liquid Extraction of Resveratrol and Other Phenolic Compounds from Milled Grape Canes ( Vitis vinifera ). Journal of Agricultural and Food Chemistry, 56, 6318-6325  https://doi.org/10.1021/jf800687b
 
Kumšta M., Pavloušek P., Kupsa J. (2012): Influence of terroir on the concentration of selected stilbenes in wines of the cv. Riesling in the Czech Republic. Horticultural Science, 39: 38–46.
 
Lachman J., Šulc M., Hejtmánková A., Pivec V., Orsák M. (2004): Content of polyphenolic antioxidants and trans-resveratrol in grapes of different varieties of grapevine (Vitis vinifera L.). Horticultural Science, 31: 63–69.
 
Li Huige, Xia Ning, Förstermann Ulrich (2012): Cardiovascular effects and molecular targets of resveratrol. Nitric Oxide, 26, 102-110  https://doi.org/10.1016/j.niox.2011.12.006
 
Liu Wen, Liu Chunyan, Yang Chunxiang, Wang Lijun, Li Shaohua (2010): Effect of grape genotype and tissue type on callus growth and production of resveratrols and their piceids after UV-C irradiation. Food Chemistry, 122, 475-481  https://doi.org/10.1016/j.foodchem.2010.03.055
 
Liu Chunyan, Wang Lijun, Wang Junfang, Wu Benhong, Liu Wen, Fan Peige, Liang Zhenchang, Li Shaohua (2013): Resveratrols in Vitis berry skins and leaves: Their extraction and analysis by HPLC. Food Chemistry, 136, 643-649  https://doi.org/10.1016/j.foodchem.2012.08.017
 
Melzoch K., Hanzlíková I., Filip V., Buckiová D., Šmidrkal J. (2001): Resveratrol in parts of vine and wine originationg from Bohemian and Moravian vineyard regions. Agriculturae Conspectus Scientificus, 66: 53–57.
 
Püssa Tõnu, Floren Janar, Kuldkepp Paul, Raal Ain (2006): Survey of Grapevine Vitis vinifera Stem Polyphenols by Liquid Chromatography−Diode Array Detection−Tandem Mass Spectrometry. Journal of Agricultural and Food Chemistry, 54, 7488-7494  https://doi.org/10.1021/jf061155e
 
Rayne Sierra, Karacabey Erkan, Mazza G. (2008): Grape cane waste as a source of trans-resveratrol and trans-viniferin: High-value phytochemicals with medicinal and anti-phytopathogenic applications. Industrial Crops and Products, 27, 335-340  https://doi.org/10.1016/j.indcrop.2007.11.009
 
Schoedl Katharina, Schuhmacher Rainer, Forneck Astrid (2012): Studying the polyphenols of grapevine leaves according to age and insertion level under controlled conditions. Scientia Horticulturae, 141, 37-41  https://doi.org/10.1016/j.scienta.2012.04.014
 
Vergara Carola, von Baer Dietrich, Mardones Claudia, Wilkens Andrea, Wernekinck Katerina, Damm Anika, Macke Sebastian, Gorena Tamara, Winterhalter Peter (2012): Stilbene Levels in Grape Cane of Different Cultivars in Southern Chile: Determination by HPLC-DAD-MS/MS Method. Journal of Agricultural and Food Chemistry, 60, 929-933  https://doi.org/10.1021/jf204482c
 
Wang Wei, Tang Ke, Yang Hao-Ru, Wen Peng-Fei, Zhang Ping, Wang Hui-Ling, Huang Wei-Dong (2010): Distribution of resveratrol and stilbene synthase in young grape plants (Vitis vinifera L. cv. Cabernet Sauvignon) and the effect of UV-C on its accumulation. Plant Physiology and Biochemistry, 48, 142-152  https://doi.org/10.1016/j.plaphy.2009.12.002
 
Zhang Ang, Fang Yulin, Li Xuan, Meng Jiangfei, Wang Hua, Li Hua, Zhang Zhenwen, Guo Zhijun (2011): Occurrence and Estimation of trans-Resveratrol in One-Year-Old Canes from Seven Major Chinese Grape Producing Regions. Molecules, 16, 2846-2861  https://doi.org/10.3390/molecules16042846
 
Aaviksaar A., Haga M., Pussa T., Roasto M., Tsoupras G. (2003): Purification of resveratrol from vine stems. Proceedings of the Estonian Academy of Sciences, Chemistry, 52: 155–164.
 
Adrian M., Jeandet P., Bessis R., Joubert J. M. (1996): Induction of Phytoalexin (Resveratrol) Synthesis in Grapevine Leaves Treated with Aluminum Chloride (AlCl 3 ). Journal of Agricultural and Food Chemistry, 44, 1979-1981  https://doi.org/10.1021/jf950807o
 
Aggarwal B.B., Bhardway A., Aggarwa R.S., Seeram N.P., Shishodia S., Takada Y. (2004): Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. Anticancer Research, 24: 2783–2840.
 
Alonso Ángeles M., Guillén Dominico A., Barroso Carmelo G., Puertas Belén, García Alberto (2002): Determination of Antioxidant Activity of Wine Byproducts and Its Correlation with Polyphenolic Content. Journal of Agricultural and Food Chemistry, 50, 5832-5836  https://doi.org/10.1021/jf025683b
 
Anastasiadi Maria, Pratsinis Harris, Kletsas Dimitris, Skaltsounis Alexios-Leandros, Haroutounian Serkos A. (2012): Grape stem extracts: Polyphenolic content and assessment of their in vitro antioxidant properties. LWT - Food Science and Technology, 48, 316-322  https://doi.org/10.1016/j.lwt.2012.04.006
 
Barros A., Gironés-Vilaplana A., Teixeira A., Collado-González J., Moreno D.A., Gilo-Izquiredo A., Rosa E., Domínguez-Perles R. (2014): Evaluation of grape (Vitis vinifera L.) stems from Portuguese varieties as a source of (poly)phenolic compounds: A comparative study. In: Abstracts Book of 8th ISANH Congress on Polyphenols Applications, ISANH, Lisbon.
 
Bavaresco L., Mattivi F., De Rosso M., Flamini R. (2012): Effect of elicitors, viticultural factors, and enological practises on resveratrol and stilbenes in grapevine and wine. Medicinal Chemistry, 12: 1366–1381.
 
Çetin Emine Sema, Altinöz Duygu, Tarçan Ecehan, Göktürk Baydar Nilgün (2011): Chemical composition of grape canes. Industrial Crops and Products, 34, 994-998  https://doi.org/10.1016/j.indcrop.2011.03.004
 
Chong Julie, Poutaraud Anne, Hugueney Philippe (2009): Metabolism and roles of stilbenes in plants. Plant Science, 177, 143-155  https://doi.org/10.1016/j.plantsci.2009.05.012
 
Doshi Pooja, Adsule Pandurang, Banerjee Kaushik (2006): Phenolic composition and antioxidant activity in grapevine parts and berries (Vitis vinifera L.) cv. Kishmish Chornyi (Sharad Seedless) during maturation. International Journal of Food Science and Technology, 41, 1-9  https://doi.org/10.1111/j.1365-2621.2006.01214.x
 
Fernández-Mar M.I., Mateos R., García-Parrilla M.C., Puertas B., Cantos-Villar E. (2012): Bioactive compounds in wine: Resveratrol, hydroxytyrosol and melatonin: A review. Food Chemistry, 130, 797-813  https://doi.org/10.1016/j.foodchem.2011.08.023
 
Garrido Jorge, Borges Fernanda (2013): Wine and grape polyphenols — A chemical perspective. Food Research International, 54, 1844-1858  https://doi.org/10.1016/j.foodres.2013.08.002
 
González-Barrio Rocío, Beltrán David, Cantos Emma, Gil María I., Espín Juan Carlos, Tomás-Barberán Francisco A. (2006): Comparison of Ozone and UV-C Treatments on the Postharvest Stilbenoid Monomer, Dimer, and Trimer Induction in Var. ‘Superior' White Table Grapes. Journal of Agricultural and Food Chemistry, 54, 4222-4228  https://doi.org/10.1021/jf060160f
 
Gorena Tamara, Saez Vania, Mardones Claudia, Vergara Carola, Winterhalter Peter, von Baer Dietrich (2014): Influence of post-pruning storage on stilbenoid levels in Vitis vinifera L. canes. Food Chemistry, 155, 256-263  https://doi.org/10.1016/j.foodchem.2014.01.073
 
Ji Mei, Li Qiang, Ji Hua, Lou Hongxiang (2014): Investigation of the distribution and season regularity of resveratrol in Vitis amurensis via HPLC–DAD–MS/MS. Food Chemistry, 142, 61-65  https://doi.org/10.1016/j.foodchem.2013.06.131
 
Karacabey Erkan, Mazza Giuseppe (2008): Optimization of Solid−Liquid Extraction of Resveratrol and Other Phenolic Compounds from Milled Grape Canes ( Vitis vinifera ). Journal of Agricultural and Food Chemistry, 56, 6318-6325  https://doi.org/10.1021/jf800687b
 
Kumšta M., Pavloušek P., Kupsa J. (2012): Influence of terroir on the concentration of selected stilbenes in wines of the cv. Riesling in the Czech Republic. Horticultural Science, 39: 38–46.
 
Lachman J., Šulc M., Hejtmánková A., Pivec V., Orsák M. (2004): Content of polyphenolic antioxidants and trans-resveratrol in grapes of different varieties of grapevine (Vitis vinifera L.). Horticultural Science, 31: 63–69.
 
Li Huige, Xia Ning, Förstermann Ulrich (2012): Cardiovascular effects and molecular targets of resveratrol. Nitric Oxide, 26, 102-110  https://doi.org/10.1016/j.niox.2011.12.006
 
Liu Wen, Liu Chunyan, Yang Chunxiang, Wang Lijun, Li Shaohua (2010): Effect of grape genotype and tissue type on callus growth and production of resveratrols and their piceids after UV-C irradiation. Food Chemistry, 122, 475-481  https://doi.org/10.1016/j.foodchem.2010.03.055
 
Liu Chunyan, Wang Lijun, Wang Junfang, Wu Benhong, Liu Wen, Fan Peige, Liang Zhenchang, Li Shaohua (2013): Resveratrols in Vitis berry skins and leaves: Their extraction and analysis by HPLC. Food Chemistry, 136, 643-649  https://doi.org/10.1016/j.foodchem.2012.08.017
 
Melzoch K., Hanzlíková I., Filip V., Buckiová D., Šmidrkal J. (2001): Resveratrol in parts of vine and wine originationg from Bohemian and Moravian vineyard regions. Agriculturae Conspectus Scientificus, 66: 53–57.
 
Püssa Tõnu, Floren Janar, Kuldkepp Paul, Raal Ain (2006): Survey of Grapevine Vitis vinifera Stem Polyphenols by Liquid Chromatography−Diode Array Detection−Tandem Mass Spectrometry. Journal of Agricultural and Food Chemistry, 54, 7488-7494  https://doi.org/10.1021/jf061155e
 
Rayne Sierra, Karacabey Erkan, Mazza G. (2008): Grape cane waste as a source of trans-resveratrol and trans-viniferin: High-value phytochemicals with medicinal and anti-phytopathogenic applications. Industrial Crops and Products, 27, 335-340  https://doi.org/10.1016/j.indcrop.2007.11.009
 
Schoedl Katharina, Schuhmacher Rainer, Forneck Astrid (2012): Studying the polyphenols of grapevine leaves according to age and insertion level under controlled conditions. Scientia Horticulturae, 141, 37-41  https://doi.org/10.1016/j.scienta.2012.04.014
 
Vergara Carola, von Baer Dietrich, Mardones Claudia, Wilkens Andrea, Wernekinck Katerina, Damm Anika, Macke Sebastian, Gorena Tamara, Winterhalter Peter (2012): Stilbene Levels in Grape Cane of Different Cultivars in Southern Chile: Determination by HPLC-DAD-MS/MS Method. Journal of Agricultural and Food Chemistry, 60, 929-933  https://doi.org/10.1021/jf204482c
 
Wang Wei, Tang Ke, Yang Hao-Ru, Wen Peng-Fei, Zhang Ping, Wang Hui-Ling, Huang Wei-Dong (2010): Distribution of resveratrol and stilbene synthase in young grape plants (Vitis vinifera L. cv. Cabernet Sauvignon) and the effect of UV-C on its accumulation. Plant Physiology and Biochemistry, 48, 142-152  https://doi.org/10.1016/j.plaphy.2009.12.002
 
Zhang Ang, Fang Yulin, Li Xuan, Meng Jiangfei, Wang Hua, Li Hua, Zhang Zhenwen, Guo Zhijun (2011): Occurrence and Estimation of trans-Resveratrol in One-Year-Old Canes from Seven Major Chinese Grape Producing Regions. Molecules, 16, 2846-2861  https://doi.org/10.3390/molecules16042846
 
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