Flavonol Glycosides in Currant Leaves and Variation with Growth Season, Growth Location, and Leaf Position

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 42, 2015, Pages 9269-9276

  Yang, Wei ^a   Alanne, Aino Liisa ^a   Liu, Pengzhan ^a   Kallio, Heikki ^a   Yang, Baoru ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

1H and 13C NMR; flavonol glycosides; growth latitude; HPLC MS MS; leaves; Ribes nigrum; Ribes rubrum; seasonal variation

Indexed keywords

PHENOLS; PLANTS (BOTANY); SUGARS;

FLAVONOL GLYCOSIDES; HPLC-MS/MS; LEAVES; RIBES NIGRUM; RIBES RUBRUM; SEASONAL VARIATION;

FLAVONOIDS;

FLAVONOL DERIVATIVE; GLYCOSIDE; PLANT EXTRACT;

CHEMICAL STRUCTURE; CHEMISTRY; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PLANT LEAF; RIBES; SEASON; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOLS; GLYCOSIDES; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; RIBES; SEASONS; TANDEM MASS SPECTROMETRY;

EID: 84945944131     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b04171     Document Type: Article

References (37)

1. Geils, B. W.; Hummer, K. E.; Hunt, R. S. White pines, Ribes, and blister rust: a review and synthesis For. Pathol. 2010, 40, 147-185 10.1111/j.1439-0329.2010.00654.x
2. Hummer, K.; Dale, A. Horticulture of Ribes For. Pathol. 2010, 40, 251-263 10.1111/j.1439-0329.2010.00657.x
3. Määttä, K.; Kamal-Eldin, A.; Törrönen, R. Phenolic compounds in berries of black, red, green, and white currants (Ribes sp.) Antioxid. Redox Signaling 2001, 3, 981-993 10.1089/152308601317203521
4. Dai, J.; Mumper, R. J. Plant phenolics: extraction, analysis and their antioxidant and anticancer properties Molecules 2010, 15, 7313-7352 10.3390/molecules15107313
5. Gopalan, A.; Reuben, S. C.; Ahmed, S.; Darvesh, A. S.; Hohmann, J.; Bishayee, A. The health benefits of blackcurrants Food Funct. 2012, 3, 795-809 10.1039/c2fo30058c
6. Knekt, P.; Kumpulainen, J.; Järvinen, R.; Rissanen, H.; Heliövaara, M.; Reunanen, A.; Hakulinen, T.; Aromaa, A. Flavonoid intake and risk of chronic diseases Am. J. Clin. Nutr. 2002, 76, 560-568
7. McCullough, M. L.; Peterson, J. J.; Patel, R.; Jacques, P. F.; Shah, R.; Dwyer, J. T. Flavonoid intake and cardiovascular disease mortality in a prospective cohort of US adults Am. J. Clin. Nutr. 2012, 95, 454-464 10.3945/ajcn.111.016634
8. Wang, C.; Mehendale, S. R.; Calway, T.; Yuan, C. Botanical flavonoids on coronary heart disease Am. J. Chin. Med. 2011, 39, 661-671 10.1142/S0192415X1100910X
9. Cassidy, A.; Rimm, E. B.; O'Reilly, E. J.; Logroscino, G.; Kay, C.; Chiuve, S. E.; Rexrode, K. M. Dietary flavonoids and risk of stroke in women Stroke 2012, 43, 946-951 10.1161/STROKEAHA.111.637835
10. Knekt, P.; Järvinen, R.; Reunanen, A.; Maatela, J. Flavonoid intake and coronary mortality in Finland: a cohort study BMJ. 1996, 312, 478-481 10.1136/bmj.312.7029.478
11. Tabart, J.; Kevers, C.; Sipel, A.; Pincemail, J.; Defraigne, J.; Dommes, J. Optimisation of extraction of phenolics and antioxidants from black currant leaves and buds and of stability during storage Food Chem. 2007, 105, 1268-1275 10.1016/j.foodchem.2007.03.005
12. Declume, C. Anti-inflammatory evaluation op a hydroalcoholic extract op black currant leaves (Ribes nigrum) J. Ethnopharmacol. 1989, 27, 91-98 10.1016/0378-8741(89)90081-0
13. Tabart, J.; Franck, T.; Kevers, C.; Pincemail, J.; Serteyn, D.; Defraigne, J.; Dommes, J. Antioxidant and anti-inflammatory activities of Ribes nigrum extracts Food Chem. 2012, 131, 1116-1122 10.1016/j.foodchem.2011.09.076
14. Garbacki, N.; Kinet, M.; Nusgens, B.; Desmecht, D.; Damas, J. Proanthocyanidins, from Ribes nigrum leaves, reduce endothelial adhesion molecules ICAM-1 and VCAM-1 J. Inflammation 2005, 2, 9 10.1186/1476-9255-2-9
15. Tabart, J.; Kevers, C.; Pincemail, J.; Defraigne, J.; Dommes, J. Antioxidant capacity of black currant varies with organ, season, and cultivar J. Agric. Food Chem. 2006, 54, 6271-6276 10.1021/jf061112y
16. Liu, P.; Kallio, H.; Yang, B. Flavonol glycosides and other phenolic compounds in buds and leaves of different varieties of black currant (Ribes nigrum L.) and changes during growing season Food Chem. 2014, 160, 180-189 10.1016/j.foodchem.2014.03.056
17. Vagiri, M.; Ekholm, A.; Andersson, S. C.; Johansson, E.; Rumpunen, K. An optimized method for analysis of phenolic compounds in buds, leaves, and fruits of black currant (Ribes nigrum L.) J. Agric. Food Chem. 2012, 60, 10501-10510 10.1021/jf303398z
18. Haasbach, E.; Hartmayer, C.; Hettler, A.; Sarnecka, A.; Wulle, U.; Ehrhardt, C.; Ludwig, S.; Planz, O. Antiviral activity of Ladania067, an extract from wild black currant leaves against influenza A virus in vitro and in vivo. Front. Microbiol. 2014, 5, 10.3389/fmicb.2014.00171
19. Middleton, E.; Kandaswami, C.; Theoharides, T. C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 2000, 52, 673-751
20. Moon, J.; Tsushida, T.; Nakahara, K.; Terao, J. Identification of quercetin 3-O-β- d -glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin Free Radical Biol. Med. 2001, 30, 1274-1285 10.1016/S0891-5849(01)00522-6
21. Cyboran, S.; Bonarska-Kujawa, D.; Pruchnik, H.; Żylka, R.; Oszmiański, J.; Kleszczyńska, H. Phenolic content and biological activity of extracts of blackcurrant fruit and leaves Food Res. Int. 2014, 65, 47-58 10.1016/j.foodres.2014.05.037
22. Vagiri, M.; Conner, S.; Stewart, D.; Andersson, S. C.; Verrall, S.; Johansson, E.; Rumpunen, K. Phenolic compounds in blackcurrant (Ribes nigrum L.) leaves relative to leaf position and harvest date Food Chem. 2015, 172, 135-142 10.1016/j.foodchem.2014.09.041
23. Nour, V.; Trandafir, I.; Cosmulescu, S. Antioxidant capacity, phenolic compounds and minerals content of blackcurrant (Ribes nigrum L.) leaves as influenced by harvesting date and extraction method Ind. Crops Prod. 2014, 53, 133-139 10.1016/j.indcrop.2013.12.022
24. Oszmiański, J.; Wojdylo, A.; Gorzelany, J.; Kapusta, I. Identification and characterization of low molecular weight polyphenols in berry leaf extracts by HPLC-DAD and LC-ESI/MS J. Agric. Food Chem. 2011, 59, 12830-12835 10.1021/jf203052j
25. Schwarz, B.; Hofmann, T. Sensory-guided decomposition of red currant juice (Ribes rubrum) and structure determination of key astringent compounds J. Agric. Food Chem. 2007, 55, 1394-1404 10.1021/jf0629078
26. Price, K.; Colquhoun, I.; Barnes, K.; Rhodes, M. Composition and content of flavonol glycosides in green beans and their fate during processing J. Agric. Food Chem. 1998, 46, 4898-4903 10.1021/jf980687v
27. Kazuma, K.; Noda, N.; Suzuki, M. Malonylated flavonol glycosides from the petals of Clitoria ternatea Phytochemistry 2003, 62, 229-237 10.1016/S0031-9422(02)00486-7
28. Katsube, T.; Imawaka, N.; Kawano, Y.; Yamazaki, Y.; Shiwaku, K.; Yamane, Y. Antioxidant flavonol glycosides in mulberry (Morus alba L.) leaves isolated based on LDL antioxidant activity Food Chem. 2006, 97, 25-31 10.1016/j.foodchem.2005.03.019
29. Katsube, T.; Yamasaki, M.; Shiwaku, K.; Ishijima, T.; Matsumoto, I.; Abe, K.; Yamasaki, Y. Effect of flavonol glycoside in mulberry (Morus alba L.) leaf on glucose metabolism and oxidative stress in liver in diet-induced obese mice J. Sci. Food Agric. 2010, 90, 2386-2392 10.1002/jsfa.4096
30. Enkhmaa, B.; Shiwaku, K.; Katsube, T.; Kitajima, K.; Anuurad, E.; Yamasaki, M.; Yamane, Y. Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice J. Nutr. 2005, 135, 729-734
31. Németh, K.; Plumb, G. W.; Berrin, J.; Juge, N.; Jacob, R.; Naim, H. Y.; Williamson, G.; Swallow, D. M.; Kroon, P. A. Deglycosylation by small intestinal epithelial cell β-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans Eur. J. Nutr. 2003, 42, 29-42 10.1007/s00394-003-0397-3
32. Yerramsetty, V.; Gallaher, D. D.; Ismail, B. Malonylglucoside conjugates of isoflavones are much less bioavailable compared with unconjugated beta-glucosidic forms in rats J. Nutr. 2014, 144, 631-637 10.3945/jn.114.190801
33. Wang, S. Y.; Lin, H. Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage J. Agric. Food Chem. 2000, 48, 140-146 10.1021/jf9908345
34. Martz, F.; Jaakola, L.; Julkunen-Tiitto, R.; Stark, S. Phenolic composition and antioxidant capacity of bilberry (Vaccinium myrtillus) leaves in Northern Europe following foliar development and along environmental gradients J. Chem. Ecol. 2010, 36, 1017-1028 10.1007/s10886-010-9836-9
35. Jaakola, L.; Määttä-Riihinen, K.; Kärenlampi, S.; Hohtola, A. Activation of flavonoid biosynthesis by solar radiation in bilberry (Vaccinium myrtillus L.) leaves Planta 2004, 218, 721-728 10.1007/s00425-003-1161-x
36. Zheng, J.; Yang, B.; Ruusunen, V.; Laaksonen, O.; Tahvonen, R.; Hellsten, J.; Kallio, H. Compositional differences of phenolic compounds between black currant (Ribes nigrum L.) cultivars and their response to latitude and weather conditions J. Agric. Food Chem. 2012, 60, 6581-6593 10.1021/jf3012739
37. Cockell, C. S.; Southern, A.; Herrera, A. Lack of UV radiation in Biosphere 2-practical and theoretical effects on plants Ecol. Eng. 2000, 16, 293-299 10.1016/S0925-8574(99)00057-9