Identification of two novel prodelphinidin A-type dimers from roasted hazelnut skins (Corylus avellana L.)

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 51, 2013, Pages 12640-12645

  Esatbeyoglu, Tuba ^a   Wray, Victor ^b   Winterhalter, Peter ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

1H and 13C NMR; A type proanthocyanidins; circular dichroism; hazelnut; phloroglucinolysis

Indexed keywords

ACID-CATALYZED DEGRADATION; COUNTERCURRENT CHROMATOGRAPHY; HAZELNUT; HPLC-ESI MS; PHLOROGLUCINOLYSIS; PREPARATIVE HPLC; PROANTHOCYANIDINS; ROASTED HAZELNUTS;

DICHROISM; FLAVONOIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CALCINATION;

ANTHOCYANIN; PLANT EXTRACT; PRODELPHINIDIN B 2 3' O GALLATE; PRODELPHINIDIN B-2 3'-O-GALLATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COUNTER CURRENT CHROMATOGRAPHY; DIMERIZATION; HAZELNUT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANT SEED;

ANTHOCYANINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CORYLUS; COUNTERCURRENT DISTRIBUTION; DIMERIZATION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLANT EXTRACTS; SEEDS;

EID: 84891462145     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404549w     Document Type: Article

References (46)

1. Prior, R. L.; Gu, L. Occurrence and biological significance of proanthocyanidins in the American diet Phytochemistry 2005, 66, 2264-2280
2. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Gebhardt, S.; Prior, R. L. Concentrations of proanthocyanidins in common foods and estimations of normal consumption J. Nutr. 2004, 134, 613-617
3. Porter, L. J. Flavans and proanthocyanidins. In The Flavonoids: Advances in Research since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, UK, 1994; pp 23-55.
4. Turkish Hazelnut Exporter's Union. The Turkish Hazelnut.; Turkish Hazelnut Exporter's Union: Giresun, Turkey, 2008.
5. Shahidi, F.; Alasalvar, C.; Liyana-Pathirana, C. M. Antioxidant phytochemicals in hazelnut kernel (Corylus avellana L.) and hazelnut byproducts J. Agric. Food Chem. 2007, 55, 1212-1220
6. Food and Agriculture Organization of the United Nations. FAO Statistical Yearbook 2012; http://faostat3.fao.org/home/index.html#DOWNLOAD (accessed May 28, 2013).
7. Del Rio, D.; Calani, L.; Dall'Asta, M.; Brighenti, F. Polyphenolic composition of hazelnut skin J. Agric. Food Chem. 2011, 59, 9935-9941
8. Pelvan, E.; Alasalvar, C.; Uzman, S. Effects of roasting on the antioxidant status and phenolic profiles of commercial Turkish hazelnut varieties (Corylus avellana L.) J. Agric. Food Chem. 2012, 60, 1218-1223
9. Schmitzer, V.; Slatnar, A.; Veberic, R.; Stampar, F.; Solar, A. Roasting affects phenolic composition and antioxidative activity of hazelnuts (Corylus avellana L.) J. Food Sci. 2011, 76, S14-S19
10. Monagas, M.; Garrido, I.; Lebrón-Aguilar, R.; Gómez- Cordovés, M. C.; Rybarczyk, A.; Amarowicz, R.; Bartolomé, B. Comparative flavan-3-ol profile and antioxidant capacity of roasted peanut, hazelnut, and almond skins J. Agric. Food Chem. 2009, 57, 10590-10599
11. Orem, A.; Balaban Yucesan, F.; Orem, C.; Akcan, B.; Vanizor Kural, B.; Alasalvar, C.; Shahidi, F. Hazelnut-enriched diet improves cardiovascular risk biomarkers beyond a lipid-lowering effect in hypercholesterolemic subjects J. Clin. Lipidol. 2013, 7, 123-131
12. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Prior, R. L. Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation J. Agric. Food Chem. 2003, 51, 7513-7521
13. Esatbeyoglu, T.; Winterhalter, P. Preparation of dimeric procyanidins B1, B2, B5, and B7 from a polymeric procyanidin fraction of black chokeberry (Aronia melanocarpa) J. Agric. Food Chem. 2010, 58, 5147-5153
14. 1H NMR spectroscopy J. Agric. Food Chem. 2011, 59, 62-69
15. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Zhang, Z.; Beecher, G.; Holden, J.; Haytowitz, D.; Prior, R. L. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods J. Mass Spectrom. 2003, 38, 1272-1280
16. Monagas, M.; Garrido, I.; Lebrón-Aguilar, R.; Bartolomé, B.; Gómez-Cordovés, C. Almond (Prunus dulcis (Mill.) D.A. Webb) skins as a potential source of bioactive polyphenols J. Agric. Food Chem. 2007, 55, 8498-8507
17. Li, H.-J.; Deinzer, M. L. The mass spectral analysis of isolated hops A-type proanthocyanidins by electrospray ionization tandem mass spectrometry J. Mass Spectrom. 2008, 43, 1353-1363
18. Barreiros, A. L. B. S.; David, J. P.; De Queiroz, L. P.; David, J. M. A-type proanthocyanidin antioxidant from Dioclea lasiophylla Phytochemistry (Elsevier) 2000, 55, 805-808
19. Jacques, D.; Haslam, E.; Bedford, G. R.; Greatbanks, D. Structure of the dimeric proanthocyanidin-A2 and its derivatives J. Chem. Soc., Chem. Commun. 1973, 518-520
20. Jacques, D.; Haslam, E.; Bedford, G. F.; Greatbanks, D. Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives J. Chem. Soc., Perkin Trans. 1 1974, 2663-2671
21. Vivas, N.; Glories, Y.; Pianet, I.; Barbe, B.; Laguerre, M. A complete structural and conformational investigation of procyanidin A2 dimer Tetrahedron Lett. 1996, 37, 2015-2018
22. Foo, L. Y.; Lu, Y.; Howell, A. B.; Vorsa, N. The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro Phytochemistry 2000, 54, 173-181
23. Thompson, R. S.; Jacques, D.; Haslam, E.; Tanner, R. J. N. Plant proanthocyanidins. I. Introduction: the isolation, structure, and distribution in nature of plant procyanidins J. Chem. Soc., Perkin Trans. 1 1972, 1387-1399
24. Fletcher, A. C.; Porter, L. J.; Haslam, E.; Gupta, R. K. Plant proanthocyanidins. Part 3. Conformational and configurational studies of natural procyanidins J. Chem. Soc., Perkin Trans. 1 1977, 1628-1637
25. 13C N.M.R. studies of procyanidins J. Chem. Soc., Perkin Trans. 1 1982, 1217-1221
26. Nonaka, G.-I.; Morimoto, S.; Kinjo, J.-E.; Nohara, T.; Nishioka, I. Tannins and related compounds L. Structures of proanthocyanidin A-1 and related compounds Chem. Pharm. Bull. 1987, 35, 149-155
27. Baldé, A. M.; Pieters, L. A.; Wray, V.; Kolodziej, H.; Vanden Berghe, D. A.; Claeys, M.; Vlietinck, A. J. Dimeric and trimeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis Phytochemistry (Elsevier) 1991, 30, 4129-4135
28. Baldé, A. M.; Pieters, L. A.; Gergely, A.; Kolodziej, H.; Claeys, M.; Vlietinck, A. J. A-type proanthocyanidins from stem-bark of Pavetta owariensis Phytochemistry (Elsevier) 1991, 30, 337-342
29. Baldé, A. M.; De Bruyne, T.; Pieters, L.; Kolodziej, H.; Vanden Berghe, D.; Claeys, M.; Vlietinck, A. Oligomeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis Phytochemistry (Elsevier) 1995, 38, 719-723
30. 13C NMR assignments of some green tea polyphenols Magn. Reson. Chem. 1996, 34, 887-890
31. Porter, L. J.; Ma, Z.; Chan, B. G. Cacao procyanidins: major flavanoids and identification of some minor metabolites Phytochemistry (Elsevier) 1991, 30, 1657-1663
32. Morimoto, S.; Nonaka, G.; Nishioka, I. Tannins and related compounds. LIX. Aesculitannins, novel proanthocyanidins with doubly-bonded structures from Aesculus hippocastanum L Chem. Pharm. Bull. 1987, 35, 4717-4729
33. Ma, C.; Nakamura, N.; Hattori, M.; Kakuda, H.; Qiao, J.; Yu, H. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia J. Nat. Prod. 2000, 63, 238-242
34. Kolodziej, H.; Sakar, M. K.; Burger, J. F. W.; Engelshowe, R.; Ferreira, D. A-Type proanthocyanidins from Prunus spinosa Phytochemistry (Elsevier) 1991, 30, 2041-2047
35. Lou, H.; Yamazaki, Y.; Sasaki, T.; Uchida, M.; Tanaka, H.; Oka, S. A-type proanthocyanidins from peanut skins Phytochemistry (Elsevier) 1999, 51, 297-308
36. Balas, L.; Vercauteren, J. Extensive high-resolution reverse 2D NMR analysis for the structural elucidation of procyanidin oligomers Magn. Reson. Chem. 1994, 32, 386-393
37. Le Roux, E.; Doco, T.; Sarni-Manchado, P.; Lozano, Y.; Cheynier, V. A-type proanthocyanidins from pericarp of Litchi chinensis Phytochemistry (Elsevier) 1998, 48, 1251-1258
38. Shoji, T.; Mutsuga, M.; Nakamura, T.; Kanda, T.; Akiyama, H.; Goda, Y. Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance J. Agric. Food Chem. 2003, 51, 3806-3813
39. Barrett, M. W.; Klyne, W.; Scopes, P. M.; Fletcher, A. C.; Porter, L. J.; Haslam, E. Plant proanthocyanidins. Part 6. Chiroptical studies. Part 95. Circular dichroism of procyanidins J. Chem. Soc., Perkin Trans. 1 1979, 2375-2377
40. Botha, J. J.; Young, D. A.; Ferreira, D.; Roux, D. G. Synthesis of condensed tannins. Part 1. Stereoselective and stereospecific syntheses of optically pure 4-arylflavan-3-ols, and assessment of their absolute stereochemistry at C-4 by means of circular dichroism J. Chem. Soc., Perkin Trans. 1 1981, 1213-1219
41. Van der Westhuizen, J. H.; Ferreira, D.; Roux, D. G. Synthesis of condensed tannins. Part 2. Synthesis by photolytic rearrangement, stereochemistry, and circular dichroism of the first 2,3- cis -3,4- cis -4-arylflavan-3-ols J. Chem. Soc., Perkin Trans. 1 1981, 1220-1226
42. Otsuka, H.; Fujioka, S.; Komiya, T.; Mizuta, E.; Takamoto, M. Studies on anti-inflammatory agents. VI. Anti-inflammatory constituents of Cinnamomum sieboldii Meissn Yakugaku Zasshi 1982, 102, 162-172
43. Van Rooyen, P. H.; Redelinghuys, H. J. P. Crystal structure and molecular conformation of proanthocyanidin-A2, a bitter substance in litchis (Litchi chinensis Sonn.) S. Afr. J. Chem. 1983, 36, 49-53
44. Koerner, J. L.; Hsu, V. L.; Lee, J.; Kennedy, J. A. Determination of proanthocyanidin A2 content in phenolic polymer isolates by reversed-phase high-performance liquid chromatography J. Chromatogr., A 2009, 1216, 1403-1409
45. Zang, X.; Shang, M.; Xu, F.; Liang, J.; Wang, X.; Mikage, M.; Cai, S. A-Type proanthocyanidins from the stems of Ephedra sinica (Ephedraceae) and their antimicrobial activities Molecules 2013, 18, 5172-5189
46. Esatbeyoglu, T. Analyse wertgebender Inhaltsstoffe von Aronia melanocarpa sowie Charakterisierung und Isolierung von Proanthocyanidinen. Cuvillier Verlag: Göttingen, Germany, 2011, (Ph.D. thesis, in German).