Oligomeric proanthocyanidines from Hedysarum theinum roots that were cleaved by benzylmercaptan were shown to be heterogeneous mixtures consisting of prodelphinine and procyanidine structural units with the former dominating. Fractionation of oligomeric proanthocyanidines on polyamide and MCI gel CHP20P sorbent isolated fractions containing primarily mixtures of di- and trimeric, tri- and tetrameric, or tetra- and pentameric proanthocyanidines. Analysis by mass spectrometry (MALDI-TOF) showed that fractions of trimers and tetramers contained more proanthocyanidines with a single A-type bond than fractions of dimers and trimers.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
I. V. Nechepurenko, M. P. Polovinka, N. I. Komarova, D. V. Korchagina, N. F. Salakhutdinov, and S. B. Nechepurenko, Khim. Prir. Soedin., 26 (2008).
O. V. Agafonova and S. B. Volodarskaya, Rastit. Resur., 36, No. 4, 47 (2000).
J. M. Ricardo da Silva, J. Rigaud, V. Cheynier, A. Cheminat, and M. Moutounet, Phytochemistry, 30, 1259 (1991).
Z. A. Kuliev, K. Kh. Kim, A. D. Vdovin, N. D. Abdullaev, Z. A. Khushbaktova, and V. N. Syrov, Khim. Prir. Soedin., 47 (2000).
R. S. Thompson, D. Jacques, E. Haslam, and R. J. N. Tanner, J. Chem. Soc., Perkin 1, 1387 (1972).
S. Matthews, I. Mila, A. Scalbert, B. Pollet, C. Lapierre, C. L. Herve du Penhoat, C. Rolando, and D. M. X. Donnelly, J. Agric. Food Chem., 45, 1195 (1997).
J. L. Torres and C. Lozano, Chromatographia, 54, 523 (2001).
A. C. Fletcher, L. J. Porter, E. Haslam, and R. K. Gupta, J. Chem. Soc., Perkin 1, 1628 (1977).
E. Haslam, in: The Flavonoids, J. B. Harborne, T. J. Mabry, and H. Mabry, eds., Chapman and Hall, London (1975), pp. 527–559.
P. Schofield, D. M. Mbugua, and A. N. Pell, Animal Feed Sci. Technol., 91, 21 (2001).
Y. Yang and M. Chien, J. Agric. Food Chem., 48, 3990 (2000).
E. L. Roux, T. Doco, P. Sarni-Manchado, Y. Lozano, and V. Cheynier, Phytochemistry, 48, 1251 (1998).
F. Hashimoto, G.-I. Nonaka, and I. Nishioka, Chem. Pharm. Bull., 37, 77 (1989).
F.-L. Hsu, G.-I. Nonaka, and I. Nishioka, Chem. Pharm. Bull., 33, 3293 (1985).
F. Geiss, M. Heinrich, D. Hunkler, and H. Rimpler, Phytochemistry, 39, 635 (1995).
J. M. Souquet, V. Cheynier, F. Brossaud, and M. Moutounet, Phytochemistry, 43, 509 (1996).
L. Y. Foo, Y. Lu, A. L. Molan, D. R. Woodfield, and W. C. McNabb, Phytochemistry, 54, 539 (2000).
H. Kolodziej, Phytochemistry, 29, 1671 (1990).
E. C. Bate-Smith, Phytochemistry, 14, 1107 (1975).
E. B. Walker, R. A. Mickelsen, and J. N. Mickelsen, U.S. Pat. No. 5,650,432 (1997); Chem. Abstr., 127, 117374 (1997).
L.-C. Lin, Y.-C. Kuo, and C.-J. Chou, J. Nat. Prod., 65, 505 (2002).
T. Bruyne, L. Pieters, M. Witvrouw, E. Clercq, D. V. Berghe, and A. J. Vlietinck, J. Nat. Prod., 62, 954 (1999); H.-Y. Cheng, C.-C. Lin, and T.-C. Lin, Antiviral Chem. Chemotherapy, 13, 223 (2002); Chem. Abstr., 139, 207137 (2003).
K. Taguchi, S. Taguchi, and K. Miyamoto, Jpn. Pat. No. 2003212783 (2003); Chem. Abstr., 139, 122707 (2003).
H. G. Preuss and D. Bagchi, U.S. Pat. No. 6,500,469 (2002); Chem. Abstr., 138, 49943 (2002).
G. I. Baram, M. A. Grachev, N. I. Komarova, M. P. Perelroyzen, Yu. A. Bolvanov, S. V. Kuzmin, V. V. Kargaltsev, and E. A. Kuper, J. Chromatogr., 264, 69 (1983).
J. G. Kirchner, Techniques of Chemistry, Vol. 14: Thin-Layer Chromatography, 2nd Ed., Wiley-Interscience, New York (1978).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 30–36, January–February, 2009.
Rights and permissions
About this article
Cite this article
Nechepurenko, I.V., Komarova, N.I., Gerasimova, Y.V. et al. Structure of oligomeric proanthocyanidines from Hedysarum thienum roots studied by thiolysis and MALDI-TOF MS. Chem Nat Compd 45, 32–39 (2009). https://doi.org/10.1007/s10600-009-9216-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-009-9216-2