Summary
1. The PMR spectra of 13 natural stilbenes have been studied.
2. The dominating role of π-electron interaction of the fragments of the stilbene molecule in the screening of the aromatic and olefinic protons has been shown. A series of increments presenting interest for determining the structure of stilbene compounds is proposed.
3. It has been established that the nature and nature and number of the substituents in the aglycone part of the molecule have no influence on the screening of the anomeric proton of glycosidated stilbenes, but it does depend on the position of attachment of the carbohydrate fragment.
Similar content being viewed by others
Literature cited
J. W. Rowe, C. L. Bower, and E. R. Wagner, Phytochem.,8, 235 (1969).
G. E. Blair, J. M. Cassady, J. E. Robbers, E. Tyler, and R. F. Raffauf, Phytochem.,8, 497 (1969).
H. J. Ranks and D. W. Cameron, Australian J. Chem.,24, 2427 (1971).
S. E. Drewes, Phytochem.,10, 2837 (1971).
N. A. Tyukavkina, A. S. Gromova, V. I. Lutskii, and V. K. Voronov, Khim. Prirodn. Soedin., 600 (1972).
N. A. Tyukavkina, V. I. Lutskii, A. S. Gromova, and N. M. Borodina, in: Phenolic Compounds and Their Physiological Properties [in Russian], Alma-Ata (1973), p. 150.
A. S. Gromova, V. I. Lutskii, and N. A. Tyukavkina, Khim. Prirodn. Soedin., 778 (1974).
A. S. Gromova, N. A. Tyukavkina, V. I. Lutskii, G. A. Kalabin, and D. F. Kushnarev, Khim. Prirodn. Soedin., 677 (1975).
M. W. Dietrich, J. S. Nash, and R. E. Keller, Anal. Chem.,38, 1479 (1966).
T. J. Mabry, K. R. Markham, and M. B. Thomas, The Systematic Identification of Flavonoids, Springer-Verlag, New York (1970).
H. Gusten and M. Salzwedel, Tetrahedron,23, 173 (1967).
High-Resolution NMR Spectra Catalogue, Varian Associates,1, No. 305, 306 (1962).
T. A. Wittstruck and E. N. Trachtenberg, J. Am. Chem. Soc.,89, 3803 (1967).
B. Gurudata, J. B. Stothers, and J. D. Talman, Canad. J. Chem.,45, 731 (1967).
I. R. Ader and L. Phillips, J. Chem. Soc., Perkin II, 1975, 1979, 1988, (1972).
E. W. Garbisch, J. Chem. Education,45, a) 311; b) 402, c) 480 (1968).
T. M. Tackman and S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, Pergamon Press, Oxford (1969), p. 202.
M. Zanger, Organic Mag. Resonance,4, 1 (1972).
W. Brugel, Nuclear Magnetic Resonance Spectra and Chemical Structure, Vol. 1, Academic Press (1967), p. 15.
J. Ronayne and D. H. W. Williams, Annual Review of NMR Spectroscopy,2, 83 (1969).
V. J. Kowalewski, Progress in Nuclear Magnetic Spectroscopy,5, 1 (1969).
J. H. Noggle and R. E. Schirmer, Nuclear Overhauser Effect, Academic Press (1971).
Additional information
A. A. Zhdanov Irkutsk State University. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–10, January–February, 1976.
Rights and permissions
About this article
Cite this article
Kalabin, G.A., Kushnarev, D.F., Tyukavkina, N.A. et al. PMR spectra of natural stilbene compounds. Chem Nat Compd 12, 1–7 (1976). https://doi.org/10.1007/BF00570166
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00570166