Korea Polymer Journal, Vol.1, No.1, 27-33, April, 1993
Chiroptical Properties and Intrachromophoric Interactions in Oligomeric and Polymeric Molecules of Procyanidins
The chiroptical characteristics of the series of procyanidin oligomers (dimer through hexamer) and polymer connected by epicatechin monomeric unit(s) with 4β→8 interflavan bond(s) were extensively studied in this paper, based on solvent and molecular weight dependences of the molar ellipticity per mean residue, [θ], significantly observed between 210 and 250 nm. A dramatic increase in the [θ] of procyanidin molecules larger than the dimer suggests that the interactin between aromatic chromophores located in chiral positions with respect to each other becomes pronounced above the trimer. A simple model for intrachromophoric interaction provides good agreement between the experimental and calculate values of the circular dichroism (Δε)for the oligomeric and polymeric molecules of procyanidins
- Porter LJ, The Flavonoids, J.B. Harborne, Ed., Chapman and Hall, London, Chapter 2, p. 21 (1988)
- Hemingway RW, Natural Products Extraneous to the Lignocellulosic Cell Wall of Woody Plants, J.W. Rowe, Ed., Springer-Verlag, Berlin, Chapter 6.6, in press
- Hemingway RW, Karchesy JJ, Chemistry and Significance of Condensed Tannins, Plenum Press, New York (1989)
- Haslam E, Photochemistry, 16, 1625 (1977)
- Thompson RS, Jacques D, Haslam E, Haslam RJN, J. Chem. Soc.-Perkin Trans. 1, 1387 (1972)
- Jacques D, Opie CT, Porter LJ, Haslam E, J. Chem. Soc.-Perkin Trans. 1, 1637 (1977)
- Botha JJ, Ferreira D, Roux DG, J. Chem. Soc.-Perkin Trans. 1, 1235 (1981)
- Hemingway RW, Foo LY, Porter LJ, J. Chem. Soc.-Perkin Trans. 1, 1209 (1982)
- Hemingway RW, Karchesy JJ, McGraw GW, Weilesek RA, Phytochemistry, 22, 275 (1983)
- Bergmann WR, Mattice WL, ACS Symp. Ser., 358, 162 (1987)
- Filstra LF, Cho D, Bergamnn WR, Mattice WL, Chemistry and Significance of Condensed Tannins, R.W. hemingway and J.J. Karchesy, Eds., Plenum Press, New York, p. 335 (1989)
- Haslam E, Biochem. J., 139, 285 (1974)
- Hargermann AE, Robbins CT, J. Chem. Ecol., 13, 1243 (1987)
- Hemingway RW, Conner AH, ACS Symp. Ser., 385 (1989)
- Barrett MW, Klyne W, Scopes PM, Fletcher AC, Porter LJ, Haslam E, J. Chem. Soc.-Perkin Trans. 1, 2375 (1979)
- Mattice WL, Biopolymers, 13, 169 (1974)
- Sisido M, ACS Symp. Ser., 358, 343 (1987)
- Tilstra LF, Maeda H, Mattice WL, J. Chem. Soc.-Perkin Trans. 2, 1613 (1988)
- Jacques D, Haslam E, Bedford GR, Greatbanks D, J. Chem. Soc.-Perkin Trans. 1, 2263 (1974)
- Gargallo L, Radic D, Polymer, 24, 91 (1983)
- Cho D, Porter LJ, hemingway RW, Mattice WL, Polymer, 30, 1955 (1989)
- Cho D, Mattice WL, Porter LJ, Biopolymers, 29, 57 (1990)
- Cho D, Mattice WL, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem., 31(1), 203 (1990)
- Cho D, Tian R, Porter LJ, Hemingway RW, Mattice WL, J. Am. Chem. Soc., 112, 4273 (1990)
- Cho D, Mattice WL, J. Phys. Chem., 94, 3847 (1990)
- Cho D, Porter LJ, Mattice WL, Biopolymers, 31, 537 (1991)
- Lea AGH, J. Sci. Food Agric., 29, 471 (1978)
- Derdelinckx G, Jerumanis JJ, J. Chromatogr., 285, 231 (1984)
- Lambert JB, Shurvell HF, Lightner D, Cooks RG, Introduction to Organic Spectroscopy, MacMillan Publishing Co., New York, Chapter 9 (1987)
- Gaffield W, Foo LY, Porter LJ, Proc. Fed. Eur. Chem. Soc. Int. Conf. Circular Dichroism, 6, 338 (1985)
- Tilstra LF, Ph.D. Dissertation, Louisiana State University, Baton Rouge (1987)
- Platt JR, J. Chem. Phys., 17, 484 (1949)
- Lambert JB, Shurvell HF, Lightner D, Cooks RG, Introduction to Organic Spectroscopy, MacMillan Publishing Co., New York, Chapter 10 (1987)
- Dean JA, Lange's Handbook of Chemistry, 13th Ed., McGraw-Hill, New York, pp. 10-108 (1985)