Condensed tannins synthesis

PETERS, D.J., CONSTABEL, C.P., Molecular analysis of herbivore-induced condensed tannin synthesis cloning and expression of dihydroflavonol reductase from trembling aspen (Populus tremuloides). Plant J., 2002,32, 701-712. 

Foo L Y, Hemingway R W 1984 Condensed tannins Synthesis of the first branched pro-cyanidin trimer. J Chem Soc Chem Commun 85-86... 

Delcour, J.A., Ferreira, D., and Roux, D.G., Synthesis of condensed tannins part 9. The condensation sequence of leucocyanidin with (-l-)-catechin and with the resultant procyanidins. J. Chem. Soc. Perkin Trans. /1711, 1983. 

Yoneda, S., Kawamoto, H., and Nakatsubo, F., Synthesis of high molecular mass condensed tannins by cationic polymerization of flavan-3,4-carbonate, J. Chem. Soc., Perkin Trans. 1, 1025, 1997. 

Clausen TP, Reichardt PB, Bryant JP, Provenza FD. 1992. Condensed tannins in plant defense a perspective on classical theories. In Plant Polyphenols Synthesis, Properties, Significance. Hemingway RW, Laks PE, Editors. New York. Plenum, pp. 639-651. 

However, not all related species or conspecific populations respond similarly under the same UV influence. For example, Betula pendula and B. resinifera, two closely related birch species collected from populations in Europe and Alaska, generally produce a number of flavonoids, hydroxycinnamic acids, and condensed tannins in larger quantity in exposed leaves to artificial UV-B photon fluxes (4.9 kJ m d for 3 hr/day of biologically active radiation) than in non radiated plants (Lavola, 1997). In B. pendula populations the major increase was in flavonoid synthesis but in B. resinifera the bias was towards the hydroxycinnamic acids and condensed tannins. Besides, allopatric (geographically distant) populations of birch reacted differently in the synthesis of specific compounds. For example, chlorogenic acid increased by 22 and 92% in plants from Germany and Alaska, respectively, but in Finnish plants there was no increment at all. 

The publication of the chapter, Condensed Tannins , in CONAP-I in 1999, has sparked an unprecedented growth in studies relevant to the chemistry and biology of the proanthocyanidins. Whereas efforts on the synthesis previously focused on structure elucidation of naturally occurring analogues, its emphasis over the... 

D. Ferreira J. P. Steynberg J. F. W. Burger B. C. B. Bezuidenhoudt, Oxidation and Rearrangement Reactions of Condensed Tannins. In Plant Polyphenols Synthesis, Properties, Significance (Basic Life Sciences - Volume 59)] R. W. Hemingway,... 

Another notable achievement is the synthesis of a high molecular mass condensed tannin that is based upon the cationic polymerization of 3, 4, 5,7-tetrabenzyloxyflavan-3,4-carbonate (60), available in 92% yield via treatment of the parent flavan-3,4-diol with N,N -carbonyldii-midazole, using Lewis acid (e.g. BF3, TiCU, SbCls, Ph3C BF4)... 

Roux, D.G., and D. Ferreira Structure and Function in the Biomimetic Synthesis of Linear, Angular and Branched Condensed Tannins. Pure Appl. Chem., 54, 2465 (1982). 

Botha, J.J., D. Ferreira, and D.G. Roux Condensed Tannins Direct Synthesis, Structure, and Absolute Configuration of Four Biflavanoids from Black Wattle Bark ( Mimosa ) Extract. J. Chem. Soc., Chem. Commun., 700 (1978) Synthesis of Condensed Tannins. Part 4. A Direct Biomimetic Approach to [4,6]- and [4,8]-Biflavanoids. J. Chem. Soc., Perkin Trans. 1, 1235 (1981). 

Hemingway, R.W., and L.Y. Foo Condensed Tannins Quinone-methide Intermediates in Procyanidin Synthesis. J. Chem. Soc., Chem. Commun., 1035 (1983). 

Contents E. HASLAM The Metabolism of Gallic Acid and Hexahydroxydi-phenic Acid in Higher Plants. — D. G. ROUX and D. FERREIRA The Direct Biomimetic Synthesis, Structure and Absolute Configuration of Angular and Linear Condensed Tannins. — ST. J. GOULD and ST. M. WEINREB Streptonigrin. — D. J. ROBINS The Pyrrolizidine Alkaloids. — J. W. DALY Alkaloids of Neotropical Poison Frogs (Dendrobatidae). 

Young DA, Young E, Roux DG, Brandt EV, Ferreira D (1987) Synthesis of condensed tannins. 19. Phenol oxidative coupling of (-t)-catechin and (-t)-mesquitol - conformation of bis-(-l-)-catechins. J Chem Soc Perkin Trans 1 2345-2351... 

Botha, J.J., Viviers, P.M., Yoimg, D.A. et al. (1982). Synthesis of condensed tannins. Part 5. The first angular [4,6 4,8]-triflavanoids and their natural coimterparts. Journal of the Chemical Society Perkin Transactions I, 527-533. 

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