Cardenolides biosynthesis

Groeneveld, H., van den Berg, B., Elings, J. and Seykens, D. (1990) Cardenolide biosynthesis from malonate in Asclepias curassavica. Phytochemistry, 29,3479-86. 

Herl, V., Albach, D., Mueller-Uri, R, Braeuchler, C., Heubl, G. and Kreis, W. (2008) Using progesterone 5p-reductase, a gene encoding a key enzyme in the cardenolide biosynthesis, to infer the phylogeny of the genus Digitalis. Plant Syst. Evol., 271, 65-78. 

These contents were still lower (one sixteenth) than those in the shoot culture, however, it is noteworthy that cardenolides which production were mainly reported to be produced in aerial parts or in organs related to aerial parts (e.g. shoot-forming calli or somatic embryo) (2, 3) were produced in hairy root cultures at relatively high contents. This study might be helpful in investigating the factors which affect cardenolide biosynthesis. 

Introduction Steroidal saponins Triterpenoid Saponins Biological Activity of Saponins Saponins in Food and Forage Plants Saponins and Insects Medicinal Uses of Saponins Alteration of Taste Properties Sweeteners Cardenolides Biosynthesis... 

Groeneveld, H. W., A. Binnekamp, and D. Seykens, Cardenolide biosynthesis from acetate in Asclepias curassavica. Phytochemistry, 30, 2577-2585 (1991). 

BR biosynthesis inhibitors are potentially valuable tools for studying BR biosynthesis (Asami and Yoshida, 1999). Triazoles are known BR biosynthesis inhibitors however, they are not very specific and also suppress the synthesis of gibberellic acid (Rademacher, 2000) or cardenolides (see above). A more specific BR biosynthesis inhibitor, brassinazole, was synthesized by modifying uniconazole (Min et al., 1999). Treatment of Arabidopsis seedlings with brassinazole resulted in a phenotype typical of BR-deficient mutants (Asami... 

Anastasia, M. and Ronchetti, F. (1977) Mechanism of 14p-hydroxylation in the biosynthesis of cardenolides the role of 14p-cholest-5-en-3p-ol. Phytochemistry, 16,1082-3. 

Luta, M., Hensel, A. and Kreis, W. (1998) Synthesis of cardenolide glycosides and putative biosynthesis precursors of cardenolide glycosides. Steroids, 63,44-9. 

Maier, M., Seldes, A. and Gros, E. (1986) Biosynthesis of the butenolide ring of cardenolides in Digitalis purpurea. Phytochemistry, 25,1327-9. 

SpirostanolS Cardenolides, and Related Compounds.— The biosynthesis of the spirostanols diosgenin (86), yonogenin (87), and tokorogenin (88) has been studiedin Dioscorea tokoro. Cycloartenol (72), cholesterol (75), and its... 

The bufatenolides (90) probably have a biosynthesis in plants similar to the cardenolides. Pregnenolone is incorporated into hellebrin [(90) with (89 Sp-OH, 19-oxo)] and scilliroside [(90) with (89 A )]. However, in the toad Bufo) cholanic acid derivatives are far better precursors than pregnane derivatives. This suggests that all five carbon atoms of the enolester ring (90) may be derived from cholesterol in the toad compared with only two in plants. In the toad, marinobufagin [(90) with (89 5 -OH, 14,15-oxide)] is the precursor of telecinobufagin [(90) with (89 5 -OH)]. ... 

Fig. 17. Biosynthesis of cardenolides from pregnenolone in higher plants [9].

C. procera R.Br and toxicity F. Briischweiler et at., Helv. Chim. Acta 52, 2086 (1969). Revised structure eidem, ibid. 2276. Sequestration by larvae of Monarch butterfly Danaus plexippus L. 1. N. Sieber et al.. J. Chem. Ecol. 6, 321 (1980). Quantitative analysis of cardenolides in latex and leaves of C procera eidem. Phytochemistry 21, 2343 (1982). Biosynthesis of labelled compd M. S. Lee, J. N. Sieber, ibid. 22, 923 (1983). 

Various aspects of steroid biosynthesis were included in a Royal Society Symposium. The published proceedings and other reviews have dealt with cyclase enzymes,water-soluble steroids and triterpenoids, the involvement of a 14(15)- or 8(14)-double bond and its reductionin cholesterol biosynthesis, biosynthesis of sterols, steroid metabolism in insects, pregnane steroids, cardenolides, and bufadienolides. ... 

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