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MetaCyc Pathway: cardenolide biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: cardenolide biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisFatty Acid and Lipid BiosynthesisSterol Biosynthesis

Some taxa known to possess this pathway include : Digitalis, Digitalis lanata, Digitalis purpurea

Expected Taxonomic Range: Digitalis

Digitalis is a plant genus that belong to the Plantaginaceae and comprises several therapeutic species. Plants of the genus Digitalis produce cardiac glycosides [Gavidia07]. Cardenolides represent products of pharmaceutical value and possess a very complex basic skeleton of genin. It is widely accepted that the biosynthesis of cardenolides is connected to morphological differentiation, because the cardenolide content could be increased in the tissue after onset of differentiation [Berglund92] [Hirotani77], [Grave80]. Digitalis cardenolides are characterized by a steroid nucleus with rings connected cis-trans-cis' it has a 14beta-hydroxy group and an unsaturated five membered lactone ring is subsitituted at C-17beta.

Created 11-Sep-2008 by Pujar A, Cornell University


Berglund92: Berglund, T, Ohlsson, A. B (1992). "Effects of ethylene and aminoethoxyvinylglycine on cardenolide accumulation in tissue cultures of Digitalis lanata." J. Plant Physiol. 140, 395-398.

Gavidia07: Gavidia I, Tarrio R, Rodriguez-Trelles F, Perez-Bermudez P, Seitz HU (2007). "Plant progesterone 5beta-reductase is not homologous to the animal enzyme. Molecular evolutionary characterization of P5betaR from Digitalis purpurea." Phytochemistry 68(6);853-64. PMID: 17184799

Grave80: Grave, R, Luckner, M, Vogel, E, Tewes, A, Nover, L (1980). "Growth, morphogenesis and cardenolide formation in long-term cultures of Digitalis lanata." Planta Med. 40, 92-103.

Hirotani77: Hirotani, M, Furuya, T (1977). "Restoration of cardenolide-synthesis in redifferentiated shoots from callus cultures of Digitalis purpurea." Phytochemistry, 16, 610-611.

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bauer10: Bauer P, Munkert J, Brydziun M, Burda E, Muller-Uri F, Groger H, Muller YA, Kreis W (2010). "Highly conserved progesterone 5 beta-reductase genes (P5 beta R) from 5 beta-cardenolide-free and 5 beta-cardenolide-producing angiosperms." Phytochemistry 71(13);1495-505. PMID: 20598327

Herl06: Herl V, Fischer G, Muller-Uri F, Kreis W (2006). "Molecular cloning and heterologous expression of progesterone 5beta-reductase from Digitalis lanata Ehrh." Phytochemistry 67(3);225-31. PMID: 16386278

Herl09: Herl V, Fischer G, Reva VA, Stiebritz M, Muller YA, Muller-Uri F, Kreis W (2009). "The VEP1 gene (At4g24220) encodes a short-chain dehydrogenase/reductase with 3-oxo-Delta4,5-steroid 5beta-reductase activity in Arabidopsis thaliana L." Biochimie 91(4);517-25. PMID: 19166903

Kreis98: Kreis, W, Hensel, A, Stuhlemmer, U (1998). "Cardenolide biosynthesis in Foxglove." Planta Medica, 64, 491-499.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Pauli10: Pauli GF, Friesen JB, Godecke T, Farnsworth NR, Glodny B (2010). "Occurrence of progesterone and related animal steroids in two higher plants." J Nat Prod 73(3);338-45. PMID: 20108949

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Apr 30, 2016, biocyc14.