Abstract
Transformed root cultures of Datura stramonium and of related species contain both aliphatic and aromatic tropane esters. It has been shown that these esters are produced by the action of several acyl transferases that transfer the acidic moiety to tropan-3α-ol (tropine) or tropan-3β-ol (pseudotropine) from various acyl-coenzyme A thioesters. The presence of these enzymes has been examined in a range of tropane-alkaloid-producing and non-tropane-alkaloid-producing species. Activities that esterify tropine appear to be confined to species that accumulate tropane alkaloids, whereas a number of species that do not accumulate tropane alkaloids possess some ability to esterify pseudotropine.
The present state of knowledge of these enzymes is reviewed. One of these activities, tigloyl-Coenzyme A:pseudotropine acyl transferase, has been purified to near homogeneity and the properties of this enzyme are summarized.
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Abbreviations
- CoA:
-
coenzyme A
- gc:
-
gas chromatography
- ms:
-
mass spectrometry
References
Beresford P. J. & Woolley J. G. (1974) Biosynthesis of tigloidine in Physalis peruviana. Phytochemistry 13: 2143–2144
Dräger B., Portsteffen A., Schaal A., McCabe P. H., Peerless A. C. J. & Robins R. J. (1992) Levels of tropinone-reductase activities influence the spectrum of tropane esters found in transformed root cultures of Datura stramonium L. Planta 188: 581–586
Evans W. C. (1990) Datura, a commercial source of hyoscine. Pharm. J. 244: 651–653
Hashimoto T., Nakajima K., Ongena G. & Yamada Y. (1992) Two tropinone reductases with distinct stereospecificities from cultured roots of Hyoscyamus niger. Plant Physiol. 100: 836–845
Hilton M. G. & Rhodes M. J. C. (1990) Growth and hyoscyamine production of ‘hairy root’ cultures of Datura stramonium in a modified stirred tank reactor. Appl. Microbiol. Biotechnol. 33: 132–138
Lounasmaa M. (1988) The tropane alkaloids. In: Brossi A. (Ed) The Alkaloids, vol. 33 (pp 1–81). Academic Press, Orlando
Nickon A. & Fieser L. F. (1952) Configuration of tropine and pseudotropine. J. Amer. Chem. Soc. 74: 5565–5570
Parr A. J. (1992) Alternative metabolic fates of hygrine in transformed root cultures of Nicandra physaloides. Plant Cell Rep. 11: 270–273
Parr A. J., Payne J., Eagles J., Chapman B., Robins R. J. & Rhodes M. J. C. (1990) Variation in tropane alkaloid accumulation within the Solanaceae and strategies for its exploitation. Phytochemistry 29: 2545–2550
Portsteffen A., Dräger B. & Nahrstedt A. (1992) Two tropinone reducing enzymes from Datura stramonium transformed root cultures. Phytochemistry 31: 1135–1138
Rabot, S. & Robins, R. J. (1992) Pseudotropine:tigloyl-CoA acyl transferase: an ester-forming enzyme from Datura stramonium transformed root cultures. In: (van Beek, T. A., ed.), Phytochemistry and Agriculture (p. 67). Abstracts of Phytochemical Society/Royal Netherlands Chemical Society meeting, Wageningen, April 1992
Robins R. J. & Walton N. J. (1994) The Biosynthesis of the Tropane Alkaloids. In: Cordell G. A. (Ed.) The Alkaloids, vol. 44 (pp 115–187). Academic Press, Orlando
Robins R. J., Parr A. J., Bent E. G. & Rhodes M. J. C. (1991a) Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures I. The kinetics of alkaloid production and the influence of feeding intermediate metabolites. Planta 183: 185–195
Robins R. J., Bachmann P., Robinson T., Rhodes M. J. C. & Yamada Y. (1991b) The formation of 3α- and 3β-acetoxytropanes by Datura stramonium transformed root cultures involves two independent acetyl-CoA-dependent acyl transferases. FEBS Letters 292: 293–297
Robins R. J., Woolley J. G., Ansarin M., Eagles J. & Goodfellow B. J. (1994a) Phenyllactic acid but not tropic acid is an intermediate in the biosynthesis of tropane alkaloids in Datura and Brugmansia transformed root cultures. Planta 194: 86–94
Robins R. J., Bachmann P. & Woolley J. G. (1994b) Biosynthesis of hyoscyamine involves an intramolecular rearrangement of littorine. J. Chem. Soc. Perkin Trans. I: 615–619
Saito K., Suzuki H., Takamatsu S. & Murakoshi I. (1993) Acyltransferases for lupin alkaloids in Lupinus hirsutus. Phytochemistry 32: 87–91
Walton N. J., Peerless A. C. J., Robins R. J., Rhodes M. J. C., Boswell H. D. & Robins D. J. (1994) Purification and properties of putrescine N-methyltransferase from transformed roots of Datura stramonium. Planta, 193: 9–15
Wink M. & Hartmann T. (1982) Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA: 13-hydroxylupanine O-tigloyltransferase from Lupinus albus L. Planta 156: 560–565
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Robins, R.J., Bachmann, P., Peerless, A.C.J. et al. Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures. Plant Cell Tiss Organ Cult 38, 241–247 (1994). https://doi.org/10.1007/BF00033883
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DOI: https://doi.org/10.1007/BF00033883