Calystegine alkaloids

Analysis and Biological Activities of Potato Clycoalkaloids, Calystegine Alkaloids, Phenolic Compounds, and Anthocyanins... 

This limited overview on the analysis of four classes of the following secondary potato metabolites is, except for anthocyanins, largely limited to our own studies of glycoalkaloids, calystegine alkaloids, and phenolic compounds. Because interest in these potato constituents arises from potential health benefits and occasional toxicity, we also include in this overview a brief discussion of these aspects that relate to composition and a description of experimental methods. The interested reader should consult the cited references for an entry into the extensive worldwide literature on the diverse analytical and biological aspects for these metabolites. 

Kato A, Asano N, Kizu H, Matsui K, Suzuki S, Arisawa M (1997) Calystegine alkaloids from Duboisia leichhardtii. Phytochemistry 45 425-429 Keiner R, Nakajami K, Hashimoto T, Drager B (2000) Accumulation and biosynthesis of calystegines in potato. J Appl Bot/Angew Bot 74 122-125... 

Waterman PG (1998) Alkaloid chemosystematics. In Cordell GA (ed) The alkaloids - chemistry and biology. Academic Press, San Diego, pp 537-567 Watson AA, Davies DR, Asano N, Winchester B, Kato A, Molyneux RJ, Stegelmeier BL, Nash RJ (2000) Calystegine alkaloids in the potato and other food plants. In Natural and selected synthetic toxins biological implications, ACS Symposium Series, vol 745. Oxford University Press, Washington DC, pp 129-139... 

Solanaceae, together with the Convolvulaceae, form a cluster of tropane and calystegine alkaloid occurrence (Figure 5). They comprise most of the plant genera and species from which calystegines have been identified, but the search for calystegines within other angiosperms has not yet been performed... 

The Moraceae family lies within the order Rosales in the eurosid clade 1, rather close to the cluster of Erythroxylaceae, Euphorbiaceae, and Rhizophoraceae (Figure 5). Calystegines were reported for M. alba and M. bombycis only (25,28,40). The family is much larger, however, with 38 genera and 110 species. This family should also be examined systematically for calystegine alkaloids. 

Many alkaloids can be produced by root cultures. The most known applications are with anabasine, nicotine, harmine, harmaline, hyoscyamine, calystegine, scopolamine, Enzymes such as... 

Goldmann, A., B. Message, D. Tepfer, R. J. Molyneux, O. Duclos, F. D. Boyer, and A. D. Elbein. Biological activities of the nortropane alkaloid, calystegine B2, and analogs structure-function relationships. J. Nat. Prod. 59 1137-1142. 

Molyneux RJ, Nash RJ and Asano N (1996) Chemistry and biological activity of the calystegines and related nortropane alkaloids. Alkaloids, Chemical and Biological Perspectives (ed Pelletier SW) Vol 11. Elsevier, Amsterdam, pp 303-343. 

Species in a relatively small number of herbivorous families dominate the list of plant feeders associated with alkaloid-rich foods. Lepidoptera (butterflies and moths) have catholic tastes when it comes to alkaloid-fortified plants, being represented by the families Nymphalidae (calystegine A-3, pyrrolizidine alkaloids lycopsamine type, harman), Arctiidae (senecionine type), Papilionidae (synephrine, isoquinolines), and Pterophoridae (monoterpene alkaloid rhexifoline).6 In addition, beetles (Chrysomelidae) sequester PAs (senecionine), grasshoppers (Acrididae) store senecionine, and aphids (Aphididae) sequester QAs (sparteine and diterpene alkaloids). 

A clever total synthesis of both enantiomers of animated 6a-carbahexoseptanoses 336 and ent-336, the immediate precursors of the tropane alkaloids calystegines A3 (337 and ent-337), was accomplished by Johnson and Bis [77], which centered upon the enzymatic desymmetrization of meso aminotropanediol 333. 

N-raethyl group and occur occasionally as minor constituents in plants producing tropane alkaloids [76,77]. A recent survey of the occurrence of calystegines in Solanaceae and Convolvulaceae plants discovered that they are widely distributed in these families [1,2,78-80],... 

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