Alkaloids calystegines

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. 

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. 

Tropane alkaloids Tropane alkaloids Quinine Indole alkaloids Calystegins Glycoalkaloids... 

The synthesis of amine 48 as an analogue of the alkaloid calystegine Bj has been achieved by successive treatment of oxime 49 (prepared from methyl-a-D-glucopyranoside in several steps) with NaOCl ZnlN,), PhjP, DIAD then H2/Pd black. ... 

Tropane alkaloids (TAs), a class of specialized metabolites with a bicyclic tropane ring in their structures, include clinically important hyoscyamine and scopolamine, the stimulant and narcotic cocaine, and the nortropane alkaloids calystegines. Plants producing TAs are distributed, sometime sporadically, across separate angiosperm families (e.g., Proteaceae, Convolvulaceae, Brassicaceae, Euphorbiaceae, Rhizophoraceae, Solanaceae, and Erythroxylaceae) (Griffin and Lin 2000). Studies of TA biosynthesis have been performed predominantly in Solanaceae plants, and thus little is known regarding TA pathways in other families. 

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

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. 

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). 

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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