Chemotaxonomy and geographical distribution of tropane alkaloids William J. Grin a, *, G. David Lin b a School of Pharmacy, University of Queensland, St. Lucia, Qld 4067, Australia b School of Natural and Complementary Medicine, Southern Cross University, Lismore, NSW 2480, Australia Received 21 December 1998; received in revised form 14 July 1999 Abstract This review illustrates the distribution of tropane alkaloids within the families Solanaceae, Erythroxylaceae, Proteaceae, Euphorbiaceae, Rhizophoraceae, Convolvulaceae and Cruciferae. Whereas tropane alkaloids are characteristic of the genera Datura, Brugmansia (tree datura) and Duboisia of the Solanaceae, the distribution is more widespread with novel tropane derivatives in families not traditionally associated with these bases. The chemical nature of more recently discovered water- soluble calystegines and the di- and trimeric forms from the Convolvulaceae (e.g. schizanthines from Schizanthus spp.), truxillines from Bolivian coca leaves and moonines of Erythroxylum moonii are highlighted. Where possible and appropriate, links between the phytochemistry and taxonomy are discussed. # 2000 Elsevier Science Ltd. All rights reserved. Keywords: Tropane alkaloids; Scopolamine; Calystegines; Schizanthines; Truxillines; Moonines; Geographical distribution; Cultivation; Solana- ceae; Erythroxylaceae; Proteaceae; Euphorbiaceae; Rhizophoraceae; Convolvulaceae; Cruciferae 1. Introduction The tropane alkaloids of Datura (Datura stramo- nium ) were introduced to European medicine by Romany immigrants (gypsies). The generic name was derived from the Indian poison, dhat, used by a crim- inal class known as Thugs. Stramonium Herb was o- cial in a 17th German herbal. D. stramonium has synonyms such as Thornapple after its hooked capsule and Jamestown weed. Early settlers of Jamestown (USA) used it as a pot-herb with fatal results. The Solanaceae is considered the home of tropane alka- loids. Being an important food family, the potato’s lethal cousins became familiar as toxic plants and also as medicinal herbs. They were used for their hallucino- genic properties and became incorporated into folk- lore, i.e. witchcraft and tribal initiation ceremonies. Since tropane alkaloids have relatively simple chemical structures and were easy to extract, the majority con- fined to Solanaceous plants were soon isolated and identified. Then tropane alkaloids were located in other families, for example the Erythroxylaceae and Convolvulaceae, and some phylogenetic trends observed. Recently, the location of tropanes has widened with the discovery of dimeric and trimeric forms. Other tropane bases which were overlooked in previous investigations have been recognised and iso- lated. Parochially known as sugar-mimic alkaloids, they are very polar molecules that have avoided detection using traditional techniques. They have rekindled a pharmacological interest, as they seem to inhibit sugar metabolism. An excellent review given by Fodor is mainly devoted to the chemical synthesis of tropane al- kaloids (Fodor, G., 1997). 2. The Solanaceae The classification of the Solanceae into tribes by Phytochemistry 53 (2000) 623–637 0031-9422/00/$ - see front matter # 2000 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(99)00475-6 www.elsevier.com/locate/phytochem * Corresponding author.