Aristotelia alkaloid -peduncularine

With the exception of the recent isolation (2) of the unusual indole-pyrrolizidine base, peduncularine, from Aristotelia peduncularis (Labill.) Hook.f., alkaloids have not yet been reported from other genera of the Elaeocarpaceae. 

Peduncularine, an alkaloid of the roots and lower stems of the Tasmanian plant, Aristotelia pedmcularis (Labill.) Hook. f. (Elaeocarpaceae), has been assigned the structure (38 relative configuration only) on the basis of physical evidence.This alkaloid clearly belongs primarily to the indole series, but it should be noted that if a tryptamine residue is removed from the skeleton of (38). the remaining ten-carbon skeleton does not correspond to any of the hitherto encountered structural units derived from loganin. 

In the synthesis of peduncularine (814), the principal alkaloid of the Tasmanian shrub Aristotelia peduncularis, regioselective reduction of 793b with sodium borohydride followed... 

Peduncularine was obtained from Aristotelia peduncularis (Labill.) Hook f. by Bick et al who postulated an indole-pyrrolizidine structure (44) for this alkaloid. On the basis of more extensive spectroscopic studies (including C n.m.r. spectroscopic data) and degradative work, a revised structure (45) has been proposed by Ros et al which shows that peduncularine belongs to the class of monoterpene indole alkaloids, and has no connection with pyrrolizidine alkaloids. 

Aristotelia alkaloicis. Indole alkaloids from Aristo-telia spp. (Elaeocarpaceae), a family of approximately 50 compounds, e.g. aristoteline [C20H26N2, Mr 294.43, mp. 164°C, [a]o +16° CH3OH)] with hypotensive properties and peduncularine [C20H24N2, Mr 292.42,... 

Another genus, Aristotelia, contains indole alkaloids [e.g., peduncularine (44)], but these appear to be, at most, only distantly related to those of Elaeocarpus (Bick and Hai, 1985). This genus is found in the temperate regions of the southern hemisphere (Argentina, Australia, Chile, and New... 

Peduncularine is the principal alkaloid of Tasmanian shmb Aristotelia peduncularis that presents anticancer activity [267]. In 2006, Kitamura et al. [268] have presented a synthesis of the racemic alkaloid starting with the Diels-Alder... 

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