Borreria verticillata

Borreverine (243) is a bis-indole alkaloid of novel structural type, isolated from Borreria verticillata 147 it is formed by the combination of two 2-isopentenyl-Nb-... 

Borreria verticillata (L) G. F. Mey. Eyeyel Venom of snake (L or R) Parts mashed or powder... 

Previous studies of Borreria verticillata (Rubiaceae) yielded the indole alkaloid borrerine (224), and the bisindole alkaloids, borreverine (225), and is-oborreverine (226). A further investigation of this plant gave, in addition to these alkaloids, another new bisindole, spermacoceine (227), which was readily shown from the spectral data to be a derivative of borreverine, possessing a hydroxyethyl substituent at C-7, instead of the Ab-methyl tryptamine bridge in 225. The clearest departure was shown by the resonances of the oxymethylene C-5 in both the and NMR spectral data of 227 when compared to those of 225 137). 

Borrerine (28), a compound probably analogous in synthesis to lophocereine but belonging to the p-carboline series of alkaloids, has been found in Borreria verticillata (Rubia-ceae), along with a dimeric compound borreverine (29) (Fig. 35.8). This alkaloid has also been found in Flindersia four-nieri (Rutaceae) (Cordell and Saxton, 1981 Saxton, 1981). 

The finding of emetine (see Volume VII, p. 419) ia Spermacoce verti-cillata L. (Borreria verticillata Mey.) (Rubiaceae) 125) occasions no surprise but to find the Ipecac alkaloids in Allangium lamarkii Thw. (see Volume VII, p. 509), a plant now relegated to Alanginaceae, is a remarkable example of parallel evolution in plants w hich can be only remotely related 126). 

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