Alkaloids and other compounds of Symphytum tuberosum

Phytochemistry
1977.0

Abstract

The presence of senecio alkaloids in the Boraginaceae has been known for some time, Culvenor [1-4] and Men'shikov [5-8] obtained a number of new senecio alkaloids from plants of this family. However, there are only a few studies with Symphytum species. Jkhimidine and symphytine [9] were isolated from S. officinale. Echimidine, symphytine, an unknown alkaloid C,,H,,_,,O,N and a new alkaloid, anadoline were isolated from S. orientole [10-12]. There is only one paper dealing with S. tuberosum [13], some sugars and amino acids together with allantoin being reported. In this study the light petrol and chloroform extracts of the whole plant yielded n-heneicosane, palmitone, tricosanol as well as sitosterol and another steroidal alcohol C,,H,,O. The alcoholic extract showed the presence of mannose, glucose, galactose and strophanthobiose which was found earlier as a combined sugar in Strophanthus kombe [14], this is the first time it has been isolated in the free state. The alcoholic extract also yielded six alkaloids, two of them identified as anadoline and echimidine. In the aqueous extract of the plant the following amino acids were detected: aspartic acid glycine, leucine, serine, valine, alanine, glutamic acid, proline, methionine, isoleucine, phenylalanine, histidine and lysine (cf. also ref. [13]). Although allantoin is common in Symphytum species and has been reported in S. tuberosum [13], we could not detect it in our plant material. The genus Caltha has world-wide distribution in the northern hemisphere and has been the subject of early European reports of toxicity in cattle and horses [1]. In our present investigation of Caltha leptosepala and C. biflora, we isolated the pyrrolizidine alkaloid senecionine. One of the symptoms on ingestion of this alkaloid (severe gastrointestinal irritation [2]) corresponds to the reported symptom of Caltha poisoning [3]. The second alkaloid isolated has PMR, UV, and Rf's (cf ref. 4) identical to those of the quaternary aporphine alkaloid N,N-dimethyl lindcarpine. It has now come to our attention that the spectral and physical properties of N,N-dimethyl lindcarpine and its isomer, magnoflorine, are being reinvestigated [5]. Since the properties of these two aporphine alkaloids are very similar [6], the aporphine alkaloid could be either of these alkaloids or a mixture of the two. This is the first report to our knowledge of a pyrrolizidine alkaloid occurring in Ranunculaceae and the first report of the co-occurrence of pyrrolizidine and aporphine alkaloids.

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