11-Allylcytisine and other minor alkaloids from unripe sophora secundiflora fruits

Phytochemistry
1979.0

Abstract

Sophora secundiflora (Ort.) Lag. ex DC. (Leguminosae) is a shrub native to the drier areas of the southwestern portions of the United States. The mature seeds from this plant are referred to as mescal beans, red beans and big drunk beans, and have been cited in the ethnobotanical literature [l-3] as being hallucinogenic becaise of their past use in certain native American ceremonies. A recent lay publication [4] has indicated that the mature seeds are part of the modem drug scene. These reports stimulated extensive investigations [S, 61 of the mature seed material resulting in the isolation of 6 known quinolizidine alkaloids (anagyrine, cytisine, As-dehydrolupanine, epi-lupinine, N-methylcytisine, and sparteine). The present report describes the isolation and structure elucidation of a new alkaloid, 11-allylcytisine 1, from the green, unripe fruits of S. secundiflora. Rhombifoline, lupanine and /I-isosparteine were also identified as being minor components in this material. Erythrina arborescens is distributed throughout the upper Gangetic plains, Assam and Manipur, extending west towards Nepal [l]. The seed of this plant has been reported to contain erysodine, erysovine, erysopine, hypaphorine, erythrascine, orientaline and erysophorine [2, 31], and the pod walls have been showed to contain erysodine, orientaline, hypaphorine and erysodinophorine [4]. In this paper we report the isolation of a new quaternary alkaloid 1, provisionally named erysopinophorine, from the pod walls.

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