The Isolation of Hordenine and Norsecurinine from Securinega Virosa (Baill.). The structure of Norsecurinine

Abstract

From the ground roots of Securinega virosa, hordenine and a new alkaloid (norsecurinine) have been isolated. The structure of the latter alkaloid has been elucidated.

The Securinega Alkaloids

“…Moreover, the hypothesis of a biosynthetic link between norsecurinine (27) and fluggeainol (33) via 14,15-epoxynorsecurinine was proposed and needs further studies for confirmation. Interestingly, the authors did not observe any traces of neither fluggeainol (33) nor fluggeaine ether (34), which were previously extracted from the same plant species originated from China. Simplexine (30) was isolated from Phyllanthus simplex Retz.…”

“…Interestingly, additional studies on a species collected in South Africa did not give evidence for the presence of this compound and its ether. 38 Later, a phytochemical study on Flueggea leucopyra allowed the isolation of fluggeainol together with its C15 epimer, 15b-hydroxy-14,15-dihydronorsecurinine (34). 27 Therefore, the absolute stereochemistry of this compound was established as depicted.…”

“…Nigeria. 34 Its structure was deduced solely on the basis of spectral evidence and was elucidated as an analog of securinine with a pyrrolidine A ring instead of a piperidine. Therefore, the term norsecurinine was introduced.…”

Central depressant activity of butanol fraction of Securinega virosa root bark in mice

“…The crude methanol root bark extract of Securinega virosa has also been reported to prolong total duration of sleep induced by diazepam and decrease the number of head dips in hole-board test, in mice (Magaji et al, 2008b). The Compounds isolated from the root of the plant include alkaloids hordenine, norsecurinine (Iketubosin and Mathieson, 1963), dihydronorsecurinine, viroallosecurinine (Saito et al, 1964) and14,15-epoxynorsecurinine (Dehmlow et al, 1999). In pursuance of our target to isolate and characterize the bioactive constituents responsible for the observed behavioral properties, the methanol root bark extract of the plant was fractionated with various solvents.…”

An enantioselective approach to the Securinega alkaloids: the total synthesis of (+)-norsecurinine and (+)-allonorsecurinine

“…Additionally, skeletally rearranged (i.e., secu’amamine, 5 ),2 A-ring methoxylated (i.e., phyllanthine, 4 )3, oxidized (i.e., phyllantidine, 6 and nirurine, 7 ),4 and dimeric (i.e., flueggenines, 8 and 9) 5 congeners have been reported. The enantiomers of some Securinega alkaloids, virosecurinine ( 3 ),6 viroallosecurinine,7 and (−)-norsecurinine,8 have also been isolated from natural sources.…”