Securinines

Securinine [3610-40-2] (137), C 2H 5N02, is the major alkaloid of Securinega surroticosa Rehd. and has been shown to arise from two amino acid fragments, lysiae (24) andtyrosiae (25). 

Reactions at the aromatic nucleus that are quite different from the usual mild condensations and rearrangements which apparendy generate the typical alkaloids already discussed must be iavolved. Securinine (137) is reported to stimulate respiration and increase cardiac output, as do many other alkaloids, but it also appears generally to be less toxic (98). 

The effects of micelles of cetyltrimethylammonium bromide (CTABr), tetradecyl-trimethylammonium bromide (TTABr) and sodium dodecyl sulfate (SDS) on the rates of alkaline hydrolysis of securinine (223) were studied at a constant [HO ] (0.05 m). An increase in the total concentrations of CTABr, TTABr and SDS from 0.0 to 0.2 M causes a decrease in the observed pseudo-first-order rate constants (kobs) by factors of ca 2.5, 3, and 7, respectively. The observed data are explained in terms of pseudophase and pseudophase ion-exchange (PIE) models of micelles. Cationic micelles of CTABr speed attack of hydroxide ion upon coumarin (224) twofold owing to a concentration effect. ... 

Securinega suffruticosa (Pall.) Rehd. Yi Ye Chan (leaf, flower, twig) Securinine, allosecurinine, securinol, dihydrosecurinine, securitinine, phyllantidine.33 This herb may be toxic. Treat infantile paralysis, neurasthenia, neuroparalysis. 

Carbon-13 n.m.r. assignments have been reported for a number of isomeric 3-butyl-5-methyloctahydroindolizines that were synthesized in studies of the trial pheromone of the Pharaoh ant, and for some closely related indolizidines. This work includes a detailed discussion of the preferred conformations of these compounds.15 Securinegine, a minor alkaloid from Securinega suffruticosa Rehd., is isomeric with securinine, and the structure (22) has been proposed.16... 

Securinine.—Further details of one group s study of the biosynthesis of securinine (13) have been published.21 The origins of this alkaloid are well defined,22 and information which adds to this definition is that tyrosine is incorporated without loss of tritium from the carbon atoms flanking the phenolic hydroxy-group.21... 

Rather similar degradation processes are reported for the indolizi-dine alkaloid securinine.66... 

BicucuUme (AA), cryptopine, hydrastine, corlumine, and related isoquinoline alkaloids (AA) securinine harmaline and related (J-carbohne alkaloids (A) muscimol (A) securinine (AA)... 

DL-[2- C]Lysine [as (1)] and [2- C]-A -piperideine [as (2)] afforded securinine (3) in which the label was confined essentially to the asterisked carbon atom. Further, [i 5-6- H 6- C]-DL-lysine [as (1)] gave securinine without loss of tritium. Consequently C-6 of lysine does not undergo oxidation in the course of securinine biosynthesis and so the e-amino-group of (1) must be retained whilst the a-amino-group and carboxy-function are lost. The combined results are consistent with the hypothetical route to securinine shown in Scheme 1. This pathway will now gain more validity if alkaloids with structures similar to those of the proposed intermediates can be found in Securinega or related plants. 

It is interesting to note that securinine (3) is the first among those alkaloids with a nitrogen atom common to two rings which is known to avoid a symmetrical intermediate (c/. ref. 17). 

Securinega suffructicosa Securinine Sesamum indicum Silybium marianum Silymarin Taxifolin Sophora flavescens Sphocar dipine Soybean isoflavones Daidzein Daidzin Genistein Genistin Glycitein Glyzitin... 

This relatively large and interesting group has not been reviewed. Fifty Securinega species have been screened for securinine (11) content. The optical... 

E. NMR Spectra of Securinine, Allosecurinine, and Some of Their Hydrogenated Derivatives. 458... 

Seourinine, the most abundant alkaloid of this group, was first isolated by Russian workers in 1956 but its structure was fully established only in 1962. In the subsequent years a variety of alkaloids of the same skeletal type (1) but differing in stereochemistry and minor functionality were isolated and characterized. More recently, three alkaloids possessing a lower homolog structmre (2) of the seourinine type were discovered. Table I lists the known alkaloids according to these two subgroups. Several alkaloids (phyllanthidine, suffruticodine, and suffruticonine) have not been structurally elucidated but their molecular formulas and spectral properties indicate most probably a securinine-type skeleton (Section II, L). 

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