Anabasis aphylla

Comparison of these results indicates identity of the two substances isolated independently by Orekhov and Ehrenstein, but Spiith and Kesztler have suggested that Pictet s nicoteine and Ehrenstein s base, consisted of impure Z-anatabine (p. 46). In this connection it may be noted that Ehrenstein s base was laevorotatory in acid solution, whereas Salts of anabasine are dextrorotatory. These authors have themselves isolated Z-anabasine from tobacco. The identity of synthetic 2-(3 -Pyridyl)piperidine with dZ-anabasine seems to have been definitely established. Anabasis aphylla is the source of the anabasine raanufac-... 

Pyridine Group. Piperine, Piperovatine, Leucenol, Mimosine, Alkaloids of Ricinus communis, Foenugrec, vy eca Nut, Hemlock, Lobelia, Tobacco (Nicotiana spp.). Anabasis aphylla, Pomegranate Root Bark. ... 

Nicotinoids. Nicotine from tobacco was one of the earliest insecticides and was recommended for use in 1763 as a tea for the destruction of aphids (1,20). Nicotine [54-11 -3], L-l-methyl-2-(3 -pyridyl)pyrrolidine (1) (bp 247°C, d 1.009), is found in the leaves of Nicotiana tobacum and N. rustica (Solanaceae) in amounts ranging from 2 to 14%, and also is found in Duboisia hopwoodii and in Aesclepias syriaca. It occurs as the principal alkaloid along with small amounts of 12 other alkaloids of which nomicotine [494-97-3], 2-(3,-pyridyl)pyrrolidine (2) (bp 270°C, d 1.07 g/mL), and anabasine [494-52-0], l-2-(3 -pyridyl)piperidiae (3) (bp 281°C, d 1.048), are of insecticidal importance (see Alkaloids). Nomicotine occurs as both the D and L forms, the former in D. hopn oodii and the latter commonly predominating in Nicotiana. Anabasine is the chief alkaloid of Anabasis aphylla, where it occurs from 1—2% in the shoots and is found to ca 1% in Nicotianaglauca. 

Neonicotine) Anabasis aphylla (Chenopodiaceae), Sophora [insecticidal, toxic]... 

The well-known piperidine alkaloid anabasine, found in Anabasis aphylla L. (Chenopodiaceae) and Nicotiana glauca Graeb. (Solanaceae), is thought to be synthesized in plants through dimerization of A1-piperideine (followed by oxidation).243 A terpyridine nicotelline (173) was found in tobacco leaf,244andits structure was proved by synthesis.245... 

Anabasine, a minor tobacco alkaloid in plants of Anabasis aphylla, is found in trace amounts in tobacco smoke, and, like nicotine, is one of the earliest known insecticides. In maximum current generation studies anabasine is equivalent to ACh and appears to act at the a nicotinic ACh receptor. ISQ analogs of anabasine were prepared but no pharmacological activity was reported [33],... 

Derivation (1) Extraction from Anabasis aphylla and Nicotiana glauca, (2) synthetic. 

Chenopodiaceae. The alkaloid content in the twigs of Anabasis aphylla L. decreases toward the end of the vegetative period. When the aerial portion is severed the regenerated shoots are rich in alkaloid. Salsola ricMeri Karel similarly shows a decrease in alkaloid content at maturity and then salsoline predominates (355). 

In accord with previous conclusionsabout the relationship between lysine and anabasine (3), lysine has been found to be a precursor for (3) in Anabasis aphylla along a pathway which does not involve symmetrical intermediates.Aspartic acid was found to serve as a precursor for both rings of anabasine whilst lysine was incorporated into lupinine, again in accord with previous results. 

New methods for the separation of the alkaloids of Anabasis aphylla have been described, anabasine being conveniently isolated as its carbonate." ... 

Anabasine occnrs in the tobacco species Nicotiana glauca, Anabasis aphylla L., Chenopodiaceae, and Solanaceae. It is nsed as an insecticide and as a metal anticorrosive agent. 

Anabasine is also the chief alkaloid in another plant, the Asiatic Anabasis aphylla. 

Matrine-type alkaloids [as (6)] were found to be labelled by radioactive lysine and cadaverine in Goebelia pachycarpa and to be interconvertible. Quinolizidine alkaloids of the sparteine type [as (5)] are known to arise from three molecules of lysine via a symmetrical intermediate (cadaverine). Aphylline (8) also arises from three molecules of lysine in Anabasis aphylla, but without the participation of a symmetrical intermediate. ... 

CjoHiaNj, Mr 162.23, D. 1.046, mp. 9°C, bp. 270-272 C, [a]p -82.2°. A. is a tobacco alkaloid from many Nicotiana species (Solanaceae). Its name is derived from the plant Anabasis aphylla (Chenopo-diaceae) in which it occurs as the main alkaloid in addition it is found in several other plants from various families (including Fabaceae, Berberidaceae) and in marine ribbon worms it has also been identified as a venom component in north American ants. It exhibits toxicity similar to that of nicotine and is used as an insecticide. 

C,oH NO, Mr 169.27, mp. 68.5-69.2°C, bp. 269-270 °C, [alo -21° (C2H5OH) racemate, mp. 63 - 64°C (59 °C). L. and the 5-epimer epi-lupinine mp. 77-78°C, [alo +32° (CjHjOH)) are quinolizidine alkaloids of which only few members contain the bicyclic lupinine type structure. They occur in several Fabaceae genera . L. is also a component of the Che-nopodiaceae Anabasis aphylla. In addition, esters of epi-lupinine with acetic, coumaric, and ferulic acid are known as natural products. Several syntheses, some enantiosclective, of these simple quinolizidine alkaloids have been reported. ... 

Nornicotine and anabasine count amongthe minor alkaloids of tobacco. Whereas Nkotiana species contain the (S)-nornicotine, Duboisia hopwoodii produces the (J )-enantiomer. Anabasine is with up to 2.6% the principal alkaloid of Anabasis aphylla. The anabasine content in Nkotiana glauca is comparatively high and reaches 1 %. 

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