Matrines

Lupanine, Sparteine, Anagyrine, Cytisine, Matrine and Associated Bases. . . . . . . -. ... 

The last isomer, the so-called aldotripiperideine (185), is obtained by the action of acid catalysts on a-tripiperideine at its boiling point (298,299), or in aqueous solution at pH 9.2 and 100°C. Further aldol reaction between tetrahydroanabasine and A -piperideine obviously occurs. Hydrogenolysis of this compound gives dihydroaldotripiperideine (186) which is convertible into matridine (187), a reduction product of the alkaloid matrine. 

The reaction of 2-(a-pyridyl)alkylmalonic acid with J -piperideine leading to formation of 3-((x-pyridyl)quinolizidine-l-carboxylic acid on decarboxylation, has been used by Van Tamelen and Foltz (316) for the syntheis of the alkaloid lupanine (Scheme 20). A very elegant synthesis of matrine has been accomplished by Bohlmann et al. (317). 

Xanthates serve as a reliable source of electrophilic radicals, and this was exploited by Zard and coworkers for a short synthesis of ( )-matrine (3-304), a naturally occurring alkaloid which has been claimed to have anti-ulcerogenic and anticancer properties [116]. Heating a mixture of xanthate 3-299 and the radical acceptor 3-300 (3 equiv.) in benzene in the presence of lauroyl peroxide as initiator, gave 3-301 in 30% yield and a 3 1 mixture of the tetracylic products 3-302 and 3-303 in 18% yield (Scheme 3.76) [117]. The three compounds could be converted into the... 

Scheme 3.76. Domino radical sequence in the total synthesis of ( )-matrine (3-304).

Quinolizine alkaloids, including sophocarpine, matrine and sophoridine have been determined by GC-MS techniques in kuhuang, a traditional Chinese medicine (GC = gas chromatography) <2005MI967>. Similarly, GC-MS has allowed a phytochemical study of the quinolizidine alkaloids of Genista tenera <2005MI264>. 

The high-performance liquid chromatography (HPLC) determination of quinolizidine alkaloids in Radix Sophora flavescens was assisted by using tris(2,2 -bipyridyl)ruthenium(n) electrochemoluminescence <2004MI237>. Tandem HPLC-MS techniques have allowed the development of a sensitive and specific method for the determination of sophocarpine, matrine, and sophoridine in rabbit plasma <2005MI1595>. 

Cho, C. H., Chuang, C. Y. and Chen, C. F. 1986. Study of the antipyretic activity of matrine, a lupin alkaloid isolated from Sophora subprostata. Planta Medica, 343-345. 

Molecular and crystal structures of the majority of matrine steroisomers have been discussed by Sadykov et al. 68-78). Three-dimensional structures of the following compounds were elucidated (+)-matrine (4) 68), (+)-matrine A -oxide... 

The absolute configurations of (+)-matrine, (+)-allomatrine, (+)-isomatrine, and other alkaloids of this series having the (5) configuration at C-5 has been established (81). 

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