Aristolactam-BII

Alkaloid Y, isolated from the bark of Schefferomitra subaequalis (Annonaceae), has now been shown to correspond to the known aristolactam BII (cepharanone-B) (72).51... 

Aristolactam-BII (80) (cepharanone-B) Aristolochia argentina Stephania cepharantha Y. Hayata" ... 

Of these alkaloids, aristolactams -All (78) and -BII (80), as well as cepharanone-A (82) and doryflavine (83), have been characterized recently, with the structural assignment for doryflavine being only tentative. Noteworthy is the fact that cepharanone-A (82) and aristolactam-BII (80) were found in Stephania cepharantha Y. Hayata (Menispermaceae), and that doryflavine (83) was isolated from Doryphora sassafras Endlicher (Monimiaceae). These are the first recorded occurrence of aristolactams outside the family Aristolochiaceae. 

Aristolactams were regarded as intermediates in the biosynthetic pathway of aristolochic acid, which was produced by aporphines via oxidation process. Eleven aristolactams were isolated from Fissistigma. Piperolactam A (A-95), piperolactam C (A-96), aristolactam AIHa (A-97), aristolactam BII (A-98), and agoniothalactam (A-99) were isolated from F. balansae [49]. Aristolactam FII (A-100), stigmalactam (A-101), aristolactam All (A-102), enterocarpam I (A-103), and velutinam (A-104) were isolated from F. oldhamii [49]. Aristolactam Bill (A-105) was isolated from both the species [49]. 

In the family Menispermaceae there are 4 bibliographic citations for 3 different compounds. Aristolochic acid I was isolated from Cocculus trilobus and the aristolactams cepharanone A and cepharanone B (= Aristolactam BII) were isolated from Stephemia cepharantha. 

SCHEME 7.19 Synthesis of Aristolactam BII (cepharanone B), Aristolactam BIB, Aristolactam FI (piperolactam A), A-methyl piperolactam A and Sauristolactam. Sonagashira coupling reaction. 

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