Stephania japonica protostephanine

During the period 1976-1986, biosynthetic studies on hasubanan alkaloids were carried out by Battersby et al. (81-84) for hasubanonine (5) together with protostephanine (57). The two alkaloids, isolated from Stephania japonica, arise from the same precursor, and their unusual structures are of biosynthetic interest, namely, the vicinally trioxygenated ring C in 5 and the unique natural example of a dibenz d,f ] azonine skeleton in 57. 

Stephania japonica (Thunb.) Miers. Qian Jin Teng (root) Stephanine, protostephanine, epistephanine, hypoepistephanine, homostephanoline, metaphanine, prometaphanine, hasubanonine, insularine, cyclanoline, steponine stephanoline, stepinonine.33 Treat nephritic edema, urinary tract infection, rheumatic arthritis, sciatic neuralgia. 

Protostephanine and Hasubanonine.—The unravelling of the biosynthesis of pro-tostephanine (36) and hasubanonine (37), both produced by Stephania japonica,... 

Battersby, A. R., R. C. F. Jones, R. Kazlauskas, A. P. Ottridge, C. PouPAT, and J. Staunton, Biosynthesis. Part 23. Degradative studies on the alkaloids hasubanonine and protostephanine from Stephania japonica, J. Chem. Soc. Perkin Trans. I, 2010-2015 (1981b). 

Some progress has been made in understanding the biosynthetic pathway to protostephanine in Stephania japonica Miers (Menispermaceae). This plant was treated with isotopically labeled amines 16-22, and all were found to be incorporated to an insignificant extent. On the other hand, tyrosine, tyramine, dopa, and dopamine were specifically incorporated into protostephanine. Analysis of these results indicate that (a) protostephanine is constructed from... 

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