Emilia flammea

The roots and leaves of Farfugium japonicum Kitam. (Compositae) have been shown to contain senkirkine (17). A new alkaloid, emiline (51), also a derivative of otonecine, is a constituent of Emilia flammea ... 

The fully saturated azocine (1), has not been exploited for application purposes up to 1995. All studies have been done for academic reasons. Applications of partially saturated azocines are not well known and the only system which has found its application is otonecine (87). Otonecine is the base portion of the alkaloid emiline which was originaUy extracted from the plant, Emilia flammea. Emiline has hepatotoxic and carcinogenic effects <83CL125, 83TL5731,89JCR(S)358,91JCR(S)46>. 

Step or two-step, rarely three-step, reactions. The only more complex transformation is the conversion of the retronecine moiety of senecionine N-oxide into the otonecine moiety of senkirkine. Root cultures of S. vernalis transform senecionine N-oxide into senkirkine (Fig. 7 A) without occurrence of detectable intermediates [58]. In Emilia flammea retronecine is an efficient precursor of emiline (Fig. 7 A) the major PA of the plant [611. The formation of otonecine was suggested to proceed by hydroxylation at C-8 and N-methylation of a retronecine ester followed by ketone formation with concomitant cleavage of the C-N bond (Fig. 7B) [61]. The origin of the M-methyl group of senkirkine from S-adenosylmethionine has been demonstrated [62]. 

Besides, it was shown that trachelanthamidine as well as retronecine were both efficient precursors for the necine otonecine, the base moiety of the PA emiline from Emilia flammea [60]. 

Kohlmuenzer, S., H. Tomczyk, and A. Saint-Fermin Alkaloid Emiline, a New Otonecine Ester from Emilia flammea. Diss. Pharm. Pharmacol. 23,419 (1971) [Chem. Abstr. 76, 96972 (1972)]. 

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