Abstract:
The debilic acid(C
18H
13O
7N)(Ⅰ)is a new component isolated from
Aristolochia debilis,S.et Z.as reported in our previous communication(Ⅰ).It closely resembles to Aristolochic acid(Ⅱ)C
17H
11O
7N,both in chemical and physical properties,Decarboxylation of(Ⅰ)by means of copper powder in quinoline,gave a compound C
16H
11O
5N(Ⅳ),m.p.206°,which was identified as 1-methoxy-5,6-methylene dioxy-9-nitro-phenagthrene,It is also obtainable from(Ⅱ)by the similar method.Owing to the negative result of the Kohn-Roth's determination of(Ⅳ),it is believed that the excessive methylene group in(Ⅰ)is an acetic radial rather than carboxyl group linking in(Ⅱ).Assuming the carboxyl group in(Ⅰ)is vicinal to the nitro-group,a neutral lactam should be formed instead of a basic amino compound.A lactam has been isolated in the present work.This fact interprets that the acetic radical should be existed either at 8-or 10-position. On the other hand,from the viewpoint of biogenetics,Aristolochiaceae,in the cou rse of evolution,is a family similar to those of Papaveraceae and Magnoliaceae.The last two mentioned families are well-known in containing alkaloids with tetrahydroisoquinoline nucleus which,in majority,carried a methoxy or methvlene-dioxy groups between 6-& 7-position. From the above facts and together with the strcture of aristolochic acid,the anthors suggest that the biosynthetic relationships between the aristolochic acid(including its related compounds)and aporphine series are as follows: If so,the acetic radical is more suitable in the 8-position than in the 10-position.In order to clarify the mutual relationship between the acidic and basic components,the alkaloid part which isolated from
A.debilis,was subjected to selenium dehydrogenation.A crystalline substance m.p.240-41°was obtained. From its UV-spectra it was identified as an analogue of 1-ethyl-phenanthrene which can be obtained from aporphine nuclea as a hydrocarbon. In consequence,the authors recommend the following tentative formula for the debilic aeid:-