| Structure Identification: |
| The Journal of Organic Chemistry, 1968, 33(10):3735-3738. | | The isolation and structural elucidation of novel derivatives of aristolochic acid from Aristolochia indica.[Reference: WebLink] | The isolation and structural elucidation are reported of three new companion Aristolochic acid Derivatives, aristolochic acid D (4), aristolochic acid-D methyl ether lactam (6), and aristololactam β-D-glucoside (8).
METHODS AND RESULTS:
Aristolochic acid D was assigned the molecular formula C17H11NO8 on the basis of elemental analysis and nmr spectroscopy. Methylation with diazomethane yielded the dimethyl derivative 5, and hydrogenation of 5 yielded aristolochic acid-D methyl ether lactam (6), identical with the material of natural origin. The structure of 5 was initially deduced on the basis of spectral evidence, and confirmed by direct comparison with a sample prepared by total synthesis. Spectral arguments are presented which favor structure 4 for Aristolochic acid D.
CONCLUSIONS:
Aristololactam β-D-glucoside (8) was characterized by elemental and nmr, ir, and uv spectral analysis. Acetylation gave the tetraacetate, 9. Lithium aluminum hydride reduction of 8, followed by mild acid hydrolysis, gave α-D-glucose and the aglycone 11, characterized by comparison with the product obtained by lithium aluminum hydride reduction of aristololactam. |
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