Aristotelinone and serratoline: New indole alkaloids from Aristotelia serrata W.R.B. Oliver
✍ Scribed by I.Ralph C. Bick; Mohammad A. Hai; Nigel W. Preston; Rex T. Gallagher
- Book ID
- 104237258
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 126 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Aristotelinone and serratoline, two new Aristotetia alkaloids, are shown to have indole and indolenine structures respectively from their spectra and reduction products. The structure and absolute configuration of aristoteline (I), the main alkaloid of the New Zealand plant A. sepruta (and of the South American A. chitenda2) was established by X-ray crystallography'. A minor alkaloid of A. serrata, aristotelinone, was isolated by standard means and crystallised from methanol in fine needles, changing around 255O into longer needles which remained unaltered up to 320'. [a];' + 122.7" (MeOH + CHC13 1:l). From its molecular formula C20H24N20, aristotelinone had two less hydrogen atoms than (I), plus an oxygen; its 13C nmr spectrum was largely similar to that of aristoteline, except for a signal due to a carbonyl group, which from the ir and uv spectra was attached to the 3-position of an indole nucleusj. This . deduction was in accord with the absence of allylic proton signals in the 'H nmr spectrum, which otherwise resembled that of (I); in both spectra the 2 and 3 positions of indole appeared to be substituted, and this was confirmed by a -ve Ehrlich test.