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Biosynthetic production of aberrant alkaloids in Dolichothele sphaerica (Cactaceae).

Preliminary studies of the production of aberrant alkaloids were carried out by introducing unnatural precursors of dolichotheline into Dolichothele sphaerica in the hope that the corresponding dolichotheline analogs would be formed. Authentic samples of the required dolichotheline analogs were synthesized and served both as standards and as carriers during the extraction procedure. Radioactive analogs were separated from dolichotheline by preparative TLC, recrystallized to constant specific activity, and degraded to localize the label. Using appropriate precursors, the aberrant alkaloids N-isocaproylhistamine and 4(5)-[N-iso-valerylaminomethyl]imidazole were produced by D. sphaerica, while the plant appears to be unable to produce N-benzoylhistamine, N-isobutyrylhistamine, and N-isopropylhistamine.