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Extra info for Alkaloids Volume 4: Specialist Periodical Rep (Specialist Periodical Reports) (v. 4)
The radioactivity appeared then in jervine (1 38) and veratramine (139). A clear precursorproduct relationship between solanidine (140) and the c-nor-D-homo-steroidal bases, (1 38) and (139), is indicated, albeit under artificial conditions. A similar experiment was carried out with etiolated plants at the budding stage and here a less rapid conversion was observed. However, a new radioactive compound was isolated which was thought to be a hydroxy-solanidine. g. betanine (145). It has been shown1I3that incorporation of dopa Io9 K.
G. Paul, Lluydiu, 1973, 36, 36; R. B. Herbert, in ref. 2, p. 16, in ref. 14, p. 16. '~ constructed for their derivation from tryptophan with twelve intermediates (Scheme 13)if it is assumed that decarboxylation occurs only if a primary aminofunction is present. Trace amounts of (102)--(105) and (107) were present in alkaloid extracts but none of the mono-N-methyl compounds could be detected, although enzymic evidence" points to N-methylation occurring in discrete steps. If it is assumed that the two N-methylations are immediately sequential then only six pathways, illustrated for the grid in Scheme 13,need to be considered.
F. Collins, W. J. Donnelly, M. F. Grundon, D. M. Harrison, and C. G. S. Chem. , 1972, 1029. W. M. J. Knoll, R. J. Huxtable, and K. L. , J . Amer. Chem. ,1973, 95, 2703. 0. Wahlroos and A. I. Virtanen, Acta Chem. , 1959,13, 1906; A. I. Virtanen and P. K. Hietala, Acta Chem. , 1960, 14, 499, 502. J . A. Klun, C. L. Tipton, and T. A. Brindley, J . Econ. , 1967, 60, 1529. R. M. Couture, D. G. Routley, and G. M. Dunn, Physiol. , 1971,1, 515. J. E. Reimann and R. U . Byerrum, Biochemistry, 1964, 3, 847.