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On the Way to the Differentiation of Solamargine and Solamarine via NMR.

Results shown

Genetic and enzimatic studies of the metabolic pathways of plants contribute to the identification of biosynthetic route and the structural elucidation of secondary metabolites. Therefore, the challenge is the differentiation of cyclization in the biosynthetic steps of the aliphatic chain of cholesterol (ring F), which determine the constitution of the steroidal glycoalkaloids solamargine and -solamarine. It is supposed that cyclization of ring F occurs via attack on carbon-22 (C-22) which is below or on top of the plane using the methyl groups in C-26 or C-27 3.

Both steroidal glycoalkaloids were elucidated by 1D and 2D NMR. It is not possible make a quick differentiation of them based on the chemical shifts, the distinction becomes clear when the 1H spectra are overlapped. In principle, it’s not possible to say who is who, because both show the same kind of dipolar and scalar couplings 4,5.

Consequently, the aim of this study is to investigate the structural differences between solamargine and -solamarine, like: ring F conformation and configuration, using NMR spectroscopy and molecular modeling.

Literature cited

The following literature references are used for this poster:

1. Cárdenas P.D., Sonawane P.D., Heinig U., Bocobza S.E., Burdman S. & Aharoni A.. Phytochemistry, 113 (2015) 24-32.
2. Dolan L.C., Matulka R.A. and Burdock G.A.. Toxins, 2 (2010) 2289-2332.
3. Sonawane P.D., Pollier J., Panda S., Szymanski J., et. al. Nature Plants, 3 (2016) 1-13.
4. Ripperger H. & Porzel A.. Phytochemistry 46 (1997) 1279-1282.
5. Weissenberg M. Phytochemistry 58 (2001) 501-508.

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