Skip to main content
Log in

Glycoalkaloids of Solanum commersonii Dun. ex Poir

  • Published:
Euphytica Aims and scope Submit manuscript

Abstract

Five glycoalkaloids were identified from the aerial parts of wild Solanum commersonii Dun. ex Poir growing in Uruguay and their structures elucidated mainly by chemical and spectroscopic methods. In addition to the already known commersonine, demissine, tomatine and dehydrocommersonine, a new glycoalkaloid, identified as δ5-demissine, solanid -5-en-3-O- {β-D-Glcp-(1→2)-[β-D-Xylp-(1→3) ]β-D-Glcp-(1→4)-β-D-Galp } was found. Tomatine and dehydrocommersonine have not been reported earlier as components of this plant. The glycoalkaloid composition found in the wild plants studied differ significatively from those described earlier, and have some implications in taxonomy and its use in potato breeding.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Chen, S., J.D. Derrick, F.A. Mellon & K.R. Price, 1994. Analysis of glycoalkaloids from potato shoots and tomatoes by Four-sector Tandem Mass Spectroscopy. Anal Biochem 218: 157–169.

    Article  PubMed  CAS  Google Scholar 

  • Deahl, K.L., S.L. Sinden & R.J. Young, 1993. Evaluation of wild tuber-bearing Solanum accessions for foliar glycoalkaloid level and composition. Am Potato J 70: 61–69.

    CAS  Google Scholar 

  • Domon, B. & C.E. Costello, 1988. A systematic nomenclature for carbohydrate fragmentation in FAB MS/MS spectra of glycoconjugates. Glycoconjugate J 5: 397–409.

    Article  CAS  Google Scholar 

  • Hakomori, S., 1964. A rapid permethylation of glycolipids and polysaccharides catalised by NaDMSO in DMSO. J Biochem (Tokyo) 55: 205–208.

    CAS  Google Scholar 

  • Hawkes, J.G., 1992. Biosystematics of Solanum. In: P. Harris (Ed.), The Potato Crop, 2nd ed., pp. 13–64. Chapman-Hall, London.

    Google Scholar 

  • Jansson, P.-E., L. Kenne, H. Liedgren, B. Lindberg & J. Lönngren, 1976. A practical guide to the methylation analysis of carbohydrates. Chem Commun Univ Stockholm 8: 1–74.

    Google Scholar 

  • Kaneko, K., M. Tanaka, U. Nakaoka, N. Yoshida & H. Mitsushasi, 1984. Camtschacanidine, an alkaloid from Fritillaria camtschatcensis. Phytochemistry 20: 327–329.

    Article  Google Scholar 

  • Krebs, K.G., D. Heuser & H. Wimmer, 1969. In: Stahl (Ed.), Thin Layer Chromatography, pp. 854–905. Springer, New York.

    Google Scholar 

  • Osman, S.F., S.F. Herb, T.J. Fitzpatrick & S.L. Sinden, 1976. Commersonine, a new glycoalkaloid from two Solanum species. Phytochemistry 15: 1064–1067.

    Article  Google Scholar 

  • Osman, S.F., T.A. Johns & K.R. Price, 1986. Sisunine, a glycoalkaloid found in hybrids between Solanum acaule and Solanum × ajanhuiri. Phytochemistry 25: 967–968.

    Article  CAS  Google Scholar 

  • Petersen, H.W., P. Molgaard, U. Nyman & C.E. Olsen, 1993. Chemotaxonomy of the tuber-bearing Solanum species, subsection Potatoe (Solanaceae). Biochem Syst Ecol 21: 629–644.

    Article  CAS  Google Scholar 

  • Radeglia, R., G. Adam & H. Ripperger, 1977. 13C NMR spectroscopy of Solanum steroid alkaloids. Tetrahedron Lett 11: 903–906.

    Article  Google Scholar 

  • Raman, K.V. & E.B. Radcliffe, 1992. Pest aspects of potato production. In: P. Harris (Ed.), The Potato Crop, 2nd ed., pp. 477–506. Chapman-Hall, London.

    Google Scholar 

  • Sandford, L.L., K.L. Deahl, S.L. Sinden & R.S. Kobayashi, 1995. Glycoalkaloid content in tubers of hybrid and backcross populations from a Solanum tuberosum × S. chacoense cross. Am Potato J 72: 261–271.

    Google Scholar 

  • Schreiber, K., 1968. Steroidal alkaloids. In: R.H.F. Manske (Ed.), The Alkaloids, Vol. 10, pp. 1–192. Academic Press, New York.

    Google Scholar 

  • Sinden, S.L., L.L. Sanford & S.F. Osman, 1980. Glycoalkaloids and resistance to the Colorado potato beetle in Solanum chacoense Bitter. Am Potato J 57: 331–434.

    CAS  Google Scholar 

  • Tingey, W.M., 1984. Glycoalkaloids as pest resistance factors. Am Potato J 61: 157–167.

    CAS  Google Scholar 

  • Van Gelder, W.M.J., 1984. A new hydrolysis technique for steroid glycoalkaloids with unstable aglycones from Solanum spp. J Sci Food Agric 35: 487–494.

    CAS  Google Scholar 

  • Van Gelder, W.M.J., J.H. Vinke & J.J.C. Scheffer, 1988. Steroidal glycoalkaloids in tubers and leaves of Solanum species used in potato breeding. Euphytica S: 147–158.

    Google Scholar 

  • Van Gelder, W.M.J., L.G.M.Th. Tuinstra, J. van der Greef & J.J.C. Scheffer, 1989. Characterization of novel steroidal alkaloids from tubers of Solanum species by combined GC-MS. Implications for potato breeding. J Chromatogr 482: 13–22.

    Article  CAS  Google Scholar 

  • Waeghe, T.J., A.G. Darvill, M. McNeil & P. Albersheim, 1983. Determination by methylation analysis of the glycosyl linkage compositions of microgram quantities of complex carbohydrates. Carbohydr Res 123: 281–304.

    Article  CAS  Google Scholar 

  • Wilker, W. & D. Leibfritz, 1992. Complete assignment and comformational studies of Tomatine and Tomatidine. Mag Reson Chem 30: 645–650.

    Article  Google Scholar 

  • Zacharius, R.M. & S.F. Osman, 1977. Glycoalkaloids in tissue culture of Solanum species. Dehydrocommersonine from cultured roots of Solanum chacoense. Plant Sci Lett 10: 283–287.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vázquez, A., González, G., Ferreira, F. et al. Glycoalkaloids of Solanum commersonii Dun. ex Poir. Euphytica 95, 195–201 (1997). https://doi.org/10.1023/A:1002997616784

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1002997616784

Navigation