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Planta Med 2017; 83(14/15): 1227-1232
DOI: 10.1055/s-0043-116491
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Acetylated Furostene Glycosides from Solanum gilo Fruits[*]

Authors

  • Edwige Nana Tchoupang

    1   Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon

  • Christina Reder

    2   Department of Pharmacognosy, University of Vienna, Vienna, Austria

  • Sylvin Benjamin Ateba

    1   Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon

  • Martin Zehl

    2   Department of Pharmacognosy, University of Vienna, Vienna, Austria
    3   Department of Analytical Chemistry, University of Vienna, Vienna, Austria

  • Hanspeter Kählig

    4   Institute of Organic Chemistry, University of Vienna, Vienna, Austria

  • Dieudonné Njamen

    1   Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon

  • Franziska Höller

    2   Department of Pharmacognosy, University of Vienna, Vienna, Austria

  • Sabine Glasl-Tazreiter

    2   Department of Pharmacognosy, University of Vienna, Vienna, Austria

  • Liselotte Krenn

    2   Department of Pharmacognosy, University of Vienna, Vienna, Austria
Further Information

Publication History

received 07 February 2017
revised 05 July 2017

accepted 07 July 2017

Publication Date:
18 July 2017 (online)

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Abstract

In continuation of our work on a traditional mixture of spices called “Nkui”, used in Cameroon for its influence on womenʼs reproductive health, we investigated the chemical composition of Solanum gilo, one component of “Nkui”. A methanolic extract was studied in detail. After dereplication of several known compounds, two furo-5-stene-derived saponin glycosides with acetylated sugar moieties were isolated. By extensive 1- and 2D NMR experiments and HR-MS and GC-MS methods, the structures were elucidated as 26-[(3‴,4‴,6‴-tri-O-acetyl)-β-D-glucopyranosyloxy]-22-hydroxyfurost-5-en-3β-yl-O-α-L-rhamnopyranosyl-(1″→2′)-β-D-glucopyranoside (A) and 26-[(3‴,4‴,6‴-tri-O-acetyl)-β-D-glucopyranosyloxy]-22-hydroxyfurost-5-en-3β-yl-[O-α-L-rhamnopyranosyl-(1′′′′→4′)-O-α-L-rhamnopyranosyl-(1″→2′)]-β-D-glucopyranoside (B), both new natural compounds.

Key words

Solanum gilo Raddi - Solanum aethiopicum L. - Solanaceae - furostene-type glycosides - 26-[(3‴,4‴,6‴-tri-O-acetyl)-β-D-glucopyranosyloxy]-22-hydroxyfurost- - 5-en-3β-yl-O-α-L-rhamnopyranosyl-(1′′→2′)-β-D-glucopyranoside - 26-[(3‴,4‴,6‴-tri-O-acetyl)-β-D-glucopyranosyloxy]-22-hydroxyfurost- - 5-en-3β-yl-[O-α-L-rhamnopyranosyl-(1′′′′→4′)-O- - α-L-rhamnopyranosyl-(1″→2′)]-β-D-glucopyranoside

* Dedicated to Professor Dr. Max Wichtl in recognition of his outstanding contribution to pharmacognosy research.


Supporting Information

    Informative fragment ions in the MS/MS spectra of the [M + Na]+ ion and the [M – H2O + H]+ ion of A and B, and 1H NMR, 13C NMR, COSY, HMBC, HSQC, NOESY, and TOCSY spectra of A and B are available as Supporting Information.

  • Supporting Information (PDF)