Planta Med 2016; 82(18): 1568-1575
DOI: 10.1055/s-0042-118189
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Triterpenoid Saponins from Maesa argentea Leaves

Kenn Foubert
1   Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
,
Taposh Gorella
1   Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
,
Ahmad Faizal
2   Department of Plant Production, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
3   School of Life Sciences & Technology, Institut Teknologi Bandung, Bandung, Indonesia
,
Paul Cos
4   Laboratory for Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Antwerp, Belgium
,
Louis Maes
4   Laboratory for Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Antwerp, Belgium
,
Sandra Apers
1   Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
,
Danny Geelen
2   Department of Plant Production, Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium
,
Luc Pieters
1   Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 24. März 2016
revised 06. September 2016

accepted 17. September 2016

Publikationsdatum:
13. Oktober 2016 (online)

Abstract

Within an ongoing research program on saponins with potential antileishmanial activity, four previously undescribed saponins were isolated from Maesa argentea leaves and identified by LC-MS/MS, GC-MS, and 1D and 2D NMR spectroscopy as 3β-O-{([β-D-glucopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 3)]-[β-D-galactopyranosyl-(1 → 2)]-β-D-glucuronopyranosyl)}-21β-angeloyloxy-22α-butanoyloxy-13β,28-oxidoolean-16α,28α-diol (1), 3β-O-{([β-D-glucopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 3)]-[β-D-galactopyranosyl-(1 → 2)]-β-D-glucuronopyranosyl)}-21β,22α-angeloyloxy-13β,28-oxidoolean-16α,28α-diol (2), 3β-O-{([β-D-glucopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 3)]-[β-D-galactopyranosyl-(1 → 2)]-β-D-glucuronopyranosyl)}-21β-angeloyloxy-22α-(E)-cinnamoyloxy-13β,28-oxidoolean-16α,28α-diol (3), and 3β-O-{([α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 3)]-[β-D-galactopyranosyl-(1 → 2)]-β-D-glucuronopyranosyl)}-21β-angeloyloxy-22α-(E)-cinnamoyloxy-13β,28-oxidoolean-16α,28α-diol (4). Leaf material was obtained from a germinated seed that was clonally propagated using in vitro tissue culturing. Compounds 14 showed structural similarity with maesasaponins and maesabalides reported before from other Maesa spp. All four compounds showed in vitro activity against Plasmodium falciparum K1 and Leishmania infantum at micromolar concentrations. However, the observed inhibitory action must be considered nonspecific since they were also cytotoxic in the same concentration range.

Supporting Information

 
  • References

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