Subscribe to RSS
DOI: 10.1055/s-0042-118189
Triterpenoid Saponins from Maesa argentea Leaves
Publication History
received 24 March 2016
revised 06 September 2016
accepted 17 September 2016
Publication Date:
13 October 2016 (online)
![](https://www.thieme-connect.de/media/plantamedica/201618/lookinside/thumbnails/10-1055-s-0042-118189_pma0269-1.jpg)
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 1–4 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.
Key words
Maesa argentea - Myrsinaceae - saponins - antiprotozoal activity - maesabalides - maesasaponins-
References
- 1 Zhengyi W, Raven PH, Deyan H. Maesa argentea. Flora of China. Available at. http://www.efloras.org/florataxon.aspx?flora_id=2&taxon_id=200016845 Accessed February 2, 2016
- 2 Joshi AR, Joshi K. Piscicidal plants of nepal: checklist, ethnobotanical uses and indigenous practices. Ethnobotanical Leaflets 2006; 10: 342-349
- 3 Vermeersch M, Foubert K, da Luz RI, Van Puyvelde L, Pieters L, Cos P, Maes L. Selective antileishmania activity of 13,28-epoxy-oleanane and related triterpene saponins from the plant families Myrsinaceae, Primulaceae, Aceraceae and Icacinaceae. Phytother Res 2009; 23: 1404-1410
- 4 Foubert K, Vermeersch M, Theunis M, Apers S, Cos P, Claeys M, Luc VP, Pieters L, Maes L. LC-MS analysis of 13,28-epoxy-oleanane saponins in Maesa spp. extracts with antileishmanial activity. Phytochem Anal 2009; 20: 159-167
- 5 Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in Fab-Ms Ms spectra of glycoconjugates. Glycoconjugate J 1988; 5: 397-409
- 6 Germonprez N, Van Puyvelde L, Maes L, Van Tri M, De Kimpe N. New pentacyclic triterpene saponins with strong anti-leishmanial activity from the leaves of Maesa balansae . Tetrahedron 2004; 60: 219-228
- 7 Apers S, De Bruyne TE, Claeys M, Vlietinck AJ, Pieters LAC. New acylated triterpenoid saponins from Maesa lanceolata . Phytochemistry 1999; 52: 1121-1131
- 8 Tan NH, Zhou J, Zhao SX. Advances in structural elucidation of glucuronide oleanane-type triterpene carboxylic acid 3,28-O-bisdesmosides (1962–1997). Phytochemistry 1999; 52: 153-192
- 9 Maes L, Vanden Berghe D, Germonprez N, Quirijnen L, Cos P, De Kimpe N, Van Puyvelde L. In vitro and in vivo activities of a triterpenoid saponin extract (PX-6518) from the plant Maesa balansae against visceral Leishmania species. Antimicrob Agents Chemother 2004; 48: 130-136
- 10 Faizal A, Lambert E, Foubert K, Apers S, Geelen D. In vitro propagation of four saponin producing Maesa species. Plant Cell Tiss Org 2011; 106: 215-223
- 11 Theunis MH, Foubert K, Pollier J, Gonzalez-Guzman M, Goossens A, Vlietinck AJ, Pieters LAC, Apers S. Determination of saponins in Maesa lanceolata by LC-UV: development and validation. Phytochemistry 2007; 68: 2825-2830
- 12 Medeiros PM, Simoneit BRT. Analysis of sugars in environmental samples by gas chromatography-mass spectrometry. J Chromatogr A 2007; 1141: 271-278
- 13 Cos P, Vlietinck AJ, Vanden Berghe D, Maes L. Anti-infective potential of natural products: How to develop a stronger in vitro ‘proof-of-concept’. J Ethnopharmacol 2006; 106: 290-302
- 14 Mesia GK, Tona GL, Nanga TH, Cimanga RK, Apers S, Cos P, Maes L, Pieters L, Vlietinck AJ. Antiprotozoal and cytotoxic screening of 45 plant extracts from Democratic Republic of Congo. J Ethnopharmacol 2008; 115: 409-415