Antiviral, Haemolytic and Molluscicidal Activities of Triterpenoid Saponins from Maesa lanceolata: Establishment of Structure-Activity Relationships

Abstract

Ten saponins isolated from the leaves of Maesa lanceolata were tested for their antiviral, haemolytic and molluscicidal activities. The influence of the substitution pattern of these acylated triterpenoid saponins on their biological activities was investigated and structure-activity relationships were established. Maesasaponin VI₂ (3β-O-{[α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 3)]-[β-D-galactopyranosyl-(1 → 2)]-β-D-glucopyranuronyl}-21β,22α-diangeloyloxy-13 β,28-epoxyolean-16α,28α-diol), the most potent molluscicidal compound (LC₅₀ 0.5 ppm), also showed virucidal and haemolytic activity. In general, 21,22-diacylation appeared to be associated with a virucidal (reduction factor of the viral titer ≥ 10³ at 50 μg/ml) and haemolytic activity (HC₅₀ ≤ 1 μg/ml).

Key words

Maesa lanceolata - triterpenoid saponins - saponin esters - antiviral activity - haemolytic activity - molluscicidal activity

References

• 1 Sindambiwe J B, Baldé A M, De Bruyne T, Pieters L, Van Den Heuvel H, Claeys M, Vanden Berghe D A, Vlietinck A J. Triterpenoid saponins from Maesa lanceolata .  Phytochemistry. 1996;  41 269-77
• 2 Sindambiwe J B, Calomme M, Geerts S, Pieters L, Vlietinck A J, Vanden Berghe D A. Evaluation of biological activities of triterpenoid saponins from Maesa lanceolata .  Journal of Natural Products. 1998;  61 585-90
• 3 Apers S, Foriers A, Sindambiwe J B, Vlietinck A, Pieters L. Separation of a triterpenoid saponin mixture from Maesa lanceolata: semipreparative reversed-phase wide pore high performance liquid chromatography with temperature control.  Journal of Pharmaceutical and Biomedical Analysis. 1998;  18 737-43
• 4 Apers S, De Bruyne T E, Claeys M, Vlietinck A J, Pieters L AC. New acylated triterpenoid saponins from Maesa lanceolata .  Phytochemistry. 1999;  52 1121-31
• 5 Vanden Berghe D AR, Haemers A, Vlietinck A J. Antiviral agents from higher plants and an example of structure-activity relationship of 3-methoxyflavones. In: Bioactive Natural Products: Detection, Isolation, and Structural Determination. Colegate SM, Molyneux RJ, editors Boca Raton; CRC Press 1993: 405-40
• 6 Pauwels R. Development of new agents against the human immunodeficiency virus (HIV)-evaluation methods, structure-activity relationships and mechanism of action. Ph. D. Thesis Leuven (Belgium); 1990: 8-65
• 7 Horwitz J P, Chua J, Noel M. Nucleoside V. The monomesylates of 1-(2’-deoxy-β-D-lyxofuranosyl) thymine.  Journal of Organic Chemistry. 1964;  29 2076-8
• 8 Van Marck E AE. The glomerulopathy associated with Schistosoma mansoni infection. An experimental study in the mouse.  Acta Leidensia. 1983;  50 1-123
• 9 Simoes C MO, Amoros M, Schenkel E P, Shin-Kim J -S, Rücker G, Girre L. Preliminary studies of antiviral activity of triterpenoid saponins: relationships between their chemical structure and antiviral activity.  Planta Medica. 1990;  56 652-3
• 10 Apers S. Structure elucidation and biological evaluation of active constituents isolated from three medicinal plants: M. lanceolata, Q. africana and A. moluccana . PhD thesis University of Antwerp (Belgium); 2000: 30-57
• 11 Abe H, Sakaguchi M, Konishi H, Tani T, Arichi S. The effects of saikosaponins on biological membranes. 1. The relationship between the structures of saikosaponins and haemolytic activity.  Planta Medica. 1978;  34 160-6
• 12 Hänsel R, Sticher O, Steinegger E. Pharmakognosie-Phytopharmazie. Berlin; Springer-Verlag 1999: 530-2
• 13 El-Garem A A. Schistosomiasis.  Digestion. 1998;  59 589-605
• 14 Marston A, Maillard M, Hostettmann K. Search for antifungal, molluscicidal and larvicidal compounds from African medicinal plants.  Journal of Ethnopharmacology. 1993;  38 215-23
• 15 Hostettmann K, Marston A. Saponins. In: Chemistry and pharmacology of natural products. Phillipson JD, Ayres DC, Baxter H, editors Cambridge; Cambridge University Press 1995: 252-61
• 16 Clark T E, Appleton C C, Drewes S E. A semi-quantitative approach to the selection of appropriate candidate plant molluscicides - a South African application.  Journal of Ethnopharmacology. 1997;  56 1-13