New Cytotoxic Oleanane Saponins from the Infructescences of Polyscias amplifolia from the Madagascar Rainforest

Abstract

Bioassay-guided fractionation of an ethanolic extract of the infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-β-D-galactopyranosyloleanolic acid (3) and 3-O-β-D-galactopyranosyl-(1→4)-β-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyloleanolic acid (1) and 3-O-β-D-galactopyranosyl-(1→4)-α-L-arabinopyranosyloleanolic acid (2) on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against A2780 human ovarian cancer cell line, with IC₅₀ values in the range 6.7 to 10.8 μg/mL.

Polyscias amplifolia - Araliaceae - saponins - cytotoxicity

References

• 1 Biodiversity Conservation and Drug Discovery in Madagascar. Part 6. For part 5, see: Chaturvedula VSP, Schilling JK, Miller JS, Andriantsiferana, R, Rasamison V, Kingston DGI. New cytotoxic bis-5-alkylresorcinol derivatives from the leaves of Oncostemon bojerianum from the Madagascar rainforest.  J Nat Prod. 2002;  65 1627-32
• 2 Prakash C VS, Hoch J M, Kingston D . Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest.  J Nat Prod. 2002;  65 100-7
• 3 Bedir E, Toyang N J, Khan I A, Walker L A, Clark A M. A new dammarane-type triterpene glycoside from Polyscias fulva .  J Nat Prod. 2001;  64 95-7
• 4 Huan V D, Yamamura S, Ohtani K, Kasai R, Yamasaki K, Nham N T. et al . Oleanane saponins from Polyscias fruticosa .  Phytochemistry. 1998;  47 451-7
• 5 Proliac J, Chaboud A, Rougny A, Gopalsamy N, Raynaud J, Cabalion P. An oleanolic saponin from Polyscias fruticosa Harms var. yellow leaves.  Pharmazie. 1996;  51 611-2
• 6 Chaboud A, Rougny A, Proliac A, Raynaud J, Cabalion P. A new triterpenoid saponin from Polyscias fruticosa .  Pharmazie. 1995;  50 371
• 7 Gopalsamy N, Gueho J, Julien H R, Owadally A W, Hostettmann K. Molluscicidal saponins of Polyscias dichroostachya .  Phytochemistry. 1990;  29 793-5
• 8 Paphassarang S, Raynaud J, Lussignol M, Cabalion P. A new oleanolic acid from Polyscias scutellaria .  J Nat Prod. 1990;  53 163-6
• 9 Elujoba A A, Fell A F, Linley P A, Maitland D J. Triterpenoid saponins from fruit of Lagenaria breviflora .  Phytochemistry. 1990;  29 3281-5
• 10 Menu P, Bouquet A, Cavé A, Pousset J. Etude préliminaire des saponosides des fruits du Brenania brieyi De Wild. (Rubiacees).  Ann Pharm Fr. 1976;  34 427-38
• 11 Singh J. Two rhamnetin digalactosides and an oleanolic acid digalactoside from the flowers of Cassia laevigata .  Phytochemistry. 1982;  21 1832-3
• 12 Seebacher W, Weis R, Jurentisch J, Rauchnsteiner K, Haslinger E. Syntheses and hemolytic properties of arvensoside B isomers.  Monatsh Chem. 2000;  131 985-96
• 13 Pouchert C J, Behnke J. The Aldrich Library of ¹³C and ¹H-FT NMR spectra. Aldrich Chemical Co Milwaukee; 1993: 595B
• 14 Akimaliev A A, Putieva Z hM, Alimbaeva P K, Abubakirov N K. Triterpene glycosides of Scabiosa soongorica. V. β-Sitosterol, β-D-glucopyranoside and soongoroside A. Khim Prir Soedin 1988: 885-6
• 15 Odukoya O A, Houghton P J, Adelusi A, Omogbai E KI, Sanderson L, Whitfield P J. Molluscicidal triterpenoid glycosides of Dialium guineense .  J Nat Prod. 1996;  59 632-4
• 16 Wolfrom M L, Thompson A. D-Galactose. (α- and β-) D-galactose from lactose.  Methods Carbohydrate Chem. 1962;  1 120-2
• 17 Woo W S, Choi J S, Seligmann O, Wagner H. Sterol and triterpenoid glycosides from the roots of Patrinia scabiosaefolia .  Phytochemistry. 1983;  22 1045-7
• 18 Shao C J, Kasai R, Xu J D, Tanaka O. Saponins from leaves of Acanthopanax senticosus Harms., Ciwujia: structures of ciwujianosides B, C1, C2, C3, C4, D1, D2 and E.  Chem Pharm Bull. 1988;  36 601-8
• 19 McBrien K D, Bery R L, Lewes S E, Neddermann K M, Bursuker I, Huang S, Klehr S E, Leet J E. Rackicidins, new cytotoxic lipopeptides from Micromonospora sp. fermentation, isolation and characterization.  J Antibiotics. 1995;  48 1446-52
• 20 Agarwal P K. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.  Phytochemistry. 1992;  31 3307-30
• 21 Mimaki Y, Kuroda M, Asano T, Sashida Y. Triterpene saponins and lignans from the roots of Pulsatilla chinenesis and their cytotoxic activity against HL-60 cells.  J Nat Prod. 1999;  62 1279-83