Glycosides of 20-Deoxy Derivatives of Jujubogenin and Pseudojujubogenin from Bacopa monniera

Abstract

A detailed phytochemical investigation of an extract of Bacopa monniera resulted in the isolation of two new dammarane glycosides along with eight known compounds. They have been identified as glycosides of the 20-deoxy derivatives of jujubogenin and pseudojujubogenin. The structures were established by different spectroscopic methods that included 1D and 2D NMR experiments. The compounds were tested for their cytotoxicity, antileishmanial, antimalarial, antioxidant, and anti-inflammatory activities. Only few compounds exhibited mild to moderate cytotoxicity towards non-cancerous kidney cell lines.

References

• 1 Godfrey R K, Wooters J W. Aquatic and wetland plants of southeastern United States - dicotyledones. Athens; University of Georgia Press 1981.
• 2 Kapoor L D. Handbook of ayurvedic medicinal plants.  Boca Raton: CRC. Press;  2001 61.
• 3 Singh H K, Rastogi R P, Srimal R C, Dhawan B N. Effect of bacosides A and B on avoidance responses in rats.  Phytother Res. 1988;  2 70-5.
• 4 D'Souza P, Deepak M, Rani P, Kadamboor S, Mathew A, Chandrashekar A P. et al . Brine shrimp lethality assay of Bacopa monnieri .  Phytother Res. 2002;  16 197-8.
• 5 Sivaramakrishna C, Rao C V, Trimurtulu G, Vanisree M, Subbaraju G V. Triterpenoid glycosides from Bacopa monnieri .  Phytochemistry. 2005;  66 2719-28.
• 6 Pawar R, Gopalakrishnan C, Bhutani K K. Dammarane triterpene saponin from Bacopa monniera as the superoxide inhibitor in polymorphonuclear cells.  Planta Med. 2001;  67 752-4.
• 7 Russo A, Borrelli F, Campisi A, Acquaviva R, Raciti G, Vanella A. Nitric oxide-related toxicity in cultured astrocytes: effect of Bacopa monniera .  Life Sci. 2003;  73 1517-26.
• 8 Russo A, Izzo A A, Borrelli F, Renis M, Vanella A. Free radical scavenging capacity and protective effect of Bacopa monniera L. on DNA damage.  Phytother Res. 2003;  17 870-5.
• 9 Channa S, Dar A, Anjum S, Yaqoob M, Atta Ur R. Anti-inflammatory activity of Bacopa monniera in rodents.  J Ethnopharmacol. 2006;  104 286-9.
• 10 Renukappa T, Roos G, Klaiber I, Vogler B, Kraus W. Application of high-performance liquid chromatography coupled to nuclear magnetic resonance spectrometry, mass spectrometry and bioassay for the determination of active saponins from Bacopa monniera Wettst.  J Chromatogr A. 1999;  847 109-16.
• 11 Sinha J, Raay B, Das N, Medda S, Garai S, Mahato S B. et al . Bacopasaponin C: critical evaluation of anti-leishmanial properties in various delivery modes.  Drug Deliv. 2002;  9 55-62.
• 12 Russo A, Borrelli F. Bacopa monniera, a reputed nootropic plant: an overview.  Phytomedicine. 2005;  12 305-17.
• 13 Kulshreshtha D K, Rastogi R P. Chemical examination of Bacopa monniera. VI. Bacogenin A2. New sapogenin from bacosides.  Phytochemistry. 1974;  13 1205-6.
• 14 Chakravarty A K, Sarkar T, Masuda K, Shiojima K, Nakane T, Kawahara N. Bacopaside I and II: two pseudojujubogenin glycosides from Bacopa monniera .  Phytochemistry. 2001;  58 553-6.
• 15 Rastogi S, Pal R, Kulshreshtha D R. Bacoside A3 - a triterpenoid saponin from Bacopa monniera .  Phytochemistry. 1994;  36 133-7.
• 16 Ganapaty S, Thomas P S, Ramana K V, Karagianis G, Waterman P G. Dammarane and ceanothane triterpenes from Zizyphus glabrata .  Z Naturforsch B. 2006;  61 87-92.
• 17 Ganzera M, Gampenrieder J, Pawar R S, Khan I A, Stuppner H. Separation of the major triterpenoid saponins in Bacopa monnieri by high-performance liquid chromatography.  Anal Chim Acta. 2004;  516 149-54.
• 18 Chakravarty A K, Garai S, Masuda K, Nakane T, Kawahara N. Bacopasides III-V: three new triterpenoid glycosides from Bacopa monniera .  Chem Pharm Bull. 2003;  51 215-7.
• 19 Garai S, Mahato S B, Ohtani K, Yamasaki K. Dammarane-type triterpenoid saponins from Bacopa monniera .  Phytochemistry. 1996;  42 815-20.
• 20 Sawardekar J S, Sloneker J H, Jeanes A. Quantitative determination of monosaccharides as their alditol acetates by gas liquid chromatography.  Anal Chem. 1965;  37 1602-4.
• 21 Hara S, Okabe H, Mihashi K. Gas-liquid chromatographic separations of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates.  Chem Pharm Bull. 1987;  35 501-6.
• 22 Jain M, Khan S I, Tekwani B L, Jacob M R, Singh S, Singh P P. et al . Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues.  Bioorg Med Chem. 2005;  13 4458-66.