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Planta Med 2007; 73(4): 380-383
DOI: 10.1055/s-2007-967163
Letter
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

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

Rahul S. Pawar1 , Shabana I. Khan1 , Ikhlas A. Khan1 , 2
  • 1National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, University, MS, USA
  • 2Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS, USA
Further Information

Publication History

Received: August 30, 2006 Revised: February 8, 2007

Accepted: February 13, 2007

Publication Date:
29 March 2007 (online)

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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.
    Google Scholar
  • 2 Kapoor L D. Handbook of ayurvedic medicinal plants.  Boca Raton: CRC. Press;  2001 61.
    PubMedGoogle Scholar
  • 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.
    PubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 5 Sivaramakrishna C, Rao C V, Trimurtulu G, Vanisree M, Subbaraju G V. Triterpenoid glycosides from Bacopa monnieri .  Phytochemistry. 2005;  66 2719-28.
    CrossrefPubMedGoogle Scholar
  • 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.
    Article in Thieme ConnectPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 12 Russo A, Borrelli F. Bacopa monniera, a reputed nootropic plant: an overview.  Phytomedicine. 2005;  12 305-17.
    CrossrefPubMedGoogle Scholar
  • 13 Kulshreshtha D K, Rastogi R P. Chemical examination of Bacopa monniera. VI. Bacogenin A2. New sapogenin from bacosides.  Phytochemistry. 1974;  13 1205-6.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 15 Rastogi S, Pal R, Kulshreshtha D R. Bacoside A3 - a triterpenoid saponin from Bacopa monniera .  Phytochemistry. 1994;  36 133-7.
    CrossrefPubMedGoogle Scholar
  • 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.
    PubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 19 Garai S, Mahato S B, Ohtani K, Yamasaki K. Dammarane-type triterpenoid saponins from Bacopa monniera .  Phytochemistry. 1996;  42 815-20.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar
  • 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.
    CrossrefPubMedGoogle Scholar

Ikhlas A. Khan

National Center for Natural Products Research

University of Mississippi

University

MS 38677

USA

Phone: +1-662-915-7821

Fax: +1-662-915-7989

Email: ikhan@olemiss.edu

    www.thieme-connect.de/ejournals/toc/plantamedica
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