Planta Med 2007; 73(3): 296-297
DOI: 10.1055/s-2007-967124
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Anthelmintic Activity of Aporphine Alkaloids from Cissampelos capensis

Sloan Ayers1 , Deborah L. Zink1 , Kenneth Mohn2 , Joanne Staats Powell2 , Christine M. Brown2 , Terry Murphy2 , Robert Brand3 , Seef Pretorius4 , Dennis Stevenson3 , Donald Thompson2 , Sheo B. Singh1
  • 1Natural Products Chemistry, Merck Research Laboratories, Rahway, NJ, USA
  • 2Merck and Co., Inc., Branchburg Farm, Somerville, NJ, USA
  • 3The New York Botanical Garden, Bronx, NY, USA
  • 4University of the Free State, Bloemfontein, South Africa
Further Information

Publication History

Received: November 30, 2006

Accepted: January 20, 2007

Publication Date:
16 February 2007 (online)

Abstract

Two known aporphine alkaloids, (S)-dicentrine (1) and (S)-neolitsine (2), have been isolated from the MeOH extract of the aerial parts of Cissampelos capensis (Menispermaceae). The structures of these compounds were elucidated by NMR and MS analysis and comparison to literature data. These compounds were isolated by bioassay-guided fractionation using the Haemonchus contortus larval development assay. Compounds 1 and 2 exhibited EC90 values (concentration at which 90 % loss of larval motility is observed) of 6.3 and 6.4 μg/mL, respectively. In an in vivo assay, administration of 1 resulted in 67 % reduction of worm counts in mice at 25 mg/kg when dosed orally.

References

  • 1 McKellar Q A, Jackson F. Veterinary anthelmintics: old and new.  Trends Parasitol. 2004;  20 456-61.
  • 2 Michael B, Meinke P T, Shoop W. Comparison of ivermectin, doramectin, selamectin, and eleven intermediates in a nematode larval development assay.  J Parasitol. 2001;  87 692-6.
  • 3 Fonseca-Salamanca F, Martinez-Grueiro M M, Martinez-Fernandez A R. Nematocidal activity of nitazoxanide in laboratory models.  Parasitol Res. 2003;  91 321-4.
  • 4 Ma W, Fukushi Y, Tahara S, Osawa T. Fungitoxic alkaloids from Hokkaido Papaveraceae.  Fitoterapia. 2000;  71 527-34.
  • 5 Taylor E C, Andrade J G, Rall G JH, McKillop A. Thallium in Organic Synthesis. 59. Alkaloid synthesis via intramolecular nonphenolic oxidative coupling. Preparation of (±)-ocoteine, (±)-acetoxyocoxylonine, (±)-3-methoxy-N-acetylnornantenine, (±)-neolitsine, (±)-kreysigine, (±)-O-methylkreysigine, and (±)-multifloramine.  J Am Chem Soc. 1980;  102 6513-9.
  • 6 Ringdahl B, Chan R PK, Craig J C. Circular dichroism of aporphines.  J Nat Prod. 1981;  44 80-5.
  • 7 Stévigny C, Block S, De Pauw-Gillet M C, de Hoffmann E, Llabrès G, Adjakidjé V. et al . Cytotoxic aporphine alkaloids from Cassytha filiformis .  Planta Med. 2002;  68 1042-4.

Dr. Sheo B. Singh

Natural Products Chemistry

Merck Research Laboratories

P.O. Box 2000

Rahway

NJ 07065

USA

Phone: +1-732-594-3222

Fax: +1-732-594-6880

Email: sheo_singh@merck.com

    >