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Planta Med 2007; 73(6): 578-584
DOI: 10.1055/s-2007-967187
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

HPLC-SPE-NMR Characterization of Sesquiterpenes in an Antimycobacterial Fraction from Warburgia salutaris

Cailean Clarkson1 , Eliya V. Madikane2 , 3 , Steen Honoré Hansen4 , Peter J. Smith2 , Jerzy W. Jaroszewski1
  • 1Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Copenhagen, Denmark
  • 2Department of Medicine, University of Cape Town, Cape Town, South Africa
  • 3Department of Pharmacology, University of Oxford, Oxford, United Kingdom
  • 4Department of Pharmaceutics and Analytical Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Copenhagen, Denmark
Further Information

Publication History

Received: January 15, 2007 Revised: March 21, 2007

Accepted: March 24, 2007

Publication Date:
07 May 2007 (online)

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Abstract

HPLC-SPE-NMR analysis of a chemically complex antimycobacterial fraction of Warburgia salutaris allowed the rapid identification of seven new and four known drimane- and coloratane-type sesquiterpenes. This recently introduced hyphenated technique is therefore a highly valuable tool for elucidation of the chemistry of biologically active fractions of natural origin.

Key words

Warburgia salutaris - Canellaceae - HPLC-SPE-NMR - sesquiterpenoids - drimanes - coloratanes - mycobacteria

References

  • 1 Newman D J, Cragg G M, Snader K M. Natural products as sources of new drugs over the period 1981 - 2002.  J Nat Prod. 2003;  66 1022-37.
    CrossrefPubMedSearch in Google Scholar
  • 2 Koehn F E, Carter G T. The evolving role of natural products in drug discovery.  Nat Rev Drug Discov. 2005;  4 206-20.
    CrossrefPubMedSearch in Google Scholar
  • 3 Butler M S. Natural products to drugs: natural product derived compounds in clinical trials.  Nat Prod Rep. 2005;  22 162-95.
    CrossrefPubMedSearch in Google Scholar
  • 4 Rabe T, van Staden J. Isolation of an antibacterial sesquiterpenoid from Warburgia salutaris .  J Ethnopharmacol. 2000;  73 171-4.
    CrossrefPubMedSearch in Google Scholar
  • 5 Wube A A, Bucar F, Gibbons S, Asres K. Sesquiterpenes from Warburgia ugandensis and their antimycobacterial acitivity.  Phytochemistry. 2005;  66 2309-15.
    CrossrefPubMedSearch in Google Scholar
  • 6 Jansen B JM, de Groot A. Occurrence, biological acitivity and synthesis of drimane sesquiterpenoids.  Nat Prod Rep. 2004;  21 449-77.
    CrossrefPubMedSearch in Google Scholar
  • 7 Madikane E V, Bhakta S, Smith P J, Sim E. Arylamine N-acetyltransferase (NAT) is a target for Warburgia salutaris extract showing anti-mycobacterial activity. New Delhi, India; International Symposium on Emerging Trends in Tuberculosis Research 2004.
    Search in Google Scholar
  • 8 Madikane E V, Bhakta S, Russell A J, Campbell W B, Claridge T DW, Elisha G B. et al . Inhibition of mycobacterial arylamine N-acetylytransferase contributes to antimycobacterial activity of Warburgia salutaris .  Bioorg Med. 2007;  15 3579-86.
    PubMedSearch in Google Scholar
  • 9 Jaroszewski J W. Hyphenated NMR methods in natural products research, part 2: HPLC-SPE-NMR and other new trends in NMR hyphenation.  Planta Med. 2005;  71 795-802.
    Thieme ConnectPubMedSearch in Google Scholar
  • 10 Seger C, Godejohann M, Tseng L, Spraul M, Girtler A, Sturm S. et al . HPLC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: Identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens .  Anal Chem. 2005;  77 878-85.
    CrossrefPubMedSearch in Google Scholar
  • 11 Lambert M, Stærk D, Hansen S H, Sairafianpour M, Jaroszewski J W. Rapid extract dereplication using HPLC-SPE-NMR: Analysis of isoflavonoids from Smirnowia iranica .  J Nat Prod. 2005;  68 1500-9.
    CrossrefPubMedSearch in Google Scholar
  • 12 Clarkson C, Stærk D, Smith P J, Jaroszewski J W. Discovering new natural products directly from crude extracts by HPLC-SPE-NMR: Chinane diterpenes in Harpagophytum procumbens .  J Nat Prod. 2006;  69 527-30.
    CrossrefPubMedSearch in Google Scholar
  • 13 Clarkson C, Stærk D, Hansen S H, Smith P J, Jaroszewski J W. Identification of major and minor constituents of Harpagophytum procumbens (Devil's Claw) using HPLC-SPE-NMR and HPLC-ESIMS/APCIMS.  J Nat Prod. 2006;  69 1280-8.
    CrossrefPubMedSearch in Google Scholar
  • 14 Clarkson C, Stærk D, Hansen S H, Jaroszewski J W. Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: Application of HPLC-DAD-SPE-NMR to identification of constituents of Kanahia laniflora .  Anal Chem. 2005;  77 3547-53.
    CrossrefPubMedSearch in Google Scholar
  • 15 Brooks C JW, Draffan G H. Sesquiterpenoids of Warburgia species II: Ugandensolide and ugandensidial (cinnamodial).  Tetrahedron. 1969;  25 2887-98.
    CrossrefPubMedSearch in Google Scholar
  • 16 Kioy D, Gray A I, Waterman P G. A comparative study of the stem-bark drimane sesquiterpenes and leaf volatile oils of Warburgia ugandensis and W. stuhlmannii .  Phytochemistry. 1990;  29 3535-8.
    CrossrefPubMedSearch in Google Scholar
  • 17 Canonica L, Corbella A, Jommi G, Krepinsky J, Ferrari G, Casagrande C. Structure of cinnamolide , cinnamosmolide, and cinnamodial sesquiterpenes with drimane skeleton from Cinnamosma fragrans .  Tetrahedron Lett. 1967;  23 2137-41.
    PubMedSearch in Google Scholar
  • 18 Kubo I, Matsumoto T, Kakooko A B, Mubiru N K. Structure of mukaadial, a molluscicide from the Warburgia plants.  Chem Lett. 1983;  7 979-80.
    PubMedSearch in Google Scholar
  • 19 Mashimbye M J, Maumela M C, Drewes S E. A drimane sesquiterpenoid lactone from Warburgia salutaris .  Phytochemistry. 1999;  51 435-8.
    CrossrefPubMedSearch in Google Scholar
  • 20 Manguro L OA, Ugi I, Hermann R, Lemmen P. Flavonol and drimane-type sesquiterpenes glycosides of Warburgia stuhlmannii leaves.  Phytochemsitry. 2003;  63 497-502.
    PubMedSearch in Google Scholar
  • 21 Rajab M S, Ndegwa J M. 11α-Hydroxymuzigadiolide, a novel drimane sesquiterpene from the stem bark of Warburgia ugandensis .  Bull Chem Soc Ethiopia. 2000;  14 45-9.
    PubMedSearch in Google Scholar
  • 22 Montagnac A, Martin M T, Debitus C, Païs M. Drimane sesquiterpenes from sponge Dysidea fusca .  J Nat Prod. 1996;  59 866-8.
    CrossrefPubMedSearch in Google Scholar
  • 23 Taniguchi M, Adaci T, Oi S, Kimura A, Katsumura S, Isoe S. et al . Structure-activity relationship of the Warburgia sesquiterpene dialdehydes.  Agric Biol Chem. 1984;  48 73-8.
    PubMedSearch in Google Scholar

Prof. Jerzy W. Jaroszewski

Department of Medicinal Chemistry

Faculty of Pharmaceutical Sciences

University of Copenhagen

Universitetsparken 2

2100 Copenhagen

Denmark

Fax: +45-3530-6040

Email: jj@farma.ku.dk