RSS-Feed abonnieren
DOI: 10.1055/s-2007-967187
© Georg Thieme Verlag KG Stuttgart · New York
HPLC-SPE-NMR Characterization of Sesquiterpenes in an Antimycobacterial Fraction from Warburgia salutaris
Publikationsverlauf
Received: January 15, 2007
Revised: March 21, 2007
Accepted: March 24, 2007
Publikationsdatum:
07. Mai 2007 (online)
![](https://www.thieme-connect.de/media/plantamedica/200706/lookinside/thumbnails/10.1055-s-2007-967187-1.jpg)
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.
- 2 Koehn F E, Carter G T. The evolving role of natural products in drug discovery. Nat Rev Drug Discov. 2005; 4 206-20.
- 3 Butler M S. Natural products to drugs: natural product derived compounds in clinical trials. Nat Prod Rep. 2005; 22 162-95.
- 4 Rabe T, van Staden J. Isolation of an antibacterial sesquiterpenoid from Warburgia salutaris . J Ethnopharmacol. 2000; 73 171-4.
- 5 Wube A A, Bucar F, Gibbons S, Asres K. Sesquiterpenes from Warburgia ugandensis and their antimycobacterial acitivity. Phytochemistry. 2005; 66 2309-15.
- 6 Jansen B JM, de Groot A. Occurrence, biological acitivity and synthesis of drimane sesquiterpenoids. Nat Prod Rep. 2004; 21 449-77.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 15 Brooks C JW, Draffan G H. Sesquiterpenoids of Warburgia species II: Ugandensolide and ugandensidial (cinnamodial). Tetrahedron. 1969; 25 2887-98.
- 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.
- 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.
- 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.
- 19 Mashimbye M J, Maumela M C, Drewes S E. A drimane sesquiterpenoid lactone from Warburgia salutaris . Phytochemistry. 1999; 51 435-8.
- 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.
- 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.
- 22 Montagnac A, Martin M T, Debitus C, Païs M. Drimane sesquiterpenes from sponge Dysidea fusca . J Nat Prod. 1996; 59 866-8.
- 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.
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