Identification of major and minor constituents of Harpagophytum procumbens (Devil's claw) using HPLC-SPE-NMR and HPLC-ESIMS/APCIMS

Journal of Natural Products

Volumn 69, Issue 9, 2006, Pages 1280-1288

  Clarkson, Cailean ^a   Stærk, Dan ^a   Hansen, Steen Honoré ^a   Smith, Peter J ^b   Jaroszewski, Jerzy W ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

2' O ACTEOSIDE; 2',6' DI O ACETYLACTEOSIDE; 6' O ACETYLACTEOSIDE; 8 FERULOYLHARPAGIDE; 8(4 COUMAROYL)HARPAGIDE; 8,11,13 TOTARATRIEN 12,13 DIOL; ABIETANE DERIVATIVE; ACTEOSIDE; ALCOHOL; CINNAMIC ACID; DITERPENE; FERRUGINOL; HARPAGIDE; HARPAGOPHYTUM EXTRACT; HARPAGOSIDE; ISOACTEOSIDE; MAYTENOQUINONE; PETROLEUM ETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTROSPRAY; HARPAGOPHYTUM; HARPAGOPHYTUM PROCUMBENS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL DETECTION; SIGNAL NOISE RATIO; STRUCTURE ANALYSIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HARPAGOPHYTUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT ROOTS; PLANTS, MEDICINAL; SOUTH AFRICA;

BETULACEAE; HARPAGOPHYTUM PROCUMBENS;

EID: 33750006304     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0601612     Document Type: Article

References (50)

1. Stewart, K. M.; Cole, D. J. Ethnopharmacol. 2005, 100, 225-236.
2. Watt, J. M.; Breyer-Brandwijk, M. G. The Medicinal and Poisonous Plants of Southern Africa; E. & S. Livingstone Ltd. Publishers: London, 1962; p 830.
3. Van Wyk, B. E.; van Oudtshoorn, B.; Gericke, N. Medicinal Plants of South Africa; Briza Publishers: Pretoria, 1997; p 144.
4. Wegener, T. HerbalGram 2000, 50, 47-54.
5. Barnes, J.; Anderson, L. A.; Phillipson, J. D. Herbal Medicines, 2nd ed.; Pharmaceutical Press: London, 2002; pp 174-180.
6. Chrubasik, S.; Conradt, C.; Roufogalis, B. D. Phytother. Res. 2004, 18, 187-189.
7. Lichti, H.; von Wartburg, A. Helv. Chim. Acta 1966, 49, 1552-1556.
8. Kikuchi, T.; Matsuda, S.; Kubo, Y.; Namba, T. Chem. Pharm. Bull. 1983, 31, 2296-2301.
9. Burger, J. F. W.; Brandt, E. V.; Ferreira, D. Photochemistry 1987, 26, 1453-1457.
10. Clarkson, C.; Campbell, W. E.; Smith, P. J. Planta Med. 2003, 69, 720-724.
11. Boje, K.; Lechtenberg, M.; Nahrstedt, A. Planta Med. 2003, 69, 820-825.
12. Munkombwe, N. M. Phytochemistry 2003, 62, 1231-1234.
13. Seger, C.; Godejohann, M.; Tseng, L. H.; Spraul, M.; Girder, A.; Sturm, S.; Stuppner, H. Anal. Chem. 2005, 77, 878-885.
14. Jaroszewski, J. W. Planta Med. 2005, 71, 691-700.
15. Jaroszewski, J. W. Planta Med. 2005, 71, 795-802.
16. Exarchou, V.; Godejohann, M.; Van Beek, T. A.; Gerothanassis, I. P.; Vervoort, J. Anal. Chem. 2003, 75, 6288-6294.
17. Clarkson, C.; Stærk, D.; Hansen, S. H.; Jaroszewski, J. W. Anal. Chem. 2005, 77, 273-283.
18. Lambert, M.; Stærk, D.; Hansen, S. H.; Sairafianpour, M.; Jaroszewski, J. W. J. Nat. Prod. 2005, 68, 1500-1509.
19. Jaroszewski, J. W. In Magnetic Resonance in Food Science, the Multivariate Challenge; Engelsen, S. B., Belton, P. S., Jacobsen, H. J., Eds.; The Royal Society of Chemistry: London, 2005; pp 39-46.
20. Clarkson, C.; Stærk, D.; Hansen, S. H.; Smith, P. J.; Jaroszewski, J. W. J. Nat. Prod. 2006, 69, 527-530.
21. Cooper, R.; Solomon, P. H.; Kubo, I.; Nakanishi, K.; Shoolery, J. N.; Occolowitz, J. L. J. Am. Chem. Soc. 1980, 102, 7955-7956.
22. Wu, J.; Huang, J.; Xiao, Q.; Zhang, S.; Xiao, Z.; Li, Q.; Long, L.; Huang, L. Magn. Reson. Chem. 2004, 42, 659-662.
23. Miyase, T.; Koizumi, A.; Ueno, A.; Noro, T.; Kuroyanagi, M.; Fukushima, S.; Akiyama, Y.; Takemoto, T. Chem. Pharm. Bull. 1982, 30, 2732-2737.
24. Kobayashi, H.; Karasawa, H.; Miyase, T.; Fukushima, S. Chem. Pharm. Bull. 1984, 32, 3880-3885.
25. Li, Y.; Jiang, S.; Gao, W.; Zhu, D. Phytochemistry 1999, 50, 101-104.
26. Burnell, R. H.; Jean, M.; Marceau, S. Can. J. Chem. 1988, 66, 227-230.
27. Evans, G. B.; Furneaux, R. H. Bioorg. Med. Chem. 2000, 8, 1653-1662.
28. Harrison, L. J.; Asakawa, Y. Phytochemistry 1987, 26, 1211-1212.
29. Fang, J.-M.; Lee, C.-K.; Cheng, Y.-S. Phytochemistry 1993, 33, 1169-1172.
30. Lee, C.-K.; Cheng, Y.-S. J. Nat. Prod. 2001, 64, 511-514.
31. Martin, J. D. Tetrahedron 1973, 29, 2553-2559.
32. Grant, P. K.; Johnson, A. W. J. Chem. Soc. 1957, 4079-4089.
33. Johnson, A. W.; King, T. J.; Martin, R. J. J. Chem. Soc. 1961, 4420-4425.
34. Falshaw, P. C.; King, T. J. J. Chem. Soc., Perkin Trans. I 1983, 1749-1752.
35. Mdee, L. K.; Waibel, R.; Nkunya, M. H. H.; Jonker, S. A.; Achenbach, H. Phytochemistry 1998, 49, 1107-1113.
36. Jiménez-Estrada, M.; Reyes-Chilpa, R.; Hernândez-Ortega, S.; Cristobal-Telésforo, E.; Torres-Colin, L.; Jankowski, C. K.; Aumelas, A.; Van Calsteren, M. R. Can. J. Chem. 2000, 78, 248-254.
37. Alvarenga, N. L.; Ferro, E. A.; Ravelo, A. G.; Kennedy, M. L.; Maestro, M. A.; González, A. G. Tetrahedron 2000, 56, 3771-3774.
38. Jankowski, C. K.; Savoie, A.; Lesage, D.; Boivin, J.; Leclair, G.; Diaz, E. T.; Reyes-Chilpa, R.; Jimenez-Estrada, M.; Barrios, H. Polish J. Chem. 2005, 79, 429-440.
39. Stocking, E. M.; Williams, R.M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115.
40. Onan, K. D.; Kelley, C. J.; Patarapanich, C.; Leary, J. D.; Aladesanmi, A. J. J. Chem. Soc., Chem. Commun. 1985, 121-122.
41. Menash, A. Y.; Houghton, P. J.; Bloomfield, S.; Vlietnick, A.; Berghe, D. V. J. Nat. Prod. 2000, 63, 1210-1213.
42. Damtoft, S.; Franzyk, H.; Jensen, S. R.; Nielsen, B. J. Phytochemistry 1993, 34, 239-243.
43. Sandvoss, M.; Bardsley, B.; Beck, T. L.; Lee-Smith, E.; North, S. E.; Moore, P. J.; Edwards, A. J.; Smith, R. J. Magn. Reson. Chem. 2005, 43, 762-770.
44. Czygan, F. C.; Kruger, A.; Schier, W.; Volk, O. Deutsch. Apoth. Ztg. 1977, 117, 1431-1434.
45. Ziller, K.; Franz, G. Planta Med. 1979, 37, 340-348.
46. Eich, J.; Schmidt, M.; Betti, G. Pharm. Pharmacol. Lett. 1998, 8, 75-78.
47. Levielle, G.; Wilson, G. Plant Cells Rep. 2002, 21, 220-225.
48. Guillerault, L.; Ollivier, E.; Elias, R.; Balansard, G. J. Liq. Chrom. 1994, 17, 2951-2960.
49. Sticher, O.; Meier, B. D. Deutsch. Apoth. Ztg. 1980, 120, 1592-1594.
50. Tunmann, P.; Bauersfeld, H. J. Arch. Pharm. 1975, 308, 655-657.