Quantitative analysis of anti-inflammatory and radical scavenging triterpenoid esters in evening primrose seeds

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 18, 2006, Pages 6623-6628

  Zaugg, Janine ^a   Potterat, Olivier ^a   Plescher, Andreas ^b   Honermeier, Bernd ^c   Hamburger, Matthias ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b Pharmaplant GmbH   (Germany)

^c JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Accelerated solvent extraction; Anti inflammatory; Caffeoyl ester; Evening primrose oil; HPLC; Oenothera ammophila; Oenothera biennis; Oenothera lamarckiana; Onagraceae; Pressurized liquid extraction; Radical scavenger; Triterpenoid

Indexed keywords

ANTIINFLAMMATORY AGENT; ESTER; SCAVENGER; TRITERPENE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; EVENING PRIMROSE; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PLANT SEED;

ANTI-INFLAMMATORY AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; FREE RADICAL SCAVENGERS; OENOTHERA BIENNIS; SEEDS; TRITERPENES;

OENOTHERA; OENOTHERA AMMOPHILA; OENOTHERA BIENNIS; OENOTHERA LAMARCKIANA; ONAGRACEAE; PRIMULA;

EID: 33748887219     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0611466     Document Type: Article

References (36)

1. Hudson, B. J. F. Evening primrose (Oenothera ssp.) oil and seed. J. Am. Oil Chem. Soc. 1984, 61, 540-543.
2. Arnold, L. E.; Kleykamp, D.; Votolato, N. A.; Taylor, W. A.; Kontras, S. B.; Tobin, K. Gamma-linolenic acid for attention-deficit hyperactivity disorder: Placebo-controlled comparison to D-amphetamine. Biol. Psychiatry 1989, 25, 222-228.
3. Brzeski, M.; Madhok, R.; Capell, H. Evening primrose oil in patients with rheumatoid-arthritis and side-effects of nonsteroidal antiinflammatory drugs. Br. J. Dermatol. 1991, 30, 370-372.
4. Schafer, L.; Kragballe, K. Supplementation with evening primrose oil in atopic dermatitis: Effect on fatty acids in neutrophils and epidermis. Lipids 1991, 26, 557-560.
5. Cerin, A.; Collins, A.; Landgren, B. M.; Eneroth, P. Hormonal and biochemical profiles of premenstrual syndrome. Treatment with essential fatty acids. Acta Obstet. Gynecol. Scand. 1993, 72, 337-343.
6. Berth-Jones, J.; Graham-Brown, R. A. Placebo-controlled trial of essential fatty acid supplementation in atopic dermatitis. Lancet 1993, 341, 1557-1560.
7. Biagi, P. L.; Bordoni, A.; Hrelia, S.; Celadon, M.; Ricci, G. P.; Cannella, V.; Patrizi, A.; Specchia, F.; Masi, M. The effect of gamma-linolenic acid on clinical status, red cell fatty acid composition and membrane microviscosity in infants with atopic dermatitis. Drugs Exp. Clin. Res. 1994, 20, 77-84.
8. Kleijnen, J. Evening primrose oil. Br. Med. J. 1994, 309, 824-825.
9. Hederos, C. A.; Berg, A. Epogam evening primrose oil treatment in atopic dermatitis and asthma. Arch. Dis. Child 1996, 75, 494-497.
10. Yoshimoto-Furuie, K.; Yoshimoto, K.; Tanaka, T.; Saima, S.; Kikuchi, Y.; Shai, J.; Horrobin, D. F.; Echizen, H. Effects of oral supplementation with evening primrose oil for six weeks on plasma essential fatty acids and uremic skin symptoms in hemodialysis patients. Nephron 1999, 81, 151-159.
11. Belch, J. J. F.; Hill, A. Evening primrose oil and borage oil in rheumatologic conditions. Am. J. Clin. Nutr. 2000, 71, 652S-356S.
12. Mahady, G. B.; Fong, H. H. S.; Farnsworth, N. R. Botanical Dietary Supplements: Quality, Safety and Efficacy; Swets and Zeitlinger: Lisse, The Netherlands, 2001; pp 75-85.
13. Barre, D. E. Potential of evening primrose, borage, black currant, or fungal oils in human health. Ann. Nutr. Metab. 2001, 45, 47-57.
14. Takwale, A.; Tan, E.; Agarwal, S.; Barclay, G.; Ahmed, I.; Hotchkiss, K.; Thompson, J. R.; Chapman, T.; Berth-Jones, J. Efficacy and tolerability of borage oil in adults and children with atopic eczema: Randomised, double blind, placebo controlled, parallel group trial. Br. Med. J. 2003, 327, 1385.
15. Engler, M. M. Comparative study of diets enriched with evening primrose, black currant, borage or fungal oils on blood pressure and pressor responses in spontaneously hypertensive rats. Prostaglandins, Leukotrienes Essent. Fatty Acids 1993, 49, 809-814.
16. Dines, K. C.; Cotter, M. A.; Cameron, N. E. Effectiveness of natural oils as sources of γ-linolenic acid to correct peripheral nerve conduction velocity abnormalities in diabetic rats: modulation by thromboxane A2 inhibition. Prostaglandins, Leukotrienes Essent. Fatty Acids 1996, 55, 159-165.
17. Ziboh, V. A.; Chapkin, R. S. Biological significance of polyunsaturated fatty acids in the skin. Arch. Dermatol. 1987, 123, 1686-1690.
18. Ziboh, V. A.; Miller, C. C.; Cho, Y. Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: Generation of antiinflammatory and antiproliferative metabolites. Am. J. Clin. Nutr. 2000, 71, 361S-366S.
19. Danz, H.; Stoyanova, S.; Wippich, P.; Brattström, A.; Hamburger, M. Identification and isolation of the xyclooxygenase-2 inhibitory principle in Isatis tinctoria. Planta Med. 2001, 67, 411-416.
20. Danz, H.; Stoyanova, S.; Thomet, O. A. S.; Simon, H. U.; Dannhardt, G.; Ulbrich, H.; Hamburger, M. Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis. Planta Med. 2002, 68, 875-880.
21. Dittmann, K.; Gerhäuser, C.; Klimo, K.; Hamburger, M. HPLC-based activity profiling of Salvia miltiorrhiza for MAO A and iNOS inhibitory activities. Planta Med. 2004, 70, 909-913.
22. Oberthür, C.; Jäggi, R.; Hamburger, M. HPLC based activity profiling for 5-lipoxygenase inhibitory activity in Isatis tinctoria leaf extracts. Fitoterapia 2005, 76, 324-332.
23. Hu, F.; Schmidt, K.; Stoyanova, S.; Li, Z.; Gräfe, U.; Hamburger, M. Radical scavengers from the entomogenous Deuteromycete Beauveria amorpha. Planta Med. 2002, 68, 64-65.
24. Hamburger, M.; Riese, U.; Graf, H.; et al. Constituents in evening primrose oil with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities. J. Agric. Food Chem. 2002, 50, 5533-5538.
25. Vane, J. R.; Bakhle, Y. S.; Botting, R. M. Cyclooxygenases 1 and 2. Annu. Rev. Pharmacol. Toxicol. 1998, 38, 97-120.
26. Bieth, J. G. Leucocyte elastase. In Handbook of Proteolytic Enzymes; Barrett, A. J., Rawlings, N. D., Woessner, F. F., Eds.; Academic Press: London, United Kingdom, 1998; pp 54-60.
27. Knorr, R.; Hamburger, M. Quantitative analysis of anti-inflammatory and radical scavenging triterpenoid esters in evening primrose oil. J. Agric. Food Chem. 2004, 52, 3319-3324.
28. Benthin, B.; Danz, H.; Hamburger, M. Pressurized liquid extraction of medicinal plants. J. Chromatogr. A 1999, 837, 211-219.
29. Danz, H.; Baumann, D.; Hamburger, M. Quantitative determination of the dual COX-2/5-LOX inhibitor tryptanthrin in Isatis tintoria by ESI-LC-MS. Planta Med. 2002, 68, 152-157.
30. Kaufmann, B.; Christen, P. Recent extraction techniques for natural products: Microwave-assisted extraction and pressurized solvent extraction. Phytochem. Anal. 2002, 13, 105-113.
31. Oberthür, C.; Graf, H.; Hamburger, M. The content of indigo precursors in Isatis tinctoria leaves - A comparative study of selected accessions and post-harvest treatments. Phytochemistry 2004, 65, 3261-3268.
32. Basalo, C.; Mohn, T.; Hamburger, M. Are extraction methods in quantitative assays of pharmacopoeia monographs exhaustive? A comparison with pressurized liquid extraction. Planta Med. In press.
33. Camel, V. Recent extraction techniques for solid matrices - Supercritical fluid extraction, pressurized fluid extraction and microwave-assisted extraction: Their potential and pitfalls. Analyst 2001, 126, 1182-1193.
34. Hamburger, M.; Baumann, D.; Adler, S. Supercritical carbon dioxide extraction of selected medicinal plants - Effects of high pressure and added ethanol on yield of extracted substances. Phytochem. Anal. 2004, 15, 46-54.
35. Frankel, E. N. Antioxidants in lipid foods and their impact on food quality. Food Chem. 1996, 57, 51-55.
36. Owen, R. W.; Giacosa, A.; Hull, W. E.; et al. Olive-oil consumption and health: The possible role of antioxidants. Lancet Oncol. 2000, 1, 107-112.