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Cyclooxygenase and 5-Lipoxygenase as Targets for Medicinal Plant Research

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Bioassay Methods in Natural Product Research and Drug Development

Part of the book series: Proceedings of the Phytochemical Society of Europe ((PPSE,volume 43))

Abstract

The incidence of inflammatory diseases in the field of rheumatism, allergies and asthma is increasing. 5 % of the world’s population is suffering from asthma. About 10 % of the children are said to have asthmoid disorders. In the U.S.A., 5.000 people die from asthma per year. In Germany it is 1 lethal case within 100.000 inhabitants per year. In Germany, also one sixth of the population is suffering from rheumatism. Out of them, 1.2 million have chronic polyarthritis. Therefore, there is a real need for new and better anti-inflammatory drugs and concepts.

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References

  1. Samuelsson, B.: Leukotrienes and other lipoxygenase products, Prog. Lipid Res. 25 (1986), 13–18.

    Article  CAS  Google Scholar 

  2. Vane J.R. and Botting R.M. Inflammation and the mechanism of action of anti-inflammatory drugs FASEB J. 1 1987), 89–9

    CAS  Google Scholar 

  3. Smith, W.L. and Marnett, L.J.: Prostaglandin endoperoxide synthase: structure and catalysis, Biochim. Biophys. Acta 1083 (1991), 1–17.

    Article  CAS  Google Scholar 

  4. Vane, J.R. and Botting, R.M.: The mode of action of anti-inflammatory drugs, Postgrad. Med. J. 66Suppl. 4,(1990), S2–S17.

    CAS  Google Scholar 

  5. Sirois, J. and Richards, J.S.: Purification and characterization of a novel, distinct isoform of prostaglandin endoperoxide synthase induced by human chorionic gonadotropin in granulosa cells of rat preovulatory follicles, J. Biol. Chem. 267 (1992), 6382–6388.

    CAS  Google Scholar 

  6. Hla, T. and Neilson, K.: Human cyclooxygenase-2 cDNA. Proc. Natl. Acad. Sci USA 89 (1992), 7384–7388.

    Article  CAS  Google Scholar 

  7. Herschmann, H.R.: Prostaglandin synthase 2, Biochim Biophys Acta 1299 (1996), 125–140.

    Article  Google Scholar 

  8. Xie W., Robertson, D.L., and Simmons, D.L.: Mitogen-inducible prostaglandin G/H synthase: A novel target for nonsteroidal antiinflammatory drugs, Drug Dev. Res. 25 (1992), 249–265.

    Article  CAS  Google Scholar 

  9. Gierse, J.K., McDonald, J.J., Hauser, S.D., Rangwala, S.H., Koboldt, CM., and Seibert, K.: A single amino acid difference between cyclooxygenase-1 (COX-1) and-2 (COX-2) reverses the selectivity of COX-2 specific inhibitors, J. Biol. Chem. 271 (1996), 15810–15814.

    Article  CAS  Google Scholar 

  10. Herrmann, F, Lindemann A., Gauss J., and Mertelsmann, R.: Cytokine-stimulation of prostaglandin synthesis from endogenous and exogenous arachidonic acids in polymor-phonuclear leukocytes involving activation and new synthesis of cyclooxygenase. Eur. J. Immunol 20 (1990), 2513–25

    Article  CAS  Google Scholar 

  11. Funk, C.D., Funk, L.B., Kennedy, M.E., Pong, A.S., and Fitzgerald, G.A.: Human platelet/erythroleukemia cell prostaglandin G/H synthase: cDNA cloning, expression, and gene chromosomal assignment, FASEB J. 5 (1991), 2304–2312.

    CAS  Google Scholar 

  12. Harris, R.C, McKanna, J.A., Akai Y., Jacobson, H.R., Dubois, R.N., and Breyer, M.D.: Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with salt restriction, J. Clin. Invest. 94 (1994), 2504–2510.

    Article  CAS  Google Scholar 

  13. Pugliese, F. and Cinotti, G.A.: Nonsteroidal anti-inflammatory drugs (NSAIDs) and the kidney, Nephrol. Dial. Transplant. 12 (1997), 386–3

    Article  CAS  Google Scholar 

  14. Komhoff M., Grone, H.J., Klein T., Seyberth, H.W., and Nusing, R.M.: Localization of cyclooxygenase-1 and-2 in adult and fetal human kidney: implication for renal function, Am. J. Physiol. 272 (1997), F460–468.

    Google Scholar 

  15. Vane, J.R. and Botting, R.M.: New insights into the mode of action of anti-inflammatory drugs, Inflamm. Res. 44 (1995), 1–10.

    Article  CAS  Google Scholar 

  16. Klein T., Nüsing, R.M., Pfeilschifter J., and Ullrich, V.: Selective inhibition of cyclooxygenase 2. Biochem. Pharmacol. 48 1994), 1605–1

    Article  CAS  Google Scholar 

  17. Mitchell, J.A., Akarasereenont P., Thiemermann, C, Flower, R.J., and Vane, J.R.: Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase, Proc. Natl. Acad. Sci. USA 90(1993), 11693–1169

    Article  CAS  Google Scholar 

  18. Copeland, RA., Williams, JM., Giannaras J., Nurnberg S., Covington M., Pinto D., Pick S., and Trzaskos, JM.: Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase, Proc. Natl. Acad. Sci. USA 91 (1994), 11202–11206.

    Article  CAS  Google Scholar 

  19. Pauwels, R.A., Joos, G.F., and Kips, J.C.: Leukotrienes as therapeutic target for asthma, Allergy 50 (1995), 615–622.

    Article  CAS  Google Scholar 

  20. Ford-Hutchinson, A.W.: Regulation of leukotriene biosynthesis, Cane. Metastasis Rev. 13 (1994), 257–267.

    Article  CAS  Google Scholar 

  21. Wenzel, S.E.: Arachidonic acid metabolites: mediators of inflammation in asthma, Pharmacotherapy. 17 (1997), 3S–12S.

    CAS  Google Scholar 

  22. Ford-Hutchinson, A.W.: Leukotrienes B4 in inflammation, Crit. Rev. Immunol. 10 (1990), 1–12.

    CAS  Google Scholar 

  23. Mayatepek, E. and Hoffmann, G.R: Leukotrienes: biosynthesis, metabolism, and pathophysiologic significance, Pediatr. Res. 37(1995), 1–9.

    Article  CAS  Google Scholar 

  24. Laufer, S.A., Augustin J., Dannhardt G., and Kiefer, W.: (6,7-Diaryldihydropyrrolizin-5-yl)acetic acids, a novel class of potent dual inhibitors of both cyclooxygenase and 5-lipoxygenase, J. Med. Chem. 37 (1994), 1894–1897.

    Article  CAS  Google Scholar 

  25. Davidson, F.F., Dennis, E.A., Powell M., and Glenney, J.R.jr: Inhibition of phospholipase A2 by ‘lipocortins’ and calpactins. An effect of binding to substrate phospholipids, J. Biol. Chem. 262 (1987), 1698–1705.

    CAS  Google Scholar 

  26. Kujubu, D.A. and Herschman, H.R.: Dexamethasone inhibits mitogen induction of the TIS10 prostaglandin synthase/cyclooxygenase gene, J. Biol. Chem. 267 (1992), 7991–7994.

    CAS  Google Scholar 

  27. Mantri, P. and Wittiak, D.T.: Inhibitors of cyclooxygenase and 5-lipoxygenase, Curr. Med. Chem. 1 (1994), 328–355.

    CAS  Google Scholar 

  28. Smith, L.J.: Leukotrienes in asthma. The potential therapeutic role of antileukotriene agents, Arch. Intern. Med. 156 (1996), 2181–2189.

    Article  CAS  Google Scholar 

  29. Harris, R.R., Carter, G.W., Bell, R.L., Moore, J.L., and Brooks, D.W.: Clinical activity of leukotriene inhibitors, Int. J. Immunopharmacol. 17 (1995), 147–156.

    Article  CAS  Google Scholar 

  30. Wenzel, S.E. and Kamada, A.K.: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma, Ann. Pharmacother. 30 (1996) 858–864.

    CAS  Google Scholar 

  31. Ford-Hutchinson, A.W.: FLAP: a novel drug target for inhibiting the synthesis of leukotrienes, Trends Pharmacol. Sci. 12 (1991), 68–70.

    Article  CAS  Google Scholar 

  32. Uematsu T., Kanamaru M., Kosuge K., Hara K., Uchiyama N., Takenaga N., Tanaka W., Friedman, BS., and Nakashima, M.: Pharmacokinetic and pharmacodynamic analysis of a novel leukotriene biosynthesis inhibitor, MK-0591, in healthy volunteers, Br. J. Clin. Pharmacol. 40 (1995), 59–66.

    Article  CAS  Google Scholar 

  33. Hatzelmann A., Goossens J., Fruchtmann R., Mohrs, K.H., Raddatz S., and Müller-Peddinghaus, R.: Inversely-correlated inhibition of human 5-lipoxygenase activity by BAY X1005 and other quinoline derivatives in intact cells and a cell-free system implications for the function of 5-lipoxygenase activating protein, Biochem. Pharmacol. 47 (1994), 2259–2268.

    Article  CAS  Google Scholar 

  34. Mancini, J.A., Prasit P., Coppolino, M.G., Charleson P., Leger S., Evans, J.R, Gillard, J.W., and Vickers, P.J.: 5-Lipoxygenase-activating protein is the target of a novel hybrid of two classes of leukotriene bioxynthesis inhibitors, Molecular Pharmacol. 41 (1992), 267–272.

    CAS  Google Scholar 

  35. Sorkness, C. A.: The use of 5-lipoxygenase inhibitors and leukotriene receptor antagonists in the treatment of chronic asthma, Pharmacotherapy. 17 (1997), 50S–54S.

    CAS  Google Scholar 

  36. Weithmann, K.U.: Constitutive and inducible cellular arachidonic acid metabolism in vitro, in: H.G. Vogel and W.H. Vogel: Drug Discovery and Evaluation, Springer Verlag, Berlin, Heidelberg, 1997.

    Google Scholar 

  37. Harvey, J. and Osborne, D.J.: A rapid method for detecting inhibitors of both cyclo-oxygenase and lipoxygenase metabolites of arachidonic acid, J. Pharmacol. Meth. 9 (1983), 147–155.

    Article  CAS  Google Scholar 

  38. Van der Ouderaa, F.J. and Buytenhek, M: Purification of PGH synthase from sheep vesicular glands, Methods Enzymol. 86 (1982), 60–68.

    Article  Google Scholar 

  39. Van der Ouderaa, F.J., Buytenhek M., Nugteren, D.H., and Van Dorp, D.A.: Purification and characterisation of prostaglandin endoperoxide synthetase from sheep vesicular glands, Biochim. Biophys. Acta 487 (1977), 315–331.

    Article  Google Scholar 

  40. White, H.L. and Glassman, A.T.: A simple radiochemical assay for prostaglandin synthetase, Prostaglandins 7 (1974) 123–129.

    Article  CAS  Google Scholar 

  41. Pongprayoon U., Baeckstrom P., Jacobsson U., Lindstrom M., and Bohlin, L.: Compounds inhibiting prostaglandin synthesis isolated from Ipomoea pes-caprae, Planta Med. 57 (1991), 515–518.

    Article  CAS  Google Scholar 

  42. Freyberger A. Schnitzler R. Schiffmann D. and Degen G.H. Prostaglandin-H-synthase competent cells derived from ram seminal vesicles a tool for studying cooxidation of xebiotics Mol. Toxicol. 1 1987-88 503–512

    Google Scholar 

  43. Dannhardt G., Bauer A., and Nowe, U.: Non-steroidal anti-inflammatory agents, Part 24. Pyrrolidino enaminones as models to mimic arachidonic acid, Arch. Pharm. Weinheim. 330 (1997), 74–82.

    Article  CAS  Google Scholar 

  44. Boopathy, R. and Balasubramanian, A.S.: Purification and characterization of sheep platelet cyclo-oxygenase, Biochem. J. 239 (1986), 371–377.

    CAS  Google Scholar 

  45. Dragan, Y.P. and Ellis, E.F.: Optimization of an assay for studying the effects of agents on cyclooxygenase and lipoxygenase metabolism of arachidonic acid in washed human platelets, Prostaglandins Leukot. Essent. Fatty Acids 39 (1990), 105–109.

    Article  CAS  Google Scholar 

  46. Johnson, J.L., Wimsatt J., Buckel. S.D., Dyer, R.D., and Maddipati, K.R.: Purification and characterization of prostaglandin-H synthase from sheep placental cotyledons, Arch. Biochem. Biophys. 324 (1995), 26–34.

    Article  CAS  Google Scholar 

  47. Brideau C., Kargman S., Liu S., Dallob, A.L., Ehrich, E.W., Rodger, I.W., and Chan, C.C.: A human whole blood assay for clinical evaluation of biochemical efficacy of cyclooxygenase inhibitors, Inflamm. Res. 45(1996), 68–74.

    Article  CAS  Google Scholar 

  48. Cromlish, W.A. and Kennedy, B.P.: Selective inhibition of cyclooxygenase-1 and-2 using intact insect cell assays, Biochem. Pharmacol. 52 (1996), 1777–1785.

    Article  CAS  Google Scholar 

  49. Ringbom T., Noreen Y., Perera P., and Bohlin, L.: Development of a COX-1 and COX-2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis, J. Nat. Prod. (1997) atin press.

    Google Scholar 

  50. Wagner H., Wierer M., and Bauer, R.: In vitro-Hemmung der Prostaglandin-Biosynthese durch etherische Öle und phenolische Verbindungen, Planta Med. 52 (1986), 184–188.

    Article  Google Scholar 

  51. Weithmann, K.U., Jeske S., and Schlotte, V: Effect of leflunomide on constitutive and inducible pathways of cellular eicosanoid generation, Agents Actions 41 (1994), 164–170.

    Article  CAS  Google Scholar 

  52. Redl K., Breu W., Davis B., and Bauer, R.: Antiinflammatory active polyacetylenes from Bidens campylotheca, Planta Med. 60 (1994), 58–62.

    Article  CAS  Google Scholar 

  53. Pradelles P., Grassi J., and Maclouf, J.: Enzyme immunoassays of eicosanoids using acetylcholine esterase as label: an alternative to radioimmunoassay, Anal. Chem. 57 (1985), 1170–1173.

    Article  CAS  Google Scholar 

  54. Maclouf J., Grassi, J. and Pradelles, P.: Development of enzyme-immunoassay techniques for the measurement of eicosanoids, Prostagl. Lipid Met. Rad. Inj. (1987), 355–36

    Google Scholar 

  55. Scioscia, K.A., Snyderman, C.H., Rueger R., Reddy J., D’Amico F., Comsa S., and Collins, B.: Role of arachidonic acid metabolites in tumor growth inhibition by nonsteroidal antiinflammatory drugs, Am. J. Otolaryngol. 18 (1997), 1–8.

    Article  CAS  Google Scholar 

  56. Kuhl P., Shiloh R., Jha H., Murawski U., and Zilliken, F: 6,7,4’-Trihydroxyisoflavan: a potent and selective inhibitor of 5-lipoxygenase in human and porcine peripheral blood leukocytes, Prostaglandins 28 (1984), 783–804.

    Article  CAS  Google Scholar 

  57. Kuhl P., Borbe, H.O., Fischer H., Römer A., and Safayhi, H.: Ebselen reduces the formation of LTB4 in human and porcine leukocytes by isomerisation to its 5S,12R-6-trans-isomer, Prostaglandins 31 (1986), 1029–1048.

    Article  CAS  Google Scholar 

  58. Safayhi H., Tiegs G., and Wendel, A.: A novel biologically active seleno-organic compound-V. Inhibition by ebselen (PZ 51) of rat peritoneal neutrophil lipoxygenase, Biochem. Pharmacol. 34 (1985), 2691–2694.

    Article  CAS  Google Scholar 

  59. Vasange-Tuominen M., Perera-Ivarsson P., Shen J., Bohlin L., and Rolfsen, W.: The fern Polypodium decumanum used in the treatment of psoriasis, and its fatty acid constituents as inhibitors of leukotriene B4 formation, Prostaglandins Leukot. Essent. Fatty Acids 50 (1994), 279–284.

    Article  CAS  Google Scholar 

  60. Powell, W.S.: Reversed-phase high-pressure liquid chromatography of arachidonic acid metabolites formed by cyclooxygenase and lipoxygenases, Analyt. Bioch. 148 (1985), 59–69.

    Article  CAS  Google Scholar 

  61. Veenstra J., van de Pol H., van der Torre H., Schaafsma G., and Ockhuizen, T: Rapid and simple methods for the investigation of lipoxygenase pathways in human granulocytes, J. Chromatogr. 431 (1988), 413–417.

    Article  CAS  Google Scholar 

  62. Wagner, H. and Fessler, B.: In vitro 5-lipoxygenase inhibition by Elipta alba extracts and the coumestan derivative wedelolactone, Planta Med. 52 (1986), 374–377.

    Article  Google Scholar 

  63. Breton J., Keller P., Chabot-Fletcher M., Hillegass L., DeWolf, W.jr., and Griswold, D.: Use of a continuous assay of oxygen consumption to evaluate the pharmacology of 5-lipoxygenase inhibitors, Prostaglandins Leukot. Essent. Fatty Acids 49 (1993), 929–937.

    Article  CAS  Google Scholar 

  64. Scioscia, K.A., Snyderman, C.H., Rueger R., Reddy J., D’Amico F., Comsa S., and Collins, B.: Role of arachidonic acid metabolites in tumor growth inhibition by nonsteroidal antiinflammatory drugs, Am. J. Otolaryngol. 18 (1997), 1–8.

    Article  CAS  Google Scholar 

  65. Wagner, H.: Search for new plant constituents with potential antiphlogistic and antiallergic activity, Planta Med. 55 (1989), 235–241.

    Article  CAS  Google Scholar 

  66. Alcaraz, M.J. and Ferrandiz, M.L.: Modification of arachidonic metabolism by flavonoids, J. Ethnopharmacol. 21 (1987), 209–229.

    Article  CAS  Google Scholar 

  67. Ammon, H.P., Mack, T, Singh, G.B., and Safayhi, H.: Inhibition of leukotriene B4 formation in rat peritoneal neutrophils by an ethanolic extract of the gum resin exudate of Boswellia serrata, Planta. Med. 57 (1991), 203–207.

    Article  CAS  Google Scholar 

  68. Safayhi H., Mack, T, Sabieraj J., Anazodo, M.I., Subramanian, L.R., and Ammon, H.P.: Boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase, J. Pharmacol. Exp. Ther. 261 (1992), 1143–1146.

    CAS  Google Scholar 

  69. Safayhi H., Sailer, E.R., and Ammon, H.P.: Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-beta-boswellic acid, Mol. Pharmacol. 47 (1995), 1212–1216.

    CAS  Google Scholar 

  70. Sailer, E.R., Subramanian, L.R., Rall B., Hoernlein, R.F., Ammon, H.P., and Safayhi, H.: Acetyl-11-keto-beta-boswellic acid (AKBA): structure requirements for binding and 5-lipoxygenase inhibitory activity, Br. J. Pharmacol. 117 (1996), 615–618.

    Article  CAS  Google Scholar 

  71. Etzel, R.: Special extract of Boswellia serrata (H-15) in the treatment of rheumatoid arthritis, Phytomedicine 3 (1996), 91–94.

    Article  Google Scholar 

  72. Gupta I., Parihar A., Malhotra P., Singh, G.B., Ludtke R., Safayhi H., and Ammon, H.P.: Effects of Boswellia serrata gum resin in patients with ulcerative colitis, Eur. J. Med. Res. 2 (1997), 37–43.

    CAS  Google Scholar 

  73. Winking, M. and Simmet, Th.: Pharmacotherapeutic effects of extracts from Boswellia serrata in astrocytoma patients, Abstract of the 43rd Annual Congress on Medicinal Plant Research in Hall/Saale, 1995.

    Google Scholar 

  74. But, P.P.-H., Hu, S.-Y., and Kong, Y.C.: Vascular plants used in Chinese medicine, Fitoterapia 3 (1980), 245–264.

    Google Scholar 

  75. Pröbstle A., Lotter H., Wagner-Redecker W., Matthiesen U., and Bauer, R.: Cyclooxygenase inhibitory constituents from Houttuynia cordata, Phytomedicine 2 (1996), 305–308.

    Article  Google Scholar 

  76. White, H.L. and Glassman, A.T.: Biochemical properties of the prostaglandin/thromboxane synthetase of human blood platelets and comparison with the synthetase of bovine seminal vesicles, Prostaglandins 12 (1976), 811–828.

    Article  CAS  Google Scholar 

  77. Quoc, K.P. and Pascaud, M.: Effects of dietary gamma-linolenic acid on the tissue phospholipid fatty acid composition and the synthesis of eicosanoids in rats, Ann. Nutr. Metab. 40 (1996), 99–108.

    Article  CAS  Google Scholar 

  78. Mirzoeva, O.K., Sud’ina, G.F., Pushkareva, M.A., and Varfolomeev, S.D.: Competitive inhibition of the 5-lipoxygenase-catalysed linoleate oxidation by arachidonic and 5-hydroperoxy-eicosatetraenoic acids, FEBS Letters 377 (1995), 306–308.

    Article  CAS  Google Scholar 

  79. Samuelson, B.: Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation, Science 220 (1983), 568–575.

    Article  Google Scholar 

  80. Pröbstle A., Neszmelyi, Jerkovich G., Wagner H., and Bauer, R.: Novel pyridine and 1,4-dihydropyridine alkaloids from Houttuynia cordata, Natural Product Letters 4 (1994), 235–240.

    Article  Google Scholar 

  81. Nishikawa, Y., Yasuda I., Watanabe Y., and Seto. T.: New polyacetylenic compounds in the rhizome of Atractylodes lancea DC. var. chinensis, YakugakuZasshi 96 (1976), 1322–1326.

    CAS  Google Scholar 

  82. Resch, M.S., Steigel A., and Bauer, R.: Diacetoxy substituted polyacetylenes from Atractylodes lancea, Phytochemistry (1997), in pres

    Google Scholar 

  83. Pachaly P., Lansing A., and Sin, K.S.: Constituents of Atractylis koreana, Planta Med. 55 (1989), 59–61.

    Article  CAS  Google Scholar 

  84. Resch, M.S., Steigel A., Chen, Z.L., and Bauer, R.: 5-Lipoxygenase and cyclooxygenase-1 inhibitory active compounds from Atractylodes lancea, J. Nat. Prod. (1997), submitted.

    Google Scholar 

  85. Capon, J.R., Ghisalberti, E.L. and Jefferies, PR.: Isoprenoid dihydroquinones from a brown alga, Cystophora sp., Phytochemistry 20 (1981), 2598–2600.

    Article  CAS  Google Scholar 

  86. Heilmann J., Resch M., and Bauer R.: Antioxidant and radical scavenging activity of constituents from Atractylodes lancea, Pharmaceutical Pharmacol. Lett. (1997), submitte

    Google Scholar 

  87. Morita M., Nakajima K., Taguchi H., Yanagisawa T., Sato T., Chin M., and Mitsuhashi, H.: New polyacetylenes from Bupleuri radix, Abstract of the 4th World Conference on Clinical Pharmacology and Therapeutics, Prague, 1989.

    Google Scholar 

  88. Alanko J., Kurahashi Y., Yoshimoto T., Yamamoto S., and Baba, K.: Panaxynol, a polyacetylene compound isolated from oriental medicines, inhibits mammalian lipoxygenases, Biochem. Pharmacol. 48 (1994), 1979–1981.

    Article  CAS  Google Scholar 

  89. Bauer, R. and Wagner, H.: Echinacea-Ein Handbuchfür Ärzte, Apotheker und andere Naturwissenschaftler, Wissenschaftliche Verlagsgesellschaft, Stuttgart, 1990.

    Google Scholar 

  90. Bauer R., Remiger P., and Wagner, H.: Alkamides from the roots of Echinacea angustifolia, Phytochemistry 28 (1989), 505–508.

    Article  CAS  Google Scholar 

  91. Wagner H., Breu W., Wilier, E, Wierer M., Remiger, and Schwenker, G.: In vitro inhibition of arachidonate metabolism by some alkamides and alkylated phenols, Planta Med. 55 (1989), 566–567.

    Article  CAS  Google Scholar 

  92. Müller B., Redl K., Breu W., Pröbstle A., Greger H., and Bauer, R.: In vitro inhibition of cyclooxygenase and 5-lipoxygenase by alkamides from Echinacea and Achillea species, Planta Med. 60 (1994), 37–40.

    Article  Google Scholar 

  93. Fish, F. and Waterman, P.G.: Rutaceae-Chloroform-soluble Alkaloids from the Root Bark of Fagara chalybea, Phytochemistry 11 (1972), 1866–1867.

    Article  CAS  Google Scholar 

  94. Nakatani M., Asai H., Mochihara K., and Hase, T.: Jatrorrhizine Chloride and other Constituents from Fagara chalybea, Kagoshima Daigaku Rigakubu Kiyo, Sugaku, Butsurigaku, Kagaku 23 (1990), 153, ref. C.A. 115, 228433x.

    Google Scholar 

  95. Müller-Jakic, B.: PhD thesis, Munich, 1995.

    Google Scholar 

  96. Müller-Jakic B., Pröbstle A., and Bauer R.: In vitro inhibition of 5-lipoxgenase and cyclooxygenase by benzophenanthridine and protoberberine alkaloids, Poster at the 43rd Annual Congress on Medicinal Plant Research in Halle, 1995.

    Google Scholar 

  97. Dostal, J. and Potacek, M.: Quarteraary benzophenanthridine alkaloids, Collect. Czech. Res. Commun. 55 (1990), 2840–2871.

    Article  CAS  Google Scholar 

  98. Vavreckova, C, Gawlik, I. and Müller, K.: Benzophenanthridine alkaloids of Chelidonium majus. I. Inhibition of 5-and 12-lipoxygenase by a non-redox mechanism, Planta Med. 62 (1996), 397–401.

    Article  CAS  Google Scholar 

  99. Wolff, J. and Knipling L,: Antimicrotubule properties of benzophenanthridine alkaloids. Biochemistry 32 (1993), 13334–13339.

    Article  CAS  Google Scholar 

  100. Vavreckova, C, Gawlik, I. and Müller, K.: Benzophenanthridine alkaloids of Chelidonium majus; II. Potent inhibitory action against the growth of human keratinocytes, Planta Med. 62 (1996), 491–494.

    Article  CAS  Google Scholar 

  101. Deshpande, V.H. and Shastri, R.K.: Chemical investigation of three Zanthoxylum species, Z. alatum, Z. oxyphyllum and Z. acconthopodium, Indian J. Chem. 15B (1977), 95–

    Google Scholar 

  102. Chen J., Geng, G.L., Ye, G.H., Xi, F.D., Chen, S.F., He, C.H., and Zheng, Q.T.: Studies on the chemical constituents of Zanthoxylum planispinum Sieb. et Zucc, Acta Pharm. Sinica 23 (1988), 422–425.

    CAS  Google Scholar 

  103. Manandhar, M.D.: Isolation of pinoresinol dimethyl ether from Zanthoxylum alatum Roxb., J. Nep. Chem. Soc. 2 (1982), 19–21.

    CAS  Google Scholar 

  104. Müller-Jakic B., Greger H., Vermes B., and Bauer, R.: Cyclooxygenase and 5-lipoxygenase inhibitory activity of tetrahydrofurofuran lignans, Flavonoids and Bioflavonoids (Eds. S. Antus, M. Gabor, K. Vetschera) pp. 149–156, Akademiai Kiado, Budapest, 1996.

    Google Scholar 

  105. Greger H., and Hofer, O.: Unsymmetrically substituted tetrahydrofurouran lignans from Artemisia absinthium-Assignment of the Relative stereochemistry by lanthanide-induced chemical shifts, Tetrahedron 36 (1980), 3551–3558.

    Article  CAS  Google Scholar 

  106. Brader, G.: Diploma thesis, University of Vienna, 1992.

    Google Scholar 

  107. Vermes B., Seligmann O., and Wagner, H.: Synthesis of biologically active tetrahydrofurofuranlignan-(Syingin, pinoresinol)-mono-and bisglucosides, Phytochemistry 30 (1991), 3087–3089.

    Article  CAS  Google Scholar 

  108. Hutchinson, J.H., Riendeau D., Brideau C., Chan C., Delirme D., Denis D., Falgueyret, J.-P., Fortin R., Guay J., Hamel P., Jones, T.R., Macdonald D., McFarlane, C.S., Piechuta H., Scheigetz J., Tagari P., Therien M., and Girard, Y.: Substituted thiopyrano[2,3,4-c,d]indoles as potent, selective, and orally active inhibitors of 5-lipoxygenase. Synthesis and biological evaluation of L-691,816, J. Med. Chem. 36 (1993), 2771–2787.

    Article  CAS  Google Scholar 

  109. Umeda-Sawada R., Takahashi N., and Igarashi, O.: Interaction of sesamin and eicosapentaenoic acid against delta 5 desaturation and n-6/n-3 ratio of essential fatty acids in rat, Biosci. Biotechnol. Biochem. 59 (1995), 2268–2273.

    Article  CAS  Google Scholar 

  110. Hong, M.F., Pan, Y.Xd., Jiang, T.Y., Li, C.L., and Han, G.Q.: Isolation and characterization of platelet activating factor (PAF) inhibitors from Zanthoxylum schinifolium, J. Chin. Pharm. Sci. 1 (1992), 13–19.

    CAS  Google Scholar 

  111. Hong, M.F., Pan, J.X., Hao M., Yao B., and Han, G.: The active constituents of platelet activating factor (PAF) inhibitors from Zanthoxylum planispinum Sieb. & Zucc, Zhiwu Ziyuan Yu Huanjing, 2 (1993), 25–27; ref. CA. 119, 85668x.

    CAS  Google Scholar 

  112. Ferrandiz, M.L., Nair, A.G.R., and Alcaraz, M.J.: Inhibition of sheep platelet arachidonate metabolism by flavonoids from Spanish and indian medicinal herbs, Pharmazie 45 (1990), 206–208.

    CAS  Google Scholar 

  113. Lyckander, I.M. and Malterud, K.E.: Lipoxygenase Inhibiting Flavonoids from Orthosiphon spicatus, in Das, N.P. (ed.) Flavonoids in Biology & Medicine III: Current Issues in Flavonoid Research, pp. 469–474, National University of Singapore, 1990.

    Google Scholar 

  114. Ferrandiz, M.L. and Alcaraz, M.J.:Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids, Agents Actions 32 (1991), 283–288.

    Article  CAS  Google Scholar 

  115. Berenbaum, M.C.: Isobolographic, algebraic, and search methods in analysis of multiagent synergy, J. Am. Coll. Tox. 7 (1988), 927–937.

    Article  Google Scholar 

  116. Sühnel, J.: Evaluation of synergism or antagonism for the combined action of antiviral agents, Antiviral Res. 13(1990), 23–40.

    Article  Google Scholar 

  117. Liu, J.H., Xu, S.X., Yao, X.S., and Kobayashi, H.: Two new 6-alkylcoumarins from Angelicapubescensf. biserrata, Planta Med. 61 (1995), 482–484.

    Article  CAS  Google Scholar 

  118. Liu, J.H., Xu, S.X., Yao, X.S., and Kobayashi, H.: Angelol-type comarins from Angelica pubescens f. biserrata and their inhibitory effect on platelet aggregation, Phytochemistry 39 (1995), 1099–1101.

    Article  CAS  Google Scholar 

  119. Liu, J.H., Xu, S.X., Yao, X.S., and Kobayashi, H.: Further isolation of chemical constituents from Angelica pubescens f. biserrata, Acta Pharm. Sinica 31 (1996), 63–67.

    CAS  Google Scholar 

  120. Liu, J.H., Zschocke S., and Bauer, R.: A polyacetylenic acetate and a coumarin from Angelica pubescens f. biserrata, Phytochemistry (1997), accepted.

    Google Scholar 

  121. Liu, J.H., Zschocke S., Reininger E., and Bauer, R.: Inhibitory effect of Angelica pubescens f. biserrata on 5-lipoxygenase and cyclooxygenase, Planta Med. (1997), submitted.

    Google Scholar 

  122. Yang, X.-W., Gu, Z.-M., Wang, B.-X., Hattori M., and Namba, T.: Comparison of anti-lipid peroxidative effects of the underground parts of Notopterygium incisum and N.forbesü in mice, Planta Med. 57 (1991), 399–402.

    Article  CAS  Google Scholar 

  123. Zschocke S., Seibt A., Stöhr J., and Bauer, R.: The influence of fatty acids and synergistic effects on the 5-lipoxygenase inhibitory activity of Qianghou (Notopterygium incisum), Poster at the 44th Annual Congress of the Society for medicinal Plant Research in Prague, 1996.

    Google Scholar 

  124. Zschocke, S.: PhD thesis University of Düsseldorf, in preparation.

    Google Scholar 

  125. Sud’ina, G.F., Mirzoeva, O.K., Pushkareva, M.A., Korshunova, G.A., Sumbatyan, N.V., and Varfolomeev, S.D.: Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties, FEBS Lett. 329 (1993), 21–24.

    Article  CAS  Google Scholar 

  126. Natarajan K., Singh S., Burke, T.R.jr., Grunberger D., and Aggarwal, B.B.: Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B, Proc. Natl. Acad. Sci. USA 93 (1996), 9090–9095.

    Article  CAS  Google Scholar 

  127. Yamamoto K., Arakawa T., Ueda N., and Yamamoto, S.: Transcriptional roles of nuclear factor kappa B and nuclear factor-interleukin-6 in the tumor necrosis factor alpha-dependent induction of cyclooxygenase-2 in MC3T3-E1 cells, J. Biol. Chem. 270 (1995), 31315–31320.

    Article  CAS  Google Scholar 

  128. Crofford, L.J., Tan B., McCarthy, C.J., and Hla, T.: Involvement of nuclear factor kappa B in the regulation of cyclooxygenase-2 expression by interleukin-1 in rheumatoid synoviocytes, Arthritis Rheum. 40 (1997), 226–236.

    Article  CAS  Google Scholar 

  129. Chen F., Sun S., Kuhn, D.C., Gaydos. L.J., Shi X., Lu Y., and Demers, L.M.: Involvement of NF-kappa B in silica-induced cyclooxygenase II gene expression in rat alveolar macrophages, Am. J. Physiol. 272 (1997), L779–786.

    Google Scholar 

  130. Lyss G., Schmidt, J.T., Merfort I., and Pahl, H.L.: Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-B, Biol. Chem. 378 (1997), 951–961.

    Article  CAS  Google Scholar 

  131. Hwang D., Fischer, N.H., Jang, B.C., Tak H., Kim, J.K. and Lee, W.: Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sesquiterpene lactones in macrophages correlates with the inhibition of MAP kinases, Biochem. Biophys. Res. Com. 226 (1996), 810–818.

    Article  CAS  Google Scholar 

  132. Tordjman C., Coge F., Andre N., Rique H., Spedding M., and Bonnet, J.: Characterisation of cyclooxygenase 1 and 2 expression in mouse resident peritoneal macrophages in vitro; interactions of non steroidal anti-inflammatory drugs with COX-2, Biochim. Biophys. Acta 1256 (1995), 249–256.

    Article  Google Scholar 

  133. Creminon, C, Habib A., Maclouf J., Pradelles P., Grassi J., and Frobert, Y.: Differential measurement of constitutive (COX-1) and inducible (COX-2) cyclooxygenase expression in human umbilical vein endothelial cells using specific immunometric enzyme immunoassays, Biochim. Biophys. Acta 1254 (1995), 341–348.

    Article  Google Scholar 

  134. Zschocke S., Lehner M., Bauer, R.: 5-Lipoxygenase and cyclooxygenase inhibitory constituents from Qianghuo (Notopterygium incisum), Planta Med. 63 (1997), 203–206.

    Article  CAS  Google Scholar 

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  1. Institut für Pharmazeutische Biologie der Universität Düsseldorf, Universitätsstr. 1, D-40225, Düsseldorf, Germany

    R. Bauer

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    Lars Bohlin  & Jan G. Bruhn  & 

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Bauer, R. (1999). Cyclooxygenase and 5-Lipoxygenase as Targets for Medicinal Plant Research. In: Bohlin, L., Bruhn, J.G. (eds) Bioassay Methods in Natural Product Research and Drug Development. Proceedings of the Phytochemical Society of Europe, vol 43. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4810-8_10

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