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Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 153))

Abstract

Beside molecules produced by classical organic synthesis, by combinatorial chemistry or designed by molecular modeling, natural products represent a large source of new chemical entities, potential lead compounds or novel drugs. These compounds originate from higher plants, marine organisms, fungi and animals, or are produced by microorganisms or yeasts using biotechnology. This chapter will focus on secondary metabolites from higher plants.

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References

  • Boonen G, Häberlein H (1998) Influence of genuine kavapyrone enantiomers on the GABA-A binding site. Planta Med 64:504–506

    Article  PubMed  CAS  Google Scholar 

  • Boonen G, Ferger B, Kuschinsky K, Häberlein H (1998) In vivo effects of the kavapyrones (+)-dihydromethysticin and (+/-)-kavain on dopamine, 3,4-dihydroxyphenylacetic acid, serotonin and 5-hydroxyindoleacetic acid levels in striatal and cortical brain regions. Planta Med 64:507–510

    Article  PubMed  CAS  Google Scholar 

  • Boonen G, Pramanik A, Rigler R, Häberlein H (2000) Evidence for specific interactions between kavain and human cortical neurons monitored by fluorescence correlation spectroscopy. Planta Med 66:7–10

    Article  PubMed  CAS  Google Scholar 

  • Burkhard PR, Burkhardt K, Haenggeli CA, Landis T (1999) Plant-induced seizures: reappearance of an old problem. J Neurol 246:667–670

    Article  PubMed  CAS  Google Scholar 

  • Connor J, Makonnen E, Rostom A (2000) Comparison of analgesic effects of khat (Catha edulis Forsk.) extract, D-amphetamine and ibuprofen in mice. J Pharm Pharmacol 52:107–110

    Article  PubMed  CAS  Google Scholar 

  • Croteau R, Gershenzon J, Wheeler CJ, Satterwhite DM (1990) Biosynthesis of monoterpenes: stereochemistry of the coupled isomerization and cyclization of geranyl pyrophosphate to camphane and isocamphane monoterpenes. Arch Biochem Biophys 277:374–381

    Article  PubMed  CAS  Google Scholar 

  • CSPV (2000) Atteintes hépatiques liées aux extraits de kawa. J Suisse Pharm 138: 437–438

    Google Scholar 

  • Davies LP, Drew CA, Duffield P, Johnston GA, Jamieson DD (1992) Kava pyrones and resin: studies on GABA-A, GABA-B and benzodiazepine binding sites in rodent brain. Pharmacol Toxicol 71:120–126

    Article  PubMed  CAS  Google Scholar 

  • Dräger B (1996) Wie kommt Atropin in die Tollkirsche? Neues zur Regulation des pflanzlichen Sekundärstoffwechsels. Pharm Uns Zeit 25:242–249

    Article  Google Scholar 

  • Eccles R (1994) Menthol and related cooling compounds. J Pharm Pharmacol 46:618–630

    Article  PubMed  CAS  Google Scholar 

  • Francis PD, Clarke CF (1999) Angel trumpet lily poisoning in five adolescents: clinical findings and management. J Paediatr Child Health 35:93–95

    Article  PubMed  CAS  Google Scholar 

  • Häberlein H, Boonen G, Beck M-A (1997) Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. Planta Med 63:63–65

    Article  PubMed  Google Scholar 

  • Halket JM, Karasu Z, Murray-Lyon IM (1995) Plasma cathinone levels following chewing khat leaves (Catha edulis Forsk). J Ethnopharmacol 49:111–113

    Article  PubMed  CAS  Google Scholar 

  • Hansel R, Sticher O, Steinegger E (1999) Pharmakognosie—Phytopharmazie. Springer, Berlin

    Google Scholar 

  • Holm E, Staedt U, Heep J, Kortsik C, Behne F, Kaske A, Mennicke I (1991) The action profile of D,L-kavain. Cerebral sites and sleep-wakefulness-rhythm in animals. Arzneim-Forsch / Drug Res 41:673–683

    CAS  Google Scholar 

  • Hostettmann K, Potterat O, Wolfender J-L (1998) The potential of higher plants as a source of new drugs. Chimia 52:10–17

    CAS  Google Scholar 

  • Jamali F, Mehvar R, Pasutto FM (1989) Enantioselective aspects of drug action and disposition: therapeutic pitfalls. J Pharm Sei 78:695–715

    Article  CAS  Google Scholar 

  • Kalix P (1996) Catha edulis, a plant that has amphetamine effects. Pharm World Sci 18:69–73

    Article  PubMed  CAS  Google Scholar 

  • Leitereg TJ, Guadagni DG, Harris J, Mon TR,T eranishi R (1971) Evidence for the difference between the odours of the optical isomers (+)-and (-)-carvone. Nature 230:455–456

    Article  PubMed  CAS  Google Scholar 

  • Liaudet L, Buclin T, Jaccard C, Eckert P (1999) Drug points: severe ergotism associated with interaction between ritonavir and ergotamine. BMJ 318:771

    Google Scholar 

  • Mann J (1992) Murder, Magic and Medicine. Oxford University Press, Oxford, UK

    Google Scholar 

  • Nunes MA, Brochmann-Hanssen E (1974) Hydrolysis and epimerization kinetics of pilocarpine in aqueous solution. J Pharm Sci 63:716–721

    Article  PubMed  CAS  Google Scholar 

  • Pallenbach E (1996) Die Männer mit der dicken Backe. Khat im Jemen. Dtsch Apoth Ztg 136:3399–3410

    Google Scholar 

  • Rang HP, Ritter JM, Dale MM (1995) Pharmacology. Churchill Livingstone, Edinburgh

    Google Scholar 

  • Rauber C, Guirguis M, Meier-Abt AS, Gossweiler B, Meier PJ (1999) Lethal poisoning after ingestion of a tea prepared from the angel’s trumpet (Datura suaveolens). XIX International Congress, EAPCCT, Dublin, Eire, June 22–25

    Google Scholar 

  • Ravid U, Putievsky E, Katzir I (1993) Determination of the enantiomeric composition of (1R) (+)-and (IS) (-)-camphor in essential oils of some Lamiaceae and Compositae herbs. Flav Fragr J 8:225–228

    Article  CAS  Google Scholar 

  • Reist M, Testa B, Carrupt P-A, Jung M, Schurig V (1995) Racemization, enantiomerization, diastereomerization, and epimerization: their meaning and pharmacological significance. Chirality 7:396–400

    Article  CAS  Google Scholar 

  • Shelley MD, Hartley L, Fish RG, Groundwater P, Morgan JJ, Mort D, Mason M, Evans A (1999) Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumour cell lines. Cancer Lett 135:171–180

    Article  PubMed  CAS  Google Scholar 

  • Singh YN (1992) Kava: an overview. J Ethnopharmacol 37:13–45

    Article  PubMed  CAS  Google Scholar 

  • Szepesi G, Gazdag M, Ivancsics R, Mihalyfi K, Kovacs P (1983) Investigation of degradation mechanism of pilocarpine by HPLC. Pharmazie 38:94–98

    CAS  Google Scholar 

  • Testa B, Carrupt PA, Gal J (1993) The so-called “interconversion” of stereoisomeric drugs: an attempt at clarification. Chirality 5:105–111

    Article  PubMed  CAS  Google Scholar 

  • Volz H-P, Kieser M (1997) Kava-kava extract WS 1490 versus placebo in anxiety disorders—a randomized placebo-controlled 25-week outpatient trial. Pharmacopsychiatry 30:1–5

    Article  PubMed  CAS  Google Scholar 

  • Wu YW (1987) Probing into the mechanism of action, metabolism and toxicity of gossypol by studying its (+)-and (-)-stereoisomers. J Ethnopharmacol 20:65–78

    Article  Google Scholar 

  • Wu D (1989) An overview of the clinical pharmacology and therapeutic potential of gossypol as a male contraceptive agent and in gynaecological disease. Drugs 38: 333–341

    Article  PubMed  Google Scholar 

Download references

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© 2003 Springer-Verlag Berlin Heidelberg

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Terreaux, C., Hostettmann, K. (2003). Stereochemical Issues in Bioactive Natural Products. In: Eichelbaum, M., Testa, B., Somogyi, A. (eds) Stereochemical Aspects of Drug Action and Disposition. Handbook of Experimental Pharmacology, vol 153. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-55842-9_3

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  • DOI: https://doi.org/10.1007/978-3-642-55842-9_3

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-62575-6

  • Online ISBN: 978-3-642-55842-9

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