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The Medicinal Chemistry of Echinacea Species

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Echinacea

Abstract

Extensive scientific research on Echinacea species revealed that the bioactive components most likely responsible for the immunostimulatory activities of Echinacea were alkamides, caffeic acid derivatives, glycoproteins, and polysaccharides. Three species, namely Echinacea purpurea, E. angustifolia and E. pallida, are predominantly used in herbal supplement preparations. Also, different plant parts are shown to have different amounts of the bioactive components. In addition, the phytochemistry, quality control based analysis of bioactive constituents, as well as addressing the safety concerns related to Echinacea herbal supplement preparations are discussed.

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References

  • American Herbal Pharmacopoeia. 2010a. Echinacea angustifolia Root: Standards of analysis, quality control, and therapeutics. Scotts Valley, CA: American Herbal Pharmacopoeia and Therapeutic Compendium.

    Google Scholar 

  • ———. 2010b. Echinacea pallida root: Standards of analysis, quality control, and therapeutics. Scotts Valley, CA: American Herbal Pharmacopoeia and Therapeutic Compendium.

    Google Scholar 

  • Barnes, J., L.A. Anderson, S. Gibbons, and J.D. Phillipson. 2005. Echinacea species (Echinacea angustifolia (DC.) Hell. Echinacea pallida (Nutt.) Nutt., Echinacea purpurea (L.) Moench): a review of their chemistry, pharmacology and clinical properties. The Journal of Pharmacy and Pharmacology 57(8): 929–954.

    Article  CAS  PubMed  Google Scholar 

  • Bauer, R., P. Remiger, and H. Wagner. 1988. Alkamides from the roots of Echinacea purpurea. Phytochemistry 21(7): 2339–2342.

    Article  Google Scholar 

  • Bauer, R., P. Remiger, and H. Wagner. 1988b. Echinacea Part 3. Comparative TLC and HPLC analysis of herbal drugs from Echinacea purpurea, E. pallida and E. angustifolia. Deutsche Apotheker-Zeitung 128(4): 174–180.

    Google Scholar 

  • Bauer, R., P. Remiger, and H. Wagner. 1989. Alkamides from the roots of Echinacea angustifolia. Phytochemistry 28(2): 505–508.

    Article  CAS  Google Scholar 

  • Bauer, R., and P. Remiger. 1989. Echinacea. Part V. TLC and HPLC analysis of alkamides in Echinacea drugs. Planta Medica 55(4): 367–371.

    Article  CAS  PubMed  Google Scholar 

  • Bauer, Rudolf, and S. Foster. 1991. Echinacea. Part VI. Analysis of alkamides and caffeic acid derivatives from Echinacea simulata and E. paradoxa roots. Planta Medica 57(5): 447–449.

    Article  CAS  PubMed  Google Scholar 

  • Bauer, R. 1999. Chemistry, analysis and immunological investigations of Echinacea phytopharmaceuticals. In: Wagner, H. (ed.). Immunomodulatory Agents from Plants. Basel, Switzerland: Birkhuser Verlag. 41–88.

    Google Scholar 

  • Becker, H., W.C. Hsieh, R. Wylde, C. Laffite, and C. Andary. 1982. Structure of echinacoside. Zeitschrift fuer Naturforschung. C. Journal of Biosciences 37C(5-6): 351–353.

    CAS  Google Scholar 

  • Bergeron, C., and S. Gafner. 2007. Quantitative analysis of the polysaccharide and glycoprotein fractions in Echinacea purpurea. and Echinacea angustifolia by HPLC-ELSD for quality control of raw material. Pharmaceutical Biology 45(2): 98–105.

    Article  CAS  Google Scholar 

  • Bohlmann, F., and M. Grenz. 1966. Polyacetylene compounds. CXII. Components of Echinacea varieties. Chemische Berichte 99(10): 3197–3200.

    Article  CAS  Google Scholar 

  • Bohlmann, F., and H. Hoffmann. 1983. Further amides from Echinacea purpurea. Phytochemistry 22(5): 1173–1175.

    Article  CAS  Google Scholar 

  • Borchers, A.T., C.L. Keen, J.S. Stern, and M.E. Gershwin. 2000. Inflammation and native American medicine: The role of botanicals. The American Journal of Clinical Nutrition 72(2): 339–347.

    CAS  PubMed  Google Scholar 

  • Brown, P.N., M. Chan, and J.M. Betz. 2010. Optimization and single-laboratory validation study of a high-performance liquid chromatography (HPLC) method for the determination of phenolic Echinacea constituents. Analytical and Bioanalytical Chemistry 397(5): 1883–1892.

    Article  CAS  PubMed  Google Scholar 

  • Cech, N.B., M.S. Eleazer, L.T. Shoffner, M.R. Crosswhite, A.C. Davis, and A.M. Mortenson. 2006. High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts. Journal of Chromatography. A 1103(2): 219–228.

    Article  CAS  PubMed  Google Scholar 

  • Cheminat, A., R. Zawatzky, H. Becker, and R. Brouillard. 1988. Caffeoyl conjugates from Echinacea species: Structures and biological activity. Phytochemistry 27(9): 2787–2794.

    Article  CAS  Google Scholar 

  • Chen, Y., T. Fu, T. Tao, J. Yang, Y. Chang, M. Wang, L. Kim, L. Qu, J. Cassady, R. Scalzo, and X. Wang. 2005. Macrophage activating effects of new alkamides from the roots of Echinacea species. Journal of Natural Products 68: 773–776.

    Article  CAS  PubMed  Google Scholar 

  • Cozzolino, R., P. Malvagna, E. Spina, A. Giori, N. Fuzzati, A. Anelli, D. Garozzo, and G. Impallomeni. 2006. Structural analysis of the polysaccharides from Echinacea angustifolia radix. Carbohydrate Polymers 65(3): 263–272.

    Article  CAS  Google Scholar 

  • Dietz, B., and R. Bauer. 2001. The constituents of Echinacea atrorubens roots and aerial parts. Pharmaceutical Biology 39(1): 11–15.

    Article  CAS  Google Scholar 

  • Freeman, C., and K. Spelman. 2008. A critical evaluation of drug interactions with Echinacea spp. Molecular Nutrition & Food Research 52: 789–798.

    Article  CAS  Google Scholar 

  • Glavač, N.K., I.J. Košir, J. Rode, and S. Samo Kreft. 2012. Optimization and use of a spectrophotometric method for determining polysaccharides in Echinacea purpurea. Central European Journal of Biology 7(1): 126–131.

    Google Scholar 

  • Gocan, S., L. Radu, and M. Hadaruga. 2003. Simultaneous analysis by high performance liquid chromatography of hydrophilic compounds and lipophilic compounds (alkamides) from pharmaceutical preparations of Echinacea purpurea root. Chromatographia 57(9–10): 677–679.

    Article  CAS  Google Scholar 

  • Gupta, M., D. Sharma, A. Sharma, V. Kumari, and O.P. Goshain. 2012. A review on purple cone flower (Echinacea purpurea L. Moench). Journal of Pharmacy Research 5(8): 4076–4081.

    CAS  Google Scholar 

  • Harbonrne, J.B., and C.A. Williams. 2004. Phytochemistry of the Genus Echinacea. In Echinacea. The genus Echinacea, ed. S.C. Miller and H. Yu, 48–64. Boca Raton: CRC.

    Google Scholar 

  • Hudson, J.B. 2012. Applications of the phytomedicine Echinacea purpurea (purple coneflower) in infectious diseases. Journal of Biomedicine & Biotechnology 2012: 769896.

    Article  Google Scholar 

  • Huntley, A.L., J.T. Coon, and E. Ernst. 2005. The safety of herbal medicinal products derived from Echinacea species: a systematic review. Drug Safety 28(5): 387–400.

    Article  PubMed  Google Scholar 

  • Jacobson, M. 1954. Occurrence of a pungent insecticidal principle in American coneflower roots. Science 120: 1028–1029.

    Article  CAS  PubMed  Google Scholar 

  • Jacobson, M. 1967. The Structure of echinacein, the insecticidal component of American coneflower Roots. The Journal of Organic Chemistry 32: 1646–1647.

    Article  CAS  PubMed  Google Scholar 

  • Kindscher, K. 1989. The ethnobotany of the purple coneflower (Echinacea angustifolia) and other Echinacea species. Economic Botany 43(4): 498–507.

    Article  Google Scholar 

  • Kraemer, H., and M. Sollenberger. 1911. The pharmacognosy of Echinacea. The American Journal of Pharmacy 83: 315–324.

    CAS  Google Scholar 

  • Kotowska, D., R.B. El-Houri, K. Borkowski, R.K. Petersen, X.C. Fretté, G. Wolber, K. Grevsen, K.B. Christensen, L.P. Christensen, and K. Kristiansen. 2014. Isomeric C12-alkamides from the roots of Echinacea purpurea improve basal and insulin-dependent glucose uptake in 3T3-L1 adipocytes. Planta Medica 80(18): 1712–1720.

    Article  CAS  PubMed  Google Scholar 

  • LaLone, C.A., K.D.P. Hammer, L. Wu, J. Bae, N. Leyva, Y. Liu, A.K.S. Solco, G.A. Kraus, P.A. Murphy, E.S. Wurtele, O.K. Kim, K. Seo II, M.P. Widrlechner, and D.F. Birt. 2007. Echinacea species and alkamides inhibit prostaglandin E2 production in RAW264.7 mouse macrophage cells. Journal of Agricultural and Food Chemistry 55(18): 7314–7322.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Luo, X.B., B. Chen, S.Z. Yao, and J.G. Zeng. 2003. Simultaneous analysis of caffeic acid derivatives and alkamides in roots and extracts of Echinacea purpurea by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. Journal of Chromatography. A 986(1): 73–81.

    Article  CAS  PubMed  Google Scholar 

  • Miller, S.C. 2004. Echinacea in vivo: a prophylactic agent in normal mice and a therapeutic agent in leukemic mice. In Echinacea. The genus Echinacea, ed. S.C. Miller and H. Yu, 150–158. Boca Raton: CRC Press.

    Google Scholar 

  • Mills, S., and K. Bone. 2005. The essential guide to herbal safety. St. Louis, Missouri: Elsevier Health Sciences.

    Google Scholar 

  • Mitscher, L.A., and R. Cooper. 2004. Echinacea and immunostimulation. In Herbal and traditional medicine biomolecular and clinical aspects, ed. Packe Lester, Ong Choon Nam, and Halliwell Barry, 721–756. Boca Raton: CRC Press.

    Google Scholar 

  • Mudge, E., D. Lopes-Lutz, P. Brown, and A. Schieber. 2011. Analysis of alkylamides in Echinacea plant materials and dietary supplements by ultrafast liquid chromatography with diode array and mass spectrometric detection. Journal of Agricultural and Food Chemistry 59(15): 8086–8094.

    Article  CAS  PubMed  Google Scholar 

  • Pellati, F., G. Orlandini, and S. Benvenuti. 2012. Simultaneous metabolite fingerprinting of hydrophilic and lipophilic compounds in Echinacea pallida by high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometry detection. Journal of Chromatography. A 1242: 43–58.

    Article  CAS  PubMed  Google Scholar 

  • Pillai, S., C. Pillai, L.A. Mitscher, and R. Cooper. 2007. Use of quantitative flow cytometry to measure ex vivo immunostimulant activity of echinacea: the case for polysaccharides. Journal of Alternative Comparative Medicine 2007(13): 625–634.

    Article  Google Scholar 

  • Proksch, A., and H. Wagner. 1987. Structural analysis of a 4-O-methylglucuronoarabinocylan with immunostimulating activity from Echinacea purpurea. Phytochemistry 26: 1989–1993.

    Article  CAS  Google Scholar 

  • Rininger, J.A., K. Ringer, and M. Savarese. 2004. In vitro immunopharmacology of Echinacea. In Echinacea. The genus Echinacea, ed. S.C. Miller and H. Yu, 165–176. Boca Raton: CRC.

    Google Scholar 

  • Sestakova, H., and B. Turek. 2004. Effect of Echinacea on cells involved in disease defense. In Echinacea. The genus Echinacea, ed. S.C. Miller and H. Yu. Boca Raton: CRC Press.

    Google Scholar 

  • Shin, D.M., K.M. Choi, Y.S. Lee, W. Kim, K.O. Shin, S. Oh, J.C. Jung, M.K. Lee, Y.M. Lee, J.T. Hong, Y.P. Yun, and H.S. Yoo. 2014. Echinacea purpurea root extract enhances the adipocyte differentiation of 3T3-L1 cells. Archives of Pharmacal Research 37(6): 803–812.

    Article  CAS  PubMed  Google Scholar 

  • Stimpel, M., A. Proksch, H. Wagner, and M.L. Lohmann-Matthes. 1984. Macrophage activation and induction of macrophage cytotoxicity by purified polysaccharide fractions from the plant Echinacea purpurea. Infection and Immunity 46(3): 845–849.

    CAS  PubMed  PubMed Central  Google Scholar 

  • Stoll, A., J. Renz, and A. Brack. 1950. Isolation and constitution of the Echinacoside, a glycoside from the roots of Echinacea angustifolia DC 6. Notification of antibacterial substances. Helvetica Chimica Acta 33(6): 1877–1893.

    Article  CAS  Google Scholar 

  • Stuppner, H. 1985. Chemische und immunologische Untersuchungen von Polysacchariden aus der Gewebekultur von Echinacea purpurea (L.) Moench, Ph.D. thesis, University of Münich.

    Google Scholar 

  • Wagner, H., and A.Z. Proksch. 1981. Über ein immunstimulerendes workprinzip aus Echinacea purpurea Moench (An immunostimulating active principle from Echinacea purpurea Moench). Zeitschrift für Angewandte Phytotheraphy 2: 166–171.

    CAS  Google Scholar 

  • Wagner, H., A. Proksch, I. Riess-Maurer, A. Vollmar, S. Odenthal, H. Stuppner, K. Jurcic, M. Le Turdu, and Y.H. Heur. 1984. Immunostimulating polysaccharides (heteroglycans) from higher plants. Arzneimittel Forschung 34(6): 659–661.

    CAS  PubMed  Google Scholar 

  • Wagner, H., H. Stuppner, W. Schäfer, and M. Zenk. 1988. Immunologically active polysaccharides of Echinacea purpurea cell cultures. Phytochemistry 27: 119–126.

    Article  CAS  Google Scholar 

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  1. University of Kansas, Lawrence, KS, 66045, USA

    Congmei Cao

  2. Kansas Biological Survey, University of Kansas, Lawrence, KS, USA

    Kelly Kindscher

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  1. Congmei Cao
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  1. Kansas Biological Survey, University of Kansas, Lawrence, Kansas, USA

    Kelly Kindscher

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Cao, C., Kindscher, K. (2016). The Medicinal Chemistry of Echinacea Species. In: Kindscher, K. (eds) Echinacea. Springer, Cham. https://doi.org/10.1007/978-3-319-18156-1_9

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