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Trichome Microsampling of Sesquiterpene Lactones for the Use of Systematic Studies

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Modern Phytochemical Methods

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 25))

Abstract

Over the last two decades few classes of secondary plant metabolites have attracted as much attention from phytochemists as sesquiterpene lactones (STL), which are characteristic metabolites of the Asteraceae. While Fischer et al.1 reviewed some 900 hundred different structures of naturally occuring STL in 1979, Seaman2 counted over 1300 only three years later and their number has increased at a rate of 200 to 250 a year since then (Fig 1).1–6 Interest in the broad spectrum of biological activities of these compounds (for reviews see 7,8) is probably the major driving force for this development.

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References

  1. FISCHER, N.H., OLIVIER, E.J., FISCHER, H.D. 1979. The biogenesis and chemistry of sesquiterpene lactones. In: Progress in the Chemistry of Organic Natural Products. (W. Herz, H. Griesebach, G.W. Kirby, eds.), Springer-Verlag, New York. pp. 48–390.

    Chapter  Google Scholar 

  2. SEAMAN, F. 1982. Sesquiterpene lacones as taxonomic characters of the Asteraceae. Bot Rev. 48: 121–595.

    Article  CAS  Google Scholar 

  3. FRAGA, B.M. 1986. Natural Products Reports, pp. 273–296.

    Google Scholar 

  4. VASQUEZ, M. 1989. Structure elucidation of secondary metabolites from Rudbeckia species by spectroscopic techniques and review of sesquiterpene lactones. Dissertation, Louisiana State University, Baton Rouge, U.S.A.

    Google Scholar 

  5. YOSHIOKA, H., MABRY, T.J., TIMMERMANN, B.N. 1973. Sesquiterpene lactones, Chemistry, NMR and Plant Distribution. Tokyo, university of Tokyo Press.

    Google Scholar 

  6. KORTE, F., BARKEMEYER, H., KORTE, I. 1959. Neuere Ergebnisse der Chemie pflanzlicher Bitterstoffe. In: Fortschritte der Chemie organischer Naturstoffe. (L. Zechmeister, ed.), Springer-Verlag, Wien. Vol. 17, pp. 124–182.

    Google Scholar 

  7. RODRIGUEZ, E., TOWERS, G.H.N., Mitchell, J.C. 1976. Biological activities of sesquiterpene lactones. Phytochemistry 15: 1573–1580.

    Article  CAS  Google Scholar 

  8. PICMAN, A.K. 1986. Biological activities of sesquiterpene lactones. Biochem. Syst. Ecol. 14: 255–281.

    Article  CAS  Google Scholar 

  9. SPRING, O. 1989. Microsampling: An alternative approach using sesquiterpene lactones for systematics. Biochem. Syst. Ecol. 17: 509–517.

    Article  CAS  Google Scholar 

  10. SEAMAN, F.C., MABRY, T.J. 1979. Sesquiterpene lactones and species relationships among the shrubby Ambrosia taxa. Biochem. Syst. Ecol. 7: 105–114.

    Article  CAS  Google Scholar 

  11. GERSHENZON, J. 1984. The terpenoid chemistry of Helianthus, series Corona solis and its ecological and systematic application. Dissertation, University of Texas, Austin, U.S.A.

    Google Scholar 

  12. PAYNE, W.W., GEISSMAN, T.A., LUCAS, A.J., SAITOH, T. 1973. Chemosystematics and taxonomy of Ambrosia chamissonis. Biochem. Syst. Ecol. 1: 21–33.

    Article  CAS  Google Scholar 

  13. SPRING, O., SCHILLING, E.E. 1989. Chemosystematic investigation of the annual species of Helianthus (Asteraceae). Biochem. Syst. Ecol. 17: 519–528.

    Article  CAS  Google Scholar 

  14. SPRING, O., SCHILLING, E.E. 1990. The sesquiterpene lactone chemistry of Helianthus sect. Ciliares. Biochem. Syst. Ecol. 18: 139–143.

    Article  CAS  Google Scholar 

  15. SPRING, O., SCHILLING, E.E. 1990. The sesquiterpene lactone chemistry of Helianthus sect. Atrorubentes. Biochem. Syst. Ecol., in press.

    Google Scholar 

  16. SEAMAN, F.C., MABRY, T.J. 1979. Sesquiterpene lactones of diploid and tetraploid Ambrosia camphorata. Biochem. Syst Ecol. 7: 3–5.

    Article  CAS  Google Scholar 

  17. SEAMAN, F.C., MABRY, T.J. 1979. Sesquiterpene lactone patterns in diploid and polyploid Ambrosia dumosa. Biochem. Syst. Ecol. 7: 7–12.

    Article  CAS  Google Scholar 

  18. POLITES, J. 1946. Sur la formation des glucosides amers dans les poiles glanduleux de certaines plantes. Compt Rend. 222: 910–911.

    Google Scholar 

  19. POLITES, J. 1946. Sur le mode de formation des essences dans certaines poils glanduleux. Compt. Rend. 222: 1244–1245.

    Google Scholar 

  20. POLITES, J. 1947. Developpement et destruction des cellules secretrices des glands florales des Centaurea contenant des essences et des heterosides (glucosides) amers. Compt. Rend. 225: 139–141.

    Google Scholar 

  21. WEBER, U., DEUFEL, J. 1951. Zur Cytologie der Drüsenhaare von Achillea millefolium. Arch. Pharm. 284/56: 318–323.

    Article  Google Scholar 

  22. STAHL, E. 1952. Nachweis der Vorstufe des Azulens in den Drüsenhaaren der Schafgarbe. Naturwissenschaften 39: 551–552.

    Article  CAS  Google Scholar 

  23. RODRIGUEZ, E., DILLON, M.O., MABRY, T.J., MITCHELL, J.C., TOWERS, G.H.N. 1976. Dermatologically active sesquiterpene lactones in trichomes of Parthenium hysterophorus L. (Compositae). Experientia 32: 236–238.

    Article  PubMed  CAS  Google Scholar 

  24. SPRING, O., BIENERT, U., KLEMT, V. 1987. Sesquiterpene lactones in glandular trichomes of sunflower leaves. J. Plant Physiol. 130: 433–439.

    Article  CAS  Google Scholar 

  25. SPRING, O., BIENERT, U. 1987. Capitate glandular hairs from sunflower leaves: development, distribution and sesquiterpene lactone content. J. Plant Physiol. 130: 441–448.

    Article  CAS  Google Scholar 

  26. SPRING, O., PRIESTER, T., KLEMT, V., KRUPPA, J. 1989. The possible function of sesquiterpene lactones in sunflowers. Proc. Sunflower Res. Workshop, Fargo, N. Dakota.

    Google Scholar 

  27. SPRING, O., BENZ, T., ILG, M. 1989. Sesquiterpene lactones of the glandular trichomes of Helianthus annuus. Phytochemistry 28: 745–749.

    Article  CAS  Google Scholar 

  28. SCHILLING, E.E. 1983. Flavonoids of Helianthus series Angustifolii. Biochem. Syst. Ecol 11: 341–344.

    Article  CAS  Google Scholar 

  29. GEISSMANN, T.A., GRIFFIN, T.S. 1971. Sesquiterpene lactones: acid catalysed color reaction as an aid in structure determination. Phytochemistry 10: 2475–2485.

    Article  Google Scholar 

  30. PICMAN, A.K., RANIERI, R.L., TOWERS, G.H.N., LAM, J. 1980. Visualization reagents for sesquiterpene lactones and polyacetylenes on thin-layer chromatograms. J. Chromatography 189: 187–198.

    Article  CAS  Google Scholar 

  31. JAMIESON, G.R., REID, E.H., TURNER, B.P., JAMIESON, A.T. 1976. Bakkenolide-A. Its distribution in Petasites species and cytotoxic properties. Phytochemistry 15: 1713–1715.

    Article  CAS  Google Scholar 

  32. BOHLMANN, F., FRITZ, U., KING, R.M., ROBINSON, H. 1981. Fourteen heliangolides from Calea species. Phytochemistry 20: 743–749.

    Article  CAS  Google Scholar 

  33. ROMO DE VIVAR, A., GUERRERO, C., DIAZ, E., BRATOEFF, E.A., JIMENEZ, L. 1976. The germacranolides of Viguiera budlei-aeformis: structures of budlein-A, -B. Phytochemistry 15: 525–527.

    Article  Google Scholar 

  34. LEE, E. 1989. Terpenoids from Helianthus species. Dissertation, University of Texas, Austin, U.S.A.

    Google Scholar 

  35. STRACK, D., PROKSCH, P., Gülz, P.-G. 1980. Analysis of sesquiterpene lactones by high performance liquid chromatography. Z. Naturforsch. 35c: 915–918.

    CAS  Google Scholar 

  36. SPRING, O., PRIESTER, T., STRANSKY, H., HAGER, A. 1985. Sesquiterpene lactones in sunflower seedlings: distribution in the plant and occurrence in genetic varieties as determined by an isocratic HPLC technique. J. Plant Physiol. 120: 321–329.

    Article  CAS  Google Scholar 

  37. HERZ, W., KUMAR, N. 1981. Heliangolides from Helianthus maximiliani. Phytochemistry 20: 93–98.

    Article  CAS  Google Scholar 

  38. GERSHENZON, J., MABRY, T.J., KORP, J.D., BERNAL, I. 1984. Germacranolides from Helianthus californicus. Phytochemistry 23: 2561–2571.

    Article  CAS  Google Scholar 

  39. GAO, F., MABRY, T.J. 1986. Sesquiterpene lactones from Viguiera deltoidea. Phytochemistry 25: 137–140.

    Article  CAS  Google Scholar 

  40. MORIMOTO, H., SANNO, Y., OSHIO, H. 1966. Chemical studies on heliangine. Tetrahedron 22: 3173–3179.

    Article  CAS  Google Scholar 

  41. HERZ, W., KUMAR, N. 1981. Sesquiterpene lactones from Helianthus grosseserratus. Phytochemistry 20: 99–104.

    Article  CAS  Google Scholar 

  42. DAVIS, P.H., HEYWOOD, V.H. 1963. Principles of angiosperm taxonomy. D. Van Nosband Co. Inc., Princeton, New York.

    Google Scholar 

  43. HEGNAUER, R. 1977. The chemistry of the Compositae. In: The Biology and Chemistry of the Compositae, (V.H. Heywood, J.B. Harborne, B.L Turner, eds.), Academic Press, London — New York -San Francisco.

    Google Scholar 

  44. HERZ, W. 1977. Sesquiterpene lactones in the Compositae. In: The Biology and Chemistry of the Compositae. (V.H. Heywood, J.B. Harborne, B.L Turner, eds.), Academic Press, London — New York - San Francisco.

    Google Scholar 

  45. KELSEY, R.G., MORRIS, M.S., BHADANE, N.R., SHAFIZADEH, F. 1973. Sesquiterpene lactones of Artemisia: TLC analysis and taxonomic significance. Phytochemistry 12: 1345–1350.

    Article  CAS  Google Scholar 

  46. GERSHENZON, J., MABRY, TJ. 1984. Sesquiterpene lactones from a Texas population of Helianthus maximiliani. Phytochemistry 23: 1959–1966.

    Article  CAS  Google Scholar 

  47. STEWART, E., MABRY, T.J. 1985. Further sesquiterpene lactones from Helianthus maximiliani. Phytochemistry 24: 2733–2734.

    Article  CAS  Google Scholar 

  48. ROGERS, C.E., THOMPSON, T.E., SEILER, G.J. 1982. Sunflower species of the United States. The National Sunflower Association, Bismarck, N. Dakota.

    Google Scholar 

  49. HEISER, C.B., SMITH, D.M., CLEVENGER, S.B., MARTIN, W.C. 1969. The North American sunflowers (Helianthus). Mem. Torrey Bot. Club 22: 1–218.

    Google Scholar 

  50. SCHILLING, E.E., HEISER, C.B. 1981. Infrageneric classification of Helianthus. Taxon 30: 393–403.

    Article  Google Scholar 

  51. GAO, F., WANG, H., MABRY, T.J. 1987. Sesquiterpene lactones and flavonoids from Helianthus species. J. Nat. Prod. 50: 23–29.

    Article  PubMed  CAS  Google Scholar 

  52. GUTIERREZ, A.B., HERZ, W. 1988. Guaianolides and other constituents of Helianthus microcephalus. Phytochemistry 27: 2225–2228.

    Article  CAS  Google Scholar 

  53. SPRING, O., SCHILLING, E.E. 1990. The origin of Helianthus x multiflorus and H. x laetiflorus (Asteraceae). Biochem. Syst. Ecol. 18: 13–23.

    Article  Google Scholar 

  54. PANERO, J. 1989. Systematics of the Awdean genus Pappobolus (Asteraceae: Heliantheae). Systematic Botany Monographs, in press.

    Google Scholar 

  55. ROBINSON, H. 1979. Studies in the Heliantheae. A new genus Helianthopsis. Phytologia 44: 257–269.

    Google Scholar 

  56. BOHLMANN, F., DUTTA, L.N. 1979. Ein neues Heliangolide aus Helianthopsis lehmannii. Phytochemistry 18: 676.

    Article  CAS  Google Scholar 

  57. SPRING, O., VARGAS, D., FISCHER, N.H. 1991. Sesquiterpene lactones and benzofurans in glandular trichomes of three Pappobolus (Helianthopsis) species. Phytochemistry 30: 000–000.

    Google Scholar 

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Author information

Authors and Affiliations

  1. Institute of Biology, University of Tuebingen, Auf der Morgenstelle 1, D-7400, Tuebingen, Germany

    Otmar Spring

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  1. Otmar Spring
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Editors and Affiliations

  1. Louisiana State University, Baton Rouge, Louisiana, USA

    Nikolaus H. Fischer

  2. University of British Columbia, Vancouver, British Columbia, Canada

    Murray B. Isman

  3. Reed College, Portland, Oregon, USA

    Helen A. Stafford

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© 1991 Plenum Press, New York

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Spring, O. (1991). Trichome Microsampling of Sesquiterpene Lactones for the Use of Systematic Studies. In: Fischer, N.H., Isman, M.B., Stafford, H.A. (eds) Modern Phytochemical Methods. Recent Advances in Phytochemistry, vol 25. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-9060-2_9

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  • DOI: https://doi.org/10.1007/978-1-4684-9060-2_9

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  • Online ISBN: 978-1-4684-9060-2

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