Skip to main content

Ecdysones of Plant Origin

  • Chapter

Abstract

It is well known that the first insect molting hormone, α-ecdysone, was isolated from the silkworm, Bombyx mori, by Butenandt and Karlson in 1954 with a background of pioneering work performed by a number of researchers involved in the purification of the hormone. Since then six additional molting hormones (zooecdysones) have been isolated from a variety of arthropods, insects, and crustaceans. The content of these zooecdysones in animals is only 10-5–10-9 per cent; the compound occurring most commonly is β-ecdysone. The structure of α-ecdysone was first elucidated in 1965, and the structures of another five zooecdysones were successively determined thereafter.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Chong, Y. K., Galbraith, M. N., and Horn, D. H. S.: Isolation of Deoxycrustecdy-sone, Deoxyecdysone, and α-Ecdysone from the Fern Blechnum minus. Chem. Commun., p. 1217, 1970.

    Google Scholar 

  2. Galbraith, M. N. and Horn, D.H. S.: An Insect-molting Hormone from a Plant. Chem. Commun., p. 905, 1966.

    Google Scholar 

  3. Galbraith, M. N., Horn, D. H. S., Middleton, E. J., and Hackney, R. J.: The Structure of Podecdysone B, a New Phytoecdysone. Chem. Commun., p. 402, 1969.

    Google Scholar 

  4. Galbraith, M. N., Horn, D. H. S., Porter, Q. N., and Hackney, R. J.: Structure of Podecdysone A, a Steroid with Molting Hormone Activity from the Bark of Podocarpus elatus R. Br. Chem. Commun., p. 971, 1968.

    Google Scholar 

  5. Heinrich, G. and Hoffmeister, H.: Ecdyson als Begleitsubstanz des Ecdysterons in Polypodium vulgare L. Experientia, 23:995, 1967.

    Article  PubMed  CAS  Google Scholar 

  6. Hikino, H., Nomoto, K., Ino, R., and Takemoto, T.: Structure of Precyasterone, a Novel C29 Insect-molting Substance from Cyathula capitata. Chem. Pharm. Bull. (Japan), 18:1078, 1970.

    CAS  Google Scholar 

  7. Hikino, H., Nomoto, K., and Takemoto, T.: Structure of Sengosterone, a Novel C29 Insect-molting Substance from Cyathula capitata. Tetrahedron Letters, p. 1417, 1969.

    Google Scholar 

  8. Hikino, H., Nomoto, K., and Takemoto, T.: Posterone, a Metabolite of Insect-metamorphosing Substances from Cyathula capitata. Steroids, 16:393, 1970.

    Article  PubMed  CAS  Google Scholar 

  9. Hikino, H., Nomoto, K., and Takemoto, T.: Structure of Isocyasterone and Epicyasterone, Novel C29 Insect-molting Substances from Cyathula capitata. Chem. Pharm. Bull. (Japan), 19:433, 1971.

    CAS  Google Scholar 

  10. Hoffmeister, H., Heinrich, G., Staal, G. B., and van der Berg, W. J.: Uber das Vorkommem von Ecdysteron in Eiben. Naturwissenschaften, 54:471, 1967.

    Article  CAS  Google Scholar 

  11. Imai, S., Fujioka, S., Murata, E., Otsuka, K., and Nakanishi, K.: Structure of the Phytoecdysone, Ajugasterone B. Chem. Commun., p. 82, 1969.

    Google Scholar 

  12. Imai, S., Fujioka, S., Nakanishi, K., Koreeda, M., and Kurokawa, T.: Extraction of Ponasterone A and Ecdysterone from Podocarpaceae and Related Plants. Steroids, 10:557, 1967.

    Article  PubMed  CAS  Google Scholar 

  13. Imai, S., Hori, M., Fujioka, S., Murata, E., Goto, M., and Nakanishi, K.: Isolation of Four New Phytoecdysones, Makisterone A, B, C, D and the Structure of Makisterone A, a C28 Steroid. Tetrahedron Letters, p. 3883, 1968.

    Google Scholar 

  14. Imai, S., Murata, E., Fujioka, S., Koreeda, M., and Nakanishi, K.: Structure of Ajugasterone C, a Phytoecdysone with an 11-Hydroxy Group. Chem. Commun., p. 546, 1969.

    Google Scholar 

  15. Imai, S., Murata, E., Fujioka, S., Matsuoka, T., Koreeda, M., and Nakanishi, K.: Structures of Stachysterone A, the First Natural 27-Carbon Steroid with a Rearranged Methyl Group, and Stachysterone B. J. Amer. Chem. Soc, 92:7510, 1970.

    Article  Google Scholar 

  16. Imai, S., Murata, E., Fujioka, S., Matsuoka, T., Koreeda, M., and Nakanishi, K.: Structure of Stachysterones C and D. Chem. Commun., p. 352, 1970.

    Google Scholar 

  17. Imai, S., Toyosato, T., Sakai, M., Sato, Y., Fujioka, S., Murata, E., and Goto, M.: Isolation of Cyasterone and Ecdysterone from Plant Materials. Chem. Pharm. Bull. (Japan), 17:335, 1969.

    CAS  Google Scholar 

  18. Jizba, J., Herout, V., and Sorm, F.: Isolation of Ecdysterone (Crustecdysone) from Poly podium vulgare L. Rhizomes. Tetrahedron Letters, p. 1689, 1967.

    Google Scholar 

  19. Jizba, J., Herout, V., and Sorm, F.: Polypodine B — a Novel Ecdysone-like Sub- stance from Plant Material. Tetrahedron Letters, p. 5139, 1967.

    Google Scholar 

  20. Kaplanis, J. N., Thompson, M. J., Robbins, W. E., and Bryce, B. M.: Insect Horones: α-Ecdysone and 20-Hydroxyecdysone in Bracken Fern. Science, 157:1436, 1967.

    Article  PubMed  CAS  Google Scholar 

  21. Koreeda, M. and Nakanishi, K.: 5β-Hydroxy-ecdysones and a Revision of the Structure of Ponasterone C. Chem. Commun., p. 351, 1970.

    Google Scholar 

  22. Nakanishi, K., Koreeda, M., Chang, M. L., and Hsu, H. Y.: Insect Hormones. V. The Structures of Ponasterones B and C. Tetrahedron Letters, p. 1105, 1968.

    Google Scholar 

  23. Nakanishi, K., Koreeda, M., Sasaki, S., Chang, M. L., and Hsu, H. Y.: Insect Hormones. I. The Structure of Ponasterone A, an Insect-molting Hormone from the Leaves of Podocarpus nakaii Hay. Chem. Commun., p. 915, 1966.

    Google Scholar 

  24. Ogawa, S., Nishimoto, N., Okamoto, N., and Takemoto, T.: Studies on the Constituents of Achyranthes Radix. VIII. The Insect-molting Substances in Achyranthes Genus. (Supplement 2), Yakugaku Zasshi, 91:916, 1971.

    CAS  Google Scholar 

  25. Rimpler, H.: Steroide mit ecdysonartiger Wirkung aus Vitex megapotarnica. Pharmaz. Ztg., 48:1799, 1967.

    Google Scholar 

  26. Rimpler, H.: Pterosteron, Polypodin B und ein neues ecdysonartiges Steroid (Viticosteron E) aus Vitex megapotamica (Verbenaceae). Tetrahedron Letters, p. 329, 1969.

    Google Scholar 

  27. Rimpler, H. and Schulz, G.: Vorkommen von 20-Hydroxy-ecdyson in Vitex megapotamica. Tetrahedron Letters, p. 2033, 1967.

    Google Scholar 

  28. Russell, G. B., Horn, D. H. S., and Middleton, E. J.: New Phytoecdysones from Dacrydium intermedium. Chem. Commun., p. 71, 1971.

    Google Scholar 

  29. Santos, A. C., Chua, M. T., Eufemio, N., and Abela, C.: Isolation of Commister-one, a New Phytoecdysone from Cyanotics vaga. Experientia, 26:1053, 1970.

    Article  PubMed  CAS  Google Scholar 

  30. Takemoto, T., Arihara, S., and Hikino, H.:Structure of Ponasteroside A, a Novel Glycoside of Insect-molting Substance from Pteridium aquilinum var. latius-culum. Tetrahedron Letters, p. 4199, 1968.

    Google Scholar 

  31. Takemoto, T., Arihara, S., Hikino, Y., and Hikino, H.: Isolation of Insect Molting Substances from Pteridium aquilinum var. latiusculum. Chem. Pharm. Bull. (Japan), 16:162, 1968.

    Google Scholar 

  32. Takemoto, T., Hikino, Y., Arai, T., and Hikino, H.: Structure of Lemmasterone, a Novel C29 Insect-molting Substance from Lemmaphyllum microphyllum. Tetrahedron Letters, p. 4061, 1968.

    Google Scholar 

  33. Takemoto, T., Hikino, Y., Arai, T., Kawahara, M., Konno, C., Arihara, S., and Hikino, H.: Isolation of Insect-molting Substances from Matteuccia struthiopteris, Lastrea thelypteris, and Onoclea sensibilis. Chem. Pharm. Bull. (Japan), 15:1816, 1967.

    CAS  Google Scholar 

  34. Takemoto, T., Hikino, Y., Arai, T., Konno, C., Nabetani, S., and Hikino, H.: Isolation of Insect-molting Substances from Pleopeltis thunbergiana, Neocheiropteris ensata, and Lemmaphyllum microphyllum. Chem. Pharm. Bull. (Japan), 16:759, 1968.

    CAS  Google Scholar 

  35. Takemoto, T., Hikino, Y., Hikino, H., Ogawa, S., and Nishimoto, N.: Structure of Rubrosterone, a Novel C19 Metabolite of Insect-molting Substances from Achyranthes rubrofusca. Tetrahedron Letters, p. 3053, 1968.

    Google Scholar 

  36. Takemoto, T., Hikino, Y., Jin, H., Arai, T., and Hikino, H.: Isolation of Insect-molting Substances from Osmunda japonica and Osmunda asiatica. Chem. Pharm. Bull. (Japan), 16:1636, 1968.

    CAS  Google Scholar 

  37. Takemoto, T., Hikino, Y., Jin, H., and Hikino, H.: Isolation of Ponasterone A from Taxus cuspidata var. nana. Yakugaku Zasshi, 88:359, 1968.

    CAS  Google Scholar 

  38. Takemoto, T., Hikino, Y., Nomoto, K., and Hikino, H.: Structure of Cyasterone, a Novel C29 Insect-molting Substance from Cyathula capitata. Tetrahedron Letters, p. 3191, 1967.

    Google Scholar 

  39. Takemoto, T., Nomoto, K., and Hikino, H.: Structure of Amarasterone A and B, Novel C29 Insect-molting Substances from Cyathula capitata. Tetrahedron Letters, p. 4953, 1968.

    Google Scholar 

  40. Takemoto, T., Nomoto, K., Hikino, Y., and Hikino, H.: Structure of Capitaster-one, a Novel C29 Insect-molting Substance from Cyathula capitata. Tetrahedron Letters, p. 4929, 1968.

    Google Scholar 

  41. Takemoto, T., Ogawa, S., and Nishimoto, N.: Isolation of Molting Hormones of Insects from Achyranthes Radix. Yakugaku Zasshi, 87:325, 1967.

    CAS  Google Scholar 

  42. Takemoto, T., Ogawa, S., Nishimoto, N., Hirayama, H., and Taniguchi, S.: Studies on the Constituents of Achyranthes Radix. VII. The Insect-molting Substances of Achyranthes and Cyathula Supplement. Yakugaku Zasshi, 88:1293, 1968.

    PubMed  CAS  Google Scholar 

  43. Takemoto, T., Ogawa, S., Nishimoto, N., Hirayama, H., and Taniguchi, S.: Isolation of the Insect-molting Hormones from Mulberry Leaves. Yakugaku Zasshi, 87:748, 1967.

    Google Scholar 

  44. Takemoto, T., Ogawa, S., Nishimoto, N., and Hoffmeister, H.: Steroide mit Häutungshormon-Aktivität aus Tieren und Pflanzen. Z. Naturforsch., 22b:681, 1967.

    Google Scholar 

  45. Takemoto, T., Ogawa, S., Nishimoto, N., and Taniguchi, S.: Studies on the Constituent of Achyranthes Radix. IV. Isolation of the Insect-molting Hormones from Formosan Achyranthes spp. Yakugaku Zasshi, 87:1478, 1967.

    PubMed  CAS  Google Scholar 

  46. Takemoto, T., Ogawa, S., Nishimoto, N., Yen, K. -Y., Abe, K., Sato, T., Osawa, K., and Takahaski, M.: The Isolation of Ecdysterone from the Radix of Achyranthes obtusifolia Lam. Yakugaku Zasshi, 87:1521, 1967.

    Google Scholar 

  47. Takemoto, T., Okuyama, T., Arihara, S., Hikino, Y., and Hikino, H.: Isolation of Insect-molting Substances from Blechnum amabile and Blechnum niponicum. Chem. Pharm. Bull. (Japan), 17:1973, 1969.

    Google Scholar 

  48. Unpublished results in our laboratory.

    Google Scholar 

  49. Unpublished results, M. N. Galbraith and D. H. S. Horn.

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1974 Springer-Verlag New York Inc.

About this chapter

Cite this chapter

Hikino, H., Takemoto, T. (1974). Ecdysones of Plant Origin. In: Burdette, W.J. (eds) Invertebrate Endocrinology and Hormonal Heterophylly. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65769-6_16

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-65769-6_16

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-65771-9

  • Online ISBN: 978-3-642-65769-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics