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Ecdysones of Plant Origin

  • H. Hikino
  • T. Takemoto

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.

Keywords

Callus Tissue Tetrahedron Letter Insect Hormone Taxus Cuspidata Close Taxonomic Relationship 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 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. 2.
    Galbraith, M. N. and Horn, D.H. S.: An Insect-molting Hormone from a Plant. Chem. Commun., p. 905, 1966.Google Scholar
  3. 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. 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. 5.
    Heinrich, G. and Hoffmeister, H.: Ecdyson als Begleitsubstanz des Ecdysterons in Polypodium vulgare L. Experientia, 23:995, 1967.PubMedCrossRefGoogle Scholar
  6. 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.Google Scholar
  7. 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. 8.
    Hikino, H., Nomoto, K., and Takemoto, T.: Posterone, a Metabolite of Insect-metamorphosing Substances from Cyathula capitata. Steroids, 16:393, 1970.PubMedCrossRefGoogle Scholar
  9. 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.Google Scholar
  10. 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.CrossRefGoogle Scholar
  11. 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. 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.PubMedCrossRefGoogle Scholar
  13. 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. 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. 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.CrossRefGoogle Scholar
  16. 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. 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.Google Scholar
  18. 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. 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. 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.PubMedCrossRefGoogle Scholar
  21. 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. 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. 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. 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.Google Scholar
  25. 25.
    Rimpler, H.: Steroide mit ecdysonartiger Wirkung aus Vitex megapotarnica. Pharmaz. Ztg., 48:1799, 1967.Google Scholar
  26. 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. 27.
    Rimpler, H. and Schulz, G.: Vorkommen von 20-Hydroxy-ecdyson in Vitex megapotamica. Tetrahedron Letters, p. 2033, 1967.Google Scholar
  28. 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. 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.PubMedCrossRefGoogle Scholar
  30. 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. 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. 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. 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.Google Scholar
  34. 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.Google Scholar
  35. 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. 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.Google Scholar
  37. 37.
    Takemoto, T., Hikino, Y., Jin, H., and Hikino, H.: Isolation of Ponasterone A from Taxus cuspidata var. nana. Yakugaku Zasshi, 88:359, 1968.Google Scholar
  38. 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. 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. 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. 41.
    Takemoto, T., Ogawa, S., and Nishimoto, N.: Isolation of Molting Hormones of Insects from Achyranthes Radix. Yakugaku Zasshi, 87:325, 1967.Google Scholar
  42. 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.PubMedGoogle Scholar
  43. 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. 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. 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.PubMedGoogle Scholar
  46. 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. 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. 48.
    Unpublished results in our laboratory.Google Scholar
  49. 49.
    Unpublished results, M. N. Galbraith and D. H. S. Horn.Google Scholar

Copyright information

© Springer-Verlag New York Inc. 1974

Authors and Affiliations

  • H. Hikino
  • T. Takemoto

There are no affiliations available

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