Skip to main content
SpringerLink
Log in

(24R-14α-methyl-24-ethyl-5α-cholest-9(11)-en-3β-ol: A new 14α-methylsterol fromCucumis sativus

  • Published:
Lipids

Abstract

The structure of a new 14α-methylsterol isolated fromCucumis sativus has been shown to be (24R)-14α-methyl-24-ethyl-5α-cholest-9(11)-en-3β-ol. Characterization of the 14α-methyl-Δ9(11) skeletal structure was undertaken based on the comparison with 14α,24-dimethyl-5α-cholest-9(11)-en-3β-ol obtained from 24-methylpollinastanol by acid-catalyzed isomerization. Isolation and identification of an additional 14α-methylsterol, 24-methylene-pollinastanol, from the plant also is described.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Akihisa, T., Thakur, S., Rosenstein, F.U., and Matsumoto, T. (1986)Lipids 21, 39–47.

    Article  CAS  Google Scholar 

  2. Akihisa, T., Shimizu, N., Tamura, T., and Matsumoto, T. (1986)Lipids 21, 494–497.

    Article  CAS  Google Scholar 

  3. Itoh, T., Kikuchi, Y., Tamura, T., and Matsumoto, T. (1981)Phytochemistry 20, 761–764.

    Article  CAS  Google Scholar 

  4. Shimizu, N., Itoh, T., Saito, M., and Matsumoto, T. (1984)J. Org. Chem. 49, 709–712.

    Article  CAS  Google Scholar 

  5. Doyle, P.J., Patterson, G.W., Dutky, S.R., and Thompson, M.J. (1972)Phytochemistry 11, 1951–1960.

    Article  CAS  Google Scholar 

  6. Knapp, F.F., Phillips, D.O., Goad, L.J., and Goodwin, T.W. (1972)Phytochemistry 11, 3497–3500.

    Article  CAS  Google Scholar 

  7. Nes, W.R., Varkey, T.E., and Krevitz, K. (1977)J. Am. Chem. Soc. 99, 260–262.

    Article  PubMed  CAS  Google Scholar 

  8. Shimizu, N., Itoh, T., Ichinohe, Y., and Matsumoto, T. (1984)Bull. Chem. Soc. Jpn. 57, 1425–1426.

    Article  CAS  Google Scholar 

  9. Doyle, P.J., Patterson, G.W., Dutky, S.R., and Cohen, C.F. (1971)Phytochemistry 10, 2093–2098.

    Article  CAS  Google Scholar 

  10. Nes, W.R., Krevitz, K., and Behzadan, S. (1976)Lipids 11, 118–126.

    Article  CAS  Google Scholar 

  11. Rubinstein, I., Goad, L.J., Clague, A.D.H., and Mulheirn, L.J. (1976)Phytochemistry 15, 195–200.

    Article  CAS  Google Scholar 

  12. Chiu, P.-L., and Patterson, G.W. (1981)Lipids 16, 203–206.

    CAS  Google Scholar 

  13. Kalinovskaya, N.I., Kalinovskii, A.I., Kuznetsova, T.A., Stonik, V.A., and Elyakov, G.B. (1984)Dokl. Akad. Nauk. SSSR 278, 630–633.

    CAS  Google Scholar 

  14. Goad, L.J., Garneau, F.-X., Simard, J.-L., ApSimon, J.W., and Girard, M. (1985)Tetrahedron Lett. 26, 3513–3516.

    Article  CAS  Google Scholar 

  15. Kadota, S., Matsuda, S., Suehara, H., and Kikuchi, T. (1984)Chem. Pharm. Bull. 32, 1256–1259.

    CAS  Google Scholar 

  16. Hügel, M.F., Barbier, M., and Lederer, E. (1964)Bull. Soc. Chim. Fr. 81, 2012–2013.

    Google Scholar 

  17. Djerassi, C., Knights, J.C., and Wilkinson, D.I. (1963)J. Am. Chem. Soc. 85, 835.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Science and Technology, Nihon University, 1-8, Kanda Surugadai, Chiyoda-ku, 101, Tokyo, Japan

    Toshihiro Akihisa, Toshitake Tamura & Taro Matsumoto

  2. Ibaraki Research Lab., Hitachi Chemical Co. Ltd., 4-13-1, Higashi-cho, 317, Hitachi-shi, Ibaraki, Japan

    Naoto Shimizu

Authors
  1. Toshihiro Akihisa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Naoto Shimizu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Toshitake Tamura
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Taro Matsumoto
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Akihisa, T., Shimizu, N., Tamura, T. et al. (24R-14α-methyl-24-ethyl-5α-cholest-9(11)-en-3β-ol: A new 14α-methylsterol fromCucumis sativus . Lipids 21, 491–493 (1986). https://doi.org/10.1007/BF02535634

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535634

Keywords

Search

Navigation