Skip to main content
SpringerLink
Log in

Structure and Conformational Analysis of Napelline-Type Diterpenoid Alkaloids

  • Published:
Chemistry of Natural Compounds Aims and scope

X-ray crystal structure analyses of six compounds (napelline, napelline N-oxide EtOH solvate, 1-O-benzoylnapelline EtOH solvate, songorine hydrochloride monohydrate EtOH solvate, 1-O-benzoylsongorine, and N-deethylsongorine) showed that the diterpenoid alkaloid napelline had the β-configuration of the C12 hydroxyl. It was found that the N-oxide in napelline N-oxide had the R-configuration. Two types of intramolecular H-bonds could occur in the studied alkaloids and their salts, i.e., between the unshared electron pair on the skeletal N atom and the C1 OH and between the C12 and C15 OH groups. Ring A adopted the boat conformation if the first type of H-bond formed. The second type of H-bond did not cause significant conformational changes.

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

Fig. 1

Similar content being viewed by others

References

  1. M. N. Sultankhodzhaev, in: Progress in Research on Alkaloid-Bearing Plants [in Russian], Fan, Tashkent, 1993, pp. 37–62.

  2. F. N. Dzhakhangirov, M. N. Sultankhodzhaev, B. Tashkhodzhaev, and B. T. Salimov, Chem. Nat. Compd., 33, 190 (1997).

    Article  CAS  Google Scholar 

  3. N. Kh. Shakhidoyatova, F. N. Dzhakhangirov, and M. N. Sultankhodzhaev, Khim.-farm. Zh., 35, 31 (2001).

    Google Scholar 

  4. K. Wiesner, Z. Valenta, J. F. King, R. K. Maudgal, L. G. Hamber, and S. Ito, Chem. Ind., 173 (1957).

  5. lookchem.com, Catalog, Napelline, CAS 5008-52-6.

  6. A. Yosino and Y. Iitaka, Acta Crystallogr., 21, 57 (1966).

    Article  Google Scholar 

  7. M. N. Sultankhodzhaev, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 9, 194 (1973).

    Article  Google Scholar 

  8. Atta-ur-Rahman, Atia-tul-Vahab, B. Tashkhodzhaev, K. K. Turgunov, M. N. Sultankhodzhaev, and M. I. Choudhary, Chem. Nat. Compd., 41, 609 (2005).

  9. M. N. Sultankhodzhaev, L. V. Beshitaishvili, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 14, 407 (1978).

    Article  Google Scholar 

  10. M. N. Sultankhodzhaev and M. S. Yunusov, Chem. Nat. Compd., 23, 319 (1987).

    Article  Google Scholar 

  11. M. N. Sultankhodzhaev, L. V. Beshitaishvili, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 15, 731 (1979).

    Article  Google Scholar 

  12. V. I. Nezhevenko, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 11, 400 (1975).

    Article  Google Scholar 

  13. Z.-C. Fan and Z.-Q. Zhang, J. Chem. Crystallogr., 38, 635 (2008).

    Article  CAS  Google Scholar 

  14. Z.-C. Fan and Z.-Q. Zhang, Z. Kristallogr.-New Cryst. Struct., 223, 111 (2008).

    CAS  Google Scholar 

  15. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Streek, J. Appl. Crystallogr., 39, 453 (2006).

    Article  CAS  Google Scholar 

  16. B. Tashkhodzhaev, M. N. Sultankhodzhaev, and I. M. Yusupova, Chem. Nat. Compd., 29, 222 (1993).

    Article  Google Scholar 

  17. B. T. Salimov, K. K. Turgunov, B. Tashkhodzhaev, and F. N. Dzhakhangirov, Chem. Nat. Compd., 40, 151 (2004).

    Article  CAS  Google Scholar 

  18. B. Tashkhodzhaev, Chem. Nat. Compd., 46, 421 (2010).

    Article  CAS  Google Scholar 

  19. A. S. Samatov, S. T. Akramov, and S. Yu. Yunusov, Dokl. Akad. Nauk UzSSR, No. 5, 21 (1965).

  20. Crys Alis Pro, Oxford Diffraction Ltd., Yarnton, England, 2009.

  21. G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Goettingen, Goettingen, 1996.

    Google Scholar 

  22. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The work was sponsored by the Basic Research Program of KKRNT, Rep. Uzb., Grant FA-F7-T185.

Author information

Authors and Affiliations

  1. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, Uzbekistan

    M. N. Sultankhodzhaev, B. Tashkhodzhaev, K. K. Turgunov, U. Kh. Kurbanov & N. I. Mukarramov

Authors
  1. M. N. Sultankhodzhaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. Tashkhodzhaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. K. Turgunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. U. Kh. Kurbanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. I. Mukarramov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. K. Turgunov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 85–89.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sultankhodzhaev, M.N., Tashkhodzhaev, B., Turgunov, K.K. et al. Structure and Conformational Analysis of Napelline-Type Diterpenoid Alkaloids. Chem Nat Compd 53, 99–104 (2017). https://doi.org/10.1007/s10600-017-1919-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-017-1919-1

Keywords

Search

Navigation