Skip to main content
SpringerLink
Log in

Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

A new tirucallane-type triterpenoid named 24-epi-piscidinol A (1) has been isolated fromCastela texana (T. & G.) Rose (Simaroubaceae) and determined to have the structure 23R,24R,25-trihydroxytirucall-7-en-3-one by X-ray crystallographic analysis. Crystals of 24-epi-piscidinol A are monoclinic, space groupC2,a=23.84 (3),b=7.012 (7),c=17.35 (2) Å, β=103.46 (2)o. Another triterpenoid piscidinol A (2), crystallizes in the orthorhombic space groupP212121 witha=10.659 (2),b=14.499 (3),c=17.922 (4) Å, β=90°. Two coumarino-lignans, cleomiscosin A and C, were also obtained in the course of this work. This is the first time of isolation of tirucallane-type triterpenoids and coumarino-lignans from the genusCastela.

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. Correll, D.S.; Johnston, M.C.Manual of the vascular plants of Texas; Texas Research Foundation: Render, Texas, 1970; pp 911–2.

    Google Scholar 

  2. Kubo, I.; Murai, Y.; Chaudhuri, S.K.Phytochemistry 1992,31, 3262.

    Article  CAS  Google Scholar 

  3. Chaudhuri, S.K.; Kubo, I.,Phytochemistry 1992,31, 3961.

    Article  CAS  Google Scholar 

  4. Kubo, I.; Chaudhuri, S.K.Phytochemistry 1993,32, 215.

    Article  Google Scholar 

  5. Dou, J.; McChesney, J.D.; Sindelar, R.D.; Goins, D.K.; Walker L.A.J. Nat. Prod. 1996,59, 73.

    Article  CAS  Google Scholar 

  6. Fukamiya, M.O.; Lee, K.H.Studies in Natural Products Chemistry: Rahman, A., Ed.; Vol. 7: Elsevier Science Publishers B.V.: Amsterdam, 1990; pp 369–404.

    Google Scholar 

  7. Itokawa, H.; Kishi, E.; Morita, H.; Takeya, K.Chem. Pharm. Bull. 1992,40, 1053.

    CAS  Google Scholar 

  8. Arisawa, M.; Fujita, A.; Morita, N.; Cox, P.J.; Howie, R.A.; Cordell, G.A.Phytochemistry 1987,26, 3301.

    Article  CAS  Google Scholar 

  9. Sherman, M.M.; Borris, R.P.; Ogura, M.; Cordell, G.A.; Farnsworth, N.R.Phytochemistry 1980,19, 1499.

    CAS  Google Scholar 

  10. Polonsky, J.; Baskevitch-Varon, Z.; Das, B.C.Phytochemistry 1976,15, 337.

    Article  CAS  Google Scholar 

  11. Merrien, A.; Polonsky, J.Chem. Commun. 1971, 261.

  12. Cabral, J.A.; McChesney, J.D.; Milhous, W.K.J. Nat. Prod. 1993,56, 1954.

    Article  CAS  Google Scholar 

  13. Jolad, S.D.; Hoffmann, J.J.; Shram, K.H.; Cole, J.R.; Tempesta, M.S.; Bates, R.B.J. Org. Chem. 1981,46, 4085.

    Article  CAS  Google Scholar 

  14. Purushothaman, K.K.; Duraiswamy, K.; Connolly, J.D.; Rycroft, D.S.Phytochemistry 1985,24, 2349

    Article  CAS  Google Scholar 

  15. Mulholland, D.A.; Taylor, D.A.H.Phytochemistry 1988,27, 1220.

    Article  CAS  Google Scholar 

  16. Gray, A.I.; Bhandari, P.; Waterman, P.G.Phytochemistry 1988,27, 1805.

    Article  CAS  Google Scholar 

  17. Su, R.; Kim, M.; Kawaguchi, H.; Yamamoto, T.; Goto, K.; Taga, T.; Miwa, Y.; Kozuka, M.; Takahashi, S.Chem. Pharm. Bull. 1990,38, 1616.

    CAS  Google Scholar 

  18. Arisawa, M.; Handa, S.S.; McPherson, D.D.; Lankin, D.C.; Cordell, G.A.; Fong, H.H.S.; Farnsworth, N.R.J. Nat. Prod. 1984,47, 300.

    Article  CAS  Google Scholar 

  19. Ray, A.B.; Chattopadhyay, S.K.; Kumar, S.; Konno, C.; Kiso, Y., Hikino, H.Tetrahedron 1985,41, 209.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmacognosy, University of Mississippi, 38677, University, Mississippi

    James D. McChesney & Jinhui Dou

  2. Research Institute of Pharmaceutical Sciences, University of Mississippi, 38677, University, Mississippi

    James D. McChesney, Robert D. Sindelar, D. Keith Goins & Larry A. Walker

  3. Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, 38677, University, Mississippi

    Robert D. Sindelar

  4. Department of Chemistry, Northern Illinois University, 60115-2862, DeKalb, Illinois

    Robin D. Rogers

Authors
  1. James D. McChesney
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jinhui Dou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Robert D. Sindelar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. Keith Goins
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Larry A. Walker
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Robin D. Rogers
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

McChesney, J.D., Dou, J., Sindelar, R.D. et al. Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A. J Chem Crystallogr 27, 283–290 (1997). https://doi.org/10.1007/BF02575975

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02575975

Key Words

Search

Navigation