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α- and γ-Apienes, Ferovinal, and Ferocin from Ferula ovina

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Chemistry of Natural Compounds Aims and scope

The esters ferovinal (α-apiene-type) and ferocin (γ-apiene-type) were isolated from Ferula ovina. Their structures were established by analyzing IR, PMR, and 13C NMR spectra; DEPT, HSQC, COSY, NOESY, and HMBC experiments; and X-ray crystal structure analyses (XSAs). The XSAs determined the molecular structures and absolute configurations of ferovinal and ferocin and established that their 11-membered humulane macrocycles adopted the 14,15U78 and 14,15U78 conformations. The C8 p-hydroxybenzoate groups in these apienes occupied β-equatorial positions. The only chiral center in ferovinal and ferocin had the 8S-configuration.

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References

  1. Kh. I. Khasanova, K. A. Eshbakova, K. K. Turgunov, B. Tashkhodzhaev, and H. A. Aisa, Chem. Nat. Compd., 56, 249 (2020).

    Article  CAS  Google Scholar 

  2. L. A. Golovina and A. I. Saidkhodzhaev, Chem. Nat. Compd., 13, 671 (1977).

    Article  Google Scholar 

  3. G. V. Sagitdinova and I. Saidkhodzhaev, Chem. Nat. Compd., 13, 665 (1977).

    Article  Google Scholar 

  4. L. A. Golovina and G. K. Nikonov, Chem. Nat. Compd., 13, 591 (1977).

    Article  Google Scholar 

  5. A. I. Saidkhodzhaev, Chem. Nat. Compd., 15, 379 (1979).

    Article  Google Scholar 

  6. M. Miski, T. J. Mabry, and O. Saya, Phytochemistry, 26, 1733 (1987).

    Article  CAS  Google Scholar 

  7. S. Dev, J. E. Anderson, V. Cormier, N. P. Damondaran, and J. D. Roberts, J. Am. Chem. Soc., 90, 1246 (1968).

    Article  CAS  Google Scholar 

  8. M. K. Makhmudov, B. Tashkhodzhaev, G. V. Sagitdinova, A. I. Saidkhodzhaev, M. R. Yagudaev, and V. M. Malikov, Chem. Nat. Compd., 25, 39 (1986).

    Article  Google Scholar 

  9. O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, A. I. Saidkhodzhaev, G. V. Sagitdinova, and N. G. Furmanova, Chem. Nat. Compd., 29, 643 (1990).

    Article  Google Scholar 

  10. O. Yu. Rekhlova, B. Tashkhodzhaev, V. I. Andrianov, G. V. Sagitdinova, and A. I. Saidkhodzhaev, Chem. Nat. Compd., 30, 430 (1991).

    Article  Google Scholar 

  11. B. Tashkhodzhaev and A. I. Saidkhodzhaev, Chem. Nat. Compd., 44, 125 (2005).

    Google Scholar 

  12. B. Tashkhodzhaev and A. I. Saidkhodzhaev, Chem. Nat. Compd., 31, 168 (1992).

    Article  Google Scholar 

  13. CrysAlisPRO, Oxford Diffraction Ltd., Yarnton, England, 2009.

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

    Google Scholar 

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

  16. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 71, 3 (2015).

Download references

Acknowledgment

Th work was financially supported by the Applied Scientific Research Program (Grant P3-20170927122); Basic Grant VA-FA-F6-010 of the Academy of Sciences, Republic of Uzbekistan; a project of the National Science and Technology Minister of China, 2011BA105B05; and the CAS/SAFEA International Partnership Program for Creative Research Team.

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Authors and Affiliations

  1. Xinjiang Technical Institute of Physics and Chemistry, Central Asian Center of Drug Discovery and Development CAS, 830011, Urumqi, P. R. China

    Kh. I. Khasanova & H. A. Aisa

  2. PhD Scholar University of Chinese Academy of Sciences (UCAS), 80 Zhongguancun, East Rd, 100190, Beijing, P. R. China

    Kh. I. Khasanova

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

    K. A. Eshbakova, K. K. Turgunov & B. Tashkhodzhaev

Authors
  1. Kh. I. Khasanova
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  2. K. A. Eshbakova
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  3. K. K. Turgunov
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  4. B. Tashkhodzhaev
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  5. H. A. Aisa
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Correspondence to K. A. Eshbakova.

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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2020, pp. 343–347.

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Khasanova, K.I., Eshbakova, K.A., Turgunov, K.K. et al. α- and γ-Apienes, Ferovinal, and Ferocin from Ferula ovina. Chem Nat Compd 56, 395–399 (2020). https://doi.org/10.1007/s10600-020-03045-8

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  • DOI: https://doi.org/10.1007/s10600-020-03045-8

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