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Synthesis and evaluation of 29-norcycloartane triterpenoids as α-glucosidase inhibitors

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Abstract

A series of oxygen and nitrogen derivatives of 29-norcycloartane triterpenoids have been synthesized on the basis of cyclomusalenone isolated from Musa balbisiana Colla. The structures of new compounds have been established by an NMR spectroscopy analysis, and inhibitory activity against α-glucosidase was evaluated. Among tested compounds, 2,3-isoxazolocyclomusalenone is discovered as a new potent α-glucosidase inhibitor with IC50 value 20.4 μM being 30- and 20-fold more active than initial cyclomusalenone and marketed drug acarbose.

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Acknowledgments

This work was partially supported by the Russian Foundation for Basic Research [No.: 10-03-90303]; Vietnam Academy of Science and Technology (VAST) for International projects (2010–2011); Grant of the President of Russian Federation for support of young scientists [MK-5382.2013.3].

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center of Russian Academy of Sciences, 71, pr. Oktyabrya, Ufa, 450054, Russian Federation

    Irina E. Smirnova & Oxana B. Kazakova

  2. Institute of Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet Str., Cau Giay Dist., Hanoi, Vietnam

    Do Quoc Viet, Nguyen Thi Thuc, Pham Thuy Linh & Do Thi Thu Huong

Authors
  1. Irina E. Smirnova
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  2. Oxana B. Kazakova
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  3. Do Quoc Viet
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  4. Nguyen Thi Thuc
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  5. Pham Thuy Linh
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  6. Do Thi Thu Huong
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Correspondence to Irina E. Smirnova.

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Smirnova, I.E., Kazakova, O.B., Viet, D.Q. et al. Synthesis and evaluation of 29-norcycloartane triterpenoids as α-glucosidase inhibitors. Med Chem Res 24, 2177–2182 (2015). https://doi.org/10.1007/s00044-014-1292-6

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  • DOI: https://doi.org/10.1007/s00044-014-1292-6

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