New 1-hydroxy-1-en-3-one derivatives of 18β- and 18α-glycyrrhetic acids were synthesized via oxidation of the 3-ketotriterpenoids by atmospheric oxygen in the presence of an excess of t-BuOK. 2-Hydroxy-3,11-dioxo-18αH-olean-1,12-dien-30-oic acid exhibited pronounced hypoglycemic activity and decreased the blood glucose concentration by 42.7% compared with a control after 120 min at a dose of 50 mg/kg in a rat alloxan-induced diabetes model.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M.-C. Yin, BioMedicine, 2, 2 (2012).
A. Alqahtani, K. Hamid, A. Kam, K. H. Wong, Z. Abdelhak, V. Razmovski-Naumovski, K. Chan, K. M. Li, P. W. Groundwater, and G. Q. Li, Curr. Med. Chem., 20, 908 (2013).
J. Chen, J. Lin, L. Zhang, G. Wu, W. Hua, X. Wu, and H. Sun, Bioorg. Med. Chem. Lett., 16, 2915 (2006).
X. Wen, J. Xia, K. Cheng, L. Zhang, P. Zhang, J. Liu, L. Zhang, P. Ni, and H. Sun, Bioorg. Med. Chem. Lett., 17, 5777 (2007).
X.-Z. Tang, T. Guan, Y.-S. Qian, Y.-M. Li, H.-B. Sun, J.-H. Huang, and Y. Zhang, Chin. J. Nat. Med., 6, 0053 (2008).
K. Cheng, P. Zhang, J. Liu, and H. Sun, J. Nat. Prod., 71, 1877 (2008).
J. Hao, P. Zhang, X. Wen, and H. Sun, J. Org. Chem., 73, 7405 (2008).
K. Yamada, M. Hosokawa, S. Fujimoto, H. Fujiwara, Y. Fujita, N. Harada, C. Yamada, M. Fukushima, N. Ueda, T. Kaneko, F. Matsuyama, Y. Yamada, Y. Seino, and N. Inagaki, Diabetes Res. Clin. Pract., 80, 48 (2008).
G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, and T. G. Tolstikova, Licorice: Biodiversity, Chemistry, and Use in Medicine [in Russian], Akademicheskoe Izd. Geo, Novosibirsk, 2007, 311 pp.
P. Kalaiarasi and K. V. Pugalendi, Eur. J. Pharm., 606, 269 (2009).
G. A. Tolstikov and M. I. Goryaev, Glycyrrhetic Acid [in Russian], Izd. Nauka Kaz. SSR, Alma-Ata, 1966, 93 pp.
A. N. Mironov (ed.), Handbook for Preclinical Drug Trials, Part 1, Grif i K, Moscow, 2012, p. 670.
E. Pretsch, P. Buhlmann, and C. Affolter, Structure Determination of Organic Compounds, Springer, Berlin, New York, 2000.
L. R. Mikhailova, L. A. Baltina, R. M. Kondratenko, O. Kunert, L. V. Spirikhin, F. Z. Galin, and G. A. Tolstikov, Chem. Nat. Compd., 42, 553 (2006).
G. A. Tolstikov, L. M. Khalilov, L. A. Baltina, R. M. Kondratenko, A. A. Panasenko, and E. V. Vasileva, Chem. Nat. Compd., 21, 605 (1986).
A. J. Gordon and R. A. Ford, A Chemist’s Companion, Wiley-Interscience, New York, 1972.
O. V. Stolyarova, L. A. Baltina, Jr., L. R. Mikhailova, T. M. Gabbasov, L. A. Baltina, and G. A. Tolstikov, Khim. Interesakh Ustoich. Razvit., 16, 571 (2008).
M. L. Belenkii, Elements of Quantitative Assay of the Pharmacological Effect [in Russian], Medgiz, Leningrad, 1963, 151 pp.
Acknowledgment
The work was supported financially by the RFBR (Grant 11-03-00462a).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2014, pp. 908–911.
Rights and permissions
About this article
Cite this article
Baltina, L.A., Budaev, A.S., Mikhailova, L.R. et al. New Stereoisomeric Glycyrrhetic Acid Derivatives and their Hypoglycemic Activity. Chem Nat Compd 50, 1042–1046 (2014). https://doi.org/10.1007/s10600-014-1155-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-014-1155-x