The alkaloid composition of Delphinium oreophilum Huth was studied. 14-Acetylbrowniine, browniine, delphatine, 14-acetyldelectinine, and isoboldine were isolated. The last four alkaloids were observed for the first time in this plant. All isolated compounds were identified using 1D and 2D NMR spectroscopy, mass spectrometry, and X-ray crystal structure analyses (XSAs). Differences in the stereochemistry of 14-acetylbrowniine and the base and salts were analyzed using XSAs. It was found that 14-acetylbrowniine possessed high anti-inflammatory activity and exhibited antioxidant properties.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Flora of Uzbekistan, [in Russian], Vol. II, Tashkent, 1953, pp. 447–460.
R. Shakirov, M. V. Telezhenetskaya, I. A. Bessonova, S. F. Aripova, I. A. Israilov, M. N. Sultankhodzhaev, V. I. Vinogradova, T. S. Tulyaganov, B. T. Salimov, and V. A. Tel′nov, Chem. Nat. Compd., 32, 216 (1996).
Sh. M. Adizov, B. T. Salimov, and B. Tashkhodzhaev, Chem. Nat. Compd., 49, 190 (2013).
K. Wada, E. Ohkoshi, S. L. Morris-Natschke, K. F. Bastow, and K. H. Lee, Bioorg. Med. Chem. Lett., 22, 249 (2012).
K. Wada, E. Ohkoshi, Y. Zhao, M. Goto, S. L. Morris-Natschke, and K. H. Lee, Bioorg. Med. Chem. Lett., 25, 1525 (2015).
H. I. Ahunova, Sh. V. Abdullaev, and M. Rajabova, Nauchn. Vestn. NamGU, No. 6, 81 (2019).
H. I. Ahunova, T. A. Sattarov, and Sh. V. Abdullaev, Nauchn. Vestn. NamGU, No. 10, 115 (2020).
S. W. Pelletier, N. V. Mody, R. S. Sawhney, and J. Bhattacharyya, Heterocycles, 7, 327 (1977).
B. T. Salimov, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 14, 84 (1978).
S. W. Pelletier and R. S. Sawhney, Heterocycles, 9, 463 (1978).
V. G. Kazlikhin, V. A. Tel′nov, M. S. Yunusov, and S. Yu. Yunusov, Chem. Nat. Compd., 13, 737 (1977).
L. D. Yakhontova, Chem. Nat. Compd., 3, 240 (1967).
A. H. Jackson and J. A. Martin, J. Chem. Soc. C, 2061 (1966).
S. W. Pelletier and K. I. Varughese, J. Nat. Prod., 47, 643 (1984).
Z. Zeng, G. Kociok-Kohn, T. J. Woodman, M. G. Rowan, and I. S. Blagbrough, Eur. J. Org. Chem., 2021, 2169 (2021).
B. Tashkhodzhaev, Chem. Nat. Compd., 46, 421 (2010).
G. M. Brown and L. H. Hall, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 33, 2051 (1977).
L. Krause, R. Herbs-Irmer, G. M. Sheldrick, and D. Stalke, J. Appl. Crystallogr., 48, 3 (2015).
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).
G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 71, 3 (2015).
G. Suganya, P. Sampath Kumar, B. Dheeba, and R. Sivakumar, Int. J. Pharm. Pharm. Sci., 6 (7), 342 (2014).
N. Abdullah Al-Dhabi, M. Valan Arasu, and T. S. Rejiniemon, Evidence-Based Complementary Altern. Med., Art. ID 164261, 1 (2015).
R. M. Yu, W. Yang, L. Y. Song, C. Y. Yan, Z. Zhang, and Y. Zhao, Carbohydr. Polym., 70, 430 (2007).
Acknowledgment
We thank Profs. J. J. Chen and C.-A. Geng (Laboratory of Phytochemistry and Plants Resources, Institute of Botany, AS, PRC) and D. Makhmudzhanov (Institute of Botany, AS, PRC) for assistance with the collection and identification of D. oreophilum.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2023, pp. 286–291.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Akhunova, K.I., Turgunov, K.K., Bobakulov, K.M. et al. Alkaloids from Delphinium oreophilum and Biological Activity of 14-Acetylbrowniine. Chem Nat Compd 59, 339–345 (2023). https://doi.org/10.1007/s10600-023-03989-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-023-03989-7