4-{[2-(Methoxycarbonyl)phenyl]amino}-2-methyl-4-oxobutanoic acid amide, the diterpenoid alkaloid delavaine B, and the new talassamine-type alkaloid 15-epinaviculine B were isolated for the first time from the aerial part of Delphinium oreophilum Huth. The structures of the compounds were elucidated using 1D and 2D NMR spectroscopy, mass spectrometry, and an X-ray crystal structure analysis for the new alkaloid. The stereochemistry of the talassamine framework and H-bonds in the crystal of 15-epinaviculine B were analyzed.
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H. I. Ahunova, Sh. V. Abdullaev, and M. Rajabova, Sci. Newsl. NamSU, 6, 81 (2019).
H. I. Ahunova, T. A. Sattarov, and Sh. V. Abdullaev, Sci. Newsl. NamSU, 10, 115 (2020).
Kh. I. Akhunova, K. K. Turgunov, Kh. M. Bobakulov, B. Tashkhodzhaev, A. I. Kulonov, and Sh. V. Abdullaev, Chem. Nat. Compd., 59, 339 (2023).
G.-Q. Li, Y.-Y. Li, Y.-T. Zhao, Q.-P. Xu, Y.-L. Li, and G.-C. Wang, Z. Kristallogr.-New Cryst. Struct., 234, 521 (2019).
S. W. Pelletier, F. M. Harraz, M. M. Badawi, S. Tantiraksachai, F. P. Wang, and S. Y. Chen, Heterocycles, 24, 1853 (1986).
J.-X. Cao, L.-B. Li, J. Ren, S.-P. Jiang, R.-R. Tian, X.-L. Chen, S.-L. Peng, J. Zhang, and H.-J. Zhu, Helv. Chim. Acta, 91, 1954 (2008).
Q. Zhang, Z. Yang, Q. Wang, S. Liu, T. Zhou, Y. Zhao, and M. Zhang, J. Am. Chem. Soc., 143, 7088 (2021).
A. A. Nishanov, M. N. Sultankhodzhaev, I. M. Yusupova, M. S. Yunusov, and B. Tashkhozhaev, Chem. Nat. Compd., 27, 82 (1991).
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. Van de Streek, J. Appl. Crystallogr., 39, 453 (2006).
G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Goettingen, Goettingen, 1996.
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).
G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem., 71, 3 (2015).
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The work was supported by the Budgetary Program for Basic Scientific Research of the Academy of Sciences of the Republic of Uzbekistan.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 959–962.
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Ahunova, H., Bobakulov, K.M., Turgunov, K.K. et al. Alkaloids from Delphinium oreophilum. The New Diterpene Alkaloid 15-Epinaviculine B. Chem Nat Compd 59, 1137–1141 (2023). https://doi.org/10.1007/s10600-023-04211-4
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DOI: https://doi.org/10.1007/s10600-023-04211-4