A new lactam, 5-hydroxy-1-[(4-hydroxyphenyl)methyl]-2-pyrrolidinone (1), was isolated from the ethyl acetate extract of Cannabis sativa L. The structure was established by spectroscopic analyses, including 1D and 2D NMR (1H, 13C, COSY, HMBC, HSQC) and EI-MS, and comparison with the data of known analogs.
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T. T. Guo, Q. C. Liu, P. B. Hou, F. H. Li, S. D. Guo, W. G. Song, H. Zhang, X. Y. Liu, S. Y. Zhang, J. C. Zhang, C. T. Ho, and N. S. Bai, Food Funct., 9, 6608 (2018).
S. D. Banister, J. C. Arnold, M. Connor, M. Glass, and I. S. McGregor, ACS Chem. Neurosci., 10, 2160 (2019).
M. A. ElSohly, M. M. Radwan, W. Gul, S. Chandra, and A. Galal, Prog. Chem. Org. Nat. Prod., 103, 1 (2017).
M. A. Elsohly and D. Slade, Life Sci., 78, 539 (2005).
M. M. Radwan, M. A. ElSohly, A. T. El-Alfy, S. A. Ahmed, D. Slade, A. S. Husni, S. P. Manly, L. Wilson, S. Seale, S. J. Cutler, and S. A. Ross, J. Nat. Prod., 78, 1271 (2015).
Y. F. Zhou, S. S. Wang, H. X. Lou, and P. H. Fan, Phytochem. Lett., 23, 57 (2018).
C. Citti, P. Linciano, F. Russo, L. Luongo, M. Iannotta, S. Maione, A. Lagana, A. L. Capriotti, F. Forni, M. A. Vandelli, G. Gigli, and G. Cannazza, Sci. Rep., 9, 20335 (2019).
Y. Nalli, P. Arora, S. R. Hassan, and A. Ali, Tetrahedron Lett., 59, 2470 (2018).
K. A. Rea, J. A. Casaretto, M. S. Al-Abdul-Wahid, A. Sukumaran, J. Geddes-McAlister, S. J. Rothstein, and T. A. Akhtar, Phytochemistry, 164, 162 (2019).
G. Chianese, A. Lopatriello, A. Schiano-Moriello, D. Caprioglio, D. Mattoteia, E. Benetti, D. Ciceri, L. Arnoldi, E. Combarieu, R. M. Vitale, P. Amodeo, G. Appendino, L. Petrocellis, and O. Taglialatela-Scafati, J. Nat. Prod., 83, 2727 (2020).
F. Zulfiqar, S. A. Ross, D. Slade, S. A. Ahmed, M. M. Radwan, Z. Ali, I. A. Khan, and M. A. ElSohly, Tetrahedron Lett., 53, 3560 (2012).
A. Pagani, F. Scala, G. Chianese, G. Grassi, G. Appendino, and O. Taglialatela-Scafati, Tetrahedron, 67, 3369 (2011).
J. Li, G. Wang, Y. Qin, X. Zhang, H. F. Wang, H. W. Liu, L. J. Zhu, and X. S. Yao, RSC Adv., 10, 32043 (2020).
Y. H. Choi, A. Hazekamp, A. M. Peltenburg-Looman, M. Frederich, C. Erkelens, A. W. Lefeber, and R. Verpoorte, Phytochem. Anal., 15, 345 (2004).
V. Kitryte, D. Bagdonaite, and R. P. Venskutonis, Food Chem., 267, 420 (2018).
L. L. Anderson, I. K. Low, S. D. Banister, I. S. McGregor, and J. C. Arnold, J. Nat. Prod., 82, 3047 (2019).
C. Liu, H. Ma, A. L. Slitt, and N. P. Seeram, J. Nat. Prod., 83, 2025 (2020).
T. T. Guo, J. C. Zhang, H. Zhang, Q. C. Liu, Y. Zhao, Y. F. Hou, L. Bai, L. Zhang, X. Q. Liu, X. Y. Liu, S. Y. Zhang, and N. S. Bai, J. Asian Nat. Prod. Res., 19, 793 (2017).
C. Citti, P. Linciano, F. Russo, L. Luongo, M. Iannotta, S. Maione, A. Lagana, A. L. Capriotti, F. Forni, M. A. Vandelli, G. Gigli, and G. Cannazza, Sci. Rep., 9, 20335 (2019).
G. N. Ding, B. Lu, Y. Y. Li, J. Wan, Z. G. Zhang, and X. M. Xie, Adv. Synth. Catal., 357, 1013 (2015).
Acknowledgment
This work was supported by the Innovation and Technology Project of Qiqihar University Graduate Student under Grant No. YJSCX2019030; Scientific research items of basic research business in Heilongjiang Provincial Higher Education Institutions under Grant No. 135309301.
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Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2022, pp. 513–514.
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Wang, JL., Liu, ZH., Zhao, YN. et al. A New Lactam from Cannabis sativa. Chem Nat Compd 58, 601–603 (2022). https://doi.org/10.1007/s10600-022-03750-6
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DOI: https://doi.org/10.1007/s10600-022-03750-6