A new compound, commikuanoid D, was isolated from the ethyl acetate fraction of Commiphora kua resin. The structure was unambiguously elucidated on the basis of complete spectroscopic analysis. Furthermore, the compound displayed potent carbonic anhydrase II inhibition with IC50 of 17.4 ± 0.32 μM. On the other hand, the molecular docking reflected that the acetyl group of the molecule specifically binds with the Zn ion at the active site of CA-II, and the OH group of the compound mediated hydrogen bonding with Gln92, thus blocking the enzyme activity with a good binding score (≥ 7 kcal/mol).
Similar content being viewed by others
References
I. Hedberg and S. Edwards, Flora of Ethiopia, Vol. 3, Addis Ababa, Ethiopia, National Herbarium, Biology Dept., Science Faculty, Addis Ababa University, 1989.
R. A. Mothana, A. J. Al-Rehaily, and W. Schultze, Molecules, 15, 68 (2010).
T. Shen, G. H. Li, X. N. Wang, and H. X. Lou, J. Ethnopharmacol., 142, 319 (2012).
T. Shen, H. Q. Yuan, W. Z. Wan, X. L. Wang, X. N. Wang, M. Ji, and H. X. Lou, J. Nat. Prod., 71, 81 (2008).
T. Shen, W. Wan, H. Yuan, F. Kong, H. Guo, P. Fan, and H. Lou, Phytochemistry, 68, 1331 (2007).
A. Miller and M. Morris, Ethnoflora of the Socotra Archipelago, Royal Botanic Garden Edinburgh, United Kingdom, 2004.
L. O. A. Manguro, I. Ugi, and P. Lemmen, Chem. Pharm. Bull., 51, 479 (2003).
N. A. A. Ali, M. Wurster, N. Arnold, U. Lindequis, and L. Wessjohan, Rec. Nat. Prod., 2, 70 (2008).
H. Ullah, A. Khan, N. U. Rehman, S. A. Halim, H. Khan, I. Khan, R. Csuk, A. Al-Rawahi, S. Al-Hatmi, and A. Al-Harrasi, J. Ethnopharmacol., 252, 112558 (2020).
A. Dekebo, E. Dagne, L. K. Hansen, O. R. Gautun, and A. J. Aasen, Phytochemistry, 59, 399 (2002).
M. Duwiejua, I. Zeitlin, P. Waterman, J. Chapman, G. Mhango, and G. Provan, Planta Medica, 59, 12 (1993).
G. J. Provan and P. G. Waterman, Phytochemistry, 25, 917 (1986).
G. J. Provan and P. G. Waterman, Phytochemistry, 27, 3841 (1988).
N. U. Rehman, S. A. Halim, A. Khan, M. Khan, S. Al-Hatmi, and A. Al-Harrasi, Fitoterapia, 157, 105125 (2022).
O. Koz, D. Ekinci, A. Perrone, S. Piacente, O. Alankus-Caliskan, E. Bedir, and C. T. Supuran, J. Enzyme Inhibit. Med. Chem., 28, 412 (2013).
S. Pastarekova, S. Parkkila, J. Pastorek, and C. Supuran, Therap. Appl. Future Prosp., 119, 199 (2004).
S. Ghorai, S. Pulya, K. Ghosh, P. Panda, B. Ghosh, and S. Gayen, Bioorg. Chem., 95, 103557 (2020).
M. Saleem, S. Hareem, A. Khan, S. Naheed, M. Raza, R. Hussain, M. Imran, and M. I. Choudhary, Pure Appl. Chem., 91, 1695 (2019).
N. U. Rehman, J. N. Alsabahi, T. Alam, A. Khan, K. Rafiq, M. Khan, and A. Al-Harrasi, J. Essent. Oil Bearing Plants, 24, 68 (2021).
E. Masini, F. Carta, A. Scozzafava, and C. T. Supuran, Exp. Opin. Therap. Patents, 23, 705 (2013).
K. Rafiq, M. Khan, N. Muhammed, A. Khan, N. U. Rehman, B. E. M. Al-Yahyaei, M. Khiat, S. A. Halim, Z. Shah, and R. Csuk, Med. Chem. Res., 30, 712 (2021).
S. K. Avula, N. U. Rehman, M. Khan, S. A. Halim, A. Khan, K. Rafiq, R. Csuk, B. Das, and A. Al-Harrasi, Med. Chem. Res., 30, 1185 (2021).
N. Ur Rehman, S. A. Halim, M. Khan, H. Hussain, H. Yar Khan, A. Khan, G. Abbas, K. Rafiq, and A. Al-Harrasi, Pharmaceuticals, 13, 94 (2020).
W. Herz, K. Watanabe, P. Kulanthaivel, and J. F. Blount, Phytochemistry, 24, 2645 (1985).
C. Kamperdick, T. P. Lien, G. Adam, and T. V. Sung, J. Nat. Prod., 66, 675 (2003).
C. B. Rogers, Phytochemistry, 49, 2069 (1998).
E. N. Happi, A. T. Tcho, J. C. Sirri, J. D. Wansi, B. Neumann, H. G. Stammler, J. Wandji, and N. Sewald, Phytochem. Lett., 5, 423 (2012).
Molecular Operating Environment (MOE), Chemical Computing Group ULC 1010 Sherbooke St. West, Suite# 910, Montreal QC, Canada, H3A 2R7, 2021.
Acknowledgment
The authors are thankful to The Oman Research Council (TRC) for their support through the Research Grant Program (BFP/RGP/CBS/21/002). The authors are also grateful to Mr. Saif Al Hatmi, Oman Botanic Garden, Oman, for the collection of C. kua resin.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2024, pp. 65–68.
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
Rehman, N.U., Halim, S.A., Khan, A. et al. Commikuanoid D: A New Potent Carbonic Anhydrase-II Inhibitor from the Resin of Commiphora kua. Chem Nat Compd 60, 75–79 (2024). https://doi.org/10.1007/s10600-024-04258-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-024-04258-x