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Communication

N-Methyl Costaricine and Costaricine, Two Potent Butyrylcholinesterase Inhibitors from Alseodaphne pendulifolia Gamb.

by
Muhammad Hafiz Husna Hasnan
1,†,
Yasodha Sivasothy
2,†,
Kooi Yeong Khaw
2,
Mohd Azlan Nafiah
3,
Hazrina Hazni
4,
Marc Litaudon
5,
Wan Adriyani Wan Ruzali
1,
Sook Yee Liew
1,4,* and
Khalijah Awang
4,6,*
1
Chemistry Division, Centre for Foundation Studies in Science, Universiti Malaya, Kuala Lumpur 50603, Malaysia
2
School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway 47500, Malaysia
3
Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjung Malim 35900, Malaysia
4
Centre for Natural Products Research and Drug Discovery (CENAR), Universiti Malaya, Kuala Lumpur 50603, Malaysia
5
Institut de Chimie des Substances Naturelles, CNRS, UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France
6
Department of Chemistry, Faculty of Science, Universiti Malaya, Kuala Lumpur 50603, Malaysia
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Int. J. Mol. Sci. 2023, 24(13), 10699; https://doi.org/10.3390/ijms241310699
Submission received: 2 June 2023 / Revised: 19 June 2023 / Accepted: 24 June 2023 / Published: 27 June 2023
(This article belongs to the Special Issue Natural Product Chemistry and Biological Research)
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Abstract

Studies have been conducted over the last decade to identify secondary metabolites from plants, in particular those from the class of alkaloids, for the development of new anti-Alzheimer’s disease (AD) drugs. The genus Alseodaphne, comprising a wide range of alkaloids, is a promising source for the discovery of new cholinesterase inhibitors, the first-line treatment for AD. With regard to this, a phytochemical investigation of the dichloromethane extract of the bark of A. pendulifolia Gamb. was conducted. Repeated column chromatography and preparative thin-layer chromatography led to the isolation of a new bisbenzylisoquinoline alkaloid, N-methyl costaricine (1), together with costaricine (2), hernagine (3), N-methyl hernagine (4), corydine (5), and oxohernagine (6). Their structures were elucidated by the 1D- and 2D-NMR techniques and LCMS-IT-TOF analysis. Compounds 1 and 2 were more-potent BChE inhibitors than galantamine with IC50 values of 3.51 ± 0.80 µM and 2.90 ± 0.56 µM, respectively. The Lineweaver–Burk plots of compounds 1 and 2 indicated they were mixed-mode inhibitors. Compounds 1 and 2 have the potential to be employed as lead compounds for the development of new drugs or medicinal supplements to treat AD.
Keywords: Alseodaphne pendulifolia Gamb.; Lauraceae; alkaloid; bisbenzylisoquinoline; aporphine; oxoaporphine; acetylcholinesterase; butyrylcholinesterase Alseodaphne pendulifolia Gamb.; Lauraceae; alkaloid; bisbenzylisoquinoline; aporphine; oxoaporphine; acetylcholinesterase; butyrylcholinesterase

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MDPI and ACS Style

Husna Hasnan, M.H.; Sivasothy, Y.; Khaw, K.Y.; Nafiah, M.A.; Hazni, H.; Litaudon, M.; Wan Ruzali, W.A.; Liew, S.Y.; Awang, K. N-Methyl Costaricine and Costaricine, Two Potent Butyrylcholinesterase Inhibitors from Alseodaphne pendulifolia Gamb. Int. J. Mol. Sci. 2023, 24, 10699. https://doi.org/10.3390/ijms241310699

AMA Style

Husna Hasnan MH, Sivasothy Y, Khaw KY, Nafiah MA, Hazni H, Litaudon M, Wan Ruzali WA, Liew SY, Awang K. N-Methyl Costaricine and Costaricine, Two Potent Butyrylcholinesterase Inhibitors from Alseodaphne pendulifolia Gamb. International Journal of Molecular Sciences. 2023; 24(13):10699. https://doi.org/10.3390/ijms241310699

Chicago/Turabian Style

Husna Hasnan, Muhammad Hafiz, Yasodha Sivasothy, Kooi Yeong Khaw, Mohd Azlan Nafiah, Hazrina Hazni, Marc Litaudon, Wan Adriyani Wan Ruzali, Sook Yee Liew, and Khalijah Awang. 2023. "N-Methyl Costaricine and Costaricine, Two Potent Butyrylcholinesterase Inhibitors from Alseodaphne pendulifolia Gamb." International Journal of Molecular Sciences 24, no. 13: 10699. https://doi.org/10.3390/ijms241310699

APA Style

Husna Hasnan, M. H., Sivasothy, Y., Khaw, K. Y., Nafiah, M. A., Hazni, H., Litaudon, M., Wan Ruzali, W. A., Liew, S. Y., & Awang, K. (2023). N-Methyl Costaricine and Costaricine, Two Potent Butyrylcholinesterase Inhibitors from Alseodaphne pendulifolia Gamb. International Journal of Molecular Sciences, 24(13), 10699. https://doi.org/10.3390/ijms241310699

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