Morphinan alkaloids from the leaves of Alphonsea cylindrica and their antibacterial properties

Cho, Kin-Hau and Tan, Siow-Ping and Tan, Hui-Yin and Liew, Sook Yee and Nafiah, Mohd Azlan (2023) Morphinan alkaloids from the leaves of Alphonsea cylindrica and their antibacterial properties. Planta Medica, 89 (01). pp. 79-85. ISSN 0032-0943, DOI https://doi.org/10.1055/a-1797-0548.

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Abstract

A phytochemical study has been carried out on CH (2) Cl (2) extract of Alphonsea cylindrica leaves, resulting in the isolation of three new morphinan alkaloids. They are kinomenine ( 1 ), N -methylkinomenine ( 2 ), and hydroxymethylkinomenine ( 3 ). The structures of these compounds were elucidated by extensive spectroscopic analysis (1D and 2D NMR, IR, UV, HRESIMS) and comparison with the data reported in literature for similar alkaloids. Kinomenine ( 1 ) and N -methylkinomenine ( 2 ) showed weak inhibition against S. aureus (MIC values of 1 and 2 = 500 mu g/mL; pIC (50) values in 95% C. I. of: 1 = 2.9 to 3.0; 2 = 2.9 to 3.1), while kinomenine ( 1 ) also showed weak inhibition against E. coli (MIC values of 1 = 500 mu g/mL; pIC (50) value in 95% C. I. of: 1 = 2.9) by broth microdilution method. The results obtained can be used as future referencefor the discovery of morphinans and the potential of A. cylindrica as an antibacterial source.

Item Type: Article
Funders: Tunku Abdul Rahman University College Internal Research Grant (Grant No: UC/I/G2017-00022), Universiti Malaya Research Grant (Grant No: GPF039A-2020)
Uncontrolled Keywords: Annonaceae; Alphonsea cylindrica; Morphinan alkaloids; Kinomenine; Antibacterial properties
Subjects: R Medicine > RM Therapeutics. Pharmacology
S Agriculture > S Agriculture (General)
Divisions: Centre for Foundation Studies in Science > Chemistry Division
Centre for Natural Products Research and Drug Discovery (CENAR)
Depositing User: Ms Zaharah Ramly
Date Deposited: 30 Nov 2023 04:56
Last Modified: 30 Nov 2023 04:56
URI: http://eprints.um.edu.my/id/eprint/38980

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