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Planta Med 2023; 89(01): 79-85
DOI: 10.1055/a-1797-0548
Natural Product Chemistry and Analytical Studies
Original Papers

Morphinan Alkaloids from the Leaves of Alphonsea cylindrica and Their Antibacterial Properties

Kin-Hau Cho
1   Department of Physical Science, Faculty of Applied Sciences, Tunku Abdul Rahman University College, Kuala Lumpur, Malaysia
,
Siow-Ping Tan 
1   Department of Physical Science, Faculty of Applied Sciences, Tunku Abdul Rahman University College, Kuala Lumpur, Malaysia
,
Hui-Yin Tan
2   Faculty of Applied Sciences, Tunku Abdul Rahman University College, Kuala Lumpur, Malaysia
,
Sook Yee Liew
3   Chemistry Division, Centre for Foundation Studies in Science, Universiti Malaya, Kuala Lumpur, Malaysia
4   Centre for Natural Products Research and Drug Discovery (CENAR), Universiti Malaya, Kuala Lumpur, Malaysia
,
Mohd Azlan Nafiah
5   Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim, Perak, Malaysia
› Author AffiliationsSupported by: Tunku Abdul Rahman University College Internal Grant UC/I/G2017-00022
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Abstract

A phytochemical study has been carried out on CH2Cl2 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 µg/mL; pIC50 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 µg/mL; pIC50 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.

Key words

Annonaceae - Alphonsea cylindrica - morphinan alkaloids - kinomenine - antibacterial properties

Supporting Information

    NMR spectra of compounds 1–3, HRESIMS data and dose-response curve of tested compounds are available as Supporting Information.

  • Supporting Information


Publication History

Received: 12 October 2021

Accepted after revision: 14 March 2022

Accepted Manuscript online:
14 March 2022

Article published online:
06 May 2022

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