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Talip, Azziz, Wong, Awang, Naz, Bakri, Ahmad, and Litaudon: New Azafluorenone Derivative and Antibacterial Activities of Alphonsea cylindrica Barks
Original Article

Natural Product Sciences 2017;23(3):151-156.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.3.151

New Azafluorenone Derivative and Antibacterial Activities of Alphonsea cylindrica Barks

Munirah Abdul Talip1, Saripah Salbiah Syed Abdul Azziz1, ∗, Chee Fah Wong2, Khalijah Awang3, Humera Naz4, Yuhanis Mhd Bakri1, Mohamad Syahrizal Ahmad1, Marc Litaudon5

1Department of Chemistry, Faculty of Science and Mathematics, Sultan Idris Education University, 35900 Tanjung Malim, Perak Darul Ridzuan, Malaysia

2Department of Biology, Faculty of Science and Mathematics, Sultan Idris Education University, 35900 Tanjung Malim, Perak Darul Ridzuan, Malaysia

3Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia

4Atta-ur-Rahman Institute of Natural Product Discovery and Faculty of Pharmacy, University Technology MARA, Puncak Alam, 42300 Selangor, Malaysia

5Centre de Recherche de Gif, Institute de Chimie des Substances Naturelles, CNRS, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France

∗Author for correspondence Saripah Salbiah Syed Abdul Azziz, Department of Chemistry, Faculty of Science and Mathematics, Sultan Idris Education University, 35900 Tanjung Malim, Perak Darul Ridzuan, Malaysia Tel: +6015-48117313; E-mail: saripah@fsmt.upsi.edu.my

Received 16 March 2017       Revised 24 April 2017       Accepted 2 May 2017

Copyright © 2017 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A phytochemical study of Alphonsea cylindrica King (unreported) has led to the isolation of six alkaloids. The compounds were identified as kinabaline (1; azafluorenone alkaloid), muniranine (2), O-methylmoschatoline (3; oxoaporphine alkaloid), lysicamine (4), atherospermidine (5) and N-methylouregidione (6; 4, 5-dioxoaporphine alkaloid). The structures of the isolated compounds were determined based on the spectroscopic techniques and by comparison with data reported in the literature. Alkaloid 2 was isolated as a new derivative of azafluorenone while alkaloids 1, 3 – 6 were isolated for the first time from Alphonsea species. In addition, alkaloid 3 and 4 showed inhibition zone against Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus cereus in disc diffusion test. The minimum inhibition concentration (MIC) values of lysicamine (4) against S. aureus, B. cereus and P. aeruginosa were found to be smaller than O-methylmoschatoline (3). Therefore, the reported antibacterial activity showed the potential of this plant as natural antibacterial agent and supported the documented traditional use of Alphonsea sp. in the treatment of diarrhea and fever.

Keywords: Alphonsea, Alkaloids, Antibacterial, Disc diffusion test, MIC

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Fig. 1.
(a) Herbarium of A. cylindrica; (b) Fruits of A. cylindrica.
nps-23-151f1.tif
Fig. 2.
Structures of alkaloids 1 – 6.
nps-23-151f2.tif
Fig. 3.
HMBC, COSY and NOESY correlations of 2.
nps-23-151f3.tif
Table 1.
NMR spectroscopic data for alkaloids 1 and 2 in CDCl3 (500 MHz 1H and 125 MHz 13C)
Position Muniranine (2)
δ13C δ1H HMQC HMBC COSY δ13C δH HMQC HMBC COSY
1 146.9         147.2        
2 125.2 6.94 (d, J =5.0Hz, 1H) H-2 CH3-1, C3, C-9a H-3 124.7 6.89 (d, J = 5.0 Hz, 1H) H-2 CH3-1, C3, C9a H-3
3 152.8 8.50 (d, J =5.0Hz, 1H) H-3 C1, C2, C4a H-2 153.0 8.45 (d, J = 5.0 Hz, 1H) H-3 C1, C2, C4a H-2
4a 163.4     −   164.0     −  
4b 111.0     −   113.8     −  
5 162.5     −   154.7     −  
6 155.8     −   148.8     −  
7 101.8 6.32 (s, 1H) H-7 C4b, C8a, C8, C6, C5   143.8     −  
8 140.0     −   144.0     −  
8a 131.7     −   127.9     −  
9 194.0     −   194.8     −  
9a 127.7     −   127.0        
OCH3-5 56.7 3.91 (s, 3H)   C5   61.8 4.01 (s, 3H)   C5  
OCH3-7 – –   −   61.5 3.98 (s, 3H)   C7, C8  
OCH3-8 62.0 3.99 (s, 3H)   C8   62.2 4.04 (s, 3H)      
CH3-1 17.3 2.61 (s, 3H)   C1, C2, C9a   17.4 2.59 (s, 3H)   C1, C2, C9a  
OH-6 – 8.81 (br s, 1H)   C6, C4b, C7   – 8.71 (br s, 1H)   C4b, C5, C6, C7, C8  
Table 2.
Diameter zone of inhibition for alkaloids 1 – 6 against S. aureus, B. cereus, S.typhi, E. coli and P. aeruginosa
Alkaloids Inhibition zone (mm) ± SE
S. aureus B. cereus S. typhi E. coli P. aeruginosa
1 − − − − −
2 − − − − −
3 8.33 ± 0.58 9.33 ± 0.58 − − 9.67 ± 0.58
4 11.33 ± 0.58 10.00 ± 1.00 − − 13.33 ± 1.53
5 − − − − −
6 − − − − −
Table 3.
MIC of alkaloids 3 and 4 against S. aureus, B. cereus and P. aeruginosa
Alkaloids MIC value (μg/ml)
S. aureus B. cereus P. aeruginosa
3 800 800 500
4 125 250 125
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