Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant Avicennia lanata.

Noor Wini Mazlan,Ruangelie Edrada-Ebel,Carol Clements

doi:10.3390/md18120661

Noor Wini Mazlan, Ruangelie Edrada-Ebel + Show 1 more

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https://doi.org/10.3390/md18120661

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Abstract

The discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the crude organic extract of the mangrove plant Avicennia lanata collected from the east coast of Peninsular Malaysia in the Setiu Wetlands, Terengganu, using HRESI-LCMS-based metabolomics-guided isolation and fractionation. Isolation work on the crude extract A. lanata used high-throughput chromatographic techniques to give two new naphthofuranquinone derivatives, hydroxyavicenol C (1) and glycosemiquinone (2), along with the known compounds avicenol C (3), avicequinone C (4), glycoquinone (5), taraxerone (6), taraxerol (7), β-sitosterol (8) and stigmasterol (9). The elucidation and identification of the targeted bioactive compounds used 1D and 2D-NMR and mass spectrometry. Except for 6–9, all isolated naphthoquinone compounds (1–5) from the mangrove plant A. lanata showed significant anti-trypanosomal activity on Trypanosoma brucei brucei with MIC values of 3.12–12.5 μM. Preliminary cytotoxicity screening against normal prostate cells (PNT2A) was also performed. All compounds exhibited low cytotoxicity, with compounds 3 and 4 showing moderate cytotoxicity of 78.3% and 68.6% of the control values at 100 μg/mL, respectively.

Highlights

Mangrove plants as well as their endophytic fungi exhibit unique chemical diversity from various classes of compounds with promising biological activities [1,2,3]
The dereplication studies revealed that the plant extract possessed certain types of compounds, such as alkaloids, triterpenes and naphthoquinones, which have previously been isolated from different Avicennia species, A. marina and A. alba
The main aims in the present work were to isolate secondary metabolites for anti-trypanosomal derived drugs from the mangrove plant, Avicennia lanata by utilising metabolomics and bioassays-guided approaches to aid in the preliminary screening, fractionation and purification of the targeted bioactive compounds

Summary

Introduction

Mangrove plants as well as their endophytic fungi exhibit unique chemical diversity from various classes of compounds with promising biological activities [1,2,3]. Avicennia lanata (synonym: A. rumphiana), locally known in Malaysia as ‘Api-api bulu’, is found mainly in sandy or firm silt substrate of middle to higher intertidal zones [5]. It is native and common throughout much of Peninsular Malaysia, Philippines and New Guinea. This tree is identified by its furry underside leaves and fruit. The pelt (‘bulu’ in Malay) on the leaves conserves water by trapping a layer of insulating air, reducing water loss through evaporation

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