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

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.

Biological Secondary Metabolites from the Lumnitzera littorea-Derived Fungus Penicillium oxalicum HLLG-13

“…Compounds 1 – 4 were cyclopiane diterpenes with a unique 6/5/5/5 tetracyclic skeleton, and this type of compound is very rarely found from a natural source. Only thirteen compounds have been found in the existing literature, and most of them were mainly isolated as secondary metabolites from the genus of Penicillum [ 13 , 26 , 27 , 28 , 29 , 30 ].…”

Quinones: Biosynthesis, Characterization of 13C Spectroscopical Data and Pharmacological Activities

“…The study confirms that the positions of substituents directly influence the structure-activity relation. Naphthofuranquinone, glycoquinone and avicequinone C showed antiparasitic effect against Trypanosoma brucei, [41] and phenanthraquinones, burmanin A, B and C, on Leishmania spp. [48] Quinones, with established potential, such as atovaquone and ubiquinone, which share structural similarities, act to inhibit the cytochrome bc1 complex of the mitochondrial respiratory chain, which results in loss of mitochondrial function in Plasmodium spp.…”

“…Avicennia marina (Forssk.) Vierh [40] 13 C NMR (100 MHz, CDCl Avicennia lanata Ridl [41] 13 C NMR (100.5 MHz, CDCl 3 ): δc 173.5 (C-1), 151.7 (C-2), 131.4 (C-3), 180.9 (C-4), 133.3 (C-4a), 126.9 (C-5), 133.9 (C-6), 133.9 (C-7), 127.…”

Exploring the Mangrove Fruit: From the Phytochemicals to Functional Food Development and the Current Progress in the Middle East

“…Those bioactivities are assumed from the metabolite contents within the plant. Naphthofuranquinone with intense anti-trypanosomal activity is found in the twigs of A. lanata [ 30 ], while proanthocyanidins from leaves of Ceriops tagal show solid antioxidant activities [ 31 ]. Unfortunately, only 27 species of mangrove have been traditionally used [ 32 ].…”