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

• Published in: Marine drugs 2020-12, Vol.18 (12), p.661
• Main Authors: Mazlan, Noor Wini, Clements, Carol, Edrada-Ebel, RuAngelie
• Format: Article
• Language: English
• Subjects: Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; Avicennia; Avicennia lanata; Bioactive compounds; Biocompatibility; Biological activity; Cell Line; Chromatography; Cytotoxicity; dereplication; Discriminant analysis; Disease; Drugs; Fractionation; Furans - isolation & purification; Furans - pharmacology; Humans; mangrove; Mangroves; Mass spectrometry; Mass spectroscopy; metabolic profiling; Metabolism; Metabolites; Metabolomics; Multivariate analysis; Naphthoquinones - isolation & purification; Naphthoquinones - pharmacology; Natural products; NMR; Nuclear magnetic resonance; Plant extracts; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Principal components analysis; Prostate; Quinones; Secondary metabolites; Toxicity; Trypanosoma brucei brucei - drug effects; Trypanosoma brucei brucei - physiology
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md18120661

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 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 used high-throughput chromatographic techniques to give two new naphthofuranquinone derivatives, hydroxyavicenol C ( ) and glycosemiquinone ( ), along with the known compounds avicenol C ( ), avicequinone C ( ), glycoquinone ( ), taraxerone ( ), taraxerol ( ), β-sitosterol ( ) and stigmasterol ( ). The elucidation and identification of the targeted bioactive compounds used 1D and 2D-NMR and mass spectrometry. Except for , all isolated naphthoquinone compounds ( ) from the mangrove plant showed significant anti-trypanosomal activity on 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 and showing moderate cytotoxicity of 78.3% and 68.6% of the control values at 100 μg/mL, respectively.