The isolation of bioactive compounds from natural sources is a growing field, in particular due to its potential application in pharmacology and biotechnology. The relevance of this research was the driver to design a full-semester undergraduate analytical laboratory course to introduce students to advanced analytical and spectroscopic techniques while simultaneously exposing them to problems solved by modern research. The students extracted and characterized a biologically active compound from bacteria isolated from mangrove forest sediments. The bacterium, Vibrio sp. SKC6, was grown in a teaching laboratory setting, its intracellular fraction extracted via liquid-liquid extraction and further purified by high-performance liquid chromatography (HPLC), and assayed for bioactivity using a phenotypic profiling approach of a human cell line (HeLa). One of the HPLC fractions resulted in cell division arrest after DNA replication. The structure of the compound responsible for the observed bioactivity was characterized using mass spectrometry (UHPLC/ESI QToF-MS), 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and X-Ray single crystal diffraction analyses. This molecule was identified as pyridine-2,6-dicarboxylic acid, commonly known as dipicolinic acid (DPA), which is thought to be responsible for the thermotolerance of bacterial endospores. The findings from this course were summarized in a collaborative report written by each group of students that conformed to the format of the Journal of Natural Products. A unique, broad combination of analytical and biochemical methods makes this project attractive to students considering further careers in chemistry, chemical biology and pharmaceutical drug discovery.

Analytical chemistry project: Isolation of biologically active compounds from mangrove sediments

2019 Spring National Meeting

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