Isolation, Identification, and Investigation of a Novel Bioactive Furanocoumarin from Leaves of Amyris elemifera
Date of Award
Chemistry and Biochemistry
Plants produce biologically active compounds that humans have utilized for many agricultural applications. Amyris elemifera was investigated due to the known bioactivity of its family, Rutaceae, and its use in medicines in tribes of the Bahamas. Biotage® and TLC guided fractionation of the EtOAc, hexane, and MeOH extracts of the leaves of Amyris elemifera yielded bioactive compounds. Most significantly, a novel furanocoumarin, 8-(3-methylbut-2-enyloxy)-marmesin acetate (1), and its analog 8-(3-methylbut-2-enyloxy)-marmesin (2), were isolated. The structures were identified via NMR and X-ray crystallography techniques; the X-ray crystal structure for 1 was reported for the first time, and the data confirmed an absolute configuration of S at the chiral C-2’ for both compounds, which had not been reported previously for 2. Both were tested for activity against monocots, dicots, and fungi. The compounds hindered growth of Lactuca sativa (lettuce) and Agrostis stolonifera. A Lemna paucicostata phytotoxicity bioassay reported IC50 values for 1 and 2 as 26.2μM and 102μM respectively, and 1 showed antifungal activity against Colletotrichum fragariae in a TLC bioautography. The mechanism of phytotoxicity was shown to be membrane function related from the results of a cellular leakage assay. In a comparison of bioactivity between 1 and limonene, 1 unexpectedly showed more inhibition on fungal and bacterial species tested.
Bracken, Amy K., "Isolation, Identification, and Investigation of a Novel Bioactive Furanocoumarin from Leaves of Amyris elemifera" (2020). Honors Theses. 1324.
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