Location: Natural Products Utilization ResearchTitle: A novel furanocoumarin with phytotoxic activity from the leaves of Amyris elemifera (Rutaceae)
|FRONCZEK, FRANK - Louisiana State University|
Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/4/2020
Publication Date: 12/24/2020
Citation: Meepagala, K.M., Bracken, A.K., Fronczek, F.R., Johnson, R.D., Wedge, D.E., Duke, S.O. 2020. A novel furanocoumarin with phytotoxic activity from the leaves of Amyris elemifera (Rutaceae). Journal of Agricultural and Food Chemistry. https://www.doi.org/10.1021/acsomega.0c04778.
Interpretive Summary: Amyris elemifera also known as sea torchwood is a plant in the Rtaceae family (citrus family). In our efforts to find natural product based agrochemicals, the ethyl acetate extract of the leaves of A. elemifera was studied. A new herbicidal compound and an analog of it were isolated and identified. These two compounds showed weak fungicidal activity against Colletotrichum fragariae, an agriculturally important fungus. The X-ray crystal structure determination is reported for the first time for the new compound.
Technical Abstract: Bioassay guided fractionation of the ethyl acetate extract of Amyris elemifera was carried out to identify phytotoxic and antifungal constituents. A novel phytotoxic furanocoumarin 8-(3-methylbut-2-enyloxy)-marmesin acetate (1) and its deacyl analog 8-(3-methylbut-2-enyloxy)-marmesin (2) were isolated. Both these compounds inhibited growth of the dicot Lactuca sativa (lettuce) and the monocot Agrostis stolonifera with more pronounced inhibitory effect on the monocots at 330 µM by 1. In Lemna paucicostata Hegelm phytotoxicity bioassay the IC50 value for 1 was 26 µM, whereas 2 had an IC50 value of 102 µM. Compounds 1 and 2 were weakly antifungal against Colletotrichum fragariae Brooks in TLC bioautography. The X-ray crystal structure determination is reported for the first time for 1. Both compounds have the S configuration at C-2 based on [a]D values and X-ray crystallographic data.