Open AccessFuranocoumarin with Phytotoxic Activity from the Leaves of Amyris elemifera (Rutaceae)
Author(s) -
Kumudini M. Meepagala,
Amy K. Bracken,
Frank R. Fronczek,
Robert D. Johnson,
David E. Wedge,
Stephen O. Duke
Publication year - 2020
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.0c04778
Subject(s) - furanocoumarin , lactuca , agrostis stolonifera , phytotoxicity , bioassay , botany , ethyl acetate , rutaceae , chemistry , biology , chromatography , poaceae , genetics
Bioassay-guided fractionation of the ethyl acetate extract of Amyris elemifera leaves 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. The X-ray crystal structure determination is reported for the first time for 1 . Both 1 and 2 have the S configuration at C-2' based on X-ray crystallographic data. Both these compounds inhibited the growth of the dicot Lactuca sativa (lettuce) and the monocot Agrostis stolonifera with a more pronounced inhibitory effect on the monocots at 330 μM by 1 . In Lemna paucicostata Hegelm phytotoxicity bioassay, the IC 50 value for 1 was 26 μM, whereas 2 had an IC 50 value of 102 μM. Compounds 1 and 2 were weakly antifungal against Colletotrichum fragariae Brooks in TLC bioautography.