Phytotoxic lignans of Leucophyllum frutescens

Bioassay-guided fractionation of the hexane:ethyl acetate (1:1) extract of the leaves of Leucophyllum frutescens (Berl.) I.M.Johnst (Scrophulariaceae) led to the isolation of its phytotoxic constituents diayangambin (1), epiyangambin (2), diasesartemin (3) and epiashantin (4). Phytotoxicity was demonstrated as inhibition of seed germination of Agrostis stolonifera cv. penncross (Poaceae) and inhibition of development of Lactuca sativa L. (Asteraceae) seedlings in a microassay using 24-well plates. Compound 1 was the most phytotoxic to L. sativa, showing strong inhibitory activity at 110 microM. Compound 1 was more active than 2 and 3 in inhibiting the growth of A. stolonifera with I(50) values of 160, 670 and 930 microM, respectively. At a concentration of 500 microM, these compounds inhibited all phases of onion root cell division. This is the first demonstration of antimitotic activity of these furofuran lignans, and the first report of their isolation from this species.