Phytotoxic and antifungal compounds from two apiaceae species, Lomatium californicum and Ligusticum hultenii, rich sources of Z-ligustilide and apiol, respectively.

The seeds of two Apiaceae species, Ligusticum hultenii and L.gmatium californicum, were investigated. Preliminary bioassays indicated that methylene chloride extracts of seeds of both species contained selective phytotoxic activity against monocots and antifungal activity against Colletotrichum fragariae. Active constituents were isolated by bioassay-guided fractionation and the structures were elucidated by NMR and GC-MS as apiol and Z-ligustilide, isolated from L. hultenii and L. californicum, respectively. Apiol and Z-ligustilide had I50 values of about 80 and 600 μ M, respectively, for inhibition of the growth of Lemna paucicostata. The methylene chloride (CH₂CI₂) extracts of the seeds and the isolated and purified compounds were tested against the 2-methylisobomeol-producing cyanobacterium (blue-green alga) Oscillatoria perornata and the green alga Selenastrum capricornutum. The CH₂CI₂ extracts of both Apiaceae species and apiol were weakly toxic to both species of phytoplankton, while Z-ligustilide was toxic to both with complete inhibitory concentration (LCIC) of 53 μM. Seeds of L. californicum and L. hultenii were found to be rich sources of Z-ligustilide (97mg/g of dry seed) and apiol (40 mg/g of dry seed), respectively.