Abstract
The seeds of two Apiaceae species, Ligusticum hultenii and Lomatium 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 μM, respectively, for inhibition of the growth of Lemna paucicostata. The methylene chloride (CH2Cl2) extracts of the seeds and the isolated and purified compounds were tested against the 2-methylisoborneol-producing cyanobacterium (blue-green alga) Oscillatoria perornata, and the green alga Selenastrum capricornutum. The CH2Cl2 extracts of both Apiaceae species and apiol were weakly toxic to both species of phytoplankton, while Z-ligustilide was toxic to both with a lowest complete inhibitory concentration (LCIC) of 53 μM. Seeds of L. californicum and L. hultenii were found to be rich sources of Z-ligustilide (97 mg/g of dry seed) and apiol (40 mg/g of dry seed), respectively.
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Acknowledgments
We thank Robert Johnson, Adriane Greer, Hope Harris, Marty Lanier, Linda Robertson, Dewayne Harries, and Ramona Pace for their valuable technical assistance. Don Stanford and Franck Wiggers are acknowledged for their assistance with GC-MS and NMR facilities.
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Meepagala, K.M., Sturtz, G., Wedge, D.E. et al. Phytotoxic and Antifungal Compounds from Two Apiaceae Species, Lomatium californicum and Ligusticum hultenii, Rich Sources of Z-ligustilide and Apiol, Respectively. J Chem Ecol 31, 1567–1578 (2005). https://doi.org/10.1007/s10886-005-5798-8
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DOI: https://doi.org/10.1007/s10886-005-5798-8