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Title: PHYTOTOXIC AND ANTIFUNGAL COMPOUNDS FROM TWO APIACEAE SPECIES, LOMATIUM CALIFORNICUM AND LIGUSTICUM HULTENII, RICH SOURCES OF Z-LIGUSTILIDE AND APIOL, RESPECTIVELY.

Author
item Meepagala, Kumudini
item STURTZ, GEORGE - AROMAGEN - ALBANY, OREGON
item Wedge, David
item Schrader, Kevin
item Duke, Stephen

Submitted to: Journal of Chemical Ecology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/13/2005
Publication Date: 7/7/2005
Citation: Meepagala, K.M., Sturtz, G., Wedge, D.E., Schrader, K., Duke, S.O. 2005. Phytotoxic and antifungal compounds from two apiaceae species, lomatium californicum and ligusticum hultenii, rich sources of z-ligustilide and apiol, respectively.. Journal of Chemical Ecology. 31:1567-1578.

Interpretive Summary: As part of a search for pesticides of natural origin, seeds of two Apiaceae species, Ligusticum hultenii and Lomatium californicum were investigated. Preliminary bioassays indicated the presence of selective herbicide activity against monocots and antifungal activity against Colletotrichum species in the methylene chloride extracts of seeds of both species. Active compounds were isolated and identified as apiol and Z-ligustilide isolated from L. hultenii and L. californicum, respectively. The methylene chloride extracts of the seeds and the isolated and purified compounds were tested against methyl isoborneol (MIB) producing blue-green alga Oscillatoria peronata, and the green alga Selenastrum capricornutum. The methylene chloride extracts of both species, and apiol, were weakly toxic to both algae. Z-ligustilide inhibited both algae equally, with a lowest complete inhibition concentration of 53µM. L. californicum seeds and L. hultenii seeds were found to be rich sources of Z-ligustilide, with 97 mg/g of dry seed, and apiol with 40 mg/g of dry seed, respectively. Z-ligustilide is considered to be the active and marker compound in the herbal drug Angelica sinensis, also known as Dong quai or "Female Ginseng".

Technical Abstract: As part of a search for pesticides of natural origin, seeds of two Apiaceae species, Ligusticum hultenii and Lomatium californicum were investigated. Preliminary bioassays indicated the presence of selective phytotoxic activity against monocots and antifungal activity against Colletotrichum species in the methylene chloride extracts of seeds of both species. 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. The CH2Cl2 extracts of the seeds and the isolated and purified compounds were tested against methyl isoborneol (MIB) producing blue-green alga Oscillatoria peronata, and the green alga Selenastrum capricornutum. The CH2Cl2 extracts of both species, and apiol, were weakly toxic to both algae. Z-ligustilide inhibited both algae equally, with a lowest complete inhibition concentration of 53 uM. L. californicum seeds and L. hultenii seeds were found to be rich sources of Z-ligustilide, with 97 mg/g of dry seed, and apiol with 40 mg/g of dry seed, respectively. Z-ligustilide is considered to be the active and marker compound in the herbal drug Angelica sinensis, also known as Dong quai or "Female Ginseng".