Phytotoxic Eremophilanes from Ligularia macrophylla.
Systematic bioassay-guided fractionation of the methylene chloride extract of the roots from Ligularia macrophylla was performed to identify both phytotoxic and antifungal compounds. Four phytotoxic eremophilanes (furanoeremophilan-14beta,6alpha-olide, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane, eremophil-7(11)-ene-12,8alpha;14beta,6alpha-diolide, and 3alpha-angeloyloxybakkenolide A) and two antifungal fatty acids (linoleic acid and alpha-linolenic acid) were isolated. The X-ray crystal structure determination of 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane is reported here for the first time. All four eremophilanes substantially inhibited growth of the monocot Agrostis stolonifera (bentgrass) while demonstrating little activity against the dicot Lactuca sativa (lettuce) at 1000 microM. In a dose-response screening of all compounds for growth inhibitory activity against Lemna paucicostata, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane was the most active with an IC50 of 2.94+/-0.16 microM. This compound also caused the greatest reduction of photosynthetic electron flow; however, its mode of action remains to be determined. Evaluation of isolated compounds for activity against the Formosan subterranean termite, Coptotermes formosanus, is also reported. At a concentration of 0.5% (wt/wt), 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane significantly reduced the consumption of filter paper by C. formosanus.
Cantrell
Charles L
CL
USDA-ARS, Natural Products Utilization Research Unit, University, MS 38677, USA. clcantr1@olemiss.edu
Duke
Stephen O
SO
Fronczek
Frank R
FR
Osbrink
Weste L A
WL
Mamonov
Leonid K
LK
Vassilyev
Juriy I
JI
Wedge
David E
DE
Dayan
Franck E
FE
D031703:Agrostis / Q000187:drug effects; D000818:Animals; D019659:Asteraceae / Q000737:chemistry*; D020231:Colletotrichum / Q000187:drug effects; D018360:Crystallography, X-Ray; D005227:Fatty Acids / Q000032:analysis / Q000494:pharmacology; D005659:Fungicides, Industrial / Q000032:analysis; D006540:Herbicides / Q000032:analysis*; D007306:Insecticides; D020049:Isoptera; D018545:Lactuca / Q000187:drug effects; D009281:Naphthalenes / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes
D005227:Fatty Acids; D005659:Fungicides, Industrial; D006540:Herbicides; D007306:Insecticides; D009281:Naphthalenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C018286:eremophilane compounds