Abortifacient effects of a unique class of vasoactive lipids from Pinus ponderosa needles.

Abstract

Pinus ponderosa needle (PN) ingestion by late pregnant cows results in decreased uterine blood flow, premature parturition, and retained placentae. Further, plasma from PN-fed cows increases caruncular arterial tone (i.e., induces prolonged contraction) in an isolated perfused bovine placentome. A novel class of vasoactive lipids was isolated and identified using a bovine placentome assay-guided fractionation of CH2Cl2 extracts of PN. Placentome perfusion tests indicated that 1-12-dodecanedioyl-dimyristate (14-12-14) was the most potent of the PN lipids for increasing caruncular arterial tone. Late pregnant guinea pigs (GP) were used to evaluate the abortifacient activity of these vasoactive lipids. In Study 1, on d 50 of gestation, part of the control diet was replaced with chopped PN (Diet A) or chopped PN subjected to sequential extraction with diethyl ether (Et2O; Diet B); Et2O and CH2Cl2 (Diet C); and Et2O, CH2Cl2, and methanol (Diet D). The GP on Diets A and B exhibited shorter (P<.01) gestation lengths and reduced (P<.01) pig birth weights than GP on the control diet or Diets C and D. Further, only GP on Diets A and B exhibited retained placentae. In Study 2, on d 50 of gestation, part of the control diet was replaced with chopped PN that had been subjected to exhaustive CH2Cl2 extraction and then infiltrated with either CH2Cl2 alone (Diet E), CH2Cl2 containing 14-12-14 (Diet F), or CH2Cl2 containing isocupressic acid (Diet G); then solvents were evaporated. The GP consuming Diet F had shorter (P<.05) gestation lengths and reduced (P<.05) pig birth weights than did GP consuming Diets E or G. The GP consuming Diet F also exhibited a high incidence of retained placentae. These data provide evidence that a unique class of vasoactive lipids in PN exhibit abortifacient activity in guinea pigs.

Case-control study of late-term abortions associated with mare reproductive loss syndrome in central Kentucky

“…A number of plants (including grasses) have been associated with abortion in cattle and sheep. [4][5][6][7][8][9][10][11] Few reports, however, describe plants that are fetotoxic in horses. Sudan grass and sorghum are considered toxic to equine fetuses.…”

Total Synthesis of (+)-Strongylophorines 2 and 9

“…Hence, an efficient and diversity-oriented total synthesis to access the tangled and congested polycyclic frameworks of 2 and other congeners is highly desired to provide a perfect platform for examination of their biological potential. The combination of structure complexity and biological potency led Poulsen and co-workers in 2016 to report an elegant semisynthesis of the strongylophorine family by starting from the labdane diterpene isocupressic acid, a rather infrequent and commercially unavailable natural product. They were able to access the initial bicyclic skeleton from isocupressic acid which, in turn , was extracted from the bark of the ponderosa pine tree (∼3 g from 500 g of bark) in gram scale .…”