Use of Circular Dichroism to Determine the Absolute Configuration of a Pimarane Diterpenoid from the Southern African Sclerocroton integerrimus (Euphorbiaceae)
Free accessResearch articleFirst published online August, 2014
Use of Circular Dichroism to Determine the Absolute Configuration of a Pimarane Diterpenoid from the Southern African Sclerocroton integerrimus (Euphorbiaceae)
From the stem bark and leaves of Sclerocroton integerrimus, eight compounds, including 17-hydroxy-ent-pimara-8(14),15-dien-3-one (1), were isolated. The structures of the compounds were determined on the basis of spectroscopic analysis. The absolute configuration of 17-hydroxy-ent-pimara-8(14),15-dien-3-one was confirmed from electronic circular dichroism studies.
BohlmannF., JakupovicJ., SchusterA., KingR.M., RobinsonH. (1982) New melampolides, kaurene derivatives and other constituents from Ichthyothere species. Phytochemistry, 21, 2317–2327.
7.
AsiliJ., LambertM., ZieglerH.L., StaerkD., SairafianpourM., WittM., AsghariG., IbrahimiI.S., JaroszewskiJ.W. (2004) Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells. Journal of Natural Products, 67, 631–637.
8.
XuR., YeY., ZhaoW. (2012) Introduction to Natural Products Chemistry.Taylor & Francis Group, LLC Beijing.
9.
RalduginV.A., ShakirovM.M., LeibyukT.V., ShevtsovS.A. (1992) Triterpenoids from Abies species. Chemistry of Natural Compounds, 27, 444–449.
10.
YanR.Y., TanY.X., CuiX.Q., ChenR.Y., YuD.Q. (2008) Diterpenoids from the roots of Suregada glomerulata. Journal of Natural Products, 71, 195–198.
11.
DjerassiC., RecordsR., BunnenbergE., MislowK., MoscowitzA. (1962) Inherently dissymmetric chromophores. Optical rotator dispersion of α,β-unsaturated ketones and conformational analysis of cyclohexenones. Journal of the American Chemical Society, 84, 870–872.
12.
MiJ.F., XuR.S., YangY.P., YangP.M. (1993) Studies on circular dichroism of diterpenoids from Mallotus anomalus and sesquiterpenoid tussilagone. Acta Pharmaceutica Sinica, 28, 105–109.
13.
RobinsonD.L., TheobaldD.W. (1967) Conformational abnormalities in cyclohexane chemistry. Quarterly Review, Chemical Society, 21, 314–330.
14.
CarvalhoT.C., SimaoM.R., AmbrosioS.R., Furtado NiegeA.J.C., VenezianiR.C.S., HelenoVcg, Da CostaF.B., GomesBpfa, SouzaM.G.M., Borges dos ReisE., MartinsC.H.G. (2011) Antimicrobial activity of diterpenes from Viguiera arenaria against endodontic bacteria. Molecules, 16, 543–551.
15.
PortoT.S., RangelR., FurtadoNajc, de CarvalhoT.C., MartinsC.H.G., VenezianiR.C.S., da CostaF.B., VinholisA.H.C., CunhaW.R., HelenoV.C.G., AmbrosioS.R. (2009) Pimarane-type diterpenes: antimicrobial activity against oral pathogens. Molecules, 14, 191–199.
16.
SeverianoM.E., SimaoM.R., PortoT.S., MartinsC.H.G., VenezianiR.C.S., FurtadoNajc, ArakawaN.S., SaidS., de OliveiraDiCR, CunhaW.R., GregorioL.E., AmbrosioS.R. (2010) Anticariogenic properties of ent-pimarane diterpenes obtained by microbial transformation. Molecules, 15, 8553–8566
CarpenterR.C., SotheeswaranS., SultanbawaM.U.S., TernaiB. (1980) 13C NMR studies of some lupane and taraxerane triterpenes. Organic Magnetic Resonance, 14, 462–465.
