Abstract
The oleoresin of the ponderosa pine,Pinus ponderosa (Pinaceae) exhibited broad antimicrobial activity. In order to identify the active compounds, the oleoresin was steam distilled to give a distillate and residue. The distillate contained mainly monoterpenes and some sesquiterpenes, while the residue consisted chiefly of four structurally related diterpene acids. An antimicrobial assay with the pure compounds indicated that the monoterpenes were active primarily against fungi, but there was also some activity against gram-positive bacteria. The diterpene acids, in contrast, only exhibited activity against gram-positive bacteria. Although not all of the identified sesquiterpenes could be tested, longifolene showed activity only against gram-positive bacteria. Therefore, it appears that the oleoresin ofP. ponderosa functions as a biochemical defense against microbial invasion.
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References
Anderson, A.B., Riffer, R., andWong, A. 1969. Monoterpenes, fatty and resin acids ofPinus ponderosa andPinus jeffreyi.Phytochemistry 8:873–875.
Andrews, R.E., Park, L.W., andSpence, K.D. 1980. Some effects of Douglas fir terpenes on certain microorganisms.Appl. Environ. Microbiol. 40:301–304.
Berryman, A.A. 1972. Resistance of conifers to invasion by bark beetle-fungus associations.BioScience 22:598–602.
Cobb, F.W., {jrJr.},Kristic, M., Zavarin, E., andBarber, H.W. 1968. Inhibitory effects of volatile oleoresin components onFomes annosus and fourCeratocystis species.Phytopathology 58:1327–1335.
Cook, S.P., andHain, F.P. 1985. Qualitative examination of the hypersensitive response of loblolly pine,Pinus taeda L. inoculated with two fungal associates of the southern pine beetle,Dendroctonus frontalis Zimmermann (Coleoptera: Scolytidae).Environ. Entomol. 14:396–400.
Fujii, R., andZinkel, D.F. 1984. Minor components of ponderosa pine oleoresin.Phytochemistry 23:875–878 and references therein.
Harris, G.C. 1948. Resin acids. V. The composition of the gum oleoresin acids ofPinus palustris.J. Am. Chem. Soc. 70:3671–3674 and reference therein.
Kubik, Y.M., andJackson, L.L. 1981. Embryo resorptions in mice induced by diterpene resin acids ofPinus ponderosa needles.Cornell Vet. 71:34–42 and reference therein.
Kubo, I., andNakatsu, T. 1990. Recent examples of preparative-scale recycling high performance liquid chromatography in natural products chemistry.LC-GC 8:933–939.
Miller, D.R., Madden, J.L., andBorden, J.H. 1986. Primary attraction ofIps latidens (LeConte) andHylastes gracilis LeConte (Coleoptera: Scolytidae) to high-girdled lodgepole pine,Pinus contorta var.latifolia Engelmann.Can. Entomol. 118:85–88.
Morris, O.N. 1972. Inhibitory effects of foliage extracts of some forest trees on commercialBacillus thuringiensis.Can. Entomol. 104:1357–1361.
Owen, D.R., Lindahl, K.Q., {jrJr.},Wood, D.L., andParmeter, J.R., {jrJr.}, 1987. Pathogenicity of fungi isolated fromDendroctonus valens, D. brevicomis, andD. ponderosae to ponderosa pine seedlings.Phytopathology 77:631–636.
Pain, T.D., andStephen, F.M. 1987. Response of loblolly pine to different inoculum doses ofCeratocystis minor, a blue-stain fungus associated withDendroctonus frontalis.Can. J. Bot. 65:2093–2095.
Parmeter, J.R., {jrJr.},Slaughter, G.W., Chen, M.-M., Wood, D.L., andStubbs, H.A. 1989. Single and mixed inoculations of ponderosa pine with fungal associates ofDendroctonus spp.Phytopathology 79:768–772.
Phillips, T.W., Wilkening, A.J., Atkinson, T.H., Nation, J.L., Wilkinson, R.C., andFoltz, J.L. 1988. Synergism of turpentine and ethanol as attractants for certain pine-infesting beetles (Coleoptera).Environ. Entomol. 17:456–462.
Raffa, K.F., andBerryman, A.A. 1982. Accumulation of monoterpenes and associated volatiles following inoculation of grand fir with a fungus transmitted by the fir engraver,Scolytus ventralis (Coleoptera: Scolytidae).Can. Entomol. 114:797–810.
Raffa, K.F., andSmalley, E.B. 1988. Host resistance to invasion by lower stem and root infesting insects of pine: Response to controlled inoculations with the fungal associateLeptographium terebrans.Can. J. For. Res. 18:675–681.
Rose, A.F., Jones, K.C., Haddon, W.F., andDreyer, D.L. 1981. Grindelane diterpenoid acids fromGrindelia humilis: Feeding deterrency of diterpene acids towards aphids.Phytochemistry 20:2249–2253.
Schuh, B.A., andBenjamin, D.M. 1984. The chemical feeding ecology ofNeodipron dubiosus Schedl,N. rugifrons Midd., andN. lecontei (Fitch) on Jack pine (Pinus banksiana Lamb.).J. Chem. Ecol. 10:1071–1079.
Smirnoff, W.A. 1972. Effects of volatile substances released by foliage ofAbies balsamea.J. Invert. Pathol. 19:32–35.
Smith, R.H. 1964. Variation in the monoterpenesof Pinus ponderosa laws.Science 143:1337–1338.
Taniguchi, M., andSatomura, Y. 1972. Structure and physiological activity of carbostyril compounds.Agric. Biol. Chem. 36:2169–2175.
Vité, J.P. 1961. Influence of water supply on oleoresin exudation pressure and resistance to bark beetle attack inPinus ponderosa.Contrib. Boyce Thompson Inst. 21:37–66.
Wagner, M.R., Benjamin, D.M., Clancy, K.L., andSchuh, B.A. 1983. Influence of diterpene resin acids on feeding and growth of larch sawfly,Pristphora erichsonii (Hartig).J. Chem. Ecol. 9:119–127.
Wood, D.L. 1972. Selection and colonization of ponderosa pine by bark beetles, pp. 101–117,in H.F. van Emden (ed.). Insect/Plant Relationships. Blackwell Scientic, Oxford.
Wood, D.L. 1982. The role of pheromones, kairomones and allomones in the host selection and colonization behavior of bark beetles.Annu. Rev. Entomol. 27:411–446.
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Himejima, M., Hobson, K.R., Otsuka, T. et al. Antimicrobial terpenes from oleoresin of ponderosa pine treePinus ponderosa: A defense mechanism against microbial invasion. J Chem Ecol 18, 1809–1818 (1992). https://doi.org/10.1007/BF02751105
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DOI: https://doi.org/10.1007/BF02751105