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Piperidine Alkaloids in Nitrogen Fertilized Pinus ponderosa

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Abstract

We fertilized individual, pole-size ponderosa pine trees at two low-quality sites and pine saplings at a relatively high-quality site, with ammonium nitrate. Six to 12 months later, we measured total %N and 2,6-disubstituted piperidine alkaloids in the foliage. The N additions raised foliar %N above deficiency levels (i.e., from 1.0–1.1% to 1.4–1.6%) at the low-quality sites, but did not elevate foliar %N in saplings at the higher quality site, where it was already (1.9%) well above critical levels. In control trees with foliar N below a threshold of 1.1%, we detected no more than trace levels of alkaloids, indicating that alkaloid production is highly constrained by N deficiency. The N additions increased mean concentrations of the predominant alkaloid, pinidine, at all three sites. Mean total alkaloid concentrations for fertilized trees at the two low-quality sites were 12 and 155 μg/g dry wt higher than controls (relative increases of 12× and 4.5×, respectively). For saplings at the high-quality site, the mean total increased by 584 μg/g dry wt (1.6×) with the N additions. Allocation of foliar N to alkaloids was highest in fertilized saplings (0.81%) compared to control saplings (0.53%). These findings demonstrate that foliar alkaloid concentrations can be increased by nitrogen fertilization of forest trees growing on both low- and high-quality sites. Fertilizing for the purpose of inhibiting potential herbivores may be more successful at higher quality sites where alkaloid levels are enhanced relative to food quality (foliar %N).

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REFERENCES

  • Baldwin, I. T., and Ohnmeiss, T. E. 1994. Coordination of photosynthetic and alkaloidal responses to damage in uninducible and inducible Nicotiana sylvestris. Ecology 75:1003-1014.

    Google Scholar 

  • Bjorkman, C., Larsson, S., and Gref, R. 1991. Effects of nitrogen fertilization on pine needle chemistry and sawfly performance. Oecologia 86:202-209.

    Google Scholar 

  • Cochran, P. H. 1973. Response of individual ponderosa pine trees to fertilization. USDA Forest Service, Research Note PNW-206, 15 pp.

  • Cochran, P. H. 1978. Response of a pole-size ponderosa pine stand to nitrogen, phosphorus, and sulfur. USDA Forest Service, Research Note PNW-319, 8 pp.

  • Furniss, R. L., and Carolin, V. M. 1977. Western Forest Insects. USDA Forest Service, Miscellaneous Publication No. 1339.

  • Gerson, E. A., and Kelsey, R. G. 1998. Variation of piperidine alkaloids in ponderosa (Pinus ponderosa) and lodgepole pine (P. contorta) foliage from central Oregon. J. Chem. Ecol. 24:815-827.

    Google Scholar 

  • Gerson, E. A., and Kelsey, R. G. 1999. Foliar storage and extraction methods for quantitative analysis of piperidine alkaloids from ponderosa pine (Pinus ponderosa). Phytochem. Anal. 10:1-6.

    Google Scholar 

  • Gleason, J. F., Duryea, M., Rose, R., and Atkinson, M. 1990. Nursery and field fertilization of 2 + 0 ponderosa pine seedlings: The effect on morphology, physiology, and field performance. Can. J. For. Res. 20:1766-1772.

    Google Scholar 

  • Hart, N. K., Johns, S. R., and Lamberton, J. A. 1967. (+)-9-Aza-1-methylbicyclo[3,3,1]nonan-3-one, a new alkaloid from Euphorbia atoto Forst. Aust. J. Chem. 20:561-563.

    Google Scholar 

  • Hoft, M., Verpoorte, R., and Beck, E. 1996. Growth and alkaloid contents in leaves of Tabernaemontana pachysiphon Stapf (Apocynaceae) as influenced by light intensity, water and nutrient supply. Oecologia 107:160-169.

    Google Scholar 

  • Hoft, M., Verpoorte R., and Beck, E. 1998. Leaf alkaloid contents of Tabernaemontana pachysiphon as influenced by endogenous and environmental factors in the natural habitat. Planta Med. 64:148-152.

    Google Scholar 

  • Johnson, N. D., Liu, B., and Bentley, B. L. 1987. The effects of nitrogen fixation, soil nitrate, and defoliation on the growth, alkaloids, and nitrogen levels of Lupinus succulentus (Fabaceae). Oecologia 74:425-431.

    Google Scholar 

  • Johnson, N. D., Rigney, L. P., and Bentley, B. L. 1989. Short-term induction of alkaloid production in lupines: differences between N2-fixing and nitrogen-limited plants. J. Chem. Ecol. 15:2425-2434.

    Google Scholar 

  • Kamm, C. D., Tawara, J. N., and Stermitz, F. R. 1998. Spruce budworm larval processing of piperidine alkaloids from spruce needles. J. Chem. Ecol. 24:1153-1160.

    Google Scholar 

  • Kozlowski, T. T., and Pallardy, S. G. 1997. Physiology of Woody Plants. Academic Press, San Diego.

    Google Scholar 

  • Krejsa, B. B., Rouquette, Jr., F. M., Holt, E. C., Camp, B. J., and Nelson, L. R. 1987. Alkaloid and nitrate concentrations in pearl millet as influenced by drought stress and fertilization with nitrogen and sulfer. Agron. J. 79:266-270.

    Google Scholar 

  • Leete, E., and Juneau, K. N. 1969. Biosynthesis of pinidine. J. Am. Chem. Soc. 91:5614-5618.

    Google Scholar 

  • Leete, E., Lechleiter, J. C., and Carver, R. A. 1975. Determination of the “starter” acetate unit in the biosynthesis of pinidine. Tetrahedron Lett. 44:3779-3782.

    Google Scholar 

  • Mason, R. R., Wickman, B. E., Beckwith, R. C., and Paul, H. G. 1992. Thinning and nitrogen fertilization in a grand fir stand infested with western spruce budworm. Part I: Insect response. For. Sci. 38:235-251.

    Google Scholar 

  • McClure, M. S. 1991. Nitrogen fertilization of hemlock increases susceptibility to hemlock woolly adelgid. J. Arbor. 17:227-229.

    Google Scholar 

  • McCullough, D. G., and Kulman, H. M. 1991. Effects of nitrogen fertilization on young jack pine budworm (Pinus banksiana) and on its suitability as a host for jack pine budworm (Choristoneura pinus pinus) (Lepidoptera: Tortricidae). Can. J. For. Res. 21:1447-1458.

    Google Scholar 

  • McMillin, J. D., and Wagner, M. R. 1989. Assessing the impacts of foliage-feeding insects on timber and scenic beauty of ponderosa pine: a methodological approach, pp. 51-59, in A. Tecle, W. W. Covington, and R. H. Hamre (eds.). Multiresource Management of Ponderosa Pine Forests. USDA Forest Service, General Technical Report RM-185.

  • Oliver, W. W., and Ryker, R. A. 1990. Pinus ponderosa Dougl. ex Laws., pp. 413-424, in R. M. Burns and B. H. Honkala (eds.). Silvics of North America, Vol. 1: Conifers. USDA Forest Service, Agriculture Handbook 654.

  • Powers, R. F., Webster, S. R., and Cochran, P. H. 1988. Estimating the response of ponderosa pine forests to fertilization, pp. 219-225, in W. C. Schmidt (ed.). Future Forests of the Mountain West. USDA Forest Service, General Technical Report INT-243.

  • Ralphs, M. H., Manners, G. D., and Gardner, D. R. 1998. Influence of light and photosynthesis on alkaloid concentration in larkspur. J. Chem. Ecol. 24:167-182.

    Google Scholar 

  • SAS Institute, Inc. 1989. SAS/STAT User's Guide, Ver. 6, 4th ed., Vol. 2. Cary, North Carolina.

  • Schneider, M. J., Montali, J. A., Hazen, D., and Stanton, C. E. 1991. Alkaloids of Picea. J. Nat. Prod. 54:905-909.

    Google Scholar 

  • Smirnoff, W. A., and Bernier, B. 1973. Increased mortality of the Swaine jack-pine sawfly, and foliar nitrogen concentrations after urea fertilization. Can. J. For. Res. 3:112-121.

    Google Scholar 

  • Stermitz, F. R., Tawara, J. N., Boeckl, M., Pomeroy, M., Foderaro, T. A., and Todd, F. G. 1994. Piperidine alkaloid content of Picea (spruce) and Pinus (pine). Phytochemistry 5:951-953.

    Google Scholar 

  • Tallent, W. H., Stromberg, V. L., and Horning, E. C. 1955. Pinus alkaloids. The alkaloids of P. sabiana Dougl. and related species. J. Am. Chem. Soc. 77:6361-6364.

    Google Scholar 

  • Tawara, J. N. 1994. Chemical analyses of Picea and Pinus (Pinaceae) & biosynthetic studies on Pinus ponderosa alkaloids. PhD dissertation. Colorado State University, Fort Collins.

    Google Scholar 

  • Tawara, J. N., Blokhin, A., Foderaro, T. A., Stermitz, F. R., and Hope, H. 1993. Toxic piperidine alkaloids from pine (Pinus) and spruce (Picea) trees. New structures and a biosynthetic hypothesis. J. Org. Chem. 58:4813-4818.

    Google Scholar 

  • Tawara, J. N., Stermitz, F. R., and Blokhin, A. V. 1995. Alkaloids of young ponderosa pine seedlings and late steps in the biosynthesis of pinidine. Phytochemistry 39:705-708.

    Google Scholar 

  • Todd, F. G. 1994. Potentially toxic compounds of Convolvulacae and piperidine alkaloids of Picea. PhD dissertation. Colorado State University, Fort Collins.

    Google Scholar 

  • Todd, F. G., Stermitz, F. R., and Blohkin, A. V. 1995. Piperidine alkaloid content of Picea pungens (Colorado blue spruce). Phytochemistry 40:401-406.

    Google Scholar 

  • Wagner, M. R. 1988. Induced defenses in ponderosa pine against defoliating insects, pp. 141-155, in W. J. Mattson, J. Levieux and C. Bernard-Dagan (eds.). Mechanisms of Woody Plant Defenses Against Insects. Springer-Verlag, New York.

    Google Scholar 

  • Wickman, B. E., Mason, R. R., and Paul, H. G. 1996. Ponderosa pine response to nitrogen fertilization and defoliation by the pandora moth, Coloradia pandora Blake, pp. 118-126, in W. J. Mattson, P. Niemela and M. Rousi (eds.). Dynamics of Forest Herbivory: Quest for Pattern and Principle, USDA Forest Service, General Technical Report NC-183.

  • Will, G. M., and Youngberg, C. T. 1978. Sulfur status of some central Oregon soils. Soil Sci. Soc. Am. J. 42:132-134.

    Google Scholar 

  • Zabowski, D., and Henry, C. L. 1995. Soil and foliar nitrogen after fertiliser treatment of ponderosa pine. N.Z. J. For. Sci. 24:333-343.

    Google Scholar 

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Gerson, E.A., Kelsey, R.G. Piperidine Alkaloids in Nitrogen Fertilized Pinus ponderosa . J Chem Ecol 25, 2027–2039 (1999). https://doi.org/10.1023/A:1021080605332

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