Piperidine alkaloids in North American Pinus taxa: Implications for chemosystematics

Biochemical Systematics and Ecology

Volumn 32, Issue 1, 2004, Pages 63-74

  Gerson, Elizabeth A ^a   Kelsey, Rick G ^a  

^a USDA FOREST SERVICE   (United States)

Author keywords

2,6 Disubstituted piperidine alkaloids; Biosynthesis; Chemotaxonomy; Pinaceae systematics; Water stress

Indexed keywords

ALKALOID; BIOCHEMICAL COMPOSITION; TAXONOMY; WATER STRESS;

MONOPHYLLA; PINACEAE; PINUS; PINUS ARIZONICA; PINUS CEMBROIDES; PINUS DISCOLOR; PINUS DURANGENSIS; PINUS ENGELMANNII; PINUS LEIOPHYLLA; PINUS LUMHOITZII; PINUS MONOPHYLLA; PINUS PONDEROSA;

EID: 0345874660     PISSN: 03051978     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0305-1978(03)00174-1     Document Type: Article

References (22)

1. Almaráz-Abarca, N., 2000. Estudio quimiotaxonomico de Pinus seccion Leiophyllae (Pinaceae). PhD Dissertation, Instituto Politecnico Nacional, Escuela Nacional de Ciencias Biologicas, Mexico.
2. Cornejo-Oviedo, E.H., 1999. Regeneration aspects of three Mexican Pinus species: field and greenhouse studies. PhD dissertation, Oregon State University, Corvallis.
3. Gerson, E.A., 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.
4. Gerson, E.A., Kelsey, R.G., 1999a. Piperidine alkaloids in nitrogen fertilized ponderosa pine. J. Chem. Ecol. 25, 2027-2039.
5. Gerson, E.A., Kelsey, R.G., 1999b. Foliar storage and extraction methods for quantitative analysis of piperidine alkaloids from ponderosa pine (Pinus ponderosa). Phytochem. Anal. 10, 322-327.
6. Hart, N.K., Johns, S.R., 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.
7. Hoft, M., Verpoorte, R., 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.
8. Karamangala, R.R., Nickrent, D.L., 1989. An electrophoretic study of representatives of subgenus Diploxylon of Pinus. Can. J. Bot. 67, 1750-1759.
9. Krejsa, B.B., Rouquette, Jr. F.M., Holt, E.G., Camp, B.J., Nelson, L.R., 1987. Alkaloid and nitrate concentrations in pearl millet as influenced by drought stress and fertilization with nitrogen. Agron. J. 79, 266-270.
10. Liston, A., Robinson, W.A., Piñero, D., Alvarez-Buylla, E.R., 1999. Phylogenetics of Pinus (Pinaceae) based on nuclear ribosomal DNA internal transcribed spacer region sequences. Mol. Phylogenet. Evol. 11, 95-109.
11. Perry, Jr. J.P., Graham, A., Richardson, D.M., 1998. The history of pines in Mexico and Central America. In: Richardson, D.M. (Ed.), Ecology and Biogeography of Pinus. Cambridge University Press, New York, pp. 137-149.
12. Perry, J.P., 1991. The Pines of Mexico and Central America. Timber Press, Portland, OR.
13. Price, R.A., Liston, A., Strauss, S.H., 1998. Phylogeny and systematics of Pinus. In: Richardson, D.M. (Ed.), Ecology and Biogeography of Pinus. Cambridge University Press, New York, pp. 49-68.
14. Rehfeldt, G.E., 1993. Genetic variation in the Ponderosae of the Southwest. Am. J. Bot. 80, 330-343.
15. Rehfeldt, G.E., 1999. Systematics and genetic structure of Ponderosae taxa (Pinaceae) inhabiting the mountain islands of the Southwest. Am. J. Bot. 86, 741-752.
16. Robinson, T., 1979. The evolutionary ecology of alkaloids. In: Rosenthal, G.A., Janzen, D.H. (Eds.), Herbivores: Their Interaction with Secondary Plant Metabolites. Academic Press, New York, pp. 413-448.
17. Stermitz, F.R., Tawara, J.N., Bocckl, M., Poneras, M., Foderaro, T.A., Todd, F.G., 1994. Piperidine alkaloid content of Picea (spruce) and Pinus (pine). Phytochemistry 35, 951-953.
18. Tallent, W.H., Stromberg, V.L., Horning, E.C., 1955. Pinus alkaloids. The alkaloids of P. sabiana Dougl. and related species. J. Am. Chem. Soc. 77, 6361-6364.
19. Tawara, J.N., Blokhin, A., Foderaro, T.A., Stermitz, F.R., 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.
20. Tawara, J.N., Stermitz, F.R., Blokhin, A.V., 1995. Alkaloids of young ponderosa pine seedlings and late steps in the biosynthesis of pinidine. Phytochemistry 39, 705-708.
21. Tawara, J.N., 1994. Chemical analyses of Picea and Pinus (Pinaceae) and biosynthetic studies on Pinus ponderosa alkaloids. PhD Dissertation, Colorado State University, Ft. Collins.
22. Waterman, P.G., 1998. Alkaloid chemosystematics. In: Cordell, G.A. (Ed.), The Alkaloids: Chemistry and Pharmacology, vol. 50. Academic Press, San Diego, pp. 537-565.