Piperidine alkaloids in North American Pinus taxa: implications for chemosystematics

Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight ( P. cembroides, P. durangensis, P. engelmannii, P. leiophylla, P. leiophylla var. chihuahuana, P. lumholtzii, P. monophylla, and P. ponderosa) contained alkaloi...

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Published inBiochemical systematics and ecology Vol. 32; no. 1; pp. 63 - 74
Main Authors Gerson, Elizabeth A, Kelsey, Rick G
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2004
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Abstract Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight ( P. cembroides, P. durangensis, P. engelmannii, P. leiophylla, P. leiophylla var. chihuahuana, P. lumholtzii, P. monophylla, and P. ponderosa) contained alkaloids; only a trace was detected in P. ponderosa var. arizonica; and no alkaloids were found in P. discolor. Relative concentrations of the two end products of piperidine synthesis were consistent among taxa within subsections: the Leiophyllae produced euphococcinine exclusively; the Ponderosae produced primarily pinidine; and the Cembroides produced appreciable quantities of both. Alkaloid profiles of P. leiophylla and P. l. chihuahuana were very similar, and in agreement with classification of chihuahuana as a variety of P. leiophylla. Among the Ponderosae, P. p. arizonica was unique in its lack of alkaloids, suggesting species-level distinction from P. ponderosa may be appropriate. The absence of alkaloids in P. discolor, contrary to its close relative P. cembroides, provides further evidence towards designation as a separate species. Alkaloids in a subset of seedlings subjected to water stress did not differ from controls.
AbstractList Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight ( P. cembroides, P. durangensis, P. engelmannii, P. leiophylla, P. leiophylla var. chihuahuana, P. lumholtzii, P. monophylla, and P. ponderosa) contained alkaloids; only a trace was detected in P. ponderosa var. arizonica; and no alkaloids were found in P. discolor. Relative concentrations of the two end products of piperidine synthesis were consistent among taxa within subsections: the Leiophyllae produced euphococcinine exclusively; the Ponderosae produced primarily pinidine; and the Cembroides produced appreciable quantities of both. Alkaloid profiles of P. leiophylla and P. l. chihuahuana were very similar, and in agreement with classification of chihuahuana as a variety of P. leiophylla. Among the Ponderosae, P. p. arizonica was unique in its lack of alkaloids, suggesting species-level distinction from P. ponderosa may be appropriate. The absence of alkaloids in P. discolor, contrary to its close relative P. cembroides, provides further evidence towards designation as a separate species. Alkaloids in a subset of seedlings subjected to water stress did not differ from controls.
Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight (P. cembroides, P. durangensis, P. engelmannii, P. leiophylla, P. leiophylla var. chihuahuana, P. lumholtzii, P. monophylla, and P. ponderosa) contained alkaloids; only a trace was detected in P. ponderosa var. arizonica; and no alkaloids were found in P. discolor. Relative concentrations of the two end products of piperidine synthesis were consistent among taxa within subsections: the Leiophyllae produced euphococcinine exclusively; the Ponderosae produced primarily pinidine; and the Cembroides produced appreciable quantities of both. Alkaloid profiles of P. leiophylla and P. l. chihuahuana were very similar, and in agreement with classification of chihuahuana as a variety of P. leiophylla. Among the Ponderosae, P. p. arizonica was unique in its lack of alkaloids, suggesting species-level distinction from P. ponderosa may be appropriate. The absence of alkaloids in P. discolor, contrary to its close relative P. cembroides, provides further evidence towards designation as a separate species. Alkaloids in a subset of seedlings subjected to water stress did not differ from controls.
Author Kelsey, Rick G
Gerson, Elizabeth A
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Keywords Chemotaxonomy
Biosynthesis
Water stress
2,6-Disubstituted piperidine alkaloids
Pinaceae systematics
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  article-title: Variation of piperidine alkaloids in ponderosa (Pinus ponderosa) and lodgepole pine (P. contorta) foliage from central Oregon
  publication-title: J. Chem. Ecol.
  doi: 10.1023/A:1022369416745
  contributor:
    fullname: Gerson
– start-page: 137
  year: 1998
  ident: 10.1016/S0305-1978(03)00174-1_BIB11
  article-title: The history of pines in Mexico and Central America
  contributor:
    fullname: Perry
– ident: 10.1016/S0305-1978(03)00174-1_BIB1
– ident: 10.1016/S0305-1978(03)00174-1_BIB2
– volume: 25
  start-page: 2027
  year: 1999
  ident: 10.1016/S0305-1978(03)00174-1_BIB4
  article-title: Piperidine alkaloids in nitrogen fertilized ponderosa pine
  publication-title: J. Chem. Ecol.
  doi: 10.1023/A:1021080605332
  contributor:
    fullname: Gerson
– volume: 20
  start-page: 561
  year: 1967
  ident: 10.1016/S0305-1978(03)00174-1_BIB6
  article-title: (+)-9-aza-1-Methylbicyclo [3,3,1]nonan-3-one, a new alkaloid from Euphorbia atoto Forst
  publication-title: Aust. J. Chem.
  doi: 10.1071/CH9670561
  contributor:
    fullname: Hart
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Snippet Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight ( P. cembroides, P....
Foliage samples from 10 taxa of the genus Pinus occurring in Mexico and the southwestern US were extracted for piperidine alkaloids. Eight (P. cembroides, P....
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StartPage 63
SubjectTerms 2,6-Disubstituted piperidine alkaloids
Biosynthesis
chemical composition
chemical constituents of plants
Chemotaxonomy
Pinaceae systematics
Water stress
Title Piperidine alkaloids in North American Pinus taxa: implications for chemosystematics
URI https://dx.doi.org/10.1016/S0305-1978(03)00174-1
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