General characteristics of Pinus spp. seed fatty acid compositions, and importance of Δ5-olefinic acids in the taxonomy and phylogeny of the genus

Lipids

Volumn 35, Issue 1, 2000, Pages 1-22

  Wolff, Robert L ^a   Pédrono, Frédérique ^a   Pasquier, Elodie ^a   Marpeau, Anne M ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; FATTY ACID DERIVATIVE; LINOLEIC ACID; OLEIC ACID; SATURATED FATTY ACID;

LIPID ANALYSIS; LIPID COMPOSITION; PHYLOGENY; PHYTOCHEMISTRY; PINE; REVIEW; TAXONOMY;

EMBRYOPHYTA; GYMNOSPERMAE; MONOPHYLLA; PINACEAE; PINUS; PINUS MERKUSII; PINUS MONOPHYLLA; PINUS PINASTER; PINUS SYLVESTRIS; STROBUS;

EID: 0033967201     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-000-0489-y     Document Type: Review

References (75)

1. Page, C.N. (1990) Gymnosperms: Coniferophytina (Conifers and Ginkgoids), in The Families and Genera of Vascular Plants (Kubitzki, K., ed.), Vol. 1, pp. 279-361, Pteridophytes and Gymnosperms (Kramer, K.U., and Green, P.S., eds.), Springer-Verlag, Berlin, Heidelberg.
2. Page, C.N. (1990) Gymnosperms: Coniferophytina (Conifers and Ginkgoids), in The Families and Genera of Vascular Plants (Kubitzki, K., ed.), Vol. 1, pp. 279-361, Pteridophytes and Gymnosperms (Kramer, K.U., and Green, P.S., eds.), Springer-Verlag, Berlin, Heidelberg.
3. Farjon, A. (1998) World Checklist and Bibliography of Conifers, The Royal Botanic Gardens, Kew, United Kingdom.
4. Rothwell, G.W. (1982) New Interpretations of the Earliest Conifers, Rev. Palaeobot. Palynol. 37, 7-29.
5. Miller, C.N., Jr. (1976) Early Evolution in the Pinaceae, Rev. Palaeobot. Palynol. 21, 101-117.
6. Wolff, R.L., Deluc, L.G., Marpeau, A.M., and Comps, B. (1997) Chemotaxonomic Differentiation of Conifer Families and Genera Based on the Seed Oil Fatty Acid Compositions: Multivariate Analyses, Trees 12, 57-65.
7. Wolff, R.L., Comps, B., Marpeau, A.M., and Deluc, L.G. (1997) Taxonomy of Pinus Species Based on the Seed Oil Fatty Acid Compositions, Trees 12, 113-118.
8. Wolff, R.L., Comps, B., Deluc, L.G., and Marpeau, A.M. (1997) Fatty Acids of the Seeds from Pine Species of the Ponderosa-Banksiana and Halepensis Sections. The Peculiar Taxonomic Position of Pinus pinaster, J. Am. Oil Chem. Soc. 74, 45-50.
9. Wolff, R.L. (1997) Discussion of the Term "Unusual" When Discussing Δ5-Olefinic Acids in Plant Lipids, J. Am. Oil Chem. Soc. 74, 619.
10. Wolff, R.L., Christie W.W., Pédrono, F., Marpeau, A.M., Tsevegsüren, N., Aitzetmüller, K., and Gunstone, F.D. (1999) Δ5-Olefinic Acids in the Seed Lipids from Four Ephedra Species and Their Distribution Between the α- and β-Positions of Triacylglycerols. Characteristics Common to Coniferophytes and Cycadophytes, Lipids 34, 855-864.
11. Wolff, R.L. (1999) The Phylogenetic Significance of Sciadonic (all-cis 5,11,14-20:3) Acid in Gymnosperms and Its Quantitative Significance in Land Plants, J. Am. Oil Chem. Soc. 76, 1515-1516.
12. Berdeaux, O., and Wolff, R.L. (1996) Gas-Liquid Chromatography-Mass Spectrometry of the 4,4-Dimethyloxazoline Derivatives of Δ5-Unsaturated Polymethylene-Interrupted Fatty Acids from Conifer Seed Oils, J. Am. Oil Chem. Soc. 73, 1323-1326.
13. Wolff, R.L., Christie, W.W., and Marpeau, A.M. (1999) Reinvestigation of the Polymethylene-Interrupted 18:2 and 20:2 Acids of Ginkgo biloba Seed Lipids, J. Am. Oil Chem. Soc. 76, 273-276.
14. Wolff, R.L., Pédrono, F., Marpeau, A.M., and Gunstone, F.D. (1999) The Seed Fatty Acid Composition and the Distribution of Δ5-Olefinic Acids in the Triacylglycerols of Some Taxares (Cephalotaxus and Podocarpus), J. Am. Oil Chem. Soc. 76, 469-473.
15. Wolff, R.L., Christie W.W., Pédrono, F., and Marpeau, A.M. (1999) Arachidonic, Eicosapentaenoic, and Biosynthetically Related Fatty Acids in the Seed Lipids from a Primitive Gymnosperm, Agathis robusta, Lipids 34, 1083-1097.
16. 13C-NMR Spectroscopy, Chem. Phys. Lipids 78, 89-96.
17. 13C Nuclear Magnetic Resonance Spectroscopy, J. Am. Oil Chem. Soc. 73, 1611-1613.
18. Itabashi, Y., and Takagi, T. (1982) Cis-5-Olefinic Nonmethylene-Interrupted Fatty Acids in Lipids of Seeds, Arils, and Leaves of Japanese Yew, Yukagaku 31, 574-579.
19. Wolff, R.L., Deluc, L.G., and Marpeau, A.M. (1996) Conifer Seeds: Oil Content and Fatty Acid Distribution, J. Am. Oil Chem. Soc. 73, 765-771.
20. Wolff, R.L., Christie, W.W., and Coakley, D. (1997) Bishomopinolenic (7,11,14-20:3) Acid in Pinaceae Seed Oils, J. Am. Oil Chem. Soc. 74, 1583-1586.
21. Berger, A., and German, J.B. (1991) Extensive Incorporation of Dietary Δ-5,11,14 Eicosatrienoate into the Phosphatidylinositol Pool, Biochim. Biophys. Acta 1085, 371-376.
22. Ikeda, I., Oka, T., Koba, K., Sugano, M., and Lie Ken Jie, M.S.F. (1992) 5c,11c,14c Eicosatrienoic and 5c,11c,14c,17c-Eicosatetraenoic Acid of Biota orientalis Seed Oil Affect Lipid Metabolism in the Rat. Upids 27, 500-504.
23. Sugano, M., Ikeda, I., and Lie Ken Jie, M.S.F. (1992) Polyunsaturated Fatty Acid Regulation of Cholesterol Metabolism and Eicosanoid Production in Rats: Effects of Uncommon Fatty Acids, in Essential Fatty Acids and Eicosanoids: Invited Papers from the Third International Congress (Sinclair, A., and Gibson, R., eds.), pp. 268-270, American Oil Chemists' Society, Champaign.
24. Berger, A., Fenz, R., and German, J.B. (1993) Incorporation of Dietary 5,11,14-Icosatrienoate into Various Mouse Phospholipid Classes and Tissues, J. Nutr. Biochem. 4, 409-420.
25. Sugano, M., Ikeda, I., Wakamatsu, K., and Oka, T. (1994) Influence of Korean Pine (Pinus koraiensis)-Seed Oil Containing cis-5,cis-9,cis-12-Octadecatrienoic Acid on Polyunsaturated Fatty Acid Metabolism, Eicosanoid Production and Blood Pressure of Rats, Br. J. Nutr. 72, 775-783.
26. Lai, L.T., Naiki, M., Yoshida, S.H., German, J.B., and Gerschwin, M.E. (1994) Dietary Platycladus orientalis Seed Oil Suppresses Anti-Erythrocyte Autoantibodies and Prolongs Survival of NZB Mice, Clin. Immunol. Immunopathol. 71, 293-302.
27. Matsuo, N., Osada, K., Kodama, T., Lim, B.O., Nakao, A., Yamada, K., and Sugano, M. (1996) Effects of Gamma-Linolenic Acid and Its Positional Isomer Pinolenic Acid on Immune Parameters of Brown-Norway Rats. Prostaglandins Leukotrienes Essent. Fatty Acids 55, 223-229.
28. Yoshida, S.U., Siu, J., Griffey, S.M., German, J.B., and Gerschwin, M.E. (1996) Dietary Juniperis virginienxis (sic) Seed Oil Decreased Pentobarbital-Associated Mortalities Among DBA/I Mice Treated with Collagen-Adjuvant Emulsions, J. Lipid Mediat. Cell. Signal. 13, 283-293.
29. Chavali, S.R., Weeks, C.E., Zhong, W.W., and Forse, R.A. (1998) Increased Production of TNF-α and Decreased Levels of Dienoic Eicosanoids, IL-6and IL-10 in Mice Fed Menhaden Oil and Juniper Oil Diets in Response to an Intraperitoneal Lethal Dose of LPS, Prostaglandins Leukotrienes Essent. Fatty Acids 59, 89-93.
30. Asset, G., Staels, B., Wolff, R.L., Baugé, E., Fruchart, J.C., and Dallongeville, J. (1999) Effects of Pinus pinaster and Pinus koraieusis Seed Oil Supplementation on Lipoprotein Metabolism in Rats, Lipids 34, 39-44.
31. Wolff, R.L. (1997) New Tools to Explore Lipid Metabolism, INFORM 8, 116-119.
32. Wolff, R.L., Marpeau, A.M., Gunstone, F.D., Bézard, J., Farines, M., Martin, J.C., and Dallongeville, J. ( 1997) Particularités Structurales et Physiologiques d'Huiles Nouvelles, les Huiles de Graines de Conifères, Oléagineux 4, 65-70 (in French).
33. Aitzetmüller, K. (1998) Komaroffia Oils - An Excellent New Source of Δ5-Unsaturated Fatty Acids, J. Am. Oil Chem. Soc. 75, 1897-1899.
34. Takagi, T., and Itabashi, Y. (1982) cis-5 Olefinic Unusual Fatty Acids in Seed Lipids of Gymnospermae and Their Distribution in Triacylglycerols, Lipids 17, 716-723.
35. Groenewald, E.G., and van der Westhuizen, J. (1997) Prostaglandins and Related Substances in Plants, Bot. Rev. 63, 199-220.
36. Jamieson, G.R., and Reid, E.H. (1972) The Leaf Lipids of Some Conifer Species, Phytochemistry 11, 269-275.
37. Wolff, R.L., Christie, W.W., and Coakley, D. (1997) The Unusual Occurrence of 14-Methylhexadecanoic Acid in Pinaceae Seed Oils Among Plants, Lipids 32, 971-973.
38. Little, E.L., Jr., and Critchfield, W.B. (1969) Subdivision of the Genus Pinus (Pines), U.S. Department of Agriculture, Forest Service, Miscellaneous Publication No. 1144, Washington, DC, 51 pp.
39. Debazac, E.B. (1964) Manuel des Conifères, Ecole Nationale des Eaux et Forêts, Nancy, pp. 23-112 (in French).
40. Mirov, N.T. (1961) Composition of Gum Turpentines of Pines, U.S. Department of Agriculture, Forest Service Technical Bulletin No. 1239, Washington, DC, 158 pp.
41. Critchfield, W.B. (1986) Hybridization and Classification of the White Pines (Pinus Section Strobus), Taxon 35, 647-656.
42. Klaus, W. (1989) Mediterranean Pines and Their History, Plant Syst. Evol. 162, 133-163.
43. Farjon, A., and Styles, B. (1997) Pinus L. (Pinaceae), Flora Neotropica Monograph 75, New York Botanical Garden, Bronx, New York.
44. Malusa, J. (1992) Phylogeny and Biogeography of the Pinyon Pines (Pinus subsect. Cembroides), Syst. Bot. 17, 42-66.
45. Strauss, S.H., and Doerksen, A.H. (1990) Restriction Fragment Analysis of Pine Phylogeny, Evolution 44, 1081-1096.
46. Wang, X.-R., and Szmidt, A.I. (1993) Chloroplast DNA-Based Phylogeny of Asian Pinus Species (Pinaceae), Plant Syst. Evol. 188, 197-211.
47. Chaw, S.-M., Zharkikh, A., Sung, H.-M., Lau, T.-C., and Li, W.-H. (1997) Molecular Phylogeny of Extant Gymnosperms and Seed Plant Evolution: Analysis of Nuclear 18S rRNA Sequences, Molec. Biol. Evol. 14, 56-60.
48. Carlisle, A. (1958) A Guide to the Named Variants of Scots Pine (Pinus sylvestris Linnaeus), Forestry (Oxford) 31, 203-224.
49. Christensen, K.I. (1987) Taxonomic Revision of the Pinus mugo Complex and P. × rhaetica (P. mugo × sylvestris) (Pinaceae), Nord. J. Bot. 7, 383-408.
50. Tillman-Sutela, E., Johanson, A., Laakso, R., Manila, T., and Kallio, H. (1995) Triacylglycerols in the Seeds of Northern Scots Pine, Pinus sylvestris L. and Norway Spruce, Picea abies (L.) Karst, Trees 10, 40-45.
51. Wolff, R.L., Pédrono, F., and Marpeau, A.M. (1999) Fatty Acid Composition of Edible Pine Seeds with Emphasis on North American and Mexican Pines of the Cembroides Subsection, Oléagineux 6, 107-110.
52. Hirata, Y., Sekiguchi, R., Saitoh, M., Kubota, K., and Kayama, M. (1994) Components of Pine Seed Lipids, Yukagaku 43, 579-582 (in Japanese).
53. Imbs, A.B., and Pham, L.Q. (1996) Fatty Acids and Triacylglycerols in Seeds of Pinaceae Species, Phytochemistry 42, 1051-1053.
54. Kim, S.-J., Kim, G.-S., Yi, M.-O., and Joh, Y.-G. (1992) Fatty Acid Compositions of Some Seed Oils from the Pinaceae Family, J. Korean Oil Chem. Soc. 9, 149-156 (in Korean).
55. Hu, Z.-L., Li, X.-P., and Bao, H. (1992) Distribution of Fatty Acids from the Pinus Seed Oils and the Chemotaxonomic Survey, J. Plant Res. Environ. (Zhiwu Ziyuan Yu Huanjing) 1, 15-18 (in Chinese).
56. Wolff, R.L., and Bayard, C.C. (1995) Fatty Acid Composition of Some Pine Seed Oils, J. Am. Oil Chem. Soc. 72, 1043-1046.
57. Wolff, R.L., and Marpeau, A.M. (1997) Δ5-Olefinic Acids in the Edible Seeds of Nut Pine (Pinus cembroides edulis) from the United States, J. Am. Oil Chem. Soc. 74, 613-614.
58. Wolff, R.L. (1998) A Practical Source of Δ5-Olefinic Acids for Identification Purposes, J. Am. Oil Chem. Soc. 75, 891-892.
59. Imbs, A.B., Nevshupova, N.V., and Pham, L.Q. (1998) Triacyl Composition of Pinus koraiensis Seed Oil, J. Am. Oil Chem. Soc. 75, 865-870.
60. De Ferré, Y. (1966) Validité de l'Espèce Pinus pumila et Affinités Systématiques, Bull. Soc. Hist. Nat. Toulouse 102, 351-356 (in French).
61. Zavarin, E., Snajberk, K., and Cool, L. (1990) Chemical Differentiation in Relation to the Morphology of the Single-Needle Pinyons, Biochem. Syst. Ecol. 18, 125-137.
62. Sagrero-Nieves, L. (1992) Fatty Acid Composition of Mexican Nut (Pinus cembroides) from Three Seed Coat Phenotypes, J. Sci. Food Agric. 59, 413-414.
63. Zavarin, E. (1987) Taxonomy of Pinyon Pines, in Proceedings of II Simposio Nacional sobre Pinos Piñoneros (Passini, M.F., Tovar, D.C., and Eguiluz Piedra, T., eds.), pp. 29-40, CEMCA, Mexico City, Mexico.
64. Janick, J., Cabral Velho, C., and Whipkey, A. (1991) Developmental Changes in Seeds of Loblolly Pine, J. Am. Soc. Hort. Sci. 116, 297-301.
65. Laseter, J.L., Lawler, G.C., Walkinshaw, C.H., and Weete, J.D. (1972) Fatty Acids of Pinus elliottii Tissues, Photochemistry 12, 817-821.
66. Yazicioglu, T., and Karaali, A. (1983) On the Fatty Acid Composition of Turkish Vegetable Oils, Fette Seifen Anstrichm. 85, 23-29.
67. Ickert-Bond, S.M. (1997) Pinus krempfii Lec. - A Vietnamese Conifer with Problematic Affinities, Am. J. Bot. 84, 203 (abstract).
68. Frankis, M.P. (1988) Generic Inter-Relationships in Pinaceae, Notes RBG Edinb. 45, 527-548.
69. Hart, J.A. (1987) A Cladistic Analysis of Conifers: Preliminary Results, J. Arnold Arbor. 68, 269-307.
70. Price, R.A., and Olsen-Stojkovich, J. (1987) Relationships Among the Genera of Pinaceae: An Immunological Comparison, Syst. Bol. 12, 91-97.
71. Prager, E.M., Fowler, D.P., and Wilson, A. (1976) Rates of Evolution in Conifers (Pinaceae), Evolution 30, 637-649.
72. Suzuki, M. (1979) The Course of Resin Canals in the Shoots of Conifers. III. Pinaceae and Summary Analysis, Bot. Mag. Tokyo 92, 333-353.
73. Aitzetmüller, K., and Tsevegsüren, N. (1994) Seed Fatty Acids. "Front-End"-Desaturases and Chemotaxonomy - A Case Study in the Ranunculaceae, J. Plant Physiol. 143, 538-543.
74. Berger, J.J. (1999) Additif Alimentaire, Composition Cosmétique et Médicament à Base d'Huile de Graines de Pin, French Patent 96 14794.
75. Medvedev, F.A., Kilakova, S.J., and Levatchev, M.M. (1992) Characteristics of Fatty Acid Composition of Pine Kernels in Siberia and Far East, Voprosy Pitania 2, 70-71 (in Russian).