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Arachidonic, eicosapentaenoic, and biosynthetically related fatty acids in the seed lipids from a primitive gymnosperm, Agathis robusta

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Lipids

Abstract

The fatty acid composition of the seeds from Agathis robusta, an Australian gymnosperm (Araucariaceae), was determined by a combination of chromatographic and spectrometric techniques. These enabled the identification of small amounts of arachidonic (5,8,11,14–20∶4) and eicosapentaenoic (5,8,11,14,17–20∶5) acid for the first time in the seed oil of a higher plant. They were apparently derived from γ-linolenic (6,9,12–18∶3) and stearidonic (6,9,12,15–18∶4) acids, which were also present, via chain elongation and desaturation, together with other expected biosynthetic intermediates [bis-homo-γ-linolenic (8,11,14–20∶3) and bishomo-stearidonic (8,11,14,17–20∶4) acids]. Also present were a number of C20 fatty acids, known to occur in most gymnosperm families, i.e., 5,11–20∶2, 11,14–20∶2 (bishomo-linoleic), 5,11,14–20∶3 (sciadonic), 11,14,17–20∶3 (bishomo-α-linolenic), and 5,11,14,17–20∶4 (juniperonic) acids. In contrast to most other gymnosperm seed lipids analyzed so far, A. robusta seed lipids did not contain C18 Δ5-desaturated acids [i.e., 5,9–18∶2 (taxoleic), 5,9,12–18∶3 (pinolenic), or 5,9,12,15–18∶4 (coniferonic)]. These structures support the simultaneous existence of Δ6- and Δ5-desaturase activities in A. robusta seeds. The Δ6-ethylenic bond is apparently introduced into C18 polyunsaturated acids, whereas the Δ5-ethylenic bond is introduced into C20 polyunsaturated acids. A general metabolic pathway for the biosynthesis of unsaturated fatty acids in gymnosperm seeds is proposed. When compared to Bryophytes, Pteridophytes (known to contain arachidonic and eicosapentaenoic acids), and species from other gymnosperm families (without such acids), A. robusta appears as an “intermediate,” with the C18 Δ6-desaturase/C18→C20 elongase/C20 Δ5-desaturase system in common with the former subphyla, and the unsaturated C18→C20 elongase/C20 Δ5-desaturase system specific to gymnosperms. The following hypothetical evolutionary sequence for the C18 Δ6/Δ5-desaturase class in gymnosperm seeds is suggested: Δ6 (initial)→Δ6/Δ5 (intermediate)→Δ5 (final).

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Abbreviations

DMOX:

dimethyloxazoline

ECL:

equivalent chain length

FAME:

fatry-acid methyl ester

GLC:

gas-liquid chromatography

HPLC:

high-performance liquid chromatography

MS:

mass spectrometry

NMR:

nuclear magnetic resonance

TAG:

triacylglycerol

TLC:

thin-layer chromatography

UPIFA:

unsaturated polymethylene-interrupted fatty acid

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Authors and Affiliations

  1. Scottish Crop Research Institute, Dundee, Scotland

    William W. Christie

  2. Institut du Pin, Université Bordeaux 1, Talence, France

    Anne M. Marpeau

  3. ISTAB, Université Bordeaux 1, Av. des Facultés, 33405, Tarence Cedex, France

    Robert L. Wolff & Frédérique Pédrono

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  1. Robert L. Wolff
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  2. William W. Christie
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  3. Frédérique Pédrono
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  4. Anne M. Marpeau
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Correspondence to Robert L. Wolff.

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Wolff, R.L., Christie, W.W., Pédrono, F. et al. Arachidonic, eicosapentaenoic, and biosynthetically related fatty acids in the seed lipids from a primitive gymnosperm, Agathis robusta . Lipids 34, 1083–1097 (1999). https://doi.org/10.1007/s11745-999-0460-y

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