Cyclopropenoid fatty acids in<i>gnetum scandens and itsterculia pallens</i> seed oils

Mustafa, Jamal; Gupta, Amit K.; Ahmad, M. S.; Ahmad, Faheem; Osman, S. M.

doi:10.1007/bf02663950

Cited by 16 publications

(10 citation statements)

References 2 publications

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“…However, there exists exceptions, Welwitschia mirabilis and Gnetum spp. (from the strange gymnosperm group, Gnetales, also considered a subphylum, Chlamydosperms), the seed lipids of which contain cyclopropenoic acids and no ∆5-UPIFA [53][54][55]. It is estimated that there are approximately 250,000 angiosperm species, or even more, whereas the number of gymnosperm species is considerably lower, between ca.…”

Section: ∆ ∆5-upifa Are Usual Components Of Gymnosperm Lipidsmentioning

confidence: 99%

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

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Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis ∆ ∆5-olefinic acidsIn view of the increasing interest of lipid researchers in the biological effects of all-cis ∆5-unsaturated polymethylene-interrupted fatty acids (∆5-UPIFA) from vegetable origin, this paper is concerned with their occurrence in practical sources (gymnosperm seeds), structures, and identification by gas-liquid chromatography (GLC) and mass spectrometry (MS). The use of equivalent chain lengths (ECL) determined by calculations based on available standards, in close agreement with data determined with easily available commercial gymnosperm seeds specific for each ∆5-UPIFA, allows identification of all ∆5-UPIFA. These tentative identifications are supported by GLC-MS of the appropriate (4,4-dimethyloxazoline and picolinyl ester) derivatives. ECL are particularly useful to identify ∆5-UPIFA in tissue lipids from animals experimentally fed oils containing these acids, with no interference with polyunsaturated fatty acids of endogenous origin.

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Section: ∆ ∆5-upifa Are Usual Components Of Gymnosperm Lipidsmentioning

confidence: 99%

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

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“…Although the peculiar ∆5-unsaturated polymethylene-interrupted fatty acids (∆5-UPIFA) found in gymnosperms were structurally characterized almost 40 yr ago (19)(20)(21)(22), and have been repeatedly reported to occur in a few species since then, their ubiquity in the seeds of practically all gymnosperm species was not recognized until recently (23,24). However, exceptions are known [Gnetaceae (25) and Welwitschiaceae (26)]. …”

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confidence: 98%

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

Wolff

Christie

Pédrono

et al. 1999

Lipids

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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) acids for the first time in the seed oil of a higher plant. They were apparently derived from gamma-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-gamma-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-alpha-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 delta5-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 delta6- and delta5-desaturase activities in A. robusta seeds. The delta6-ethylenic bond is apparently introduced into C18 polyunsaturated acids, whereas the delta5-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 delta6-desaturase/C18-->C20 elongase/C20 delta5-desaturase system in common with the former subphyla, and the unsaturated C18-->C20 elongase/C20 delta5-desaturase system specific to gymnosperms. The following hypothetical evolutionary sequence for the C18 delta6/delta5-desaturase class in gymnosperm seeds is suggested: delta6 (initial)-->delta6/delta5 (intermediate)-->delta5 (final).

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“…(Ephedraceae) seeds containing fairly large amounts of ∆5-UPIFA including sciadonic acid (10) and Welwitschia mirabilis (Welwitschiaceae) (15) and Gnetum spp. (Gnetaceae) (16,17) seeds containing no such acids. In lieu of ∆5-UPIFA, the two latter families contain cyclopropene and sometimes cyclopropane fatty acids.…”

mentioning

confidence: 99%

The phylogenetic significance of sciadonic (all‐cis 5,11,14–20:3) acid in gymnosperms and its quantitative significance in land plants

Wolff

1999

J Americ Oil Chem Soc

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Cyclopropenoid fatty acids ingnetum scandens and itsterculia pallens seed oils

Cited by 16 publications

References 2 publications

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

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

The phylogenetic significance of sciadonic (all‐cis 5,11,14–20:3) acid in gymnosperms and its quantitative significance in land plants

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