Sources of 5,11,14‐20:3 (sciadonic) acid, a structural analog of arachidonic acid

Wolff, Robert Lee

doi:10.1007/s11746-998-0349-4

Cited by 12 publications

(13 citation statements)

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“…On the contrary, they are the rule. This was observed in earlier and more recent systematic studies of gymnosperm leaf [28,29] and seed lipids [30], and for the latter, extended to practically all species analysed so far (approximately 170 species analysed by author Wolff and co-workers [26,27,[31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46]). They also occur in wood [47][48][49][50][51][52] lipids, but the number of species analysed for these tissues is much more limited.…”

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

confidence: 56%

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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 Lipidssupporting

confidence: 56%

“…7%). However, several other conifers have considerably higher sciadonic acid contents (e.g., 26% in Nageia nagi, slightly less in Prumnopitys andinus, Cephalotaxus spp., and certainly many other species) [41].…”

Section: Practical Sources Of Individual ∆ ∆5-upifa As Standards For Glcmentioning

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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“…170 species have been analyzed in our Institutes, which represent approximately one-fourth of all extant species from this plant group. The species analyzed belong to the families Taxaceae, Cephalotaxaceae, Podocarpaceae, Pinaceae, Taxodiaceae, Cupressaceae, Sciadopityaceae, Ginkgoaceae, Cycadaceae, and Ephedraceae (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). 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).…”

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confidence: 99%

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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“…Such values are commonly found in the seed lipids from many other Coniferophytes (9)(10)(11)13,14) and some Cycadophytes (Wolff, R.L., W.W. Christie, F. Pédrono, A.M. Marpeau, N. Tsevegsüren, K. Aitzetmüller, and F.D. Gunstone, unpublished data).…”

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confidence: 69%

“…On the other hand, "sciadonic" acid seems appropriate for 5,11,14-20:3 acid, as it is the major ∆5-UPIFA in Sciadopitys verticillata seed lipids (8,10,11,13,14). This species was formerly classified in the Taxodiaceae family (15), while it is now increasingly recognized as the sole extant species of the monotypic Sciadopityaceae family (12,16).…”

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confidence: 99%

All‐cis 5,11,14‐20:3 acid: Podocarpic acid or sciadonic acid?

Wolff

1999

J Americ Oil Chem Soc

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Sources of 5,11,14‐20:3 (sciadonic) acid, a structural analog of arachidonic acid

Cited by 12 publications

References 7 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

All‐cis 5,11,14‐20:3 acid: Podocarpic acid or sciadonic acid?

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