Fatty acid diversity of Section Inflexae Limnanthes (meadowfoam)

Knapp, Steven J.; Crane, J. M.

doi:10.1016/0926-6690(95)00035-b

Cited by 19 publications

(19 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…contain ∆5-monoenoic acids, and trans ∆5-UPIFA are known in two or three angiosperm species (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). The first report on the fatty acid composition of the seed lipids from a Cycadophyte species was probably that of Kleiman et al (27), which was published more than 30 yr ago.…”

Section: ∆5-olefinic Acids In the Seed Lipids From Four Ephedra Specimentioning

confidence: 99%

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

Wolff

Christie

Pédrono

et al. 1999

Lipids

View full text Add to dashboard Cite

The fatty acid compositions of the seed lipids from four Ephedra species, E. nevadensis, E. viridis, E. przewalskii, and E. gerardiana (four gymnosperm species belonging to the Cycadophytes), have been established with an emphasis on delta5-unsaturated polymethylene-interrupted fatty acids (delta5-UPIFA). Mass spectrometry of the picolinyl ester derivatives allowed characterization of 5,9- and 5,11-18:2; 5,9,12-18:3; 5,9,12,15-18:4; 5,11-20:2; 5,11,14-20:3; and 5,11,14,17-20:4 acids. Delta5-UPIFA with a delta11-ethylenic bond (mostly C20 acids) were in higher proportions than delta5-UPIFA with a delta9 double bond (exclusively C18 acids) in all species. The total delta5-UPIFA content was 17-31% of the total fatty acids, with 5,11,14-20:3 and 5,11,14,17-20:4 acids being the principal delta5-UPIFA isomers. The relatively high level of cis-vaccenic (11-18:1) acid found in Ephedra spp. seeds, the presence of its delta5-desaturation product, 5,11-18:2 acid (proposed trivial name: ephedrenic acid), and of its elongation product, 13-20:1 acid, were previously shown to occur in a single other species, Ginkgo biloba, among the approximately 170 gymnosperm species analyzed so far. Consequently, Ephedraceae and Coniferophytes (including Ginkgoatae), which have evolved separately since the Devonian period (approximately 300 million yr ago), have kept in common the ability to synthesize C18 and C20 delta5-UPIFA. We postulate the existence of two delta5-desaturases in gymnosperm seeds, one possibly specific for unsaturated acids with a delta9-ethylenic bond, and the other possibly specific for unsaturated acids with a delta11-ethylenic bond. Alternatively, the delta5-desaturases might be specific for the chain length with C18 unsaturated acids on the one hand and C20 unsaturated acids on the other hand. The resulting hypothetical pathways for the biosynthesis of delta5-UPIFA in gymnosperm seeds are only distinguished by the position of 11-18:1 acid. Moreover, 13C nuclear magnetic resonance spectroscopy of the seed oil from two Ephedra species has shown that delta5-UPIFA are essentially excluded from the internal position of triacylglycerols, a characteristic common to all of the Coniferophytes analyzed so far (more than 30 species), with the possibility of an exclusive esterification at the sn-3 position. This structural feature would also date back to the Devonian period, but might have been lost in those rare angiosperm species containing delta5-UPIFA.

show abstract

Section: ∆5-olefinic Acids In the Seed Lipids From Four Ephedra Specimentioning

confidence: 99%

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

Wolff

Christie

Pédrono

et al. 1999

Lipids

View full text Add to dashboard Cite

show abstract

“…Fatty acids with D5 unsaturation are also the major components of meadowfoam oil, obtained from the seeds of Limnanthes alba [2]. This oil contains an unusual VLC-PMIFA, docosa-5-cis,13-cis-dienoic acid (22:2D5,13), that accounts for up to 16% of total seed fatty acids [3,4].…”

Section: Introductionmentioning

confidence: 99%

Overexpression of a FAD3 Desaturase Increases Synthesis of a Polymethylene‐Interrupted Dienoic Fatty Acid in Seeds of Arabidopsis thaliana L.

Puttick

Dauk

Lozinsky

et al. 2009

Lipids

View full text Add to dashboard Cite

A cDNA encoding the Arabidopsis extraplastidic linoleate desaturase (FAD3) was overexpressed in the seeds of wild‐type Arabidopsis and in a mutant line that accumulates high levels of oleic acid. In the transformed wild‐type plants, linolenic acid (18:3Δ9,12,15) increased from 19% to nearly 40% of total seed fatty acids, with a corresponding decrease in linoleate content (18:2Δ9,12). In the high oleate mutant, a large increase in the level of a fatty acid identified by gas‐chromatography/mass‐spectrometry as mangiferic acid (18:2Δ9,15) was observed. The results demonstrate that the polymethylene‐interrupted dienoic fatty acid, mangiferic acid, can be produced in seed oil through the overexpression of a fatty acid n‐3 desaturase.

show abstract

“…The seed oil of meadowfoam is a rich source of novel very long-chain fatty acids (C 20 and C 22 ) (Smith et al 1960;Bagby et al 1961). The oil has unusually high concentrations of D5 unsaturated (typically 86%) and C 20 and C 22 (typically 96%) fatty acids and extraordinarily low concentrations of saturated fatty acids (typically less than 2%) (Knapp and Crane 1995). The novelty of the oil has been the primary factor behind the development of the meadowfoam oil industry and, more recently, the development of novel chemical derivatives for industrial markets (Isbell 1997).…”

Section: Introductionmentioning

confidence: 99%

“…The early wild collections and a few domesticated germplasm accessions are maintained by the United States Department of Agriculture National Plant Germplasm System (http://www.ars-grin.gov/npgs), and have supplied genetic diversity crucial for meadowfoam cultivar development and, consequently, for the development of the meadowfoam oil industry. Genetic diversity for several biologically and agriculturally important traits has been surveyed and cataloged in cultivated meadowfoam (Knapp and Crane 1995, 1997; however, molecular genetic diversity has not been surveyed, essentially because high-throughput, meadowfoam-specific DNA markers have not been developed.…”

Section: Introductionmentioning

confidence: 99%

Conserved simple sequence repeats for the Limnanthaceae (Brassicales)

et al. 2003

View full text Add to dashboard Cite

The Limnanthaceae (Order Brassicales) is a family of 18 taxa of Limnanthes (meadowfoam) native to California, Oregon, and British Columbia. Cultivated meadowfoam ( L. alba Benth.), a recently domesticated plant, has been the focus of research and development as an industrial oilseed for three decades. The goal of the present research was to develop several hundred simple sequence repeat (SSR) markers for genetic mapping, molecular breeding, and genomics research in wild and cultivated meadowfoam taxa. We developed 389 SSR markers for cultivated meadowfoam by isolating and sequencing 1,596 clones from L. alba genomic DNA libraries enriched for AG(n) or AC(n) repeats, identifying one or more unique SSRs in 696 clone sequences, and designing and testing primers for 624 unique SSRs. The SSR markers were screened for cross- taxa utility and polymorphisms among ten of 17 taxa in the Limnanthaceae; 373 of these markers were polymorphic and 106 amplified loci from every taxon. Cross-taxa amplification percentages ranged from 37.3% in L. douglasii ssp. rosea (145/389) to 85.6% in L. montana (333/389). The SSR markers amplified 4,160 unique bands from 14 genotypes sampled from ten taxa (10.7 unique bands per SSR marker), of which 972 were genotype-specific. Mean and maximum haplotype heterozygosities were 0.71 and 0.90, respectively, among six L. alba genotypes and 0.63 and 0.93, respectively, among 14 genotypes (ten taxa). The SSR markers supply a critical mass of high-throughput DNA markers for biological and agricultural research across the Limnanthaceae and open the way to the development of a genetic linkage map for meadowfoam ( x = 5).

show abstract

Fatty acid diversity of Section Inflexae Limnanthes (meadowfoam)

Cited by 19 publications

References 23 publications

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

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

Overexpression of a FAD3 Desaturase Increases Synthesis of a Polymethylene‐Interrupted Dienoic Fatty Acid in Seeds of Arabidopsis thaliana L.

Conserved simple sequence repeats for the Limnanthaceae (Brassicales)

Contact Info

Product

Resources

About