Chromatographic analysis of seed oils. II. fatty acid composition of dimorphotheca oil

Binder, Ronald G.; Applewhite, T. H.; Diamond, M. J.; Goldblatt, L. A.

doi:10.1007/bf02673484

Cited by 42 publications

(10 citation statements)

References 12 publications

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“…13 To this aim, the synthesis of the two enantiomers in almost pure form was realized starting from Dimorphoteca sinuata L. seeds, containing a natural precursor bearing the hydroxyl functionality on the enatiomerically pure chiral center in position 9. 14 At variance, classical enantioselective synthetic methods or kinetic resolution methods revealed to be not su ccessful for the synthesis of the two acids in enantiomerically pure form, due to the high symmetry around the chiral center of these compounds. 15 In this work, we explored the possibility to functionalize HA with HSA with the objective to obtain composite nanocrystals with modulated cytotoxic effect on cancer cells.…”

Section: Introductionmentioning

confidence: 99%

“…This prediction was confirmed by administering ( 9R )-9-HSA and ( 9S )-9-HSA to HT-29 cells . To this aim, the synthesis of the two enantiomers in almost pure form was realized starting from Dimorphoteca sinuata L. seeds, containing a natural precursor bearing the hydroxyl functionality on the enatiomerically pure chiral center in position 9 . At variance, classical enantioselective synthetic methods or kinetic resolution methods were revealed to be not successful for the synthesis of the two acids in enantiomerically pure form due to the high symmetry around the chiral center of these compounds …”

Section: Introductionmentioning

confidence: 99%

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(9R)-9-Hydroxystearate-Functionalized Hydroxyapatite as Antiproliferative and Cytotoxic Agent toward Osteosarcoma Cells.

et al. 2015

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The possibility to functionalize calcium phosphates with bioactive agents is a promising strategy to design innovative biomaterials for bone repair able to couple the bioactive properties of the inorganic compounds with the therapeutic effect of the functionalizing agent. The R enantiomer of the 9-hydroxystearic acid, (9R)-9-HSA, produced from Dimorphotheca sinuata L. seeds, has proven to act as a natural negative regulator of tumor cell proliferation. On this basis, hydroxyapatite was synthesized with increasing contents of (9R)-9-hydroxystearate, up to ∼8.6 wt %. The incorporation of HSA in the composite nanocrystals induces a reduction of the crystal mean dimensions and of the length of the coherently scattering crystalline domains, which suggest a preferential adsorption onto the hydroxyapatite crystal faces parallel to the c-axis direction. The composite nanocrystals were designed so that their cytostatic and cytotoxic effects toward osteosarcoma cells were modulated by hydroxystearate content. In fact, results of in vitro tests show that the presence of HSA in the composite nanocrystals provokes a significant decrease in SaOS2 osteosarcoma cells proliferation and viability as well as an increase in lactate dehydrogenase, tumor necrosis factor α, and caspase 3 levels, with a cytotoxic effect increasing with HSA content in the nanocrystals.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

(9R)-9-Hydroxystearate-Functionalized Hydroxyapatite as Antiproliferative and Cytotoxic Agent toward Osteosarcoma Cells.

et al. 2015

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“…Many of such natural keto fatty acids were found in plants, mainly as a constituent of seed oil [21][22][23][24][25][26][27][28][29]. Among them, rabdosia acids [30] and (10E,12E)-9-oxo-10,12octadecadienoic acid [31] are the plant keto fatty acids containing the dienone moiety with trans,trans-configuration, but congeners with trans,cis-configuration have not been found in nature until the present work ( Figure 4). Some of the keto fatty acids of plant origin were shown to exhibit pharmaceutically important activity.…”

Section: Resultsmentioning

confidence: 99%

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

Sharma¹,

Harunari²,

Oku³

et al. 2020

Beilstein J. Org. Chem.

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A pair of geometrically isomeric unsaturated keto fatty acids, (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2), were isolated from the culture broth of an actinomycete of the genus Micrococcus, which was associated with a stony coral, Catalaphyllia sp. Their chemical structures were elucidated by spectroscopic analysis including NMR and MS, with special assistance of spin system simulation studies for the assignment of an E geometry at C8 in 2. As metabolites of microbes, compounds 1 and 2 are unprecedented in terms of bearing a 2,4-dienone system. Both 1 and 2 showed antibacterial activity against the plant pathogen Rhizobium radiobacter and the fish pathogen Tenacibaculum maritimum, with a contrasting preference that 1 is more effective to the former strain while 2 is so to the latter. In addition, compounds 1 and 2 displayed agonistic activity against peroxisome proliferator-activated receptors (PPARs) with an isoform specificity towards PPARα and PPARγ.

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“…They fractionated the 14 C-acetylated oil by thin-layer chromatography (TLC), and the content of fatty acids with one, two or three hydroxy groups was determined by measuring the radioactivity of each fraction. Gas chromatography (GC), followed by titrimetric analysis, of fatty acids from D. sinuata has been used to determine the total amount of mono-and polyhydroxy acids in the oil (8). Alkali-catalyzed transesterification of glycerides by means of anion-exchange resin columns, followed by GC analysis, has been used to determine the fatty acid composition in D. sinuata oil (8,9).…”

mentioning

confidence: 99%

“…Gas chromatography (GC), followed by titrimetric analysis, of fatty acids from D. sinuata has been used to determine the total amount of mono-and polyhydroxy acids in the oil (8). Alkali-catalyzed transesterification of glycerides by means of anion-exchange resin columns, followed by GC analysis, has been used to determine the fatty acid composition in D. sinuata oil (8,9). GC analysis of methyl esters of hydroxy fatty acids is, however, not quantitative because the long retention times and high temperatures required often cause some thermal degradation of hydroxy fatty acids.…”

mentioning

confidence: 99%

Analysis of seed oil from ricinus communis and dimorphoteca pluvialis by gas and supercritical fluid chromatography

Borch-Jensen

Jensen

Mathiasen

et al. 1997

J Americ Oil Chem Soc

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The seed oils from Dimorphoteca pluvialis and Ricinus communis contain hydroxy fatty acids. Dimorphoteca pluvialis contains ∆-9-hydroxy-10t,12t-octadecadienoic acid (dimorphecolic acid) and R. communis contains ∆-12-hydroxy9c-octadecenoic acid (ricinoleic acid). The oils were derivatized and analyzed to determine the content of hydroxy fatty acids. The trimethylsilyl fatty acid methyl ester (TMS-FAME) derivatives were analyzed by capillary gas chromatography (GC), and the free fatty acid (FFA) derivatives and the oils were analyzed by capillary supercritical fluid chromatography (SFC). Further, mass spectroscopy of the TMS-FAME derivatives was performed to check the purity of the derivatives. The results from the GC analyses of TMS-FAME corresponded to the results found by SFC analysis of the FFA. The content of ricinoleic acid in the glycerolipids of R. communis was 87.7 wt%, and the content of dimorphecolic acid in D. pluvialis was 54.0 wt%. The methods were evaluated with respect to the cost, ease, and time needed for sample preparation and analysis. JAOCS 74, 277-284 (1997).

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Chromatographic analysis of seed oils. II. fatty acid composition of dimorphotheca oil

Cited by 42 publications

References 12 publications

(9R)-9-Hydroxystearate-Functionalized Hydroxyapatite as Antiproliferative and Cytotoxic Agent toward Osteosarcoma Cells.

(9R)-9-Hydroxystearate-Functionalized Hydroxyapatite as Antiproliferative and Cytotoxic Agent toward Osteosarcoma Cells.

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

Analysis of seed oil from ricinus communis and dimorphoteca pluvialis by gas and supercritical fluid chromatography

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