Oleic Acid Is not the Only Relevant Mono-Unsaturated Fatty Ester in Olive Oil

(1) Background: Extra-virgin olive oil (EVOO) is a precious and universally studied food matrix. Recently, the quantitative chemical composition was investigated by an innovative processing method for the nuclear magnetic resonance (NMR) experiments called Multi-Assignment Recovered Analysis (MARA)-NMR. (2) Methods: Any EVOO 13-carbon NMR (13C-NMR) profile displayed inconsistent signals. This mismatch was resolved by comparing NMR data to the official gas-chromatographic flame ionization detection (GC-FID) experiments: the analyses concerned many EVOOs but also the “exotic” Capparis spinosa oil (CSO). (3) Results: NMR and GC-FID evidenced the overwhelming presence of cis-vaccenic esters in the CSO and, more importantly, cis-vaccenic 13C-NMR resonances unequivocally matched the misunderstood 13C-NMR signals of EVOOs. The updated assignment revealed the unexpected relevant presence of cis-vaccenic ester (around 3%) in EVOOs; it was neglected, so far, because routine and official GC-FID profiles did not resolve oleic and cis-vaccenic signals leading to the total quantification of both monounsaturated fatty esters. (4) Conclusions: The rebuilt MARA-NMR and GC-FID interpretations consistently show a meaningful presence of cis-vaccenic esters in EVOOs, whose content could be a discrimination factor featuring specific cultivar or geographical origin. The study paves the way toward new quantification panels and scientific research concerning vegetable oils.

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

Lipids constituents from Gardenia aqualla Stapf & Hutch

Gardenia aqualla a plant of the Rubiaceae family is being used extensively in Africa, particularly in Cameroon as an herbal medicine. Therefore it is necessary to have knowledge of the constituents of the plant of our native species. Thus, the aim of the present study was to investigate chemical constituents of this herbal medicine. Nine compounds, including one alkane, n-Nonacosane (1), two aliphatic alcohols n-heptatriacontanol (2) and n-Docosanol(3), one fatty ester, Heptadecyl heptacosanoate (4), two sugars, D-mannitol (5) and D-mannitol acetate (6), and a mixture of three phytosterols, β-sitosterol (7), stigmasterol (8) and fucosterol (9), have been isolated and purified from the stem barks of Gardenia aqualla Stapf & Hutch. Their structures were elucidated using spectroscopic analyses, including 1D and 2D NMR and ESI-MS. The fatty acid ester, heptadecyl heptacosanoate (4) is reported here for the first time. All the isolated compounds were tested for their antimicrobial activities against four Gram negative bacteria (Salmonella Typhimurium ATCC6539, Pseudomonas aeruginosa ATCC9721, Escherichia coli, and S. Typhi) and four yeasts (Candida albicans ATCC9002, Candida parapsilosis ATCC22019, Candida krusei and C. albicans).

Amphiphilic dipyridinium-phosphotungstate as an efficient and recyclable catalyst for triphasic fatty ester epoxidation and oxidative cleavage with hydrogen peroxide

A novel amphiphilic dipyridinium peroxophosphotungstate ion pair achieved remarkable selectivity and recyclability towards epoxidation and oxidative cleavage of fatty acids and esters.