Determination and Comparison of Seed Oil Triacylglycerol Composition of Various Soybeans (Glycine max (L.)) Using  1H-NMR Spectroscopy

Kim, Won Woo; Rho, Ho Sik; Hong, Yong Deog; Yeom, Myung Hun; Shin, Song Seok; Yi, Jun Gon; Lee, Min-Seuk; Park, Hye Yoon; Cho, Dong Ha

doi:10.3390/molecules181114448

Cited by 8 publications

(7 citation statements)

References 16 publications

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“…Fatty‐acyl chains in hepatic triglycerides may originate from dietary lipids or be synthesized de novo . In our experiments, dietary fat derived from soybean oil that is composed mainly of triglycerides from unsaturated 18‐carbon fatty acids with up to a 20% contribution from saturated 16‐ and 18‐carbon fatty acids , in agreement with the fatty acid composition estimated in the soybean oil‐in‐water emulsion (Table ). On the other hand, de novo lipogenesis culminates with the synthesis of 16‐carbon saturated palmitoyl‐CoA, which can be further elongated or desaturated by specific hepatic enzymes.…”

Section: Discussionsupporting

confidence: 87%

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo

2015

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Alterations in the hepatic lipid content (HLC) and fatty acid composition are associated with disruptions in whole body metabolism, both in humans and in rodent models, and can be non-invasively assessed by 1 H-MRS in vivo. We used 1 H-MRS to characterize the hepatic fatty-acyl chains of healthy mice and to follow changes caused by streptozotocin (STZ) injection. Using STEAM at 14.1 T with an ultra-short T E of 2.8 ms, confounding effects from T 2 relaxation and J-coupling were avoided, allowing for accurate estimations of the contribution of unsaturated (UFA), saturated (SFA), mono-unsaturated (MUFA) and poly-unsaturated (PUFA) fatty-acyl chains, number of double bonds, PU bonds and mean chain length. Compared with in vivo 1 H-MRS, high resolution NMR performed in vitro in hepatic lipid extracts reported longer fatty-acyl chains (18 versus 15 carbons) with a lower contribution from UFA (61 ± 1% versus 80 ± 5%) but a higher number of PU bonds per UFA (1.39 ± 0.03 versus 0.58 ± 0.08), driven by the presence of membrane species in the extracts. STZ injection caused a decrease of HLC (from 1.7 ± 0.3% to 0.7 ± 0.1%), an increase in the contribution of SFA (from 21 ± 2% to 45 ± 6%) and a reduction of the mean length (from 15 to 13 carbons) of cytosolic fatty-acyl chains. In addition, SFAs were also likely to have increased in membrane lipids of STZ-induced diabetic mice, along with a decrease of the mean chain length. These studies show the applicability of 1 H-MRS in vivo to monitor changes in the composition of the hepatic fatty-acyl chains in mice even when they exhibit reduced HLC, pointing to the value of this methodology to evaluate lipid-lowering interventions in the scope of metabolic disorders.

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Section: Discussionsupporting

confidence: 87%

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo

2015

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“…The structural characterization of these oils by 1D and 2D NMR spectroscopy is also well known. ,,,− ,− , Overall, the assignments of 1 H chemical shifts (Figure ) for the molecular structures of unmodified SBO and SBO-E100 were in excellent agreement with previous reports, ,− and 1 H– 1 H COSY-DQF provided further confirmation of the connectivity between different functional groups within the molecular structures (Figure S7).…”

Section: Resultssupporting

confidence: 85%

“…49−51 The percentages of these acyl groups are slightly different depending on the variety of the soybean crop as well as the region and conditions of production. 51 The double bonds on the latter three acyl groups are the reactive groups in an epoxidation reaction (Figure 1). The experimental protocol for epoxidation of vegetable oils (including SBO, palm oil, sunflower seed oil, etc.)…”

Section: Resultsmentioning

confidence: 99%

“…SBO is a triglyceride whose three fatty acid chains are a mixture of saturated, linolenic, linoleic, and oleic acyl groups (Figure ). − The percentages of these acyl groups are slightly different depending on the variety of the soybean crop as well as the region and conditions of production . The double bonds on the latter three acyl groups are the reactive groups in an epoxidation reaction (Figure ).…”

Section: Resultsmentioning

confidence: 99%

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Semiquantitative Solid-State NMR Study of the Adsorption of Soybean Oils on Silica and Its Significance for Rubber Processing

et al. 2021

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Soybean oil (SBO) is a renewable material used as an alternative to conventional petroleum-derived oils in the processing of rubber composites. Upon chemical modifications, such as epoxidation, its performance in the processing of rubber can be significantly improved, as indicated by a considerable reduction of the mixing energy. Although it has been hypothesized that hydrogen bonding between functional groups (e.g., epoxy) of SBOs and silanols present on the silica surface plays a key role, there is still a lack of direct evidence supporting this hypothesis. In this work, it is demonstrated that there is an overall correlation between the epoxy concentration of SBOs and the mixing energy, consistent with the long-held hypothesis. In particular, a correlation between the SBO–silica adsorption affinity and the degree of epoxidation is revealed by a set of surface-selective solid-state nuclear magnetic resonance (ssNMR) experiments. In addition, the surface-selective ssNMR technique demonstrated in this work could also be used to evaluate the adsorption affinity of other oils and/or additives more broadly.

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“…Sunflower oil showed a high amount of oleic acid, which is in accordance with the literature for a high-oleic sunflower oil [ 21 ]. Canola [ 22 ] and soybean oil [ 23 ] also showed a representative fatty acid profile [ 24 ] ( Table 2 ).…”

Section: Resultsmentioning

confidence: 99%

Contribution of the Ratio of Tocopherol Homologs to the Oxidative Stability of Commercial Vegetable Oils

et al. 2018

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The antioxidant activity of tocopherols in vegetable oils was shown to chiefly depend on the amount and the tocopherol homolog present. However, the most effective ratio of tocopherol homologs with regard to the antioxidant capacity has not been elucidated so far. The present study analyzed the effect of different tocopherol concentrations, homologs and ratios of homologs on markers of lipid oxidation in the most commonly consumed vegetable oils (canola, sunflower, soybean oil) stored in a 12 h light/dark cycle at 22 ± 2 °C for 56 days under retail/household conditions. After 56 days of storage, the α-tocopherol-rich canola and sunflower oil showed the strongest rise in lipid peroxides, yielding 25.1 ± 0.03 meq O2/kg (+25.3-fold) and 24.7 ± 0.05 meq O2/kg (+25.0-fold), respectively. ESR experiments, excluding effects of the oils’ matrices and other minor constituents, confirmed that a food representative tocopherol ratio of (γ + δ)/α = 4.77, as represented in soybean oil, led to a more pronounced delay of lipid oxidation than a lower ratio in canola (1.39) and sunflower oil (0.06). An optimum (γ + δ)/α -tocopherol ratio contributing to the oxidative quality of vegetable oils extending their shelf life has to be investigated.

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Determination and Comparison of Seed Oil Triacylglycerol Composition of Various Soybeans (Glycine max (L.)) Using 1H-NMR Spectroscopy

Cited by 8 publications

References 16 publications

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo

Semiquantitative Solid-State NMR Study of the Adsorption of Soybean Oils on Silica and Its Significance for Rubber Processing

Contribution of the Ratio of Tocopherol Homologs to the Oxidative Stability of Commercial Vegetable Oils

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Determination and Comparison of Seed Oil Triacylglycerol Composition of Various Soybeans (Glycine max (L.)) Using 1H-NMR Spectroscopy

Cited by 8 publications

References 16 publications

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time 1H‐MRS at 14.1 T in vivo

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time 1H‐MRS at 14.1 T in vivo

Semiquantitative Solid-State NMR Study of the Adsorption of Soybean Oils on Silica and Its Significance for Rubber Processing

Contribution of the Ratio of Tocopherol Homologs to the Oxidative Stability of Commercial Vegetable Oils

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Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo

Characterization of hepatic fatty acids in mice with reduced liver fat by ultra‐short echo time ¹H‐MRS at 14.1 T in vivo