A practical and fast isolation of 12 cyclolinopeptides (linusorbs) from flaxseed oil via preparative HPLC with phenyl-hexyl column

Liu, Xue; Cai, Zi-zhe; Lee, Wan Jun; Lu, Xuanxuan; Reaney, Martin J. T.; Zhang, Jianping; Li, Ying; Zhang, Ning; Wang, Yong

doi:10.1016/j.foodchem.2021.129318

Cited by 13 publications

(7 citation statements)

References 23 publications

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“…In total, 15 cyclic peptides could be identified with elution orders F, G, K, C, T, I, D, P, E, N, B, O, A, L, and M. Aladedunye et al ( 24 ) identified 14 CLPs in flaxseed oil, F, G, C, E, I, D, H, N, B, L, A, J, M, and K, using a Kinetex Column and HPLC Exactive Orbitrap MS. Lao and his group identified 15 CLPs, F, G, C, E, T, H, D, I, P, B, A, L, N, O, and M, using a Kinetex TM phenyl-hexyl column and MALDI quadrupole/TOF prototype mass spectrometry ( 17 ). In 2021, in the CLP isolation experiment, 15 CLPs were identified using a Kinetex TM phenyl hexyl column with a TripleTOF 5600 mass analyzer ( 32 ). Other groups identified up to 7 CLPs using Hybrid Quadrupole-TOF MS/MS with monolithic and microparticulate columns ( 29 ).…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, it is important to mention that some other groups managed to separate 11 and 12 CLPs using RP-HPLC. However, applying time-consuming and expensive approaches for extraction and elution, where gradients of acetonitrile-water were used, with flows of 2 and 16 ml/min ( 30 , 32 ). A potential limitation of using methanol as the eluent would be an occasional drift in the baseline, which was also reported in other publications ( 24 ).…”

Section: Resultsmentioning

confidence: 99%

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Identification and Characterization of the Stability of Hydrophobic Cyclolinopeptides From Flaxseed Oil

2022

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Flaxseed (linseed) is a cultivar of the spring flowering annual plant flax (Linum usitatissimum) from the Linaceae family. Derivatives of this plant are widely used as food and as health products. In recent years, cyclic peptides isolated from flaxseed and flaxseed oil, better known as cyclolinopeptides (CLPs), have attracted the attention of the scientific community due to their roles in the inhibition of osteoclast differentiation or their antimalarial, immunosuppressive, and antitumor activities, as well as their prospects in nanotechnology and in the biomedical sector. This study describes the detection, identification, and measurement of CLPs in samples obtained from nine different flaxseed oil manufacturers. For the first time, Q Exactive Hybrid Quadrupole-Orbitrap Mass Spectrometer was used for CLP identification together with RP-HPLC. The routine analyses were performed using RP chromatography, measuring the absorption spectra and fluorescence detection for identifying tryptophan-containing peptides using the native fluorescence of tryptophan. In addition, existing protocols used for CLP extraction were optimized and improved in a fast and cost-efficient way. For the first time, 12 CLPs were separated using methanol/water as the eluent with RP-HPLC. Finally, the stability and degradation of individual CLPs in the respective flaxseed oil were examined over a period of 60 days at different temperatures. The higher temperature was chosen since this might reflect the cooking practices, as flaxseed oil is not used for high-temperature cooking. Using HPLC–MS, 15 CLPs were identified in total in the different flaxseed oils. The characterization of the peptides via HPLC–MS highlighted two types of CLP profiles with a substantial variation in the concentration and composition of CLPs per manufacturer, probably related to the plant cultivar. Among the observed CLPs, CLP-O, CLP-N, and CLP-B were the least stable, while CLP-C and CLP-A were the most stable peptides. However, it is important to highlight the gradual degradation of most of the examined CLPs over time, even at room temperature.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Identification and Characterization of the Stability of Hydrophobic Cyclolinopeptides From Flaxseed Oil

2022

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“…The extract was combined and removed the solvent at 50°C by a rotary evaporator. Column chromatography was used to purify the extract, and then, the purified products were separated into reduced LOs and oxidized LOs following the previous method with modifications by preparative‐HPLC‐PDA (Reveleris® Prep Purification System; Grace Inc., Columbia, MD) and equipped with VisionHT C18 HT column (250 × 22 mm, 10 μm; Grace Inc., Columbia, MD) (19). In detail, acetonitrile and ultrapure water were used as mobile phase for gradient elution, initial acetonitrile ratio of 40%, and increased to 80% within 30 min, then increased to 100% within 0.5 min and maintained 3 min, with the flow rate of 16 mL min −1 , loaded sample of 5 mL with concentration of 20 mg mL −1 .…”

Section: Methodsmentioning

confidence: 99%

Protective Effect of Orbitides from Linseed (Linum usitatissimum L.) against Ultraviolet B‐induced Photoaging in Zebrafish

Cheng

Wang

Guo

et al. 2022

Photochem & Photobiology

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Excessive ultraviolet (UV) exposure is the primary environmental factor that contributes to skin aging. Orbitides have been considered as important functional components in linseed, and they are complex and multiple. In this study, linseed orbitides (LOs) were divided into oxidized linseed orbitides (OLOs) and reduced linseed orbitides (RLOs) and used to investigate protection against ultraviolet B‐induced photoaging in zebrafish. First, the results of the zebrafish embryo acute toxicity test showed that the OLOs had obvious embryo toxicity compared with RLOs. And RLOs had better effect in ultraviolet B‐treated zebrafish, which may significantly reduce the reactive oxygen species levels and inhibit the degradation of collagen. Besides, we also found that RLOs could effectively inhibit the oxidation of proteins and lipids and regulate the activity of antioxidant enzymes. Furthermore, neutrophil recruitment to the dorsal and caudal fin regions was observed in UVB‐treated zebrafish, and RLOs effectively alleviated this migration. In conclusion, RLOs have strong photoprotective effects and potential to be used as antiphotoaging ingredients.

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“…[17][18][19][20] Among them, HPLC has the advantages of fast separation, high sensitivity, strong reproducibility and wide application elds, playing an increasingly important role in the detection and separation of racemic drugs. 21,22 However, the lack of a universal chiral selector translates into the need to design and fabricate novel chiral stationary phases (CSPs) in HPLC.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation in high performance liquid chromatography: preparation and evaluation of a vancomycin-based chiral stationary phase via surface-initiated atom transfer radical polymerization

et al. 2022

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A practical and fast isolation of 12 cyclolinopeptides (linusorbs) from flaxseed oil via preparative HPLC with phenyl-hexyl column

Cited by 13 publications

References 23 publications

Identification and Characterization of the Stability of Hydrophobic Cyclolinopeptides From Flaxseed Oil

Identification and Characterization of the Stability of Hydrophobic Cyclolinopeptides From Flaxseed Oil

Protective Effect of Orbitides from Linseed (Linum usitatissimum L.) against Ultraviolet B‐induced Photoaging in Zebrafish

Enantioseparation in high performance liquid chromatography: preparation and evaluation of a vancomycin-based chiral stationary phase via surface-initiated atom transfer radical polymerization

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