Orbitides from flaxseed (Linum usitatissimum L.): A comprehensive review

Shim, Youn Young; Song, Ziliang; Jadhav, Pramodkumar D.; Reaney, Martin J. T.

doi:10.1016/j.tifs.2019.09.007

Cited by 33 publications

(43 citation statements)

References 60 publications

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“…CLA belongs to the plant Orbitides family and was recently more closely characterized [ 2 , 3 ]. Although flaxseed extracts contain a variety of pharmacologically active compounds [ 2 , 3 ], the biological properties of CLA and its analogs have been investigated most extensively. In these studies, the native peptide was subjected to several modifications in order to improve its immunosuppressive efficacy and solubility, and to identify its key sequences in the structure.…”

Section: Introductionmentioning

confidence: 99%

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Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Zimecki

Kaczmarek

2021

Molecules

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The consequences of manipulations in structure and amino acid composition of native cyclolinopeptide A (CLA) from linen seeds, and its linear precursor on their biological activities and mechanisms of action, are reviewed. The modifications included truncation of the peptide chain, replacement of amino acid residues with proteinogenic or non-proteinogenic ones, modifications of peptide bond, and others. The studies revealed changes in the immunosuppressive potency of these analogs investigated in a number of in vitro and in vivo experimental models, predominantly in rodents, as well as differences in their postulated mechanism of action. The modified peptides were compared with cyclosporine A and parent CLA. Some of the synthesized and investigated peptides show potential therapeutic usefulness.

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Section: Introductionmentioning

confidence: 99%

“…Figure 2.The structure of the cyclic tetrapeptide, cyclo-(L-Pro-L-Pro-L-β 3 hPhe-L-Phe-). (3S,9S,13S,16S)-9,13-dibenzyl-1,7,10,14-tetraazatricyclo[14.3.0.03,7 ]nonadecane-2,8,11,15-tetrone (IU-PAC name).…”

mentioning

confidence: 99%

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Zimecki

Kaczmarek

2021

Molecules

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“…Though they are commonly consumed and used in ethnobotanical remedies, little is known about the Cys-rich AMPs produced by each species. Previous work in flax has focused on small, cysteine-free, cyclic peptides called orbitides, but largely ignored Cys-rich AMPs [ 23 ]. Sesame is known to produce an α-hairpinin as well as a 5.8 kDa unsequenced antibacterial peptide [ 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometric Identification of Antimicrobial Peptides from Medicinal Seeds

Moyer¹,

Brechbill²,

Hicks³

2021

Molecules

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Traditional medicinal plants contain a variety of bioactive natural products including cysteine-rich (Cys-rich) antimicrobial peptides (AMPs). Cys-rich AMPs are often crosslinked by multiple disulfide bonds which increase their resistance to chemical and enzymatic degradation. However, this class of molecules is relatively underexplored. Herein, in silico analysis predicted 80–100 Cys-rich AMPs per species from three edible traditional medicinal plants: Linum usitatissimum (flax), Trifolium pratense (red clover), and Sesamum indicum (sesame). Bottom-up proteomic analysis of seed peptide extracts revealed direct evidence for the translation of 3–10 Cys-rich AMPs per species, including lipid transfer proteins, defensins, α-hairpinins, and snakins. Negative activity revealed by antibacterial screening highlights the importance of employing a multi-pronged approach for AMP discovery. Further, this study demonstrates that flax, red clover, and sesame are promising sources for further AMP discovery and characterization.

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“…A cyclic nonapeptide, Cyclolinopeptide A (CLA) with a sequence cyclo(Leu 1 -Ile 2 -Ile 3 -Leu 4 -Val 5 -Pro 6 -Pro 7 -Phe 8 -Phe 9 -) was isolated from linen seeds oil [1]. CLA belongs to the plant Orbitides family and was recently more closely characterized [2,3]. Although flaxseed extracts contain a variety of pharmacologically active compounds [2,3], the biological properties of CLA and its analogs have been investigated by a narrow group of researchers.…”

Section: Introductionmentioning

confidence: 99%

“…CLA belongs to the plant Orbitides family and was recently more closely characterized [2,3]. Although flaxseed extracts contain a variety of pharmacologically active compounds [2,3], the biological properties of CLA and its analogs have been investigated by a narrow group of researchers. In these studies, the native peptide was subjected to several modifications in order to improve its immunosuppressive efficacy and solubility, and to identify its key sequences in the structure.…”

Section: Introductionmentioning

confidence: 99%

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and its Analogs in Animal Experimental Models

Zimecki¹,

Kaczmarek²

2021

Preprint

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The consequences of manipulations in structure and amino acid composition of native cyclolinopeptide A (CLA) from linen seeds and its linear precursor on their biological activities and mechanisms of action are reviewed. The modifications included truncation of the peptide chain, replacement of amino acid residues with proteinogenic or non-proteinogenic ones, modifications of peptide bond, and others. The studies revealed changes in the immunosuppressive potency of these analogs investigated in a number of in vitro and in vivo experimental models, predominantly in rodents, as well as differences in their postulated mechanism of action. The modified peptides were compared with cyclosporine A and parent CLA. Some of the synthesized and investigated peptides show potential therapeutic usefulness.

show abstract

Orbitides from flaxseed (Linum usitatissimum L.): A comprehensive review

Cited by 33 publications

References 60 publications

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and Its Analogs in Animal Experimental Models

Mass Spectrometric Identification of Antimicrobial Peptides from Medicinal Seeds

Effects of Modifications on the Immunosuppressive Properties of Cyclolinopeptide A and its Analogs in Animal Experimental Models

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