Olive Pomace Extract Contains Low Molecular Weight Peptides and Possesses ACE Inhibitory Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation of a Water-Soluble LMW Fraction from Olive Pomace Extract
2.2. Amino Acid Analysis and Native PAGE of Olive Pomace LMW Extract
2.3. Fractionation of Peptides by Size-Exclusion Chromatography
2.4. ACE Inhibitory Activity Determinations
2.5. Endogenous Peptides and Proteins Identified by Peaks DB and De Novo Sequencing in Olive Pomace
2.6. Predicted Activities of Olive Pomace Endogenous Peptides
3. Materials and Methods
3.1. Plant Material and Extraction of Olive Oil
3.2. Preparation of Olive Pomace Extract Containing Low-Molecular Weight Peptides
3.3. Analysis and Quantification of Amino Acids
3.4. Detection of Peptides and Antioxidant Activity of Olive Pomace LMW Peptides in Native Polyacrylamide Gels
3.5. Extraction of Polyphenols from Olive Pomace Extracts
3.6. Analysis of Minerals by Inductively Coupled Plasma-Optical Emission Spectrometry (ICP-OES)
3.7. Fractionation of Olive Pomace Peptides by Size-Exclusion Chromatography
3.8. Determination of Angiotensin-Converting Enzyme Inhibitory Activity
3.9. LC-Orbitrap MS/MS Analysis of Olive Pomace LMW Peptide Fraction
3.10. Peptide and Protein Identification by Database Search and De Novo Sequencing
3.11. Biological Activity Prediction of Identified Peptides from Olive Pomace Peptides
3.12. Determination of Total Nitrogen, Fat, Carbohydrates, and Polyphenols
3.13. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Sample | IC50 (µg prot/mL) |
---|---|
Olive pomace LMW fraction | 3.57 ± 0.22 |
F16 | 365.8 ± 32.3 |
F17 | 125.1 ± 33.1 |
F18 | 75.6 ± 6.9 |
F19 | 67.4 ± 14.5 |
F20 | 68.52 ± 7.49 |
No. | Peptide Sequence | −10lgP | N | m/z | RT | ppm | Area | Protein Source (BLAST) | Accession |
---|---|---|---|---|---|---|---|---|---|
1 | NSNALACCSA | 34.52 | 10 | 477.1920 | 51.20 | 7.1 | 3.16 × 107 | anthocyanidin 3-O-glucosyltransferase | OE9A062433P1 |
CAA2981081.1 | |||||||||
2 | GGDNGMNH | 31.98 | 8 | 401.1449 | 51.36 | −4.5 | 4.85 × 105 | phospholipase D gamma 1-like | OE9A085147P3 OE9A085147P2 |
CAA2951337.1 | |||||||||
3 | RSCQHRY | 30.05 | 7 | 475.2191 | 21.09 | 0.4 | ND | putative RING-H2 finger protein ATL21A | OE9A113191P1 |
XP_022855964.1 | |||||||||
4 | LPPDNSH | 29.26 | 7 | 390.1841 | 52.42 | 2.7 | 3.26 × 106 | Hypothetical predicted protein | OE9A032896P1 |
CAA2978878.1 | |||||||||
5 | SLIPCCSS | 27.21 | 8 | 809.3359 | 54.15 | −6.6 | 6.69 × 106 | casein kinase 1 HD16 | OE9A059381P2 OE9A059381P1 OE9A059381P3 |
CAA2934848.1 | |||||||||
6 | SGDPTM(+15.99)YE | 26.79 | 8 | 458.1616 | 50.95 | −11.8 | 2.68 × 105 | tryptophan aminotransferase-related 2 isoform X1 | OE9A048079P1 |
CAA2969551.1 | |||||||||
7 | IDHGCAKH | 25.50 | 8 | 440.7025 | 42.72 | −1.2 | 1.65 × 106 | anthocyanidin 3-O-glucosyltransferase | OE9A062433P1 |
CAA2981081.1 | |||||||||
8 | IPATDSQG | 25.47 | 8 | 394.6899 | 36.41 | 4.6 | 1.42 × 106 | auxin response factor 6 isoform X1 | OE9A083314P2 OE9A083314P3 OE9A083314P1 |
CAA2976018.1 | |||||||||
9 | MCTAAEM(+15.99)K | 25.21 | 8 | 450.6838 | 48.32 | 9.9 | 4.66 × 105 | white-brown complex homolog 30 | OE9A053685P3 |
CAA2969019.1 | |||||||||
10 | GGGPGGGLGGPS | 25.13 | 12 | 435.2055 | 45.44 | 3.6 | 3.10 × 106 | dihydrolipoyllysine-residue succinyl transferase component of 2-oxoglutarate de-hydrogenase | OE9A068558P1 |
CAA3014561.1 | |||||||||
11 | QANACHH | 25.10 | 7 | 390.6582 | 33.30 | −2.5 | 2.59 × 105 | DUF946 domain-containing DUF1162 domain-containing Chorein | OE9A008961P3 |
CAA2957578.1 | |||||||||
12 | NSCCVCMVR | 25.00 | 9 | 507.6946 | 42.64 | −4.6 | 1.31 × 107 | probable E3 ubiquitin-ligase LOG2 | OE9A009309P1 |
CAA3023827.1 |
No. | Peptide | ALC (%) | N | Z | m/z | RT | Area | ppm | Local Confidence (%) |
---|---|---|---|---|---|---|---|---|---|
1 | LFYHHH | 90 | 6 | 2 | 427.2079 | 30.18 | 1.96 × 106 | −2.2 | 88 85 88 95 88 96 |
2 | GDHSGPPR | 89 | 8 | 2 | 411.6919 | 31.88 | 5.36 × 106 | −10.6 | 56 92 97 97 94 97 95 90 |
3 | YCFHSAA | 89 | 7 | 2 | 399.6636 | 32.80 | 4.63 × 105 | −5.0 | 96 95 91 88 84 85 88 |
4 | YTM(+15.99)M(+15.99)LF | 89 | 6 | 2 | 419.1794 | 23.63 | 4.06 × 106 | −0.8 | 92 90 92 76 93 93 |
5 | AEFENFVAFVDK | 88 | 12 | 2 | 708.3472 | 48.76 | 1.88 × 106 | 2.2 | 40 72 98 99 95 96 93 95 99 98 96 82 |
6 | RCYHEE | 87 | 6 | 2 | 418.6729 | 49.92 | ND | 3.6 | 84 93 90 85 85 86 |
7 | YVM(+15.99)FFL | 87 | 6 | 2 | 418.2032 | 29.26 | 1.31 × 106 | −8.0 | 98 94 92 87 71 80 |
8 | FFTYAY | 87 | 6 | 2 | 406.1843 | 36.79 | 2.90 × 105 | −5.9 | 85 85 90 90 85 86 |
9 | YEM(+15.99)YPY | 87 | 6 | 2 | 441.1741 | 25.78 | 3.42 × 107 | 2.7 | 82 86 80 92 82 97 |
10 | LSVSAFNC | 86 | 8 | 2 | 420.7043 | 28.04 | 6.54 × 105 | 11.2 | 93 94 94 90 92 93 69 69 |
No. | Peptide Sequence | Predicted Activity | No. Seq. with Activity | A | B |
---|---|---|---|---|---|
1 | NSNALACCSA | ACE inhibitor | 1 | 0.1000 | 0.0003 |
Antioxidative | 1 | 0.1000 | |||
DPP III inhibitor | 1 | 0.1000 | |||
DPP IV inhibitor | 3 | 0.1000 | |||
Activating ubiquitin-mediated proteolysis | 1 | 0.1000 | 0.0001 | ||
2 | GGDNGMNH | ACE inhibitor | 4 | 0.5 | 0.0001 |
DPP IV inhibitor | 5 | 0.6250 | 0.0018 | ||
3 | RSCQHRY | ACE inhibitor | 1 | 0.1429 | 0.0136 |
Antioxidative | 1 | 0.1429 | 9.72 × 10−6 | ||
DPP IV inhibitor | 2 | 0.2857 | 8.47 × 10−5 | ||
4 | LPPDNSH | ACE inhibitor | 3 | 0.4286 | 0.0161 |
alpha-glucosidase inhibitor | 1 | 0.1429 | |||
DPP IV inhibitor | 4 | 0.5714 | 0.0018 | ||
5 | SLIPCCSS | ACE inhibitor (IP) | 1 | 0.125 | 0.001 |
DPP IV inhibitor | 3 | 0.375 | 0.0003 | ||
Regulator of phosphoglycerate kinase activity | 1 | 0.125 | |||
Glucose uptake stimulating peptide | 1 | 0.125 | |||
6 | SGDPTM(+15.99)YE | ACE inhibitor | 4 | 0.2500 | 0.0001 |
DPP IV inhibitor | 4 | 0.2500 | |||
7 | IDHGCAKH | ACE inhibitor | 1 | 0.125 | 1.98 × 10−5 |
DPP IV inhibitor | 1 | 0.125 | |||
antioxidative | 1 | 0.125 | |||
8 | IPATDSQG | ACE inhibitor | 3 | 0.375 | 0.0019 |
DPP IV inhibitor | 6 | 0.75 | 0.0029 | ||
9 | MCTAAEM(+15.99)K | ACE inhibitor | 1 | 0.0625 | 0.0001 |
hypotensive | 1 | 0.0625 | |||
DPP IV inhibitor | 3 | 0.1875 | 6.64 × 10−6 | ||
10 | GGGPGGGLGGPS | ACE inhibitor | 5 | 0.8333 | 0.0008 |
DPP IV inhibitor | 5 | 0.8333 | 4.91 × 10−5 | ||
PAM inhibitor | 1 | 0.0833 | |||
peptide regulating the stomach mucosal membrane activity | 3 | 0.3333 | |||
Antithrombotic peptide | 3 | 0.3333 | |||
Prolyl endopeptidase inhibitor (antiamnestic) | 3 | 0.3333 | |||
11 | QANACHH | antioxidative | 1 | 0.1429 | 3.11 × 10−2 |
DPP IV inhibitor | 3 | 0.4286 | |||
12 | NSCCVCMVR | ACE inhibitor | 1 | 0.1111 | 0.0021 |
DPP IV inhibitor | 2 | 0.2222 | 0.0001 |
No. | De Novo Peptide | Predicted Activity | No. Seq. with Activity | A | B |
---|---|---|---|---|---|
1 | LFYHHH | ACE inhibitor | 3 | 0.5 | 0.0396 |
Antioxidative | 3 | 0.667 | |||
DPP III inhibitor | 2 | 0.1667 | |||
DPP IV inhibitor | 1 | 0.5000 | |||
2 | GDHSGPPR | ACE inhibitor | 7 | 0.875 | 0.0380 |
Antioxidative | 1 | 0.1250 | |||
DPP III inhibitor | 1 | 0.1250 | |||
DPP IV inhibitor | 1 | 0.375 | |||
antiamnestic | 1 | 0.1250 | |||
antithrombotic | 1 | 0.1250 | |||
regulating | 1 | 0.1250 | |||
alpha-glucosidase inhibitor | 1 | 0.1250 | |||
3 | YCFHSAA | ACE inhibitor | 3 | 0.2857 | 0.0731 |
hypotensive | 1 | 0.2857 | 1.519 × 10−5 | ||
DPP IV inhibitor | 2 | 0.1429 | |||
4 | YTM(+15.99)M(+15.99)LF | ACE inhibitor | 2 | 0.3333 | 0.0008 |
Antioxidative | 1 | 0.1667 | 0.0003 | ||
DPP IV inhibitor | 4 | 0.6667 | 0.0036 | ||
5 | AEFENFVAFVDK | ACE inhibitor | 4 | 0.3333 | 0.0046 |
DPP IV inhibitor | 5 | 0.0833 | 0.0005 | ||
CaMPDE inhibitor | 1 | 0.4167 | |||
hypolipidemic | 2 | 0.0833 | |||
renin inhibitor | 1 | 0.0833 | |||
6 | RCYHEE | ACE inhibitor | 1 | 0.1667 | 0.0325 |
DPP III inhibitor | 1 | 0.1667 | |||
DPP IV inhibitor | 1 | 0.3333 | |||
stimulating | 1 | 0.1667 | |||
7 | YVM(+15.99)FFL | ACE inhibitor | 5 | 0.8333 | 0.0113 |
DPP III inhibitor | 5 | 0.1667 | |||
DPP IV inhibitor | 1 | 0.8333 | 0.0006 | ||
8 | FFTYAY | ACE inhibitor | 4 | 0.5000 | 0.0119 |
Antioxidative | 4 | 0.6667 | |||
DPP IV inhibitor | 4 | 0.6667 | 0.0002 | ||
renin inhibitor | 2 | 0.333 | |||
9 | YEM(+15.99)YPY | ACE inhibitor | 3 | 0.5000 | 0.0014 |
Antioxidative | 1 | 0.1667 | |||
DPP IV inhibitor | 5 | 0.8333 | 0.0007 | ||
anti inflammatory | 1 | 0.1667 | |||
alpha-glucosidase inhibitor | 2 | 0.3333 | 0.0001 | ||
10 | LSVSAFNC | ACE inhibitor | 1 | 0.1250 | 0.0007 |
DPP IV inhibitor | 4 | 0.5000 |
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López-Huertas, E.; Rubí-Villegas, J.; Sánchez-Moreno, L.; Nieto, R. Olive Pomace Extract Contains Low Molecular Weight Peptides and Possesses ACE Inhibitory Activity. Int. J. Mol. Sci. 2024, 25, 3962. https://doi.org/10.3390/ijms25073962
López-Huertas E, Rubí-Villegas J, Sánchez-Moreno L, Nieto R. Olive Pomace Extract Contains Low Molecular Weight Peptides and Possesses ACE Inhibitory Activity. International Journal of Molecular Sciences. 2024; 25(7):3962. https://doi.org/10.3390/ijms25073962
Chicago/Turabian StyleLópez-Huertas, Eduardo, Jose Rubí-Villegas, Lourdes Sánchez-Moreno, and Rosa Nieto. 2024. "Olive Pomace Extract Contains Low Molecular Weight Peptides and Possesses ACE Inhibitory Activity" International Journal of Molecular Sciences 25, no. 7: 3962. https://doi.org/10.3390/ijms25073962