Enzyme kinetics, molecular docking, and in silico characterization of canary seed (Phalaris canariensis L.) peptides with ACE and pancreatic lipase inhibitory activity

Urbizo-Reyes, Uriel; Liceaga, Andrea M.; Reddivari, Lavanya; Kim, Kee‐Hong; Anderson, Joseph M.

doi:10.1016/j.jff.2021.104892

Cited by 45 publications

(68 citation statements)

References 61 publications

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“…Results reported by Chae and collaborators and those obtained in this study are not comparable, because very different methodologies were used [ 34 ]. On the other hand, the results obtained for 4 agree with those reported by Adnyana and collaborators, since the same method of quantifying the enzymatic activity was used [ 17 ]. A preliminary structure–activity analysis indicates that compounds having isoprenyl chains at positions 2 and 8 of the xanthone nucleus ( 4 , 5 , 6 and 11 ) have the lowest IC 50 values, suggesting that the presence and location of these substituents are important for PL inhibition.…”

Section: Resultssupporting

confidence: 87%

“…The results indicated that EE and the DCM fraction are the most promising to inhibit the PL, AA and AG enzymes. This is the first report of inhibitory activity of EE on AG, while its activity had already been reported on PL (IC 50 26.50 ± 1.15 µg/mL) and AA (IC 50 105.36 ± 2.73 µg/mL) [ 17 ]. The reported results are different from those found in this investigation, observing that EE is more active on PL and less active on AA.…”

Section: Resultsmentioning

confidence: 86%

“…This study constitutes the first report of inhibitory activity against PL for compounds 6 , 9 and 11 . In previous studies, activity against PL has been reported for 1 (IC 50 = 12 µM), 2 (IC 50 = 50 µM), 3 (IC 50 = 12 µM), 4 (IC 50 = 5 µM; IC 50 = 47.3 µM), and 5 (IC 50 = 10 µM) [ 17 , 37 ]. Results reported by Chae and collaborators and those obtained in this study are not comparable, because very different methodologies were used [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…Antiobesity medications generally involve three mechanisms: enhancement of energy expenditure, appetite suppression and inhibition of gastrointestinal enzymes involved in digestion, absorption and metabolism of carbohydrates and fats [ 9 , 10 , 15 , 16 ]. Since pancreatic lipase plays an important role in fat absorption, its inhibition has also been of great interest in drug development [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

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Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

et al. 2022

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Digestive enzymes such α-amylase (AA), α-glucosidase (AG) and pancreatic lipase (PL), play an important role in the metabolism of carbohydrates and lipids, being attractive therapeutic targets for the treatment of type 2 diabetes and obesity. Garcinia mangostana is an interesting species because there have been identified xanthones with the potential to inhibit these enzymes. In this study, the multitarget inhibitory potential of xanthones from G. mangostana against AA, AG and PL was assessed. The methodology included the isolation and identification of bioactive xanthones, the synthesis of some derivatives and a molecular docking study. The chemical study allowed the isolation of five xanthones (1–5). Six derivatives (6–11) were synthesized from the major compound, highlighting the proposal of a new solvent-free methodology with microwave irradiation for obtaining aromatic compounds with tetrahydropyran cycle. Compounds with multitarget activity correspond to 2, 4, 5, 6 and 9, highlighting 6 with IC50 values of 33.3 µM on AA, 69.2 µM on AG and 164.4 µM on PL. Enzymatic kinetics and molecular docking studies showed that the bioactive xanthones are mainly competitive inhibitors on AA, mixed inhibitors on AG and non-competitive inhibitors on PL. The molecular coupling study established that the presence of methoxy, hydroxyl and carbonyl groups are important in the activity and interaction of polyfunctional xanthones, highlighting their importance depending on the mode of inhibition.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

et al. 2022

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“…Among these peptides, ACEi peptides represent a promising alternative to synthetic drugs to control hypertension [ 11 , 12 ]. For instance, canary seed peptides (CSP) have great potential as anti-hypertensive and anti-obesity agents due to their inhibition activity on ACE and pancreatic lipase, and their non-competitive inhibitory activity was due to their destabilization of the transition state and Zn(II) coordination in ACE [ 13 ]. Noncompetitive ACEi peptides of TYLPVH (IC 50 1.37 μM) and GRVSNCAA (IC 50 57.93 μM) from Ruditapes philippinarum can lower systolic blood pressure in the single blood pressure test and promote NO secretion and reduced ET-1 production [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation, Identification, Molecular Docking Study and Protective Function on HUVECs of Novel ACE Inhibitory Peptides from Protein Hydrolysate of Skipjack Tuna Muscle

et al. 2022

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To prepare bioactive peptides with high angiotensin-I-converting enzyme (ACE)-inhibitory (ACEi) activity, Alcalase was selected from five kinds of protease for hydrolyzing Skipjack tuna (Katsuwonus pelamis) muscle, and its best hydrolysis conditions were optimized using single factor and response surface experiments. Then, the high ACEi protein hydrolysate (TMPH) of skipjack tuna muscle was prepared using Alcalase under the optimum conditions of enzyme dose 2.3%, enzymolysis temperature 56.2 °C, and pH 9.4, and its ACEi activity reached 72.71% at 1.0 mg/mL. Subsequently, six novel ACEi peptides were prepared from TMPH using ultrafiltration and chromatography methods and were identified as Ser-Pro (SP), Val-Asp-Arg-Tyr-Phe (VDRYF), Val-His-Gly-Val-Val (VHGVV), Tyr-Glu (YE), Phe-Glu-Met (FEM), and Phe-Trp-Arg-Val (FWRV), with molecular weights of 202.3, 698.9, 509.7, 310.4, 425.6, and 606.8 Da, respectively. SP and VDRYF displayed noticeable ACEi activity, with IC50 values of 0.06 ± 0.01 and 0.28 ± 0.03 mg/mL, respectively. Molecular docking analysis illustrated that the high ACEi activity of SP and VDRYF was attributed to effective interaction with the active sites/pockets of ACE by hydrogen bonding, electrostatic force, and hydrophobic interaction. Furthermore, SP and VDRYF could significantly up-regulate nitric oxide (NO) production and down-regulate endothelin-1 (ET-1) secretion in HUVECs after 24 h treatment, but also abolish the negative effect of 0.5 μM norepinephrine (NE) on the generation of NO and ET-1. Therefore, ACEi peptides derived from skipjack tuna (K. pelamis) muscle, especially SP and VDRYF, are beneficial components for functional food against hypertension and cardiovascular diseases.

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Recent trends in metal‐organic frameworks mediated lipase immobilization: A state‐of‐the‐art review

Patil,

Dong,

Usman

et al. 2023

Food Safety and Health

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Immobilized lipase is a powerful biocatalytic system with numerous applications in industries, particularly in the energy, pharmaceutical, cosmetic, and food industries. Reusability, simple recovery, and high chemical and thermal stability make it an attractive alternative to traditional chemical catalysts in industrial applications. Novel methods and support materials for immobilizing lipases have recently attracted much attention. Metal‐organic frameworks (MOFs) are a promising class of materials for enzyme immobilization carriers due to their appealing features, including a high specific surface area, high specific porosity, a stable framework structure, and a wide variety of functional sites. Due to the protection provided to enzymes by MOFs, several reported MOFs‐lipase composites display exceptional catalytic characteristics relative to free lipases. This includes increased enzyme efficiency, stability, selectivity, and recyclability. Herein, we summarize an updated review of the most recent advances in MOFs immobilizing lipases. This review sheds light on the numerous aspects of lipase‐MOF immobilization, with special emphasis on different techniques of designing lipase‐MOF platforms and the advantages of lipase‐MOF composites. Subsequently, molecular simulation approaches in lipase‐MOF immobilization are briefly introduced. Moreover, practical applications of MOFs‐lipase composites have been outlined. Finally, potential limitations and future directions for MOFs‐lipase immobilization research are highlighted.

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Enzyme kinetics, molecular docking, and in silico characterization of canary seed (Phalaris canariensis L.) peptides with ACE and pancreatic lipase inhibitory activity

Cited by 45 publications

References 61 publications

Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

Preparation, Identification, Molecular Docking Study and Protective Function on HUVECs of Novel ACE Inhibitory Peptides from Protein Hydrolysate of Skipjack Tuna Muscle

Recent trends in metal‐organic frameworks mediated lipase immobilization: A state‐of‐the‐art review

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