PTP1B inhibitory activity and molecular docking analysis of stilbene derivatives from the rhizomes of Rheum undulatum L.

Ha, Manh Tuan; Park, Dong Hwa; Shrestha, Srijan; Kim, Minji; Kim, Jeong Ah; Woo, Mi Hee; Choi, Jae Sue; Min, Byung Sun

doi:10.1016/j.fitote.2018.10.020

Cited by 27 publications

(17 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The strongest H-bond interaction, however, was observed between the nitrogen group of Gly183 and the hydroxyl group in C-9 (ring B) of 1, with a bond distance of 2.86 Å. In addition, 1 also displayed hydrophobic interactions with some reported catalytic residues of PTP1B, such as Tyr46, Trp179, and Gln266 [23,24], which further stabilized the enzyme-inhibitor interaction (▶ Fig. 6, Table 4).…”

Section: Resultsmentioning

confidence: 99%

“…Many studies have indicated that the binding of ligand with residues in the α3 and α7 helices of PTP1B could lead to allosteric inhibition of enzyme activity [8,[23][24][25]. Leu192, Asn193, Phe196, Phe280 residues were frequently reported as the interacting residues for some PTP1B allosteric inhibitors [23][24][25]. From our docking results, the enzyme-inhibitor complexes of all tested compounds at the allosteric site of PTP1B exhibited high binding affinity (− 4.54, − 5.96, − 4.66, − 5.14, and − 5.21 kcal/mol, respectively) (▶ Table 4).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Unusual Prenylated Stilbene Derivatives with PTP1B Inhibitory Activity from Artocarpus styracifolius

Zhang

et al. 2019

Planta Med

View full text Add to dashboard Cite

In an effort to identify agents from natural products that inhibit protein tyrosine phosphatase 1B (PTP1B), 5 new prenylated stilbenes, (±)-styrastilbene A (1), styrastilbene B (2), and (±)-styrastilbenes C – E (3, 4, and 7), along with 4 known structurally related compounds (5, 6, 8, and 9), were isolated from the roots of Artocarpus styracifolius. Their structures were elucidated by spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), ultraviolet (UV), and infrared (IR). Based on these isolates, a new plausible biosynthetic pathway for the unusual stilbene derivatives 3–8 with a tetracyclic ring system is proposed. Among these compounds, 1–3, 8, and 9 displayed significant PTP1B inhibitory effects with IC50 values ranging from 2.40 (95% confidence interval [CI]: 2.21 – 2.59) to 8.80 (95% CI: 8.28 – 9.32) µM. Moreover, kinetic analysis and molecular docking simulations were performed to provide insight into the inhibition type as well as the interaction and binding mode of these active isolates with PTP1B. Our results revealed mixed-type PTP1B inhibition for all compounds tested. Docking simulations of these stilbene derivatives showed negative binding energies and close proximity to residues at the allosteric and catalytic sites of PTP1B. These findings suggest that these compounds may have a potential to be further developed as agents for the management of type 2 diabetes mellitus.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Unusual Prenylated Stilbene Derivatives with PTP1B Inhibitory Activity from Artocarpus styracifolius

Zhang

et al. 2019

Planta Med

View full text Add to dashboard Cite

show abstract

“…The inhibition constants (K i ) were determined by the intersection of Dixon plots, where the value of the x-axis was taken as K i . 13,14 α-Glucosidase Inhibitory Activity. The α-glucosidase inhibition assay was performed according to the reported protocols.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Antidiabetic Stilbenes from Peony Seeds with PTP1B, α-Glucosidase, and DPPIV Inhibitory Activities

Zhang

Geng

Huang

et al. 2019

J. Agric. Food Chem.

View full text Add to dashboard Cite

One unusual resveratrol tetramer, paeonilactiflorol (1), and 14 known compounds (2−15) were isolated from peony seeds (Paeonia lactiflora) under the guidance of bioassay. Paeonilactiflorol (1) was determined by extensive HRESIMS, UV, IR, 1D and 2D NMR spectroscopic analyses. Most of the stilbenes showed obvious inhibition on PTP1B and αglucosidase, superior to the monoterpene glycosides. Especially, the stilbene tetramer (1) and trimer (8) exhibited high activity inhibiting both PTP1B with IC 50 values of 27.23 and 27.81 μM and α-glucosidase with IC 50 values of 13.57 and 14.39 μM. Two trans-dimers (4 and 5) also showed dipeptidyl peptidase-4 (DPPIV) inhibitory activity (55.35% and 61.26%, 500 μM) in addition to PTP1B and α-glucosidase. Enzyme kinetic study indicated that the types of inhibition on PTP1B were noncompetitive for 3 and 5 and mixed for 8 and 10. Quantitative analysis suggested that the stilbene trimers 8 (23.17 ± 0.36 mg/g) and 10 (15.24 ± 0.25 mg/g) were the main contents in peony seeds and should be responsible for the antidiabetic effects. This investigation supports the therapeutic potential of peony seeds in the treatment of diabetes with stilbenes as the active constituents.

show abstract

“…A study conducted by Ha et al. ( 2018 ) indicated a positive association of stilbenes to inhibit PTP1B activity. In this study, ligand C and ligand A in silico molecular docking simulations were used to check the effects of stilbenes.…”

Section: Biological Effects Of Stilbenes Against Irmentioning

confidence: 99%

Role of stilbenes against insulin resistance: A review

Shazmeen

Haq

Rajoka

et al. 2021

Food Science & Nutrition

View full text Add to dashboard Cite

show abstract

PTP1B inhibitory activity and molecular docking analysis of stilbene derivatives from the rhizomes of Rheum undulatum L.

Cited by 27 publications

References 28 publications

Unusual Prenylated Stilbene Derivatives with PTP1B Inhibitory Activity from Artocarpus styracifolius

Unusual Prenylated Stilbene Derivatives with PTP1B Inhibitory Activity from Artocarpus styracifolius

Antidiabetic Stilbenes from Peony Seeds with PTP1B, α-Glucosidase, and DPPIV Inhibitory Activities

Role of stilbenes against insulin resistance: A review

Contact Info

Product

Resources

About