Byung Sun Min's research while affiliated with Catholic University of Daegu and other places

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Publications (246)


Astraoleanosides E-P, oleanane-type triterpenoid saponins from the aerial parts of Astragalus membranaceus Bunge and their β-glucuronidase inhibitory activity
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February 2024

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42 Reads

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1 Citation

Bioorganic Chemistry

Manh Khoa Nguyen

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Jeong Ah Kim

Historically, Astragalus membranaceus Bunge has been used as a beneficial medicinal plant, particularly in the Asian traditional medical systems, for the treatment of various human diseases such as stomach ulcers, diarrhea, and respiratory issues associated with phlegm. In this study, a phytochemical characterization of the aerial parts of A. membranaceus led to the isolation of 29 oleanane-type triterpenoid saponins, including 11 new compounds named astraoleanosides E–P (6–9, 13, 14, 18–22), as well as 18 known ones. The structures of these compounds were elucidated using nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. Among them, astraoleanoside H (9) and cloversaponin III (15) demonstrated the most potent β-glucuronidase inhibitory activities, with IC50 values of 21.20 ± 0.75 and 9.05 ± 0.47 µM, respectively, compared to the positive control d-saccharic acid 1,4-lactone (IC50 = 20.62 ± 1.61 µM). Enzyme kinetics studies were then conducted to investigate the type of inhibition exhibited by these active compounds. In addition, the binding mechanism, key interactions, binding stability, and dynamic behavior of protein–ligand complexes were investigated through in silico approaches, such as molecular docking and molecular dynamics simulations. These findings highlight the promising potential of triterpenoid saponins from A. membranaceus as lead compounds for β-glucuronidase inhibitors, offering new possibilities for the development of therapeutic agents targeting various diseases where β-glucuronidase plays a crucial role.

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Phytochemical Investigation of Active Compounds from Celastrus orbiculatus Thunb. with α-Glucosidase Inhibitory Activity

December 2023

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30 Reads

Natural Product Sciences

Diabetes, characterized by elevated blood glucose levels, has a significant impact on cardiovascular, neural, and vascular systems. α-Glucosidase inhibitors have emerged as potential therapeutic agents for type 2 diabetes, as they slow carbohydrate digestion and reduce postprandial blood sugar levels. In this study, we investigated the phytochemical and pharmacological properties of Celastrus orbiculatus Thunb., renowned for its diverse phytochemical constituents and potential medicinal applications. Through the application of chromatographic and spectroscopic techniques, we successfully isolated and structurally elucidated 16 compounds from the stems of C. orbiculatus. The in vitro α-glucosidase inhibitory activity of these compounds was evaluated. Notably, celaphanol A (1) and (+) lariciresinol (7) exhibited strong α-glucosidase inhibition, with IC50 values of 8.06 ± 0.30 and 48.02 ± 0.47 µM, respectively. Enzyme kinetics analysis revealed that the most active compound 1 acted as a non-competitive inhibitor against α-glucosidase, with a Ki value of 7.77 ± 0.16 µM. These findings underscore C. orbiculatus as a valuable source for discovering and developing new α-glucosidase inhibitors. Furthermore, compound 1 shows promise as a candidate for natural herbal therapy targeting α-glucosidase inhibition. This suggests the potential for further investigation into its effectiveness through in silico or in vivo studies using a diabetes model.


Inhibition of α-Glucosidase by Abietane-Type Diterpenoids Isolated from Roots of Salvia miltiorrhiza

December 2023

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32 Reads

Natural Product Sciences

Salvia miltiorrhiza is a traditional medicinal plant used in Asian medicine for various therapeutic purposes. This plant contains numerous bioactive secondary metabolites, particularly abietane-type diterpenoids. In this study, 16 abietane-type diterpenoids were isolated from S. miltiorrhiza root extracts and structurally identified through advanced spectroscopic techniques. Among them, tanshinone IIA (6) and 15,16-dihydrotanshinone I (11) exhibited potent α-glucosidase inhibition, with IC50 values of 48.38 ± 0.57 and 48.02 ± 0.47 µM, respectively. Enzyme kinetic studies revealed that these compounds served as non-competitive inhibitors of α-glucosidase. Our findings indicate that natural compounds from S. miltiorrhiza show promise as safe and effective α-glucosidase inhibitors, providing an alternative approach to diabetes treatment. This study contributes to the growing interest in utilizing natural sources for α-glucosidase inhibition and their potential application in healthcare and disease management.



Inhibitory effects of phenylpropanoids and lignans isolated from the bark of Cinnamomum cassia L. on soluble epoxide hydrolase: Spectroscopic, kinetic, molecular docking, and molecular dynamics studies

December 2023

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20 Reads

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2 Citations

Journal of Molecular Structure

Cinnamomum cassia L., commonly known as cinnamon, is a widely used aromatic spice and medicinal plant with a rich history of culinary and therapeutic applications. In this study, a new phenylpropanoid, named di(1,3-dioxane)cassin A (4), and 13 known compounds (1‒3, 5‒14), were isolated from the bark of C. cassia. Their structures were successfully elucidated using modern spectroscopic techniques, such as nuclear magnetic resonance, high-resolution mass spectrometry, and circular dichroism spectroscopy. In addition, isolated compounds were evaluated for their inhibitory effects on soluble epoxide hydrolase (sEH). Compound 4 exhibited sEH inhibition with an IC50 value of 28.80 µM. Enzyme kinetics experiment indicated that compound 4 acted as a competitive sEH inhibitor. In silico methods, including molecular docking and molecular dynamics simulations, were employed to determine and understand the binding mechanism and dynamics behavior of this active compound with sEH.



Structures of compounds from nutmeg 1–24.
Key HMBC (→) and COSY (bold) correlations of compounds 14, 16, 18, and 21–24.
Enzyme kinetics analysis. (A–F) Lineweaver–Burk plots of compounds 19–24, respectively.
(A–F) Docking interaction diagrams of sEH inhibition by compounds 19–24, respectively. (Green lines: hydrogen bonding interactions, pink lines: alkyl and π–alkyl interactions, magenta lines: π–π T-shaped interactions, and light green: van der Walls interactions with the corresponding residues of sEH).
Molecular dynamics simulation of compounds 19–24 with sEH protein. (A) Potential energy, (B) RMSD of protein backbone (compounds 19: black, 20: red, 21: green, 22: blue, 23: yellow, and 24: maroon), (C–H) RMSF of residues in the complexes between sEH and compounds 19–24, respectively.

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Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg (Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase using in vitro and in silico approaches
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  • Full-text available

August 2023

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72 Reads

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6 Citations

Journal of Enzyme Inhibition and Medicinal Chemistry

Journal of Enzyme Inhibition and Medicinal Chemistry

Two new neolignans, myrifralignans F–G (14 and 18), four new diarylnonanoid derivatives, myrifragranones A–D (21–24), and 18 known compounds were isolated and structurally elucidated from nutmeg (Myristica fragrans Houtt.) seeds. The absolute configurations of these secondary metabolites were determined using the electronic circular dichroism technique. The inhibitory potential of these isolated compounds on soluble epoxide hydrolase (sEH) was investigated for the first time. Among them, malabaricones B and C (19 and 20) and four new compounds 21–24 displayed inhibitory activities against sEH, with IC50 values ranging from 14.24 to 46.35 µM. Additionally, the binding mechanism, key binding interactions, stability, and dynamic behaviour of the active compounds with the sEH enzyme were analysed using in silico molecular docking and dynamics simulations. Our findings suggest that nutmeg could become a promising natural source for discovering and developing new sEH inhibitors.

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Citations (74)


... In 2020, compounds 162 and 167 were isolated from the CHCl3-soluble part of an ethanolic extract of branches and twigs of BP by Malanik et al. [42]. In 2021, Vu et al. [14,44] isolated compounds 156-161 from the roots of BK. In addition, compounds 145, 146, 147, 152, and 153 were reported by Yadav et al. [45]. ...

Reference:

The Genus Broussonetia: An Updated Review of Phytochemistry, Pharmacology and Applications
Anti-inflammatory and Cytotoxic Activities of Phenolic Compounds from Broussonetia kazinoki
  • Citing Article
  • July 2021

Natural Product Sciences

... The main medicinal value of H. houttuyniae lies in its alkaloids, various volatile oils, flavonoids, as well as substances such as lauraldehyde, Houttuynin, and α-pinene. Houttuynin contains the small molecular antibacterial substance decanoyl acetaldehyde (Duan et al. 2008;Pham et al. 2023). The use of H. houttuyniae or decanoyl acetaldehyde as an additive in the feed for koi carp can enhance the animals' antioxidant capacity, reduce liver function damage, and improve immune system function (Woranam et al. 2022). ...

Alkaloids from Houttuynia cordata Thunb. and their chemotaxonomic significance
  • Citing Article
  • August 2023

Biochemical Systematics and Ecology

... It is a general expectation that glycoside motif functions to lessen the inhibitory potency. 30 However, glycosides of dihydroflavonol 11 (IC 50 = 2.39 μM) and flavone 13 (IC 50 = 0.22 μM) showed much better inhibitions than their mother skeletons (6 and 8) with 15-fold and 27-fold, respectively. ...

1,5-Anhydro-d-glucitol derivative and galloylated flavonoids isolated from the leaves of Acer ginnala Maxim. as dual inhibitors of PTP1B and α-glucosidase enzymes: In vitro and in silico studies
  • Citing Article
  • June 2023

Phytochemistry

Spectroscopic analysis, kinetic mechanism, computational docking, and molecular dynamics of active metabolites from the aerial parts of Astragalus membranaceus Bunge as tyrosinase inhibitors
  • Citing Article
  • March 2023

Bioorganic Chemistry

... Greater flexibility during the MD simulation is demonstrated by higher RMSF values 48,49 . Figure 5(C) shows that the RMSF value of the sEH-compound 19 complex was approximately 0.3 nm at residue Tyr383 and 0.45 nm at residues Leu408-Met419. ...

Insights into the inhibitory activity and mechanism of action of flavonoids from the stems and branches of Acer mono Maxim. against α-glucosidase via kinetic analysis, molecular docking, and molecular dynamics simulations
  • Citing Article
  • February 2023

Journal of Molecular Structure

... As the primary active component of Asarum, the volatile oil has pharmacological effects on the nervous, immune, and cardiovascular systems (Fung et al., 2021). Despite prior research on the chemical composition and pharmacological action of AEO, notable disagreements persist regarding its main components, such as methyl eugenol, safrole, and 3,5-dimethyltoluene (Hue et al., 2022;Gu et al., 2023). Therefore, MD was used to facilitate the enrichment and separation of AEO components. ...

Evaluation of genotoxicity and 13-week subchronic toxicity of root of Asarum heterotropoides var. seoulense (Nakai) Kitag
  • Citing Article
  • December 2022

Journal of Ethnopharmacology

... The Ames test was carried out according to the OECD test guidelines 471, which are based on the method of Maron and Ames with minor modications. 53 Briey, S. typhimurium strains TA98, TA100, TA1535, and TA1537 and E. coli WP2uvrA (Molecular Toxicology, Inc.) were used as tester strains in the presence or absence of 5% v/v Aroclor 1254-induced rat liver S9 metabolic system (S9 mix). Based on the dose-range test results, 10 and 20 ppm per plate were selected as the maximum concentration for the Ames test of MB (UV + TiO 2 ) and MB (focused ultrasonication). ...

Genotoxicity assessment of root extracts of Paeonia lactiflora Pall
  • Citing Article
  • December 2022

Mutation Research/Genetic Toxicology and Environmental Mutagenesis

... Additionally, molecular dynamics simulations provided insights into the dynamic properties of the protein-ligand complex formed by compound 1. These findings suggest that compound 1 could serve as a lead metabolite for developing new β-glucuronidase inhibitors [8]. ...

Inhibitory Effect of Coumarins and Isocoumarins Isolated from the Stems and Branches of Acer mono Maxim. against Escherichia coli β-Glucuronidase

Applied Sciences

... In Asian countries, natural products and herbal medicine have a longstanding history of being utilised for the treatment of various diseases because of their safety and low risk of side effects 11 . Nutmeg (Myristica fragrans Houtt.), a member of the Myristicaceae family, is an evergreen tropical tree, that is grown commercially in Asian countries, including China, Japan, Korea, and Vietnam 12 . ...

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies

Metabolites

... Gosogliptin, an anti-diabetic drug, along with Piperoleine B, Altretamine, Azanidazole, and Bortezomib, displays antiinflammatory and anticancer activities. [78][79][80][81][82][83][84][85][86] Furthermore, Phenothiazine has been recognized for its antibacterial activity, particularly in the treatment of tract infections. The analysis also revealed the presence of compounds such as 2-Phenylaminoadenosine, Lorcainide, Ebastine, (E)-entacapone, and rivastigmine, each with distinct pharmacological properties. ...

Anti-inflammatory activity and cytotoxicity against ovarian cancer cell lines by amide alkaloids and piperic esters isolated from Piper longum fruits: In vitro assessments and molecular docking simulation
  • Citing Article
  • August 2022

Bioorganic Chemistry