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Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies

1
The United Graduate School of Agricultural Sciences, Kagoshima University, Korimoto 1-21-24, Kagoshima 890-0065, Japan
2
PAK Research Center, University of the Ryukyus, Okinawa 903-0213, Japan
3
Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Senbaru 1, Nishihara-cho, Okinawa 903-0213, Japan
4
Division of Computer Aided Drug Design, The Red-Green Research Centre, 218 Elephant Road, Dhaka 1205, Bangladesh
5
Subtropical Field Science Center, University of the Ryukyus, Senbaru 1, Nishihara-cho, Okinawa 903-0213, Japan
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(10), 2479; https://doi.org/10.3390/molecules23102479
Received: 9 August 2018 / Revised: 24 September 2018 / Accepted: 26 September 2018 / Published: 27 September 2018
(This article belongs to the Collection Bioactive Compounds)
Okinawa propolis (OP) and its major ingredients were reported to have anti-cancer effects and lifespan-extending effects on Caenorhabditis elegans through inactivation of the oncogenic kinase, p21-activated kinase 1 (PAK1). Herein, five prenylated flavonoids from OP, nymphaeol-A (NA), nymphaeol-B (NB), nymphaeol-C (NC), isonymphaeol-B (INB), and 3′-geranyl-naringenin (GN), were evaluated for their anti-inflammatory, anti-diabetic, and anti-Alzheimer’s effects using in vitro techniques. They showed significant anti-inflammatory effects through inhibition of albumin denaturation (half maximal inhibitory concentration (IC50) values of 0.26–1.02 µM), nitrite accumulation (IC50 values of 2.4–7.0 µM), and cyclooxygenase-2 (COX-2) activity (IC50 values of 11.74–24.03 µM). They also strongly suppressed in vitro α-glucosidase enzyme activity with IC50 values of 3.77–5.66 µM. However, only INB and NA inhibited acetylcholinesterase significantly compared to the standard drug donepezil, with IC50 values of 7.23 and 7.77 µM, respectively. Molecular docking results indicated that OP compounds have good binding affinity to the α-glucosidase and acetylcholinesterase proteins, making non-bonded interactions with their active residues and surrounding allosteric residues. In addition, none of the compounds violated Lipinski’s rule of five and showed notable toxicity parameters. Density functional theory (DFT)-based global reactivity descriptors demonstrated their high reactive nature along with the kinetic stability. In conclusion, this combined study suggests that OP components might be beneficial in the treatment of inflammation, type 2 diabetes mellitus, and Alzheimer’s disease. View Full-Text
Keywords: Okinawa propolis; prenylated flavonoids; inflammation; α-glucosidase; acetylcholinesterase; molecular docking; density functional theory; p21-activated kinase 1 Okinawa propolis; prenylated flavonoids; inflammation; α-glucosidase; acetylcholinesterase; molecular docking; density functional theory; p21-activated kinase 1
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MDPI and ACS Style

Shahinozzaman, M.; Taira, N.; Ishii, T.; Halim, M.A.; Hossain, M.A.; Tawata, S. Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies. Molecules 2018, 23, 2479. https://doi.org/10.3390/molecules23102479

AMA Style

Shahinozzaman M, Taira N, Ishii T, Halim MA, Hossain MA, Tawata S. Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies. Molecules. 2018; 23(10):2479. https://doi.org/10.3390/molecules23102479

Chicago/Turabian Style

Shahinozzaman, Md; Taira, Nozomi; Ishii, Takahiro; Halim, Mohammad A.; Hossain, Md A.; Tawata, Shinkichi. 2018. "Anti-Inflammatory, Anti-Diabetic, and Anti-Alzheimer’s Effects of Prenylated Flavonoids from Okinawa Propolis: An Investigation by Experimental and Computational Studies" Molecules 23, no. 10: 2479. https://doi.org/10.3390/molecules23102479

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