Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study

Abdullah, N.H. and Thomas, Noel Francis and Sivasothy, Y. and Lee, Vannajan Sanghiran and Liew, Sook Yee and Noorbatcha, I.A. and Awang, Khalijah (2016) Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study. International Journal of Molecular Sciences, 17 (2). p. 143. ISSN 1661-6596, DOI https://doi.org/10.3390/ijms17020143.

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Abstract

The mammalian hyaluronidase degrades hyaluronic acid by the cleavage of the β-1,4-glycosidic bond furnishing a tetrasaccharide molecule as the main product which is a highly angiogenic and potent inducer of inflammatory cytokines. Ursolic acid 1, isolated from Prismatomeris tetrandra, was identified as having the potential to develop inhibitors of hyaluronidase. A series of ursolic acid analogues were either synthesized via structure modification of ursolic acid 1 or commercially obtained. The evaluation of the inhibitory activity of these compounds on the hyaluronidase enzyme was conducted. Several structural, topological and quantum chemical descriptors for these compounds were calculated using semi empirical quantum chemical methods. A quantitative structure activity relationship study (QSAR) was performed to correlate these descriptors with the hyaluronidase inhibitory activity. The statistical characteristics provided by the best multi linear model (BML) (R2 = 0.9717, R2cv = 0.9506) indicated satisfactory stability and predictive ability of the developed model. The in silico molecular docking study which was used to determine the binding interactions revealed that the ursolic acid analog 22 had a strong affinity towards human hyaluronidase.

Item Type:	Article
Funders:	Ministry of Science and Technology Malaysia (MOSTI) under project number 02-03-10-SF0110, UMRG project no. RP020C-14AFR and Forest Research Institute Malaysia
Uncontrolled Keywords:	Hyaluronidase; Ursolic acid; QSAR; Semi empirical quantum chemical; Molecular docking; Prismatomeris tetrandra (Roxb.) K. Schum; Rubiaceae
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Department of Chemistry
Depositing User:	Ms. Juhaida Abd Rahim
Date Deposited:	12 Oct 2017 07:29
Last Modified:	01 Mar 2019 09:12
URI:	http://eprints.um.edu.my/id/eprint/17998

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