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Int. J. Mol. Sci. 2016, 17(2), 143; doi:10.3390/ijms17020143

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

1
Natural Product Division, Forest Research Institute Malaysia, 52109 Kepong, Malaysia
2
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
3
Centre for Natural Products and Drug Discovery (CENAR), University of Malaya, 50603 Kuala Lumpur, Malaysia
4
BioProcess and Molecular Engineering Research Unit (BPMERU), Department of Biotechnology Engineering, Faculty of Engineering, International Islamic University Malaysia, 53100 Kuala Lumpur, Malaysia
*
Author to whom correspondence should be addressed.
Academic Editor: Humberto González-Díaz
Received: 21 December 2015 / Revised: 12 January 2016 / Accepted: 15 January 2016 / Published: 14 February 2016
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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. View Full-Text
Keywords: hyaluronidase; ursolic acid; QSAR; semi empirical quantum chemical; molecular docking; Prismatomeris tetrandra (Roxb.) K. Schum; Rubiaceae hyaluronidase; ursolic acid; QSAR; semi empirical quantum chemical; molecular docking; Prismatomeris tetrandra (Roxb.) K. Schum; Rubiaceae
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Abdullah, N.H.; Thomas, N.F.; Sivasothy, Y.; Lee, V.S.; Liew, S.Y.; Noorbatcha, I.A.; Awang, K. Hyaluronidase Inhibitory Activity of Pentacylic Triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, Synthesis and QSAR Study. Int. J. Mol. Sci. 2016, 17, 143.

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