Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study

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...

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Main Authors:	Abdullah, Nor Hayati, Thomas, Noel Francis, Sivasothy, Yasodha, Lee, Vannajan Sanghiran, Liew, Sook Yee, Noorbatcha, Ibrahim Ali, Awang , Khalijah
Format:	Article
Language:	English
Published:	MDPI 2016
Subjects:	TP248.13 Biotechnology
Online Access:	http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/1/ijms-17-00143.pdf

id	iium-49229
recordtype	eprints
spelling	iium-492292016-12-23T02:22:27Z http://irep.iium.edu.my/49229/ Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study Abdullah, Nor Hayati Thomas, Noel Francis Sivasothy, Yasodha Lee, Vannajan Sanghiran Liew, Sook Yee Noorbatcha, Ibrahim Ali Awang , Khalijah TP248.13 Biotechnology 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. MDPI 2016-02 Article PeerReviewed application/pdf en http://irep.iium.edu.my/49229/1/ijms-17-00143.pdf Abdullah, Nor Hayati and Thomas, Noel Francis and Sivasothy, Yasodha and Lee, Vannajan Sanghiran and Liew, Sook Yee and Noorbatcha, Ibrahim Ali 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). pp. 143-1. ISSN 1661-6596 E-ISSN 1422-0067 http://www.mdpi.com/1422-0067/17/2/143 doi:10.3390/ijms17020143
repository_type	Digital Repository
institution_category	Local University
institution	International Islamic University Malaysia
building	IIUM Repository
collection	Online Access
language	English
topic	TP248.13 Biotechnology
spellingShingle	TP248.13 Biotechnology Abdullah, Nor Hayati Thomas, Noel Francis Sivasothy, Yasodha Lee, Vannajan Sanghiran Liew, Sook Yee Noorbatcha, Ibrahim Ali Awang , Khalijah Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
description	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.
format	Article
author	Abdullah, Nor Hayati Thomas, Noel Francis Sivasothy, Yasodha Lee, Vannajan Sanghiran Liew, Sook Yee Noorbatcha, Ibrahim Ali Awang , Khalijah
author_facet	Abdullah, Nor Hayati Thomas, Noel Francis Sivasothy, Yasodha Lee, Vannajan Sanghiran Liew, Sook Yee Noorbatcha, Ibrahim Ali Awang , Khalijah
author_sort	Abdullah, Nor Hayati
title	Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
title_short	Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
title_full	Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
title_fullStr	Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
title_full_unstemmed	Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study
title_sort	hyaluronidase inhibitory activity of pentacylic triterpenoids from prismatomeris tetrandra (roxb.) k. schum: isolation, synthesis and qsar study
publisher	MDPI
publishDate	2016
url	http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/ http://irep.iium.edu.my/49229/1/ijms-17-00143.pdf
first_indexed	2023-09-18T21:09:37Z
last_indexed	2023-09-18T21:09:37Z
_version_	1777411164861366272

Hyaluronidase inhibitory activity of Pentacylic triterpenoids from Prismatomeris tetrandra (Roxb.) K. Schum: Isolation, synthesis and QSAR study

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