Interactions of flavone and steroid from A. subintegra as potential inhibitors for porcine pancreatic lipase

Yuhanis Mhd Bakri

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Type :	article
Subject :	Q Science (General)
Main Author :	Yuhanis Mhd Bakri
Additional Authors :	Wong, Chee Fah Fauziah Abdullah Saripah Salbiah Syed Abdul Azziz Mastura Ibrahim
Title :	Interactions of flavone and steroid from A. subintegra as potential inhibitors for porcine pancreatic lipase

Place of Production :	Tanjong Malim
Publisher :	Fakulti Sains dan Matematik
Year of Publication :	2019
Corporate Name :	Universiti Pendidikan Sultan Idris

Abstract : Universiti Pendidikan Sultan Idris

Background: Obesity is one serious health condition that contributes to various chronic diseases. The inhibition of pancreatic lipase is a promising treatment for obesity. Objective: The present study was designed to investigate anti-porcine pancreatic lipase effect of isolated compounds from Aquilaria subintegra and its mechanism. Method: Compounds were isolated with serial column chromatography and their structure were identified using spectroscopic methods. Isolated compounds were tested for anti-lipase potential activity using colorimetric assay. The prediction of energy binding between isolated compounds and enzyme was described using YASARA software. Results: Four compounds were successfully isolated from the bark of A. subintegra, namely, 5-hydroxy-7,4’-dimethoxyflavone, luteolin-7,3’,4’-trimethyl ether, 5,3’-dihydroxy-7,4’-dimethoxyflavone and β-sitosterol. The results indicated that all compounds displayed promising pancreatic lipase inhibitory activity ranging between of 6% to 53% inhibition. Compound 5-hydroxy-7,4’-dimethoxyflavone was a competitive inhibitor and decreases the enzyme catalysis. Meanwhile, βsitosterol was a non- competitive inhibitor since the latter was bind allosterically toward enzyme. Conclusion: This finding is significant for further investigation of bioactive compounds from A. subintegra on animal study

References

[1] Wu, X.; He, W.; Zhang, H.; Li, Y.; Liu, Z.; He, Z. Acteoside: a lipase inhibitor from the Chinese tea Ligustrum purpurascens kudingcha. Food Chem., 2014, 142, 306-310. [https://doi.org/10.1016/j.foodchem.2013.07.071]. [http://dx.doi.org/10.1016/j.foodchem.2013.07.071] [PMID:24001846]

[2] Kazmi, I.; Afzal, M.; Rahman, S.; Iqbal, M.; Imam, F.; Anwar, F. Antiobesity potential of ursolic acid stearoyl glucoside by inhibiting pancreatic lipase. Eur. J. Pharmacol., 2013, 709(1-3), 28-36. [https://doi.org/10.1016/j.ejphar.2013.02.032]. [http://dx.doi.org/10.1016/j.ejphar.2013.02.032] [PMID:23500199]

[3] Chidrawar, V.R.; Patel, K.N.; Sheth, N.R.; Shiromwar, S.S.; Trivedi, P. Antiobesity effect of Stellaria media against drug induced obesity in Swiss albino mice. Ayu, 2011, 32(4), 576-584. [https://doi.org/10.4103/0974- 8520.96137]. [http://dx.doi.org/10.4103/0974-8520.96137] [PMID: 22661858]

[4] Rains, T.M.; Agarwal, S.; Maki, K.C. Antiobesity effects of green tea catechins: a mechanistic review. J. Nutr. Biochem., 2011, 22(1), 1-7. [https://doi.org/10.1016/j.jnutbio.2010.06.006]. [http://dx.doi.org/10.1016/j.jnutbio.2010.06.006] [PMID:21115335]

[5] Ado, M.A.; Abas, F.; Mohammed, A.S.; Ghazali, H.M. Anti- and pro-lipase activity of selected medicinal, herbal and aquatic plants, and structure elucidation of an anti-lipase compound. Molecules, 2013, 18(12), 14651-14669. [https://doi.org/10.3390/molecules181214651]. [http://dx.doi.org/10.3390/molecules181214651] [PMID: 24287996]

[6] Yun, J.W. Possible anti-obesity therapeutics from nature--a review. Phytochemistry, 2010, 71(14-15), 1625-1641. [https://doi.org/10.1016/j.phytochem.2010.07.011].[http://dx.doi.org/10.1016/j.phytochem.2010.07.011] [PMID:20732701]

[7] Ahmed, B.; Ali Ashfaq, U.; Usman Mirza, M. Medicinal plant phytochemicals and their inhibitory activities against pancreatic lipase: molecular docking combined with molecular dynamics simulation approach. Nat. Prod. Res., 2018, 32(10), 1123-1129. [https://doi.org/10.1080/14786419.2017.1320786]. [http://dx.doi.org/10.1080/14786419.2017.1320786] [PMID: 28446025]

[8] Ibrahim, M.; Azziz, S.S.S.A.; Wong, C.F.; Din, W.N.I.W.M.; Mahamod, W.R.W.; Bakri, Y.M.; Ahmad, M.S.; Yahaya, R.; Ismail, N.H.; Salleh, W.M.N.H.W. Evaluation of Anti-Lipase Activity of Leaf and Bark Extracts from Aquilaria Subintegra and A. Malaccensis. Marmara Pharm. J., 2018, 22(1), 91-95. [http://dx.doi.org/10.12991/mpj.2018.46]

[9] Narita, Y.; Iwai, K.; Fukunaga, T.; Nakagiri, O. Inhibitory activity of chlorogenic acids in decaffeinated green coffee beans against porcine pancreas lipase and effect of a decaffeinated green coffee bean extract on an emulsion of olive oil. Biosci. Biotechnol. Biochem., 2012, 76(12), 2329-2331. [https://doi.org/10.1271/bbb.120518]. [http://dx.doi.org/10.1271/bbb.120518] [PMID: 23221697]

[10] Lim, S.M.; Goh, Y.M.; Kuan, W.B.; Loh, S.P. Effect of germinatedbrown rice extracts on pancreatic lipase, adipogenesis and lipolysis in 3T3-L1 adipocytes. Lipids Health Dis., 2014, 13(169), 169. [https://doi.org/10.1186/1476-511X-13-169]. [http://dx.doi.org/10.1186/1476-511X-13-169] [PMID: 25367070]

[11] Kang, Y-F.; Chien, S-L.; Wu, H-M.; Li, W-J.; Chen, C-T.; Li, HT.; Chen, H-L.; Chao, D.; Chen, S-J.; Huang, C-T. Secondary Metabolites from the Leaves of Aquilaria Sinensis. Chem. Nat. Compd., 2014, 50(6), 1110-1112. [https://doi.org/10.1007/s10600-014-1174-7]. [http://dx.doi.org/10.1007/s10600-014-1174-7]

[12] Hashim, Y.Z.H-Y.; Kerr, P.G.; Abbas, P.; Mohd Salleh, H. Aquilaria spp. (agarwood) as source of health beneficial compounds: A review of traditional use, phytochemistry and pharmacology. J. Ethnopharmacol., 2016, 189, 331-360. [https://doi.org/10.1016/j.jep.2016.06.055]. [http://dx.doi.org/10.1016/j.jep.2016.06.055] [PMID: 27343768]

[13] Jok, V.A.; Che Radzi, N.; Ku Hamid, K.H.A. Review: Pharmacological Properties of Aquilaria Spp. Adv. Mat. Res., 2015, 1113, 193-197. [https://doi.org/10.4028/www.scientific.net/AMR.1113.193].

[14] Ito, T.; Kakino, M.; Tazawa, S.; Watarai, T.; Oyama, M.; Maruyama, H.; Araki, Y.; Hara, H.; Iinuma, M. Quantification of polyphenols and pharmacological analysis of water and ethanol-based extracts of cultivated agarwood leaves. J. Nutr. Sci. Vitaminol. (Tokyo), 2012, 58(2), 136-142. [http://dx.doi.org/10.3177/jnsv.58.136] [PMID: 22790572]

[15] Ray, G.; Leelamanit, W.; Sithisarn, P.; Jiratchariyakul, W. Antioxidative Compounds from Aquilaria Crassna Leaf. Mahidol Univ. J. Pharm. Sci., 2014, 41(4), 54-58.

[16] Feng, J.; Yang, X.W.; Wang, R.F. Bio-assay guided isolation and identification of α-glucosidase inhibitors from the leaves of Aquilaria sinensis. Phytochemistry, 2011, 72(2-3), 242-247. [https://doi.org/10.1016/j.phytochem.2010.11.025]. [http://dx.doi.org/10.1016/j.phytochem.2010.11.025] [PMID:21215978]

[17] Sattayasai, J.; Bantadkit, J.; Aromdee, C.; Lattmann, E.; Airarat, W. Antipyretic, analgesic and anti-oxidative activities of Aquilaria crassna leaves extract in rodents. J. Ayurveda Integr. Med., 2012, 3(4), 175-179. [https://doi.org/10.4103/0975-9476.104427]. [http://dx.doi.org/10.4103/0975-9476.104427] [PMID: 23326086]

[18] Hermoso, J.; Pignol, D.; Kerfelec, B.; Crenon, I.; Chapus, C.; Fontecilla-Camps, J.C. Lipase activation by nonionic detergents. The crystal structure of the porcine lipase-colipase-tetraethylene glycol monooctyl ether complex. J. Biol. Chem., 1996, 271(30), 18007-18016. [http://doi.org/10.1074/jbc.271.30.18007]. [http://dx.doi.org/10.1074/jbc.271.30.18007] [PMID: 8663362]

[19] Bouchagra, S.; Benamia, F.; Djeghaba, Z. Docking studies of (-)-Epigallocatechin-3-gallate: A Potential Non-Competitive Pancreatic Lipase Inhibitor. Res. J. Pharm. Biol. Chem. Sci., 2016, 7(5), 2493-2505.

[20] Singh, S.; Kanwar, S. S. Antilipase activity guided fractionation of Vinca major. Journal of King Saud University - Science,, 2018, 30(4), 433–439. [http://dx.doi.org/10.1016/j.jksus.2017.03.005]

[21] Krieger, E.; Koraimann, G.; Vriend, G. Increasing the precision of comparative models with YASARA NOVA--a self-parameterizing force field. Proteins, 2002, 47(3), 393-402. [http://dx.doi.org/10.1002/prot.10104] [PMID: 11948792]

[22] Sai, V.; Chaturvedula, P.; Prakash, I. Isolation of Stigmasterol and β -Sitosterol from the Dichloromethane Extract of Rubus Suavissimus. Int. Curr. Pharm. J., 2012, 1(9), 239-242. [http://dx.doi.org/10.3329/icpj.v1i9.11613]

[23] Kumalo, H.M.; Bhakat, S.; Soliman, M.E.S. Theory and applications of covalent docking in drug discovery: merits and pitfalls. Molecules, 2015, 20(2), 1984-2000. [https://doi.org/10.3390/molecules20021984]. [http://dx.doi.org/10.3390/molecules20021984] [PMID: 25633330]

[24] Meng, X-Y.; Zhang, H-X.; Mezei, M.; Cui, M. Molecular docking: a powerful approach for structure-based drug discovery. Curr Comput Aided Drug Des, 2011, 7(2), 146-157. [http://dx.doi.org/10.2174/157340911795677602] [PMID:21534921]

[25] Martinez-Gonzalez, A.I.; Alvarez-Parrilla, E.; Díaz-Sánchez, Á.G.; de la Rosa, L.A.; Núñez-Gastélum, J.A.; Vazquez-Flores, A.A.; Gonzalez-Aguilar, G.A. In vitro Inhibition of Pancreatic Lipase by Polyphenols: A Kinetic, Fluorescence Spectroscopy and Molecular Docking Study. Food Technol. Biotechnol., 2017, 55(4), 519-530. [https://doi.org/10.17113/ftb.55.04.17.5138]. [http://dx.doi.org/10.17113/ftb.55.04.17.5138] [PMID: 29540986]

[26] Ahmed, B.; Ali Ashfaq, U.; Usman Mirza, M. Medicinal plant phytochemicals and their inhibitory activities against pancreatic lipase: molecular docking combined with molecular dynamics simulation approach. Nat. Prod. Res., 2018, 32(10), 1123-1129. [https: //doi.org/10.1080 /14786419.2017.1320786]. [http://dx.doi.org/10.1080/14786419.2017.1320786] [PMID:28446025]

[27] Veeramachaneni, G.K.; Raj, K.K.; Chalasani, L.M.; Annamraju, S.K.; Js, B.; Talluri, V.R. Shape based virtual screening and molecular docking towards designing novel pancreatic lipase inhibitors. Bioinformation, 2015, 11(12), 535-542. [https://doi.org/10.6026/97320630011535].[http://dx.doi.org/10.6026/97320630011535] [PMID: 26770027]

[28] Köhler, J.; Wünsch, B. The allosteric modulation of lipases and its possible biological relevance. Theor. Biol. Med. Model., 2007, 4,34. [https://doi.org/10.1186/1742-4682-4-34]. [http://dx.doi.org/10.1186/1742-4682-4-34] [PMID: 17825093]

[29] Zainal, S.; Musa, M.; Idris, J.; Ku Hamid, K.H. Effect of Substrate Concentration and Reaction Time of Aquilaria Subintegra Leaves Extract on Inhibition of Pancreatic Lipase. IOP Conf. Ser. Mater. Sci. Eng., 2018, 358, p. 1–6. [http://dx.doi.org/10.1088/1757-899X/358/1/012039]

[30] Sergent, T.; Vanderstraeten, J.; Winand, J.; Beguin, P.; Schneider, Y. Phenolic Compounds and Plant Extracts as Potential Natural Anti-Obesity Substances. Food Chem., 2012, 135, 68-73. [http://dx.doi.org/10.1016/j.foodchem.2012.04.074]

[31] Liu, Y.; Chen, H.; Yang, Y.; Zhang, Z.; Wei, J.; Meng, H.; Chen, W.; Feng, J.; Gan, B.; Chen, X.; Gao, Z.; Huang, J.; Chen, B.; Chen, H. Whole-tree agarwood-inducing technique: an efficient novel technique for producing high-quality agarwood in cultivated Aquilaria sinensis trees. Molecules, 2013, 18(3), 3086-3106. [https://doi.org/10.3390/molecules18033086]. [http://dx.doi.org/10.3390/molecules18033086] [PMID: 23470337]

[32] Bahrani, H.; Mohamad, J.; Paydar, M.J.; Rothan, H.A. Isolation and characterisation of acetylcholinesterase inhibitors from Aquilaria subintegra for the treatment of Alzheimer’s disease (AD). Curr. Alzheimer Res., 2014, 11(2), 206-214. [https://doi.org/10.2174/1567205011666140130151344]. [http://dx.doi.org/10.2174/1567205011666140130151344] [PMID:24479629]

[33] Mohammed, A.; Al-Numair, K.S.; Balakrishnan, A. Docking studies on the interaction of flavonoids with fat mass and obesity associated protein. Pak. J. Pharm. Sci., 2015, 28(5), 1647-1653. [PMID: 26408884]

[34] Zhang, B.; Deng, Z.; Ramdath, D.D.; Tang, Y.; Chen, P.X.; Liu,R.; Liu, Q.; Tsao, R. Phenolic profiles of 20 Canadian lentil cultivars and their contribution to antioxidant activity and inhibitory effects on α-glucosidase and pancreatic lipase. Food Chem., 2015, 172, 862-872. [https://doi.org/10.1016/j.foodchem.2014.09.144]. [http://dx.doi.org/10.1016/j.foodchem.2014.09.144] [PMID: 25442631]

[35] Djeradi, H.; Rahmouni, A.; Cheriti, A. Antioxidant activity of flavonoids: a QSAR modeling using Fukui indices descriptors. J. Mol. Model., 2014, 20(10), 2476. [https://doi.org/10.1007/s00894-014-2476-1]. [http://dx.doi.org/10.1007/s00894-014-2476-1] [PMID: 25311723]

[36] Park, Y.; Lee, Y.U.; Kim, H.; Lee, Y.; Yoon, Y.A.; Moon, B.; Chong, Y.; Ahn, J.H.; Shim, Y.H.; Lim, Y. NMR Data of Flavone Derivatives and Their Anti-Oxidative Activities. Bull. Korean Chem. Soc., 2006, 27(10), 1537-1541. [https://doi.org/10.5012/bkcs.2006.27.10.1537]. [http://dx.doi.org/10.5012/bkcs.2006.27.10.1537]

[37] Mangoyi, R.; Midiwo, J.; Mukanganyama, S. Isolation and characterization of an antifungal compound 5-hydroxy-7,4′- dimethoxyflavone from Combretum zeyheri. BMC Complement. Altern. Med., 2015, 15, 405-416. [https://doi.org/10.1186/s12906-015-0934-7]. [http://dx.doi.org/10.1186/s12906-015-0934-7] [PMID: 26573005]

[38] Paniagua-Pérez, R.; Madrigal-Bujaidar, E.; Reyes-Cadena, S.; Molina-Jasso, D.; Gallaga, J.P.; Silva-Miranda, A.; Velazco, O.; Hernández, N.; Chamorro, G. Genotoxic and cytotoxic studies of beta-sitosterol and pteropodine in mouse. J. Biomed. Biotechnol., 2005, 2005(3), 242-247. [https://doi.org/10.1155/JBB.2005.242]. [http://dx.doi.org/10.1155/JBB.2005.242] [PMID: 16192682]

[39] Ong, S. L.; Mah, S. H.; Lai, H. Y. Isolated from Medicinal Herb and Inhibition Kinetics of Extracts from Eleusine Indica ( L .) Gaertner. J. Pharm., 2016, 1-9. [http://dx.doi.org/10.1155/2016/8764274]

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