Ultrasound-Assisted Synthesis of some Curcumin Analogs and their Synergistic Effect with Ferulic Acid on α-Amylase Inhibition

Article Preview

Abstract:

Three curcumin analogs of dimethylaminobenzaldehyde derivatives, i.e., A, B and C were synthesized using a green method using the ultrasound-assisted technique, and the process was compared to the conventional method. The improvements were achieved by decreasing the reaction time from hours to minutes and giving the higher yields of the products. The products were tested as an antidiabetic agent by treated them as an inhibitor for α-amylase activity. The result of α-amylase inhibition showed that curcumin analogs (A, B, C) have high inhibition (77.06; 76.59; 78.34%) with IC50value 23.64; 1.36; and 5.93 μg/mL, respectively. Meanwhile, the α-amylase inhibition of the combination between curcumin analog and ferulic acid showed that the curcumin analog C gave the highest inhibition level of 95.94% with IC50 13.38 μg/mL. The combination of curcumin analog A and ferulic acid has a strong synergistic effect with a combination index (CI) value of less than 1, i.e., 0.33. These curcumin analogs are quite potent in inhibiting the activity of α-amylase so that it can be a good candidate for antidiabetic drugs.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

120-126

Citation:

Online since:

March 2019

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2019 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] K. Ogurtsova, J.D. da Rocha Fernandes, Y. Huang, U. Linnenkamp, L. Guariguata, N.H. Cho, D. Cavan, J.E. Shaw, L.E. Makaroff, IDF Diabetes Atlas: Global estimates for the prevalence of diabetes for 2015 and 2040, Diabetes Res. Clin. Pract. 128 (2017) 40–50.

DOI: 10.1016/j.diabres.2017.03.024

Google Scholar

[2] World Health Organization, Global Report on Diabetes, Printed in France, ISSN 1098-6596, 978 (2016) 88.

Google Scholar

[3] M.R. Maradana, R. Thomas, B.J. O'Sullivan, Targeted delivery of curcumin for treating type 2 diabetes, Mol. Nutr. Food Res. 57 (2013) 1550–1556.

DOI: 10.1002/mnfr.201200791

Google Scholar

[4] M. Najafian, The effects of curcumin on alpha amylase in diabetics rats, Zahedan J. Res. Med. Sci. 17 (2015) e5198.

DOI: 10.17795/zjrms-5198

Google Scholar

[5] X. Yuan, H. Li, H. Bai, Z. Su, Q. Xiang, C. Wang, B. Zhao, Y. Zhang, Q. Zhang, Y. Chu, Y. Huang, Synthesis of novel curcumin analogues for inhibition of 11β-hydroxysteroid dehydrogenase type 1 with anti-diabetic properties, Eur. J. Med. Chem. 77 (2014) 223–230.

DOI: 10.1016/j.ejmech.2014.03.012

Google Scholar

[6] G. Liang, X. Li, L. Chen, S. Yang, X. Wu, E. Studer, E. Gurley, P.B. Hylemon, F. Ye, Y. Li, H. Zhou, Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin, Bioorg. Med. Chem. Lett. 18 (2008) 1525–1529.

DOI: 10.1016/j.bmcl.2007.12.068

Google Scholar

[7] N. Uddin, Md.R. Hasan, Md.M. Hossain, A. Sarker, A.H.M. Nazmul Hasan, A.F.M.M. Islam, M.M.H. Chowdhury, Md.S. Rana, In vitro α–amylase inhibitory activity and in vivo hypoglycemic effect of methanol extract of Citrus macroptera Montr. fruit, Asian Pac. J. Trop. Biomed. 4 (2014) 473–479.

DOI: 10.12980/apjtb.4.2014c1173

Google Scholar

[8] T. C. Chou, Drug combination studies and their synergy quantification using the chou-talalay method, Cancer Res. 70 (2010) 440–446.

DOI: 10.1158/0008-5472.can-09-1947

Google Scholar

[9] L. Mardiana, B. Ardiansah, A. Septiarti, R. Bakri, G. Kosamagi, Ultrasound-assisted synthesis of curcumin analogs promoted by activated chicken eggshells, AIP Conf. Proc.1862 030096 (2017) 1–6.

DOI: 10.1063/1.4991200

Google Scholar

[10] Y.J. Lei, Y. Bi, O.Y. Jie, Synthesis of some Curcumin analogues under ultrasound irradiation, Adv. Mater. Res. 332–334 (2011) 1623–1626.

DOI: 10.4028/www.scientific.net/amr.332-334.1623

Google Scholar

[11] P. Dewi, N. Lotulung, T. Mozef, C. Risdian, A. Darmawan, In vitro antidiabetic activities of extract and isolated flavonoid compounds from artocarpus altilis (parkinson) fosberg, Indones. J. Chem. 14 (2014) 7–11.

DOI: 10.22146/ijc.21261

Google Scholar

[12] P.K. Prabhakar, R. Prasad, S. Ali, M. Doble, Synergistic interaction of ferulic acid with commercial hypoglycemic drugs in streptozotocin induced diabetic rats, Phytomedicine. 20 (2013) 488–494.

DOI: 10.1016/j.phymed.2012.12.004

Google Scholar

[13] C.P. Reynolds, B.J. Maurer, Evaluating response to antineoplastic drug combinations in tissue culture models, Methods Mol. Med. 110 (2005) 173–183.

DOI: 10.1385/1-59259-869-2:173

Google Scholar