Curcumin: A Mini Review on its Synthetic Derivatives

Authors: Mohd. Javed Naim1 & Adil Ahamad2 & Esra Tariq Anwer3 & Abdul Samad Salahuddin4
1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tishk International University, Erbil, Kurdistan Region, Iraq
2Department of Pharmacognosy, School of Pharmaceutical Education and Research, Jamia Hamdard, New Delhi, India
3Department of Pharmaceuticals, Faculty of Pharmacy, Tishk International University, Erbil, Kurdistan Region, Iraq
4Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tishk International University, Erbil, Kurdistan Region, Iraq

Abstract: Curcumin is a fat-soluble natural substance obtained from Curcuma longa and finds its applications in treatment of numerous disorders and diseases. Apart from its vast pharmacological profile, it is also used as a flavoring agent in the Asian subcontinent. This has drawn attention of the scientists to use it as an important scaffold to prepare its synthetic derivatives in order to improve the efficacy as well as potency of drug molecules and also reducing their toxicity effects. Here we tried to give some deeper insights of curcumin with a focus on its biological activities and various synthetic derivatives with a view to get potential lead molecules for future drug discovery and expansion of its medicinal profile.

Keywords: Curcumin, Curcuma Longa, Anticancer, Antibacterial, Antioxidant

Download the PDF Document

Doi: 10.23918/eajse.v8i3p251

Published: January 4, 2023

References

Aggarwal, B.B. and Harikumar, K.B. (2009). Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. The international journal of biochemistry & cell biology, 41(1), 40-59.

Alici, H., Tahtaci, H. and Demir, K. (2022). Design and various in silico studies of the novel curcumin derivatives as potential candidates against COVID-19-associated main enzymes. Computational biology and chemistry, 98, 107657.

Călinescu, M., Fiastru, M., Bala, D., Mihailciuc, C., Negreanu-Pîrjol, T. and Jurcă, B. (2019). Synthesis, characterization, electrochemical behavior and antioxidant activity of new copper (II) coordination compounds with curcumin derivatives. Journal of Saudi Chemical Society, 23(7), 817-827.

Deshpande, J., and Juturu, V. (2017). Curcumin compositions and uses thereof. US9724311B2.

Elmegeed, G.A., Ahmed, H.H., Hashash, M.A., Abd-Elhalim, M.M. and El-Kady, D.S. (2015). Synthesis of novel steroidal curcumin derivatives as anti-Alzheimer’s disease candidates: Evidences-based on in vivo study. Steroids, 101, 78-89.

Ferrari, E., Lazzari, S., Marverti, G., Pignedoli, F., Spagnolo, F. and Saladini, M. (2009). Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives. Bioorganic & medicinal chemistry, 17(8), 3043-3052.

Geschickter, C.F., Meadow, J.R. (1969). Curcumin derivatives. US3479345A.
Gupta, S.C., Patchva, S. and Aggarwal, B.B. (2013). Therapeutic roles of curcumin: lessons learned from clinical trials. The AAPS journal, 15(1), 195-218.

Halevas, E., Arvanitidou, M., Mavroidi, B., Hatzidimitriou, A.G., Politopoulos, K., Alexandratou, E., Pelecanou, M. and Sagnou, M. (2021). A novel curcumin gallium complex as photosensitizer in photodynamic therapy: Synthesis, structural and physicochemical characterization, photophysical properties and in vitro studies against breast cancer cells. Journal of Molecular Structure, 1240, 130485.

Han, H.K. (2011). The effects of black pepper on the intestinal absorption and hepatic metabolism of drugs. Expert opinion on drug metabolism & toxicology, 7(6), 721-729.

Hao, T., Wang, K., Zhang, S., Yang, S., Wang, P., Gao, F., Zhao, Y., Guo, N. and Yu, P. (2020). Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity. European Journal of Medicinal Chemistry, 207, 112798.

He, W., Wang, J., Jin, Q., Zhang, J., Liu, Y., Jin, Z., Wang, H., Hu, L., Zhu, L., Shen, M. and Huang, L. (2021). Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs. Bioorganic Chemistry, 114, 105080.

HemaIswarya, S. and Doble, M. (2006). Potential synergism of natural products in the treatment of cancer. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives, 20(4), 239-249.

Jagt, D.L.V., Deck, L.M., Abcouwer, S.F., Orlando, R.A., Royer, R.E., Weber, W.M., Bobrovnikova-Marjon, E.V., Hunsaker, L.A. (2014). Therapeutic curcumin derivatives US8841326B2.

Kanubaddi, K.R., Yang, S.H., Wu, L.W., Lee, C.H. and Weng, C.F. (2018). Nanoparticle-conjugated nutraceuticals exert prospectively palliative of amyloid aggregation. International Journal of Nanomedicine, 13, 8473.

Kaur, G., Invally, M. and Chintamaneni, M. (2016). Influence of piperine and quercetin on antidiabetic potential of curcumin. Journal of Complementary and Integrative Medicine, 13(3), 247-255.

Koroth, J., Mahadeva, R., Ravindran, F., Parashar, T.R., Teja, V., Karki, S.S. and Choudhary, B. (2022). Curcumin derivative 1, 2-bis [(3E, 5E)-3, 5-bis [(2-chlorophenyl) methylene]-4-oxo-1-piperidyl] ethane-1, 2-dione (ST03) induces mitochondria mediated apoptosis in ovarian cancer cells and inhibits tumor progression in EAC mouse model. Translational oncology, 15(1), 101280.

Krackov, M.H., Bellis, H.E. (1997). Process for the synthesis of curcumin-related compounds. US5679864A.

Lal, J., Gupta, S.K., Thavaselvam, D. and Agarwal, D.D. (2013). Biological activity, design, synthesis and structure activity relationship of some novel derivatives of curcumin containing sulfonamides. European Journal of Medicinal Chemistry, 64, 579-588.

Mehrabi, M., Esmaeili, S., Ezati, M., Abassi, M., Rasouli, H., Nazari, D., Adibi, H. and Khodarahmi, R. (2021). Antioxidant and glycohydrolase inhibitory behavior of curcumin-based compounds: Synthesis and evaluation of anti-diabetic properties in vitro. Bioorganic chemistry, 110, 104720.

Miller, J.C., Mitchell, M.O. (2009). Method for the synthesis of curcumin analogues. US7507864B2

Park, Y.D., Kinger, M., Min, C., Lee, S.Y., Byun, Y., Park, J.W. and Jeon, J. (2021). Synthesis and evaluation of curcumin-based near-infrared fluorescent probes for the in vivo optical imaging of amyloid-β plaques. Bioorganic Chemistry, 115, 05167.

Pettinari, R., Marchetti, F., Tombesi, A., Duan, F., Zhou, L., Messori, L., Giacomelli, C., Marchetti, L., Trincavelli, M.L., Marzo, T. and La Mendola, D. (2021). Ruthenium (II) 1, 4, 7-trithiacyclononane complexes of curcumin and bisdemethoxycurcumin: Synthesis, characterization, and biological activity. Journal of Inorganic Biochemistry, 218, 111387.

Raja, K., Alonso, A., Banerjee, P., Dolai, S., Corbo, C., Averick, S., Mogha, A., Debnath, S. (2011). Curcumin derivatives. WO2011106691A2.

Romanucci, V., Giordano, M., Pagano, R., Agarwal, C., Agarwal, R., Zarrelli, A. and Di Fabio, G. (2021). Solid-phase synthesis of curcumin mimics and their anticancer activity against human pancreatic, prostate, and colorectal cancer cell lines. Bioorganic & Medicinal Chemistry, 42, 116249.

Roxo, D.F., Arcaro, C.A., Gutierres, V.O., Costa, M.C., Oliveira, J.O., Lima, T.F.O., Assis, R.P., Brunetti, I.L. and Baviera, A.M. (2019). Curcumin combined with metformin decreases glycemia and dyslipidemia, and increases paraoxonase activity in diabetic rats. Diabetology & metabolic syndrome, 11(1), 1-8.

Ruan, B.F., Lu, X., Li, T.T., Tang, J.F., Wei, Y., Wang, X.L., Zheng, S.L., Yao, R.S. and Zhu, H.L. (2012). Synthesis, biological evaluation and molecular docking studies of resveratrol derivatives possessing curcumin moiety as potent antitubulin agents. Bioorganic & medicinal chemistry, 20(2), 1113-1121.

Sa, G. and Das, T., (2008). Anti-cancer effects of curcumin: cycle of life and death. Cell division, 3(1), 1-14.
Sagnou, M., Novikov, F.N., Ivanova, E.S., Alexiou, P., Stroylov, V.S., Titov, I.Y., Tatarskiy, V.V., Vagida, M.S.,

Pelecanou, M., Shtil, A.A. and Chilov, G.G. (2020). Novel curcumin derivatives as P-glycoprotein inhibitors: Molecular modeling, synthesis and sensitization of multidrug resistant cells to doxorubicin. European Journal of Medicinal Chemistry, 198, 112331.

Sahu, P.K., Sahu, P.K., Gupta, S.K., Thavaselvam, D. and Agarwal, D.D. (2012). Synthesis and evaluation of antimicrobial activity of 4H-pyrimido [2, 1-b] benzothiazole, pyrazole and benzylidene derivatives of curcumin. European journal of medicinal chemistry, 54, 366-378.

Shoba, G., Joy, D., Joseph, T., Majeed, M., Rajendran, R. and Srinivas, P.S.S.R. (1998). Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta medica, 64(04), 353-356.

Shrivash, M.K., Mishra, S., Pandey, J. and Misra, K. (2018). In-silico designing, chemical synthesis, characterization and in-vitro assessment of antibacterial properties of some analogues of curcumin. Microbial pathogenesis, 123, 89-97.

Subhedar, D.D., Shaikh, M.H., Nagargoje, A.A., Akolkar, S.V., Bhansali, S.G., Sarkar, D. and Shingate, B.B. (2020). Amide-linked monocarbonyl curcumin analogues: efficient synthesis, antitubercular activity and molecular docking study. Polycyclic Aromatic Compounds, 1-17.

Tavaf, Z., Dangolani, S.K., Yousefi, R., Panahi, F., Shahsavani, M.B. and Khalafi-Nezhad, A. (2020). Synthesis of new curcumin derivatives as influential antidiabetic α-glucosidase and α-amylase inhibitors with anti-oxidant activity. Carbohydrate Research, 494, 108069.

Tu, Z.S., Wang, Q., Sun, D.D., Dai, F. and Zhou, B. (2017). Design, synthesis, and evaluation of curcumin derivatives as Nrf2 activators and cytoprotectors against oxidative death. European journal of medicinal chemistry, 134, 72-85.

Wang, Z., Mu, W., Li, P., Liu, G. and Yang, J. (2021). Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo. European Journal of Pharmaceutical Sciences, 160, 105756.

WHO. (2000). Evaluation of Certain Food Additives. WHO Technical Report Series, vol. 891 WHO, Geneva.

Zhang, J., Wen, H., Shen, F., Wang, X., Shan, C., Chai, C., Liu, J. and Li, W. (2019). Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs. Bioorganic Chemistry, 92, 103163.

Zielińska, A., Alves, H., Marques, V., Durazzo, A., Lucarini, M., Alves, T.F., Morsink, M., Willemen, N., Eder, P., Chaud, M.V. and Severino, P. (2020). Properties, extraction methods, and delivery systems for curcumin as a natural source of beneficial health effects. Medicina, 56(7), 336.