Curcumin and its carbocyclic analogs: Structure-activity in relation to antioxidant and selected biological properties

Molecules

Volumn 18, Issue 5, 2013, Pages 5389-5404

  Bhullar, Khushwant S ^a   Jha, Amitabh ^b   Youssef, Dani ^b,c   Rupasinghe, H P Vasantha ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

^b ACADIA UNIVERSITY   (Canada)

^c Universite Sainte Anne   (Canada)

Author keywords

Angiotensin converting enzyme; Antioxidant; Curcumin; HIV; Tyrosinase

Indexed keywords

ANTIOXIDANT; CURCUMIN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; DRUG DERIVATIVE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; MONOPHENOL MONOOXYGENASE; P16 PROTEASE, HUMAN IMMUNODEFICIENCY VIRUS 1;

ARTICLE; CELL LINE; CHEMISTRY; CURCUMA; CYTOLOGY; DRUG ANTAGONISM; ENZYMOLOGY; HUMAN; LUNG; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANTIOXIDANTS; CELL LINE; CURCUMA; CURCUMIN; HIV PROTEASE; HIV PROTEASE INHIBITORS; HUMANS; LUNG; MONOPHENOL MONOOXYGENASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84878308369     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18055389     Document Type: Article

References (31)

1. Goel, A.; Kunnumakkara, A.B.; Aggarwal, B.B. Curcumin as "Curecumin": From kitchen to clinic. Biochem. Pharmacol. 2008, 75, 787-809.
2. Parvathy, K.S.; Negi, P.S.; Srinivas, P. Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside. Food Chem. 2009, 115, 265-271.
3. Youssef, D.; Nichols, C.E.; Cameron, T.S.; DeClercq, E.; Balzarini, J.; Jha A. Design, synthesis and cytostatic activity of novel cyclic curcumin analogs. Bioorg. Med. Chem. Lett. 2007, 17, 5624-5629. (Pubitemid 47391311)
4. Zhao, X.C.; Zhang, L.; Yu, H.X.; Sun, Z.; Lin, X.F.; Tan, C.; Lu, R.R. Curcumin protects mouse neuroblastoma Neuro-2A cells against hydrogen-peroxide-induced oxidative stress. Food Chem. 2011. 129, 387-394.
5. Droge, W. Free radicals in the physiological control of cell function. Physiol. Rev. 2002, 82, 47-95. (Pubitemid 34654215)
6. Stohs, S.J. Role of free radicals in toxicology and disease. J. Basic Clin. Physiol. Pharmacol. 2011. 6, 205-228.
7. Shang, Y.J.; Jin, X.L.; Shang, X.L.; Tang, J.J.; Liu, G.Y.; Dai, F.; Qian, Y.P.; Fan, G.J.; Liu, Q.; Zhou, B. Antioxidant capacity of curcumin directed analogues: Structure-activity relationship and influence of microenvironment. Food Chem. 2010, 119, 1435-1442.
8. Lin, L.; Lee, K.H. Structure-activity relationships of curcumin and its analogues with different biological activities. Stud. Nat. Prod. Chem. 2006, 33, 785-812.
9. Balasuriya, N.; Rupasinghe, H.P.V. Antihypertensive properties of flavonoid-rich apple peel extract. Food Chem. 2012, 135, 2320-2325.
10. Sunagawa, Y.; Morimoto, T.; Wada, H.; Takaya, T.; Katanasaka, Y.; Kawamura, T.; Yanagi, S.; Marui, A.; Sakata, R.; Shimatsu, A.; Kimura, T.; Kakeya, H.; Fujita, M.; Hasegawa K. A natural p300-specific histone acetyltransferase inhibitor, curcumin, in addition to angiotensin-converting enzyme inhibitor, exerts beneficial effects on left ventricular systolic function after myocardial infarction in rats. Circ. J. 2011, 75, 2151-2159.
11. Sánchez-Ferrer, A.; Rodríguez-López, J.N.; García-Cánovas, F.; García-Carmona, F. Tyrosinase: A comprehensive review of its mechanism. Biochim. Biophys. Acta 1995, 1247, 1-11.
12. Hasoya, T.; Nakata, A.; Yamasaki, F.; Abas, F.; Shaari, K.; Lajis, N.H.; Morita, H. Curcumin like diarylpentanoid analogues as melanogenesis inhibitors. J. Nat. Med. 2011, 66, 166-176.
13. Lee, K.H.; Aziz, F.H.A.; Syahida, A.; Abas, F.; Shaari, K.; Israf, D.A.; Lajis, N.H. Synthesis and biological evaluation of curcumin like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities. Eur. J. Med. Chem. 2009, 44, 3195-3200.
14. McCutchan, F.E. Global Epidemiology of HIV. J. Med. Virol. 2006, 78, S7-S12. (Pubitemid 43993457)
15. Mazumder, A.; Raghavan, K.; Weinstein, J.; Kohn, K.W.; Pommier, Y. Inhibition of human immunodeficiency virus type-1 integrase by curcumin. Biochem. Pharmacol. 1995, 49, 1165-1170.
16. Otto, M.J.; Reid, C.D.; Garber, S.; Lam, P.Y.; Scarnati, H.; Bacheler, L.T.; Rayner, M.M.; Winslow, D.L. In vitro anti-human immunodeficiency virus (HIV) activity of XM323, a novel HIV protease inhibitor. Antimicrob. Agents Chemother. 1993, 34, 2606-2611. (Pubitemid 23357854)
17. Jha, A.; Zhao, J.; Cameron, T.S.; DeClercq, E.; Balzarini, J.; Manavathu, E.K.; Stables, J.P. Design, synthesis and biological evaluation of novel curcumin analogs as anti-neoplastic agents. Lett. Drug Des. Discov. 2006, 3, 304-310. (Pubitemid 43988111)
18. Nichols, C.E.; Youssef, D.; Harris, R.G.; Jha, A. Microwave-assisted synthesis of curcumin analogs. Arkivoc 2006, 13, 64-72. (Pubitemid 44315887)
19. Selvam, C.; Jachak, S.M.; Thilagavathi, R.; Chakraborti, A.K. Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797. (Pubitemid 40380734)
20. Huang, D.; Ou, B.; Prior, R.L. The chemistry behind antioxidant capacity assays. J. Agri. Food Chem. 2005. 53, 1841-1856. (Pubitemid 40403051)
21. Dutta, S.; Padhye, S.; Priyadarsini, K.I.; Newton, C. Antioxidant and antiproliferative activity of curcumin semicarbazone. Bioorg. Med. Chem. Lett. 2005, 15, 2738-2744. (Pubitemid 40732210)
22. Chen, S.Y.; Chen, Y.; Li, Y.P.; Chen, S.H.; Tan, J.H.; Ou, T.M.; Gu, L.Q.; Huang, Z.S. Design, synthesis, and biological evaluation of curcumin analogues as multifunctional agents for the treatment of Alzheimer's disease. Bioorg. Med. Chem. 2005, 19, 5596-5604.
23. Venkatesan, P.; Rao, M.N.A. Structure activity relationships for the inhibition of lipid peroxidation and the scavenging of free radicals by synthetic symmetrical curcumin analogues. J. Pharm. Pharmacol. 2010, 52, 1123-1128.
24. Li, H.L.; Liu, C.; Couto, G.D.; Ouzounian, M.; Sun, M.; Wang, A.B.; Huang, Y.; He, C.W.; Shi, Y.; Chen, X.; et al. Curcumin prevents and reverses murine cardiac hypertrophy. J. Clin. Invest. 2008. 118, 879-893. (Pubitemid 351364596)
25. Mazumder, A.; Neamati, N.; Sunder, S.; Schulz, J.; Pertz, H.; Eich, E.; Pommier, Y. Curcumin analogues with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J. Med. Chem. 1997, 40, 3057-3063. (Pubitemid 27391536)
26. Lue, B.M.; Nielsen, N.S.; Jacobsen, C.; Hellgren, L.; Guo, Z.; Xu, X. Antioxidant properties of modified rutin esters by DPPH, reducing power, iron chelation and human low density lipoprotein assays. Food Chem. 2010, 123, 221-230.
27. Rupasinghe, H.P.V.; Huber, G.M.; Embree, C.; Forsline, P.L. Red-fleshed apple as a source of functional beverages. Can. J. Plant Sci. 2010, 90, 95-100.
28. Huber, G.W.; Rupasinghe, H.P.V. Phenolic profiles and antioxidant properties of apple skin extracts. J. Food Sci. 2009, 74, C693-C700.
29. Noh, J.M.; Lee, Y.S. Inhibitory activities of hydroxyphenolic acid-amino acid conjugates on tyrosinase. Food Chem. 2011, 125, 953-957.
30. Xu, X.H.; Wan, M.; Dong, H.; But, P.P.; Foo, L.Y. Inhibitory Activity of flavonoids and tannins against HIV-1 Protease. Biol. Pharm. Bull. 2000, 23, 1072-1076.
31. Patrick, G.L. In An Introduction to Medicinal Chemistry; Oxford University Press Inc.: New York, NY, USA. 2005; p. 271.