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Published in: Inflammopharmacology 2-3/2016

Open Access 01-06-2016 | Original Article

The antioxidant activity of some curcuminoids and chalcones

Authors: Münevver Sökmen, M. Akram Khan

Published in: Inflammopharmacology | Issue 2-3/2016

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Abstract

The antioxidant properties of the synthetic compound (C1)–(C8), which comprised 7 curcuminoids and a chalcone, were evaluated by two complementary assays, DPPH and β-carotene/linoleic acid. It was found that, in general, the free radical scavenging ability of (C1)–(C8) was concentration-dependent. Compounds (C1) and (C4), which contained (4-OH) phenolic groups, were found to be highly potent antioxidants with higher antioxidant values than BHT suggesting that synthetic curcuminoids are more potent antioxidants than standard antioxidants like BHT. Using β-carotene-linoleic acid assay, only the water-soluble 2, 4,6-trihydroxyphenolic chalcone (C5) showed 85.2 % inhibition of the formation of conjugated dienes reflecting on its potent antioxidant activity.
Literature
go back to reference Abaza MS, Khan MA, Afzal M (2012) Chemistry, Biochemistry and Selective Cytotoxicity of Curcumin Analogues Against Human Cancer Cell Lines in Curcumin : Biosynthesis, Medicinal Uses and Health Benefits, Jun Sasaki and Masaki Kichida, Eds.; Nova Science Publishers Inc., NY Abaza MS, Khan MA, Afzal M (2012) Chemistry, Biochemistry and Selective Cytotoxicity of Curcumin Analogues Against Human Cancer Cell Lines in Curcumin : Biosynthesis, Medicinal Uses and Health Benefits, Jun Sasaki and Masaki Kichida, Eds.; Nova Science Publishers Inc., NY
go back to reference Burits M, Bucar F (2000) Antioxidant activity of Nigella sativa essential oil. Phytother Resear 14:323–328CrossRef Burits M, Bucar F (2000) Antioxidant activity of Nigella sativa essential oil. Phytother Resear 14:323–328CrossRef
go back to reference Cuendet M, Hostettmann K, Potterat O (1997) Iridoid glucosides with free radical scavenging properties from Fagraea blumei. Helv Chim Acta 80:1144–1152CrossRef Cuendet M, Hostettmann K, Potterat O (1997) Iridoid glucosides with free radical scavenging properties from Fagraea blumei. Helv Chim Acta 80:1144–1152CrossRef
go back to reference Dapkevicius A, Venskutonis R, van Beek TA, Linssen JPH (1998) Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in lithuania. J Sci Food Agric 77:140–146CrossRef Dapkevicius A, Venskutonis R, van Beek TA, Linssen JPH (1998) Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in lithuania. J Sci Food Agric 77:140–146CrossRef
go back to reference Fialkow L, Wang Y, Downey GP (2007) Reactive oxygen and nitrogen species as signaling molecules regulating neutrophil function. Free Radical Biology and Medicine 42(2):153–164 Fialkow L, Wang Y, Downey GP (2007) Reactive oxygen and nitrogen species as signaling molecules regulating neutrophil function. Free Radical Biology and Medicine 42(2):153–164
go back to reference Gutteridge JMC, Halliwell B (2000) Free radicals and antioxidants in the year 2000—a historical look to the future. Ann N Y Acad Sci 899:136–147CrossRefPubMed Gutteridge JMC, Halliwell B (2000) Free radicals and antioxidants in the year 2000—a historical look to the future. Ann N Y Acad Sci 899:136–147CrossRefPubMed
go back to reference Hahm E-R, Cheon G, Lee J, Kim B, Park C, Yang C-H (2002) New and known symmetrical curcumin derivatives inhibit the formation of Fos-Jun-DNA complex. Cancer Lett 184:89–96CrossRefPubMed Hahm E-R, Cheon G, Lee J, Kim B, Park C, Yang C-H (2002) New and known symmetrical curcumin derivatives inhibit the formation of Fos-Jun-DNA complex. Cancer Lett 184:89–96CrossRefPubMed
go back to reference Handler N, Jaeger W, Puschacher H, Leisser K, Erker T (2007) Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase (COX-1) inhibitors. Chem Pharm Bull 55:(1):64–71 Handler N, Jaeger W, Puschacher H, Leisser K, Erker T (2007) Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase (COX-1) inhibitors. Chem Pharm Bull 55:(1):64–71
go back to reference Huang MT, Ferraro T (1992) Phenolic compounds in food and cancer prevention. In: Phenolic compounds in food and their effects on health II. Antioxidants and cancer prevention. ACS Symposium Series 507; Houng MT, Ho CT, Lee CY, Eds.; American Chemical Society: Washington, DC, pp 8–34 Huang MT, Ferraro T (1992) Phenolic compounds in food and cancer prevention. In: Phenolic compounds in food and their effects on health II. Antioxidants and cancer prevention. ACS Symposium Series 507; Houng MT, Ho CT, Lee CY, Eds.; American Chemical Society: Washington, DC, pp 8–34
go back to reference Khan MA, Adams H (1995) Simple and Efficient Stereoselective Synthesis of (Z) and (E)-Alkylidene 2,3-Dimethoxybutenolides from L-Ascorbic Acid and D-Isoascorbic Acid. Synthesis, Thieme, 687–6929 Khan MA, Adams H (1995) Simple and Efficient Stereoselective Synthesis of (Z) and (E)-Alkylidene 2,3-Dimethoxybutenolides from L-Ascorbic Acid and D-Isoascorbic Acid. Synthesis, Thieme, 687–6929
go back to reference Khan MA, Boyes SA, Adams H (1996) Synthesis of some substituted oxaspiro[4,5] decanenones by way of intermolecular Diels-Alder reaction of alkylidine 2,3-dimethoxybutenolides obtained from L-ascorbic acid. Molecules, Springer-Verlag, 1, pp 27–36 Khan MA, Boyes SA, Adams H (1996) Synthesis of some substituted oxaspiro[4,5] decanenones by way of intermolecular Diels-Alder reaction of alkylidine 2,3-dimethoxybutenolides obtained from L-ascorbic acid. Molecules, Springer-Verlag, 1, pp 27–36
go back to reference Khan MA, El-Khatib R, Rainsford KD, Whitehouse MW (2012) Synthesis and anti-inflammatory properties of some aromatic and heterocyclic aromatic curcuminoids. Bioorganic Chem 40:30–38CrossRef Khan MA, El-Khatib R, Rainsford KD, Whitehouse MW (2012) Synthesis and anti-inflammatory properties of some aromatic and heterocyclic aromatic curcuminoids. Bioorganic Chem 40:30–38CrossRef
go back to reference Koleva II, van Beek TA, Linssen JPH, de Groot A, Evstatieva LN (2002) Screening of plant extracts for antioxidant activity: a comparative study on three testing methods. Phytochem Anal 13:8–17CrossRefPubMed Koleva II, van Beek TA, Linssen JPH, de Groot A, Evstatieva LN (2002) Screening of plant extracts for antioxidant activity: a comparative study on three testing methods. Phytochem Anal 13:8–17CrossRefPubMed
go back to reference Mishra S, Kapoor N, Mubarak Ali A, Pardhasaradhi BV, Kumari AL, Khar A, Misra K (2005) Differential apoptotic and redox regulatory activities of curcumin and its derivatives. Free Radic Biol Med 38:1353–1360CrossRefPubMed Mishra S, Kapoor N, Mubarak Ali A, Pardhasaradhi BV, Kumari AL, Khar A, Misra K (2005) Differential apoptotic and redox regulatory activities of curcumin and its derivatives. Free Radic Biol Med 38:1353–1360CrossRefPubMed
go back to reference Ou B, Huang D, Hampsch-Woodill M, Flanagan JA, Deemer EK (2002) Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assay: a comparative study. J Agric Food Chem 50:3122–3128CrossRefPubMed Ou B, Huang D, Hampsch-Woodill M, Flanagan JA, Deemer EK (2002) Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assay: a comparative study. J Agric Food Chem 50:3122–3128CrossRefPubMed
go back to reference Pabon HJJ (1964) Synthesis of curcumin and related compounds. Re. Trav Chim Pays Bas 83:379–386CrossRef Pabon HJJ (1964) Synthesis of curcumin and related compounds. Re. Trav Chim Pays Bas 83:379–386CrossRef
go back to reference Portes Elise, Gardrat Christian, Castellan Alain (2007) A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids. Tetrahedron 63:9092–9099CrossRef Portes Elise, Gardrat Christian, Castellan Alain (2007) A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids. Tetrahedron 63:9092–9099CrossRef
go back to reference Priyadarsini KI, Maity DK, Naik GH, Kumar MS, Unnikrishnan MK, Satav JG, Mohan H (2003) Role of phenolic OH and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Rad Biol Med 35(5):475–484CrossRefPubMed Priyadarsini KI, Maity DK, Naik GH, Kumar MS, Unnikrishnan MK, Satav JG, Mohan H (2003) Role of phenolic OH and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Rad Biol Med 35(5):475–484CrossRefPubMed
go back to reference Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R (1995a) Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94:79–83CrossRefPubMed Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R (1995a) Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94:79–83CrossRefPubMed
go back to reference Ruby AJ, Kuttan G, Dinesh Babub K, Rajasekharan KN, Kuttan R (1995b) Anti- tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94:79–83CrossRefPubMed Ruby AJ, Kuttan G, Dinesh Babub K, Rajasekharan KN, Kuttan R (1995b) Anti- tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94:79–83CrossRefPubMed
go back to reference Shakibaei M, John T, Schulze-Tanzil G, Lehmann I, Mobasheri A (2007) Suppression of NF-κB activation by curcumin leads to inhibition of expression of cyclo-oxygenase-2 and matrix metalloproteinase-9 in human articular hondrocytes: implications for the treatment of osteoarthritis. Biochem Pharmacol. doi:10.1016/j.bcp.2007.01.005 Shakibaei M, John T, Schulze-Tanzil G, Lehmann I, Mobasheri A (2007) Suppression of NF-κB activation by curcumin leads to inhibition of expression of cyclo-oxygenase-2 and matrix metalloproteinase-9 in human articular hondrocytes: implications for the treatment of osteoarthritis. Biochem Pharmacol. doi:10.​1016/​j.​bcp.​2007.​01.​005
Metadata
Title
The antioxidant activity of some curcuminoids and chalcones
Authors
Münevver Sökmen
M. Akram Khan
Publication date
01-06-2016
Publisher
Springer International Publishing
Published in
Inflammopharmacology / Issue 2-3/2016
Print ISSN: 0925-4692
Electronic ISSN: 1568-5608
DOI
https://doi.org/10.1007/s10787-016-0264-5

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