How Curcumin Works Preferentially with Water Soluble Antioxidants
In this study we investigated physicochemical characteristics of the curcumin radical by pulse radiolysis and laser flash photolysis. Two methylated curcumin derivatives, methylcurcumin and trimethylcurcumin, were synthesized to explore the role of phenol hydroxy and β-diketone moieties in the free...
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| Veröffentlicht in: | Journal of the American Chemical Society 2001-04, Vol.123 (13), p.3064-3068 |
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| container_end_page | 3068 |
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| container_issue | 13 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 123 |
| creator | Jovanovic, Slobodan V Boone, Charles W Steenken, Steen Trinoga, Manuela Kaskey, Robert B |
| description | In this study we investigated physicochemical characteristics of the curcumin radical by pulse radiolysis and laser flash photolysis. Two methylated curcumin derivatives, methylcurcumin and trimethylcurcumin, were synthesized to explore the role of phenol hydroxy and β-diketone moieties in the free radical chemistry of curcumin. Our results show that the initially generated β-oxo-alkyl transforms rapidly, probably via an intramolecular H-atom shift, into the phenoxyl-type curcumin radical. This phenoxyl does not react with oxygen, k < 105 M-1 s-1, and can be repaired by any water-soluble antioxidant with appropriate redox potential, E 6 < 0.83 V, for example, with vitamin C, k = (6 ± 1) × 106 M-1 s-1. A molecular mechanism of cancer chemoprevention by curcumin is proposed, with special emphasis on the synergism with water-soluble antioxidants. |
| doi_str_mv | 10.1021/ja003823x |
| format | Article |
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Two methylated curcumin derivatives, methylcurcumin and trimethylcurcumin, were synthesized to explore the role of phenol hydroxy and β-diketone moieties in the free radical chemistry of curcumin. Our results show that the initially generated β-oxo-alkyl transforms rapidly, probably via an intramolecular H-atom shift, into the phenoxyl-type curcumin radical. This phenoxyl does not react with oxygen, k < 105 M-1 s-1, and can be repaired by any water-soluble antioxidant with appropriate redox potential, E 6 < 0.83 V, for example, with vitamin C, k = (6 ± 1) × 106 M-1 s-1. 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A molecular mechanism of cancer chemoprevention by curcumin is proposed, with special emphasis on the synergism with water-soluble antioxidants.</description><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antioxidants - chemistry</subject><subject>Curcumin - chemistry</subject><subject>Free Radicals - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Pulse Radiolysis</subject><subject>Solubility</subject><subject>Water - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFOwzAMhiMEYmNw4AVQLyBxKDhJm3THaQIGmsTGBj1GaZuKbm0zklbb3p6gTnDhZFn-9Nv-ELrEcIeB4PuVBKARobsj1MchAT_EhB2jPgAQn0eM9tCZtSvXBiTCp6iHcRBywLyPRhO99catSduqqL1Ym7X1Zkblyqi6KWRZ7r1t0Xx6sWyU8Ra6bJNSeSM307sik3Vjz9FJLkurLg51gN4fH5bjiT99fXoej6a-pMGw8aM8VYABu9MyTJMkhTQiimUAIeN5gIETTEjKgoznGUjOQsWGmGZDJTnNZUAH6KbL3Rj91SrbiKqwqSpLWSvdWsFdOCGUOvC2A1OjrXW_iI0pKmn2AoP48SV-fTn26hDaJpXK_siDIAf4HVDYRu1-59KsBeOUh2I5W4iYfITz-OVNzB1_3fEytWKlW1M7J_8s_gZdqn_m</recordid><startdate>20010404</startdate><enddate>20010404</enddate><creator>Jovanovic, Slobodan V</creator><creator>Boone, Charles W</creator><creator>Steenken, Steen</creator><creator>Trinoga, Manuela</creator><creator>Kaskey, Robert B</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20010404</creationdate><title>How Curcumin Works Preferentially with Water Soluble Antioxidants</title><author>Jovanovic, Slobodan V ; Boone, Charles W ; Steenken, Steen ; Trinoga, Manuela ; Kaskey, Robert B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-8fce0101512d13bbc0c82e6d00567f41072122c64d7fd0a765e6913d9ea73fa43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antioxidants - chemistry</topic><topic>Curcumin - chemistry</topic><topic>Free Radicals - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Pulse Radiolysis</topic><topic>Solubility</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jovanovic, Slobodan V</creatorcontrib><creatorcontrib>Boone, Charles W</creatorcontrib><creatorcontrib>Steenken, Steen</creatorcontrib><creatorcontrib>Trinoga, Manuela</creatorcontrib><creatorcontrib>Kaskey, Robert B</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jovanovic, Slobodan V</au><au>Boone, Charles W</au><au>Steenken, Steen</au><au>Trinoga, Manuela</au><au>Kaskey, Robert B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>How Curcumin Works Preferentially with Water Soluble Antioxidants</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Antineoplastic Agents, Phytogenic - chemistry Antioxidants - chemistry Curcumin - chemistry Free Radicals - chemistry Oxidation-Reduction Pulse Radiolysis Solubility Water - chemistry |
| title | How Curcumin Works Preferentially with Water Soluble Antioxidants |
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