title: Cooking enhances curcumin anti-cancerogenic activity through pyrolytic formation of "deketene curcumin".
abstract: Curcumin is widely used in traditional Asian kitchen as a cooking ingredient. Despite its low bioavailability, epidemiological data, on low cancer incidence in Asia, suggest beneficial health effects of this compound. Therefore, the question arose whether cooking modifies the anti-cancerogenic effects of curcumin. To evaluate this, we pyrolysed curcumin with and without coconut fat or olive oil, and analysed the products by high-performance liquid chromatography (HPLC). A number of more hydrophilic curcumin isoforms and decomposition products, including a compound later identified by nuclear magnetic resonance spectroscopy (NMR) as "deketene curcumin" (1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one), formerly described as a synthetic curcumin derivative, were detected. Additionally, we proved that deketene curcumin, compared to curcumin, exhibits higher toxicity on B78H1 melanoma cells resulting in G2 arrest. In conclusion, deketene curcumin is formed as a consequence of pyrolysis during common household cooking, showing stronger anti-cancer effects than curcumin. Moreover, we propose a chemical reaction-pathway for this process.
authors.affiliation: Institute of Clinical and Experimental Surgery, Saarland University, Homburg/Saar, Germany; Department of Internal Medicine, Division of Immunotherapy and Gene Therapy, Saarland University Medical Center, Homburg/Saar, Germany.
authors.forename: Indra N
authors.initials: IN
authors.lastname: Dahmke
authors.affiliation: Institute of Pharmaceutical and Medicinal Chemistry, Saarland University, Saarbrucken, Germany.
authors.forename: Stefan P
authors.initials: SP
authors.lastname: Boettcher
authors.affiliation: Helmholtz-Institute of Pharmaceutical Research Saarland, Department of Drug Design and Optimization, Saarland University, Saarbrucken, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Groh
authors.affiliation: Department of Internal Medicine - Haematology/Oncology, St. Lukas Clinic, D-42697 Solingen, Germany; Department of Internal Medicine, Division of Immunotherapy and Gene Therapy, Saarland University Medical Center, Homburg/Saar, Germany. Electronic address: mahlknecht@gmx.de.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Mahlknecht
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D003296:Cooking / Q000379:methods*; D003474:Curcumin / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D051379:Mice
chemical_list: D000970:Antineoplastic Agents; D003474:Curcumin
keywords: Anti-cancerogenic; Bioavailability; Curcumin; G2-arrest; HPLC; Pyrolysis