title: Turmeric Sesquiterpenoids: Expeditious Resolution, Comparative Bioactivity, and a New Bicyclic Turmeronoid.
abstract: An expeditious strategy to resolve turmerone, the lipophilic anti-inflammatory principle of turmeric (Curcuma longa), into its individual bisabolane constituents (ar-, α-, and β-turmerones, 2-4, respectively) was developed. The comparative evaluation of these compounds against a series of anti-inflammatory targets (NF-κB, STAT3, Nrf2, HIF-1α) evidenced surprising differences, providing a possible explanation for the contrasting data on the activity of turmeric oil. Differences were also evidenced in the profile of more polar bisabolanes between the Indian and the Javanese samples used to obtain turmerone, and a novel hydroxylated bicyclobisabolane ketol (bicycloturmeronol, 8) was obtained from a Javanese sample of turmeric. Taken together, these data support the view that bisabolane sesquiterpenes represent an important taxonomic marker for turmeric and an interesting class of anti-inflammatory agents, whose strict structure-activity relationships are worth a systematic evaluation.
authors.affiliation: Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Via Bovio 6, 28100, Novara, Italy.
authors.forename: Danilo
authors.initials: D
authors.lastname: Del Prete
authors.affiliation: Maimonides Biomedical Research Institute of Córdoba, Reina Sofía University Hospital, Department of Cell Biology, Physiology and Immunology, University of Córdoba , Avenida Menéndez Pidal s/n, 14004, Córdoba, Spain.
authors.forename: Estrella
authors.initials: E
authors.lastname: Millán
authors.affiliation: Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Via Bovio 6, 28100, Novara, Italy.
authors.forename: Federica
authors.initials: F
authors.lastname: Pollastro
authors.affiliation: Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131, Napoli, Italy.
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Chianese
authors.affiliation: Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131, Napoli, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Luciano
authors.affiliation: Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131, Napoli, Italy.
authors.forename: Juan A
authors.initials: JA
authors.lastname: Collado
authors.affiliation: Maimonides Biomedical Research Institute of Córdoba, Reina Sofía University Hospital, Department of Cell Biology, Physiology and Immunology, University of Córdoba , Avenida Menéndez Pidal s/n, 14004, Córdoba, Spain.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Munoz
authors.affiliation: Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Via Bovio 6, 28100, Novara, Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Appendino
authors.affiliation: Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131, Napoli, Italy.
authors.forename: Orazio
authors.initials: O
authors.lastname: Taglialatela-Scafati
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D030024:Curcuma / Q000737:chemistry*; D003474:Curcumin / Q000737:chemistry* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D007214:Indonesia; D007558:Italy; D008156:Luciferases / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000378:metabolism; D041681:NIH 3T3 Cells; D027343:Rhizome / Q000737:chemistry; D050796:STAT3 Transcription Factor / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D016328:NF-kappa B; D050796:STAT3 Transcription Factor; D012717:Sesquiterpenes; D014409:Tumor Necrosis Factor-alpha; C000608902:bicycloturmeronol; D008156:Luciferases; D003474:Curcumin