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Turmeric Sesquiterpenoids: Expeditious Resolution, Comparative Bioactivity, and a New Bicyclic Turmeronoid

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† Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Via Bovio 6, 28100, Novara, Italy
‡ 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
§ Dipartimento di Farmacia, Università di Napoli Federico II, Via Montesano 49, 80131, Napoli, Italy
*Tel: +39-0321375744. Fax: +39-0321375744. E-mail: [email protected] (G. Appendino).
*Tel: +39-081678509. Fax: +39-081678552. E-mail: [email protected] (O. Taglialatela-Scafati).
Cite this: J. Nat. Prod. 2016, 79, 2, 267–273
Publication Date (Web):January 20, 2016
https://doi.org/10.1021/acs.jnatprod.5b00637
Copyright © 2016 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    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.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.5b00637.

    • 1H and 2D NMR spectra for bicycloturmeronol (8) and NMR data for turmerones (PDF)

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