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J Nat Prod. 2016 Feb 26;79(2):267-73. doi: 10.1021/acs.jnatprod.5b00637. Epub 2016 Jan 20.

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

Author information

1
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Via Bovio 6, 28100, Novara, Italy.
2
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.
3
Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131, Napoli, Italy.

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.

PMID:
26788588
DOI:
10.1021/acs.jnatprod.5b00637
[Indexed for MEDLINE]

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