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

Journal of Natural Products
Danilo Del PreteOrazio Taglialatela-Scafati

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.

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Citations

Jun 29, 2016·Journal of Natural Products·Federica PollastroGiovanni Appendino
Apr 20, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bing LinWei-Cheng Yuan
Jul 29, 2017·Journal of Natural Products·Danilo Del PreteGiovanni Appendino
Feb 29, 2020·Expert Opinion on Drug Discovery·Li-Ming ZhouGuang-Fu Yang
Aug 18, 2020·Journal of Clinical Biochemistry and Nutrition·Hitoshi AshidaYoko Yamashita
Apr 19, 2019·Chemical Science·Suppachai KrajangsriPher G Andersson
Jan 1, 2021·Plants·María Dolores Ibáñez, María Amparo Blázquez
Aug 31, 2020·Redox Biology·Laura CasaresLaureano de la Vega
Apr 12, 2017·The Journal of Organic Chemistry·Kim SpielmannJean-Marc Campagne

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