Synthesis, Isolation and Biological Evaluation of a New Active Quinone Methide Derived Curcuminoid

Tomer Sinai, Brijesh Singh, Amnon Sintov, Shimon Ben-Shabat

Research output: Contribution to journalArticlepeer-review

Abstract

A new curcuminoid, quinone methide cyclopentadione (QMC), was synthesized by oxidation of curcumin (CUR) in the presence of potassium ferricyanide, and further isolated and analyzed. QMC was found to be a relatively water-soluble curcuminoid, and more stable than CUR in citric-phosphate buffer solutions. Unlike CUR, QMC possesses a pH-independent stability. In plasma, QMC was degraded by 50% after 8 hours and reached 30% of its initial concentration after 48h, while CUR was thoroughly decomposed. It has been demonstrated that QMC has a similar anti-proliferative activity as CUR in three different cancer cell lines- MCF-7, PC3 and HT29. Molecular examination of QMC in cancer cells exhibited similar effect to CUR on two transcription factors, Nrf-2 and NF-κB. An anti-inflammatory activity of QMC was demonstrated by measuring MCP-1 secretion levels in TNFα-induced human keratinocytes cell culture, which had been pre-treated with either CUR or QMC. This report presents the advantages of the new quinone methide derived curcuminoid and its pharmaceutical potential as an alternative to the poorly soluble curcumin.
Original languageEnglish
Pages (from-to)48-55
Number of pages8
JournalThe Journal of Phytopharmacology
Volume10
DOIs
StatePublished - 27 Feb 2021

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