Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Abstract

Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti‐inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two‐step cross‐metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti‐inflammatory activity in vitro. All examined derivatives exhibited strong anti‐inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.

Novel strategies to prevent the development of multidrug resistance (MDR) in cancer

“…Curcuminoids, are a class of natural phenolic coloring compounds, which are isolated from the rhizomes of Curcuma longa [ 89 ]. Curcuminoids show a broad range of biological activities, including potent anti-inflammatory, anti-oxidant and anti-tumor properties [ 90 , 91 ]. Increasing evidence indicates that curcuminoids act to suppress proliferation, metastasis, invasion and angiogenesis of human cancers, through interactions with several intracellular signal transduction pathways [ 92 , 93 ].…”