Abstract
Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds.
Highlights
Curcumin, a natural product used in traditional medicine, has been extensively studied for its multiple pharmacological effects on biological systems, to understand its chemical properties, and to improve its poor bioavailability [1]
48.4(1)◦, 2.2(1)◦ and 63.3(1)◦, 2.9(1)◦ and 81.0(1)◦, 13.2(1)◦ and 25.8(2)◦, 3.2(1)◦ and 88.2(1)◦, and 6.4(1)◦, and 77.5(1)◦, respectively. This clearly shows that in structures 7, 9, 10, 13, and 14, the –C-phenyl is coplanar with the central moiety
In contrast with the reported high antioxidant activity of curcumin and derivatives [1], the retro-curcuminoids described here had no important prophylactic effect on the oxidative process, probably because of the structural occupation of phenyl groups and the loss of free hydroxyls, chemical groups related to activity against free radicals
Summary
Curcumin (diferuloylmethane), a natural product used in traditional medicine, has been extensively studied for its multiple pharmacological effects on biological systems, to understand its chemical properties, and to improve its poor bioavailability [1]. Chemo-preventive, a precursor of theand biosynthesis of curcumin, hasproperties been described as aiscompound antitumoral, photo-protective biological [12]. A precursor of the biosynthesis of curcumin, has been described as a compound with compound structurally related to biosynthesis or degradation of curcumin and is present as a minor antitumoral, chemo-preventive, and photo-protective biological properties is a phenolic structurally related torhizomes biosynthesis or degradation of curcumin and is present as a DHZ minor component in the of Zingiber officinale Roscoe (ginger). Hascomponent been compound structurally to biosynthesis or degradation of curcumin andDHZ is present as a minor to have antimicrobial, pro-healing, anti-Parkinson, anti-Alzheimer, in theshown rhizomes ofradioprotective, Zingiberrelated officinale. DHZ and related compounds, acetylated ferulic acid carboxylic theofcorresponding phenolic group of for theexample, second moiety. We explored the inhibition of lipoperoxidation and cytotoxic activity the new compounds
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