ascorbic-acid and methyl-3-methoxy-4-hydroxystyryl-ketone

Natural products serve as a key source for the design, discovery and development of potentially novel drug like candidates for life threatening diseases. Curcumin is one such medicinally important molecule reported for an array of biological activities. However, it has major drawbacks of very poor bioavailability and solubility. Alternatively, structural analogs and degradants of curcumin have been investigated, which have emerged as promising scaffolds with diverse biological activities. Dehydrozingerone (DZG) also known as feruloylmethane, is one such recognized degradant which is a half structural analog of curcumin. It exists as a natural phenolic compound obtained from rhizomes of Zingiber officinale, which has attracted much attention of medicinal chemists. DZG is known to have a broad range of biological activities like antioxidant, anticancer, anti-inflammatory, anti-depressant, anti-malarial, antifungal, anti-platelet and many others. DZG has also been studied in resolving issues pertaining to curcumin since it shares many structural similarities with curcumin. Considering this, in the present review we have put forward an effort to revise and systematically discuss the research involving DZG with its biological diversity. From literature, it is quite clear that DZG and its structural analogs have exhibited significant potential in facilitating design and development of novel medicinally active lead compounds with improved metabolic and pharmacokinetic profiles.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antidepressive Agents; Antifungal Agents; Antimalarials; Antineoplastic Agents, Phytogenic; Antioxidants; Curcumin; Drug Design; Humans; Molecular Structure; Platelet Aggregation Inhibitors; Styrenes; Zingiber officinale

Protective effects of recently synthesised dehydrozingerone, M1OH (which is one half of the molecule of curcumin) and dimer of dehydrozingerone, D1(OH)2, as individual compounds (1 mM) and as equimolar binary (1:1) and ternary (1:1:1) mixtures with α-tocopherol (TOH) and/or ascorbyl palmitate (AscPH), were studied during bulk lipid autoxidation at 80 °C. The highest oxidation stability of lipid substrate, in the presence of individual compounds, was found for TOH, followed by D1(OH)2 and M1OH, determined from the main kinetic parameters (antioxidant efficiency, reactivity and capacity). AscPH did not show any protective effect. Synergism was obtained for the binary mixtures of (TOH+AscPH) [42.4%], (M1OH+TOH) [32.4%] and (M1OH+AscPH) [35.6%] and for the ternary mixture of (M1OH+TOH+AscPH) [28.7%]. Different protective effects observed were explained on the basis (of results) of TOH regeneration and its content determined by HPLC. These antioxidant binary and ternary mixtures can be used as functional components of foods with health-promoting effects.

Topics: alpha-Tocopherol; Antioxidants; Ascorbic Acid; Curcumin; Lipids; Molecular Structure; Oxidation-Reduction; Styrenes

The antioxidant property of dehydrozingerone and its analogs were investigated in the ferric-ascorbate induced lipid peroxidation model in rat brain homogenate. All the non phenolic compounds were either inactive or less active, while phenolic compounds with substitution at both meta positions were found to be more active than dehydrozingerone. Based on their IC50 values several of these compounds are more potent than vitamin E and hence may be of potential use in various diseases caused by oxidant stress.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Ascorbic Acid; Brain Chemistry; Female; Ferric Compounds; In Vitro Techniques; Lipid Peroxidation; Male; Rats; Structure-Activity Relationship; Styrenes; Thiobarbituric Acid Reactive Substances