Evaluation of the Antioxidant Activity of Capsiate Analogues in Polar, Nonpolar, and Micellar Media

Abstract

Synthesis of 10 capsiate analogues was conducted by lipase-mediated (Novozyme 435) esterification of vanillyl alcohol with different fatty acids. The antioxidant activity of the synthesized capsiates was evaluated using three in vitro assays: DPPH radical scavenging assay (polar medium), Rancimat assay (nonpolar medium), and autoxidation of linoleic acid (micellar medium). The objective of this study is to find the influence of structural characteristics of the alkyl chain of capsiate analogues on their antioxidant activity. In these assays, BHT and α-tocopherol were used as reference compounds. Both DPPH and Rancimat assays did not show any specific trend of antioxidant activity with the increase in lipophilicity and also with the type of fatty acids grafted to the phenolic moiety. In the Tween 20 micellar system for the inhibition of autoxidation of linoleic acid, vanillyl ester attached to a C18 alkyl chain (vanillyl stearate, oleate, and ricinoleate) exhibited maximum inhibition of autoxidation of linoleic acid.

A high correlation indicating for an evaluation of antioxidant activity and total phenolics content of various chilli varieties

“…The different varieties of chilli are being used in taste, flavor or aroma and pungency for beverages, pharmaceuticals, and/or cosmetics industries (Awang et al 2013). More recently, a number of biological properties and potential health benefits of consuming chillies have been investigated, e.g., powerful antioxidants (free radical scavengers) (Reddy et al 2011), antiinflammatory (Tag et al 2014), anti-arthritic (Chinn et al 2011), anti-neoplastic properties (Barbero et al 2010), anticancer (Meghvansi et al 2010) and antifungal (Singh and Chittenden 2008). Additionally, it also has a use as bird, animal and insect repellent as well as biochemical pesticides (Chinn et al 2011).…”

Synthesis and Characterization of Phenolic Lipids

“…On the other hand, the activities of enzymes also depend on the type of organic solvent, since some are known to inactivate or denature biocatalysts. Meanwhile, the advantages of using organic solvent media are increased solubility of hydrophobic compounds that permits for greater interactions between substrates and enzymes as well as advantageous, partitioning of substrates and products; speciically, this is because partitioning of products away from the enzyme can decrease the possibility of inhibition due to excess product around the biocatalyst [51,72].…”

“…The enzymatic synthesis of vanillyl-PUFA esters from ish oil and vanillyl alcohol in acetone solvent medium was studied by [10]. Lipase-catalyzed esteriication of vanillyl alcohol with diferent faty acids was carried out by [51] to the synthesis of capsiate analogs. Equimolar concentration of vanillyl alcohol and faty acid was solubilized in tert-butanol and esteriied using C. antartica lipase (Novozym 435) at 55°C for 4 h.…”

Practical large-scale production of dihydrocapsiate, a nonpungent capsaicinoid-like substance

“…As an example of enzymatic synthesis, the direct conversion of capsaicinoids to CSNs by lipase-catalyzed alcoholysis-type transacylation was reported by Castillo et al and Ishihara et al; however, these methods require considerable amounts of pure capsaicinoids as an acyl donor. 23,24) Another example of condensation of VOH (8) with a fatty acid or a fatty acid methyl ester using the immobilized enzyme Novozym 435 (Novozymes, Denmark), a kind of lipase, in acetone was reported by Kobata et al 25,26) ; however, since the reaction using an enzyme is an equilibrium reaction, the conversion yield of the products was approximately 70-80%, even after long durations of reaction time or by addition of a dehydrating agent such as molecular sieves. Therefore, the equilibrium must shift to the products in some way to improve the yield.…”