Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity

Abstract

Sinapic acid is widespread in the plant kingdom (fruits, vegetables, cereal grains, oilseed crops, and some spices and medicinal plants) and as such is common in the human diet. Derivatives of sinapic acid are characteristic compounds in the Brassicaceae family. Sinapic acid shows antioxidant, antimicrobial, anti-inflammatory, anticancer, and anti-anxiety activity. 4-Vinylsyringol (a decarboxylation product of sinapic acid) is a potent antioxidative and antimutagenic agent which suppresses carcinogenesis and the induction of inflammatory cytokines. Sinapine (sinapoyl choline) is considered to be an acetylcholinesterase inhibitor which might have therapeutic applications in various disease treatments. Mainly due to their antioxidative activity, these compounds have been suggested for potential use in food processing, cosmetics, and the pharmaceutical industry, and this review aims to summarize current knowledge on the natural sources, chemistry, and biological activity of these substances.

Sinapinic and protocatechuic acids found in rapeseed: isolation, characterisation and potential benefits for human health as functional food ingredients

“…The stability and bioavailability of rapeseed phenolics is an issue in terms of the biorefining process and total utilisation of the rapeseed crop (Nićiforović and Abramovič, 2014;Dias et al, 2015). Phenolic compounds are susceptible to spontaneous oxidation and degradation (Tan et al, 2011).…”

“…Bioavailability is a key issue, given that little is known about the metabolism of SA and PCA. The epithelium of the small intestine plays a role in the bioavailability and metabolism of SA, involving both phase I and phase II metabolic enzymes; however, compared to other hydroxycinnamic acids such as ferulic acid, little is known about the metabolism of SA (Nićiforović and Abramovič, 2014). A recent bioavailability study with rats fed the herb Polygonum capitatum found that PCA was primarily distributed in the kidney tissue, followed by the lung tissue; however, >80% was excreted (Ma et al, 2016).…”

“…Reports suggest that rapeseed contains 240-590 μg/g of SA, while rapeseed cake (an initial by-product produced by crushing the rapeseeds to remove the oil) contains 170-454 μg/g of SA (Nićiforović and Abramovič, 2014). PCA is also found in rapeseed, with concentrations ranging from 28 μg/g to 612 μg/g in rapeseed hulls (Liu et al, 2012).…”

“…During rapeseed oil extraction, elevated temperatures and pressures cause SA to undergo structural changes, resulting in the formation of 4-vinylsyringol, a decarboxylation product of SA, along with syringaldehyde. The amount of SA derivatives (which include sinapoyl glucose, methyl sinapate, sinapoyl malate and 1-sinapoyl-2-feruloylgentiobiose) found in rapeseed ranges between 6,390 and 18,370 μg/g, but this is dependent on the method used to process the oil (Lomascolo et al, 2012;Nićiforović and Abramovič, 2014). walls and release of the bioactive contents (Khoddami et al, 2013).…”

In Vitro Antioxidant and Anti-rhizopus Activity of Methanolic Seed Extract of Camelina Sativa L.

“…It has been traditionally cultivated for vegetable oil and animal feed 10,11 . Camelina seed contains potential secondary metabolites namely, phytoalexin as camalexin 12 ; phenols as sinapine (sinapic acid) and phytic acid 13 ; antioxidants as tocopherols 11 , flavonols as quercetin 14 ; omega-3 fatty acids 15 and glucosinolates 16 . The seeds, leaves and roots extracts of camelina contained several anti-insect compounds as natural pesticides that showed strong antimicrobial activity towards a variety of pathogens 17 .…”