Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies

Zhao, Zhaohui; Moghadasian, Mohammed H.

doi:10.1007/s11101-009-9145-5

Cited by 100 publications

(88 citation statements)

References 98 publications

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“…In general, the metabolism of polyphenols may occur in the liver, intestinal mucosa, kidney, and/or by the intestinal microflora, during which they may undergo a number of enzymatic reactions including dehydroxylation, demethylation, dehydrogenation, hydrogenation, O-methylation, sulfation, glucuronization, glutathione conjugation, and/or glycination (Zhao and Moghadasian 2010). There is limited knowledge on the metabolism of sinapic acid compared to caffeic, ferulic, and p-coumaric acids.…”

Section: Bioavailability and Metabolismmentioning

confidence: 99%

Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity

Nićiforović

Abramovič

2013

Comp Rev Food Sci Food Safe

385

207

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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.

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Section: Bioavailability and Metabolismmentioning

confidence: 99%

Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity

Nićiforović

Abramovič

2013

Comp Rev Food Sci Food Safe

385

207

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“…The antioxidant capacity of compounds per se does not predict the ability to protect cells exposed to oxidative their stress [121,148]. Lipophilic antioxidants can penetrate cell membranes and may prevent oxidative damage to cells through membrane-related partitioning effects that supplement their chemical activities [121].…”

Section: Lipid Solubilitymentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

167

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Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

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“…Because of their beneficial effects on health (Navarre, 2009;Monro and Mishra, 2009) they are as important as phenolics, flavonoids, folate, anthocyanins, poly-amines and carotenoids (Ezequiel et al, 2013), which are considered as antioxidants, protecting against reactive oxygen species (ROS) when consumed through diet (Virgili and Scacini, 2003;Kris-Etherton et al, 2004). The bioavailability of these metabolites in potatoes seems to have benefits for human health, in anti-hypertensive activity, prevention of atherosclerosis, type 2 diabetes, Alzheimer's disease, cancer (Zhao and Moghadasian, 2010); there is also evidence of their inhibitory effect against HIV (Tamura et al, 2006), cataracts and macular degeneration (Chuah et al, 2008) and of antimicrobial properties (Muthuswamy and Ruspasinghe, 2007). As a therapeutic alternative, potatoes are also used empirically by the population for problems of the gastric mucosa, which shows that fresh potatoes and tocosh (an andean preservation technique) have an antioxidant defense and cytoprotective effect on the gastric mucosa (Sandoval-Vegas et al, 2010;Sandoval et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Phenolic compounds with antioxidant capacity of the native Andean potato (Solanum tuberosum L.) Huagalina variety in La Libertad- Peru

Rojas-Padilla

Vásquez-Villalobos

2016

Sc.Agropec

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Potato is grown and consumed throughout the world for their particular calorific nutritional value and vitamin C, but it also contains phytochemicals (secondary metabolites) that have been studied and found to have positive effects in preventing degenerative diseases in human health, such as hypertensive activity, and also atherosclerosis, type 2 diabetes, liver fibrosis, Alzheimer's disease, macular degeneration and cancer. We aimed to identify and quantify phenolic compounds in potatoes grown on El Zuro (EZ) and Huayatan Alto (HA) in Santiago de Chuco, La Libertad, Peru. The field trials were carried out in EZ (altitude 3750 m.a.s.l.) and HA (altitude 3150 m.a.s.l.) employing organic and inorganic fertilization respectively. Extraction from the peel and flesh was obtained separately, with the following solution: 50% methanol, 50% deionized water and 0.5% acetic acid. The sample was injected into the system UPLC -MS / MS, using ESI ionization (Electrospray Ionization) and fifteen external reference standards. Thirteen metabolites were detected in the flesh and potato peel. The highest content of secondary metabolites (mg/100 g DW) were: Chlorogenic acid (476.82 ± 63.58), neochlorogenic acid (87.90 ± 19.42) caffeic acid (77.53 ± 14.49) and vanillin (11.52 ± 1.38). The PCA (Principal Components Analysis) scores show that the highest concentration of metabolites was found in the peel of both cultivars. We concluded that the native potato Huagalina contains the genes expressed in different biosynthetic pathways of the metabolites found in this study.

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Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies

Cited by 100 publications

References 98 publications

Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity

Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Phenolic compounds with antioxidant capacity of the native Andean potato (Solanum tuberosum L.) Huagalina variety in La Libertad- Peru

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