Analytical methodologies for quantification of ferulic acid and its oligomers

Barberousse, Hélène; Roiseux, Olivier; Robert, Christelle; Paquot, Michel; Deroanne, Claude; Blecker, Christophe

doi:10.1002/jsfa.3242

Cited by 82 publications

(61 citation statements)

References 141 publications

(130 reference statements)

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“…The missing 4-O-5-DFA 13 was later identified in trace amounts in a range of cereal grain insoluble fibers and this finding completed the spectrum of ferulate dehydrodimers to be found in plants (Bunzel et al 2000). Since Ralph's publication in 1994, various GC-MS/FID (Ralph et al 1994a;Bunzel et al 2001) and also HPLC-UVD/DAD methods have been described for analyzing ferulate dehydrodimers using synthesized (Ralph et al 1994a (Barberousse et al 2008). Thus, oxidatively coupled diferulates were identified in a variety of graminaceous but also non-graminaceous plants, e.g.…”

Section: Dehydrodiferulatesmentioning

confidence: 95%

Chemistry and occurrence of hydroxycinnamate oligomers

2009

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Hydroxycinnamates such as ferulic acid, sinapic acid and p-coumaric acid ester-linked to plant cell wall polymers may act as cross-links between polysaccharides to each other, but also to proteins and lignin. Although sinapates and p-coumarates also form cell wall cross-links by the formation of radically or photochemically formed dimers, ferulate derivatives are the quantitatively most important cross-links in the plant cell wall. While the first radically generated ferulate dimer was already identified almost 40 years ago, the spectrum of known ferulate dimers was considerably broadened within the last 15 years. Higher ferulate oligomers were generated in model systems, but also isolated from plant materials. Different model systems using either free hydroxycinnamic acids or their esters are reviewed, highlighting a discussion of the relevance of these models for the plant cell wall. The first ferulate trimer from plant material was discovered in 2003 and seven dehydrotrimers of ferulic acid were isolated from maize bran since. Some of these trimers were also identified in other plant materials such as wheat and rye grains, corn stover, sugar beet and asparagus. Formation mechanisms of ferulate trimers and implications for the plant cell wall are discussed. Ferulate tetramers are the highest oligomers isolated from plant materials so far. These compounds can theoretically cross-link up to four polysaccharide chains, assuming all cross-links are formed intermolecularly. Formation of intramolecular versus intermolecular polysaccharide crosslinks is a key question to be answered in the future if we want to judge properly the importance of hydroxycinnamate cross-links in the plant cell wall.

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Section: Dehydrodiferulatesmentioning

confidence: 95%

Chemistry and occurrence of hydroxycinnamate oligomers

2009

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“…CAPE is an active compo-nent of propolis and has been reported to possess antimito-genic, anticarcinogenic, antiinflammatory, and immuno-modulatory properties [71]. HCAs have ubiquitous distribution in the plant kingdom [32][33][34][35][36][37] and are abundantly found in tea leaves, coffee, red wine, various fruits, vegetables, and whole grains [32,38,39]. They have been categorized as structural and functional constituents of plant cell walls and also as bioactive ingredi-ents of the diet [40,41].…”

Section: Antioxidant Activity Of Hydroxycin-namic Acidsmentioning

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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“…To obtain soluble feruloylated oligosaccharides, enzymatic hydrolysis was carried out using 10 U Trichoderma viride xylanase (GH11 superfamily; Sigma) on 1 g AIR-treated triticale bran for 16 h. The samples were centrifuged, and the supernatant was analyzed at 375 nm in a spectrophotometer for the presence of feruloylated oligosaccharides (Micard et al 1994;Saulnier et al 1995;Barberousse et al 2008). For purification, the supernatant was loaded onto an XAD-2 column (10×1.6 cm) to bind free phenolics.…”

Section: Preparation and Purification Of Soluble Feruloylated Oligosamentioning

confidence: 99%