Phenolics and polyphenolics in foods, beverages and spices: Antioxidant activity and health effects – A review

Tannins are a unique group of phenolic metabolites with molecular weights between 500 and 30 000 Da, which are widely distributed in almost all plant foods and beverages. Proanthocyanidins and hydrolysable tannins are the two major groups of these bioactive compounds, but complex tannins containing structural elements of both groups and specific tannins in marine brown algae have also been described. Most literature data on food tannins refer only to oligomeric compounds that are extracted with aqueous-organic solvents, but a significant number of non-extractable tannins are usually not mentioned in the literature. The biological effects of tannins usually depend on their grade of polymerisation and solubility. Highly polymerised tannins exhibit low bioaccessibility in the small intestine and low fermentability by colonic microflora. This review summarises a new approach to analysis of extractable and non-extractable tannins, major food sources, and effects of storage and processing on tannin content and bioavailability. Biological properties such as antioxidant, antimicrobial and antiviral effects are also described. In addition, the role of tannins in diabetes mellitus has been discussed.

Tannins: current knowledge of food sources, intake, bioavailability and biological effects.

Oxidative stress, a result of an overproduction and accumulation of free radicals, is the leading cause of several degenerative diseases such as cancer, atherosclerosis, cardiovascular diseases, ageing and inflammatory diseases. Polyphenols form an important class of naturally occurring antioxidants, having innumerable biological activities such as anticancer, antifungal, antibacterial, antiviral, antiulcer and anticholesterol, to name a few. Among various polyphenols, gallic acid (3,4,5-trihydroxybenzoic acid), a naturally occurring low molecular weight triphenolic compound, has emerged as a strong antioxidant and an efficient apoptosis inducing agent. Starting from the bioavailability and the biosynthetic pathway of gallic acid, this review includes various in vitro, in vivo and in silico studies providing the mode of action, radical scavenging activity, ability to inhibit lipid peroxidation, maintenance of endogenous defense systems and metal ion chelation by this triphenolic molecule, along with a comprehensive overview of factors responsible for its high antioxidant activity. Gallic acid derivatives have also been found in a number of phytomedicines with diverse biological and pharmacological activities, including radical scavenging, interfering with the cell signaling pathways and apoptosis of cancer cells. The diverse range of applications of this simple polyphenol is due to a fine amalgam between its antioxidant and prooxidant potential. The existing literature on this dual behavior of gallic acid and its derivatives is reviewed here. This is followed by an account of their potential clinical and industrial applications.

Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications

https://bibliotecadigital.ipb.pt/bitstream/10198/755/1/Oliveira%20et%20al.%2c%202008.%20FCT%2c%2046%2c%202326-2331.pdf

Total phenols, antioxidant potential and antimicrobial activity of walnut (Juglans regia L.) green husks

https://bibliotecadigital.ipb.pt/bitstream/10198/719/1/Pereira%20et%20al.%2c%202007.%20Food%20Chem.%20Tox.%2c%2045%2c%202287-2295.pdf

Walnut (juglans regia l.) leaves: phenolic compounds, antibacterial activity and antioxidant potential of different cultivars

Phenolic acids (chlorogenic, caffeic, p-coumaric, ferulic, sinapic, ellagic, and syringic acid) as well as syringaldehyde and juglone were identified in ripe fruits of 10 walnut cultivars: Adams, Cisco, Chandler, Franquette, Lara, Fernor, Fernette, Alsoszentivani 117 (A-117), Rasna, and Elit. Analyses were done using a high-performance liquid chromatograph equipped with a diode array detector. Significant differences in the contents of identified phenolics were observed among cultivars. Phenolics were determined separately in the kernel and in the thin skin of the walnut, termed the pellicle. Not only in the kernel but also in the pellicle did syringic acid, juglone, and ellagic acid predominate (average values of 33.83, 11.75, and 5.90 mg/100 g of kernel; and 1003.24, 317.90, and 128.98 mg/100 g of pellicle, respectively), and the contents of ferulic and sinapic acid (average values of 0.06 and 0.05 mg/100 g of kernel and 2.93 and 2.17 mg/100 g of pellicle, respectively) were the lowest in all cultivars. The highest differences in the sum of all identified phenolics were observed between Rasna and Fernette fruits; in Rasna there were >2-fold higher contents of identified phenolics in both kernel and pellicle. It was found that the walnut pellicle is the most important source of walnut phenolics. The ratio between the contents in pellicle and kernel varied by at least 14.8-fold for caffeic acid (cv. Adams) and by up to 752.0-fold for p-coumaric acid (cv. Elit).

Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.

Traditional walnut liqueur – cocktail of phenolics

The enzyme polyphenol oxidase (PPO) catalyzes the oxidation of phenolic compounds into highly reactive quinones. Polymerization of PPO-derived quinones causes the postharvest browning of cut or bruised fruit, but the native physiological functions of PPOs in undamaged, intact plant cells are not well understood. Walnut (Juglans regia) produces a rich array of phenolic compounds and possesses a single PPO enzyme, rendering it an ideal model to study PPO. We generated a series of PPO-silenced transgenic walnut lines that display less than 5% of wild-type PPO activity. Strikingly, the PPO-silenced plants developed spontaneous necrotic lesions on their leaves in the absence of pathogen challenge (i.e. a lesion mimic phenotype). To gain a clearer perspective on the potential functions of PPO and its possible connection to cell death, we compared the leaf transcriptomes and metabolomes of wild-type and PPO-silenced plants. Silencing of PPO caused major alterations in the metabolism of phenolic compounds and their derivatives (e.g. coumaric acid and catechin) and in the expression of phenylpropanoid pathway genes. Several observed metabolic changes point to a direct role for PPO in the metabolism of tyrosine and in the biosynthesis of the hydroxycoumarin esculetin in vivo. In addition, PPO-silenced plants displayed massive (9-fold) increases in the tyrosine-derived metabolite tyramine, whose exogenous application elicits cell death in walnut and several other plant species. Overall, these results suggest that PPO plays a novel and fundamental role in secondary metabolism and acts as an indirect regulator of cell death in walnut.

/pdf/novel-roles-for-the-polyphenol-oxidase-enzyme-in-secondary-3ecnilg77e.pdf

Anita Solar

Papers

Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.

Traditional walnut liqueur – cocktail of phenolics

Novel Roles for the Polyphenol Oxidase Enzyme in Secondary Metabolism and the Regulation of Cell Death in Walnut

Seasonal variations of selected flavonoids, phenolic acids and quinones in annual shoots of common walnut (Juglans regia L.)

Identification and quantification of phenolic compounds in kernels, oil and bagasse pellets of common walnut (Juglans regia L.)