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246 Wild Edible Plants
To date, more than 210 avonol aglycones are known (Ullah et al., 2020). The most
famous of them are quercetin, kaempferol, isorhamnetin, and myricetin. As the number of
hydroxyl groups increases and depending on their position, the color intensity increases.
The most common are compounds with 4- 5 hydroxyl groups, for example kaempferol –
3,5,7,4ʹ- tetrahydroxyavonol or quercetin – 3,5,7,3ʹ,4ʹ- pentahydroxyavonol.
Flavans are derivatives of 2- phenylchroman. Flavan derivatives include catechins
(avan- 3- ols), leucoanthocyanidins (avan- 3,4- diols), and anthocyanidins. Catechins
are the most reduced avonoid compounds (Veiko et al., 2021).
The avan- 3- ol molecule contains two asymmetric carbon atoms in the pyran ring
(C2 and C3), so four isomers and two racemates are possible for each molecule. Thus,
(+ )- catechin and (- )- epicatechin isomers differ in the conguration of the hydroxyl
group at the 3rd carbon atom.
Unlike avonols, catechins and leucoanthocyanidins do not form glycosylated
forms. In plants, they exist as monomers or as condensed compounds (tannins).
Catechins are the most reduced avonoid compounds, colorless ones that are easily
oxidized, and as a result they acquire different colors. For example, the different color
of tea (black, red, yellow) is due to the degree of catechin oxidation.
Leukoanthocyanidins (avan- 3,4- diols) are colorless, labile compounds that, when
heated with acids, are easily oxidized to the corresponding anthocyanidins and thus turn
Antioxidants from Wild Plants in Meat and Meat Products 247
into colored substances. A large number of red and blue colors of owers with different
shades is explained by the presence of anthocyanids (Ohmori, 2018).
A feature of the structure of anthocyanidins is the presence of free valence in oxygen
in the pyran ring. Due to the positive charge, anthocyanidins behave in an acidic solution as cations and form salts with acids, in an alkaline solution – as anions and form
salts with bases. Depending on the pH of the environment, the color of anthocyanidins
changes. In an acidic environment, they produce a pink, red color, and from blue to blue
with various shades in an alkaline environment (Eshghi et al., 2022).
Anthocyanidins are present in plants in the form of glycosides (anthocyanins).
They give plant tissues a variety of colors from pink to black- purple. The color of
anthocyanins is explained by the peculiarities of their structure, namely the number
and location of hydroxyl and methoxyl groups and the ability to form complexes with
metal ions (Mattioli et al., 2020). There are compounds with seven hydroxyl groups.
Methylation of hydroxyls further increases the variety of shades.
Flavanones are a small group of avonoids, the structure of which is based on a
dihydro- γ- pyrone ring. Flavanones (a hydrogenated derivatives of avone), unlike a-
vone, do not have a double bond between carbons in the 2nd and 3rd positions (De
Souza Farias et al., 2021). In the presence of alkalis, the ring opens and chalcones,
open- chain avonoids, are formed. In an acidic environment, chalcones are transformed
into avanones. For example, naringenin (avanone) and naringenin (chalcone) are
contained in immortelle owers in a free state and in the form of 5- monoglucoside.
Flavanones are optically active substances, usually found in plants as levorotatory forms. More than 30 representatives of this group of avonoids (aglycones) are
known, which are usually found together with chalcones in plants of the following families: roses, leguminous, and aster (Sykuła et al., 2021).
248 Wild Edible Plants
Flavanolols (dihydroavonols) differ from avanones by the presence of a hydroxyl
group at C- 3 and, like catechins, contain two asymmetric carbon atoms in the molecule
(C- 2 and C- 3) (Singla et al., 2019). Flavonolols are labile and, therefore, do not accumulate in plants in large quantities. The natural dihydroavonones corresponding to the
avonols kaempferol and quercetin are called aromadendrin and taxifolin.
Most dihydroavonols are isolated from the wood of coniferous (pine, spruce,
larch) and deciduous (eucalyptus, beech, cherry) trees.
Biosynthesis of avonoids is well studied. It was established that biosynthesis
proceeds in a mixed way. Core A is formed via the acetate- malonate pathway, ring B
via shikimic acid.
Shikimic acid, which is formed during the glycolytic breakdown of sugars, with the
participation of ATP, successively passes through a number of intermediate compounds
and turns into prefenic acid. First, amination of prefenic acid occurs with simultaneous
decarboxylation. Tyrosine is formed, the deamination of which leads to the formation
of p- coumaric acid, in the formula of which ring B or structural fragment – C3– C6 is
clearly visible (Heller & Forkmann, 2017).
The formation of ring A begins with the synthesis of triacetic acid. Acetic acid
(acetyl- CoA) is polymerized into triacetic acid, which reacts with p- coumaric acid. As a
result of their condensation, chain closure and enolization, a chalcone is formed (Heller
& Forkmann, 2017).
Chalcones are considered as the precursors of all other groups of avonoids.
When chalcones are oxidized, avones and avonols are formed, and when reduced,
anthocyanidins, catechins, and leucoanthocyanidins are formed (Davies et al., 2020).
Antioxidants from Wild Plants in Meat and Meat Products 249
9.2.3 Chemistry and Biological Effects of
Phenolic Acids
Phenolic acids are non- avonoid polyphenolic compounds present in plants and
characterized by a carboxyl group attached to a benzene ring (Kiokias et al., 2020). They
are derivatives of two main phenolic compounds, benzoic and cinnamic acids. Examples
of hydroxybenzoic acid derivatives are gallic, p- hydroxybenzoic, vanillic, and syringic
acids, while caffeic, ferulic, sinapinic, and p- coumaric acids belong to hydroxycinnamic
acids. In the past 10 years, a variety of natural phenolic acids, at least 30 hydroxy- and
polyhydroxybenzoic acids with biological activity, have been reported (Kumar &
Goel, 2019).
Phenolic acids are mainly secondary metabolites of plants. They determine the specic taste and aroma of vegetables and fruits, and also have unique useful properties
(Rashmi & Negi, 2020). Therefore, increasing the content of phenolic acids in plants
increases their therapeutic and preventive properties. Biologically, phenolic acids are
important for plant growth and reproduction and are produced in response to environmental stressors to protect damaged plants (Marchiosi et al., 2020).
The most famous representatives of phenolic acids are caffeic, gallic, rosmarinic,
ferulic, and carnosic acids. Caffeic acid is 3,4- dioxycinnamic acid, which structurally
consists of phenolic and acrylic functional groups, the derivatives of which have a trans
conguration (Amarowicz & Pegg, 2019).
It is found in high concentrations in fruits (such as berries, apples, and pears) and
has been identied as the main phenolic component in coffee and coffee oil (Deotale
et al., 2019). In studies (Sørensen et al., 2017; Boke et al., 2019; Birková et al., 2020),
the antioxidant effect of caffeic acid was established.
Gallic acid is 3,4,5- trihydroxybenzoic acid, which is the main phenolic acid in tea
(Liu et al., 2020) and some berries (Okatan, 2020).
Gallic acid has high antioxidant activity. The antioxidant effect was demonstrated
by inhibition of secondary oxidation in systems, reduction of the peroxide number
250 Wild Edible Plants
and concentration of hexanal, especially in combination with alpha- tocopherol (Zhu
et al., 2019).
Rosmarinic acid is an ester of caffeic acid. It is found in such spicy herbs as rosemary, oregano, thyme, and sage as the main phenolic component (Oreopoulou et al.,
2018; Topal & Gulcin, 2022).
Adomako- Bonsu et al. (2017) and Keshavarz et al. (2021) showed its high anti oxidant capacity in relation to hydroperoxides and volatile carbonyl compounds.
Chemically, carnosic acid is a labdane- type phenolic diterpene found in plants such as
rosemary, sage, and carob tree (Li et al., 2018; Loussouarn et al., 2017).
The antiradical effect of grape seed, rosemary, and olive extracts was caused
by a high concentration of carnosic acid (Mira- Sánchez et al., 2020). Carnosic acid
was very effective in preventing the oxidation of sh oil, and its antioxidant activity
was stronger than that of vitamin E (Hrebień- Filisińska & Bartkowiak, 2021; Pavić
et al., 2019). It was also very effective in preserving unsaturated fatty acids of the ω- 3
family. In addition to antioxidant activity, the antibacterial activity of carnosic acid and
carnosol against both gram- positive and gram- negative bacteria was also conrmed
(Mo et al., 2022).
Ferulic acid is a phenolic acid found in coffee beans, apples, artichokes, peanuts,
ax seeds, and oranges (Li et al., 2021).
Antioxidants from Wild Plants in Meat and Meat Products 251
Antioxidant effects of ferulic acid in different systems was shown (Cavalcanti et al.,
2021; Stompor- Gorący & Machaczka, 2021; Yang et al., 2021).
9.3 THE POTENTIAL OF ROSEMARY
(ROSMARINUS OFFICINALIS L.) AS A
NATURAL ANTIOXIDANT IN THE
TECHNOLOGY OF MEAT AND MEAT
PRODUCTS
9.3.1 Bioactive Compounds of Rosemary
(Rosmarinus officinalis L.)
One of the main problems in the meat industry is the oxidation of lipids and proteins
of raw materials, the result of which is the accumulation of substances that cause the
deterioration of the taste, aroma, appearance, and nutritional value of products (Fourati
et al., 2020; Jongberg et al., 2017; Králová et al., 2015; Nawaz et al., 2022). To prevent
oxidative processes in meat and meat products, it is possible to introduce antioxidants
from natural sources into the muscles after the slaughter of animals, which also helps
to enrich the products with biologically active compounds benecial to human health
(Estévez, 2021; Ribeiro et al., 2019).
Antioxidants suppress lipid peroxidation, terminating a chain reaction; neutralize
reactive oxygen species, interrupting the chain reaction of autoxidation; prevent the
formation of peroxyl radicals, and also bind metal ions (Estévez, 2021; Ribeiro et al.,
2019). Synthetic antioxidants are widely used in the meat industry and have advantages
such as stable structure, high heat resistance, and strong antioxidant capacity, and can be
synthesized in large quantities to meet demand (Liu & Mabury, 2020; Xu et al., 2021).
However, many studies show the high toxicity of synthetic phenols and their transformation products (Alabdaly et al., 2021; Sarmah et al., 2020; Sun et al., 2019; Wang
et al., 2021; Wang et al., 2022). High doses of synthetic antioxidants can be toxic for
reproductive function and development, have teratogenic and carcinogenic effects, and
caused various endocrine disorders.
252 Wild Edible Plants
FIGURE 9.1 Rosemary (Rosmarinus officinalis L.) stems with leaves (a) and rosemary
extract in form of dry powder (b).
In this regard, it is necessary to search for alternative compounds with high antioxidant properties of natural origin (Stabnikova et al., 2024). Many natural antioxidants
inhibit the development of free radicals and prevent interaction with active forms
of oxygen. Their antioxidant activity is determined by their molecular structure, the
presence of hydroxyl groups that increase the antioxidant activity of natural components.
Wild plants can be a powerful source of natural antioxidants, including rosemary and its
derivatives (Stabnikova et al., 2021).
Rosemary (Rosmarinus ofcinalis L.) belongs to the mint family Lamiaceae,
originates from the Mediterranean and has many nutritional and medicinal benets
(Figure 9.1a). Rosemary leaf extract (Figure 9.1b) has gained popularity as an important
factor in human nutrition, many studies have also proven its therapeutic effect due to the
variety of biologically active substances in its composition (Ahmed & Babakir- Mina,
2020; Moore et al., 2016).
The main polyphenols found in rosemary extract include diterpenes (carnosic and
rosmarinic acids, carnosol) (Olah et al., 2016) and triterpenes (ursolic and oleanolic
acids) (Elansary et al., 2020). Polyphenols such as caffeic acid derivatives (rosmarinic
acid), avonoids (hesperidin, luteolin) were detected in rosemary leaves using highperformance liquid chromatography (Jordan et al., 2013). The total polyphenol content
in rosemary is 2.19 mg gallic acid equivalent (GAE)/ g fresh weight (FW) or 1.71 mg
GAE/ 100 g dry weight (DW) (Zheng & Wang, 2001) (Table 9.1).
The phenolic components present in rosemary determine its antioxidant efciency
(Table 9.1). The content of rosmarinic acid in rosemary leaves ranges from 116 to 367
mg/ 100 g DW (Zheng & Wang, 2001). The content of caffeic acid in rosemary is 12.45–
406 µg/ 100 g DW; ferulic acid is 19– 1081.5 mg/ 100 g DW; luteolin is 5.52– 616 mg/ 100
g DW, and apigenin is 6, 11– 43.8 mg/ 100 g DW (Lešnik et al., 2021; Nieto et al., 2018).
Rosemary extract contains such groups of polyphenolic compounds as phenolic
terpenes, avonoids and phenolic acids (Table 9.2).
Antioxidants from Wild Plants in Meat and Meat Products 253
TABLE 9.1 The content of bioactive compounds in rosemary dry leaves
PHYTOCHEMICALS CONTENT REFERENCES
Total polyphenolic compounds 219.00 mg GAE/ 100 g (Zheng & Wang, 2001)
168.92 mg GAE/ 100 g (Peixoto et al., 2021)
Polyphenols
Carnosic acid 292.54 mg/ 100g (Sharma et al., 2020)
Carnosol 2200.00 mg/ 100 g (Sharma et al., 2020)
Rosmanol 124.10 mg/ 100 g (Zheng & Wang, 2001)
Phenolic acids
Caffeic acid 405.50 mg/ 100 g (Sharma et al., 2020)
2.08 mg/ 100 g (Zheng & Wang, 2001)
Rosmarinic acid 3349.00 mg/ 100 g (Sharma et al., 2020)
123.90 mg/ 100 g (Zheng & Wang, 2001)
32.80 mg/ 100 g (Erkan et al., 2008)
Ursolic acid 514.43 mg/ 100 g (Sharma et al., 2020)
Flavonoids
Luteolin 21.00 mg/ 100 g (Sharma et al., 2020)
Gallocatechin 16.25 mg/ 100 g (Peixoto et al., 2021)
Flavanones
Naringin 55.05 mg/ 100 g (Erkan et al., 2008)
Apigenin 0.55 mg/ 100 g (Zheng & Wang, 2001)
Cirsimaritin 16.20 mg/ 100 g (Zheng & Wang, 2001)
43.60 mg/ 100 g (Peixoto et al., 2021)
Hispidulin 10.85 mg/ 100 g (Zheng & Wang, 2001)
TABLE 9.2 The content of bioactive compounds in rosemary extract (dry powder)
PHYTOCHEMICALS CONTENT REFERENCE
Total polyphenolic
compounds
7415– 14663 mg GAE/ 100 g (Bourhia et al., 2019)
166.32 mg GAE/ 100 g (Mena et al., 2016)
Polyphenols
Carnosic acid 11700– 17300 mg/ 100 g (Bourhia et al., 2019)
Carnosol 1090– 3000 mg/ 100 g (Bourhia et al., 2019)
2889 mg/ 100 g (Mena et al., 2016)
Rosmanol 150.0 mg/ 100 g (Mena et al., 2016)
Phenolic acids
Caffeic acid 12.45– 406.00 mg/ 100 g (Nieto et al., 2018)
9.67 mg/ 100 g (Proestos & Komaitis, 2006)
93.22 mg/ 100 g (Waller et al., 2017)
(continued)
254 Wild Edible Plants
TABLE 9.2 (Continued)
PHYTOCHEMICALS CONTENT REFERENCE
Rosmarinic acid 116– 367 mg/ 100 g (Erkan et al., 2008)
987.20 mg/ 100 g (Kivilompolo et al., 2007)
111.75 mg/ 100 g (Christopoulou et al., 2021)
Flavonoids
Luteolin 3.00 mg/ 100 g (Sharma et al., 2020)
5.02 mg/ 100 g (Christopoulou et al., 2021)
39.0 mg/ 100 g (Waller et al., 2017)
(+ )- catechin 2.70 mg/ 100 g (Proestos & Komaitis, 2006)
Gallocatechin 163.77 mg/ 100 g (Christopoulou et al., 2021)
Quercetin 30 mg/ 100 g (Waller et al., 2017)
Flavanones
Apigenin 6.11– 43.80 mg/ 100 g (Lešnik et al., 2021)
55.0 mg/ 100 g (Mena et al., 2016)
Hispidulin 26.0 mg/ 100 g (Mena et al., 2016)
It has been found that the most powerful antioxidant compounds are phenolic
diterpenes, namely carnosic acid and carnosol, which account for 90% of the antioxidant activity of rosemary extract. In addition, rosmanol, epirosmanol, iso- rosmanol,
rosmadial, rosmaridiphenol, and rosmariquinone have been identied in rosemary
extract, which also have some antioxidant functions (Senanayake, 2018).
Flavonoids present in rosemary extract include avones and avonols such as
apigenin, genquanine, luteolin, hispidulin, rutin, kaempferol, naringin, hesperetin,
apigenin- 7- O- glucoside, and quercetin, among others. Phenolic acids found in rosemary extract include rosmarinic acid, caffeic acid, chlorogenic acid, coumarinic acid,
p- coumaric acid, ferulic acid, vanillic acid, syringic acid, homovanillic acid, and phydroxybenzoic acid and many others (Jeevalatha et al., 2022).
It is known that the phenolic composition of rosemary, as well as the extracts
obtained from it, varies greatly depending on the agronomic and processing conditions
(Mena et al., 2016; Proestos & Komaitis, 2006). The identication process is based on
the fact that the phenolic fraction of each product has its own biochemical characteristics
and various derivatives. In addition, the properties of the volatile fraction of rosemary
extracts should also be evaluated, which may affect the overall composition of biologically active compounds of both rosemary and extracts.
9.3.2 The Benets of Rosemary officinalis for
Human Health and the Food Industry
In recent years, the antioxidant potential of Rosmarinus ofcinalis and its bioactive
components has been thoroughly studied both in vitro and in vivo. The versatility of
its therapeutic action and the effectiveness of its use in food technologies have been
revealed.
Antioxidants from Wild Plants in Meat and Meat Products 255
It has proven that the antitumor effect of rosemary is related to various mechanisms,
such as antioxidant and antiangiogenic properties, epigenetic effects, regulation of the
immune response and anti- inammatory response, modication of specic metabolic
pathways and increased expression of tumor suppressor genes (Ahamad et al., 2019;
Allegra et al., 2020; Eid et al., 2022). The anti- inammatory activity of rosemary, which
supports its ethnopharmacological use in diseases related to inammation and its potential use in the future, was also conrmed (Borges et al., 2019; Gonçalves et al., 2022).
The antioxidant and antimicrobial effectiveness of rosemary extracts was related
to their specic phenolic composition. Carnosic and rosmarinic acids may be the main
bioactive antimicrobial compounds present in rosemary extracts. From a practical point
of view, rosemary extract can be an effective ingredient for functional food products as
well as pharmaceutical herbal products. The use of rosemary extract as a substitute for
synthetic antioxidants is noted as one of the modern trends in the application of plant
additives for food production (Stabnikova et al., 2021).
The high antioxidant efciency of rosemary and its derivatives incorporated in
various meat and poultry products was shown (Al- Hijazeen, 2021; Kaur et al., 2023).
Rosemary extract played the role of effective antioxidant in mechanically deboned
turkey meat (Bak et al., 2020), raw ground beef and pork alone and in combination with
ascorbic acid (Borella et al., 2019; Perlo et al., 2018), of pork patties (Hwang et al.,
2017), ground beef (Horbańczuk et al., 2019), in semi- smoked duck sausages (Bozhko
et al., 2017, 2020), and in meat- containing breads (Bozhko et al., 2019). Rosemary
essential oil or its extract were more effective than butylated hydroxyanisole during the
refrigerated storage of cooked and smoked pork sausages (Lorenzo et al., 2021).
The effect of rosemary extract on the quality and stability of minced chicken was
investigated (Al- Hijazeen & Al- Rawashdeh, 2017). Rosemary extract demonstrated the
highest signicant effect on inhibiting the formation of carbonyl compounds due to
secondary oxidation of lipids. A positive effect on the sensory properties of meat was
also noted. Furthermore, rosemary extract was found to be a more effective antioxidant
compared to other commercial antioxidants. Similar results were obtained by Gao et al.
(2019). Enhanced antioxidant effect in chicken meat during storage was observed when
rosemary extract was combined with oregano essential oil (Al- Hijazeen, 2021).
The positive effect of rosemary (Rosmarinus ofcinalis L.) preparations on the
microbial quality and oxidative stability in vacuum- packed poultry meat of mechanically deboned chicken, which was stored at – 18°C for 4 months, was shown (HaćSzymańczuk et al., 2017). The authors used poultry meat to which rosemary was added
in the form of dried spices (2.0%), extracts (2.0%), and essential oil (0.2%). The control
sample did not contain rosemary. According to the results, the total number of bacteria
was signicantly lower in samples with rosemary preparations. The essential oil proved
to be the most effective in inhibiting the growth of psychrotrophic bacteria in vacuumpacked mechanically deboned poultry meat during storage. Mechanically deboned
poultry meat experimental samples also showed a signicant reduction in lipid oxidation compared to the control sample.
Another study (Paglarini et al., 2023) evaluated the effect of plant extracts,
including rosemary as a natural antioxidant, in chilled mechanically deboned poultry.
Rosemary extract was found to show a high positive effect in retarding lipid oxidation
in mechanically deboned poultry meat. pH values decreased with increasing extract
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