Next Article in Journal
Application of Rice Husk-Derived SBA-15 Bifunctionalized with C18 and Sulfonic Groups for Solid-Phase Extraction of Tropane, Pyrrolizidine, and Opium Alkaloids in Gluten-Free Bread
Next Article in Special Issue
Designing Plant-Based Foods: Biopolymer Gelation for Enhanced Texture and Functionality
Previous Article in Journal
Impact of Harvest Periods on the Physicochemical and Flavour Characteristics of Sichuan Pepper (Zanthoxylum bungeanum Maxim)
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Foods
Volume 14
Issue 7
10.3390/foods14071154
foods-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

A Comprehensive Polyphenolic Characterization of Five Montmorency Tart Cherry (Prunus cerasus L.) Product Formulations

by
Muhammad Jawad
1,
Stephen T. Talcott
2,
Angela R. Hillman
3 and
Robert G. Brannan
4,*
1
Department of Translational Biomedical Sciences, Ohio University, Athens, OH 45701, USA
2
Department of Food Science & Technology, Texas A&M University, College Station, TX 77845, USA
3
Department of Exercise Physiology, Ohio University, Athens, OH 45701, USA
4
Department of Food and Nutrition Sciences, Ohio University, Athens, OH 45701, USA
*
Author to whom correspondence should be addressed.
Foods 2025, 14(7), 1154; https://doi.org/10.3390/foods14071154
Submission received: 11 March 2025 / Revised: 24 March 2025 / Accepted: 25 March 2025 / Published: 26 March 2025
(This article belongs to the Special Issue Plant-Based Functional Foods and Innovative Production Technologies)
Versions Notes

Abstract

:
The Montmorency tart cherry (Prunus cerasus L., MTC) polyphenols may contribute to reduced inflammation and oxidative stress biomarkers in the body. However, a comprehensive polyphenolic profile of MTC products is lacking. This study provides a comparative analysis of the polyphenolic distribution of individual anthocyanins, flavonols, flavanols, hydroxycinnamic acids, and hydroxybenzoic acids in five MTC products (frozen raw fruit, freeze-dried powder, sweet dried fruit, unsweetened dried fruit, juice concentrate). Twenty-three polyphenols were detected, and 21 were positively identified. Results from three replicates indicate that frozen raw MTC has the most total polyphenolics. Juice concentrate, unsweetened dried MTC, freeze-dried MTC powder, and sweet dried MTC contained 26%, 40%, 60%, and 77% fewer total polyphenolics than frozen raw MTC. Hydroxycinnamic acids, flavonols, and anthocyanins predominated, accounting for 87–99% of total polyphenols in MTC products. Chlorogenic acid, rutin, cyanidin-3-sophoroside, feruloquinic acid, ferulic acid, and coumaric acid isomers were noteworthy polyphenolics. Hydroxycinnamic acids predominated in sweet dried (82%), unsweetened dried (74%), juice concentrate (66%), and frozen-raw (54%) MTC. Flavonols predominated in freeze-dried MTC powder (52%). Anthocyanins, particularly cyanidin glycosides, were important polyphenolics in frozen-raw cherries (18%) but less so in other MTC products. These findings highlight the variability in polyphenols in MTC products and emphasize the importance of selecting appropriate MTC products for specific health benefits.

1. Introduction

Polyphenols are naturally occurring bioactive compounds found in plants and plant-based foods, recognized for their potential health benefits, particularly their antioxidative and anti-inflammatory properties. They comprise multiple phenolic structures with hydroxyl groups (-OH) attached to their termini. Polyphenols are crucial in plant defense mechanisms, growth, and development [1,2]. Scientific interest in polyphenols has significantly increased over the past two decades [3].
Studies on the health-promoting effects of polyphenols have established their role in neutralizing free radicals and reducing pro-inflammatory mediators in the body [4]. Among polyphenol-rich fruits, Montmorency tart cherries (Prunus cerasus L., MTC) are notable for their rich total polyphenolic content [5], compounds linked to the reduction in oxidative stress and inflammation in the body [6,7,8,9,10]. Research data suggest that regular consumption of MTC may aid in mitigating symptoms of chronic diseases, such as osteoarthritis [11] and cardiovascular diseases [12,13,14,15], by targeting pathways that regulate inflammatory and oxidative responses [16,17].
In MTC, anthocyanins and phenolic acids [18,19] are the predominant polyphenols, and these compounds and research report their benefits in reducing biomarkers of inflammation and oxidative stress, as well as supporting muscle recovery [20,21,22]. Several studies have examined the effects of individual MTC products on health outcomes; for instance, reductions in exercise-induced muscle soreness and inflammation following consumption of MTC juice [23] and enhanced recovery and reduced muscle damage markers among athletes using MTC freeze-dried powder [24] have been reported.
Despite these benefits, the polyphenolic profiles across MTC products are often incomplete, focusing on specific polyphenolic compounds or subclasses, particularly anthocyanins [18,19,25]. Further, processing methods such as heating [26,27,28], drying [29,30,31,32], and freeze-drying [33,34,35] can alter the polyphenolic content and, consequently, the efficacy of these products. Given these factors, a comprehensive comparison of polyphenolic profiles across various MTC products is warranted because there is a paucity of direct comparisons of polyphenolic content in commercially available products. Therefore, the objective of this study was to use LC–MS-MS to determine the polyphenolic profiles of five MTC products (frozen raw fruit, juice concentrate, freeze-dried powder, dried sweetened, and dried unsweetened) available in the market, facilitating direct comparison of polyphenolic compounds to inform the selection of optimal MTC products for health-related applications.

2. Materials and Methods

2.1. Materials

Five different commercially available MTC products (frozen raw fruit, freeze-dried powder, sweet dried, unsweetened dried, and juice concentrate) were procured from King Orchards, Central Lake, MI, USA. All products were manufactured using proprietary processes from MTC harvested in 2022, except for the concentrate from cherries harvested in 2023. The sweet dried cherries contained 5% added sugar based on dry weight. Except for the minimal use of processing aides (<1%) in the dried products, no other ingredients were added to the products. Solvents were purchased from Thermo Fisher. External standards (catechin, chlorogenic acid, cyanidin-3-glucoside, cyanidin-3-rutinoside, (-)-epicatechin, p-coumaric acid, caffeic acid, ferulic acid, gallic acid, naringenin, procyanidin B2, protocatechuic acid, quercetin, rutin, kaempferol, melatonin, cyanidin-3-sophoroside, peonidin, and o-coumaric acid) were obtained from Phytolab, Vestenbergsgreuth, Germany or Sigma Aldrich, St. Louis, MO, USA.

2.2. Sample Extraction

To prepare the extracts for LC–MS-MS analysis, MTC frozen raw fruit, freeze-dried powder, sweet dried fruit, and unsweetened dried fruit (1 g) were each combined with methanol acidified with 0.1% formic acid (10 mL). Each mixture was thoroughly homogenized for 10 min, followed by 30 min of sonication to ensure optimal extraction. The fruit extracts were centrifuged at 12,000× g for 30 min to obtain supernatants that were filtered using 0.22 µm PTFE filters and transferred into HPLC vials for analysis. For the tart cherry juice preparation, 1 part of MTC juice concentrate was first diluted with seven parts distilled water, and the same preparation procedure followed. All prepared MTC fruit extracts were stored at −10 °C until further analysis by LC–MS–MS. Three replicates were performed.

2.3. Triple Quadrupole Liquid Chromatography–Mass Spectrophotometry (LC–MS–MS)

Analysis was conducted on a Thermo Scientific VanquishTM UHPLC equipped with a Thermo Scientific TSQ Altis triple quadrupole mass spectrometer with a HESI source (Waltham, MA, USA). The mobile phases included 0.1% formic acid in mass spectroscopic grade water (Solvent A) as the aqueous phase and 0.1% formic acid in mass spectroscopic grade methanol (Solvent B) as the organic phase. The analysis was carried out over a 10-minute run using a Waters SunFireTM C18 column (150 × 3 mm, 5 μm, Milford, MA, USA) set at 25 °C with a 1 µL injection volume and a flow rate of 0.4 mL/min. The gradient began at 95% Solvent A:5% solvent B and was run from 0 to 8 min in a linear gradient to 5% Solvent A:95% solvent B and held at 95% Solvent B for an additional 2 min prior to equilibration to initial conditions.
MS data were acquired in either negative or positive ESI using Chromeleon 7.2.10 ES software based on optimal ionization conditions of each compound. The parameters consisted of a 3913 V spray voltage, nitrogen gas as the sheath gas at 24 arbitrary units, argon as the auxiliary gas at 2 arbitrary units, ion transfer tube temperature at 325 °C, and the vaporizer temperature at 350 °C. Compound identification was accomplished by comparing retention times, ionization fragmentation patterns, and relative ion abundances with known analytical standards and through online database (www.hmdb.ca) searches. Quantification was performed using calibration curves obtained from analytical standards or in equivalence of a structurally similar standard and when an authentic standard was unavailable.

3. Results and Discussion

The polyphenolic compounds and their LC–MS–MS characteristics across the five MTC products are shown in Table 1. Twenty-one of the 23 polyphenolic compounds were identified based on retention times, molecular weights, deprotonated ion masses, and fragment ions compared to authentic standards. Two others, taxifolin and feruloquinic acid, were not able to be positively identified but were semi-quantified based on their structurally similar compounds, quercetin and ferulic acid, respectively. Taxifolin was identified with a molecular weight of m/z 303.03 in negative ion mode with fragment ions at m/z 124.97, 177.04, and 285.04. Similarly, feruloquinic acid was detected with a molecular weight of m/z 367 (m/z) in negative ion mode and fragment ions at m/z 134.04, 190.95, and 193.04.

3.1. Polyphenolics in MTC Products

The predominant polyphenolic classes in the five MTC products are shown in Table 2. Total phenolics summed across all the individual polyphenols indicate that frozen raw MTC contained the most total polyphenolics of the five MTC products. MTC juice concentrate, unsweetened dried MTC, freeze-dried MTC powder, and sweet dried MTC contained 26%, 40%, 60%, and 77% fewer total polyphenolics than the frozen raw MTC. This result suggests that processing has an impact on polyphenolic levels in MTC products, and there is evidence that polyphenols degrade during processing, especially drying [18,36,37,38]. However, this study is limited to a survey of five commercially available MTC products, so unknown factors such as genetic variability, agricultural practices, post-harvest handling and storage, and processing conditions make systematic conclusions unreliable.
All five MTC products were similar in that hydroxycinnamic acids, flavonols, and anthocyanins predominated, accounting for 87–99% of the total polyphenols in each product. Hydroxycinnamic acids were predominant in sweet dried MTC, unsweetened dried MTC, MTC juice concentrate, and frozen raw MTC, accounting for 83%, 74%, 66%, and 54% of total polyphenolics, respectively. Of the hydroxycinnamic acids, chlorogenic acid predominated, but feruloquinic acid, ferulic acid, and coumaric acid isomers were notable in certain MTC products (Table 3). Although freeze-dried cherry powder contained 29% hydroxycinnamic acids, flavonols predominated and accounted for 52% of total polyphenolics. Flavonols accounted for 12–19% of the other four MTC products, and rutin (quercetin-3-O-rutinoside) was the predominant flavonol in all MTC products. Anthocyanins, particularly cyanidin glycosides, were important polyphenolic compounds in frozen raw cherries, where they accounted for 18% of total polyphenolics, but less so in the other four MTC products, where they accounted for 4–6% of total polyphenolics.

3.1.1. Hydroxycinnamic Acids

Seven hydroxycinnamic acids and their glycosides were detected in the MTC products (Table 1), and although the identity of feruloquinic acid could not be confirmed because it was not compared to an authentic standard, spectroscopic clues lent confidence to its inclusion in this discussion. Chlorogenic acid and feruloquinic acid in an approximately 3:1 ratio were the predominant hydroxycinnamic compounds in four of the MTC products, whereas chlorogenic acid, feruloquinic acid, and ferulic acid accounted for the hydroxycinnamic acids in a nearly equal 1:1:1 ratio in freeze-dried MTC powder. The two coumaric acid isomers (p- and o-) were found collectively at 8–17% of hydroxycinnamic acids in the MTC products. Caffeic acid (4%) and its glycoside did not account for more than 2% of the hydroxycinnamic acids in any MTC products except MTC juice concentrate (4% caffeic acid).
Compared to the frozen raw MTC, there were fewer hydroxycinnamic acids in the other four MTC products, especially in the sweet dried cherries (65% fewer) and freeze-dried powder (79% fewer). This result likely was due to the presence of less chlorogenic acid, feruloquinic acid, and ferulic acid in the MTC products compared to the frozen raw MTC.
Hydroxycinnamic acids, including caffeic acid, ferulic acid, chlorogenic acid, and p-coumaric acid, play an important role in neutralizing free radicals [39,40]. This action helps reduce oxidative stress and protects cells from damage associated with chronic diseases such as cardiovascular disease by preventing LDL oxidation [41], a key factor in atherosclerosis development, and enhancing blood vessel function [42]. Additionally, hydroxycinnamic acids exhibit anti-inflammatory properties by modulating inflammatory pathways, which can be beneficial for conditions like arthritis [43]. They also possess antimicrobial properties and may enhance gut health by promoting beneficial bacteria [44].

3.1.2. Flavonols

Four flavonols, also known as 3-hydroxyflavones, were identified across the five MTC products (Table 1). Rutin (quercetin-3-O-rutinoside) accounted for 95–98% of the total flavonols (Table 3) and was the predominant flavonoid in each of the MTC products regardless of flavonoid subclass. Compared to the frozen raw MTC, less rutin was identified in MTC juice concentrate (37% less), unsweetened dried MTC (40% less), and especially sweetened dried MTC (86% less). However, freeze-dried MTC was identified at the same level as frozen raw MTC. This suggests that lyophilization either exerts a protective mechanism on rutin or enhances its extractability [45,46].
Three other flavonols were detected in the MTC products. Small amounts of either quercetin or its glucoside were identified in each MTC product; however, the amounts that were identified were very near to the lower detection limit of the assay and together accounted for 2.0%, 0.5%, 0.5%, 0.4%, and 0.2% of all flavonoids in freeze-dried, juice concentrate, unsweetened dried, frozen raw, and sweet dried MTC, respectively. While the presence of free quercetin in tart cherry has been reported in the literature [18,47], it is also possible that its detection may result from enzymatic or other degradation of quercetin 3-glucoside. Kaempferol-3-rutinoside was detected in very small amounts in all MTC products and accounted for 0.1–0.5% of all flavonoids in the MTC products.
Flavonols are well-recognized for their ability to mitigate oxidative stress, which may help decrease the risk of chronic diseases such as cardiovascular disease [48,49] and cancer [50,51]. Rutin is a potential natural senomorphic agent with therapeutic potential for age-related diseases, including cancer [52,53], reducing inflammation [54], increasing antioxidant capacity [55], and improving gut morphology and gut microflora [56]. Rutin and quercetin have also demonstrated preventive effects against DXR-induced hepatotoxicity via inhibiting inflammation, oxidative stress, and apoptosis with attenuating Nrf2 expression in rats [57]. Quercetin is found to be associated with improved cardiovascular health by reducing blood pressure [58,59,60] and inhibiting platelet aggression [61,62]. Similarly, kaempferol has shown potential in reducing oxidative damage [63,64] and inflammation [64,65], making it a viable agent for antioxidative and anti-inflammatory therapies.
MTC products emphasize how processing methods can affect flavonol compounds. Some products contain substantial levels of flavonol compounds, while others, like frozen raw fruit and sweet dried cherries, may have concentrations below detectable thresholds. This may suggest that concentrating or drying MTC in the absence of sugar enhances the protective effect on flavonols. The potential of sugars to promote the degradation of polyphenols, including anthocyanins and potentially flavonols, through Maillard reactions or by altering their thermal stability has been reported [66].

3.1.3. Anthocyanins

Of the five anthocyanins identified in MTC (Table 1), only the cyanidin glycosides were detected in all MTC products, but their distribution was dependent on the product. Cyanidin-3-sophoroside was the predominant anthocyanin in frozen raw MTC (65%) and sweet dried MTC (43%). Cyanidin-3-rutinoside (36%) and cyanidin-3-glucoside (21%) accounted for the remaining 57% of anthocyanins in sweet dried MTC, whereas the remaining anthocyanins in raw frozen MTC were distributed evenly between the cyanidin glycosides (17%) and peonidin-3-rutinoside (17%). Cyanidin-3-rutinoside predominated in unsweetened dried MTC, juice concentrate, and freeze-dried MTC powder (59%, 52%, and 42%, respectively), and these products also contained considerable cyanidin-3-glucoside (34%, 31%, 25%). The presence of peonidin and its rutinoside was variable in these three MTC products. Unsweetened dried MTC contained only cyanidin glycosides, MTC juice concentrate contained peonidin-3-rutinoside (10%), and freeze-dried MTC powder contained 10% peonidin-3-rutinoside (15%) and was the only anthocyanidin that contained peonidin aglycone (4%).
Anthocyanins play an important role in reducing oxidative stress, which may help lower the risk of cardiovascular diseases by improving blood vessel flexibility [67,68] and reducing hypertension [13]. Additionally, anthocyanins possess anti-inflammatory properties that are particularly beneficial for managing osteoarthritis [69,70,71], as they can help reduce inflammation and alleviate pain. Emerging research also indicates that anthocyanins support brain health by protecting neurons from oxidative damage, potentially enhancing cognitive function, and decreasing the risk of neurodegenerative diseases [72].

3.1.4. Flavanols (Flavan-3-ols)

Four flavan-3-ols were identified in the five MTC products (Table 1), and although the identity of taxifolin could not be confirmed because it was not compared to an authentic standard, spectroscopic clues lent confidence to its inclusion in this discussion. Taxifolin, which has the basic structure of a flavan-3-ol with a ketone at the 4-position of its C-ring, is sometimes considered to be in the flavonoid/flavan-3-ol subclass of flavanonols; however, herein, it is considered together with the flavan-3-ols. Overall, flavan-3-ols account for only a fraction of total polyphenolics in the frozen raw MTC (7%), MTC juice concentrate (11%), and freeze-dried MTC powder (2%). The amount and distribution of (-)-epicatechin, catechin, and procyanidin B2 were nearly identical in frozen raw and juice concentrate MTCs, and both MTC products contained minimal (1–2%) taxifolin. The distribution of these flavan-3-ols was similar in freeze-dried MTC powder; however, it contained 15-fold less (-)-epicatechin, 18-fold less catechin, and 29-fold less procyanidin B2. There were almost no flavan-3-ols (0.1%) detected in both the unsweetened and sweetened dried MTC, a result that has been previously reported [73].
The absence of larger procyanidin polymers in the MTC products is noteworthy and aligns with the previous study on tart cherries, which reported that tart cherries predominantly contain short-chain procyanidins, with an average polymerization degree of four monomer units and lack the high concentrations of long-chain procyanidins observed in other cherry species [74]. Although targeted LC–MS-MS did not detect significant amounts of larger flavan-3-ol polymers in MTC products, it is possible that these compounds exist in higher concentrations but are bound to proteins or anthocyanins. This binding may form high-molecular-weight complexes that are difficult to extract and analyze. Previous studies have shown that flavan-3-ols can interact with proteins and anthocyanins, leading to the formation of new polymeric species that require advanced fractionation techniques for detection [75,76,77].
After ingestion, flavan-3-ols undergo metabolic transformations, with secondary metabolites subsequently detected in blood plasma, where they have the potential to exert systemic health effects. Research has demonstrated that catechin and (-)-epicatechin support cardiovascular health by enhancing endothelial function and reducing blood pressure, attributable to their vasodilatory and anti-inflammatory properties [78,79]. Procyanidin B2, although present in lower concentrations, exhibits potent antioxidant effects, particularly in mitigating oxidative stress, and is associated with benefits for skin [80,81] and vascular health through its role in neutralizing free radicals [82,83]. Collectively, these polyphenols contribute to decreased oxidative stress and inflammatory markers, supporting their role in the management of inflammatory conditions when consumed regularly.

3.1.5. Flavanones

Naringenin is the lone flavanone detected in the MTC products (Table 1) and only accounted for only 3% of polyphenolics in freeze-dried MTC powder and less than 1% in the other MTC products. Research has shown that naringenin can reduce oxidative stress by neutralizing free radicals, which helps protect cells from damage associated with aging and various chronic diseases [84,85]. Additionally, studies also suggest that naringenin may improve cardiovascular health by improving lipid levels [86,87] and alleviating arthritis symptoms [88,89]. Moreover, naringenin plays a significant role in inhibiting the growth of breast [90,91] and prostate cancer cells [92] through processes such as cell apoptosis and regulation of the cell cycle.

3.1.6. Hydroxybenzoic Acids

Gallic acid and protocatechuic acid were the hydroxybenzoic acids detected and quantified in the MTC products (Table 1); however, only freeze-dried MTC powder contained hydroxybenzoic acids at a substantial level (8%). The amount of hydroxybenzoic acids in the other MTC formulations was 1% or less. In freeze-dried MTC powder, the gallic acid to protocatechuic acid ratio was 10:1. It is not clear from these data if the lack of hydroxybenzoic acids in the MTC products that were not freeze-dried was due to natural variation or some other cause. Hydroxybenzoic acids are known as antioxidants that can neutralize free radicals, reduce oxidative stress, and prevent cellular damage. Gallic acid has demonstrated anti-inflammatory effects [93], which contribute to its ability to reduce inflammation and the risk of cardiovascular diseases [94]. Protocatechuic acid is associated with neuroprotective effects, helping to prevent neurodegenerative diseases by shielding neuronal cells from oxidative stress [95].

3.2. Summary

The polyphenolic profiling presented in this study offers a more comprehensive analysis of the array of polyphenols in MTC products compared to previous research, which is often limited to specific polyphenolic compounds or classes [18,19,25]. For example, Kim et al. (2005) focused on phenolic content and anthocyanin stability in sweet and sour cherry cultivars but limited the analysis to a few major compounds, particularly cyanidin-3-glucoside [25]. Kirakosyan et al. (2009) analyzed similar products to those of the current study but focused on anthocyanins and a few other selected flavonoids without in-depth polyphenol quantification across the products [18]. Ou et al. (2012) explored polyphenols in several forms and emphasized anthocyanins, procyanidins, and antioxidant capacity without covering the full array of individual polyphenols [19].
In contrast, this study evaluated five distinct MTC products (frozen raw fruit, freeze-dried powder, sweet dried fruit, unsweetened dried fruit, and juice concentrate) and provided an extensive comparative analysis of polyphenolic distribution that includes anthocyanins, flavonols, flavanols, hydroxycinnamic acids, and hydroxybenzoic acids. The analysis confirms the presence of commonly studied compounds, such as the cyanidin derivatives, and quantifies lesser-examined components like caffeic acid glycoside and peonidin-3-rutinoside.
Specifically, twenty-three polyphenols were detected, and 21 were positively identified, and the results show that frozen raw MTC has the most total polyphenolics. Juice concentrate, unsweetened dried MTC, freeze-dried MTC powder, and sweet dried MTC contained 26%, 40%, 60%, and 77% fewer total polyphenolics than the frozen raw MTC. Hydroxycinnamic acids, flavonols, and anthocyanins predominated, accounting for 87–99% of total polyphenols in MTC products. Chlorogenic acid, rutin, cyanidin-3-sophoroside, feruloquinic acid, ferulic acid, and coumaric acid isomers were the noteworthy individual polyphenolics. Hydroxycinnamic acids predominated in sweet dried MTC (82%), unsweetened dried MTC (74%), juice concentrate (66%), and frozen-raw (54%) MTC, and flavonols predominated in freeze-dried MTC powder (52%). Anthocyanins, particularly cyanidin glycosides, were important polyphenolics in frozen raw cherries (18%) but less so in other MTC products.

4. Conclusions

This comprehensive polyphenolic profiling of MTC products offers insights that impact the practical and theoretical understanding of these commercial items. Practically, fewer total polyphenolics were observed in processed forms compared to frozen raw MTC, which underscores the importance of processing methods in preserving these compounds. These data allow consumers and manufacturers to make informed decisions regarding product selection and processing techniques, potentially favoring less processed options to maximize polyphenol intake. Theoretically, this work differs from prior work that often focused on limited subsets of polyphenols and revealed that frozen raw MTC exhibited the highest total polyphenolic content. The quantification of less frequently examined compounds, such as caffeic acid glycoside and peonidin-3-rutinoside, alongside the confirmation of more commonly studied cyanidin derivatives, offers the possibility of a more detailed understanding of the polyphenolic profile in MTC. This foundation can be used as justification for clinical trials with MTC polyphenol-rich products to establish their health benefits and bioavailability, which would help to understand how well MTC polyphenols are metabolized and absorbed in the body to demonstrate their beneficial effects.

Author Contributions

Conceptualization, A.R.H. and R.G.B.; methodology, M.J., S.T.T. and R.G.B.; analysis, M.J. and S.T.T.; writing—original draft preparation, M.J., R.G.B. and A.R.H.; writing—review and editing, M.J., R.G.B., S.T.T. and A.R.H.; visualization, M.J., R.G.B. and A.R.H. All authors have read and agreed to the published version of the manuscript.

Funding

Funding was provided by the “Ohio University Kopchick Research Fellowship for TBS/MCB Research for the Academic Year of 2023–2024”.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The original contributions presented in the study are included in the article, further inquiries can be directed to the corresponding author.

Conflicts of Interest

The authors declare no conflicts of interest.

References

  1. Tanase, C.; Bujor, O.-C.; Popa, V.I. Chapter 3—Phenolic Natural Compounds and Their Influence on Physiological Processes in Plants. In Polyphenols in Plants, 2nd ed.; Watson, R.R., Ed.; Academic Press: Cambridge, MA, USA, 2019; pp. 45–58. [Google Scholar]
  2. Tuladhar, P.; Sasidharan, S.; Saudagar, P. 17—Role of phenols and polyphenols in plant defense response to biotic and abiotic stresses. In Biocontrol Agents and Secondary Metabolites; Jogaiah, S., Ed.; Woodhead Publishing: Sawston, UK, 2021; pp. 419–441. [Google Scholar]
  3. Bertelli, A.; Biagi, M.; Corsini, M.; Baini, G.; Cappellucci, G.; Miraldi, E. Polyphenols: From Theory to Practice. Foods 2021, 10, 2595. [Google Scholar] [CrossRef] [PubMed]
  4. Zhang, H.; Tsao, R. Dietary polyphenols, oxidative stress and antioxidant and anti-inflammatory effects. Curr. Opin. Food Sci. 2016, 8, 33–42. [Google Scholar] [CrossRef]
  5. Rothwell, J.A.; Pérez-Jiménez, J.; Neveu, V.; Medina-Remón, A.; M’Hiri, N.; García-Lobato, P.; Manach, C.; Knox, C.; Eisner, R.; Wishart, D.S.; et al. Phenol-Explorer 3.0: A major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database J. Biol. Databases Curation 2013, 2013, bat070. [Google Scholar] [CrossRef]
  6. Bell, P.G.; Gaze, D.C.; Davison, G.W.; George, T.W.; Scotter, M.J.; Howatson, G. Montmorency tart cherry (Prunus cerasus L.) concentrate lowers uric acid, independent of plasma cyanidin-3-O-glucosiderutinoside. J. Funct. Foods 2014, 11, 82–90. [Google Scholar] [CrossRef]
  7. Chai, S.C.; Davis, K.; Zhang, Z.; Zha, L.; Kirschner, K.F. Effects of Tart Cherry Juice on Biomarkers of Inflammation and Oxidative Stress in Older Adults. Nutrients 2019, 11, 228. [Google Scholar] [CrossRef]
  8. Martinelli, I.; Tomassoni, D.; Bellitto, V.; Roy, P.; Di Bonaventura, M.V.M.; Amenta, F.; Amantini, C.; Cifani, C.; Tayebati, S.K. Anti-Inflammatory and Antioxidant Properties of Tart Cherry Consumption in the Heart of Obese Rats. Biology 2022, 11, 646. [Google Scholar] [CrossRef] [PubMed]
  9. Shukitt-Hale, B.; Kelly, M.E.; Bielinski, D.F.; Fisher, D.R. Tart Cherry Extracts Reduce Inflammatory and Oxidative Stress Signaling in Microglial Cells. Antioxidants 2016, 5, 33. [Google Scholar] [CrossRef]
  10. Traustadóttir, T.; Davies, S.S.; Stock, A.A.; Su, Y.; Heward, C.B.; Roberts, L.J., II; Harman, S.M. Tart Cherry Juice Decreases Oxidative Stress in Healthy Older Men and Women. J. Nutr. 2009, 139, 1896–1900. [Google Scholar] [CrossRef]
  11. Schumacher, H.; Pullman-Mooar, S.; Gupta, S.; Dinnella, J.; Kim, R.; McHugh, M. Randomized double-blind crossover study of the efficacy of a tart cherry juice blend in treatment of osteoarthritis (OA) of the knee. Osteoarthr. Cartil. 2013, 21, 1035–1041. [Google Scholar] [CrossRef]
  12. Keane, K.M.; Bell, P.G.; Lodge, J.K.; Constantinou, C.L.; Jenkinson, S.E.; Bass, R.; Howatson, G. Phytochemical uptake following human consumption of Montmorency tart cherry (L. Prunus cerasus) and influence of phenolic acids on vascular smooth muscle cells in vitro. Eur. J. Nutr. 2016, 55, 1695–1705. [Google Scholar] [CrossRef]
  13. Keane, K.M.; George, T.W.; Constantinou, C.L.; Brown, M.A.; Clifford, T.; Howatson, G. Effects of Montmorency tart cherry (Prunus cerasus L.) consumption on vascular function in men with early hypertension. Am. J. Clin. Nutr. 2016, 103, 1531–1539. [Google Scholar] [CrossRef] [PubMed]
  14. Kimble, R.; Keane, K.M.; Lodge, J.K.; Howatson, G. The Influence of Tart Cherry (Prunus cerasus, cv Montmorency) Concentrate Supplementation for 3 Months on Cardiometabolic Risk Factors in Middle-Aged Adults: A Randomised, Placebo-Controlled Trial. Nutrients 2021, 13, 1417. [Google Scholar] [CrossRef] [PubMed]
  15. Moosavian, S.P.; Maharat, M.; Chambari, M.; Moradi, F.; Rahimlou, M. Effects of tart cherry juice consumption on cardio-metabolic risk factors: A systematic review and meta-analysis of randomized-controlled trials. Complement. Ther. Med. 2022, 71, 102883. [Google Scholar] [CrossRef]
  16. Kelley, D.S.; Adkins, Y.; Laugero, K.D. A Review of the Health Benefits of Cherries. Nutrients 2018, 10, 368. [Google Scholar] [CrossRef] [PubMed]
  17. Sabou, V.R.; O’Leary, M.F.; Liu, Y.; Brown, P.N.; Murch, S.; Bowtell, J.L. Review of Analytical Methods and Reporting of the Polyphenol Content of Tart Cherry Supplements in Human Supplementation Studies Investigating Health and Exercise Performance Effects: Recommendations for Good Practice. Front. Nutr. 2021, 8, 652094. [Google Scholar] [CrossRef]
  18. Kirakosyan, A.; Seymour, E.M.; Urcuyo Llanes, D.E.; Kaufman, P.B.; Bolling, S.F. Chemical profile and antioxidant capacities of tart cherry products. Food Chem. 2009, 115, 20–25. [Google Scholar] [CrossRef]
  19. Ou, B.; Bosak, K.N.; Brickner, P.R.; Iezzoni, D.G.; Seymour, E.M. Processed Tart Cherry Products—Comparative Phytochemical Content, in vitro Antioxidant Capacity and in vitro Anti-inflammatory Activity. J. Food Sci. 2012, 77, H105–H112. [Google Scholar] [CrossRef]
  20. Brown, M.A.; Stevenson, E.J.; Howatson, G. Montmorency tart cherry (Prunus cerasus L.) supplementation accelerates recovery from exercise-induced muscle damage in females. Eur. J. Sport Sci. 2019, 19, 95–102. [Google Scholar] [CrossRef] [PubMed]
  21. Hooper, D.R.; Orange, T.; Gruber, M.T.; Darakjian, A.A.; Conway, K.L.; Hausenblas, H.A. Broad Spectrum Polyphenol Supplementation from Tart Cherry Extract on Markers of Recovery from Intense Resistance Exercise. J. Int. Soc. Sports Nutr. 2021, 18, 47. [Google Scholar] [CrossRef]
  22. Wangdi, J.T.; O’leary, M.F.; Kelly, V.G.; Jackman, S.R.; Tang, J.C.Y.; Dutton, J.; Bowtell, J.L. Tart Cherry Supplement Enhances Skeletal Muscle Glutathione Peroxidase Expression and Functional Recovery after Muscle Damage. Med. Sci. Sports Exerc. 2022, 54, 609–621. [Google Scholar] [CrossRef]
  23. Bell, P.G.; Stevenson, E.; Davison, G.W.; Howatson, G. The Effects of Montmorency Tart Cherry Concentrate Supplementation on Recovery Following Prolonged, Intermittent Exercise. Nutrients 2016, 8, 441. [Google Scholar] [CrossRef]
  24. Levers, K.; Dalton, R.; Galvan, E.; O’Connor, A.; Goodenough, C.; Simbo, S.; Mertens-Talcott, S.U.; Rasmussen, C.; Greenwood, M.; Riechman, S.; et al. Effects of powdered Montmorency tart cherry supplementation on acute endurance exercise performance in aerobically trained individuals. J. Int. Soc. Sports Nutr. 2016, 13, 22. [Google Scholar] [CrossRef] [PubMed]
  25. Kim, D.-O.; Heo, H.J.; Kim, Y.J.; Yang, H.S.; Lee, C.Y. Sweet and Sour Cherry Phenolics and Their Protective Effects on Neuronal Cells. J. Agric. Food Chem. 2005, 53, 9921–9927. [Google Scholar] [CrossRef]
  26. Aguilar-Rosas, S.; Ballinas-Casarrubias, M.; Nevarez-Moorillon, G.; Martin-Belloso, O.; Ortega-Rivas, E. Thermal and pulsed electric fields pasteurization of apple juice: Effects on physicochemical properties and flavour compounds. J. Food Eng. 2007, 83, 41–46. [Google Scholar] [CrossRef]
  27. Andlauer, W.; Stumpf, C.; Hubert, M.; Rings, A.; Fürst, P. Influence of cooking process on phenolic marker compounds of vegetables. Int. J. Vitam. Nutr. Res. 2003, 73, 152–159. [Google Scholar] [CrossRef] [PubMed]
  28. Makris, D.P.; Rossiter, J.T. Domestic processing of onion bulbs (Allium cepa) and asparagus spears (Asparagus officinalis): Effect on flavonol content and antioxidant status. J. Agric. Food Chem. 2001, 49, 3216–3222. [Google Scholar] [CrossRef]
  29. Alean, J.; Chejne, F.; Rojano, B. Degradation of polyphenols during the cocoa drying process. J. Food Eng. 2016, 189, 99–105. [Google Scholar] [CrossRef]
  30. Aydin, E.; Gocmen, D. The influences of drying method and metabisulfite pre-treatment on the color, functional properties and phenolic acids contents and bioaccessibility of pumpkin flour. LWT—Food Sci. Technol. 2015, 60, 385–392. [Google Scholar] [CrossRef]
  31. Madrau, M.A.; Piscopo, A.; Sanguinetti, A.M.; Del Caro, A.; Poiana, M.; Romeo, F.V.; Piga, A. Effect of drying temperature on polyphenolic content and antioxidant activity of apricots. Eur. Food Res. Technol. 2009, 228, 441–448. [Google Scholar] [CrossRef]
  32. Wojdyło, A.; Figiel, A.; Lech, K.; Nowicka, P.; Oszmiański, J. Effect of Convective and Vacuum–Microwave Drying on the Bioactive Compounds, Color, and Antioxidant Capacity of Sour Cherries. Food Bioprocess Technol. 2014, 7, 829–841. [Google Scholar] [CrossRef]
  33. Dalmau, M.E.; Bornhorst, G.M.; Eim, V.; Rosselló, C.; Simal, S. Effects of freezing, freeze drying and convective drying on in vitro gastric digestion of apples. Food Chem. 2017, 215, 7–16. [Google Scholar] [CrossRef] [PubMed]
  34. Mullen, W.; Stewart, A.J.; Lean, M.E.J.; Gardner, P.; Duthie, G.G.; Crozier, A. Effect of Freezing and Storage on the Phenolics, Ellagitannins, Flavonoids, and Antioxidant Capacity of Red Raspberries. J. Agric. Food Chem. 2002, 50, 5197–5201. [Google Scholar] [CrossRef] [PubMed]
  35. Yanat, M.; Baysal, T. Effect of freezing rate and storage time on quality parameters of strawberry frozen in modified and home type freezer. Hrvat Časopis Prehrambenu Tehnol. Biotehnol. Nutr. 2018, 13, 154–158. [Google Scholar] [CrossRef]
  36. Chaovanalikit, A.; Wrolstad, R.E. Anthocyanin and Polyphenolic Composition of Fresh and Processed Cherries. J. Food Sci. 2004, 69, FCT73–FCT83. [Google Scholar] [CrossRef]
  37. Garcia-Viguera, C.; Zafrilla, P.; Tomás-Barberán, F.A. The use of acetone as an extraction solvent for anthocyanins from straw-berry fruit. Phytochem. Anal. 1998, 9, 274–277. [Google Scholar] [CrossRef]
  38. Wang, S.Y.; Stretch, A.W. Antioxidant capacity in cranberry is influenced by cultivar and storage temperature. J. Agric. Food Chem. 2001, 49, 969–974. [Google Scholar] [CrossRef] [PubMed]
  39. Maurya, D.K.; Devasagayam, T.P.A. Antioxidant and prooxidant nature of hydroxycinnamic acid derivatives ferulic and caffeic acids. Food Chem. Toxicol. 2010, 48, 3369–3373. [Google Scholar] [CrossRef]
  40. Olszowy-Tomczyk, M.; Typek, R. Transformation of phenolic acids during radical neutralization. J. Food Sci. Technol. 2024, 61, 790–797. [Google Scholar] [CrossRef]
  41. Lee, S.; Han, J.-M.; Kim, H.; Kim, E.; Jeong, T.-S.; Lee, W.S.; Cho, K.-H. Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA:cholesterol acyltransferase-1 and -2 activity, and decrease of HDL-particle size. Bioorganic Med. Chem. Lett. 2004, 14, 4677–4681. [Google Scholar] [CrossRef]
  42. Manach, C.; Scalbert, A.; Morand, C.; Rémésy, C.; Jiménez, L. Polyphenols: Food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727–747. [Google Scholar] [CrossRef]
  43. Neog, M.K.; Pragasam, S.J.; Krishnan, M.; Rasool, M. p-Coumaric acid, a dietary polyphenol ameliorates inflammation and curtails cartilage and bone erosion in the rheumatoid arthritis rat model. BioFactors 2017, 43, 698–717. [Google Scholar] [CrossRef]
  44. Leonard, W.; Zhang, P.; Ying, D.; Fang, Z. Hydroxycinnamic acids on gut microbiota and health. Compr. Rev. Food Sci. Food Saf. 2021, 20, 710–737. [Google Scholar] [CrossRef] [PubMed]
  45. Bhatta, S.; Janezic, T.S.; Ratti, C. Freeze-Drying of Plant-Based Foods. Foods 2020, 9, 87. [Google Scholar] [CrossRef] [PubMed]
  46. Nguyen, Q.-V.; Doan, M.-D.; Thi, B.-H.B.; Nguyen, M.-T.; Minh, D.T.; Nguyen, A.-D.; Le, T.-M.; Nguyen, T.-H.; Tran, V.-C.; Hoang, V.-C. The effect of drying methods on chlorophyll, polyphenol, flavonoids, phenolic compounds contents, color and sensory properties, and in vitro antioxidant and anti-diabetic activities of dried wild guava leaves. Dry. Technol. 2023, 41, 1291–1302. [Google Scholar] [CrossRef]
  47. Kim, D.-W.; Jung, D.-H.; Sung, J.; Min, I.S.; Lee, S.-J. Tart Cherry Extract Containing Chlorogenic Acid, Quercetin, and Kaempferol Inhibits the Mitochondrial Apoptotic Cell Death Elicited by Airborne PM10 in Human Epidermal Keratinocytes. Antioxidants 2021, 10, 443. [Google Scholar] [CrossRef] [PubMed]
  48. Bondonno, N.P.; Bondonno, C.P.; Hodgson, J.M.; Ward, N.C.; Croft, K.D. The Efficacy of Quercetin in Cardiovascular Health. Curr. Nutr. Rep. 2015, 4, 290–303. [Google Scholar] [CrossRef]
  49. Feliciano, R.P.; Pritzel, S.; Heiss, C.; Rodriguez-Mateos, A. Flavonoid intake and cardiovascular disease risk. Curr. Opin. Food Sci. 2015, 2, 92–99. [Google Scholar] [CrossRef]
  50. Ackland, M.L.; Van De Waarsenburg, S.; Jones, R. Synergistic Antiproliferative Action of the Flavonols Quercetin and Kaempferol in Cultured Human Cancer Cell Lines. In Vivo 2005, 19, 69–76. [Google Scholar]
  51. Pang, J.L.; Ricupero, D.A.; Huang, S.; Fatma, N.; Singh, D.P.; Romero, J.R.; Chattopadhyay, N. Differential activity of kaempferol and quercetin in attenuating tumor necrosis factor receptor family signaling in bone cells. Biochem. Pharmacol. 2006, 71, 818–826. [Google Scholar] [CrossRef]
  52. Liu, H.; Xu, Q.; Wufuer, H.; Li, Z.; Sun, R.; Jiang, Z.; Dou, X.; Fu, Q.; Campisi, J.; Sun, Y. Rutin is a potent senomorphic agent to target senescent cells and can improve chemotherapeutic efficacy. Aging Cell 2024, 23, e13921. [Google Scholar] [CrossRef]
  53. Pravin, B.; Nanaware, V.; Ashwini, B.; Wondmie, G.F.; Bin Jardan, Y.A.; Bourhia, M. Assessing the antioxidant properties of Naringin and Rutin and investigating their oxidative DNA damage effects in breast cancer. Sci. Rep. 2024, 14, 15314. [Google Scholar] [CrossRef] [PubMed]
  54. Khorsheed, S.M.; Abu Raghif, A.R. Anti-proliferative, Anti-oxidant and Anti-inflammatory Effects of Topical Rutin on Imiquimod-Induced Psoriasis in Mice. Pak. J. Life Soc. Sci. PJLSS 2024, 22, 1962–1976. [Google Scholar] [CrossRef]
  55. Wu, Y.; Zhou, S.; Zhao, A.; Mi, Y.; Zhang, C. Protective effect of rutin on ferroptosis-induced oxidative stress in aging laying hens through Nrf2/HO-1 signaling. Cell Biol. Int. 2023, 47, 598–611. [Google Scholar] [CrossRef] [PubMed]
  56. Guan, P.; Yu, H.; Wang, S.; Sun, J.; Chai, X.; Sun, X.; Qi, X.; Zhang, R.; Jiao, Y.; Li, Z.; et al. Dietary rutin alleviated the damage by cold stress on inflammation reaction, tight junction protein and intestinal microbial flora in the mice intestine. J. Nutr. Biochem. 2024, 130, 109658. [Google Scholar] [CrossRef]
  57. Ahmed, O.M.; Elkomy, M.H.; Fahim, H.I.; Ashour, M.B.; Naguib, I.A.; Alghamdi, B.S.; Mahmoud, H.U.R.; Ahmed, N.A. Rutin and Quercetin Counter Doxorubicin-Induced Liver Toxicity in Wistar Rats via Their Modulatory Effects on Inflammation, Oxidative Stress, Apoptosis, and Nrf2. Oxidative Med. Cell. Longev. 2022, 2022, 2710607. [Google Scholar] [CrossRef]
  58. Edwards, R.L.; Lyon, T.; Litwin, S.E.; Rabovsky, A.; Symons, J.D.; Jalili, T. Quercetin Reduces Blood Pressure in Hypertensive Subjects. J. Nutr. 2007, 137, 2405–2411. [Google Scholar] [CrossRef]
  59. Ferenczyova, K.; Kalocayova, B.; Kindernay, L.; Jelemensky, M.; Balis, P.; Berenyiova, A.; Zemancikova, A.; Farkasova, V.; Sykora, M.; Tothova, L.; et al. Quercetin Exerts Age-Dependent Beneficial Effects on Blood Pressure and Vascular Function, But Is Inefficient in Preventing Myocardial Ischemia-Reperfusion Injury in Zucker Diabetic Fatty Rats. Molecules 2020, 25, 187. [Google Scholar] [CrossRef]
  60. Perez-Vizcaino, F.; Duarte, J.; Andriantsitohaina, R. Endothelial function and cardiovascular disease: Effects of quercetin and wine polyphenols. Free Radic. Res. 2006, 40, 1054–1065. [Google Scholar] [CrossRef]
  61. Hubbard, G.P.; Wolffram, S.; de Vos, R.; Bovy, A.; Gibbins, J.M.; Lovegrove, J.A. Ingestion of onion soup high in quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in man: A pilot study. Br. J. Nutr. 2006, 96, 482–488. [Google Scholar] [CrossRef]
  62. Wright, B.; Moraes, L.A.; Kemp, C.F.; Mullen, W.; Crozier, A.; Lovegrove, J.A.; Gibbins, J.M. A structural basis for the inhibition of collagen-stimulated platelet function by quercetin and structurally related flavonoids. Br. J. Pharmacol. 2010, 159, 1312–1325. [Google Scholar] [CrossRef]
  63. Sun, C.; Wang, T.; Wang, C.; Zhu, Z.; Wang, X.; Xu, J.; An, H. The Protective Effect of Kaempferol Against Ischemia/Reperfusion Injury Through Activating SIRT3 to Inhibit Oxidative Stress. Rev. Bras. Cir. Cardiovasc. 2021, 37, 335–342. [Google Scholar] [CrossRef]
  64. Yao, H.; Sun, J.; Wei, J.; Zhang, X.; Chen, B.; Lin, Y. Kaempferol Protects Blood Vessels from Damage Induced by Oxidative Stress and Inflammation in Association with the Nrf2/HO-1 Signaling Pathway. Front. Pharmacol. 2020, 11, 1118. [Google Scholar] [CrossRef]
  65. Bian, Y.; Lei, J.; Zhong, J.; Wang, B.; Wan, Y.; Li, J.; Liao, C.; He, Y.; Liu, Z.; Ito, K.; et al. Kaempferol reduces obesity, prevents intestinal inflammation, and modulates gut microbiota in high-fat diet mice. J. Nutr. Biochem. 2022, 99, 108840. [Google Scholar] [CrossRef]
  66. Patras, A.; Brunton, N.P.; O’Donnell, C.; Tiwari, B. Effect of thermal processing on anthocyanin stability in foods; mechanisms and kinetics of degradation. Trends Food Sci. Technol. 2010, 21, 3–11. [Google Scholar] [CrossRef]
  67. Festa, J.; Da Boit, M.; Hussain, A.; Singh, H. Potential Benefits of Berry Anthocyanins on Vascular Function. Mol. Nutr. Food Res. 2021, 65, 2100170. [Google Scholar] [CrossRef]
  68. Garcia, C.; Blesso, C.N. Antioxidant properties of anthocyanins and their mechanism of action in atherosclerosis. Free Radic. Biol. Med. 2021, 172, 152–166. [Google Scholar] [CrossRef]
  69. Chuntakaruk, H.; Kongtawelert, P.; Pothacharoen, P. Chondroprotective effects of purple corn anthocyanins on advanced glycation end products induction through suppression of NF-κB and MAPK signaling. Sci. Rep. 2021, 11, 1895. [Google Scholar] [CrossRef]
  70. Pomilio, A.B.; Szewczuk, N.A.; Duchowicz, P.R. Dietary anthocyanins balance immune signs in osteoarthritis and obesity—Update of human in vitro studies and clinical trials. Crit. Rev. Food Sci. Nutr. 2024, 64, 2634–2672. [Google Scholar] [CrossRef]
  71. Zeng, Z.; Li, H.; Luo, C.; Hu, W.; Weng, T.-J.; Shuang, F. Pelargonidin ameliorates inflammatory response and cartilage degeneration in osteoarthritis via suppressing the NF-κB pathway. Arch. Biochem. Biophys. 2023, 743, 109668. [Google Scholar] [CrossRef]
  72. Filaferro, M.; Codeluppi, A.; Brighenti, V.; Cimurri, F.; González-Paramás, A.M.; Santos-Buelga, C.; Bertelli, D.; Pellati, F.; Vitale, G. Disclosing the Antioxidant and Neuroprotective Activity of an Anthocyanin-Rich Extract from Sweet Cherry (Prunus avium L.) Using In Vitro and In Vivo Models. Antioxidants 2022, 11, 211. [Google Scholar] [CrossRef]
  73. Seeram, N.P.; Momin, R.A.; Nair, M.G.; Bourquin, L.D. Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries. Phytomedicine 2001, 8, 362–369. [Google Scholar] [CrossRef] [PubMed]
  74. Capanoglu, E.; Boyacioglu, D.; de Vos, R.C.; Hall, R.D.; Beekwilder, J. Procyanidins in fruit from Sour cherry (Prunus cerasus) differ strongly in chainlength from those in Laurel cherry (Prunus lauracerasus) and Cornelian cherry (Cornus mas). J. Berry Res. 2011, 1, 137–146. [Google Scholar] [CrossRef]
  75. Dai, S.; Lian, Z.; Qi, W.; Chen, Y.; Tong, X.; Tian, T.; Lyu, B.; Wang, M.; Wang, H.; Jiang, L. Non-covalent interaction of soy protein isolate and catechin: Mechanism and effects on protein conformation. Food Chem. 2022, 384, 132507. [Google Scholar] [CrossRef]
  76. Le Bourvellec, C.; Renard, C. Interactions between Polyphenols and Macromolecules: Quantification Methods and Mechanisms. Crit. Rev. Food Sci. Nutr. 2012, 52, 213–248. [Google Scholar] [CrossRef]
  77. Prigent, S.V.; Voragen, A.G.; Visser, A.J.; van Koningsveld, G.A.; Gruppen, H. Covalent interactions between proteins and oxidation products of caffeoylquinic acid (chlorogenic acid). J. Sci. Food Agric. 2007, 87, 2502–2510. [Google Scholar] [CrossRef]
  78. Ottaviani, J.I.; Britten, A.; Lucarelli, D.; Luben, R.; Mulligan, A.A.; Lentjes, M.A.; Fong, R.; Gray, N.; Grace, P.B.; Mawson, D.H.; et al. Biomarker-estimated flavan-3-ol intake is associated with lower blood pressure in cross-sectional analysis in EPIC Norfolk. Sci. Rep. 2020, 10, 1796. [Google Scholar] [CrossRef]
  79. Rees, A.; Dodd, G.F.; Spencer, J.P.E. The Effects of Flavonoids on Cardiovascular Health: A Review of Human Intervention Trials and Implications for Cerebrovascular Function. Nutrients 2018, 10, 1852. [Google Scholar] [CrossRef]
  80. Liu, X.; Xing, Y.; Yuen, M.; Yuen, T.; Yuen, H.; Peng, Q. Anti-Aging Effect and Mechanism of Proanthocyanidins Extracted from Sea buckthorn on Hydrogen Peroxide-Induced Aging Human Skin Fibroblasts. Antioxidants 2022, 11, 1900. [Google Scholar] [CrossRef]
  81. Liu, X.; Yuen, M.; Yuen, T.; Yuen, H.; Wang, M.; Peng, Q. Anti-skin aging effect of sea buckthorn proanthocyanidins in D-galactose-induced aging mice. Food Sci. Nutr. 2024, 12, 1082–1094. [Google Scholar] [CrossRef]
  82. Pham-Huy, L.A.; He, H.; Pham-Huy, C. Free Radicals, Antioxidants in Disease and Health. Int. J. Biomed. Sci. IJBS 2008, 4, 89. [Google Scholar]
  83. Zahra, M.; Abrahamse, H.; George, B.P. Flavonoids: Antioxidant Powerhouses and Their Role in Nanomedicine. Antioxidants 2024, 13, 922. [Google Scholar] [CrossRef]
  84. Kometsi, L.; Govender, K.; Mato, E.P.M.; Hurchund, R.; Owira, P.M.O. By reducing oxidative stress, naringenin mitigates hyperglycaemia-induced upregulation of hepatic nuclear factor erythroid 2-related factor 2 protein. J. Pharm. Pharmacol. 2020, 72, 1394–1404. [Google Scholar] [CrossRef] [PubMed]
  85. Yadav, B.; Vishwakarma, V.; Kumar, S.; Aggarwal, N.K.; Gupta, R.; Yadav, A. Ameliorative role of naringenin against lead-induced genetic damage and oxidative stress in cultured human lymphocytes. J. Biochem. Mol. Toxicol. 2022, 36, e23036. [Google Scholar] [CrossRef]
  86. Naeini, F.; Namkhah, Z.; Tutunchi, H.; Rezayat, S.M.; Mansouri, S.; Yaseri, M.; Hosseinzadeh-Attar, M.J. Effects of naringenin supplementation on cardiovascular risk factors in overweight/obese patients with nonalcoholic fatty liver disease: A pilot double-blind, placebo-controlled, randomized clinical trial. Eur. J. Gastroenterol. Hepatol. 2022, 34, 345–353. [Google Scholar] [CrossRef]
  87. Namkhah, Z.; Naeini, F.; Rezayat, S.M.; Yaseri, M.; Mansouri, S.; Hosseinzadeh-Attar, M.J. Does naringenin supplementation improve lipid profile, severity of hepatic steatosis and probability of liver fibrosis in overweight/obese patients with NAFLD? A randomised, double-blind, placebo-controlled, clinical trial. Int. J. Clin. Pract. 2021, 75, e14852. [Google Scholar] [CrossRef] [PubMed]
  88. Ahmed, O.M.; Khalifa, M.M.; Atia, T.; Ahmed, R.R.; Abdel-Hafez, D.A.; Rahman, F.E.-Z.S.A.; Damanhory, A.A.; Metawee, M.E.; Elagali, A.M.; Alqassimi, S.; et al. The Anti-Arthritic Role of Naringenin through Modulating Different T Helper Cells’ Cytokines, Inflammatory Mediators, Oxidative Stress and Anti-Oxidant Defense System. J. Biol. Regul. Homeost. Agents 2024, 38, 5393–5405. [Google Scholar] [CrossRef]
  89. Zhang, W.; Zhang, Y.; Zhang, J.; Deng, C.; Zhang, C. Naringenin ameliorates collagen-induced arthritis through activating AMPK-mediated autophagy in macrophages. Immun. Inflamm. Dis. 2023, 11, e983. [Google Scholar] [CrossRef]
  90. Madureira, M.B.; Concato, V.M.; Cruz, E.M.S.; de Morais, J.M.B.; Inoue, F.S.R.; Santos, N.C.; Gonçalves, M.D.; de Souza, M.C.; Scandolara, T.B.; Mezoni, M.F.; et al. Naringenin and Hesperidin as Promising Alternatives for Prevention and Co-Adjuvant Therapy for Breast Cancer. Antioxidants 2023, 12, 586. [Google Scholar] [CrossRef]
  91. Qi, Z.; Kong, S.; Zhao, S.; Tang, Q. Naringenin inhibits human breast cancer cells (MDA-MB-231) by inducing programmed cell death, caspase stimulation, G2/M phase cell cycle arrest and suppresses cancer metastasis. Cell. Mol. Biol. 2021, 67, 8–13. [Google Scholar] [CrossRef]
  92. Rathi, A.; Chaudhury, A.; Anjum, F.; Ahmad, S.; Haider, S.; Khan, Z.F.; Taiyab, A.; Chakrabarty, A.; Islam, A.; Hassan, I.; et al. Targeting prostate cancer via therapeutic targeting of PIM-1 kinase by Naringenin and Quercetin. Int. J. Biol. Macromol. 2024, 276, 133882. [Google Scholar] [CrossRef]
  93. Wu, Y.; Li, K.; Zeng, M.; Qiao, B.; Zhou, B. Serum Metabolomics Analysis of the Anti-Inflammatory Effects of Gallic Acid on Rats with Acute Inflammation. Front. Pharmacol. 2022, 13, 830439. [Google Scholar] [CrossRef]
  94. Badhani, B.; Sharma, N.; Kakkar, R. Gallic acid: A versatile antioxidant with promising therapeutic and industrial applications. RSC Adv. 2015, 5, 27540–27557. [Google Scholar] [CrossRef]
  95. Thapa, R.; Goyal, A.; Gupta, G.; Bhat, A.A.; Singh, S.K.; Subramaniyan, V.; Sharma, S.; Prasher, P.; Jakhmola, V.; Singh, S.K.; et al. Recent developments in the role of protocatechuic acid in neurodegenerative disorders. EXCLI J. 2023, 22, 595–599. [Google Scholar] [CrossRef] [PubMed]
Table 1. Characterization of polyphenolic compounds in Montmorency tart cherry using triple quadrupole LC–MS-MS, sorted by molecular weight (MW).
Table 1. Characterization of polyphenolic compounds in Montmorency tart cherry using triple quadrupole LC–MS-MS, sorted by molecular weight (MW).
Phenolic CompoundsPhenolic ClassRT (min)MW (m/z)[M-H]− (m/z)MS/MS (m/z)Confirmation
Protocatechuic acidHydroxybenzoic Acid2.24154.12153.0581.05, 91.04, 109.04Identified
p-Coumaric acidHydroxycinnamic Acid3.00, 3.40164.04162.9593.07, 117.00, 119.04Identified
o-Coumaric acid Hydroxycinnamic Acid3.03, 4.40164.16162.9393.04, 117.04, 119.00Identified
Gallic acidHydroxybenzoic Acid6.56170.12168.8379.11, 97.04, 125.22Identified
Caffeic acid Hydroxycinnamic Acid3.61180.16178.9989.07, 107.07, 135.07Identified
Ferulic Acid Hydroxycinnamic Acid4.62194.18192.97134.04, 149.11, 178.04Identified
NaringeninFlavonol4.95, 6.05272.25270.99107.04, 119.07, 151.04Identified
CatechinFlavanol (Flavan-3-ol)3.69290.26289.04203.07, 204.97, 245.04Identified
(-)-EpicatechinFlavanol (Flavan-3-ol)3.69290.26289.39187.54, 203.69, 245.29Identified
PeonidinAnthocyanin5.74301.27299.87259.07, 202.12, 287.12Identified
QuercetinFlavonol5.98302.23301.09151.04, 179.04, 121.04Identified
Taxifolin * (dihydroquercetin)Flavanol (Flavan-3-ol) *4.4304.25303.03124.97, 177.04, 285.04Unconfirmed
Caffeic acid glycosideHydroxycinnamic Acid3.36342.30341.00131.01, 179.04, 220.92Identified
Chlorogenic acidHydroxycinnamic Acid2.52, 3.35354.31353.31191.05, 351.07, 354.09Identified
Feruloquinic acidHydroxycinnamic Acid3.27368.34367.00134.04, 190.95, 193.04Unconfirmed
Quercetin-3-glucoside Flavonol4.96463.40462.86255.13, 271.08, 299.77Identified
Cyanidin-3-glucosideAnthocyanin4.65, 5.30484.83447.18255.08, 284.13, 285.13Identified
Procyanidin B2Flavanol (Flavan-3-ol)3.00, 3.34578.52577.53289.07, 425.08, 455.07Identified
Kaempferol-3-rutinosideFlavonol5.31594.52593.00285.00, 447.00, 535.00Identified
Cyanidin-3-rutinosideAnthocyanin3.77, 5.30595.52594.20163.06, 307.10, 325.11Identified
Peonidin-3-rutinosideAnthocyanin3.98609.60608.00145.05, 163.06, 307.10Identified
Rutin (quercetin-3-O-rutinoside)Flavonol4.91610.51609.00254.97, 271.04, 300.04Identified
Cyanidin-3-sophorosideAnthocyanin0.16611.50610.50535.21, 488.21, 575.20Identified
Protocatechuic acidHydroxybenzoic Acid2.24154.12153.0581.05, 91.04, 109.04Identified
* Taxifolin also can be classified as a flavanonol, sometimes considered a flavonoid subclass distinct from flavan-3-ols.
Table 2. Total polyphenolic content of Montmorency tart cherry polyphenol classes in five tart cherry products reported as ppm (dry weight basis) ± standard deviation (n = 3) and percentage of each class in each product.
Table 2. Total polyphenolic content of Montmorency tart cherry polyphenol classes in five tart cherry products reported as ppm (dry weight basis) ± standard deviation (n = 3) and percentage of each class in each product.
Polyphenol ClassFrozen Raw CherriesCherry Juice ConcentrateUnsweetened Dried CherriesFreeze Dried Cherry PowderSweet Dried Cherries
Hydroxycinnamic Acids44,827 ± 197
(54%)		40,476 ± 16
(66%)		36,296 ± 15
(74%)		9585 ± 17
(29%)		15,519 ± 60
(83%)
Flavonols16,390 ± 15
(20%)		10,504 ± 2
(17%)		9825 ± 4
(20%)		16,912 ± 11
(52%)		2340 ± 1
(13%)
Anthocyanins15,204 ± 36
(18%)		2852 ± 3
(5%)		2171 ± 8
(4%)		2060 ± 2
(6%)		691 ± 4
(4%)
Flavanols (Flavan-3-ols)6107 ± 7
(7%)		6863 ± 9
(11%)		57 ± 1
(<1%)		911 ± 4
(2%)		16 ± 1
(<1%)
Flavanones254 ± 3
(<1%)		262 ± 1
(<1%)		356 ± 1
(<1%)		928 ± 1
(3%)		79 ± 1
(<1%)
Hydroxybenzoic Acids101 ± 1
(<1%)		480 ± 2
(<1%)		572 ± 1
(1%)		2531 ± 24
(8%)		161 ± 1
(<1%)
Table 3. Individual polyphenolic compounds (ppm dry weight ± standard deviation, n = 3) of Montmorency tart cherry in five tart cherry products.
Table 3. Individual polyphenolic compounds (ppm dry weight ± standard deviation, n = 3) of Montmorency tart cherry in five tart cherry products.
Polyphenol CompoundsFrozen Raw CherriesCherry Juice ConcentrateUnsweetened Dried CherriesFreeze Dried Cherry PowderSweet Dried Cherries
Hydroxycinnamic Acids
Chlorogenic Acid29,392 ± 2822,729 ± 721,362 ± 72776 ± 79544 ± 9
Feruloquinic Acid8087 ± 547226 ± 285421 ± 252906 ± 122383 ± 13
Ferulic Acid 3067 ± 152582 ± 332456 ± 142588 ± 291445 ± 26
p-Coumaric acid1750 ± 83002 ±13018 ± 2431 ± 0850 ± 1
o-Coumaric acid 1759 ± 13237 ± 33256 ± 6715 ± 31031 ± 12
Caffeic acid glycoside453 ± 070 ± 042 ± 048 ± 099 ± 0
Caffeic acid 169 ± 11631 ± 0745 ± 0133 ± 0168 ± 0
Flavonols
Rutin (quercetin-3-O-rutinoside)15,940 ± 1110,097 ± 19522 ± 316,080 ± 92292 ± 0
Quercetin-3-glucoside 299 ± 2203 ± 0166 ± 0436 ± 031 ± 0
Kaempferol-3-rutinoside149 ± 087 ± 075 ± 0174 ± 017 ± 0
Quercetinnd117 ± 063 ± 0223 ± 0nd
Anthocyanins
Cyanidin-3-Sophoroside9930 ± 18207 ± 2154 ± 5279 ± 4302 ± 2
Peonidin-3-rutinoside2630 ± 16273 ± 0nd313 ± 0nd
Cyanidin-3-Rutinoside1667 ± 51494 ± 11273 ± 3872 ± 1245 ± 0
Cyanidin-3-Glucoside981 ± 1879 ± 0745 ± 0514 ± 4144 ± 0
Peonidinndndnd84 ± 2nd
Flavanols (Flavan-3-ols)
(-)-Epicatechin2614 ± 152665 ± 1nd361 ± 2nd
Catechin2157 ± 132740 ± 6nd272 ± 1nd
Procyanidin B21291 ± 151323 ± 122 ± 089 ± 0nd
Taxifolin (dihydroquercetin)43 ± 0136 ± 036 ± 0188 ± 016 ± 0
Flavanones
Naringenin255 ± 2262 ± 1356 ± 1929 ± 079 ± 0
Hydroxybenzoic Acids
Protocatechuic acid102 ± 1480 ± 2573 ± 1219 ± 0161 ± 0
Gallic acidndndnd2311 ± 24nd
nd = not detected.
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content.

Share and Cite

MDPI and ACS Style

Jawad, M.; Talcott, S.T.; Hillman, A.R.; Brannan, R.G. A Comprehensive Polyphenolic Characterization of Five Montmorency Tart Cherry (Prunus cerasus L.) Product Formulations. Foods 2025, 14, 1154. https://doi.org/10.3390/foods14071154

AMA Style

Jawad M, Talcott ST, Hillman AR, Brannan RG. A Comprehensive Polyphenolic Characterization of Five Montmorency Tart Cherry (Prunus cerasus L.) Product Formulations. Foods. 2025; 14(7):1154. https://doi.org/10.3390/foods14071154

Chicago/Turabian Style

Jawad, Muhammad, Stephen T. Talcott, Angela R. Hillman, and Robert G. Brannan. 2025. "A Comprehensive Polyphenolic Characterization of Five Montmorency Tart Cherry (Prunus cerasus L.) Product Formulations" Foods 14, no. 7: 1154. https://doi.org/10.3390/foods14071154

APA Style

Jawad, M., Talcott, S. T., Hillman, A. R., & Brannan, R. G. (2025). A Comprehensive Polyphenolic Characterization of Five Montmorency Tart Cherry (Prunus cerasus L.) Product Formulations. Foods, 14(7), 1154. https://doi.org/10.3390/foods14071154

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop