Skip to main content
Top
Published in: BMC Complementary Medicine and Therapies 1/2024

Open Access 01-12-2024 | Research

Crataegus pentagyna willd. Fruits, leaves and roots: phytochemicals, antioxidant and antimicrobial potentials

Authors: Akram Taleghani, Samira Eghbali, Roya Moghimi, Majid Mokaber-Esfahani

Published in: BMC Complementary Medicine and Therapies | Issue 1/2024

Login to get access

Abstract

Background

The hawthorn has recently been used as a popular herbal medicine in food applications and phytotherapy, especially for the cardiovascular system.

Methods

In this study, phytochemicals were evaluated by LC-ESI-MS, GC-MS, and biological activity, including antioxidant (DPPH test) and antibacterial (broth dilution assay), in different extracts of Crataegus pentagyna fruit, leaf, and root.

Results

Globally, 49 phenolics were tentatively identified using HPLC-ESI-MS/MS in the hydro-methanolic extract of the fruit (major apigenin, caffeoylquinic acid derivative, and 4-O-(3′-O-glucopyranosyl)-caffeoyl quinic acid), 42 in the leaf (major salicylic acid, naringenin-6-C-glucoside, and naringin), and 33 in the root (major naringenin-7-O-neohesperidoside, isovitexin-2″-O-rhamnoside, and 4-O-(3′-O-glucopyranosyl)-caffeoyl quinic acid). The major group compounds analyzed by GC-MS in petroleum ether extracts were hydrocarbons (63.80%) and fatty acids and their derivatives (11.77%) in fruit, hydrocarbons (49.20%) and fatty acids and their derivatives (13.85%) in leaf, and hydrocarbons (53.96%) and terpenes (13.06%) in root. All samples exhibited promising phytochemical profile (total phenol, flavonoid, phenolic acid, and anthocyanin), antioxidant and antibacterial capacities, especially in hydro-methanolic extract of fruit (210.22 ± 0.44 mg GAE/g DE; 79.93 ± 0.54 mg QE/g DE; 194.64 ± 0.32 mg CAE/g DE; 85.37 ± 0.13 mg cyanidin 3-glucoside/100 g FW; DPPH: 15.43 ± 0.65 µg/mL; MIC: 0.15–0.62 µg/mL; and MBC: 0.62–1.25 mg/mL), followed by the leaf and root extracts, respectively. The PCA and heatmap analysis results distinguished metabolite profile differences for samples.

Conclusion

The results of the present work provide scientific support for C. pentagyna as antimicrobial agents and natural antioxidants in human health and food preservation.
Appendix
Available only for authorised users
Literature
1.
go back to reference Bahorun T, Aumjaud E, Ramphul H, Rycha M, Luximon-Ramma A, Trotin F, et al. Phenolic constituents and antioxidant capacities of Crataegus monogyna (Hawthorn) callus extracts. Mol Nutr Food Res. 2003;47(3):191–8. Bahorun T, Aumjaud E, Ramphul H, Rycha M, Luximon-Ramma A, Trotin F, et al. Phenolic constituents and antioxidant capacities of Crataegus monogyna (Hawthorn) callus extracts. Mol Nutr Food Res. 2003;47(3):191–8.
2.
go back to reference Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem. 2007;39(1):44–84.CrossRef Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem. 2007;39(1):44–84.CrossRef
3.
go back to reference Shivaprasad HN, Mulukuri NS, Chandrasekar SB, Baheti AM, Pawar AT. Role of natural products in infectious diseases. Viral, parasitic, bacterial, and fungal in fections. Academic; 2023. pp. 757–70. Shivaprasad HN, Mulukuri NS, Chandrasekar SB, Baheti AM, Pawar AT. Role of natural products in infectious diseases. Viral, parasitic, bacterial, and fungal in fections. Academic; 2023. pp. 757–70.
4.
go back to reference Salam MA, Al-Amin MY, Salam MT, Pawar JS, Akhter N, Rabaan AA, et al. Antimicrobial resistance: a growing serious threat for global public health. J Healthc. 2023;11(13):1946.CrossRef Salam MA, Al-Amin MY, Salam MT, Pawar JS, Akhter N, Rabaan AA, et al. Antimicrobial resistance: a growing serious threat for global public health. J Healthc. 2023;11(13):1946.CrossRef
5.
go back to reference Lin JY, Tang CY. Determination of total phenolic and flavonoid contents in selected fruits and vegetables, as well as their stimulatory effects on mouse splenocyte proliferation. Food Chem. 2007;101(1):140–7.CrossRef Lin JY, Tang CY. Determination of total phenolic and flavonoid contents in selected fruits and vegetables, as well as their stimulatory effects on mouse splenocyte proliferation. Food Chem. 2007;101(1):140–7.CrossRef
7.
go back to reference Hernández-Rodríguez P, Baquero LP, Larrota HR. Flavonoids: potential therapeutic agents by their antioxidant capacity. Bioact Compd. Woodhead Publishing; 2019. pp. 265–88. Hernández-Rodríguez P, Baquero LP, Larrota HR. Flavonoids: potential therapeutic agents by their antioxidant capacity. Bioact Compd. Woodhead Publishing; 2019. pp. 265–88.
8.
go back to reference Venskutonis PR. Phytochemical composition and bioactivities of hawthorn (Crataegus spp.): review of recent research advances. J food Bioact. 2018;4:69–87.CrossRef Venskutonis PR. Phytochemical composition and bioactivities of hawthorn (Crataegus spp.): review of recent research advances. J food Bioact. 2018;4:69–87.CrossRef
9.
go back to reference Nazhand A, Lucarini M, Durazzo A, Zaccardelli M, Cristarella S, Souto SB et al. Hawthorn (Crataegus spp.): An Updated Overview on Its Beneficial Properties. Forests; 2020, 11(5): 564. Nazhand A, Lucarini M, Durazzo A, Zaccardelli M, Cristarella S, Souto SB et al. Hawthorn (Crataegus spp.): An Updated Overview on Its Beneficial Properties. Forests; 2020, 11(5): 564.
10.
go back to reference Tassell MC, Kingston R, Gilroy D, Lehane M, Furey A. Hawthorn (Crataegus spp.) in the treatment of cardiovascular disease. Pharmacogn Rev. 2010;4(7):32–41.PubMedPubMedCentralCrossRef Tassell MC, Kingston R, Gilroy D, Lehane M, Furey A. Hawthorn (Crataegus spp.) in the treatment of cardiovascular disease. Pharmacogn Rev. 2010;4(7):32–41.PubMedPubMedCentralCrossRef
11.
go back to reference Holubarsch CJ, Colucci WS, Eha J. Benefit-risk assessment of Crataegus extract WS 1442: an evidence-based review. Am J Cardiovasc Drugs. 2018;18:25–36.PubMedCrossRef Holubarsch CJ, Colucci WS, Eha J. Benefit-risk assessment of Crataegus extract WS 1442: an evidence-based review. Am J Cardiovasc Drugs. 2018;18:25–36.PubMedCrossRef
12.
go back to reference Yang B, Liu P. Composition and health effects of phenolic compounds in hawthorn (Crataegus spp.) of different origins. J Sci Food Agric. 2012;92(8):1578–90.PubMedCrossRef Yang B, Liu P. Composition and health effects of phenolic compounds in hawthorn (Crataegus spp.) of different origins. J Sci Food Agric. 2012;92(8):1578–90.PubMedCrossRef
13.
go back to reference Cloud A, Vilcins D, McEwen B. The effect of hawthorn (Crataegus spp.) on blood pressure: a systematic review. Adv Integr Med. 2019;7(3):167–75.CrossRef Cloud A, Vilcins D, McEwen B. The effect of hawthorn (Crataegus spp.) on blood pressure: a systematic review. Adv Integr Med. 2019;7(3):167–75.CrossRef
14.
go back to reference Kumar D, Arya V, Bhat ZA, Khan NA, Prasad DN. The genus Crataegus: Chemical and pharmacological perspectives. Rev Bras Farmacogn. 2012;22(5):1187–200.CrossRef Kumar D, Arya V, Bhat ZA, Khan NA, Prasad DN. The genus Crataegus: Chemical and pharmacological perspectives. Rev Bras Farmacogn. 2012;22(5):1187–200.CrossRef
15.
go back to reference Alirezalu A, Ahmadi N, Salehi P, Sonboli A, Alirezalu K, Khaneghah AM, et al. Physicochemical characterization, antioxidant activity, and phenolic compounds of Hawthorn (Crataegus spp.) fruits species for potential use in food applications. Foods. 2020;9(4):436.PubMedPubMedCentralCrossRef Alirezalu A, Ahmadi N, Salehi P, Sonboli A, Alirezalu K, Khaneghah AM, et al. Physicochemical characterization, antioxidant activity, and phenolic compounds of Hawthorn (Crataegus spp.) fruits species for potential use in food applications. Foods. 2020;9(4):436.PubMedPubMedCentralCrossRef
16.
go back to reference Salmanian S, Sadeghi Mahoonak A, Alami M, Ghorbani M. Phenolic content, antiradical, antioxidant, and antibacterial properties of hawthorn (Crataegus elbursensis) seed and pulp extract. J Agric Sci Technol. 2014;16(2):343–54. Salmanian S, Sadeghi Mahoonak A, Alami M, Ghorbani M. Phenolic content, antiradical, antioxidant, and antibacterial properties of hawthorn (Crataegus elbursensis) seed and pulp extract. J Agric Sci Technol. 2014;16(2):343–54.
17.
go back to reference Prinz S, Ringl A, Huefner A, Pemp E, Kopp B. 4′′′-Acetylvitexin-2 ″-O-rhamnoside, isoorientin, orientin, and 8-methoxykaempferol-3-O-glucoside as markers for the differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae). Chem Biodivers. 2007;4(12):2920–31.PubMedCrossRef Prinz S, Ringl A, Huefner A, Pemp E, Kopp B. 4′′′-Acetylvitexin-2 ″-O-rhamnoside, isoorientin, orientin, and 8-methoxykaempferol-3-O-glucoside as markers for the differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae). Chem Biodivers. 2007;4(12):2920–31.PubMedCrossRef
18.
go back to reference Pavlovic J, Mitic S, Mitic M, Kocic G, Pavlovic A, Tosic S. Variation in the phenolic compounds profile and antioxidant activity in different parts of hawthorn (Crataegus pentagyna Willd.) During harvest periods. Pol J Food Nutr Sci. 2019;69(4):367–78.CrossRef Pavlovic J, Mitic S, Mitic M, Kocic G, Pavlovic A, Tosic S. Variation in the phenolic compounds profile and antioxidant activity in different parts of hawthorn (Crataegus pentagyna Willd.) During harvest periods. Pol J Food Nutr Sci. 2019;69(4):367–78.CrossRef
19.
go back to reference Bujor A, Miron A, Luca SV, Skalicka-Wozniak K, Silion M, Trifan A, et al. Vasorelaxant effects of Crataegus pentagyna: links with arginase inhibition and phenolic profile. J Ethnopharmacol. 2020;252:112559.PubMedCrossRef Bujor A, Miron A, Luca SV, Skalicka-Wozniak K, Silion M, Trifan A, et al. Vasorelaxant effects of Crataegus pentagyna: links with arginase inhibition and phenolic profile. J Ethnopharmacol. 2020;252:112559.PubMedCrossRef
20.
go back to reference Cui M, Cheng L, Zhou Z, Zhu Z, Liu Y, Li C, et al. Traditional uses, phytochemistry, pharmacology, and safety concerns of hawthorn (Crataegus Genus): a comprehensive review. J Ethnopharmacol. 2023;319:117229.PubMedCrossRef Cui M, Cheng L, Zhou Z, Zhu Z, Liu Y, Li C, et al. Traditional uses, phytochemistry, pharmacology, and safety concerns of hawthorn (Crataegus Genus): a comprehensive review. J Ethnopharmacol. 2023;319:117229.PubMedCrossRef
21.
go back to reference Singleton VL, Rossi JA. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am J Enol Vitic. 1965;16(3):144–58.CrossRef Singleton VL, Rossi JA. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am J Enol Vitic. 1965;16(3):144–58.CrossRef
22.
go back to reference Celep E, Aydın A, Yesilada E. A comparative study on the in vitro antioxidant potentials of three edible fruits: Cornelian cherry, Japanese persimmon and cherry laurel. Food Chem Toxicol. 2012;50(9):3329–35.PubMedCrossRef Celep E, Aydın A, Yesilada E. A comparative study on the in vitro antioxidant potentials of three edible fruits: Cornelian cherry, Japanese persimmon and cherry laurel. Food Chem Toxicol. 2012;50(9):3329–35.PubMedCrossRef
23.
go back to reference Mihailovic V, Kreft S, Benkovic ET, Ivanovic N, Stankovic MS. Chemical profile, antioxidant activity and stability in stimulated gastrointestinal tract model system of three Verbascum species. Ind Crops Prod. 2016;89:141–51.CrossRef Mihailovic V, Kreft S, Benkovic ET, Ivanovic N, Stankovic MS. Chemical profile, antioxidant activity and stability in stimulated gastrointestinal tract model system of three Verbascum species. Ind Crops Prod. 2016;89:141–51.CrossRef
24.
go back to reference Connor AM, Luby JJ, Tong CB. Variability in antioxidant activity in blueberry and correlations among different antioxidant activity assays. J Am Soc Hortic Sci. 2002;127(2):238–44.CrossRef Connor AM, Luby JJ, Tong CB. Variability in antioxidant activity in blueberry and correlations among different antioxidant activity assays. J Am Soc Hortic Sci. 2002;127(2):238–44.CrossRef
25.
go back to reference Mahmoodi S, Taleghani A, Akbari R, Mokaber-Esfahani M. Rhamnus pallasii subsp. sintenisii fruit, leaf, bark and root: phytochemical profiles and biological activities. Arab J Chem. 2022;15(7):103924.CrossRef Mahmoodi S, Taleghani A, Akbari R, Mokaber-Esfahani M. Rhamnus pallasii subsp. sintenisii fruit, leaf, bark and root: phytochemical profiles and biological activities. Arab J Chem. 2022;15(7):103924.CrossRef
26.
go back to reference Shour S, Iranshahy M, Pham N, Quinn RJ, Iranshahi M. Dereplication of cytotoxic compounds from different parts of Sophora pachycarpa using an integrated method of HPLC, LC-MS and 1H-NMR techniques. Nat Prod Res. 2017;31(11):1270–6.PubMedCrossRef Shour S, Iranshahy M, Pham N, Quinn RJ, Iranshahi M. Dereplication of cytotoxic compounds from different parts of Sophora pachycarpa using an integrated method of HPLC, LC-MS and 1H-NMR techniques. Nat Prod Res. 2017;31(11):1270–6.PubMedCrossRef
27.
go back to reference Pluskal T, Castillo S, Villar-Briones A, Oresic M. MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinform. 2010;11(1):395.CrossRef Pluskal T, Castillo S, Villar-Briones A, Oresic M. MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinform. 2010;11(1):395.CrossRef
28.
go back to reference Abdel-Hameed ESS, Bazaid SA, Al Zahrani O, El-Halmouch Y, El-Sayed MM, El-Wakil E. Chemical composition of volatile components, antimicrobial and anticancer activity of n-hexane extract and essential oil from Trachyspermum ammi L. seeds. Orient J Chem. 2014;30(4):1653–62.CrossRef Abdel-Hameed ESS, Bazaid SA, Al Zahrani O, El-Halmouch Y, El-Sayed MM, El-Wakil E. Chemical composition of volatile components, antimicrobial and anticancer activity of n-hexane extract and essential oil from Trachyspermum ammi L. seeds. Orient J Chem. 2014;30(4):1653–62.CrossRef
29.
go back to reference Gholamalipour Alamdari E, Taleghani A. New bioactive compounds characterized by liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry in hydro-methanol and petroleum ether extracts of Prosopis farcta (Banks & Sol.) JF Macbr weed. J Mass Spectrom. 2022;57(9):e4884.PubMedCrossRef Gholamalipour Alamdari E, Taleghani A. New bioactive compounds characterized by liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry in hydro-methanol and petroleum ether extracts of Prosopis farcta (Banks & Sol.) JF Macbr weed. J Mass Spectrom. 2022;57(9):e4884.PubMedCrossRef
30.
go back to reference Celep E, Aydın A, Kırmızıbekmez H, Yesilada E. Appraisal of in vitro and in vivo antioxidant activity potential of cornelian cherry leaves. Food Chem Toxicol. 2013;62:448–55.PubMedCrossRef Celep E, Aydın A, Kırmızıbekmez H, Yesilada E. Appraisal of in vitro and in vivo antioxidant activity potential of cornelian cherry leaves. Food Chem Toxicol. 2013;62:448–55.PubMedCrossRef
31.
go back to reference European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution. Clin Microbiol Infect. 2003;9:1–7. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution. Clin Microbiol Infect. 2003;9:1–7.
32.
go back to reference Ebrahimzadeh MA, Enayatifard R, Khalili M, Ghaffarloo M, Saeedi M, Charati JY. Correlation between sun protection factor and antioxidant activity, phenol and flavonoid contents of some medicinal plants. Iran J Pharm Sci. 2014;13(3):1041–7. Ebrahimzadeh MA, Enayatifard R, Khalili M, Ghaffarloo M, Saeedi M, Charati JY. Correlation between sun protection factor and antioxidant activity, phenol and flavonoid contents of some medicinal plants. Iran J Pharm Sci. 2014;13(3):1041–7.
33.
go back to reference Jurikova T, Sochor J, Rop O, Mlcek J, Balla S, Szekeres L, Adam V, Kizek R. Polyphenolic profile and biological activity of Chinese hawthorn (Crataegus pinnatifida bunge) fruits. Molecules. 2012;17(12):14490–509.PubMedPubMedCentralCrossRef Jurikova T, Sochor J, Rop O, Mlcek J, Balla S, Szekeres L, Adam V, Kizek R. Polyphenolic profile and biological activity of Chinese hawthorn (Crataegus pinnatifida bunge) fruits. Molecules. 2012;17(12):14490–509.PubMedPubMedCentralCrossRef
34.
go back to reference Ebrahimzadeh M, Bahramian F. Antioxidant activity of Crataegus Pentaegyna Subsp. elburensis fruits extracts used in Traditional Medicine in Iran. Pak J Biol Sci. 2009;12(5):413–9.PubMedCrossRef Ebrahimzadeh M, Bahramian F. Antioxidant activity of Crataegus Pentaegyna Subsp. elburensis fruits extracts used in Traditional Medicine in Iran. Pak J Biol Sci. 2009;12(5):413–9.PubMedCrossRef
35.
go back to reference Ebrahimzadeh MA, Pourmorad F, Bekhradnia AR. Iron chelating activity, phenol and flavonoid content of some medicinal plants from Iran. Afr J Biotechnol. 2008;7(18):3188–92. Ebrahimzadeh MA, Pourmorad F, Bekhradnia AR. Iron chelating activity, phenol and flavonoid content of some medicinal plants from Iran. Afr J Biotechnol. 2008;7(18):3188–92.
36.
go back to reference Rabiei K, Bekhradnia S, Nabavi S, Nabavi S, Ebrahimzadeh M. Antioxidant activity of polyphenol and ultrasonic extracts from fruits of Crataegus pentagyna subsp. elburensis. Nat Prod Res. 2012;26(24):2353–7.PubMedCrossRef Rabiei K, Bekhradnia S, Nabavi S, Nabavi S, Ebrahimzadeh M. Antioxidant activity of polyphenol and ultrasonic extracts from fruits of Crataegus pentagyna subsp. elburensis. Nat Prod Res. 2012;26(24):2353–7.PubMedCrossRef
37.
go back to reference Bujor A, Ochiuz L, Sha’at M, Stoleriu I, Iliuţa SM, Luca SV, Miron A. Chemical, antioxidant and in vitro permeation and penetration studies of extracts obtained from Viburnum opulus and Crataegus pentagyna. Farmacia. 2020;68(4):672–8.CrossRef Bujor A, Ochiuz L, Sha’at M, Stoleriu I, Iliuţa SM, Luca SV, Miron A. Chemical, antioxidant and in vitro permeation and penetration studies of extracts obtained from Viburnum opulus and Crataegus pentagyna. Farmacia. 2020;68(4):672–8.CrossRef
38.
go back to reference Bedreag CFG, Trifan A, Bucur LA, Arcus M, Tebrencu C, Miron A, Costache II. Chemical and antioxidant studies on Crataegus pentagyna leaves and flowers. Rom Biotechnol Lett. 2014;19(6):9859. Bedreag CFG, Trifan A, Bucur LA, Arcus M, Tebrencu C, Miron A, Costache II. Chemical and antioxidant studies on Crataegus pentagyna leaves and flowers. Rom Biotechnol Lett. 2014;19(6):9859.
39.
go back to reference Diao WR, Hu QP, Zhang H, Xu JG. Chemical composition, antibacterial activity and mechanism of action of essential oil from seeds of fennel (Foeniculum vulgare Mill). Food Control. 2014;35(1):109–16.CrossRef Diao WR, Hu QP, Zhang H, Xu JG. Chemical composition, antibacterial activity and mechanism of action of essential oil from seeds of fennel (Foeniculum vulgare Mill). Food Control. 2014;35(1):109–16.CrossRef
40.
go back to reference Bujor O, Stefanache C, Volf I, Danila D. Antioxidant capacity of Crataegus monogyna and Crataegus pentagyna leaves and fruits harvested from the Danube Delta. Planta Med. 2016;82(S 01):S1–381. Bujor O, Stefanache C, Volf I, Danila D. Antioxidant capacity of Crataegus monogyna and Crataegus pentagyna leaves and fruits harvested from the Danube Delta. Planta Med. 2016;82(S 01):S1–381.
41.
go back to reference Cuyckens F, Claeys M. Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom. 2004;39(1):1–15.PubMedCrossRef Cuyckens F, Claeys M. Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom. 2004;39(1):1–15.PubMedCrossRef
42.
go back to reference Melikoglu G, Bitis L, MeriCli AH. Flavonoids of Crataegus microphylla. Nat Prod Res. 2004;18(3):211–3.PubMedCrossRef Melikoglu G, Bitis L, MeriCli AH. Flavonoids of Crataegus microphylla. Nat Prod Res. 2004;18(3):211–3.PubMedCrossRef
43.
go back to reference Ringl A, Prinz S, Huefner A, Kurzmann M, Kopp B. Chemosystematic Value of flavonoids from Crataegus x macrocarpa (Rosaceae) with special emphasis on (R)-and (S)-Eriodictyol-7-O-glucuronide and Luteolin-7-O-glucuronide. Chem Biodivers. 2007;4(2):154–62.PubMedCrossRef Ringl A, Prinz S, Huefner A, Kurzmann M, Kopp B. Chemosystematic Value of flavonoids from Crataegus x macrocarpa (Rosaceae) with special emphasis on (R)-and (S)-Eriodictyol-7-O-glucuronide and Luteolin-7-O-glucuronide. Chem Biodivers. 2007;4(2):154–62.PubMedCrossRef
44.
go back to reference Sadeghi-Kiakhani M, Tehrani-Bagha AR, Safapour S, Eshaghloo-Galugahi S, Etezad SM. Ultrasound-assisted extraction of natural dyes from Hawthorn fruits for dyeing polyamide fabric and study its fastness, antimicrobial, and antioxidant properties. Environ Dev Sustain. 2020;23:9163–80.CrossRef Sadeghi-Kiakhani M, Tehrani-Bagha AR, Safapour S, Eshaghloo-Galugahi S, Etezad SM. Ultrasound-assisted extraction of natural dyes from Hawthorn fruits for dyeing polyamide fabric and study its fastness, antimicrobial, and antioxidant properties. Environ Dev Sustain. 2020;23:9163–80.CrossRef
45.
go back to reference Gruz J, Ayaz FA, Torun H, Strnad M. Phenolic acid content and radical scavenging activity of extracts from medlar (Mespilus germanica L.) fruit at different stages of ripening. Food Chem. 2011;124(1):271–7.CrossRef Gruz J, Ayaz FA, Torun H, Strnad M. Phenolic acid content and radical scavenging activity of extracts from medlar (Mespilus germanica L.) fruit at different stages of ripening. Food Chem. 2011;124(1):271–7.CrossRef
46.
go back to reference Cui T, Li JZ, Kayahara H, Ma L, Wu LX, Nakamura K. Quantification of the polyphenols and triterpene acids in Chinese hawthorn fruit by high-performance liquid chromatography. J Agric Food Chem. 2006;54(13):4574–81.PubMedCrossRef Cui T, Li JZ, Kayahara H, Ma L, Wu LX, Nakamura K. Quantification of the polyphenols and triterpene acids in Chinese hawthorn fruit by high-performance liquid chromatography. J Agric Food Chem. 2006;54(13):4574–81.PubMedCrossRef
47.
go back to reference Bahri-Sahloul R, Ammar S, Fredj R, Saguem S, Grec S, Trotin F, Skhiri FH. Polyphenol contents and antioxidant activities of extracts from flowers of two Crataegus azarolus L. varieties. Pak J Biol Sci. 2009;12(9):660–8.PubMedCrossRef Bahri-Sahloul R, Ammar S, Fredj R, Saguem S, Grec S, Trotin F, Skhiri FH. Polyphenol contents and antioxidant activities of extracts from flowers of two Crataegus azarolus L. varieties. Pak J Biol Sci. 2009;12(9):660–8.PubMedCrossRef
48.
go back to reference Alirezalu A, Salehi P, Ahmadi N, Sonboli A, Aceto S, Hatami Maleki H, Ayyari M. Flavonoids profile and antioxidant activity in flowers and leaves of hawthorn species (Crataegus spp.) from different regions of Iran. Int J Food Prop. 2018;21(1):452–70.CrossRef Alirezalu A, Salehi P, Ahmadi N, Sonboli A, Aceto S, Hatami Maleki H, Ayyari M. Flavonoids profile and antioxidant activity in flowers and leaves of hawthorn species (Crataegus spp.) from different regions of Iran. Int J Food Prop. 2018;21(1):452–70.CrossRef
49.
go back to reference Liu P. Composition of hawthorn (Crataegus spp.) fruits and leaves and emblic leafflower (Phyllanthus emblica) fruits. Ph.D. Thesis, Department of Biochemistry and Food Chemistry and Functional Foods Forum, University of Turku, Turku, Finland, 2012. Liu P. Composition of hawthorn (Crataegus spp.) fruits and leaves and emblic leafflower (Phyllanthus emblica) fruits. Ph.D. Thesis, Department of Biochemistry and Food Chemistry and Functional Foods Forum, University of Turku, Turku, Finland, 2012.
50.
go back to reference Verma S, Jain V, Verma D, Khamesra R. Crataegus oxyacantha-A cardioprotective herb. J Herb Med Toxicol. 2007;1(1):65–71. Verma S, Jain V, Verma D, Khamesra R. Crataegus oxyacantha-A cardioprotective herb. J Herb Med Toxicol. 2007;1(1):65–71.
51.
go back to reference Lu M, Hu JY, Song ZY, Jiao J, Mu FS, Ruan X, Gai QY, Qiao Q, Zu YG, Fu YJ. Optimization of ultrasound-assisted extraction (UAE) of phenolic compounds from Crataegus pinnatifida leaves and evaluation of antioxidant activities of extracts. RSC Adv. 2015;5(83):67532–40.CrossRef Lu M, Hu JY, Song ZY, Jiao J, Mu FS, Ruan X, Gai QY, Qiao Q, Zu YG, Fu YJ. Optimization of ultrasound-assisted extraction (UAE) of phenolic compounds from Crataegus pinnatifida leaves and evaluation of antioxidant activities of extracts. RSC Adv. 2015;5(83):67532–40.CrossRef
52.
go back to reference Mraihi F, Fadhil H, Trabelsi-Ayadi M, Cherif JK. Chemical characterization by HPLC-DAD-ESI/MS of flavonoids from hawthorn fruits and their inhibition of human tumor growth. J New Sci. 2015;3:840–6. Mraihi F, Fadhil H, Trabelsi-Ayadi M, Cherif JK. Chemical characterization by HPLC-DAD-ESI/MS of flavonoids from hawthorn fruits and their inhibition of human tumor growth. J New Sci. 2015;3:840–6.
53.
go back to reference Orhan I, Ozçelik B, Kartal M, Ozdeveci B, Duman H. HPLC quantification of vitexine-2″-O-rhamnoside and hyperoside in three Crataegus species and their antimicrobial and antiviral activities. Chromatographia. 2007;66(Suppl 1):153–7.CrossRef Orhan I, Ozçelik B, Kartal M, Ozdeveci B, Duman H. HPLC quantification of vitexine-2″-O-rhamnoside and hyperoside in three Crataegus species and their antimicrobial and antiviral activities. Chromatographia. 2007;66(Suppl 1):153–7.CrossRef
54.
go back to reference Bykov VI, Glyzin VI. Flavonoids of the genus Crataegus. Chem Nat Compd. 1972;8:672–3.CrossRef Bykov VI, Glyzin VI. Flavonoids of the genus Crataegus. Chem Nat Compd. 1972;8:672–3.CrossRef
55.
go back to reference Si J, Gao G, Chen D. Chemical constituents of the leaves of Crataegus Scabrifolia. (Franch) Rehd China J Chin Mater Med. 1998;23(7):422–48. Si J, Gao G, Chen D. Chemical constituents of the leaves of Crataegus Scabrifolia. (Franch) Rehd China J Chin Mater Med. 1998;23(7):422–48.
56.
go back to reference Simirgiotis MJ. Antioxidant capacity and HPLC-DAD-MS profiling of Chilean Peumo (Cryptocarya Alba) fruits and comparison with German Peumo (Crataegus monogyna) from Southern Chile. Molecules. 2013;18(2):2061–80.PubMedPubMedCentralCrossRef Simirgiotis MJ. Antioxidant capacity and HPLC-DAD-MS profiling of Chilean Peumo (Cryptocarya Alba) fruits and comparison with German Peumo (Crataegus monogyna) from Southern Chile. Molecules. 2013;18(2):2061–80.PubMedPubMedCentralCrossRef
57.
go back to reference Liu RH, Yu BY, Qiu SX, Zheng D. Comparative analysis of eight major polyphenolic components in leaves of Crataegus L. by HPLC. Chin J Nat Med. 2005;3(3):162–7. Liu RH, Yu BY, Qiu SX, Zheng D. Comparative analysis of eight major polyphenolic components in leaves of Crataegus L. by HPLC. Chin J Nat Med. 2005;3(3):162–7.
58.
go back to reference Wang CH, Wang YX, Liu HJ. Validation and application by HPLC for simultaneous determination of vitexin-2″-O-glucoside, vitexin-2″-O-rhamnoside, rutin, vitexin, and hyperoside. J Pharm Anal. 2011;1(4):291–6.PubMedPubMedCentralCrossRef Wang CH, Wang YX, Liu HJ. Validation and application by HPLC for simultaneous determination of vitexin-2″-O-glucoside, vitexin-2″-O-rhamnoside, rutin, vitexin, and hyperoside. J Pharm Anal. 2011;1(4):291–6.PubMedPubMedCentralCrossRef
59.
go back to reference Martino E, Collina S, Rossi D, Bazzoni D, Gaggeri R, Bracco F, Azzolina O. Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2′′-O-rhamnoside from Crataegus monogyna Jacq.(hawthorn). Phytochem Anal. 2008;19(6):534–40.PubMedCrossRef Martino E, Collina S, Rossi D, Bazzoni D, Gaggeri R, Bracco F, Azzolina O. Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2′′-O-rhamnoside from Crataegus monogyna Jacq.(hawthorn). Phytochem Anal. 2008;19(6):534–40.PubMedCrossRef
60.
go back to reference Cheng S, Qiu F, Huang J, He J. Simultaneous determination of vitexin-2′′-O-glucoside, vitexin-2′′-O-rhamnoside, rutin, and hyperoside in the extract of hawthorn (Crataegus pinnatifida Bge.) Leaves by RP-HPLC with ultraviolet photodiode array detection. J Sep Sci. 2007;30(5):717–21.PubMedCrossRef Cheng S, Qiu F, Huang J, He J. Simultaneous determination of vitexin-2′′-O-glucoside, vitexin-2′′-O-rhamnoside, rutin, and hyperoside in the extract of hawthorn (Crataegus pinnatifida Bge.) Leaves by RP-HPLC with ultraviolet photodiode array detection. J Sep Sci. 2007;30(5):717–21.PubMedCrossRef
61.
go back to reference Kirakosyan A, Seymour E, Kaufman PB, Warber S, Bolling S, Chang SC. Antioxidant capacity of polyphenolic extracts from leaves of Crataegus laevigata and Crataegus monogyna (Hawthorn) subjected to drought and cold stress. J Agric Food Chem. 2003;51(14):3973–6.PubMedCrossRef Kirakosyan A, Seymour E, Kaufman PB, Warber S, Bolling S, Chang SC. Antioxidant capacity of polyphenolic extracts from leaves of Crataegus laevigata and Crataegus monogyna (Hawthorn) subjected to drought and cold stress. J Agric Food Chem. 2003;51(14):3973–6.PubMedCrossRef
62.
go back to reference Han F, Guo Y, Gu H, Li F, Hu B, Yang L. Application of alkyl polyglycoside surfactant in ultrasonic-assisted extraction followed by macroporous resin enrichment for the separation of vitexin-2″-O-rhamnoside and vitexin from Crataegus pinnatifida leaves. J Chromatogr B. 2016;1012–1013:69–78.CrossRef Han F, Guo Y, Gu H, Li F, Hu B, Yang L. Application of alkyl polyglycoside surfactant in ultrasonic-assisted extraction followed by macroporous resin enrichment for the separation of vitexin-2″-O-rhamnoside and vitexin from Crataegus pinnatifida leaves. J Chromatogr B. 2016;1012–1013:69–78.CrossRef
63.
go back to reference Ying X, Wang R, Xu J, Zhang W, Li H, Zhang C, Li F. HPLC determination of eight polyphenols in the leaves of Crataegus pinnatifida Bge. Var. Major. J Chromatogr Sci. 2009;47(3):201–5.PubMedCrossRef Ying X, Wang R, Xu J, Zhang W, Li H, Zhang C, Li F. HPLC determination of eight polyphenols in the leaves of Crataegus pinnatifida Bge. Var. Major. J Chromatogr Sci. 2009;47(3):201–5.PubMedCrossRef
64.
go back to reference Urbonaviciute A, Jakstas V, Kornysova O, Janulis V, Maruska A. Capillary electrophoretic analysis of flavonoids in single-styled hawthorn (Crataegus monogyna Jacq.) Ethanolic extracts. J Chromatogr A. 2006;1112(1–2):339–44.PubMedCrossRef Urbonaviciute A, Jakstas V, Kornysova O, Janulis V, Maruska A. Capillary electrophoretic analysis of flavonoids in single-styled hawthorn (Crataegus monogyna Jacq.) Ethanolic extracts. J Chromatogr A. 2006;1112(1–2):339–44.PubMedCrossRef
65.
go back to reference Kartnig T, Kogl G, Heydel B. Production of flavonoids in cell cultures of Crataegus monogyna. Planta Med. 1993;59(06):537–8.PubMedCrossRef Kartnig T, Kogl G, Heydel B. Production of flavonoids in cell cultures of Crataegus monogyna. Planta Med. 1993;59(06):537–8.PubMedCrossRef
66.
go back to reference Zhang W, Xu M, Yu C, Zhang G, Tang X. Simultaneous determination of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC–ESI-MS/MS. J Chromatogr B. 2010;878(21):1837–44.CrossRef Zhang W, Xu M, Yu C, Zhang G, Tang X. Simultaneous determination of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC–ESI-MS/MS. J Chromatogr B. 2010;878(21):1837–44.CrossRef
67.
go back to reference Li H, Song F, Xing J, Tsao R, Liu Z, Liu S. Screening and structural characterization of α-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS. J Am Soc Mass Spectrom. 2009;20(8):1496–503.PubMedCrossRef Li H, Song F, Xing J, Tsao R, Liu Z, Liu S. Screening and structural characterization of α-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS. J Am Soc Mass Spectrom. 2009;20(8):1496–503.PubMedCrossRef
68.
go back to reference Karar ME, Kuhnert N, UPLC-ESI-Q-TOF-MS. /MS characterization of phenolics from Crataegus monogyna and Crataegus laevigata (Hawthorn) leaves, fruits and their herbal derived drops (Crataegutt Tropfen). J Chem Biol Ther. 2015;1(102):2572–0406. Karar ME, Kuhnert N, UPLC-ESI-Q-TOF-MS. /MS characterization of phenolics from Crataegus monogyna and Crataegus laevigata (Hawthorn) leaves, fruits and their herbal derived drops (Crataegutt Tropfen). J Chem Biol Ther. 2015;1(102):2572–0406.
69.
go back to reference Salminen JP, Karonen M, Lempa K, Liimatainen J, Sinkkonen J, Lukkarinen M, Pihlaja K. Characterisation of proanthocyanidin aglycones and glycosides from rose hips by high-performance liquid chromatography–mass spectrometry, and their rapid quantification together with vitamin C. J Chromatogr A. 2005;1077(2):170–80.PubMedCrossRef Salminen JP, Karonen M, Lempa K, Liimatainen J, Sinkkonen J, Lukkarinen M, Pihlaja K. Characterisation of proanthocyanidin aglycones and glycosides from rose hips by high-performance liquid chromatography–mass spectrometry, and their rapid quantification together with vitamin C. J Chromatogr A. 2005;1077(2):170–80.PubMedCrossRef
70.
go back to reference Karonen M. Plant Proanthocyanidins. Characterization and Quantification by Degradation Methods. HPLC-DAD/ESI-MS and NMR. Annales Universitatis Turkuensis. Ph.D. Dissertation, University of Turku, Turku, Finland. 2007. p. 53. Karonen M. Plant Proanthocyanidins. Characterization and Quantification by Degradation Methods. HPLC-DAD/ESI-MS and NMR. Annales Universitatis Turkuensis. Ph.D. Dissertation, University of Turku, Turku, Finland. 2007. p. 53.
71.
go back to reference Demiray S, Pintado ME, Castro PML. Evaluation of phenolic profiles and antioxidant activities of Turkish medicinal plants: Tilia argentea, Crataegi folium leaves and Polygonum bistorta roots. Int J Pharm Pharm Sci. 2009;3(6):74–9. Demiray S, Pintado ME, Castro PML. Evaluation of phenolic profiles and antioxidant activities of Turkish medicinal plants: Tilia argentea, Crataegi folium leaves and Polygonum bistorta roots. Int J Pharm Pharm Sci. 2009;3(6):74–9.
72.
go back to reference Gonzalez-Jimenez FE, Salazar-Montoya JA, Calva-Calva G, Ramos-Ramírez EG. Phytochemical characterization, in vitro antioxidant activity, and quantitative analysis by micellar electrokinetic chromatography of hawthorn (Crataegus pubescens) fruit. J Food Qual. 2018; 2018: 11. Gonzalez-Jimenez FE, Salazar-Montoya JA, Calva-Calva G, Ramos-Ramírez EG. Phytochemical characterization, in vitro antioxidant activity, and quantitative analysis by micellar electrokinetic chromatography of hawthorn (Crataegus pubescens) fruit. J Food Qual. 2018; 2018: 11.
73.
go back to reference Benabderrahmane W, Lores M, Benaissa O, Lamas JP, de Miguel T, Amrani A, et al. Polyphenolic content and bioactivities of Crataegus oxyacantha L. (Rosaceae). Nat Prod Res. 2019;35(4):627–32.PubMedCrossRef Benabderrahmane W, Lores M, Benaissa O, Lamas JP, de Miguel T, Amrani A, et al. Polyphenolic content and bioactivities of Crataegus oxyacantha L. (Rosaceae). Nat Prod Res. 2019;35(4):627–32.PubMedCrossRef
74.
go back to reference Coklar H, Akbulut M, Kilinc S, Yildirim A, Alhassan I. Effect of freeze, oven and microwave pretreated oven drying on color, browning index, phenolic compounds and antioxidant activity of hawthorn (Crataegus orientalis) fruit. Not Bot Horti Agrobot Cluj-Napoca. 2018;46(2):449–56.CrossRef Coklar H, Akbulut M, Kilinc S, Yildirim A, Alhassan I. Effect of freeze, oven and microwave pretreated oven drying on color, browning index, phenolic compounds and antioxidant activity of hawthorn (Crataegus orientalis) fruit. Not Bot Horti Agrobot Cluj-Napoca. 2018;46(2):449–56.CrossRef
75.
go back to reference Liu P, Yang B, Kallio H. Characterization of phenolic compounds in Chinese hawthorn (Crataegus pinnatifida Bge. Var. Major) fruit by high performance liquid chromatography–electrospray ionization mass spectrometry. Food Chem. 2010;121(4):1188–97.CrossRef Liu P, Yang B, Kallio H. Characterization of phenolic compounds in Chinese hawthorn (Crataegus pinnatifida Bge. Var. Major) fruit by high performance liquid chromatography–electrospray ionization mass spectrometry. Food Chem. 2010;121(4):1188–97.CrossRef
76.
go back to reference Svedstrom U, Vuorela H, Kostiainen R, Huovinen K, Laakso I, Hiltunen R. High-performance liquid chromatographic determination of oligomeric procyanidins from dimers up to the hexamer in hawthorn. J Chromatogr A. 2002;968(1–2):53–60.PubMedCrossRef Svedstrom U, Vuorela H, Kostiainen R, Huovinen K, Laakso I, Hiltunen R. High-performance liquid chromatographic determination of oligomeric procyanidins from dimers up to the hexamer in hawthorn. J Chromatogr A. 2002;968(1–2):53–60.PubMedCrossRef
77.
go back to reference Zhang Z, Chang Q, Zhu M, Huang Y, Ho WK, Chen ZY. Characterization of antioxidants present in hawthorn fruits. J Nutr Biochem. 2001;12(3):144–52.PubMedCrossRef Zhang Z, Chang Q, Zhu M, Huang Y, Ho WK, Chen ZY. Characterization of antioxidants present in hawthorn fruits. J Nutr Biochem. 2001;12(3):144–52.PubMedCrossRef
78.
go back to reference Mraihi F, Hidalgo M, de Pascual-Teresa S, Trabelsi-Ayadi M, Cherif JK. Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arab J Chem. 2015;8(4):570–8.CrossRef Mraihi F, Hidalgo M, de Pascual-Teresa S, Trabelsi-Ayadi M, Cherif JK. Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arab J Chem. 2015;8(4):570–8.CrossRef
79.
go back to reference Wyspianska D, Kucharska AZ, Sokoł-Letowska A, Kolniak-Ostek J. Physico-chemical, antioxidant, and anti-inflammatory properties and stability of hawthorn (Crataegus monogyna Jacq.) Procyanidins microcapsules with inulin and maltodextrin. J Sci Food Agric. 2017;97(2):669–78.PubMedCrossRef Wyspianska D, Kucharska AZ, Sokoł-Letowska A, Kolniak-Ostek J. Physico-chemical, antioxidant, and anti-inflammatory properties and stability of hawthorn (Crataegus monogyna Jacq.) Procyanidins microcapsules with inulin and maltodextrin. J Sci Food Agric. 2017;97(2):669–78.PubMedCrossRef
80.
go back to reference Kumar PP, Kumaravel S, Lalitha C. Screening of antioxidant activity, total phenolics and GC-MS study of Vitex negundo. Afr J Biochem Res. 2010;4(7):191–5. Kumar PP, Kumaravel S, Lalitha C. Screening of antioxidant activity, total phenolics and GC-MS study of Vitex negundo. Afr J Biochem Res. 2010;4(7):191–5.
82.
go back to reference Dickson RA, Houghton PJ, Hylands PJ. Antibacterial and antioxidant cassane diterpenoids from Caesalpinia Benthamiana. Phytochem. 2007;68(10):1436–41.CrossRef Dickson RA, Houghton PJ, Hylands PJ. Antibacterial and antioxidant cassane diterpenoids from Caesalpinia Benthamiana. Phytochem. 2007;68(10):1436–41.CrossRef
83.
go back to reference Negi PS. Plant extracts for the control of bacterial growth: efficacy, stability and safety issues for food application. Int J Food Microbiol. 2012;156(1):7–17.PubMedCrossRef Negi PS. Plant extracts for the control of bacterial growth: efficacy, stability and safety issues for food application. Int J Food Microbiol. 2012;156(1):7–17.PubMedCrossRef
84.
go back to reference Safapour S, Sadeghi-Kiakhani M, Eshaghloo-Galugahi S, Extraction. Dyeing, and antibacterial properties of Crataegus elbursensis fruit natural dye on wool yarn. Fibers Polym. 2018;19:1428–34.CrossRef Safapour S, Sadeghi-Kiakhani M, Eshaghloo-Galugahi S, Extraction. Dyeing, and antibacterial properties of Crataegus elbursensis fruit natural dye on wool yarn. Fibers Polym. 2018;19:1428–34.CrossRef
85.
go back to reference Alami M, Ghorban M. Evaluation of total phenolic, flavonoid, anthocyanin compounds, antibacterial and antioxidant activity of hawthorn (Crataegus Elbursensis) fruit acetonic extract. J Rafsanjan Univ Med Sci. 2014;13(1):53–66. Alami M, Ghorban M. Evaluation of total phenolic, flavonoid, anthocyanin compounds, antibacterial and antioxidant activity of hawthorn (Crataegus Elbursensis) fruit acetonic extract. J Rafsanjan Univ Med Sci. 2014;13(1):53–66.
86.
go back to reference Saha P, Rahman FI, Hussain F, Rahman SM, Rahman MM. Antimicrobial diterpenes: recent development from natural sources. Front Pharmacol. 2022;12:820312.PubMedPubMedCentralCrossRef Saha P, Rahman FI, Hussain F, Rahman SM, Rahman MM. Antimicrobial diterpenes: recent development from natural sources. Front Pharmacol. 2022;12:820312.PubMedPubMedCentralCrossRef
87.
go back to reference Kuczkowiak U, Petereit F, Nahrstedt A. Hydroxycinnamic acid derivatives obtained from a commercial Crataegus Extract and from authentic Crataegus spp. Sci Pharm. 2014;82(4):835–46.PubMedPubMedCentralCrossRef Kuczkowiak U, Petereit F, Nahrstedt A. Hydroxycinnamic acid derivatives obtained from a commercial Crataegus Extract and from authentic Crataegus spp. Sci Pharm. 2014;82(4):835–46.PubMedPubMedCentralCrossRef
Metadata
Title
Crataegus pentagyna willd. Fruits, leaves and roots: phytochemicals, antioxidant and antimicrobial potentials
Authors
Akram Taleghani
Samira Eghbali
Roya Moghimi
Majid Mokaber-Esfahani
Publication date
01-12-2024
Publisher
BioMed Central
Published in
BMC Complementary Medicine and Therapies / Issue 1/2024
Electronic ISSN: 2662-7671
DOI
https://doi.org/10.1186/s12906-024-04430-4

Other articles of this Issue 1/2024

BMC Complementary Medicine and Therapies 1/2024 Go to the issue