Identification of phenolic compounds in the buds of Algerian Pistacia atlantica desf. Subsp. atlantica by antioxidant activity guided fractionation
-
Fethi Toul
, Sonia Moussouni
, Nacera Ghembaza , Amel Zitouni , Amina Djendar , Fawzia Atik-Bekkara and Eugenius Kokkalou
Abstract
Objectives
A bio-guided selection and identification of the most active compounds obtained from Algerian Pistacia atlantica desf. Subsp. atlantica.
Methods
An antioxidant activity guided fractionation was performed on buds’ extract using extensive chromatographic and spectroscopic techniques. The antioxidant potentials of isolated compounds and other unpurified fractions were evaluated against DPPH radicals using TLC plates and test tubes.
Results
The results showed that all isolated compounds and fractions exhibited eminent DPPH scavenging potential. Two coumarins (7-ethoxycoumarin and 7-hydroxy-5-methoxycoumarin) and two flavonoids (3′,5,7-trihydroxy-4′-methoxyflavanone and 5,6,7,4′-tetrahydroxyflavonol-3-O-rutinoside) were isolated for the first times from the titled subspecies.
Conclusions
These results confirm that the species of P. atlantica is far from being exhausted of active compounds, especially polyphenols.
-
Research funding: None declared.
-
Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission.
-
Competing interests: Authors state no conflict of interest.
-
Informed consent: Not applicable.
-
Ethical approval: The local Institutional Review Board deemed the study exempt from review.
References
1. El Zerey-Belaskri, A, Ribeiro, T, Alcaraz, ML, Zerey, WEL, Castro, S, Loureiro, J, et al.. Molecular characterization of Pistacia atlantica Desf. subsp. atlantica (Anacardiaceae) in Algeria: Genome size determination, chromosome count and genetic diversity analysis using SSR markers. Sci Hortic 2018;227:278–87. https://doi.org/10.1016/j.scienta.2017.09.016.Search in Google Scholar
2. Sifi, I, Gourine, N, Gaydou, EM, Yousfi, M. Chemotypes of essential oil of unripe galls of Pistacia atlantica Desf. from Algeria. Nat Prod Res 2015;29:1945–9. https://doi.org/10.1080/14786419.2015.1012164.Search in Google Scholar
3. Hatamnia, AA, Abbaspour, N, Darvishzadeh, R. Antioxidant activity and phenolic profile of different parts of Bene (Pistacia atlantica subsp. kurdica) fruits. Food Chem 2014;145:306–11. https://doi.org/10.1016/j.foodchem.2013.08.031.Search in Google Scholar
4. Toul, F, Belyagoubi-Benhammou, N, Zitouni, A, Atik-Bekkara, F. Antioxidant activity and phenolic profile of different organs of Pistacia atlantica Desf. subsp. atlantica from Algeria. Nat Prod Res 2017;31:718–23. https://doi.org/10.1080/14786419.2016.1217205.Search in Google Scholar
5. Rauf, A, Patel, S, Uddin, G, Siddiqui, BS, Ahmad, B, Muhammad, N, et al.. Phytochemical, ethnomedicinal uses and pharmacological profile of genus Pistacia. Biomed Pharmacother 2017;86:393–404. https://doi.org/10.1016/j.biopha.2016.12.017.Search in Google Scholar
6. Mahmoudvand, H, Kheirandish, F, Ghasemi Kia, M, Tavakoli Kareshk, A, Yarahmadi, M. Chemical composition, protoscolicidal effects and acute toxicity of Pistacia atlantica Desf. fruit extract. Nat Prod Res 2016;30:1208–11. https://doi.org/10.1080/14786419.2015.1046868.Search in Google Scholar
7. Uddin, G, Ismail, Rauf, A, Raza, M, Khan, H, Nasruddin, et al.. Urease inhibitory profile of extracts and chemical constituents of Pistacia atlantica ssp. cabulica Stocks. Nat Prod Res 2016;30:1411–6. https://doi.org/10.1080/14786419.2015.1062378.Search in Google Scholar
8. Rigane, G, Ghazghazi, H, Aouadhi, C, Ben Salem, R, Nasr, Z. Phenolic content, antioxidant capacity and antimicrobial activity of leaf extracts from Pistacia atlantica. Nat Prod Res 2017;31:696–9. https://doi.org/10.1080/14786419.2016.1212035.Search in Google Scholar
9. El Zerey-Belaskri, A, Benhassaini, H. Morphological leaf variability in natural populations of Pistacia atlantica Desf. subsp. atlantica along climatic gradient: new features to update Pistacia atlantica subsp. atlantica key. Int J Biometeorol 2016;60:577–89. https://doi.org/10.1007/s00484-015-1052-4.Search in Google Scholar
10. Sánchez‐Moreno, C, Larrauri, JA, Saura‐Calixto, F. A procedure to measure the antiradical efficiency of polyphenols. J Sci Food Agric 1998;76:270–6.10.1002/(SICI)1097-0010(199802)76:2<270::AID-JSFA945>3.0.CO;2-9Search in Google Scholar
11. Mokgotho, MP, Gololo, SS, Masoko, P, Mdee, LK, Mbazima, V, Shai, LJ, et al.. Isolation and chemical structural characterisation of a compound with antioxidant activity from the roots of Senna italica. Evidence-Based Complement Altern Med. 2013;2013. https://doi.org/10.1155/2013/519174.Search in Google Scholar PubMed PubMed Central
12. Fisher, MB, Jackson, D, Kaerner, A, Wrighton, SA, Borel, AG. Characterization by liquid chromatography-nuclear magnetic resonance spectroscopy and liquid chromatography-mass spectrometry of two coupled oxidative-conjugative metabolic pathways for 7-ethoxycoumarin in human liver microsomes treated with alamethicin. Drug Metab Dispos 2002;30:270–5. https://doi.org/10.1124/dmd.30.3.270.Search in Google Scholar PubMed
13. Maltese, F, Erkelens, C, van der Kooy, F, Choi, YH, Verpoorte, R. Identification of natural epimeric flavanone glycosides by NMR spectroscopy. Food Chem 2009;116:575–9. https://doi.org/10.1016/j.foodchem.2009.03.023.Search in Google Scholar
14. Darmawan, A, Kosela, S, Kardono, LBS, Syah, YM. Scopoletin, a coumarin derivative compound isolated from Macaranga gigantifolia Merr. J Appl Pharmaceut Sci 2012;2:175.Search in Google Scholar
15. Ersöz, T, Ivancheva, S, Akbay, P, Sticher, O, Çalış, İ. Iridoid and phenylethanoid glycosides from Phlomis tuberosa L. Z Naturforsch C Biosci 2001;56:695–8. https://doi.org/10.1515/znc-2001-9-1004.Search in Google Scholar PubMed
16. Yassa, N, Saeidnia, S, Pirouzi, R, Akbaripour, M, Shafiee, A. Three phenolic glycosides and immunological properties of Achillea millefolium from Iran, population of Golestan. DARU J Pharm Sci 2007;15:49–52.Search in Google Scholar
17. Güvenalp, Z, Kilic, N, Kazaz, C, Kaya, Y, Demi̇rezer, LÖ. Chemical constituents of Galium tortumense. Turk J Chem 2006;30:515–23.Search in Google Scholar
18. Alara, OR, Abdurahman, NH, Ukaegbu, CI. Extraction of phenolic compounds: a review. Curr Res Food Sci 2021;4:200–14. https://doi.org/10.1016/j.crfs.2021.03.011.Search in Google Scholar PubMed PubMed Central
19. Mittal, R, Gupta, RL. In vitro antioxidant activity of piperine. Methods Find Exp Clin Pharmacol 2000;22:271–4. https://doi.org/10.1358/mf.2000.22.5.796644.Search in Google Scholar PubMed
20. Shaw, C, Chen, C, Hsu, C, Chen, C, Tsai, Y. Antioxidant properties of scopoletin isolated from Sinomonium acutum. Phyther Res 2003;17:823–5. https://doi.org/10.1002/ptr.1170.Search in Google Scholar PubMed
21. Singh, R, Singh, B, Singh, S, Kumar, N, Kumar, S, Arora, S. Umbelliferone–An antioxidant isolated from Acacia nilotica (L.) Willd. ex. Del. Food Chem 2010;120:825–30. https://doi.org/10.1016/j.foodchem.2009.11.022.Search in Google Scholar
22. Malik, A, Kushnoor, A, Saini, V, Singhal, S, Kumar, S, Yadav, YC. In vitro antioxidant properties of Scopoletin. J Chem Pharmaceut Res 2011;3:659–65.Search in Google Scholar
23. Mogana, R, Teng-Jin, K, Wiart, C. Anti-inflammatory, anticholinesterase, and antioxidant potential of scopoletin isolated from Canarium patentinervium Miq.(Burseraceae Kunth). Evid Base Compl Alternative Med 2013;2013. https://doi.org/10.1155/2013/734824.Search in Google Scholar PubMed PubMed Central
24. Parhiz, H, Roohbakhsh, A, Soltani, F, Rezaee, R, Iranshahi, M. Antioxidant and anti‐inflammatory properties of the citrus flavonoids hesperidin and hesperetin: an updated review of their molecular mechanisms and experimental models. Phyther Res 2015;29:323–31. https://doi.org/10.1002/ptr.5256.Search in Google Scholar PubMed
25. Roowi, S, Crozier, A, Hussin, Z, Rahman, ZA. On-line high-performance liquid chromatography analysis of the antioxidant activity of phenolic compounds in selected tropical citrus. J Trop Agric Food Sci 2016;44:81–94.Search in Google Scholar
26. Yang, J, Guo, J, Yuan, J, Jayaraman, R, Subramani, S, Abdullah, SHS, et al.. Antihyperglycemic effect of hesperetin, a citrus flavonoid, extenuates hyperglycemia and exploring the potential role in antioxidant and antihyperlipidemic in streptozotocin-induced diabetic rats. Biomed Pharmacother 2018;41:98–106. https://doi.org/10.1016/j.biopha.2017.10.102.Search in Google Scholar PubMed
27. Wolfe, KL, Liu, RH. Structure− activity relationships of flavonoids in the cellular antioxidant activity assay. J Agric Food Chem 2008;56:8404–11. https://doi.org/10.1021/jf8013074.Search in Google Scholar PubMed
28. Choi, Y, Jeong, H-S, Lee, J. Antioxidant activity of methanolic extracts from some grains consumed in Korea. Food Chem 2007;103:130–8. https://doi.org/10.1016/j.foodchem.2006.08.004.Search in Google Scholar
29. Thuong, PT, Hung, TM, Ngoc, TM, Ha, DT, Min, BS, Kwack, SJ, et al.. Antioxidant activities of coumarins from Korean medicinal plants and their structure–activity relationships. Phyther Res An Int J Devoted to Pharmacol Toxicol Eval Nat Prod Deriv 2010;24:101–6. https://doi.org/10.1002/ptr.2890.Search in Google Scholar PubMed
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/jcim-2021-0336).
© 2021 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Swarna Prashana – faith in the embrace of research
- A review on the concept of aging in Ayurveda literature
- Ethno-pharmacology of Asaroon (Asarum europaeum L.) with special reference to Unani System of Medicine
- Is Trikatu an ayurvedic formulation effective for the management of flu-like illness? A narrative review
- The anti-cancer properties of neem (Azadirachta indica) through its antioxidant activity in the liver: its pharmaceutics and toxic dosage forms. A literature review
- The role of acupuncture for myofascial pain syndrome (MPS) in interventional pain management
- Research Articles
- Identification of phenolic compounds in the buds of Algerian Pistacia atlantica desf. Subsp. atlantica by antioxidant activity guided fractionation
- Optimization of water-based ultrasonic-microwave assisted extraction (UMAE) of bioactive compounds from Garcinia mangostana pericarp
- Proximate analysis, HPTLC finger print analysis and multi spectrometric analysis of Strychnos nux-vomica nuts
- Amelioration of sodium fluoride induced oxidative stress by Cynometra travancorica Bedd in mice
- The effects of saffron petals and damask rose petals on biochemical and inflammatory measurements
- Ethanolic extract of Achillea wilhelmsii C. Koch improves pulmonary function and inflammation in LPS-induced acute lung injury mice
- Interaction between properties of commercial Australian honey and saliva: in vitro exploratory study of a potential mechanism in the treatment of oral mucositis
- The potential of immature poken (Citrus reticulata) extract in the weight management, lipid and glucose metabolism
- Effect of the beta-adrenergic blockade on intestinal lactate production and glycogen concentration in dogs infused with hexoses
- Investigating the effect of the Teucrium polium aqueous extract on the liver of the streptozotocin-induced diabetic rats
- Synergistic effects of high-intensity interval training (HIIT) and intake of nettle on serum levels of chemerin and beta cells function in type 2 diabetic rats
- The effect of Cinnamomum cassia extract on oxidative stress in the liver and kidney of STZ-induced diabetic rats
- Protective role of Sterculia tragacantha aqueous extract on pancreatic gene expression and oxidative stress parameters in streptozotocin-induced diabetic rats
- Ameliorating activity of polyphenolic-rich extracts of Basella rubra L. leaves on pancreatic β-cell dysfunction in streptozotocin-induced diabetic rats
- Amelioration of related complications by the combined usage of Gymnadenia orchidis Lindl and pumpkin seed in type 2 diabetic mice
- The effect of Madhumeha Kusumakar Rasa – an Ayurved medicine – in insulin resistance
- Anti-obesity effects of the n-butanol fraction of the methanolic leaf extract of Artemisia campestris from Tunisian pharmacopeia in male Wistar rats
- Compensatory depression of arterial pressure and reversal of ECG abnormalities by Annona muricata and Curcuma longa in hypertensive Wistar rats
- Preventing SARS-CoV-2 transmission in the emergency department by implementing a separate pathway for patients with respiratory conditions
- Clinical significance of serum gonadotropin and androgen levels among Egyptian overweight/obese pubertal girls
- Preference between serum homocysteine and urinary periostin as early predictive biomarkers of renal dysfunction among uncontrolled diabetics
- Mizaj assessment in multiple sclerosis patients based on Persian Medicine
- Immediate effects of the practise of Sheethali pranayama on heart rate and blood pressure parameters in healthy volunteers
- Effects of 12 sessions of steam bath intervention on spirometry parameters among healthy adult volunteers
- The effects of psychological counseling and acupressure based on couple therapy procedure for alleviation of vomiting and nausea in pregnant women in Iran country
- “The immediate effect of neutral spinal compress on heart rate variability in hypertensive individuals”
- Effect of whole-body vibration after a resistance exercise bout on heart rate variability in hypertensive population
- Wet-cupping on calf muscles in polycystic ovary syndrome: a quasi-experimental study
- Auricular field nerve stimulation using the NSS-2 BRIDGE® device as an alternative to opioids following kidney donor surgery
- Evaluation of general body temperament and uterine dystemperament in amenorrhoea: a cross-sectional analytical study
- Short Communication
- Isolation, characterization, and antimicrobial activity of communic acid from Juniperus phoenicea
- Letter to the Editor
- Can silymarin ameliorate β-thalassemia major-induced osteopenia/osteoporosis?
- Case Reports
- Management of psoriasis with Ayurveda Panchakarma and Manibhadragula as Shodhana Rasayana – a case report
- Psychogenic pseudo-myasthenic ptosis – management with ayurvedic medicines and Smriti meditation
- Education Forum
- Tongue stretching: technique and clinical proposal
- Simulation-based ventilatory training for the caregivers at primary and rural health care workers in Central India for dealing with COVID-19 pandemic: recommendations
Articles in the same Issue
- Frontmatter
- Reviews
- Swarna Prashana – faith in the embrace of research
- A review on the concept of aging in Ayurveda literature
- Ethno-pharmacology of Asaroon (Asarum europaeum L.) with special reference to Unani System of Medicine
- Is Trikatu an ayurvedic formulation effective for the management of flu-like illness? A narrative review
- The anti-cancer properties of neem (Azadirachta indica) through its antioxidant activity in the liver: its pharmaceutics and toxic dosage forms. A literature review
- The role of acupuncture for myofascial pain syndrome (MPS) in interventional pain management
- Research Articles
- Identification of phenolic compounds in the buds of Algerian Pistacia atlantica desf. Subsp. atlantica by antioxidant activity guided fractionation
- Optimization of water-based ultrasonic-microwave assisted extraction (UMAE) of bioactive compounds from Garcinia mangostana pericarp
- Proximate analysis, HPTLC finger print analysis and multi spectrometric analysis of Strychnos nux-vomica nuts
- Amelioration of sodium fluoride induced oxidative stress by Cynometra travancorica Bedd in mice
- The effects of saffron petals and damask rose petals on biochemical and inflammatory measurements
- Ethanolic extract of Achillea wilhelmsii C. Koch improves pulmonary function and inflammation in LPS-induced acute lung injury mice
- Interaction between properties of commercial Australian honey and saliva: in vitro exploratory study of a potential mechanism in the treatment of oral mucositis
- The potential of immature poken (Citrus reticulata) extract in the weight management, lipid and glucose metabolism
- Effect of the beta-adrenergic blockade on intestinal lactate production and glycogen concentration in dogs infused with hexoses
- Investigating the effect of the Teucrium polium aqueous extract on the liver of the streptozotocin-induced diabetic rats
- Synergistic effects of high-intensity interval training (HIIT) and intake of nettle on serum levels of chemerin and beta cells function in type 2 diabetic rats
- The effect of Cinnamomum cassia extract on oxidative stress in the liver and kidney of STZ-induced diabetic rats
- Protective role of Sterculia tragacantha aqueous extract on pancreatic gene expression and oxidative stress parameters in streptozotocin-induced diabetic rats
- Ameliorating activity of polyphenolic-rich extracts of Basella rubra L. leaves on pancreatic β-cell dysfunction in streptozotocin-induced diabetic rats
- Amelioration of related complications by the combined usage of Gymnadenia orchidis Lindl and pumpkin seed in type 2 diabetic mice
- The effect of Madhumeha Kusumakar Rasa – an Ayurved medicine – in insulin resistance
- Anti-obesity effects of the n-butanol fraction of the methanolic leaf extract of Artemisia campestris from Tunisian pharmacopeia in male Wistar rats
- Compensatory depression of arterial pressure and reversal of ECG abnormalities by Annona muricata and Curcuma longa in hypertensive Wistar rats
- Preventing SARS-CoV-2 transmission in the emergency department by implementing a separate pathway for patients with respiratory conditions
- Clinical significance of serum gonadotropin and androgen levels among Egyptian overweight/obese pubertal girls
- Preference between serum homocysteine and urinary periostin as early predictive biomarkers of renal dysfunction among uncontrolled diabetics
- Mizaj assessment in multiple sclerosis patients based on Persian Medicine
- Immediate effects of the practise of Sheethali pranayama on heart rate and blood pressure parameters in healthy volunteers
- Effects of 12 sessions of steam bath intervention on spirometry parameters among healthy adult volunteers
- The effects of psychological counseling and acupressure based on couple therapy procedure for alleviation of vomiting and nausea in pregnant women in Iran country
- “The immediate effect of neutral spinal compress on heart rate variability in hypertensive individuals”
- Effect of whole-body vibration after a resistance exercise bout on heart rate variability in hypertensive population
- Wet-cupping on calf muscles in polycystic ovary syndrome: a quasi-experimental study
- Auricular field nerve stimulation using the NSS-2 BRIDGE® device as an alternative to opioids following kidney donor surgery
- Evaluation of general body temperament and uterine dystemperament in amenorrhoea: a cross-sectional analytical study
- Short Communication
- Isolation, characterization, and antimicrobial activity of communic acid from Juniperus phoenicea
- Letter to the Editor
- Can silymarin ameliorate β-thalassemia major-induced osteopenia/osteoporosis?
- Case Reports
- Management of psoriasis with Ayurveda Panchakarma and Manibhadragula as Shodhana Rasayana – a case report
- Psychogenic pseudo-myasthenic ptosis – management with ayurvedic medicines and Smriti meditation
- Education Forum
- Tongue stretching: technique and clinical proposal
- Simulation-based ventilatory training for the caregivers at primary and rural health care workers in Central India for dealing with COVID-19 pandemic: recommendations