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Open Access 01-12-2022 | Original contribution

Flavonoid profile and antioxidant properties of Algerian common yew (Taxus baccata L.)

Authors: Mohamed Bekhouche, Roukia Benyammi, Majda Khelifi Slaoui, Soumia Krimat, Cedric Paris, Lakhdar Khelifi, Abdelkader Morsli

Published in: Clinical Phytoscience | Issue 1/2022

Abstract

Background

In humans, various diseases are associated with the accumulation of free radicals. The antioxidants can scavenge free radicals and reduce their impact; thus, the search for effective natural antioxidants of plant origin is indispensable. The present study aims to determine, for the first time, the flavonoid compounds profile and to investigate the free radical scavenging and antioxidant properties of the methanolic extract of Taxus baccata L. from Algeria.

Methods

The determination of the flavonoid compound profile of the methanolic extract of Taxus baccata L. was established using high-performance liquid chromatography with diode-array detection coupled to electrospray ionization tandem mass spectrometry (HPLC–DAD–ESI–MS/MS). The total flavonoid content (TFC) was performed according to the aluminum chloride colorimetric method, while the free radical scavenging and antioxidant activities were carried out using three methods, namely 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay, 2,2'-azino-bis3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical assay and ferric reducing antioxidant power (FRAP) Assay.

Results

A total of 26 compounds including flavon-3-ols, flavanonols, flavones, flavonols and bioflavonoids were characterized and identifiedusing HPLC–DAD–ESI–MS/MS analysis, five were reported for the first time such as taxifolin, apigenin, apigenin 7-O-glucoside, isorhamnetin 3-O-rutinoside and robustaflavone. The plant extract exhibited high total flavonoid content (TFC = 204.26 ± 6.02 mg RE/g dry extract) which corresponded to its strong radical scavenging activities [(DPPH IC₅₀ = 35.31 ± 0.29 µg/ml and ABTS IC₅₀ = 8.27 ± 0.52 µg/ml)] as compared to the synthetic antioxidant BHT [(DPPH IC₅₀ = 78.96 ± 5.70 µg/ml and ABTS IC₅₀ = 13.56 ± 0.06 µg/ml)]. However, the methanolic extract of T. baccata showed the lowest ferric reducing ability as compared to the positive controls (BHT, BHA, ascorbic acid, trolox and quercetin).

Conclusion

Our results imply that the Taxus Baccata L. might be a potential source for the isolation of natural antioxidant compounds.

Coughlan P, Hook ILI, Kilmartin L, Hodkinson TR. Phylogenetics of Taxus using the internal transcribed spacers of nuclear ribosomal DNA and plastid trnL-F regions. Horticulturae. 2020. https://doi.org/10.3390/horticulturae6010019.CrossRef

García JC. Biogeografía del tejo (Taxus baccata L.) en el norte de África. In: Generalitat Valenciana, Conselleria de Territori i Habitatge, editors. El tejo en el Mediterráneo occidental: Jornadas Internacionales sobre el tejo y las tejeras en el Mediterráneo occidental; 2007. p. 177–183.

Juyal D, hawani V, Thaledi S, Joshi M. Ethnomedical properties of Taxus Wallichiana Zucc. (Himalayan yew). J Tradit Complement Med. 2014;4:159–61. https://doi.org/10.4103/2225-4110.136544.

Durak ZE, Büber S, Devrim E, Kocaoğlu H, Durak İ. Aqueous extract from Taxus baccata inhibits adenosine deaminase activity significantly in cancerous and non cancerous human gastric and colon tissues. Pharmacogn Mag. 2014;10:214–6.CrossRef

Milutinović MG, Stanković MS, Cvetković DM, Topuzović MD, Mihailović VB, Marković SD. Antioxidant and anticancer properties of leaves and seed cones from European yew (Taxus baccata L). Arch Biol Sci. 2015;67:525–34.CrossRef

Epifanio NMdeM, Cavalcanti LRI, Santos KF dos, Duarte PSC, Kachlicki P, Ożarowski M, et al. Chemical characterization and in vivo antioxidant activity of parsley (Petroselinum crispum). aqueous extract Food Funct. 2020;11:5346–56.CrossRef

Gülçin İ. Antioxidant activity of food constituents: an overview. Arch Toxicol. 2012;86:345–91.CrossRef

Rahman MdM, Hossain ASMS, Mostofa MdG, Khan MA, Ali R, Mosaddik A, et al. Evaluation of anti-ROS and anticancer properties of Tabebuia pallida L. Leaves. Clin Phytosci. 2019;5:17. https://doi.org/10.1186/s40816-019-0111-5.

Bhatti JS, Bhatti GK, Reddy PH. Mitochondrial dysfunction and oxidative stress in metabolic disorders — A step towards mitochondria based therapeutic strategies. Biochim Biophys Acta Mol Basis Dis. 2017;1863:1066–77.CrossRef

10.

Islam MdZ, Hossain MdT, Hossen F, Mukharjee SK, Sultana N, Paul SC. Evaluation of antioxidant and antibacterial activities of Crotalaria pallida stem extract. Clin Phytosci. 2018;4:8. https://doi.org/10.1186/s40816-018-0066-y.

11.

Tan BL, Norhaizan ME, Liew W-P-P, Sulaiman Rahman H. Antioxidant and oxidative stress: A mutual interplay in age-related diseases. Front Pharmacol. 2018;9:1162. https://doi.org/10.3389/fphar.2018.01162.CrossRefPubMedPubMedCentral

12.

Xu D-P, Li Y, Meng X, Zhou T, Zhou Y, Zheng J, et al. Natural antioxidants in foods and medicinal plants: extraction, assessment and resources. Int J Mol Sci. 2017;18:96. https://doi.org/10.3390/ijms18010096.CrossRefPubMedCentral

13.

Luo S, Zhang X, Zhang X, Zhang L. Extraction, identification and antioxidant activity of proanthocyanidins from Larix gmelinii Bark. Nat Prod Res. 2014;28:1116–20.CrossRef

14.

Karak P. Biological activities of flavonoids: an overview. Int J Pharm Sci Res. 2019;10:1567–74.

15.

Panche AN, Diwan AD, Chandra SR. Flavonoids: an overview. J Nutr Sci. 2016;5:47. https://doi.org/10.1017/jns.2016.41.CrossRef

16.

Alseekh S, Perez de Souza L, Benina M, Fernie AR. The style and substance of plant flavonoid decoration; towards defining both structure and function. Phytochemistry. 2020;174:112347. https://doi.org/10.1016/j.phytochem.2020.112347.CrossRefPubMed

17.

Pietta PG. Flavonoids as antioxidants. J Nat Prod. 2000;63:1035–42.CrossRef

18.

Andrade AWL, Machado KdaC, Machado KdaC, Figueiredo DDR, David JM, Islam MT, et al. In vitro antioxidant properties of the biflavonoid agathisflavone. Chem Cent J. 2018;12:75. https://doi.org/10.1186/s13065-018-0443-0.CrossRefPubMedPubMedCentral

19.

Verma ML, Sharma S, Saini R, Rani V, Kushwaha R. Bioflavonoids: Synthesis, functions and biotechnological applications. In: Verma ML, Chandel AK, editors. Biotechnological Production of Bioactive Compounds. Elsevier; 2020. p. 69–105.

20.

Krauze-Baranowska M, Wiwart M. Antifungal activity of biflavones from Taxus baccata and Ginkgo biloba. Z Naturforsch C J Biosci. 2003;58:65. https://doi.org/10.1515/znc-2003-1-212.CrossRefPubMed

21.

Erdemoglu N, Sener B, Choudhary MI. Bioactivity of lignans from Taxus baccata. Z Naturforsch C J Biosci. 2004;59:494–8.CrossRef

22.

Es-Safi N-E, Ghidouche S, Ducrot PH. Flavonoids: hemisynthesis, reactivity, characterization and free radical scavenging activity. Mol. 2007;12:2228. https://doi.org/10.3390/12092228.CrossRef

23.

Sánchez-Gutiérrez JA, Moreno-Lorenzana D, Álvarez-Bernal D, Rodríguez-Campos J, Medina-Medrano JR. Phenolic profile, antioxidant and anti-proliferative activities of methanolic extracts from Asclepias linaria Cav. leaves. Mol. 2019;25:54. https://doi.org/10.3390/molecules25010054.CrossRef

24.

Larbat R, Paris C, Le Bot J, Adamowicz S. Phenolic characterization and variability in leaves, stems and roots of Micro-Tom and patio tomatoes, in response to nitrogen limitation. Plant Sci. 2014;224:62–73.CrossRef

25.

Desta ZY, Cherie DA. Determination of antioxidant and antimicrobial activities of the extracts of aerial parts of Portulaca quadrifida. Chem Cent J. 2018;12:146. https://doi.org/10.1186/s13065-018-0514-2.CrossRefPubMedPubMedCentral

26.

Patra JK, Kim SH, Baek K-H. Antioxidant and free radical-scavenging potential of essential oil from Enteromorpha linza L prepared by microwave-assisted hydrodistillation. J Food Biochem. 2015;39:80–90.CrossRef

27.

Minnelli C, Laudadio E, Galeazzi R, Rusciano D, Armeni T, Stipa P, et al. Synthesis, characterization and antioxidant properties of a new lipophilic derivative of edaravone. Antioxid. 2019;8:258. https://doi.org/10.3390/antiox8080258.CrossRef

28.

Niroula A, Khatri S, Khadka D, Timilsina R. Total phenolic contents and antioxidant activity profile of selected cereal sprouts and grasses. Int J Food Pro. 2019;22:427–37.CrossRef

29.

Le Grandois J, Guffond D, Hamon E, Marchioni E, Werner D. Combined microplate-ABTS and HPLC-ABTS analysis of tomato and pepper extracts reveals synergetic and antagonist effects of their lipophilic antioxidative components. Food Chem. 2017;223:62–71.CrossRef

30.

Aguiar J, Gonçalves JL, Alves VL, Câmara JS. Chemical fingerprint of free polyphenols and antioxidant activity in dietary fruits and vegetables using a non-targeted approach based on QuEChERS ultrasound-assisted extraction combined with UHPLC-PDA. Antioxid. 2020;9:305. https://doi.org/10.3390/antiox9040305.CrossRef

31.

Youn JS, Kim Y-J, Na HJ, Jung HR, Song CK, Kang SY, et al. Antioxidant activity and contents of leaf extracts obtained from Dendropanax morbifera LEV are dependent on the collecting season and extraction conditions. Food Sci Biotechnol. 2018;28:201–7.CrossRef

32.

Jaiswal R, Karar MGE, Gadir HA, Kuhnert N. Identification and characterisation of phenolics from Ixora coccinea L (Rubiaceae) by liquid chromatography multi-stage mass spectrometry. Phytochem Anal. 2014;25:567–76.CrossRef

33.

Jaiswal R, Jayasinghe L, Kuhnert N. Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS. J Mass Spectrom. 2012;47:502–15.CrossRef

34.

Chen G, Li X, Saleri FD, Guo M. Analysis of flavonoids in rhamnus davurica and its antiproliferative activities. Mol. 2016;21:1275. https://doi.org/10.3390/molecules21101275.CrossRef

35.

Lee S-H, Kim H-W, Lee M-K, Kim YJ, Asamenew G, Cha Y-S, et al. Phenolic profiling and quantitative determination of common sage (Salvia plebeia R. Br.) by UPLC-DAD-QTOF/MS. Eur Food Res Technol. 2018;244:1637–46.CrossRef

36.

Marengo A, Maxia A, Sanna C, Mandrone M, Bertea CM, Bicchi C, et al. Intra-specific variation in the little-known Mediterranean plant Ptilostemon casabonae (L.) Greuter analysed through phytochemical and biomolecular markers. Phytochemistry. 2019;161:21–7.CrossRef

37.

Vignolini P, Gehrmann B, Melzig MF, Borsacchi L, Scardigli A, Romani A. Quality control and analytical test method for Taxus baccata tincture preparation. Nat Prod Commun. 2012;7:875–7.PubMed

38.

Krauze-Baranowska M. Flavonoids from the genus Taxus. Z Naturforsch C J Biosci. 2004;59:43–7.CrossRef

39.

Davis BD, Brodbelt JS. Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry. J Am Soc Mass Spectrom. 2004;15:1287–99.CrossRef

40.

Jang GH, Kim HW, Lee MK, Jeong SY, Bak AR, Lee DJ, et al. Characterization and quantification of flavonoid glycosides in the Prunus genus by UPLC-DAD-QTOF/MS. Saudi J Biol Sci. 2018;25:1622–31.CrossRef

41.

Lin L-Z, Harnly JM. A screening method for the identification of glycosylated flavonoids and other phenolic compounds using a standard analytical approach for all plant materials. J Agric Food Chem. 2007;55:1084–96.CrossRef

42.

Wang G, Yao S, Zhang X-X, Song H. Rapid screening and structural characterization of antioxidants from the extract of Selaginella doederleinii Hieron with DPPH-UPLC-Q-TOF/MS Method. Int J Anal Chem. 2015;2015:849769. https://doi.org/10.1155/2015/849769.CrossRefPubMedPubMedCentral

43.

Senol FS, Orhan IE, Ustun O. In vitro cholinesterase inhibitory and antioxidant effect of selected coniferous tree species. Asian Pac J Trop Med. 2015;8:269–75.CrossRef

44.

Becker MM, Nunes GS, Ribeiro DB, Silva FEPS, Catanante G, Marty J-L, et al. Determination of the antioxidant capacity of red fruits by miniaturized spectrophotometry assays. J Braz Chem Soc. 2019;30:1108–14.

45.

Ilyasov IR, Beloborodov VL, Selivanova IA. Three ABTS•+ radical cation-based approaches for the evaluation of antioxidant activity: fast- and slow-reacting antioxidant behavior. Chem Pap. 2018;72:1917–25.CrossRef

46.

Pisoschi AM, Pop A, Cimpeanu C, Predoi G. Antioxidant capacity determination in plants and plant-derived products: A review. Oxid Med Cell Longev. 2016;2016:9130976. https://doi.org/10.1155/2016/9130976.CrossRefPubMedPubMedCentral

47.

Guleria S, Tiku AK, Singh G, Koul A, Gupta S, Rana S. In vitro antioxidant activity and phenolic contents in methanol extracts from medicinal plants. J Plant Biochem Biotechnol. 2013;22:9–15.CrossRef

48.

Al-Laith AA, Alkhuzai J, Freije A. Assessment of antioxidant activities of three wild medicinal plants from Bahrain. Arab J Chem. 2019;12:2365–71.CrossRef

49.

Apak R, Güçlü K, Demirata B, Özyürek M, Çelik SE, Bektaşoğlu B, et al. Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC Assay. Mol. 2007;12:1496–547.CrossRef

50.

Lalhminghlui K, Jagetia GC. Evaluation of the free-radical scavenging and antioxidant activities of Chilauni, Schima wallichii Korth in vitro. Future Sci OA. 2018;4:FSO272. https://doi.org/10.4155/fsoa-2017-0086.CrossRefPubMedPubMedCentral

51.

Khan RA, Khan MR, Sahreen S, Ahmed M. Assessment of flavonoids contents and in vitro antioxidant activity of Launaea procumbens. Chem Cent J. 2012;6:43. https://doi.org/10.1186/1752-153X-6-43.CrossRefPubMedPubMedCentral

52.

Sarian MN, Ahmed QU, Mat So’ad SZ, Alhassan AM, Murugesu S, Perumal V, et al. Antioxidant and antidiabetic effects of flavonoids: A structure-activity relationship based study. Biomed Res Int. 2017;2017:8386065. https://doi.org/10.1155/2017/8386065.CrossRefPubMedPubMedCentral

53.

Topal F, Nar M, Gocer H, Kalin P, Kocyigit UM, Gülçin İ, et al. Antioxidant activity of taxifolin: an activity–structure relationship. J Enzyme Inhib Med Chem. 2016;31:674–83.CrossRef

54.

Li X, Xie H, Jiang Q, Wei G, Lin L, Li C, et al. The mechanism of (+) taxifolin’s protective antioxidant effect for •OH-treated bone marrow-derived mesenchymal stem cells. Cell Mol Biol Lett. 2017;22:31. https://doi.org/10.1186/s11658-017-0066-9.CrossRefPubMedPubMedCentral

55.

Pengfei L, Tiansheng D, Xianglin H, Jianguo W. Antioxidant properties of isolated isorhamnetin from the sea buckthorn marc. Plant Foods Hum Nutr. 2009;64:141–5.CrossRef

56.

Duthie G, Morrice P. Antioxidant capacity of flavonoids in hepatic microsomes is not reflected by antioxidant effects In Vivo. Oxid Med Cell Longev. 2012;2012:165127. https://doi.org/10.1155/2012/165127.CrossRefPubMedPubMedCentral

57.

Bonesi M, Loizzo MR, Menichini F, Tundis R. Flavonoids in treating psoriasis. In: Chatterjee S, Jungraithmayr W, Bagchi D, editors. Immunity and inflammation in health and disease. Academic Press; 2018. p. 281–94.CrossRef

58.

Ngamsuk S, Huang T-C, Hsu J-L. Determination of phenolic compounds, procyanidins, and antioxidant activity in processed Coffea arabica L. leaves. Foods. 2019;8:389. https://doi.org/10.3390/foods8090389.CrossRefPubMedCentral

59.

Saeed N, Khan MR, Shabbir M. Antioxidant activity, total phenolic and total flavonoid contents of whole plant extracts Torilis leptophylla L. BMC Complement Altern Med. 2012;12:221. https://doi.org/10.1186/1472-6882-12-221.CrossRefPubMedPubMedCentral

Title: Flavonoid profile and antioxidant properties of Algerian common yew (Taxus baccata L.)
Authors: Mohamed Bekhouche
Roukia Benyammi
Majda Khelifi Slaoui
Soumia Krimat
Cedric Paris
Lakhdar Khelifi
Abdelkader Morsli
Publication date: 01-12-2022
Publisher: Springer Berlin Heidelberg
Published in: Clinical Phytoscience / Issue 1/2022
Electronic ISSN: 2199-1197
DOI: https://doi.org/10.1186/s40816-022-00348-x

At a glance: The STEP trials

Springer Medicine

Flavonoid profile and antioxidant properties of Algerian common yew (Taxus baccata L.)

Abstract

Background

Methods

Results

Conclusion

At a glance: The STEP trials

Springer Medicine

Abstract

Background

Methods

Results

Conclusion

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