Abstract
Detailed chemical composition was determined in 7 tea samples, i.e., infusions prepared from the dried aerial herba of St. John’s wort (Hypericum perforatum L.) commercially available or collected, from locations in the east and south-east Serbia. In addition, quantitative analysis for five selected major constituents in the samples, neochlorogenic acid, isoquercitrin, quercetin, hyperforin and hypericin, was performed. Qualitative and quantitative analyses were done by Ultra-high-performance liquid chromatography–diode array detector–electrospray mass spectrometry (UHPLC–DAD–ESI–MS/MS) method. The aims of this work were to detect and identify as well as quantitative analysis of phytochemicals in the infusions prepared in a traditional way and to compare obtained results with the corresponding available literature. Over fifty compounds from wide range of polyphenols were detected in the infusions: acids and phenolic acids, flavonoids, phloroglucinols, naphthodianthrones and xanthones. Some of them such as 4- and 5-O-p-coumaroyl-quinic and 4-O-feruloyl-quinic acids, or some quercetin and dihydroquercetin derivatives were for first time detected in the St. John’s wort infusions. Among them, high concentrations of major quantified phenolics determined in infusions (nechlorogenic acid, isoquercitrin, quercetin, hyperforin and hypericin) can contribute to a higher quality of St. John’s wort teas from Serbia origin. Their concentrations vary through the samples: concentration of neochlorogenic acid is in the range of 51.8–103.7 mg/dm3, isoquercitrin 17.4–35.3 mg/dm3, quercetin 22.0–54.1 mg/dm3, hyperforin 0.13–0.92 mg/dm3 and hypericin 0.5–4.9 mg/dm3.
Graphic abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Acosta J, Sevilla I, Salomón S, Nuevas L, Romero A, Amaro D (2016) Determination of mangiferin solubility in solvents used in the biopharmaceutical industry. J Pharm Pharmacogn Res 4(2):49–53
Agapouda A, Booker A, Kiss T, Hohmann J, Heinrich M, Csupor D (2019) Quality control of Hypericum perforatum L. analytical challenges and recent progress. J Pharm Pharmacol 71:15–37
Alali FQ, Tawaha K (2009) Dereplication of bioactive constituents of the genus hypericum using LC-(+,-)-ESI-MS and LC-PDA techniques: Hypericum triquterifolium as a case study. Saudi Pharm J 17:269–274. https://doi.org/10.1016/j.jsps.2009.10.002
Aleixandre-Tudo JL, du Toit W (2018) The role of UV-Visible spectroscopy for phenolic compounds quantification in winemaking In Solís-Oviedo RL, de la Cruz Pech-Canul A (eds) Frontiers and new trends in the science of fermented food and beverages. IntechOpen London, UK. https://doi.org/10.5772/intechopen.79550
Ang CYW, Cui Y, Chang HC, Luo W, Heinze TM (2002) Determination of St John’s wort components in dietary supplements and functional foods by liquid chromatography. J AOAC Int 85(6):1360–1369. https://doi.org/10.1093/jaoac/85.6.1360
Arsić I (2016) Preparation and characterization of St. John’s wort herb extracts using olive, sunflower and palm oils. Acta Fac Med Naiss 33(2):119–126
Avato P, Guglielmi G (2004) Determination of major constituents in St. John’s Wort under different extraction conditions. Pharm Biol 42(1):83–89. https://doi.org/10.1080/13880200490505663
Bagdonaitė E, Martonfi P, Repčák M, Labokas J (2012) Variation in concentrations of major bioactive compounds in Hypericum perforatum L. from Lithuania. Ind Crops Prod 35:302–308. https://doi.org/10.1016/j.indcrop.2011.07.018
Barnes J, Anderson LA, Phillipson JD (2001) St John’s wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties. J Pharm Pharmacol 53:583–600. https://doi.org/10.1211/0022357011775910
Barros L, Dueñas M, Carvalho AM, Ferreira ICFR, Santos-Buelga C (2012) Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern Portugal. Food Chem Toxicol 50(5):1576–1582. https://doi.org/10.1016/j.fct.2012.02.004
Bento-Silva A, Koistinen VM, Mena P, Bronze MR, Hanhineva K, Sahlstrøm S, Kitrytė V, Moco S, Aura A-M (2020) Factors affecting intake, metabolism and health benefits of phenolic acids: do we understand individual variability? Eur J Nutr 59:1275–1293. https://doi.org/10.1007/s00394-019-01987-6
Butterweck V, Jüngerliemk G, Nahrstedt A, Winterhoff H (2000) Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med 66:3–6. https://doi.org/10.1055/s-2000-11119
Chandrasekera DH, Welham KJ, Ashton D, Middleton R, Heinrich M (2005) Quantitative analysis of the major constituents of St John’s wort with HPLC-ESI-MS. J Pharm Pharmacol 57:1645–1652. https://doi.org/10.1211/jpp.57.12.0015
Chen S-D, Lu C-J, Zhao R-Z (2014) Qualitative and quantitative analysis of rhizoma smilacis glabrae by ultra high performance liquid chromatography coupled with LTQ orbitrapXL hybrid mass spectrometry. Molecules 19:10427–10439. https://doi.org/10.3390/molecules190710427
Çirak C, Radusienë J, Karabük BS, Janulis V, Ivanauskas L (2007) Variation of bioactive compounds in Hypericum perforatum growing in Turkey during its phenological cycle. J Integr Plant Biol 49(5):615–620. https://doi.org/10.1111/j.1744-7909.2007.00479.x
Clifford MN (2000) Chlorogenic acids and other cinnamates—nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agric 80:1033–1043. https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7%3c1033::AID-JSFA595%3e3.0.CO;2-T
Clifford MN, Johnston KL, Knight S, Kuhnert N (2003) Hierarchical scheme for LC-MSn identification of chlorogenic acids. J Agric Food Chem 51:2900–2911. https://doi.org/10.1021/jf026187q
Clifford MN, Zheng W, Kuhnert N (2006) Profiling the chlorogenic acids of aster by HPLC–MSn. Phytochem Anal 17:384–393. https://doi.org/10.1002/pca.935
Cooper KA, Campos-Gimeä Nez E, Nez Alvarez DJ, Nagy KL, Donovan JL, Williamson G (2007) Rapid reversed phase ultra-performance liquid chromatography analysis of the major cocoa polyphenols and inter-relationships of their concentrations in chocolate. J Agric Food Chem 55:2841–2847. https://doi.org/10.1021/jf063277c
The European Pharmacopoeia, 8th edition (2014) (Ph. Eur. 8.0) Strasbourg: Council of Europe
Cuadrado-Silva CT, Pozo-Bayón MA, Osorio C (2017) Targeted metabolomic analysis of polyphenols with antioxidant activity in sour guava (Psidium friedrichsthalianum Nied.) Fruit. Molec 22(11):1–11. https://doi.org/10.3390/molecules22010011
de Rijke E, Out P, Niessen WMA, Ariese F, Gooijer C, Brinkman UATh (2006) Analytical separation and detection methods for flavonoids. J Chromatogr A 1112(2006):31–63. https://doi.org/10.1016/j.chroma.2006.01.019
Dias ACP, Seabra RM, Andrade PB, Fernandes-Ferreira M (1999) The development and evaluation of an HPLC-DAD method for the analysis of phenolic fractions from in vivo and in vitro biomass of Hypericum species. J Liq Chrom Rel Technol 22(2):215–227. https://doi.org/10.1081/JLC-100101655
Erdelmeier CAJ, Koch E, Hoerr R (2000) Hypericum perforatum-St. John’s wort chemical, pharmacological and clinical aspects. Stud Nat Prod Chem 22:643–716. https://doi.org/10.1016/S1572-5995(00)80037-X
Filippini R, Piovan A, Borsarini A, Caniato R (2010) Study of dynamic accumulation of secondary metabolites in three subspecies of Hypericum perforatum. Fitoterapia 81:115–119. https://doi.org/10.1016/j.fitote.2009.08.002
Flamini R (2013) Recent applications of mass spectrometry in the study of grape and wine polyphenols. ISRN Spectrosc. https://doi.org/10.1155/2013/813563
Germ M, Stibilj V, Kreft S, Gaberščik A, Kreft I (2010) Flavonoid, tannin and hypericin concentrations in the leaves of St John’s wort (Hypericum perforatum L.) are affected by UV-B radiation levels. Food Chem 122:471–474. https://doi.org/10.1016/j.foodchem.2010.03.008
Gowda N, Kumar P, Panghal S, Rajshree M (2010) ICH guidance in practice: validated reversed-phase HPLC method for the determination of active mangiferin from extracts of Mangifera indica Linn. J Chromatogr Sci 48:156–160. https://doi.org/10.1093/chromsci/48.2.156
Greeson JM, Sanford B, Monti DA (2001) St. John’s wort (Hypericum perforatum): a review of the current pharmacological, toxicological, and clinical literature. Psychopharmacol 153:402–414. https://doi.org/10.1007/s002130000625
Hasib A, Jaouad A, Mahrouz M, Khouili M (2002) HPLC determination of organic acids in Moroccan apricot. Cienc Tecnol Aliment 3(4):207–211. https://doi.org/10.1080/11358120209487729
Hecka A, Maunit B, Aubriet F, Muller J-F (2009) Study of active naphtodianthrone St John’s Wort compounds by electrospray ionization Fourier transform ion cyclotron resonance and multi-stage mass spectrometry in sustained off-resonance irradiation collision-induced dissociation and infrared multiphoton dissociation modes. Rapid Commun Mass Spectrom 23:885–898. https://doi.org/10.1002/rcm.3952
Hernández-Saavedra D, Pérez-Ramírez IF, Ramos-Gómez M, Mendoza-Díaz S, Loarca-Piña G, Reynoso-Camacho R (2016) Phytochemical characterization and effect of Calendula officinalis, Hypericum perforatum, and Salvia officinalis infusions on obesityassociated cardiovascular risk. Med Chem Res 25:163–172. https://doi.org/10.1007/s00044-015-1454-1
Jürgenliemk G, Nahrstedt A (2002) Phenolic compounds from Hypericum perforatum. Planta Med 68:89–91. https://doi.org/10.1055/s-2002-20053
Jürgenliemk G, Nahrstedt A (2003) Dissolution, solubility and cooperativity of phenolic compounds from Hypericum perforatum L. in aqueous systems. Pharmazie 58(3):200–203
Kachlicki P, Piasecka A, Stobiecki M, Marczak Ł (2016) Structural characterization of flavonoid glycoconjugates and their derivatives with mass spectrometric techniques. Molecules 21:1494. https://doi.org/10.3390/molecules21111494
Kang J, Price WE, Ashton J, Tapsell LC, Johnson S (2016) Identification and characterization of phenolic compounds in hydromethanolic extracts of sorghum wholegrains by LC-ESI-MSn. Food Chem 211:215–226. https://doi.org/10.1016/j.foodchem.2016.05.052
Konan KM, Mamyrbekova-Bekro JA, Bakalara N, Virteux D, Pirat J-L, Bekro Y-A (2014) HPLC analysis and cytotoxicity of n-butanol extract from Glyphaea brevis roots against C6 glioma cells. Sci Pharm 82:171–176. https://doi.org/10.3797/scipharm.1307-08
Kuhnert N, Jaiswal R, Matei MF, Sovdat T, Deshpande S (2010) How to distinguish between feruloyl quinic acids and isoferuloyl quinic acids by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 24:1575–1582. https://doi.org/10.1002/rcm.4537
Kwiecień I, Szydłowska A, Kawka B, Beerhues L, Ekiert H (2015) Accumulation of biologically active phenolic acids in agitated shoot cultures of three Hypericum perforatum cultivars: ‘Elixir’, ‘Helos’ and ‘Topas.’ Plant Cell Tiss Organ Cult 123:273–281. https://doi.org/10.1007/s11240-015-0830-3
Ma F, Gong X, Zhou X, Zhao Y, Li M (2015) An UHPLC–MS/MS method for simultaneous quantification of gallic acid and protocatechuic acid in rat plasma after oral administration of Polygonum capitatum extract and its application to pharmacokinetics. J Ethnopharmacol 162:377–383. https://doi.org/10.1016/j.jep.2014.12.044
Maleš Ž, Brantner AH, Sović K, Pilepić KH, Plazibat M (2006) Comparative phytochemical and antimicrobial investigations of Hypericum perforatum L. subsp. perforatum and H. perforatum subsp. angustifolium (DC.) Gaudin. Acta Pharm 56:359–367 https://pubmed.ncbi.nlm.nih.gov/19831284/
Masike K, Mhlongo MI, Mudau SP, Nobela O, Ncube EN, Tugizimana F, George MJ, Madala NE (2017) Highlighting mass spectrometric fragmentation differences and similarities between hydroxycinnamoyl-quinic acids and hydroxycinnamoyl-isocitric acids. Chem Cent J 11:29. https://doi.org/10.1186/s13065-017-0262-8
Michler H, Laakmann G, Wagner H (2011) Simultaneous quantitation of amentoflavone and biapigenin, the minor and major biflavones from Hypericum perforatum L., in human plasma and its application to real blood. Phytochem Anal 22:42–50. https://doi.org/10.1002/pca.1249
Miraldi E, Biagi M, Giachetti D (2006) Chemical constituents and effect of topical application of Oleum Hyperici on skin sensitivity to simulated sun exposure. Nat Prod Commun 1(3):209–213. https://doi.org/10.1177/1934578X0600100307
Nahrstedt A, Butterweck V (1997) Biologically active and other chemical constituents of the herb of Hypericum perforaturn L. Pharmacopsychiat 30:129–134. https://doi.org/10.1055/s-2007-979533
Naït-Si Y, Fourneron J-D (2004) Hypericin and pseudohypericin. Purity criteria and quantitative determination in extracts of Saint John’s wort (Hypericum perforatum). Monatsh Chem 135:1319–1326. https://doi.org/10.1007/s00706-004-0207-5
Ng L-K, Lafontaine P, Vanier M (2004) Characterization of migarette tobacco by direct electrospray ionization-ion trap mass spectrometry (ESI-ITMS) analysis of the aqueous extracts - a novel and simple approach. J Agric Food Chem 52:7251–7257. https://doi.org/10.1021/jf040203x
Oliveira AI, Pinho C, Bruno Sarmento B, Dias ACP (2016) Neuroprotective activity of Hypericum perforatum and its major components. Fron Plant Sci Volume 7, Article 1004, 15 pages https://doi.org/10.3389/fpls.2016.01004
Orčić DZ, Mimica-Dukić NM, Franciskovic MM, Petrović SS, Jovin ED (2011) Antioxidant activity relationship of phenolic compounds in Hypericum perforatum L. Chem Cent J 5(34):1–8. https://doi.org/10.1186/1752-153X-5-34
Orhan IE, Kartal M (2015) LC-DAD-MS-Assisted quantification of marker compounds in Hypericum perforatum L. (St. John’s wort) and its antioxidant activity. Turk J Pharm Sci 12(3):279–286
Öztürk N, Tunçel M, Potoğlu-Erkara I (2009) Phenolic compounds and antioxidant activities of some Hypericum species: a comparative study with H. perforatum. Pharm Biol 47(2):120–127. https://doi.org/10.1080/13880200802437073
Piovan FR, Caniato R, Borsarini A, Maleci LB, Cappelletti EM (2004) Detection of hypericins in the ‘“red glands”’ of Hypericum elodes by ESI–MS/MS. Phytochemistry 65:411–414. https://doi.org/10.1016/j.phytochem.2003.11.003
Piperopoulos G, Lotz R, Wixforth A, Schimierer T, Zeller K (1997) Determination of naphtodianthrones in plant extracts from Hypericum perforatum L. by liquid chromatography–electrospray mass spectrometry. J Chromatogr B 695:309–319. https://doi.org/10.1016/s0378-4347(97)00188-6
Ploss O, Petereit F, Nahrstedt A (2001) Procyanidins from the herb of Hypericum perforatum. Pharmazie 56(6):509–11 https://pubmed.ncbi.nlm.nih.gov/11446175/
Porzel A, Farag MA, Mülbradt J, Wessjohann LA (2014) Metabolite profiling and fingerprinting of Hypericum species: a comparison of MS and NMR metabolomics. Metabolomics 10:574–588. https://doi.org/10.1007/s11306-013-0609-7
Rusalepp L, Raal A, Püssa T, Mäeorg U (2017) Comparison of chemical composition of Hypericum perforatum and H. maculatum in Estonia. Biochem Syst Ecol 73:41–46. https://doi.org/10.1016/j.bse.2017.06.004
Sato Y, Itagaki S, Kurokawa T, Ogura J, Kobayashi M, Hirano T, Sugawara M, Iseki K (2011) In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. Int J Pharm 403:136–138. https://doi.org/10.1016/j.ijpharm.2010.09.035
Schulze EA (2013) HPLC method development for characterisation of the phenolic composition of cyclopia subternata and C. maculata extracts and chromatographic fingerprint analysis for quality control. Master of Science in Food Science. Stellenbosch University http://scholar.sun.ac.za
Silva BA, Ferreres F, Malva JO, Dias ACP (2005) Phytochemical and antioxidant characterization of Hypericum perforatum alcoholic extracts. Food Chem 90:157–167. https://doi.org/10.1016/j.foodchem.2004.03.049
Silva BA, Malva JO, Dias ACP (2008) St. John’s Wort (Hypericum perforatum) extracts and isolated phenolic compounds are effective antioxidants in several in vitro models of oxidative stress. Food Chem 110:611–619. https://doi.org/10.1016/j.foodchem.2008.02.047
Sleno L, Daneshfar R, Eckert GP, Müller WE, Volmer DA (2006) Mass spectral characterization of phloroglucinol derivatives hyperforin and adhyperforin. Rapid Commun Mass Spectrom 20:2641–2648. https://doi.org/10.1002/rcm.2650
Smelcerovic A, Spiteller M (2006) Phytochemical analysis of nine Hypericum L. species from Serbia and the F.Y.R. Macedonia. Pharmazie 61:251–252 https://pubmed.ncbi.nlm.nih.gov/16599273
Stöggl WM, Huck CW, Bonn GK (2004) Structural elucidation of catechin and epicatechin in sorrel leaf extracts using liquid-chromatography coupled to diode array-, fluorescence-, and mass spectrometric detection. J Sep Sci 27:524–528. https://doi.org/10.1002/jssc.200301694
Strzemski M, Dresler S, Sowa I, Kurach Ł, Kováčik J, Wojas-Krawczyk K, Wójciak M (2020) Direct spectroscopic and GC profiling combined with chemometric analysis as an alternative approach to investigate Hypericum species: Is it possible to replace HPLC? Ind Crop Prod 157:112930. https://doi.org/10.1016/j.indcrop.2020.112930
Tatsis EC, Boeren S, Exarchou V, Troganis AN, Vervoort J, Gerothanassis JP (2007) Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochem 68:383–393. https://doi.org/10.1016/j.phytochem.2006.11.026
Tocci N, Gaid M, Kaftan F, Belkheir AK, Belhadj I, Liu B, Svatoš A, Hänsch R, Pasqua G, Beerhues L (2018) Exodermis and endodermis are the sites of xanthone biosynthesis in Hypericum perforatum roots. New Phytol 217(3):1099–1112. https://doi.org/10.1111/nph.14929
Tolonen A, Uusitalo J, Hohtola A, Jalonen J (2002) Determination of naphtodianthrones and phloroglucionols from Hypericum perforatum extracts by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 16:396–402. https://doi.org/10.1002/rcm.591
Tusevski O, Petreska Stanoeva J, Stefova M, Gadzovska Simic S (2013) Phenolic profile of dark-grown and photoperiod-exposed Hypericum perforatum L. hairy root cultures. Sci World J. https://doi.org/10.1155/2013/602752
Tusevski O, Petreska Stanoeva J, Stefova M, Gadzovska Simic S (2014) Identification and quantification of phenolic compounds in Hypericum perforatum L. transgenic shoots. Acta Physiol Plant 36:2555–2569. https://doi.org/10.1007/s11738-014-1627-4
Tusevski O, Krstikj M, Petreska Stanoeva J, Stefova M, Gadzovska Simic S (2019) Phenolic compounds composition of Hypericum perforatum L. wild-growing plants from the Republic of Macedonia. Agric Conspec Sci 84(1):67–75
Verdu C, Gatto J, Freuze I, Richomme P, Laurens F, Guilet D (2013) Comparison of two methods, UHPLC-UV and UHPLC-MS/MS, for the quantification of polyphenols in cider apple juices. Molec 18(9):10213–10227. https://doi.org/10.3390/molecules180910213
Wang X, Yang B, Zhang A, Sun H, Dong W (2017) Rapid analysis of multiple constituents of suanzaoren decoction by UPLC-MS. In: Wang X (ed) Serum pharmacochemistry of traditional chinese medicine-technologies, strategies and applications. Academic Press is an imprint of Elsevier, London, pp 201–208
WHO 2002: Herba Hyperici In WHO monographs on selected medicinal p1ants. Vol 2. pp 149–171, World Health Organization, Geneva, Switzerland.
Wollgast J, Anklam E (2000) Review on polyphenols in Theobroma cacao: changes in composition during the manufacture of chocolate and methodology for identification and quantification. Food Res Int 33:423–447. https://doi.org/10.1016/S0963-9969(00)00068-5
Xiao Z-P, Peng Z-Y, Peng MJ, Yan WB, Ouyang YZ, Zhu HL (2011) Flavonoids health benefits and their molecular mechanism. Mini Rev Med Chem 11(2):169–177. https://doi.org/10.2174/138955711794519546
Xu J-G, Hu Q-P, Liu Y (2012) Antioxidant and DNA-Protective Activities of Chlorogenic Acid Isomers. J Agric Food Chem 60:11625–11630. https://doi.org/10.1021/jf303771s
Yao H, Chen B, Zhang Y, Ou H, Li Y, Li S, Shi P, Lin X (2017) Analysis of the total biflavonoids extract from Selaginella doederleinii by HPLC-QTOF-MS and its in vitro and in vivo anticancer effects. Molec 22:325(1–17) https://doi.org/10.3390/molecules22020325
Zdunic G, Godjevac D, Savikin K, Petrovic S (2017) Comparative analysis of phenolic compounds in seven Hypericum species and their antioxidant properties. Nat Prod Commun 12(11):1805–1811. https://doi.org/10.1177/1934578X1701201140
Zeliou K, Kontaxis NI, Margianni E, Petrou C, Lamari FN (2017) Optimized and validated HPLC analysis of St. John’s wort extract and final products by simultaneous determination of major ingredients. J Chromatogr Sci 55(8):805–812 https://doi.org/10.1093/chromsci/bmx040
Zhang Y, Xiong H, Xu X, Xue X, Liu M, Xu S, Liu H, Gao Y, Zhang H, Li X (2018) Compounds identification in semen cuscutae by ultra-high-performance liquid chromatography (UPLCs) coupled to electrospray ionization mass spectrometry. Molec 23:1199(1–16) https://doi.org/10.3390/molecules23051199
Zvezdanović J, Petrović S, Savić S, Cvetković D, Lj S, Stanojević J, Lazarević A (2021) Phenolics and mineral content in St. John’s wort infusions from Serbia origin: An HPLC and ICP-OES study. Chem Pap 75:2807–2817. https://doi.org/10.1007/s11696-021-01521-1
Acknowledgements
Republic of Serbia—Ministry of Education, Science and Technological Development, Program for financing scientific research work, number 451-03-9/2021-14/200133.
Funding
Not applicable.
Author information
Authors and Affiliations
Contributions
All authors contributed.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflicts of interest.
Ethics approval
Not applicable.
Consent to participate
All the authors are consent to participate.
Consent for publication
All the authors are consent to publication.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Zvezdanović, J. UHPLC–DAD–ESI–MS/MS characterization of St. John’s wort infusions from Serbia origin. Chem. Pap. 76, 1329–1347 (2022). https://doi.org/10.1007/s11696-021-01940-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-021-01940-0