Chemical profiling of Oxalis species growing wild in Egypt using HRLC/MS Spectrometry
Year 2022,
Volume: 9 Issue: 4, 426 - 439, 21.12.2022
Amal Draz
,
Salwa Kawashty
Eman Shamso
Hasnaa Hosni
Sameh Hussein
Abstract
Three medicinally promising Oxalis species, namely O. pes-caprae, O. corymbosa & O. latifolia were collected from Egyptian flora and their methanolic extracts were subjected to LC-QTOF-MS analysis to annotate their chemical profiles. Subsequently, 50 compounds belonging to various chemical classes were identified and characterized, of which 34 compounds were first reported from Oxalis L.. Moreover, five flavone compounds were separated and identified from O. pes-caprae; their structures were elucidated using acid hydrolysis, UV/vis, 1H-NMR, and HR-ESI-MS. The chemotaxonomic relationship of the studied species was evaluated and the extracted data were statistically analyzed and classified Oxalis sp. into two distinct clusters. Each cluster was characterized by special chemical features that helped in distinguishing between them.
Thanks
The authors acknowledge the National Research Centre where this study was performed.
References
- Almahy, H.A., & Fouda, H.A.R. (2013) Isolation of luteolin 8-C-β-D-glucopyranoside from the roots of Salvadora persica (Rutaceae). Journal of Current Chemical and Pharmaceutical Sciences, 3(1), 49-53.
- Ben Salah, H., Smaoui, S., Abdennabi, R., & Allouche, N. (2019). LC-ESI-MS/MS phenolic profile of Volutaria lippii (L.) Cass. extracts and evaluation of their in vitro antioxidant, Antiacetylcholinesterase, antidiabetic, and antibacterial activities. Evidence-Based Complementary and Alternative Medicine, 2019. https://doi.org/10.1155/2019/9814537
- Brent, L.C., Reiner, J.L., Dickerson, R.R., & Sander, L.C. (2014). Method for characterization of low molecular weight organic acids in atmospheric aerosols using ion chromatography mass spectrometry. Journal of Analytical Chemistry, 86(15), 7328 7336. https://doi.org/10.1021/ac403937e
- Brito, A., Ramirez, J.E., Areche, C., Sepúlveda, B., & Simirgiotis, M.J. (2014). HPLC-UV-MS profiles of phenolic compounds and antioxidant activity of fruits from three citrus species consumed in Northern Chile. Molecules, 19(11), 17400 17421. https://doi.org/10.3390/molecules191117400
- Cao-Ngoc, P., Leclercq, L., Rossi, J.C., Hertzog, J., Tixier, A.S., Chemat, F., Nasreddine, R., Al HamouiDitBanni, G., Nehmé, R., Schmitt-Kopplin, P., & Cottet, H. (2020). Water-based extraction of bioactive principles from black currant leaves and chrysanthellum americanum: A comparative study. Foods, 9(10), 1478. https://doi.org/10.3390/foods9101478
- Cocuron, J.C., & Alonso, A.P. (2014). Liquid chromatography tandem mass spectrometry for measuring ¹³C-labeling in intermediates of the glycolysis and pentose phosphate pathway. Plant Metabolic Flux Analysis, Springer. https://doi.org/10.1007/978-1-62703-688-7_9. PMID: 24222414.
- Dellagreca, M., Previtera, L., Purcaro, R., & Zarrelli, A. (2009). Phytotoxic Aromatic Constituents of Oxalis pes-caprae. Chemistry & Biodiversity, 6(1), 459-465. https://doi.org/10.1002/cbdv.200800179
- Draz, A.A., Shamso, E.M., Hosni, H.A., Kawashty, S.A., & Hussein, S.R. (2021). Comparative study of Oxalis L. species growing wild in Egypt: GC-MS analysis and chemosystematic significance. Egyptian Journal of Chemistry, 64(9), 5251 5256. https://doi.org/10.21608/EJCHEM.2021.72328.3592
- Eissa, M.A., Hashim, Y.Z., El-Kersh, D.M., Abd-Azziz, S.S., Salleh, H.M., Isa, M.L.M., & Abd Warif, N.M. (2020). Metabolite Profiling of Aquilaria malaccensis leaf extract using Liquid Chromatography-Q-TOF-Mass spectrometry and investigation of its potential antilipoxygenase activity in-vitro. Processes, 8(2), 202. https://doi.org/10.3390/pr8020202
- El-Khanagry, S.S.G. (2005). New records of dicotyledonous taxa to the flora of Egypt. Bulletin of Faculty of Agriculture, Cairo University, 56(1), 89-105.
- Gamir, J., Pastor, V., Cerezo, M., & Flors, V. (2012). Identification of indole-3- carboxylic acid as mediator of priming against cucumerina. Plant Physiology and Biochemistry, 61, 169-179. https://doi.org/10.1016/j.plaphy.2012.10.004
- Gaspar, M.C., Fonseca, D.A., Antunes, M.J., Frigerio, C., Gomes, N.G., Vieira, M., Santos, A.E., Cruz, M.T., Cotrim, M.D., & Campos, M.G. (2018). Polyphenolic characterisation and bioactivity of an Oxalis pes-caprae L. leaf extract. Natural Product Research, 32, 732-738. https://doi.org/10.1080/14786419.2017.1335728
- Gervasoni, J., Schiattarella, A., Giorgio, V., Primiano, A., Russo, C., Tesori, V., Scaldaferri, F., Urbani, A., Zuppi, C., & Persichilli, S. (2016). Validation of an LC-MS/MS method for urinary lactulose and mannitol quantification: Results in patients with irritable bowel syndrome. Disease Markers, 2016, ID 5340386, 6. https://doi.org/10.1155/2016/5340386
- Güçlütürk, I., Detsi, A., Weiss, E.K., Ioannou, E., Roussis, V., & Kefalas, P. (2012). Evaluation of anti‐oxidant activity and identification of major polyphenolics of the invasive weed Oxalispes caprae. Phytochemical Analysis, 23(6), 642 646. https://doi.org/10.1002/pca.2367
- Guerrero, R.F., Valls-Fonayet, J., Richard, T., & Cantos-Villar, E. (2020). A rapid quantification of stilbene content in wine by ultra-high pressure liquid chromatography–Mass spectrometry. Food Control, 108, 106821. https://doi.org/10.1016/j.foodcont.2019.106821
- Hassan, W.H., Abdelaziz, S., & Al Yousef, H.M. (2019). Chemical composition and biological activities of the aqueous fraction of Parkinsonea aculeata L. growing in Saudi Arabia. Arabian Journal of Chemistry, 12(3), 377-387. https://doi.org/10.1016/j.arabjc.2018.08.003
- Hussein, S.R., Latif, R.R.A., Marzouk, M.M., Elkhateeb, A., Mohammed, R.S., Soliman, A.A., & Abdel-Hameed, E.S.S. (2018). Spectrometric analysis, phenolics isolation and cytotoxic activity of Stipagrostis plumosa (Family Poaceae). Chemical Papers-Chemicke Zvesti, 72(1), 29-37. https://doi.org/10.1007/s11696-017-0254-0
- Jin, J., Lao, J., Zhou, R., He, W., Qin, Y., Zhong, C., Xie, J., Liu, H., Wan, D., Zhang, S., & Qin, Y. (2018). Simultaneous identification and dynamic analysis of saccharides during steam processing of rhizomes of Polygonatum cyrtonema by HPLC–QTOF–MS/MS. Molecules, 23(11), 2855. https://doi.org/10.3390/molecules23112855
- Kang, J., Price, W.E., Ashton, J., Tapsell, L.C., & Johnson, S. (2016). Identification and characterization of phenolic compounds in hydromethanolic extracts of sorghum whole grains by LC ESI MSn. Food Chemistry, 211, 215 226. https://doi.org/10.1016/j.foodchem.2016.05.052
- Krasteva, I., & Nikolov, S. (2008). Flavonoids in Astragalus corniculatus. Quím Nova, 31, 59-60. https://doi.org/10.1590/S0100-40422008000100012
- Kumarasamy, Y., Byres, M., Cox, P.J., Delazar, A., Jaspars, M., Nahar, L., Shoeb, M., & Sarker, S.D. (2004). Isolation, structure elucidation, and biological activity of flavone 6-C-glycosides from Alliaria petiolata. Chemistry of Natural Compounds, 40(2), 122-128.
- Lin, Y.T., Mao, Y.W., Imtiyaz, Z., Chiou, W.F., & Lee, M.H. (2020). Comprehensive LC-MS/MS-based phytochemical perspectives and osteogenic effects of Uraria crinita. Food Function, 11(6), 5420-5431. https://doi.org/10.1039/D0FO00782J
- Llorach, R., Urpi-Sarda, M., Jauregui, O., Monagas, M., & Andres-Lacueva, C. (2009). An LC-MS-based metabolomics approach for exploring urinary metabolome modifications after cocoa consumption. Journal of Proteome Research, 8(11), 5060 5068. https://doi.org/10.1021/pr900470a
- Lourteig, A. (2000). Oxalis L., subgenera Monoxalis (Small) Lourt., Oxalis y Trifidus Lourt. Bradea, 7(2), 201–629.
- Lucas, A.R. (2021). Viruses as therapeutics: Methods and protocols. Springer.
- Marzouk, M.M., Hussein, S.R., Elkhateeb, A., El-shabrawy, M., Abdel-Hameed, E.S.S., & Kawashty, S.A. (2018). Comparative study of Mentha species growing wild in Egypt: LC-ESI-MS analysis and chemosystematic significance. Journal of Applied Pharmaceutical Science, 8, 116-122. https://doi.org/10.7324/JAPS.2018.8816
- MassBank Europe, Mass Spectral DataBase. Available online: https://massbank.eu/MassBank/ (accessed on 19thJanuary, 2022).
- Minitab 21, Statistical & Data Analysis Software. Available online: https://www.minitab.com/en-us/support/downloads/ (accessed on 17thFebruary, 2022).
- Oberlander, K.C., Dreyer, L.L., & Elser, K.J. (2002). Biogeographv of Oxalis (Oxalidaceae) in South Africa: A preliminary study. Bothalia. African Biodiversity & Conservation, 32(1), 97-100. https://doi.org/10.4102/abc.v32i1.472
- Prasad Pandey, B., Prakash Pradhan, S., & Adhikari, K. (2020). LC‐ESI‐QTOF‐MS for the profiling of the metabolites and in vitro enzymes inhibition activity of Bryophyllum pinnatum and Oxalis corniculata collected from Ramechhap District of Nepal. Chemistry & Biodiversity, 17, e2000155. https://doi.org/10.1002/cbdv.202000155
- Ricciutelli, M., Moretti, S., Galarini, R., Sagratini, G., Mari, M., Lucarini, S., Vittori, S., & Caprioli, G. (2019). Identification and quantification of new isomers of isopropyl-malic acid in wine by LC IT and LC Q Orbitrap. Food Chemistry, 294, 390 396. https://doi.org/10.1016/j.foodchem.2019.05.068
- Ruan, J., Yan, J., Zheng, D., Sun, F., Wang, J., Han, L., Zhang, Y., & Wang, T. (2019). Comprehensive chemical profiling in the ethanol extract of Plucheaindica aerial parts by liquid chromatography/mass spectrometry analysis of its silica gel column chromatography fractions. Molecules, 24(15), 2784. https://doi.org/10.3390/molecules24152784
- Sarfraz, I., Rasul, A., Hussain, G., Shah, M. A., Nageen, B., Jabeen, F., Selamoğlu, Z., Uçak, İ., Asrar, M., & Adem, S. (2022). A review on phyto-pharmacology of Oxalis corniculata. Comb. Combinatorial Chemistry & High Throughput Screening, 25(7), 1181-1186. https://doi.org/10.2174/1386207324666210813121431
- Täckholm, V. (1974). Students’ Flora of Egypt (2nd ed.). Cairo University, Cairo.
- The plant list (2013). Version1.1.. Available online: http://www.theplantlist.org/ (accessed 1st January, 2021).
- Wang, X., Qian, Y., Li, X., Jia, X., Yan, Z., Han, M., Qiao, M., Ma, X., Chu, Y., Zhou, S., & Yang, W. (2021). Rapid determination of rosmarinic acid and its two bioactive metabolites in the plasma of rats by LC–MS/MS and application to a pharmacokinetics study. Biomedical Chromatography, 35(2), e4984. https://doi.org/10.1002/bmc.4984
- Wang, Z., Ma, C., Tang, S., Xiao, H., Kakiuchi, N., Kida, H., & Hattori, M. (2008). Qualitative and quantitative analysis of Swertia herbs by high performance liquid chromatography-diode array detector-mass spectrometry (HPLC-DAD-MS). Chemical and Pharmaceutical Bulletin, 56(4), 485-490. https://doi.org/10.1248/cpb.56.485
- Wu, B., Zhang, B., Feng, X., Rubens, J.R., Huang, R., Hicks, L.M., Pakrasi, H.B., & Tang, Y.J. (2010). Alternative isoleucine synthesis pathway in cyanobacterial species. Microbiology, 156(2), 596-602. https://doi.org/10.1099/mic.0.031799-0
- Zhang, J., Chen, M., Ju, W., Liu, S., Xu, M., Chu, J., & Wu, T. (2010). Liquid chromatography/Tandem mass spectrometry assay for the simultaneous determination of chlorogenic acid and cinnamic acid in plasma and its application to a pharmacokinetic study. Journal of Pharmaceutical and Biomedical Analysis, 51(3), 685 690. https://doi.org/10.1016/j.jpba.2009.09.039
- Zhao, X., Zhang, S., Liu, D., Yang, M., & Wei, J. (2020). Analysis of flavonoids in dalbergia odorifera by Ultra-Performance Liquid Chromatography with Tandem mass spectrometry. Molecules, 25(2), 389. ; https://doi.org/10.3390/molecules25020389
- Zhong, B., Robinson, N.A., Warner, R.D., Barrow, C.J., Dunshea, F.R., & Suleria, H.A. (2020). LC-ESI-QTOF-MS/MS characterization of seaweed phenolics and their antioxidant potential. Marine Drugs, 18(6), 331. https://doi.org/10.3390/md18060331
Chemical profiling of Oxalis species growing wild in Egypt using HRLC/MS Spectrometry
Year 2022,
Volume: 9 Issue: 4, 426 - 439, 21.12.2022
Amal Draz
,
Salwa Kawashty
Eman Shamso
Hasnaa Hosni
Sameh Hussein
Abstract
Three medicinally promising Oxalis species, namely O. pes-caprae, O. corymbosa & O. latifolia were collected from Egyptian flora and their methanolic extracts were subjected to LC-QTOF-MS analysis to annotate their chemical profiles. Subsequently, 50 compounds belonging to various chemical classes were identified and characterized, of which 34 compounds were first reported from Oxalis L.. Moreover, five flavone compounds were separated and identified from O. pes-caprae; their structures were elucidated using acid hydrolysis, UV/vis, 1H-NMR, and HR-ESI-MS. The chemotaxonomic relationship of the studied species was evaluated and the extracted data were statistically analyzed and classified Oxalis sp. into two distinct clusters. Each cluster was characterized by special chemical features that helped in distinguishing between them.
References
- Almahy, H.A., & Fouda, H.A.R. (2013) Isolation of luteolin 8-C-β-D-glucopyranoside from the roots of Salvadora persica (Rutaceae). Journal of Current Chemical and Pharmaceutical Sciences, 3(1), 49-53.
- Ben Salah, H., Smaoui, S., Abdennabi, R., & Allouche, N. (2019). LC-ESI-MS/MS phenolic profile of Volutaria lippii (L.) Cass. extracts and evaluation of their in vitro antioxidant, Antiacetylcholinesterase, antidiabetic, and antibacterial activities. Evidence-Based Complementary and Alternative Medicine, 2019. https://doi.org/10.1155/2019/9814537
- Brent, L.C., Reiner, J.L., Dickerson, R.R., & Sander, L.C. (2014). Method for characterization of low molecular weight organic acids in atmospheric aerosols using ion chromatography mass spectrometry. Journal of Analytical Chemistry, 86(15), 7328 7336. https://doi.org/10.1021/ac403937e
- Brito, A., Ramirez, J.E., Areche, C., Sepúlveda, B., & Simirgiotis, M.J. (2014). HPLC-UV-MS profiles of phenolic compounds and antioxidant activity of fruits from three citrus species consumed in Northern Chile. Molecules, 19(11), 17400 17421. https://doi.org/10.3390/molecules191117400
- Cao-Ngoc, P., Leclercq, L., Rossi, J.C., Hertzog, J., Tixier, A.S., Chemat, F., Nasreddine, R., Al HamouiDitBanni, G., Nehmé, R., Schmitt-Kopplin, P., & Cottet, H. (2020). Water-based extraction of bioactive principles from black currant leaves and chrysanthellum americanum: A comparative study. Foods, 9(10), 1478. https://doi.org/10.3390/foods9101478
- Cocuron, J.C., & Alonso, A.P. (2014). Liquid chromatography tandem mass spectrometry for measuring ¹³C-labeling in intermediates of the glycolysis and pentose phosphate pathway. Plant Metabolic Flux Analysis, Springer. https://doi.org/10.1007/978-1-62703-688-7_9. PMID: 24222414.
- Dellagreca, M., Previtera, L., Purcaro, R., & Zarrelli, A. (2009). Phytotoxic Aromatic Constituents of Oxalis pes-caprae. Chemistry & Biodiversity, 6(1), 459-465. https://doi.org/10.1002/cbdv.200800179
- Draz, A.A., Shamso, E.M., Hosni, H.A., Kawashty, S.A., & Hussein, S.R. (2021). Comparative study of Oxalis L. species growing wild in Egypt: GC-MS analysis and chemosystematic significance. Egyptian Journal of Chemistry, 64(9), 5251 5256. https://doi.org/10.21608/EJCHEM.2021.72328.3592
- Eissa, M.A., Hashim, Y.Z., El-Kersh, D.M., Abd-Azziz, S.S., Salleh, H.M., Isa, M.L.M., & Abd Warif, N.M. (2020). Metabolite Profiling of Aquilaria malaccensis leaf extract using Liquid Chromatography-Q-TOF-Mass spectrometry and investigation of its potential antilipoxygenase activity in-vitro. Processes, 8(2), 202. https://doi.org/10.3390/pr8020202
- El-Khanagry, S.S.G. (2005). New records of dicotyledonous taxa to the flora of Egypt. Bulletin of Faculty of Agriculture, Cairo University, 56(1), 89-105.
- Gamir, J., Pastor, V., Cerezo, M., & Flors, V. (2012). Identification of indole-3- carboxylic acid as mediator of priming against cucumerina. Plant Physiology and Biochemistry, 61, 169-179. https://doi.org/10.1016/j.plaphy.2012.10.004
- Gaspar, M.C., Fonseca, D.A., Antunes, M.J., Frigerio, C., Gomes, N.G., Vieira, M., Santos, A.E., Cruz, M.T., Cotrim, M.D., & Campos, M.G. (2018). Polyphenolic characterisation and bioactivity of an Oxalis pes-caprae L. leaf extract. Natural Product Research, 32, 732-738. https://doi.org/10.1080/14786419.2017.1335728
- Gervasoni, J., Schiattarella, A., Giorgio, V., Primiano, A., Russo, C., Tesori, V., Scaldaferri, F., Urbani, A., Zuppi, C., & Persichilli, S. (2016). Validation of an LC-MS/MS method for urinary lactulose and mannitol quantification: Results in patients with irritable bowel syndrome. Disease Markers, 2016, ID 5340386, 6. https://doi.org/10.1155/2016/5340386
- Güçlütürk, I., Detsi, A., Weiss, E.K., Ioannou, E., Roussis, V., & Kefalas, P. (2012). Evaluation of anti‐oxidant activity and identification of major polyphenolics of the invasive weed Oxalispes caprae. Phytochemical Analysis, 23(6), 642 646. https://doi.org/10.1002/pca.2367
- Guerrero, R.F., Valls-Fonayet, J., Richard, T., & Cantos-Villar, E. (2020). A rapid quantification of stilbene content in wine by ultra-high pressure liquid chromatography–Mass spectrometry. Food Control, 108, 106821. https://doi.org/10.1016/j.foodcont.2019.106821
- Hassan, W.H., Abdelaziz, S., & Al Yousef, H.M. (2019). Chemical composition and biological activities of the aqueous fraction of Parkinsonea aculeata L. growing in Saudi Arabia. Arabian Journal of Chemistry, 12(3), 377-387. https://doi.org/10.1016/j.arabjc.2018.08.003
- Hussein, S.R., Latif, R.R.A., Marzouk, M.M., Elkhateeb, A., Mohammed, R.S., Soliman, A.A., & Abdel-Hameed, E.S.S. (2018). Spectrometric analysis, phenolics isolation and cytotoxic activity of Stipagrostis plumosa (Family Poaceae). Chemical Papers-Chemicke Zvesti, 72(1), 29-37. https://doi.org/10.1007/s11696-017-0254-0
- Jin, J., Lao, J., Zhou, R., He, W., Qin, Y., Zhong, C., Xie, J., Liu, H., Wan, D., Zhang, S., & Qin, Y. (2018). Simultaneous identification and dynamic analysis of saccharides during steam processing of rhizomes of Polygonatum cyrtonema by HPLC–QTOF–MS/MS. Molecules, 23(11), 2855. https://doi.org/10.3390/molecules23112855
- Kang, J., Price, W.E., Ashton, J., Tapsell, L.C., & Johnson, S. (2016). Identification and characterization of phenolic compounds in hydromethanolic extracts of sorghum whole grains by LC ESI MSn. Food Chemistry, 211, 215 226. https://doi.org/10.1016/j.foodchem.2016.05.052
- Krasteva, I., & Nikolov, S. (2008). Flavonoids in Astragalus corniculatus. Quím Nova, 31, 59-60. https://doi.org/10.1590/S0100-40422008000100012
- Kumarasamy, Y., Byres, M., Cox, P.J., Delazar, A., Jaspars, M., Nahar, L., Shoeb, M., & Sarker, S.D. (2004). Isolation, structure elucidation, and biological activity of flavone 6-C-glycosides from Alliaria petiolata. Chemistry of Natural Compounds, 40(2), 122-128.
- Lin, Y.T., Mao, Y.W., Imtiyaz, Z., Chiou, W.F., & Lee, M.H. (2020). Comprehensive LC-MS/MS-based phytochemical perspectives and osteogenic effects of Uraria crinita. Food Function, 11(6), 5420-5431. https://doi.org/10.1039/D0FO00782J
- Llorach, R., Urpi-Sarda, M., Jauregui, O., Monagas, M., & Andres-Lacueva, C. (2009). An LC-MS-based metabolomics approach for exploring urinary metabolome modifications after cocoa consumption. Journal of Proteome Research, 8(11), 5060 5068. https://doi.org/10.1021/pr900470a
- Lourteig, A. (2000). Oxalis L., subgenera Monoxalis (Small) Lourt., Oxalis y Trifidus Lourt. Bradea, 7(2), 201–629.
- Lucas, A.R. (2021). Viruses as therapeutics: Methods and protocols. Springer.
- Marzouk, M.M., Hussein, S.R., Elkhateeb, A., El-shabrawy, M., Abdel-Hameed, E.S.S., & Kawashty, S.A. (2018). Comparative study of Mentha species growing wild in Egypt: LC-ESI-MS analysis and chemosystematic significance. Journal of Applied Pharmaceutical Science, 8, 116-122. https://doi.org/10.7324/JAPS.2018.8816
- MassBank Europe, Mass Spectral DataBase. Available online: https://massbank.eu/MassBank/ (accessed on 19thJanuary, 2022).
- Minitab 21, Statistical & Data Analysis Software. Available online: https://www.minitab.com/en-us/support/downloads/ (accessed on 17thFebruary, 2022).
- Oberlander, K.C., Dreyer, L.L., & Elser, K.J. (2002). Biogeographv of Oxalis (Oxalidaceae) in South Africa: A preliminary study. Bothalia. African Biodiversity & Conservation, 32(1), 97-100. https://doi.org/10.4102/abc.v32i1.472
- Prasad Pandey, B., Prakash Pradhan, S., & Adhikari, K. (2020). LC‐ESI‐QTOF‐MS for the profiling of the metabolites and in vitro enzymes inhibition activity of Bryophyllum pinnatum and Oxalis corniculata collected from Ramechhap District of Nepal. Chemistry & Biodiversity, 17, e2000155. https://doi.org/10.1002/cbdv.202000155
- Ricciutelli, M., Moretti, S., Galarini, R., Sagratini, G., Mari, M., Lucarini, S., Vittori, S., & Caprioli, G. (2019). Identification and quantification of new isomers of isopropyl-malic acid in wine by LC IT and LC Q Orbitrap. Food Chemistry, 294, 390 396. https://doi.org/10.1016/j.foodchem.2019.05.068
- Ruan, J., Yan, J., Zheng, D., Sun, F., Wang, J., Han, L., Zhang, Y., & Wang, T. (2019). Comprehensive chemical profiling in the ethanol extract of Plucheaindica aerial parts by liquid chromatography/mass spectrometry analysis of its silica gel column chromatography fractions. Molecules, 24(15), 2784. https://doi.org/10.3390/molecules24152784
- Sarfraz, I., Rasul, A., Hussain, G., Shah, M. A., Nageen, B., Jabeen, F., Selamoğlu, Z., Uçak, İ., Asrar, M., & Adem, S. (2022). A review on phyto-pharmacology of Oxalis corniculata. Comb. Combinatorial Chemistry & High Throughput Screening, 25(7), 1181-1186. https://doi.org/10.2174/1386207324666210813121431
- Täckholm, V. (1974). Students’ Flora of Egypt (2nd ed.). Cairo University, Cairo.
- The plant list (2013). Version1.1.. Available online: http://www.theplantlist.org/ (accessed 1st January, 2021).
- Wang, X., Qian, Y., Li, X., Jia, X., Yan, Z., Han, M., Qiao, M., Ma, X., Chu, Y., Zhou, S., & Yang, W. (2021). Rapid determination of rosmarinic acid and its two bioactive metabolites in the plasma of rats by LC–MS/MS and application to a pharmacokinetics study. Biomedical Chromatography, 35(2), e4984. https://doi.org/10.1002/bmc.4984
- Wang, Z., Ma, C., Tang, S., Xiao, H., Kakiuchi, N., Kida, H., & Hattori, M. (2008). Qualitative and quantitative analysis of Swertia herbs by high performance liquid chromatography-diode array detector-mass spectrometry (HPLC-DAD-MS). Chemical and Pharmaceutical Bulletin, 56(4), 485-490. https://doi.org/10.1248/cpb.56.485
- Wu, B., Zhang, B., Feng, X., Rubens, J.R., Huang, R., Hicks, L.M., Pakrasi, H.B., & Tang, Y.J. (2010). Alternative isoleucine synthesis pathway in cyanobacterial species. Microbiology, 156(2), 596-602. https://doi.org/10.1099/mic.0.031799-0
- Zhang, J., Chen, M., Ju, W., Liu, S., Xu, M., Chu, J., & Wu, T. (2010). Liquid chromatography/Tandem mass spectrometry assay for the simultaneous determination of chlorogenic acid and cinnamic acid in plasma and its application to a pharmacokinetic study. Journal of Pharmaceutical and Biomedical Analysis, 51(3), 685 690. https://doi.org/10.1016/j.jpba.2009.09.039
- Zhao, X., Zhang, S., Liu, D., Yang, M., & Wei, J. (2020). Analysis of flavonoids in dalbergia odorifera by Ultra-Performance Liquid Chromatography with Tandem mass spectrometry. Molecules, 25(2), 389. ; https://doi.org/10.3390/molecules25020389
- Zhong, B., Robinson, N.A., Warner, R.D., Barrow, C.J., Dunshea, F.R., & Suleria, H.A. (2020). LC-ESI-QTOF-MS/MS characterization of seaweed phenolics and their antioxidant potential. Marine Drugs, 18(6), 331. https://doi.org/10.3390/md18060331