Comprehensive phytochemical profiling of Garden Cress (Lepidium sativum L.) seeds using UPLC-ESI-MS/MS

Document Type : Original Article

Authors

1 Department of Pharmacognosy, Faculty of Pharmacy, Damanhur University, Egypt.

2 Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University, Egypt.

Abstract

Lepidium sativum or Hab-el Rashad is extensively cultivated as a food supplement to preserve a healthy state of human considering its nutritional and therapeutical properties. Nutritional aspect as it is a valuable source of proteins, carbohydrates, minerals, and vitamins. Besides, it has a therapeutic aspect, as previous research proved remarkable biological actions, including antidiabetic, antimicrobial, antioxidant, anticancer and numerous health-controlling effects. In the current study, L. sativum seeds were extracted using 70% ethanol and exposed to ultrahigh-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (UPLC-ESI-MS) to probe its phytoconstituents. This analysis resulted in the annotation of 41 metabolites across several chemical categories, including glucosinolates, alkaloids, flavonoids, fatty acids and hydantoin derivatives. Compounds were annotated by comparing their retention times and fragments with those in an in-house collected chemical compounds database, as well as with data from online dictionaries and previous literature. The drive of this study is to extensively profile the active constituents in L. sativum seeds extract and demonstrate their mass fragmentation patterns in both positive and negative ionization modes. 

Highlights

•    Lepidium sativum is a perfect candidate to treat multiple diseases.
•    UPLC-ESI-MS technique was used to separate and identify phytochemicals in the extract.
•    Hydantoins such as macahydantoin A, C, and D are characteristic compounds of Lepidium.
•     Five chemical classes were detected as amino acids, glucosinolates, and fatty acids.

Keywords

Main Subjects

References

(1) Shabbir F, Eddouks M, Nadeem F, Azeem MW. A brief review on bioactivities and therapeutic potentials of garden cress (Lepidium sativum L.). Ijcbs. 2018;13:36–45. 
(2) Kaiyrkulova A, Li J, Aisa HA. Chemical Constituents of Lepidium sativum Seeds. Chem Nat Compd. 2019;55(4):736–7. 
(3) Attia ES, Amer AH, Hasanein MA. The hypoglycemic and antioxidant activities of garden cress ( Lepidium sativum L.) seed on alloxan-induced diabetic male rats. Nat Prod Res. 2019;33(6):901–5.
(4) IDM’HAND E, MSANDA F, CHERİFİ K. A review of Moroccan Medicinal Plants Used in the Treatment of Hypertension. Int J Nat Life Sci. 2022;6(1):48–78. 
(5) El-Haggar M, El-Hosseiny L, Ghazy NM, El-Fiky FK, El-Hawiet A. Phytochemical investigation, antimicrobial and cytotoxic activities of suspension cultures of Lepidium sativum L. South African J Bot. 2021;138:500–5. 
(6) Painuli S, Quispe C, Herrera-Bravo J, Semwal P, Martorell M, Almarhoon ZM, et al. Nutraceutical Profiling, Bioactive Composition, and Biological Applications of Lepidium sativum L. Oxid Med Cell Longev. 2022;2022:1–20. 
(7) El-salam KHA, Toliba AO, El-shourbagy GA, El-nemr SE. CHEMICAL AND FUNCTIONAL PROPERTIES OF GARDEN CRESS (Lepidium sativum L.) SEEDS POWDER. Zagazig J Agric Res. 2019;46(5):1517–28. 
(8) Emaduldeen HA, Waheeb MQ, Makki MA. Antimicrobial Features of Lepidium sativum L. extract. Iran J War Public Heal. 2023;15(4):387–94. 
(9) AL-SNAFI AE. Chemical Constituents and Pharmacological Effects of Lepidium Sativum-a Review. Int J Curr Pharm Res. 2019;(November):1–10. 
(10) Sakran M, Selim Y, Zidan N. A New Isoflavonoid from Seeds of Lepidium sativum L. and Its Protective Effect on Hepatotoxicity Induced by Paracetamol in Male Rats. Molecules. 2014;19(10):15440–51. 
(11) Alharbi F, S. Baothman O, Zamzami M, Abou Gabal H, Khoja S, Karrouf G, et al. Garden cress (Lepidium sativum L.) seeds enhancing osteogenesis postinduced-bone fracture. Pharmacogn Mag. 2021;17(73):170. 
(12) Kumar N, Singh S. Nutritional composition, nutraceutical aspects, and medicinal benefits of garden cress (Lepidium sativum) seeds – A geographical and processing perspective. Trends Food Sci Technol. 2024;154:104791. 
(13) Basharat R, Kotra V, Loong LY, Mathews A, Kanakal MM, Devi CBP, et al. Ultra Performance Liquid Chromatography (Mini-Review). Orient J Chem. 2021;37(4):847–57. 
(14) Abdallah HM, Farag MA, Algandaby MM, Nasrullah MZ, Abdel-Naim AB, Eid BG, et al. Osteoprotective activity and metabolite fingerprint via uplc/ms and gc/ms of lepidium sativum in ovariectomized rats. Nutrients, 2020;12(7):1–20. 
(15) Andini S, Araya-Cloutier C, Sanders M, Vincken JP. Simultaneous Analysis of Glucosinolates and Isothiocyanates by Reversed-Phase Ultra-High-Performance Liquid Chromatography–Electron Spray Ionization–Tandem Mass Spectrometry. J Agric Food Chem. 2020;68(10):3121–31. 
(16) Connolly EL, Sim M, Travica N, Marx W, Beasy G, Lynch GS, et al. Glucosinolates From Cruciferous Vegetables and Their Potential Role in Chronic Disease: Investigating the Preclinical and Clinical Evidence. Front Pharmacol. 2021;12. 
(17) Abdel-Aty AM, Bassuiny RI, Barakat AZ, Mohamed SA. Upgrading the phenolic content, antioxidant and antimicrobial activities of garden cress seeds using solid-state fermentation by Trichoderma reesei. J Appl Microbiol 2019;127(5):1454–67. 
(18) Tufail T, Khan T, Bader Ul Ain H, Morya S, Shah MA. Garden cress seeds: a review on nutritional composition, therapeutic potential, and industrial utilization. Food Sci Nutr. 2024;12(6):3834–48. 
(19) Carvalho F V., Ribeiro PR. Structural diversity, biosynthetic aspects, and LC-HRMS data compilation and JMP. Mass spectra of isothiocyanates. Acta Chem Scand for the identification of bioactive compounds of Lepidium meyenii. Food Res Int. 2019;125(August):108615. 
(20) Chen R, Wei J, Gao Y. A review of the study of active components and their pharmacology value in Lepidium meyenii (Maca). Phyther Res. 2021;35(12):6706–19. 
(21) Al-Obaid AM, El-Subbagh HI, Khodair A, Elmazar MMA. 5-Substituted-2-thiohydantoin analogs as a novel class of antitumor agents. Anticancer. Drugs1996;7(8):873–80. 
(22) Wang ZD, Sheikh SO, Zhang Y. A simple synthesis of 2-thiohydantoins. Molecules. 2006;11(10):739–50. 
(23) Le A, Ng A, Kwan T, Cusmano-Ozog K, Cowan TM. A rapid, sensitive method for quantitative analysis of underivatized amino acids by liquid chromatography–tandem mass spectrometry (LC–MS/MS). J Chromatogr B. 2014;944:166–74. 
(24) Ibrahim RM, Elmasry GF, Refaey RH, El-Shiekh RA. Lepidium meyenii (Maca) Roots: UPLC-HRMS, Molecular Docking, and Molecular Dynamics. ACS Omega 2022;7(20):17339–57. 
(25) Liu M, Zhang D, Wang X, Zhang L, Han J, Yang M, et al. Simultaneous quantification of niacin and its three main metabolites in human plasma by LC-MS/MS. J. Chromatogr. B Anal. Technol. Biomed. Life Sci.2012;904:107–14. 
(26) Ibrahim RS, El-Mezayen NS, El‐Banna AA. Alleviation of liver cirrhosis and associated portal-hypertension by Astragalus species in relation to their UPLC-MS/MS metabolic profiles: a mechanistic study. Sci Rep. 2022;12(1):1–27. 
(27) Hamed AI, Said R Ben, Kontek B, Al-Ayed AS, Kowalczyk M, Moldoch J, et al. LC–ESI-MS/MS profile of phenolic and glucosinolate compounds in samh flour ( Mesembryanthemum forsskalei Hochst. ex Boiss) and the inhibition of oxidative stress by these compounds in human plasma. Food Res Int. 2016;85:282–90. 
(28) Tafuri S, Cocchia N, Carotenuto D, Vassetti A, Staropoli A, Mastellone V, et al. Chemical analysis of Lepidium meyenii (Maca) and its effects on redox status and on reproductive biology in stallions. Molecules. 2019;24(10):1–12. 
(29) Wang S, Li X, Chen B, Li S, Wang J, Wang J, et al. Dimension-enhanced ultra-high performance liquid chromatography/ion mobility-quadrupole time-of-flight mass spectrometry combined with intelligent peak annotation for the rapid characterization of the multiple components from seeds of descurainia sophia. Phyton-International J Exp Bot. 2022;91(3):541–67. 
(30) Anders Kjaer, Mamoru Ohashi , J. Michael Wilson CD. 1963;17:2143–54. 
(31) Nicolescu TO. Interpretation of mass spectra. Mass Spectrometry. 2017 Jun 7:23-78.
(32) Rodig OR. Spectrometric Identification of Organic Compounds. J Med Chem. 1963;6(6):826–7. 
(33) Suzuki T, Tuzimura K. Mass spectra of amino acid hydantoins. Agric Biol Chem. 1976;40(1):225–6.
(34) Bennouna D, Avice JC, Rosique C, Svilar L, Pontet C, Trouverie J, et al. The impact of genetics and environment on the polar fraction metabolome of commercial Brassica napus seeds: a multi-site study. Seed Sci Res. 2019;29(3):167–78. 
(35) Ousji O, Sleno L. Structural Elucidation of Novel Stable and Reactive Metabolites of Green Tea Catechins and Alkyl Gallates by LC-MS/MS. Antioxidants. 2022;11(9):1635. 
(36) Oszmiański J, Kolniak-Ostek J, Wojdyło A. Application of ultra performance liquid chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS) method for the characterization of phenolic compounds of Lepidium sativum L. sprouts. Eur Food Res Technol. 2013;236(4):699–706. 
(37) Maldini M, Foddai M, Natella F, Petretto GL, Rourke JP, Chessa M, et al. Identification and quantification of glucosinolates in different tissues of Raphanus raphanistrum by liquid chromatography tandem-mass spectrometry. J Food Compos Anal. 2017;61:20–7. 
(38) Della Corte A, Chitarrini G, Di Gangi IM, Masuero D, Soini E, Mattivi F, et al. A rapid LC-MS/MS method for quantitative profiling of fatty acids, sterols, glycerolipids, glycerophospholipids and sphingolipids in grapes. Talanta. 2015;140:52–61. 
(39) Temesgen Bedassa Gudeta, Million Eshete, Mebeaselassie Andargie. Genetic divergence analysis of garden cress (Lepidium sativum L.). Int J Biodivers Conserv. 2013;5(11):770–4. 
(40) Hosny H, Omran N, Handoussa H. Edible seeds with potential anti-obesity impact: A Review. Int J Plant Based Pharm. 2022;2(1):64–81. 
(41) Ibrahim MM, Mounier MM, Bekheet SA. Targeting apoptotic anticancer response with natural glucosinolates from cell suspension culture of Lepidium sativum. J Genet Eng Biotechnol. 2023;21(1):53. 
(42) Vazifeh S, Kananpour P, Khalilpour M, Eisalou SV, Hamblin MR. Anti‐inflammatory and Immunomodulatory Properties of Lepidium sativum. Biomed Res Int. 2022;2022(1):12. 
(43) Ćirić A, Prosen H, Jelikić-Stankov M, Durević P. Evaluation of matrix effect in determination of some bioflavonoids in food samples by LC-MS/MS method. Talanta. 2012;99:780–90. 
 
Journal of Advanced Pharmaceutical Sciences
Volume 2, Issue 1
January 2025
Pages 64-75

Files

Share

How to cite

Statistics