Natural Products and Bioprospecting    2023, Vol. 13 Issue (6) : 44-44     DOI: 10.1007/s13659-023-00406-y
ORIGINAL ARTICLES |
Untargeted metabolomics analysis of four date palm (Phoenix dactylifera L.) cultivars using MS and NMR
Shuruq Alsuhaymi1, Upendra Singh1, Inas Al-Younis1, Najeh M. Kharbatia2, Ali Haneef3, Kousik Chandra1, Manel Dhahri4, Mohammed A. Assiri5, Abdul-Hamid Emwas2, Mariusz Jaremko1,6
1. Biological and Environmental Science and Engineering Division, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Kingdom of Saudi Arabia;
2. Core Labs, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Kingdom of Saudi Arabia;
3. King Abdullah International Medical Research Center (KAIMRC), King Abdullah Int Medical Research Center, NGHA, Jeddah, Kingdom of Saudi Arabia;
4. Biology Department, Faculty of Science, Taibah University, 46423, Yanbu Branch, Yanbu, Saudi Arabia;
5. Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia;
6. Smart-Health Initiative and Red Sea Research Center, Division of Biological and Environmental Sciences and Engineering, King Abdullah University of Science and Technology, P. O. Box 4700, 23955-6900, Thuwal, Saudi Arabia
Download: PDF(4597 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Since ancient times, the inhabitants of dry areas have depended on the date palm (Phoenix dactylifera L.) as a staple food and means of economic security. For example, dates have been a staple diet for the inhabitants of the Arabian Peninsula and Sahara Desert in North Africa for millennia and the local culture is rich in knowledge and experience with the benefits of dates, suggesting that dates contain many substances essential for the human body. Madinah dates are considered one of the most important types of dates in the Arabian Peninsula, with Ajwa being one of the most famous types and grown only in Madinah, Saudi Arabia. Date seeds are traditionally used for animal feed, seed oil production, cosmetics, and as a coffee substitute. Phytochemical compounds that have been detected in date fruits and date seeds include phenolic acids, carotenoids, and flavonoids. Phenolic acids are the most prevalent bioactive constituents that contribute to the antioxidant activity of date fruits. The bioactive properties of these phytochemicals are believed to promote human health by reducing the risk of diseases such as chronic inflammation. Ajwa dates especially are thought to have superior bioactivity properties. To investigate these claims, in this study, we compare the metabolic profiles of Ajwa with different types of dates collected from Saudi Arabia and Tunisia. We show by UHPLC-MS that date seeds contain several classes of flavonoids, phenolic acids, and amino acid derivatives, including citric acid, malic acid, lactic acid, and hydroxyadipic acid. Additionally, GC–MS profiling showed that date seeds are richer in metabolite classes, such as hydrocinnamic acids (caffeic, ferulic and sinapic acids), than flesh samples. Deglet N fruit extract (minimum inhibitory concentration: 27 MIC/μM) and Sukkari fruit extract (IC50: 479±0.58μg /mL) have higher levels of antibacterial and antioxidative activity than Ajwa fruits. However, the seed analysis showed that seed extracts have better bioactivity effects than fruit extracts. Specifically, Ajwa extract showed the best MIC and strongest ABTS radical-scavenging activity among examined seed extracts (minimum inhibitory concentration: 20 μM; IC50: 54±3.61μg /mL). Our assays are a starting point for more advanced in vitro antibacterial models and investigation into the specific molecules that are responsible for the antioxidative and anti-bacterial activities of dates.
Keywords Metabolomics      GC–MS      UHPLC-MS      NMR      Date palm      Phytochemicals     
Fund:The authors would like to thank King Abdullah University of Science and Technology (KAUST) for access to the Core Labs facilities. This publication is based on work supported by KAUST Smart Health Initiative grants (SHI REI 4447) (MJ) and through baseline-funds (MJ).
Corresponding Authors: Abdul-Hamid Emwas,E-mail:abdelhamid.emwas@kaust.edu.sa;Mariusz Jaremko,E-mail:Mariusz.jaremko@kaust.edu.sa     E-mail: abdelhamid.emwas@kaust.edu.sa;Mariusz.jaremko@kaust.edu.sa
Issue Date: 26 December 2023
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Shuruq Alsuhaymi
Upendra Singh
Inas Al-Younis
Najeh M. Kharbatia
Ali Haneef
Kousik Chandra
Manel Dhahri
Mohammed A. Assiri
Abdul-Hamid Emwas
Mariusz Jaremko
Trendmd:   
Cite this article:   
Shuruq Alsuhaymi,Upendra Singh,Inas Al-Younis, et al. Untargeted metabolomics analysis of four date palm (Phoenix dactylifera L.) cultivars using MS and NMR[J]. Natural Products and Bioprospecting, 2023, 13(6): 44-44.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-023-00406-y     OR     http://npb.kib.ac.cn/EN/Y2023/V13/I6/44
[1] Zohary D, Spiegel-Roy P. Beginnings of Fruit Growing in the Old World: Olive, grape, date, and fig emerge as important Bronze Age additions to grain agriculture in the Near East. Science. 1975;187(4174):319-27.
[2] Chao CT, Krueger RR. The date palm (Phoenix dactylifera L.): overview of biology, uses, and cultivation. HortScience. 2007;42(5):1077-82.
[3] Al-Alawi RA, et al. Date palm tree (Phoenix dactylifera L.): natural products and therapeutic options. Front Plant Sci. 2017;8:845.
[4] Banat F, Al-Asheh S, Al-Makhadmeh L. Evaluation of the use of raw and activated date pits as potential adsorbents for dye containing waters. Process Biochem. 2003;39(2):193-202.
[5] Barreveld WH, Food and Agriculture Organization of the United Nations, Date palm products. 1993: Food and Agriculture Organization of the United Nations.
[6] Bhat RA, Hakeem K, Dervash MA. Phytomedicine: a treasure of pharmacologically active products from plants. Cambridge: Academic Press; 2021.
[7] Ghnimi S, et al. Date fruit (Phoenix dactylifera L.): an underutilized food seeking industrial valorization. NFS J. 2017;6:1-10.
[8] Al-Farsi MA, Lee CY. Nutritional and functional properties of dates: a review. Crit Rev Food Sci Nutr. 2008;48(10):877-87.
[9] Gnanamangai B, et al. Analysis of antioxidants and nutritional assessment of date palm fruits. Sustain Agric Rev. 2019;34:19-40.
[10] Mohamed HI, et al. Date palm (Phoenix dactylifera L.) secondary metabolites: bioactivity and pharmaceutical potential. Phytomedicine. 2021;483-531. https://doi.org/10.1016/B978-0-12-824109-7.00018-2.
[11] Vayalil PK. Date fruits (Phoenix dactylifera Linn): an emerging medicinal food. Crit Rev Food Sci Nutr. 2012;52(3):249-71.
[12] Adeosun AM, et al. Phytochemical, minerals and free radical scavenging profiles of Phoenix dactilyfera L. seed extract. J Taibah Univ Med Sci. 2016;11(1):1-6.
[13] El Arem A, et al. Hepatoprotective activity of date fruit extracts against dichloroacetic acid-induced liver damage in rats. J Funct Foods. 2014;9:119-30.
[14] Farag MA, Otify A, Baky MH. Phoenix Dactylifera L. date fruit by-products outgoing and potential novel trends of phytochemical, nutritive and medicinal merits. Food Rev Int. 2023;39(1):488-510. https://doi.org/10.1080/87559129.2021.1918148.
[15] Mohamed DA, Al-Okbi SY. In vivo evaluation of antioxidant and anti-inflammatory activity of different extracts of date fruits in adjuvant arthritis. Pol J Food Nutr Sci. 2004;13(54):397-402.
[16] Taleb H, et al. Chemical characterisation and the anti-inflammatory, anti-angiogenic and antibacterial properties of date fruit (Phoenix dactylifera L.). J Ethnopharmacol. 2016;194:457-68.
[17] Niazi S, et al. Date palm: composition, health claim and food applications. Int J Pub Health Health Syst. 2017;2:9-17.
[18] Velu G, Palanichamy V, Rajan AP. Phytochemical and pharmacological importance of plant secondary metabolites in modern medicine, in Bioorganic phase in natural food: an overview. 2018, Springer. 135-156.
[19] Ghazzawy HS, et al. Impact of geographical distribution on genetic variation of two date palm cultivars in arid regions. Fresenius Environ Bull. 2021;30(10):11513-23.
[20] Ghazzawy HS, Alqahtani N, Mansour H. Climate change, irrigation systems, nitrogen levels and their impact on the quality of wheat and date palm in the semi arid regions. 2022. https://www.researchgate.net/publication/361231068_CLIMATE_CHANGE_IRRIGATION_SYSTEMS_NITROGEN_LEVELS_AND_THEIR_IMPACT_ON_THE_QUALITY_OF_WHEAT_AND_DATE_PALM_IN_THE_SEMI-ARID_REGIONS_2022.
[21] Mohammed M, et al. The combined effects of precision-controlled temperature and relative humidity on artificial ripening and quality of date fruit. Foods. 2021;10(11):2636.
[22] El-Beltagi HS, et al. Physiological response, phytochemicals, antioxidant, and enzymatic activity of date palm (Phoenix dactylifera L.) cultivated under different storage time, harvesting stages, and temperatures. Saudi J Biol Sci. 2023;30(2):103818. https://doi.org/10.1016/j.sjbs.2023.103818.
[23] Schmidt H. Chronic disease prevention and health promotion. Public health ethics: cases spanning the globe, 2016: 137-176.
[24] Ávila-Escalante ML, et al. The effect of diet on oxidative stress and metabolic diseases—clinically controlled trials. J Food Biochem. 2020;44(5): e13191.
[25] Rani V, et al. Oxidative stress and metabolic disorders: pathogenesis and therapeutic strategies. Life Sci. 2016;148:183-93.
[26] Ciumărnean L, et al. The effects of flavonoids in cardiovascular diseases. Molecules. 2020;25(18):4320.
[27] Neelam K, et al. Fructus lycii: a natural dietary supplement for amelioration of retinal diseases. Nutrients. 2021;13(1):246.
[28] Kopustinskiene DM, et al. Flavonoids as anticancer agents. Nutrients. 2020;12(2):457.
[29] Maleki SJ, Crespo JF, Cabanillas B. Anti-inflammatory effects of flavonoids. Food Chem. 2019;299: 125124.
[30] Emwas A-H, et al. Fluxomics-new metabolomics approaches to monitor metabolic pathways. Front Pharmacol. 2022;13: 805782.
[31] Al-Farsi M, et al. Compositional and functional characteristics of dates, syrups, and their by-products. Food Chem. 2007;104(3):943-7.
[32] Dunn WB, et al. Procedures for large-scale metabolic profiling of serum and plasma using gas chromatography and liquid chromatography coupled to mass spectrometry. Nat Protoc. 2011;6(7):1060-83.
[33] Gibney MJ, et al. Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005;82(3):497-503.
[34] Emwas A-H, et al. Pharmacometabolomics: a new horizon in personalized medicine, in metabolomics-methodology and applications in medical sciences and life sciences. 2021, IntechOpen.
[35] Emwas A-HM, et al. You are what you eat: application of metabolomics approaches to advance nutrition research. Foods. 2021;10(6):1249.
[36] Szczepski K et al. Metabolic biomarkers in cancer, in Metabolomics. 2023, Elsevier. 173-198.
[37] Al-Nemi R, et al. Untargeted metabolomic profiling and antioxidant capacities of different solvent crude extracts of Ephedra foeminea. Metabolites. 2022;12(5):451.
[38] Emwas A-H, et al. NMR spectroscopy for metabolomics research. Metabolites. 2019;9(7):123.
[39] Chandra K, et al. The robust NMR toolbox for metabolomics. Mol Omics. 2021;17(5):719-24.
[40] Chandra K, et al. NMR-based metabolomics with enhanced sensitivity. RSC Adv. 2021;11(15):8694-700.
[41] Saleh MS, et al. Correlation of FT-IR fingerprint and α-glucosidase inhibitory activity of salak (Salacca zalacca) fruit extracts utilizing orthogonal partial least square. Molecules. 2018;23(6):1434.
[42] Aziz Z, et al. FTIR and HPLC-based metabolomics of yacon leaves extracts (Smallanthus sonchifolius [Poepp & Endl.] H. Robinson) from two locations in Indonesia. Indonesian J Chem. 2020;20(3):567-78.
[43] Fiehn O. Metabolomics by gas chromatography-mass spectrometry: combined targeted and untargeted profiling. Curr Protoc Mol Biol. 2016;114(1):30.4.1-30.4.32.
[44] Umar AH, et al. Untargeted metabolomics analysis using FTIR and UHPLC-Q-Orbitrap HRMS of two Curculigo species and evaluation of their antioxidant and α-glucosidase inhibitory activities. Metabolites. 2021;11(1):42.
[45] Farag MA, et al. Metabolomic fingerprints of 21 date palm fruit varieties from Egypt using UPLC/PDA/ESI-qTOF-MS and GC-MS analyzed by chemometrics. Food Res Int. 2014;64:218-26.
[46] AlShwyeh H, Almahasheer H. Glucose content of 35 Saudi Arabian date fruits (Phoenix dactylifera L.). J Saudi Soc Agric Sci. 2022;21(6):420-4.
[47] Ahmed J, Al-Jasass FM, Siddiq M. Date fruit composition and nutrition. Dates: postharvest science, processing technology and health benefits. Wiley; 2014, p. 261-283.
[48] El-Mergawi R, Al-Humaid A, El-Rayes D. Phenolic profiles and antioxidant activity in seeds of ten date cultivars from Saudi Arabia. J Food Agric Environ. 2016;14(2):38-43.
[49] Kumar N, Goel N. Phenolic acids: Natural versatile molecules with promising therapeutic applications. Biotechnol Rep. 2019;24: e00370.
[50] Ullah A, et al. Important flavonoids and their role as a therapeutic agent. Molecules. 2020;25(22):5243.
[51] Das S, Acharya J, De B. Metabolite profiling, antioxidant activity, and glycosidase inhibition property of the mesocarp tissue extracts of sugar date palm [Phoenix sylvestris (L.) Roxb.] fruits. Int J Food Properties. 2017;20(12):2982-93.
[52] Abedi F, Razavi BM, Hosseinzadeh H. A review on gentisic acid as a plant derived phenolic acid and metabolite of aspirin: comprehensive pharmacology, toxicology, and some pharmaceutical aspects. Phytother Res. 2020;34(4):729-41.
[53] Joshi R, et al. Antioxidant activity and free radical scavenging reactions of gentisic acid: In-vitro and pulse radiolysis studies. Free Radic Res. 2012;46(1):11-20.
[54] Qian W, et al. In vitro antibacterial activity and mechanism of vanillic acid against carbapenem-resistant Enterobacter cloacae. Antibiotics. 2019;8(4):220.
[55] Chen JH, Ho C-T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J Agric Food Chem. 1997;45(7):2374-8.
[56] Lv L, et al. Recent progresses in the pharmacological activities of caffeic acid phenethyl ester. Naunyn Schmiedebergs Arch Pharmacol. 2021;394(7):1327-39.
[57] Chao P-C, Hsu C-C, Yin M-C. Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice. Nutr Metab. 2009;6(1):1-8.
[58] Nićiforović N, Abramovič H. Sinapic acid and its derivatives: natural sources and bioactivity. Compr Rev Food Sci Food Saf. 2014;13(1):34-51.
[59] Anderson RF, et al. Green tea catechins partially protect DNA from· OH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals. Carcinogenesis. 2001;22(8):1189-93.
[60] Kim J, et al. Application of green tea catechins, polysaccharides, and flavonol prevent fine dust induced bronchial damage by modulating inflammation and airway cilia. Sci Rep. 2021;11(1):1-11.
[61] Yin W, et al. Anti-inflammatory effects of grape seed procyanidin B2 on a diabetic pancreas. Food Funct. 2015;6(9):3065-71.
[62] Gutierrez-Salmean G, et al. Effects of (-)-epicatechin on molecular modulators of skeletal muscle growth and differentiation. J Nutr Biochem. 2014;25(1):91-4.
[63] Albayrak A, et al. Gastric anti-ulcerative and anti-inflammatory activity of metyrosine in rats. Pharmacol Rep. 2010;62(1):113-9.
[64] Seifikalhor M, et al. Diverse role of γ-aminobutyric acid in dynamic plant cell responses. Plant Cell Rep. 2019;38(8):847-67.
[65] Maqsood S, et al. Bioactive compounds from date fruit and seed as potential nutraceutical and functional food ingredients. Food Chem. 2020;308: 125522.
[66] Hamad I, et al. Metabolic analysis of various date palm fruit (Phoenix dactylifera L.) cultivars from Saudi Arabia to assess their nutritional quality. Molecules. 2015;20(8):13620-41.
[67] Alahyane A, et al. Bioactive compounds and antioxidant activity of seventeen Moroccan date varieties and clones (Phoenix dactylifera L.). S Afr J Bot. 2019;121:402-9.
[68] Harkat H, et al. Assessment of biochemical composition and antioxidant properties of Algerian date palm (Phoenix dactylifera L.) seed oil. Plants. 2022;11(3):381.
[69] Kadum H, et al. Bioactive compounds responsible for antioxidant activity of different varieties of date (Phoenix dactylifera L.) elucidated by 1H-NMR based metabolomics. Int J Food Properties. 2019;22(1):462-76.
[70] Dhahri M, et al. Extraction, characterization, and antioxidant activity of polysaccharides from ajwa seed and flesh. Separations. 2023;10(2):103.
[71] Biglari F, AlKarkhi AF, Easa AM. Antioxidant activity and phenolic content of various date palm (Phoenix dactylifera) fruits from Iran. Food Chem. 2008;107(4):1636-41.
[72] Al-Shwyeh HA. Date palm (Phoenix dactylifera L.) fruit as potential antioxidant and antimicrobial agents. J Pharm Bioallied Sci. 2019;11(1):1.
[73] Salem MA, et al. Protocol: a fast, comprehensive and reproducible one-step extraction method for the rapid preparation of polar and semi-polar metabolites, lipids, proteins, starch and cell wall polymers from a single sample. Plant Methods. 2016;12(1):1-15.
[74] Tsugawa H, et al. MS-DIAL: data-independent MS/MS deconvolution for comprehensive metabolome analysis. Nat Methods. 2015;12(6):523-6.
[75] Singh U, et al. Compound-specific 1D 1H NMR pulse sequence selection for metabolomics analyses. ACS Omega, 2023.
[76] Chong J, et al. MetaboAnalyst 4.0: towards more transparent and integrative metabolomics analysis. Nucleic Acids Res. 2018;46(W1):W486-94.
[77] Wang X, et al. Design, synthesis and antibacterial evaluation of some new 2-phenyl-quinoline-4-carboxylic acid derivatives. Molecules. 2016;21(3):340.
[78] Re R, et al. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med. 1999;26(9-10):1231-7.
[1] Phanankosi Moyo, Luke Invernizzi, Sephora M. Mianda, Wiehan Rudolph, Andrew W. Andayi, Mingxun Wang, Neil R. Crouch, Vinesh J. Maharaj. Prioritised identification of structural classes of natural products from higher plants in the expedition of antimalarial drug discovery[J]. Natural Products and Bioprospecting, 2023, 13(5): 37-37.
[2] Asih Triastuti, Marieke Vansteelandt, Fatima Barakat, Carlos Amasifuen, Patricia Jargeat, Mohamed Haddad. Untargeted metabolomics to evaluate antifungal mechanism: a study of Cophinforma mamane and Candida albicans interaction[J]. Natural Products and Bioprospecting, 2023, 13(1): 1-1.
[3] Shah Faisal, Syed Lal Badshah, Bibi Kubra, Abdul, Hamid Emwas, and Mariusz Jaremko. Alkaloids as potential antivirals. A comprehensive review[J]. Natural Products and Bioprospecting, 2023, 13(1): 4-4.
[4] Pablo A. Chacón-Morales, Juan M. Amaro-Luis, Luis Beltrán Rojas Fermín, Rémi Jacquet, Denis Deffieux, Laurent Pouységu, Stéphane Quideau. Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol[J]. Natural Products and Bioprospecting, 2022, 12(3): 20-20.
[5] Pinaki Dey, Joginder Singh, Jagadish Kumar Suluvoy, Kevin Joseph Dilip, Jayato Nayak. Utilization of Swertia chirayita Plant Extracts for Management of Diabetes and Associated Disorders: Present Status, Future Prospects and Limitations[J]. Natural Products and Bioprospecting, 2020, 10(6): 431-443.
[6] Elier Galarraga, Andersson Mavares, Neudo Urdaneta, Rafael E. Rodríguez-Lugo, Juan Manuel Amaro-Luis. Artificial Triterpenoid Fatty Acid Ester Isolated From the Leaves of Phytolacca icosandra L[J]. Natural Products and Bioprospecting, 2020, 10(4): 221-225.
[7] Dezhi Yang, Bin Su, Yancai Bi, Li Zhang, Baoxi Zhang, Junke Song, Yang Lu, Guanhua Du. Preparation and Certification of a New Salvianolic Acid A Reference Material for Food and Drug Research[J]. Natural Products and Bioprospecting, 2020, 10(2): 67-76.
[8] Hai-Li Yu, Qin Long, Wen-Fang Yi, Bao-Jia Yang, Yu Song, Xiao Ding, Shun-Lin Li, Xiao-Jiang Hao. Two New C21 Steroidal Glycosides from the Roots of Cynanchum paniculatum[J]. Natural Products and Bioprospecting, 2019, 9(3): 209-214.
[9] Hou-Chao Xu, Kun Hu, Han-Dong Sun, Pema-Tenzin Puno. Four 14(13→12)-Abeolanostane Triterpenoids with 6/6/5/6-Fused Ring System from the Roots of Kadsura coccinea[J]. Natural Products and Bioprospecting, 2019, 9(3): 165-173.
[10] S. Manimaran, K. SambathKumar, R. Gayathri, K. Raja, N. Rajkamal, M. Venkatachalapathy, G. Ravichandran, C. Lourdu EdisonRaj. Medicinal Plant Using Ground State Stabilization of Natural Antioxidant Curcumin by Keto-Enol Tautomerisation[J]. Natural Products and Bioprospecting, 2018, 8(5): 369-390.
[11] Gao-Wei Li, Han Liu, Feng Qiu, Xiao-Juan Wang, Xin-Xiang Lei. Residual Dipolar Couplings in Structure Determination of Natural Products[J]. Natural Products and Bioprospecting, 2018, 8(4): 279-295.
[12] Qi Zhao, Jia-Le Zhang, Fei Li. Application of Metabolomics in the Study of Natural Products[J]. Natural Products and Bioprospecting, 2018, 8(4): 321-334.
[13] Liang-Yan Liu, Han Sun, Christian Griesinger, Ji-Kai Liu. The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp[J]. Natural Products and Bioprospecting, 2016, 6(1): 41-48.
[14] Marie Pascaline Rahelivao, Margit Gruner, Hanta Andriamanantoanina, Ingmar Bauer, Hans-Joachim Knölker. Brown Algae(Phaeophyceae) from the Coast of Madagascar:preliminary Bioactivity Studies and Isolation of Natural Products[J]. Natural Products and Bioprospecting, 2015, 5(5): 223-235.
[15] Alan Rodrigues Teixeira MACHADO, Gisele Avelar LAGE, Felipe da Silva MEDEIROS, José Dias de Souza FILHO, Lúcia Pinheiro Santos PIMENTA. Quantitative analysis of trigonelline in some Annona species by proton NMR spectroscopy[J]. Natural Products and Bioprospecting, 2013, 3(4): 158-160.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed