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Planta Med 2021; 87(05): 417-427
DOI: 10.1055/a-1240-6186
Natural Product Chemistry and Analytical Studies
Original Papers

Profiling and Quantification of the Key Phytochemicals from the Drumstick Tree (Moringa oleifera) and Dietary Supplements by UHPLC-PDA-MS

Omer I. Fantoukh 
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
2   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS, USA
3   Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Yan-Hong Wang
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
,
Abidah Parveen 
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
2   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS, USA
4   Department of Pharmaceutical Sciences, Abbottabad University of Science & Technology, Havelian, KPK, Pakistan
,
Mohammed F. Hawwal
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
2   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS, USA
3   Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Gadah A. Al-Hamoud
3   Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Zulfiqar Ali
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
,
Amar G. Chittiboyina
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
,
Ikhlas A. Khan
1   National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS, USA
2   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS, USA
› Author AffiliationsSupported by: U.S. Food and Drug Administration grant number 5U01FD004246-07
Supported by: King Saud University
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Abstract

Moringa oleifera is known as a drumstick tree and is cultivated in the subtropics and tropics. It exhibits antihypertensive and antidiabetic effects. An ultra-high-performance liquid chromatography method was developed for the determination of 9 phytochemicals in M. oleifera leaves and marketed products. The efficient separation was achieved within 7 min with a temperature of 45 °C by using a C-18 column as the stationary phase and water/acetonitrile with 0.05% formic acid as the mobile phase. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The limits of detections of phenolic compounds 1 – 9 were as low as 0.2 µg/mL. The photodiode array detector at 220 and 255 nm wavelengths was recruited for quantification. The key phytochemicals were detected in the range of 0.42 to 2.57 mg/100 mg sample weight in 13 dietary supplements. This study considers the quantitative analysis for lignans in M. oleifera for the first time. Isoquercitrin (5) and quercetin 3-O-(6-O-malonyl)-β−D-glucopyranoside (6) predominates the leaves of M. oleifera with inherent degradable nature detected for compound 6. Niazirin (2) was detected in amounts between 0.010 – 0.049 mg/100 mg while compound 1 was undetectable and potentially an artifact because of the fractionation process. The characterization and confirmation of components were achieved by liquid chromatography-electrospray ionization-mass spectrometry with extractive ion monitoring for the positive and negative ion modes. The developed and validated method is robust and rapid in the conclusive quantification of phytochemicals and authentication of the Moringa samples for quality assurance.

Key words

Moringa oleifera - Moringaceae - niazirin - flavonoids - lignans - UPLC-PDA-MS

Supporting Information

    UV, ESI (−) and (+) mass spectra, and calibration curves of compounds 1–9 are provided as Supporting Information.

  • Supporting Information


Publication History

Received: 24 February 2020

Accepted after revision: 13 August 2020

Article published online:
21 October 2020

© 2020. Thieme. All rights reserved.

Georg Thieme Verlag KG
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  • References

  • 1 Saini RK, Sivanesan I, Keum YS. Phytochemicals of Moringa oleifera: a review of their nutritional, therapeutic and industrial significance. 3 Biotech 2016; 6: 203
    CrossrefPubMedGoogle Scholar
  • 2 Anwar F, Latif S, Ashraf M, Gilani AH. Moringa oleifera: a food plant with multiple medicinal uses. Phytother Res 2007; 21: 17-25
    CrossrefPubMedGoogle Scholar
  • 3 Ganguly S. Indian ayurvedic and traditional medicinal implications of indigenously available plants, herbs and fruits: a review. Int J Res Ayurveda Pharm 2013; 4: 623
    CrossrefPubMedGoogle Scholar
  • 4 Gopalakrishnan L, Doriya K, Kumar DS. Moringa oleifera: a review on nutritive importance and its medicinal application. Food Sci Hum Well 2016; 5: 49-56
    CrossrefPubMedGoogle Scholar
  • 5 Chopra RN, De P. A Preliminary note on the action of the alkaloid of Moringa Pterygosperma (N. O. Moringæ). Ind Med Gaz 1932; 67: 128-130
    PubMedGoogle Scholar
  • 6 Tshabalala T, Ncube B, Madala NE, Nyakudya TT, Moyo HP, Sibanda M, Ndhlala AR. Scribbling the cat: a case of the “miracle” plant, Moringa oleifera . Plants (Basel, Switzerland) 2019; 8: 510
    PubMedGoogle Scholar
  • 7 Leone A, Spada A, Battezzati A, Schiraldi A, Aristil J, Bertoli S. Cultivation, genetic, ethnopharmacology, phytochemistry and pharmacology of Moringa oleifera leaves: an overview. Int J Mol Sci 2015; 16: 12791-12835
    CrossrefPubMedGoogle Scholar
  • 8 Stohs SJ, Hartman MJ. Review of the safety and efficacy of Moringa oleifera . Phytother Res 2015; 29: 796-804
    CrossrefPubMedGoogle Scholar
  • 9 Jaiswal D, Kumar Rai P, Kumar A, Mehta S, Watal G. Effect of Moringa oleifera Lam. leaves aqueous extract therapy on hyperglycemic rats. J Ethnopharmacol 2009; 123: 392-396
    CrossrefPubMedGoogle Scholar
  • 10 Akhtar AH, Ahmad KU. Anti-ulcerogenic evaluation of the methanolic extracts of some indigenous medicinal plants of Pakistan in aspirin-ulcerated rats. J Ethnopharmacol 1995; 46: 1-6
    CrossrefPubMedGoogle Scholar
  • 11 Abd Rani NZ, Husain K, Kumolosasi E. Moringa genus: a review of phytochemistry and pharmacology. Front Pharmacol 2018; 9: 108
    CrossrefPubMedGoogle Scholar
  • 12 Das BR, Kurup PA, Narasimha Rao PL. Antibiotic principle from Moringa pterygosperma. VII. Antibacterial activity and chemical structure of compounds related to pterygospermin. Indian J Med Res 1957; 45: 191-196
    PubMedGoogle Scholar
  • 13 Amaglo NK, Bennett RN, Lo Curto RB, Rosa EAS, Lo Turco V, Giuffrida A, Curto AL, Crea F, Timpo GM. Profiling selected phytochemicals and nutrients in different tissues of the multipurpose tree Moringa oleifera L., grown in Ghana. Food Chem 2010; 122: 1047-1054
    CrossrefPubMedGoogle Scholar
  • 14 Rodríguez-Pérez C, Quirantes-Piné R, Fernández-Gutiérrez A, Segura-Carretero A. Optimization of extraction method to obtain a phenolic compounds-rich extract from Moringa oleifera Lam leaves. Ind Crops Prod 2015; 66: 246-254
    CrossrefPubMedGoogle Scholar
  • 15 Lin H, Zhu H, Tan J, Wang H, Wang Z, Li P, Zhao C, Liu J. Comparative analysis of chemical constituents of Moringa oleifera leaves from China and India by ultra-performance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry. Molecules 2019; 24: 942
    CrossrefPubMedGoogle Scholar
  • 16 Makita C, Chimuka L, Steenkamp P, Cukrowska E, Madala E. Comparative analyses of flavonoid content in Moringa oleifera and Moringa ovalifolia with the aid of UHPLC-qTOF-MS fingerprinting. S Afr J Bot 2016; 105: 116-122
    CrossrefPubMedGoogle Scholar
  • 17 Yan G, Liping S, Yongliang Z. UPLC-Q-Orbitrap-MS(2) analysis of Moringa oleifera leaf extract and its antioxidant, antibacterial and anti-inflammatory activities. Nat Prod Res 2019; 34: 1-5 doi:10.1080/14786419.2019.1573237
    CrossrefPubMedGoogle Scholar
  • 18 Shanker K, Gupta M, Srivastava S, Bawankule D, Pal A, Khanuja S. Determination of bioactive nitrile glycoside(s) in drumstick (Moringa oleifera) by reverse phase HPLC. Food Chem 2007; 105: 376-382
    CrossrefPubMedGoogle Scholar
  • 19 Vongsak B, Sithisarn P, Gritsanapan W. Simultaneous HPLC quantitative analysis of active compounds in leaves of Moringa oleifera Lam. J Chromatogr Sci 2014; 52: 641-645
    CrossrefPubMedGoogle Scholar
  • 20 Bennett RN, Mellon FA, Foidl N, Pratt JH, Dupont MS, Perkins L, Kroon PA. Profiling glucosinolates and phenolics in vegetative and reproductive tissues of the multi-purpose trees Moringa oleifera L. (horseradish tree) and Moringa stenopetala L. J Agric Food Chem 2003; 51: 3546-3553
    CrossrefPubMedGoogle Scholar
  • 21 Sahakitpichan P, Mahidol C, Disadee W, Ruchirawat S, Kanchanapoom T. Unusual glycosides of pyrrole alkaloid and 4′-hydroxyphenylethanamide from leaves of Moringa oleifera . Phytochemistry 2011; 72: 791-795
    CrossrefPubMedGoogle Scholar
  • 22 Francis JA, Jayaprakasam B, Olson LK, Nair MG. Insulin secretagogues from Moringa oleifera with cyclooxygenase enzyme and lipid peroxidation inhibitory activities. Helv Chim Acta 2004; 87: 317-326
    CrossrefPubMedGoogle Scholar
  • 23 Fantoukh OI, Albadry MA, Parveen A, Hawwal MF, Majrashi T, Ali Z, Khan SI, Chittiboyina AG, Khan IA. Isolation, synthesis, and drug interaction potential of secondary metabolites derived from the leaves of miracle tree (Moringa oleifera) against CYP3A4 and CYP2D6 isozymes. Phytomedicine 2019; 60: 153010
    CrossrefPubMedGoogle Scholar
  • 24 Dinkova-Kostova AT, Kostov RV. Glucosinolates and isothiocyanates in health and disease. Trends Mol Med 2012; 18: 337-347
    CrossrefPubMedGoogle Scholar
  • 25 Ganeshpurkar A, Saluja AK. The pharmacological potential of rutin. Saudi Pharm J 2017; 25: 149-164
    CrossrefPubMedGoogle Scholar
  • 26 Habtemariam S, Varghese G. Extractability of rutin in herbal tea preparations of Moringa stenopetala leaves. Beverages 2015; 1: 169-182
    CrossrefPubMedGoogle Scholar
  • 27 Makita C, Madala NE, Cukrowska E, Abdelgadir H, Chimuka L, Steenkamp P, Ndhlala AR. Variation in pharmacologically potent rutinoside-bearing flavonoids amongst twelve Moringa oleifera Lam. cultivars. S Afr J Bot 2017; 112: 270-274
    CrossrefPubMedGoogle Scholar
  • 28 Ramakrishna A, Ravishankar GA. Influence of abiotic stress signals on secondary metabolites in plants. Plant Signal Behav 2011; 6: 1720-1731
    CrossrefPubMedGoogle Scholar
  • 29 Rodriguez-Perez C, Gilbert-Lopez B, Mendiola JA, Quirantes-Pine R, Segura-Carretero A, Ibanez E. Optimization of microwave-assisted extraction and pressurized liquid extraction of phenolic compounds from Moringa oleifera leaves by multiresponse surface methodology. Electrophoresis 2016; 37: 1938-1946
    CrossrefPubMedGoogle Scholar
  • 30 Makris DP, Rossiter JT. An investigation on structural aspects influencing product formation in enzymic and chemical oxidation of quercetin and related flavonols. Food Chem 2002; 77: 177-185
    CrossrefPubMedGoogle Scholar
  • 31 Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002; 13: 572-584
    CrossrefPubMedGoogle Scholar
  • 32 Valentová K, Vrba J, Bancířová M, Ulrichová J, Křen V. Isoquercitrin: pharmacology, toxicology, and metabolism. Food Chem Toxicol 2014; 68: 267-282
    CrossrefPubMedGoogle Scholar
  • 33 Coppin JP, Xu Y, Chen H, Pan MH, Ho CT, Juliani R, Simon JE, Wu Q. Determination of flavonoids by LC/MS and anti-inflammatory activity in Moringa oleifera . J Funct Foods 2013; 5: 1892-1899
    CrossrefPubMedGoogle Scholar
  • 34 (ICH) [Anonymous]. International Conference on Harmonisation ICH harmonised tripartite guideline–validation of analytical procedures: text and methodology Q2 (R1). Geneva, Switzerland: International Conference on Harmonization; 2005: 11-12 Available at (Accessed Febuary 18, 2019): https://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf
    Google Scholar