Phytochemical Profiling of Methanolic Leaf Extracts of Vietnamese Murraya koenigii, a Highly Valued Traditional Medicine, using UHPLC‐Q‐TOF‐MS/MS

Document Type : Research Paper

Authors

1 Tra Vinh University, Tra Vinh City 700000, Vietnam

2 Faculty of Pharmacy, Nguyen Tat Thanh University, Ho Chi Minh City 700000, Vietnam

3 Institute of Applied Materials Science, Vietnam Academy of Science and Technology, Ho Chi Minh City 700000, Vietnam

4 Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow 117997, Russia

Abstract

Murraya koenigii (L.) Spreng (curry tree) is a tropical to subtropical tree originally from South Asia. The leaves of curry trees are an essential ingredient of Indian cuisine and are used as a flavoring in many dishes. The leaves are also widely used in Indian traditional medicine and possess the therapeutic potential due to the high content of biologically active compounds, including but not limited to flavonoids, steroids, alkaloids, phenolic compounds, etc. These compounds exhibit antioxidant, hypoglycemic, anticancer, antibacterial, and some other curative properties. It is well known that phytochemical composition is dependent on plant habitat. M. koenigii grows in Vietnam, where it is called “сà ri,” and is used in its cuisine. However, there is no data about the phytochemical profile of this plant from Vietnam. In this study, the extract of curry tree leaves was studied. For long-term methanol extraction, a maceration technique for 7 days was used. The extract was analyzed by UV-spectroscopy and ultra‐high‐performance liquid chromatography‐quadrupole time‐of‐fight tandem mass spectrometry (UHPLC‐Q‐TOF‐MS/MS). In the end, about two hundred matches with known substances including flavonoids, alkaloids, steroids, terpenoids, phenolic, and other compounds were identified in M. koenigii extract. In general, the phytochemical composition of Vietnamese M. koenigii resembles those of plants from other countries. However, several new compounds of unknown structure were found. Therefore, a furthermore detailed study of M. koenigii and other Murraya species native to Vietnam is needed.

Keywords

Main Subjects


  1. Gahlawat D.K., Dheeraj K., Jakhar S., Dahiya P. Murraya koenigii (L.) Spreng: an ethnobotanical, phytochemical and pharmacological review. Journal of Pharmacognosy and Phytochemistry. 2014;3:109-119.
  2. Ho P.H. Plants in Viet Nam (Vol. 2), Ho Chi Minh City: The Youth Publisher, 1999, p. 423.
  3. Nayak A., Mandal S., Banerji A., Banerji J. Review on chemistry and pharmacology of Murraya koenigii Spreng (Rutaceae). Journal of Chemical and Pharmaceutical Research. 2010;2:286-299.
  4. Sindhu R.K., Arora S. Evaluation of phenolic contents and antioxidant potential of Murraya koenigii (L) Spreng roots. Journal of applied pharmaceutical science. 2012;2:120-122. https://doi.org/10.7324/JAPS. 2012.21121
  5. Upadhye M.C., Deokate U.A., Pujari R.R. Antidiabetic effect of ethanolic extract of Murraya koenigii (Linn.) stem bark in alloxan induced diabetic rats. International Journal of Pharmacognosy. 2019;6:193-201. https://doi.org/10.13040/IJPSR.0975-8232.IJP. 6(6).193-01
  6. Abeysinghe D.T., Alwis D.D.D.H., Kumara K.A.H., Chandrika UG. Nutritive Importance and Therapeutics Uses of Three Different Varieties (Murraya koenigii, Micromelum minutum, and Clausena indica) of Curry Leaves: An Updated Review. Evidence-Based Complementary and Alternative Medicine. 2021;2021:5523252. https://doi.org /10.1155/2021/5523252.
  7. Fachraniah K.E., Novilasi D.T. Ekstraksi Antioksidan dari Daun Kari. Jurnal Reaksi. 2012;10:35.
  8. Ali A.I., Paul V., Chattree A., Prasad R., Paul A., Amiteye D. Evaluation of the use of different solvents for phytochemical constituents and antioxidants activity of the leaves of Murraya Koenigii (Linn.) Spreng. (rutaceae). Plant Archives. 2021;21:985-992. https://doi.org/10.51470/ plantarchives.2021.v21.no1.137
  9. Sanmugarajah V., Rajkumar G. A Review of Anti-hyperglycemic Effects of Curry Leaf Tree (Murraya koenigii). Borneo Journal of Pharmacy. 2022;5:104-114. https://doi.org/10.33084/bjop.v5i2.3300.
  10. Samanta S.K., Kandimalla R., Gogoi B., Dutta K.N., Choudhury P., Deb P.K., Devi R., Pal B.C., Talukdar N.C. Phytochemical portfolio and anticancer activity of Murraya koenigii and its primary active component, mahanine. Pharmacological Research. 2018;129:227-236. https://doi.org/10.1016/j.phrs.2017.11.024
  11. Gaidhane A.J., Chandewar A.B., Ambadkar B.B., Shoeb S. Phytochemical screening and antimicrobial investigation of Murraya koenigii. World Journal of Pharmaceutical Research. 2020;84:1206-1220. https://doi.org/10.20959/wjpr20203-16899
  12. Anshari M.K., Rusdi B. Studi literatur senyawa aktif antibakteri dari ekstrak daun salam koja (Murraya koenigii (Linn) Spreng). Jurnal Riset Farmasi. 2021;1:156-165. https://doi.org/10.29313/jrf.v1i2.571
  13. Sukma F.F., Sahara D., Ihsan F.N. Halimatussakdiah, Wahyuningsih P, Amna U. Skrining fitokimia ekstrak daun “temurui” (Murraya koenigii (L.) Spreng) Kota Langsa, Aceh. Jurnal Jeumpa. 2018;5:34-39.
  14. Chakraborty M. Mumunine - A New Carbazole Alkaloid from Murraya koenigii (Linn.) Spreng. Journal of Scientific Research. 2020;12:665-672. https://doi.org/10.3329/jsr.v12i4.45499
  15. Malode G.P., Parbat A.Y., Shaikh A.R., Panchale W.A., Manwar J.V., Bakal R.L. Phytochemistry, pharmacology and botanical aspects of Murraya koenigii in the search for molecules with bioactive potential - A review. GSC Advanced Research and Reviews. 2021;6:143-155. https://doi.org/10.30574/gscarr.2021.6.3.005
  16. Amna U., Halimatussakdiah H., Wahyuningsih P., Saidi N., Nasution R., Astryna S.Y. Phytochemical screening and in vitro Cytotoxic activity of Hexane extract of Temurui (Murraya koenigii (Linn.) Spreng) leaves against Human Cervical Cancer (HeLa) cell line. IOP Conference Series: Materials Science and Engineering. 2019;523:012018. https://doi.org/10.1088/1757-899X/523/1/012018
  17. Arunkumar J. Evaluation of anti-inflammatory activity of methanolic extract of murraya koenigii leaves in experimental animals. University Journal of Pre and Paraclinical Sciences. 2021;7:17340.
  18. Mathur A., Verma S.K., Singh S.K., Prasad G.B.K.S., Dua V.K. Investigation of the antimicrobial, antioxidant and antiinflammatory activity of compound isolated from Murraya koenigii. International Journal of Applied Biology and Pharmaceutical Technology. 2011;2:1-8.
  19. Nandan S., Singh S.K., Singh P., Bajpai V., Mishra A.K., Joshi T., Mahar R., Shukla S.K., Mishra D.K., Kanojiya S. Quantitative Analysis of Bioactive Carbazole Alkaloids in Murraya koenigii (L.) from Six Different Climatic Zones of India Using UPLC/MS/MS and Their Principal Component Analysis. Chemistry & Biodiversity. 2021;18:e2100557. https://doi.org/10.1002/cbdv.202100557.
  20. Singhal R., Verma S., Singh V. Phytochemical investigation of Nigella sativa seed extract by HPTLC, HPLC and GC-MS: a comparative geographical study. Natural Product Research. 2024;:1. https://doi.org/10.1080/14786419.2024.2348673.
  21. Murraya koenigii – Curry leaf tree [Internet]. Cuisine of Vietnam. [cited 3 November 2024]. Available from: https://cuisineofvietnam.com/murraya-koenigii-curry-leaf-tree/.
  22. Cà Ri: Vietnamese Curry in Saigon [Internet]. Vietnam Coracle. [cited 3 November 2024]. Available from: https://www.vietnamcoracle.com/ca-ri-vietnamese-curry-in-saigon/
  23. Allen D.R., McWhinney B.C. Quadrupole Time-of-Flight Mass Spectrometry: A Paradigm Shift in Toxicology Screening Applications. Clinical Biochemist Reviews. 2019;40:135-146. https://doi.org/ 10.33176/AACB-19-00023.
  24. Ngoc P.H., An T.C., Hiep N.T., Nhu T.P.H., Hung L.N., Trung N.Q., Minh B.Q., Trung P.V. UHPLC‐Q‐TOF‐MS/MS‐guided dereplication to study chemical constituents of Hedera nepalensis leaves in northern Vietnam. Journal of Analytical Science and Technology. 2023;14:14. https://doi.org/10.1186/s40543-023-00369-2
  25. Balakrishnan R., Vijayraja D., Jo S.H., Ganesan P., Su-Kim I., Choi D.K. Medicinal Profile, Phytochemistry, and Pharmacological Activities of Murraya koenigii and its Primary Bioactive Compounds. Antioxidants (Basel). 2020;9:101. https://doi.org/10.3390/antiox 9020101.
  26. Gutiérrez-García C. Study of secondary metabolites, microRNAs, and antidiabetic properties from the medicinal plant Murraya koenigii. Ph. D. [Thesis]. Queretaro, Mexico: Instituto Tecnológico y de Estudios Superiores de Monterrey; 2023.
  27. El-Shiekh, R. A., Elshimy, R., Mandour, A. A., Kassem, H. A., Khaleel, A. E., Alseekh, S., Fernie A.R., Salem, M. A. Murraya koenigii (L.) Sprengel seeds and pericarps in relation to their chemical profiles: new approach for multidrug resistant Acinetobacter baumannii ventilator-associated pneumonia. Applied Biological Chemistry. 2024;67:1-19.
  28. Franyoto Y.D, Nurrochmad A., Fakhrudin N. Murraya koenigii L. Spreng.: An updated review of chemical composition, pharmacological effects, and toxicity studies. Journal of Applied Pharmaceutical Science. 2024;14:11-27.
  29. Aroor MS, Dadwal V, Joshi R, Gupta M. Metabolomic approach for phytochemical assessment of Murraya koenigii fruits during different maturity stages. Heliyon. 2023;9:e18688. http://doi.org/10.1016/ j.heliyon.2023.e18688.
  30. Singh R., Farooq S.A., Devi S., Aggarwal R., Rangra N.K. Unveiling the pharmacological potential of Murraya koenigii against diabetic nephropathy. Indian Journal of Natural Products and Resources. 2024;15:87-103. http:/doi.org/10.56042/ijnpr.v15i1.5247.
  31. Yano M., Nakashima S., Kasa S., Nakamura S., Nishimura K., Oda Y., Takata K., Matsuda H. Accelerative effects of carbazole-type alkaloids from Murraya koenigii on neurite outgrowth and their derivative’s in vivo study for spatial memory. Journal of Natural Medicines. 2020;74:448-455. https://doi.org/10.1007/s11418-020- 01388-8
  32. Khurana A, Sikha M.S., Ramesh K., Venkatesh P., Godugu C. Modulation of cerulein-induced pancreatic inflammation by hydroalcoholic extract of curry leaf (Murraya koenigii). Phytotherapy Research. 2019;33:1510-1525. https://doi.org/10.1002/ptr.6344
  33. Hobani Y.H. Cytotoxicity of Mahanimbine from Curry Leaves in Human Breast Cancer Cells (MCF-7) via Mitochondrial Apoptosis and Anti-Angiogenesis. Molecules. 2022;27:971. https://doi.org/10.3390/molecules27030971.
  34. Syam S., Abdul A.B., Sukari M.A., Mohan S., Abdelwahab S.I., Wah T.S. The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest. Molecules. 2011;16:7155-7170. https://doi.org/10.3390/molecules16087155.
  35. Shen N., Wang T., Gan Q., Liu S., Wang L., Jin B. Plant flavonoids: Classification, distribution, biosynthesis, and antioxidant activity. Food Chemistry. 2022;383:132531. https://doi.org/10.1016/j.foodchem. 2022.132531.
  36. Ghasemzadeh A., Jaafar H.Z.E., Rahmat A., Devarajan T. Evaluation of bioactive compounds, pharmaceutical quality, and anticancer activity of curry leaf (Murraya koenigii L.). Evidence-Based Complementary and Alternative Medicine. 2014;:873803. https://doi.org/10.1155/2014/873803
  37. Thi Nguyen T.T., The Diep T., Hoang V., Mai Vo T.H., Duus F., Ngoc Le T. Investigation of Curry Leaf Essential Oils of Murraya koenigii Spreng. Growing in the South of Vietnam. Journal of Essential Oil Bearing Plants. 2012;15:1021-1029. https://doi.org/10.1080/0972060X .2012.10662607
  38. Teshima N., Yamada H., Ju-Ichi M., Uji T., Kinoshita T., Ito C. Coumarins from Murraya paniculata var. zollingeri Endemic to the Timor Islands. Natural Product Communications. 2015;10:309-312. https://doi.org/ 10.1177/1934578x1501000224.