Volatile Oil Composition of Nigella sativa L. Cultivars Collected from Iran

Document Type : Research Paper

Authors

1 Institute of Standard and Industrial Research of Iran, Tehran, Iran

2 Mycobacteriology Research Centre (MRC), National Research Institute of Tuberculosis and Lung Disease (NRITLD), Shahid Beheshti University of Medical Sciences, Tehran, Iran

3 Phytochemical Laboratory, Department of Chemistry, Faculty of Sciences, Azarbaijan Shahid Madani University, 53714-161, Tabriz, Iran

Abstract

Nigella sativa L., belonging to the family of Ranunculaceae, is grown for its seeds, which are used in food and medicinal industries. In this study, the volatile oil compositions of 16 cultivars of N. Sativa collected from different parts of Iran were evaluated, and then the chemotaxonomic study was done. The analysis of volatile oils was done using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), which identified 22 components. Major constituents of the collected cultivars were p-cymene (27.7-38.1%), thymoquinone (19.5-40.9%), thymohydroquinone (5.8-9.6%), α-thujene (5.1-7.2%), and trans-4-methoxythujane (3.4-4.8%). Then, Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA) were used to assess differences in volatile oil composition. PCA displayed that different groups of cultivars were characterized by high contents of specific compounds. The results of chemometric analysis displayed that PCA was approximately in agreement with HCA, and allowed classification of the studied cultivars into four groups including Group-A (Ns-4, Ns-5, and Ns-16); Group-B (Ns-1), Group-C (Ns-2, Ns-3, Ns-7, Ns-8, and Ns-12), and Group-D (Ns-6, Ns-9, Ns-10, Ns-11, Ns-13, Ns-14, and Ns-15). This is the first study on N. sativa in a vast geographical context in Iran to this extent, using different chemometric techniques. The results of this study can offer scientific data for germplasm of N. sativa in Iran and for breeding programs to improve developed cultivars.

Keywords

References

  1. Solati Z., Baharin B.S., Bagheri H. Antioxidant property, thymoquinone content and chemical characteristics of different extracts from Nigella sativa L. seeds. J Am Oil Chem Soc. 2014;91:295–300.
  2. Safaei Z., Azizi M., Maryam Y., Aroiee H., Davarynejad G. Effect of different irrigation intervals and anti-transpirant compounds on yield and yield components of Black Cumin (Nigella sativa). Inter J Adv Biol Biomed Res. 2014;2:326-335.
  3. Sarwar A., Latif Z. GC-MS characterisation and antibacterial activity evaluation of Nigella sativa oil against diverse strains of Salmonella. Nat Prod Res. 2015;29:447-451.
  4. Mehta BK., Pandit V., Gupta M. New principles from seeds of Nigella sativa. Nat Prod Res. 2009;23:138-148.
  5. Majdalawieh AF, Fayyad MW. Immunomodulatory and anti-inflammatory action of Nigella sativa and thymoquinone: A comprehensive review. Int J Immunopharmacol. 2015;28:295-304.
  6. Liu X., Aisa H.A., Xin X. A new fatty acid ester from Nigella sativa var. hispidula Boiss showing potent anti-protein tyrosine phosphatase 1B activity. Nat Prod Res. 2017;31:1-5.
  7. Ghanavi Z., Velayati A.A., Farnia P., Naji A.M., Kalatehjari S. Extraction and purification of anticancer thymoquinone from seeds of Nigella sativa by preparative High-performance Liquid Chromatography. J Med Plant By-prod. 2020;9(Special):73-79.
  8. Riyaz A., Nazir S., Khushtar M., Mishra A., Jahan Y., Ahmad A. Effect of Nigella sativa L. seed extract on cisplatin-induced delay in gastric emptying in Sprague-Dawley rats. Nat Prod Res. 2017;31:588-592.
  9. Al-Bukhari. Division (71) on medicine. In: Sahi Al-Bukhari (Ed.), The Collection of Authentic Sayings of Prophet Mohammad (peace be upon him). Turkey, Hilal Yayinlari, Ankara. 1976.
  10. Ali B.H., Blunden G. Pharmacological and toxicological properties of Nigella sativa. Phytother Res. 2003;17:299–305.
  11. Islam M.H., Ahmad I.Z., Salman M.T. Antibacterial activity of Nigella sativa oil seed in various germination phases on clinical bacterial strains isolated from human patients. E3. J Biotech Pharma Res. 2013;4:8–13.
  12. Rahmani A.H., Alzohairy MA, Khan M.A., Aly S.M. Therapeutic implications of black seed and its constituent thymoquinone in the prevention of cancer through inactivation and activation of molecular pathways. Evid Based Complement Alternat Med. 2014;2014:724658.
  13. Forouzanfar F., Fazly Bazzaz B.S., Hosseinzadeh H. Black cumin (Nigella sativa) and its constituent (thymoquinone): a review on antimicrobial effects. Iran J Basic Med Sci. 2014;17(12):929–938.
  14. Benkaci-Ali F., Baaliouamer A., Meklati B.Y., Chemat F. Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation. Flavour Fragr J. 2007;22:148-153.
  15. Burits M., Bucar F. Antioxidant activity of Nigella sativa essential oil. Phytother Res. 2000;14(5):323–328.
  16. Moretti A, D’Antuono FL, Elementi S. Essential oils of Nigella sativa L. and Nigella damascena L. Seed. J Essent Oil Res. 2004;16:182-183.
  17. Celiktas O.Y., Kocabas E.E.H., Bedir E., Sukan F.V., Ozek T., Baser KH.C. Antimicrobial activities of methanol extracts and essential oils of Rosmarinus officinalis, depending on location and seasonal variations. Food Chem. 2007;100:553-559.
  18. Sefidkon F., Sadeghzadeh L., Teimouri M., Asgari F., Ahmadi S. Antimicrobial effects of the essential oils of two Satureja species (S. Khuzistanica Jamzad and S. bachtiarica Bunge) in two harvesting time. Iran J Med Aroma Plant. 2007;23:174-182.
  19. Ghahramanloo KH., Kamalidehghan B., Akbari Javar H., Teguh Widodo R., Majidzadeh K., Noordin M.I. Comparative analysis of essential oil composition of Iranian and Indian Nigella sativa L. extracted using supercritical fluid extraction and solvent extraction. Drug Design Develop Therap. 2017;11:2221-2226.
  20. Rieger G., Müller M., Guttenberger H., Bucar F. Influence of altitudinal variation on the content of phenolic compounds in wild populations of Calluna vulgaris, Sambucus nigra, and Vaccinium myrtillus. J Agric Food Chem. 2008;56:9080-9086.
  21. Lu D., Zhang J., Yang Z., et al. Quantitative analysis of Cistanches Herba using high-performance liquid chromatography coupled with diode array detection and high‐resolution mass spectrometry combined with chemometric methods. J Sep Sci. 2013;36:1945-1952.
  22. Ebadi-Nahari M., Farnia P., Nikzat S., Mollaei S. A chemotaxonomic evaluation of some Scabiosa L. species in Iran. Biochem System Ecol. 2018;81:33-36.
  23. Lei H., Wang Y., Liang W., et al. Composition and variability of essential oils of Platycladus orientalis growing in China. Biochem Syst Ecol. 2010;38:1000–1006.
  24. Sampaio B.L., Edrada-Ebel R., Costa F.B. Effect of the environment on the secondary metabolic profile of Tithonia diversifolia: a model for environmental metabolomics of plants. Sci Rep. 2016;6:1-11.
  25. Santos D.L., Ferreira H.D., Borges L.L., et al. Chemical composition of essential oils of leaves flowers and fruits of Hortia oreadica. Rev Bras Farmacogn. 2015;26:23–28.
  26. Botnick I., Xue W., Bar E., et al. Distribution of primary and specialized metabolites in Nigella sativa seeds, a spice with vast traditional and historical uses. Molecules. 2012;17:10159-10177.
  27. Adams R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Corporation, Carol Stream, IL. 2007.
  28. NIST Chemistry Web Book. Data from NIST Standard Reference Database p. 69, 2011.
  29. Bajalan I., Rouzbahani R., Ghasemi Pirbalouti A., Maggi F. Quali-quantitative variation of essential oil from Iranian rosemary (Rosmarinus officinalis L.) accessions according to environmental factors. J Essen Oil Res. 2018;30(1):16-24.
  30. Morshedloo MR, Ebadi A, Maggi F, Fattahi R, Yazdani D, Jafari M. Chemical characterization of the essential oil compositions from Iranian populations of Hypericum perforatum L. Ind Crop Prod. 2015;76:565-573.
  31. Morshedloo M.R., Maggi F, Neko H.T., Aghdam MS. Sumac (Rhus coriaria L.) fruit: Essential oil variability in Iranian populations. Ind Crop Prod. 2018;111:1-7.
  32. Al-Saleh I.A., Billedo G., El-Doush II. Levels of selenium, dl-α-tocopherol, dl-γ-tocopherol, all-trans-retinol, thymoquinone and thymol in different brands of Nigella sativa seeds. J Food Compost Anal. 2006;19:167-175.
  33. Runyoro D., Ngassapa O., Vagionas K., Aligiannis N., Graikou K., Chinou I. Chemical composition and antimicrobial activity of the essential oils of four Ocimum species growing in Tanzania. Food Chem. 2010;119:311–316.
  34. Balahbib A., El Omari N., Hachlafi N.E., et al. Health beneficial and pharmacological properties of p-cymene. Food Chem Toxicol. 2021;153:112259.
  35. Mahmoudvand H., Sepahvand A., Jahanbakhsh S., Ezatpour B., Ayatollahi Mousavi SA. Evaluation of antifungal activities of the essential oil and various extracts of Nigella sativa and its main component, thymoquinone against pathogenic dermatophyte strains. J Mycol Med. 2014;24:e155-161.
  36. Chen F., Tholl D., Bohlmann J., Pichersky E. The family of terpene synthases in plants: A mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J. 2011;66:212–229.
  37. Dudareva N., Klempien A., Muhlemann J.K., Kaplan I. Biosynthesis, function and metabolic engineering of plant volatile organic compounds. New Phytol. 2013;198:16–32.
  38. Porter J.W., Spurgeon S.L. Biosynthesis of isoprenoid compounds, Wiley Interscience, pp. 243-244, 1981.
  39. Miceli A., Negro C., Tommasi L. Essential oil variabilyty in Thymbra capitata (L.) Cav. growing wild in Southern Apulia (Italy). Biochem System Ecol. 2006;34:528-535.
  40. Farkhondeh T., Samarghandian S, Borji A. An overview on cardioprotective and anti-diabetic effects of thymoquinone. Asian Pac J Trop Med. 2017;10:849–854.
  41. Khazdair M.R. The protective effects of Nigella sativa and its constituents on induced neurotoxicity. J Toxicol. 2015;2015:841823.
  42. Khan M.A., Tania M., Fu S., Fu J. Thymoquinone, as an anticancer molecule: from basic research to clinical investigation. Oncotarget. 2017;8:51907-51919.
Journal of Medicinal plants and By-Products
Volume 12, Issue 4
December 2023
Pages 375-386

Files

Share

How to cite

Statistics