Essential Oil Content and Composition of Nepeta kotschyi Boiss. (Lamiaceae) from Iran during Different Phenological Stages

Document Type : Research Paper

Authors

1 Department of Biology, Faculty of Science, Urmia University, Iran

2 Department of Medicinal Plants, Higher Education Center Shahid Bakeri Miyandoab, Urmia University, Iran

Abstract

Essential oils (EOs) because of being natural compounds and having antibacterial properties are important for health. The chemical composition of EOs might be affected by environmental conditions and plant growth and development stages. In this study, the essential oils and chemical compositions of aerial parts of Nepeta kotschyi Boiss. (Lamiaceae) were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS) at different plant phenological (in mid vegetative, 50% of flowering and fruiting) stages. The results showed that the EOs of Nepeta was affected by plant growth and development stages. So, both of content and their constituents were different in the plant phenological stages. The average percentage of EOs was ranged from 2.48 (in vegetative), 0.8 (in 50% of flowering), and 0.82 (in fruiting) stages. According to the results, 21 compounds with the range of 0.84-13.04 % in vegetative, 3 compounds with the range of 10.93-53.25% in 50% of flowering and 6 compounds with the range of 8.51-45.22% in fruiting stages were identified. The compounds 1,6,10-Nerolidol in vegetative (13.04%), Spathulenol in 50% of flowering (53.25%) and Caryophyllene oxide in fruiting stages (45.22%) had the highest value. Based on the results, the highest percentage of essential oils and compounds were related to the vegetative stage. The present study is the first report of the essential oil content of Nepeta during different plant phenological stages. The results of this study can be useful to understand the proper harvest time in Nepeta.

Keywords

References

1. Abdoli P, Moradkhani SH, Dastan D. Comparative analysis of Nepeta crispa essential oil composition in flowering and vegetative stages. AM J Phytomedi and Clinical Therapeutics (AJPCT). 2016;4:106-112.
2. Aberoomand-Azar P, Zare K, Saber-Tehrani M, Jafari-Kokhedan A, Vafaei A, Nekoei M, Larijani K. Chemical composition of the essential oil from Nepeta macrosiphon Boiss. growing wild in Iran by different extraction methods and studies on the quantitative relationship between the retention indices of essential oils and their molecular structures. Asian J Chem. 2013;25:4741-4746.
3. AbouLaila, M, Sivakumar T, Yokoyama N, Igarashi I. Inhibitory effect of terpene nerolidol on the growth of Babesia parasites. Parasitol. Int. 2010;59:278-282.
4. Ahmadian A, Tavassoli A, Amiri E. The interaction effect of water stress and manure on yield components, essential oil, and chemical compositions of cumin (Cuminum cyminum). Afr J Agr Res. 2011;6:2309-2315.
5. Amin GR. Popular medicinal plants of Iran. Ministry of Health Publisher, Iran. 1991
6. Arruda, DC, D-Alexandri FL, Katzin AM, and Uliana SR. Antileishmanial activity of the terpene nerolidol. Antimicrobe Agents Chemother. 2005;5:1679-1687.
7. Aruoma OI. Free radicals, oxidative stress, and antioxidants in human health and disease. J. Am. Oil Chem. Soc. 1998; 75:199-212.
8. Bourrel C, Perineau F, Michel G, Bessiere JM. Catnip (Nepeta cataria L.) essential oil: analysis of chemical constituents, bacteriostatic, and fungistatic properties. J Essent Oil Res. 1993;5:159-167.
9. Brehm-Stecher BF, Johnson EA. Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother. 2003; 10:3357-3360.
10. Burt S, Essential oils: their antibacterial properties and potential applications in food, a review. Int J Food Micro. 2004;94:223-253.
11. Caldefie-Chézet, F, Guerry M, Chalchat JC, Fusillier C, Vasson MP, Guillot J. Anti-inflammatory effects of Malaleuca alternifolia essential oil on human polymorph nuclear neutrophils and monocytes. Free Radic Res. 2004;38:805-811.
12. Cantino PD, Harley RM, Wagstaff SJ. Genera of Labiatae: status and classification. In: Harley, R. M., and T. Reynolds (eds.) Advances in Labiate science, Kew: Royal Botanic Gardens, UK. 1992;511-522.
13. Chalchat JC, Garry RP, Menut C, Lamaty G, Malhuret R, Chopineau J. Correlation between chemical composition and antimicrobial activity. VI. The activity of some African essential oils. J Essent Oil Res. 1997;9:67-75.
14. Chizzola R, Volatile compounds from some wild growing aromatic herbs of the Lamiaceae from southern France. Plant Biosys. 2006;140:206-210.
15. De-Almeida RN, De-Fátima Agra M, Souto Maior FN, and De-Sousa DP. Essential oils and their constituents: anticonvulsant activity. Molecules. 2011;16:2726-2742.
16. Esmaeili A, Rustaiyan A, Masoudi S, Nadji K. Composition of the essential oils of Mentha aquatica L. and Nepeta meyeri Benth. from Iran. J Essent Oil Res. 2006;18:263-265.
17. Evans WC. Trease and Evans’ Pharmacognosy. W.B. Saunders Company Ltd., London. 1996.
18. Franz C. Genetics, Volatile oil crops: their biology, biochemistry and production; In: Hay, R.K.M., and P.G. Waterman (eds.), Harlow: Long­man Scientific and Technical, England. 1993:63-96.
19. Ghahreman A, Colorful flora of Iran. Research Institute of Forests and Rangelands, Iran. 1979-1992.
20. Ghani A, Saharkhiz MJ, Hassanzadeh M, Msaada K. Changes in the essential oil content and chemical compositions of Echinophora platyloba DC. during three different growth and de­velopmental stages. J Essent Oil Bear. 2009;12:162-171.
21. Gilani AH, Shah AJ, Zubair A, Khalid S, Kiani J. Chemical composition and mechanisms underlying the spasmolytic and bronchodilatory properties of the essential oil of Nepeta cataria L. J of Ethnopharmacol. 2009;121:405-411.
22. Gkinis G, Tzakou O, Iliopoulou D, Roussis V. Chemical composition and biological activity of Nepeta parnassica oils and isolated Nepetalactones. Zeitschriftfür Naturforschung. 2003;58:681-686.
23. Gudaityt O, Venskutonis PR. Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment. Biochem Syst Ecol. 2007;35:82-592.
24. Hadi N, Sefidkon F, Shojaeiyan A, Jafari AA. Essential oil diversity of 21 populations from Iranian endemic species Nepeta kotschyi Boiss. Iranian Journal of Medicinal and Aromatic Plants. 2016;32:189-202.
25. Hadian J, Sonboli A, Nejad-Ebrahimi S, Mirjalili MH. Essential oil composition of Nepeta satureioides from Iran. Chem Nat Comp. 2006; 42:175-177.
26. Handjieva NV, Popon SS. Constituents of essential oils from Nepeta cataria L., N. grandiflora MB. and N. nuda L. J Essent. Oil Res. 1996;8:639-643.
27. Hassan T, Rather MA, Shawl AS. Chemical composition of the essential oils of Nepeta laevigata and Nepeta elliptica from India. Chem Nat Comp. 2011;47:456-458.
28. Heywood VH. The conservation of genetic and chemical diversity in medicinal and aromatic plants. In: Sener B (ed) Biodiversity: biomolecular aspects of biodiversity and innovative utilization, Kluwer Academic/Plenum Publishers, New York. 2002:13-22.
29. Hoet S, Stévigny C, Hérent MF, Quetin-Leclercq J. Antitrypanosomal compounds from the leaf essential oil of Strychnos spinosa. Planta Med. 2006;5:480-482.
30. Inoue Y, Hada T, Shiraishi A, Hirore K, Hamashima H, Kobayashi S. Biphasic effects of Geranylgeraniol, Terpenone and Phytol on the growth of Staphylococcus aureus. Antimicrobial agents and Chemother. 2005;49:1770-1774.
31. Jamzad Z, Grayer RJ, Kite GC, Simmonds MSJ, Ingrouille M. Leaf surface flavonoids in Iranian species of Nepeta L. (Lamiaceae) and some related genera. Biochem Syst Ecol. 2003;31:587-600.
32. Javidnia K, Miri R, Safavi F, Azarpira A, Shafiee A. Composition of the essential oil of Nepeta persica Boiss. from Iran. Flav Fragr J. 2002;17:20-22.
33. Jaimand K, Rezaee MB. Investigation on chemical constituents of essential oils from Achillea millefolium L. subsp. millefolium by distillation methods. Med and Aroma Plants Res of Iran. 2004;20:181-190.
34. Johann S, Oliveira FB, Siqueira EP, Cisalpino PS, Rosa CA, Alves TM, Zani CL, Cota BB. Activity of compounds isolated from Baccharis dracunculifolia D.C. (Asteraceae) against Paracoccidioide brasiliensis. Med Mycol. 2012;8:843-851.
35. Kalpoutzakis E, Aligiannis N, Mentis A, Mitaku S, Charvala C. Composition of the essential oil of two Nepeta species and in vitro evaluation of their activity against Helicobacter pylori. Planta Med. 2001;67:880-883.
36. Kamatou GPP, Viljoen AM. A review of the application and pharmacological properties of α-Bisabolol and α-Bisabolol-rich oils. J. Am. Oil Chem. Soc. 2010;87:1-7.
37. Klopell FC, Lemos M, Sousa JP, Comunello E, Maistro EL, Bastos JK, De-Andrade SF. An antiulcer constituent from the essential oil of Baccharis dracunculifolia DC (Asteraceae). Z Naturforsch. C. 2007;62:537-542.
38. Knobloch K, H Weigand, N Weis, HM Schwarm, H Vigenschow. Action of terpenoids on energy metabolism. In Progress in Essential Oil Research: 16th International Symposium on Essential Oils; Brunke EJ, Ed.; De Walter de Gruyter: Berlin, Germany. 1986:429-445.
39. Kobaisy M, Tellez MR, Dayan FE, Mamonov LK, Mukanova GS, Sitpaeva GT, Gemejieva NG. Composition and phytotoxic activity of Nepeta pannonica L. essential oil. J Essent Oil Res. 2005;17:704-707.
40. Koh KJ, Pearce AL, Marshman G, Finlay-Jones JJ, Hart PH. Tea tree oil reduces histamine-induced skin inflammation. Br. J. Dermatol. 2002;147:1212-1217.
41. Kökdil G, Tanker M, Kurucu S, Topcu G. Essential oil analysis of Nepeta cilicia Boiss. Flavour Frag J. 1997;12:99-101.
42. Koocheki A, Sabet-Teimouri M. Effects of fertilizer types and irrigation intervals of on quantity criteria of Lavender (Lavandula angustifolia), Rosemary (Rosemarinus officinalis) and Hyssop (Hyssopus officinalis). Iran J Field Crop Res. 2011;9:78-87.
43. Koudou J, Abena AA, Ngaissona P, Bessière JM. Chemical composition and pharmacological activity of essential oil of Canarium schweinfurthii. Fitoterapia. 2005;76:700-703.
44. Lapczynski A, Bhatia SP, Letizia CS, Api AM. Fragrance material review on nerolidol (isomer unspecified). Food Chem. Toxicol. 2008;46:247-250.
45. Lambert RJW, Skandamis PN, Coote P, Nychas GJE. A study of the minimum inhibitory concentration and mode of action of oregano essential oil, thymol and carvacrol. J Appl Microbiol. 2001;91:453-462.
46. Letchamo W, Korolyuk EA, Tkachev AV. Chemical screening of essential oil-bearing flora of Siberia IV. composition of the essential oil of Nepeta sibirica L. tops from Altai region. J Essent Oil Res. 2005;17:487-489.
47. Lopes NP, Kato MJ, Andrade EH, Maia JG, Yoshida M, Planchart AR, Katzin AM. Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb. by Waiãpi Amazon Indians. J. Ethnopharmacol. 1999;67:313-319.
48. McGinty D, Letizia CS, Api AM. Addendum to Fragrance material review on Nerolidol (isomer unspecified). Food Chem. Toxicol. 2010;48:43-45.
49. Miliauskas G, Venskutonis PR, Van-Beek TA. Screening of radical scavenging activity of some medicinal and aromatic plant ex­tracts. Food Chem. 2004;85:231-232.
50. Mohammadi S, Saharkhiz MJ. Changes in essential oil content and composition of catnip (Nepeta cataria L.) during different developmental stages.  J Essent Oil Bear Pl. 2011;14:396-400.
51. Mohammadi A, Malek F, Dehpour A, Nazari H. Chemical composition and antibacterial activity of the essential oils of some medicinal plants. Afr J Agric Res. 2013;8:3151-3158.
52. Mojab F, Nickavar B, Hooshdar H. Essential oil analysis of Nepeta crispa and N.menthoides from Iran. Iran J Pharm Sci. 2009;5:43-46.
53. Mozaffarian VA. dictionary of Iranian plant names: Latin-English-Persian. Farhang Moaser, Iran. 2006.
54. Msaada K, Hosni K, Taarit MB, Chahed T, Kchouk ME, Marzouk B. Changes on essential oil composition of coriander (Coriandrum sativum L.) fruits during three stages of maturity. Food Chem. 2007;102:1131-1134.
55. Negueruela AV, Rico MM, Benito PB, Perez-Alonso MJ. Composicion de los aceites esenciales de Nepeta nepetella subsp. aragonensis, Nepeta coerulea subsp. coerulea Nepeta cataria Giorn, Bot. Ital. 1998;122:295-302.
56. Nemeth E, Essential oil composition of species in the genus Achillea. J Essent Oil Res. 2005;17:501-512.
57. Nogueira-Neto JD, De-Almeida AA, Da-Silva Oliveira J, Dos-Santos PS, De-Sousa DP, De-Freitas RM. Antioxidant effects of nerolidol in mice hippocampus after open field test. Neurochem Res. 2013;38:1861-1870.
58. Nori-Shargh D, Baharvand B, Raftari S, Deyhimi F. The volatile constituents’ analysis of Nepeta kotschyi Boiss. from Iran. J Essent Oil Res. 2006;18:237-238.
59. Park MJ, Gwak KS, Yang I, Kim KW, Jeung EB, Chang JW, Choi IG. Effect of citral, eugenol, nerolidol and alpha-terpineol on the ultrastructural changes of Trichophyton mentagrophytes. Fitoterapia. 2009;80:290-296.
60. Penfold AR, Willis JL. The eucalypts, botany, cultivation, chemistry and utilization, Interscience Publishers, New York. 1961.
61. Rechinger KH, Nepeta. In: Rechinger KH (ed) Flora Iranica, No.150. Akademische Druck and Vertagsanstatt, Graz, Austria. 1982.
62. Ricke SC, Kundinger MM, Miller DR, Keeton JT. Alternatives to antibiotics: chemical and physical antimicrobial interventions and foodborne pathogen response. Poultry Sci. 2005;84:667-675.
63. Rustaiyan A, Nadji K. Composition of the essential oils of Nepeta ispahanica Boiss. and Nepeta binaludensis Jamzad from Iran. Flavour Frag J. 1999;14:35-37.
64. Rustaiyan A, Komeilizadeh H, Monfared A, Nadji K, Masoudi SH, Yari M. Volatile constituents of Nepeta denudate Benth. and N.Cephalotes Boiss. from Iran. J Essent Oil Res. 2000;11:459-461.
65. Rustaiyan A, Jamzad M, Masoudi S, Ameri N. Volatile constituents of Nepeta hellotropifolia Lam., Mentha mozaffarianii Jamzad and Ziziphora persica Bunge. three labiatae herbs growing wild in Iran. J Essent Oil Res. 2006;18:348-51.
66. Saeidnia S, Gohari AR, Hadjiakhoondi A. Trypanocidal activity of oil of the young leaves of Nepeta cataria L. obtained by solvent extraction. J Med Plants. 2008;7:54-57.
67. Saharkhiz MJ, Ghani A, Hassanzadeh-Khayyat M. Changes in es­sential oil content and composition of Clary sage (Salvia sclarea) aerial parts during different phenological stages. Med Aromat Plant Sci Biotechnol. 2009;3:90-93.
68. Sajjadi SE. Analysis of the essential oil of Nepeta sintenisii Bornm. from Iran. Daru. 2005;13:61-64.
69. Sajjadi SE, Khatamsaz M. Volatile constituent of Nepeta heliotropifolia Lam. J Essent Oil Res. 2001;13:204-205.
70. Sajjadi SE, Mehregan I. Chemical constituents of the essential oil of Nepeta daenensis Boiss. J Essent Oil Res. 2005;17:563-564.
71. Santoro GF, Das-Gracas Cardoso M, Guimaraes LG, Salgado AP, Menna-Barreto RF, Soares MJ. Effect of Oregano (Origanum vulgare L.) and Thyme (Thymus vulgaris L.) essential oils on Trypanosoma cruzi (Protozoa: Kinetoplastida) growth and ultrastructure. Parasitol. Res. 2007;100:783-790.
72. Sefidkon F, Shaabani A. Essential oil composition of Nepeta meyeri Benth. from Iran. Flavour Fragr J. 2004;19:236-238.
73. Sefidkon F, Abbasi K, Bakhshi-Khaniki G. Influence of drying and extraction methods on yield and chemical composition of the essential oil of Satureja hortensis. Food Chem. 2006;99:19-23.
74. Sefidkon F, Jamzad Z, Mirza M. Chemical composition of the essential oil of five Iranian Nepeta species (N. crispa, N. mahanensis, N.ispahanica, N. eremophila and N. rivularis). Flavour and Frag J. 2006;21:764-767.
75. Sermakkani M, Thangapandian V. GC-MS analysis of Cassia italicia leaf methanol extract. Asian Journal of Pharmaceutical and Clinical Research. 2012;5:90-94.
76. Sobral MV, Xavier AL, Lima TC, Sousa DP. Antitumor activity of monoterpenes found in essential oils. Hindawi Publishing Corporation. 2014:35.
77. Sonboli A, Salehi P, Yousefzadi M. Antimicrobial activity and chemical composition of the essential oil of Nepetacrispa Willd. from Iran. Zeitschriftfür Naturforschung. 2004;59:653-656.
78. Sonboli A, Salehi P, Allahyari L. Essential oil composition of Nepeta involucrate from Iran. Chem Nat Comp. 2005;41:683-685.
79. Thappa RK, Agarwal SG, Srivastava TN, Kapahi BK. Essential oils of four Himalayan Nepeta species. J Essent Oil Res. 2001;13:189-191.
80. Tucker AO, Tucker SS. Catnip and the catnip response. Econ Bot. 1988;42:214-231.
81. W-Dhifi L, Bellili S, Jazi S, Bahloul N, Mnif W. Essential oils’ chemical characterization and investigation of some biological activities: a critical review. Medicines. 2016;3:1-16.
82. Wagner H, Wolf P. New natural products and plant drugs with pharmacological, biological, and therapeutical activity. Springer Verlag, New York. 1977.
83. Zargari A. Medicinal Plants. Tehran University, Iran. 1996.
84. Zenasni L, Bouidida H, Hancali A, Boudhane A, Amzal H, Idrissi AI, Aouad RE, Bakri Y, Benjouad A. The essentials oils and antimicrobial activity of four Nepeta species from Morocco. J Med Plant Res. 2008;2:111-114.
85. Zengin H, Baysal AH. Antibacterial and antioxidant activity of essential oil terpenes against pathogenic and spoilage-forming bacteria and cell structure-activity relationships evaluated by SEM microscopy. Molecules. 2014;19:17773-17798.
86. Zomorodian K, Saharkhiz MJ, Rahimi MJ, Bandegi A, Shekarkhar G, Bandegani A, Pakshir K, Bazargani A. Chemical composition and antimicrobial activities of the essential oils from three ecotypes of Zataria multiflora. Pharma Magazine. 2011;7:5.
 
Journal of Medicinal plants and By-product
Volume 9, Issue 1
April 2020
Pages 123-131

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