CHEMICAL COMPOSITION OF THE ESSENTIAL OIL OF ZIZIPHORA PAMIROALAICA LAM. (LAMIACEAE) GROW-ING IN TAJIKISTAN
Abstract
Ziziphora pamiroalaica Lam. (Lamiaceae) is a medicinal plants used in Tajikistan for the treatment of the diseases of cardiovascular system and gastrointestinal tract. In the present study the composition of essential oil of herb Z. pamiroalaica growing in the Gorno-Badakhshan Autonomous Region was studied for the first time. The method of gas chromatography / mass-spectrometry allowed to identify thirty-four compounds including monoterpenes, aliphatic alcohols, ethers and phenols sesquiterpenes. The dominant components of the essential oil were pulegone (52,7–60,4%), thymol (7,5–11,1%), isomenthone (7,1–10,6%) and menthone (3,9–6,3%). The known information about the composition of essential oil of Z. pamiroalaica of Chinese origin showed the lower content of pulegone in the latter sample (45,9%) as well as a greater concentration and neomenthol and isomenthone. It is found that the height of the plant growth reflects on the quantitative ratio of individual components of the essential oil especially mono- and sesquiterpenes. The principal component analysis was used for the comparative study of data about the chemical composition of essential oils of ten species of Ziziphora genus. The principal component analysis was used to show that the chemical composition of essential oils Z. pamiroalaica close to that of Z. clinopodioides, As a result, it was found that the chemical composition of essential oil of Z. pamiroalaica similar to that of Z. clinopodioides but differs from it by less pulegone content.
Downloads
Metrics
References
Baser K.H.C., Kirimer N., Tumen G. Pulegone-rich essential oils of Turkey // J. Essent. Oil Res. 1998. Vol. 10. Pp. 1–8.
Dzhumaev Kh.K., Zenkevich I.G., Tkachenko K.G., Tsibul’skaya I.A. Essential oils of the inflorescences and leaves of Ziziphora brevicalyx // Chem. Nat. Comp. 1990. Vol. 26. Pp. 99–101.
Baser K.H.C., Sezik E., Tümen G. Composition of the essential oil of Ziziphora clinopodioides Lam. // J. Ess. Oil Res. 1991. Vol. 3. Pp. 237–239.
Belyaev N.F., Demeubaeva A.M. Chromatographic study of the composition of the essential oil of Ziziphora clinopodi-oides, a vicarious form of Origanum vulgare // Chem. Nat. Comp. 1999. Vol. 35. Pp. 52–54.
Королюк Е.А., Кёниг В., Ткачев А.В. Состав эфирного масла зизфоры пахучковидной (Ziziphora clinopodioides Lam.) из Алтайского края и Республики Алтай // Химия растительного сырья. 2002. №1. С. 49–52.
Behravan J., Ramezani M., Hassanzadeh M.K., Eskandari M., Kasaian J., Sabeti Z. Composition, antimycotic and anti-bacterial activity of Ziziphora clinopodioides Lam. essential oil from Iran // J. Ess. Oil Res. 2007. Vol. 10. Pp. 339–345.
Ozturk S., Ercisli S. Antibacterial activity and chemical constitutions of Ziziphora clinopodioides // Food Control. 2007. Vol. 18. Pp. 535–540.
Aghajani Z., Assadian F., Masoudi Sh., Chalabian F., Esmaeili A., Tabatabaei-Anaraki M., Rustaiyan A. Chemical composition and in vitro antibacterial activities of the oil of Ziziphora clinopodioides and Z. capitata subsp. capitata from Iran // Chem. Nat. Comp. 2008. Vol. 44. Pp. 387–389.
Sharopov F.S., Setzer W.N. Chemical diversity of Ziziphora clinopodioides: Composition of the essential oil of Z. clinopodioides from Tajikistan // Nat. Prod. Commun. 2011. Vol. 6. Pp. 695–698.
Ebrahimi P., Mirarab-Razi A., Biabani A. Comparative evaluation of the essential oil terpenoids in the stem and leaf of Ziziphora clinopodioides in the regions of Almeh and Sojough of Golestan Province, Iran // Acta Period. Technol. 2012. Vol. 43. Pp. 283–291.
Shahla S.N. Chemical composition and in vitro antibacterial activity of Ziziphora clinopodioides Lam. essential oil against some pathogenic bacteria // Afr. J. Microbiol. Res. 2012. Vol. 6. Pp. 1504–1508.
Zhou X., Yu Q., Gong H., Tian S. GC-MS analysis of Ziziphora clinopodioides essential oil from North Xinjiang, China // Nat. Prod. Commun. 2012. Vol. 7. Pp. 81–82.
Kilic O., Bagci E. Essential oils of three Ziziphora L. Taxa from Turkey and their chemotaxonomy // Asian J. Chem. 2013. Vol. 25. Pp. 7263–7266.
Masrournia M., Shams A. Elemental determination and essential oil composition of Ziziphora clinopodioides and con-sideration of its antibacterial effects // Asian J. Chem. 2013. Vol. 25. Pp. 6553–6556.
Ding W., Yang T., Liu F., Tian S. Effect of different growth stages of Ziziphora clinopodioides Lam. on its chemical composition // Pharmacogn. Mag. 2014. Vol. 10. Pp. S1–S5.
Kheirkhah M., Ghasemi V., Yazdi A.K., Rahban S. Chemical composition and insecticidal activity of essential oil from Ziziphora clinopodioides Lam. used against the Mediterranean flour moth, Ephestia kuehniella Zeller // J. Plant Protect. Res. 2015. Vol. 55. Pp. 260–265.
Khodaverdi-Samani H., Pirbalouti A.G., Shirmardi H.-A., Malekpoor F. Chemical composition of essential oils of Ziziphora clinopodioides Lam. (endemic Iranian herb) collected from different natural habitats // Ind. J. Trad. Knowl. 2015. Vol. 14. Pp. 57–62.
Shahbazi Y., Shavisi N., Mohebi E. Effects of Ziziphora clinopodioides essential oil and nisin, both separately and in combination, to extend shelf life and control Escherichia coli O157:H7 and Staphylococcus aureus in raw beef patty during refrigerated storage // J. Food Saf. 2016. Vol. 36. Pp. 227–236.
Ebrahimi S.N., Hadian J., Sonboli A. Chemical composition of the essential oil of Ziziphora capitata L. from Iran // J. Ess. Oil-Bear. Plants. 2009. Vol. 12. Pp. 678–682.
Sonboli A., Mirjalili M.H., Hadian J., Ebrahimi S.N., Yousefzadi M. Antibacterial activity and composition of the es-sential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran // Z. Naturforsch. 2006. Vol. 61c. Pp. 677–680.
Salehi P., Sonboli A., Eftekhar F., Nejad-Ebrahimi S., Yousefzadi M. Essential oil composition, antibacterial and anti-oxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (Boiss.) Rech. f. from Iran // Biol. Pharm. Bull. 2005. Vol. 28. Pp. 1892–1896.
Sonboli A., Atri M., Shafiei S. Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran // Chem. Biodiv. 2010. Vol. 7. Pp. 1784–1789.
Rabah B., Lograda T., Ramdani M., Chalard P., Feguiredo G. Chemical composition and antibacterial activity of essen-tial oil of Ziziphora hispanica L. // Glob. J. Res. Med. Plants Indigen. Med. 2013. Vol. 2. Pp. 73–80.
Goryaev M.I., Sharipova F.S., Mukhametgaliev A.G., Khazanovich R.L., Pulatova T.P. A study of the essential oil of Ziziphora pedicellata // Chem. Nat. Comp. 1970. Vol. 6. P. 127.
Dembitskii A.D., Bergaliev E.Sh., Kyazimov I.M. Chemical composition of the essential oils of Ziziphora growing un-der various ecological conditions // Chem. Nat. Comp. 1994. Vol. 30. Pp. 673–675.
Ozturk S., Ercisli S. The chemical composition of essential oil and in vitro antibacterial activities of essential oil and methanol extract of Ziziphora persica Bunge // J. Ethnopharmacol. 2006. Vol. 106. Pp. 372–376.
Meral G.E., Konyalioglu S., Ozturk B. Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides // Fitoterapia. 2002. Vol. 73. Pp. 716–718.
Karimi I., Hayatgheybi H., Motamedi S., Afzali D., Aghdam A.H. Chemical composition and hypolipidemic effects of an aromatic water of Ziziphora tenuior L. in cholesterol-fed rabbits // J. Appl. Biol. Sci. 2013. Vol. 7. Pp. 61–67.
Pirbalouti A.G., Amirkhosravi A., Bordbar F., Hamedi B. Diversity in the chemical composition of essential oils of Ziziphora tenuior as a potential source of pulegone // Chemija. 2013. Vol. 24. Pp. 234–239.
Delnavazi M.-R., Baba-ali F., Soufiabadi S., Tavakoli S., Yassa N. Essential oil composition, antioxidant activity and total phenolic content of some Lamiaceae taxa growing in Northwest of Iran // Pharm. Sci. 2014. Vol. 20. Pp. 22–28.
Gholivand M.B., Piryaei M., Maassoumi S.M. Antioxidant activity of Ziziphora tenuoir methanolic extracts and com-parison of the essential oil in two stages of growth // Chin. J. Nat. Med. 2014. Vol. 12. Pp. 505–511.
Pakniyat E., Mousavi M. Improvement of GC-MS analysis of shahrbabak Ziziphora tenuior essential oil by using mul-tivariate curve resolution approaches // J. Chin. Chem. Soc. 2014. Vol. 61. Pp. 649–658.
Celik C., Tutar U., Karaman I., Hepokur C., Atas M. Evaluation of the antibiofilm and antimicrobial properties of Ziziphora tenuior L. essential oil against multidrug-resistant Acinetobacter baumannii // Int. J. Pharmacol. 2015. Vol. 12. Pp. 28–35.
Ganjali A., Harati M.P., Kaykhaii M. Antimicrobial effect of essential oil of Ziziphora tenuior on water by heterotrophic plate counts method in Kerman (Southeast of Iran) // Int. J. Chem. Eng. Applicat. 2016. Vol. 7. Pp. 120–123.
Akobirshoeva A. Medical plants of Rushan district, GBAO, Tajikistan. LAP Lambert Academic Publishing: Saarbuck-en, 2012. 96 p.
Xing S., Zhang P., Ji Q., Jia H., Wang X. Essential oil and antioxidant activity of two Ziziphora species in Xinjiang // Food Sci. 2010. Vol. 31. Pp. 154–159.
Olennikov D.N., Akobirshoeva A.A. Flavonoids and phenylpropanoids of Nepeta glutinosa and Ziziphora pamiroalai-ca // Chem. Nat. Comp. 2016. Vol. 52. Pp. 909–912.
Turner G.W., Croteau R. Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase // Plant Physiol. 2004. Vol. 136. Pp. 4215–4227.
Lima T.C., Mota M.M., Barbosa-Filho J.M., Dos Santos M.R.V., De Sousa D.P. Structural relationships and vaso-relaxant activity of monoterpenes // DARU Journal of Pharmaceutical Sciences. 2012. Vol. 20. Art. No 23. URL: http://darujps.biomedcentral.com/articles/10.1186/2008-2231-20-23
Da Silveira N.S., De Oliveira-Silva G.L., De Fereitas Lamanes B., Da Silva Prado L.C., Bispo-da-Silva L.B. The aver-sive, anxiolytic-like, and verapamil-sensitive psychostimulant effects of pulegone // Biol. Pharm. Bull. 2014. Vol. 37. Pp. 771–778.
Yao Q.-S., Chiou G.C.Y. Inhibition of crystallins-induced inflammation in rabbit eyes with five phytogenic compounds // Acta Pharm. Sin. 1993. Vol. 14. Pp. 13–17.
Ortiz de Urbina A.V., Martin M.L., Montero M.J., Carron R., Sevilla M.A., San Roman L. Antihistaminic activity of pulegone on the guinea-pig ileum // J. Pharm. Pharmacol. 1990. Vol. 42. Pp. 295–296.
Arruda T.A., Antunes R.M.P., Catão R.M.R., Lima E.O., Sousa D.P., Nunes X.P., Pereira M.S.V., Barbosa-Filho J.M., da Cunha E.V.L. Preliminary study of the antimicrobial activity of Mentha villosa Hudson essential oil, rotundi-folone and its analogues // Braz. J. Pharmacogn. 2006. Vol. 16. Pp. 307–311.
This work is licensed under a Creative Commons Attribution 4.0 International License.
The authors, which are published in this journal, agree to the following conditions:
1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .
2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.
3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.