ФИТОХИМИЧЕСКАЯ ХАРАКТЕРИСТИКА И ОЦЕНКА ИЗМЕНЧИВОСТИ КОМПОНЕНТНОГО СОСТАВА ЭФИРНОГО МАСЛА НЕКОТОРЫХ ВИДОВ РОДА JUNIPERUS L.

В статье представлены результаты изучения содержания эфирного масла в зеленой массе двух автохтонных и трех интродуцированных видов рода Juniperus L., произрастающих в условиях Южного берега Крыма. Массовая доля эфирного масла в свежесобранном сырье исследуемых видов колеблется от 0,03% до 0,81%. Общими чертамы эфирного масла изучаемых видов было наличие в составе монотерпеновых углеводородов: α-пинена, β-мирцена, α-терпинена, p-цимена, γ-терпинена, α-терпинолена, линалоола, терпинен-4-ола, и сесквитерпенов: α-мууролена, δ-кадинена. Мажорными компонентами эфирного масла Juniperus excelsa M. Bieb. были α-пинен (46,47%) и кедрол (19,48%), Juniperus deltoides R.P.Adams.: α-пинен (26,52%) и D-лимонен (12,54%), Juniperus chinensis L. – борнилацетат (41,35%), Juniperus virginiana L.: сафрол (29,32%), D-лимонен (20,18%), элемол (12,7%) и прегеиджерен (10,49%), Juniperus phoenicea Hochst. ex Endl.: α-пинен (28%), β-фелландрен (19,63%) и α-терпинилацетат (13,8%). Изучение хемотипического разнообразия видов рода Juniperus свидетельствует о том, что в большинстве случаев существуют определенная закономерность накопления отдельных компонентов в эфирном масле, что имеет важнейшее значение, как для практического использования сырья можжевельников с целью получения биологически активных веществ, так и для возможностей использования имеющихся данных для хемосистематики рода.

1. Князева С.Г. Изменчивость морфологических признаков сибирских видов можжевельника // Лесоведение. – 2007. – № 1. – С. 65-69.

2. Плугатарь Ю.В. Корсакова С.П., Ильницкий О.А. Экологический мониторинг Южного берега Крыма. – Симферополь: ИТ «АРИАЛ», 2015. – 164 с.

3. Ткачев А.В. Исследование летучих веществ растений. – Новосибирск: Издательско-полиграфическое предприятие «Офсет», 2008. – 969 с.

4. Шевчук О.М., Исиков В.П., Логвиненко Л.А. Методологические и методические аспекты интродукции и селекции ароматических и лекарственных растений. – Симферополь: ИТ «АРИАЛ», 2022. – 140 с.

5. Шутова А.Г., Спиридович Е.В., Гаранович И.М., Сенькевич Г.Г., Неверо А.С., Ризевский С.В., Курченко В.П. Состав эфирных масел представителей рода Juniperus L., интродуцированных в Центральном ботаническом саду НАН Беларуси // Труды БГУ. Серия Физиологические, биохимические и молекулярные основы функционирования биосистем. – 2009. – Т.4, №1. – С. 115-130.

6. Adams R.P. Identification of essential oil compounds by gas chromatography/quadrupole mass spectroscopy. – USA, 2007. – 804 p.

7. Adams R.P. Systematic of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting // Biochemical Systematics and Ecology. – 1999. – Vol. 27. – P. 709-725.

8. Adams R.P. The chemical composition of leaf oils of Juniperus excelsa M.Bieb. // Journal of Essential Oil Research. – 1990. – Vol. 2. – P. 45-48. DOI: 10.1080/10412905.1990.9697815.

9. Adams R.P. The Junipers of the world: The genus Juniperus. 4sd ed. – Victoria: BC, 2014. – 422 p.

10. Adams R.P., Matarci T. Taxonomy of Juniperus deltoids forma Yaltirikiana in Turkey: leaf terpenoids and SNPS from nrDNA and petN // Phytologia. – 2011. – Vol. 93. – 293 p.

11. Adams R.P., Morris J.A., Pandey R.N, Schwarzbach A.E. Cryptic speciation between Juniperus deltoids and Juniperus oxycedrus (Cupressaceae) in the Mediterranean // Biochemical Systematics and Ecology. – 2005. – Vol. 33. – 771 p.

12. Adams R.P., Tashev A.N. Geographic variation in leaf oils of Juniperus deltoides from Bulgaria, Greece, Italy and Turkey // Phytologia. – 2012. – Vol. 94(3). – P. 310-318.

13. Adams R.P. The leaf essential oils and chemotaxonomy of Juniperus sect. Juniperus // Biochemical Systematics and Ecology. – 1998. – Vol. 26. – P. 637-645.

14. Angioni A., Barra A., Russo M.T., Coroneo V., Dessí S., Cabras P. Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity // Journal of Agricultural and Food Chemistry. – 2003. – Vol. 51. – P. 3073-3078.

15. Aouadi M., Kamel M., Essia S.,Wissem A.W., Mohamed S.A., Hafidh A. Antioxidant, anthelmintic and antibacterial activities of red juniper (Juniperus phoenicea L.) essential oil // Journal of Essential Oil Research. – 2021. – Vol. 34. – P. 1-10. DOI:10.1080/10412905.2021.1941338.

16. Bhavaniramya S., Vishnupriya S., Al-Aboody M.S., Vijayakumar R., Baskaran D. Role of essential oils in food safety: Antimicrobial and antioxidant applications // Grain & Oil Science and Technology. – 2019. – Vol. 2. – P. 49-55.

17. Bouyahyaoui A., Bahri F., Romane A., Höferl M., Wanner J., Schmidt E., Jirovetz L. Antimicrobial activity and chemical analysis of the essential oil of Algerian Juniperus phoenicea // Natural Product Communications. – 2016. – Vol. 11. – P. 519-522.

18. Chavchanidze V.Y., Kharebava L.G. Studies on the essential oils of juniper // Subtropical Cultures. – 1989. – Vol. 4. – P. 131-143.

19. El-Sawi S.A., Motawae H.M., Ali A.M. Chemical composition, cytotoxic activity and antimicrobial activity of essential oils of leaves and berries of Juniperus phoenicea L. grown in Egypt // African Journal of Traditional, Complementary, and Alternative Medicines. – 2007. – Vol. 4. – P. 417-426.

20. Farhat P., Hidalgo O., Robert T., Siljak-Yakovlev S., Leitch I.J., Adams R.P., Bou Dagher-Kharrat M. Polyploidy in the Conifer Genus Juniperus: An Unexpectedly High Rate // Frontiers in Plant Science. – 2019. – Vol. 10. – P. 676. DOI: 10.3389/fpls.2019.00676.

21. Gawde A.J., Cantrell C.L., Zheljazkov V.D. Dual extraction of essential oil and podophyllotoxin from Juniperus virginiana // Industrial Crops and Products. – 2009. – Vol. 30. – P. 276-280.

22. Hădărugă N., Branic A., Hădărugă D., Lukinich-Gruia A., Pleşa C., Costescu C., Ardelean A., Lupea A. Comparative Study of Juniperus communis and Juniperus virginiana Essential Oils: TLC and GC Analysis // JPC – Journal of Planar Chromatography. – 2011. – Vol. 24. – P. 130-135. DOI: 10.1556/JPC.24.2011.2.9.

23. Hojjati F., Sereshti H., Hojjati M. Leaf essential oils and their application in systematics of Juniperus excelsa complex in Iran // Biochemical Systematics and Ecology. – 2019. – Vol. 84. – P. 29-34.

24. Huyan T., Li Q., Wang Y.L., Li J., Zhang J.Y., Liu Y.X., Shahid M.R., Yang H., Li H.Q. Anti-tumor effect of hot aqueous extracts from Sonchus oleraceus (L.) L. and Juniperus sabina L. – Two traditional medicinal plants in China // Journal of Ethnopharmacology. – 2016. – Vol. 185. – P. 289-299.

25. Kakar H., Sajjad A., Rizwan S., Mahmood K., Mehmood Z., Azam M., Hafeez I., Sarangzai A.M., Nadhman A., Yasinzaia M. Chemical composition, antimicrobial and antileishmanial activity of essential oil of Juniperus excelsa M.Bieb. from Ziarat, Balochistan // Pure and Applied Biology. – 2017. – Vol. 6. – P. 786-796.

26. Keskes H., Mnafgui K., Hamden K., Damak M., El Feki A., Allouche N. In vitro antidiabetic, anti-obesity and antioxidant proprieties of Juniperus phoenicea L. leaves from Tunisia // Asian Pacific Journal of Tropical Biomedicine. – 2014. – Vol. 4. – P. 649-655.

27. Khamis Al-Dhafri S., Chai L.C. Chemical and Antimicrobial Analyses of Juniperus chinensis and Juniperus seravschanica Essential Oils and Comparison with Their Methanolic Crude Extracts // International Journal of Analytical Chemistry. – 2021. – 8 p.

28. Khoury M., Beyrouthy M., Ouaini N., Iriti M., Eparvier V., Stien D. Chemical composition and antimicrobial activity of the essential oil of Juniperus excelsa M.Bieb. growing wild in Lebanon // Chemistry & Biodiversity. – 2014. – Vol. 11(5). – P. 825-30. DOI: 10.1002/cbdv.201300354.

29. Kim M.G., Lee N.H., Kim J.M., Lee S.G., Lee H.S. Chemical Composition of Essential Oils Extracted from Five Juniperus chinensis Varieties in Korea // Journal of Essential Oil Bearing Plants. – 2015. – Vol. 18(4). – P. 852-856.

30. Lesjak M., Beara I., Orčić D., Anačkov G., Knežević P., Mrkonjić Z., Mimica–Dukić N. Bioactivity and chemical profiling of the Juniperus excelsa, which support its usage as a food preservative and nutraceutical // International Journal of Food Properties. – 2017. – Vol. 20 (Suppl. 2). – P. 1652-1663.

31. Moein M.R., Ghasemi Y., Moein S., Nejati M. Analysis of antimicrobial, antifungal and antioxidant activities of Juniperus excelsa M. B subsp. polycarpos (K. Koch) Takhtajan essential oil // Pharmacognosy Research. – 2010. – Vol. 2. – P. 128.

32. Öz M., Saruhan E. Chemical Content and Antimicrobial Activities of Essential Oils Obtained from Plant Parts of Juniperus excelsa M. Bieb. // Drvna industrija. – 2023. – Vol. 74. – P. 347-357. DOI:10.5552/drvind.2023.0082.

33. Pavela R., Maggi F., Mazzara E., Torresi J., Cianfaglione K., Benelli G., Canale A. Prolonged sublethal effects of essential oils from non-wood parts of nine conifers on key insect pests and vectors // Industrial Crops and Products. – 2021. – Vol. 168. – P. 113590.

34. Radoukova T., Zheljazkov V., Semerdjieva I., Dincheva I., Stoyanova A., Kaˇcániová M., Markovi´c T., Radanovi´c D., Astatkie T., Salamon I. Differences in essential oil yield, composition, and bioactivity of three Juniper species from Eastern Europe // Industrial Crops and Products. – 2018. – Vol. 124. – P. 643-652.

35. Raina V., Srivastava S., Syamsundar K.S. Essential oil composition of Juniperus chinensis from the plains of northern India // Flavour and Fragrance Journal. – 2005. – Vol. 20. – P. 57-59. DOI:10.1002/ffj.1366.

36. Rajčević N., Janaćković P., Bojović S., Tešević V., Marin P.D. Variability of the needle essential oils of Juniperus deltoides R.P.ADAMS from different populations in Serbia and Croatia // Chemistry & Biodiversity. – 2013. – Vol. 10(1). – P. 144-156. DOI: 10.1002/cbdv.201200190.

37. Rajčević N., Janaćković P., Dodoš T., Tešević V., Marin P.D. Essential-oil variability of Juniperus deltoides R.P. Adams along the east Adriatic coast - how many chemotypes are there? // Chemistry & Biodiversity. – 2015. – Vol. 12(1). – P. 82-95. Doi: 10.1002/cbdv.201400122. PMID: 25641838.

38. Raut J.S., Karuppayil S.M. A status review on the medicinal properties of essential oils // Industrial Crops and Products. – 2014. – Vol. 62. – P. 250-264.

39. Sahin Y.A., Eser F., Yaglioglu M.S., Demirtas I. The antiproliferative and antioxidant activities of the essential oils of Juniperus species from Turkey // Flavour and Fragrance Journal. – 2020. – Vol. 35. – P. 511-523.

40. Samara Y.K., Beniaich G., El Abdali Y., Kaouia S., Flouchi R., Moubchir T., Allali A., Khadmaoui A. Phytochemical Composition, Antibacterial and Antifungal Activities of Essential Oil of Juniperus phoenicea from Fez-Meknes Region, North Central Morocco // Tropical Journal of Natural Product Research. – 2023. – Vol. 7(12). – P. 5633-5639.

41. Seca A., Silva A. The chemical composition of the Juniperus genus (1970–2004). In Recent Progress in Medicinal Plants, vol. 16. Phytomedicines; Govil, J.N., Singh, V.K., Bhardwaj, R., Eds. – Texas, USA: Studium Press LLC: Houston, 2006. – P. 401-522.

42. Sela F., Karapandzova M., Stefkov G., Cvetkovikj I., Kulevanova S. Chemical composition and antimicrobial activity of essential oils of Juniperus excelsa Bieb. (Cupressaceae) grown in R. Macedonia // Pharmacognosy Research. – 2015. – Vol. 7(1). – P. 74-80. DOI: 10.4103/0974-8490.147212.

43. Semerdjieva I., Shiwakoti S., Cantrell C., Zheljazkov D.V., Astatkie T., Schlegel V., Radoukova T. Hydrodistillation Extraction Kinetics Regression Models for Essential Oil Yield and Composition in Juniperus virginiana, J. excelsa, and J. sabina // Molecules. – 2019. – Vol. 24. – P. 986.

44. Semerdjieva I., Zheljazkov V.D., Radoukova T., Dincheva I., Piperkova N., Maneva V., Astatkie T., Kaˇcániová M. Biological Activity of Essential Oils of Four Juniper Species and Their Potential as Biopesticides // Molecules. – 2021. – Vol. 26. – P. 6358.

45. Sowndhararajan K., Seo M., Kim S. Comparative analysis of the composition of essential oils from the needles, twigs and berries of Juniperus chinensis L. in Korea // Journal of Applied Pharmaceutical Science. – 2016. – Vol. 6 (08). – P. 122-126.

46. Topçu G., Gören A.C., Bilsel G., Bilsel M., Çakmak O., Schilling J., Kingston D.G. Cytotoxic activity and essential oil composition of leaves and berries of Juniperus excelsa // Pharmaceutical Biology. – 2005. – Vol. 43. – P. 125-128.

47. Unlu M.,Vardar-Unlu G.,Vural N., Donme, E., Çakmak O. Composition and antimicrobial activity of Juniperus excelsa essential oil // Chemistry of Natural Compounds. – 2008. – Vol. 44. – P. 129-131. DOI:10.1007/s10600-008-0040-x.

48. Yesenofski J. Juniper Oil Distillation and Marketing Project Western Juniper Commercialization Program Final Report, Ver. 2. The Confederated Tribes of the Warm Springs Reservation of Oregon, Business & Economic Development Branch. 1996.

49. Zhang K., Yao L. The anxiolytic effect of Juniperus virginiana L. essential oil and determination of its active constituents // Physiology & Behavior. – 2018. – Vol. 189. – P. 50-58. DOI: 10.1016/j.physbeh.2018.01.004

50. Zheljazkov V.D., Cantrell C.L., Semerdjieva I., Radoukova T., Stoyanova A., Maneva V., Kačániová M., Astatkie T., Borisova D., Dincheva I. et al. Essential Oil Composition and Bioactivity of Two Juniper Species from Bulgaria and Slovakia // Molecules. – 2021. – Vol. 26(12). – P. 3659.

51. Zheljazkov V.D., Semerdjieva I.B., Dincheva I., Kacaniova M., Astatkie T., Radoukova T., Schlegel V. Antimicrobial and antioxidant activity of Juniper galbuli essential oil constituents eluted at different times // Industrial Crops and Products. – 2017. – Vol. 109. – P. 529-537.