Analysis of the lipophilic complex obtained from the roots Eremostachys laciniata (Lamiaceae) flora of Dagestan, Russia by chromatography‐mass spectroscopy

The objective was to determine the component composition of the lipophilic complex obtained from dried roots of Eremostachys laciniata flora of the Republic of Dagestan by gas chromatography with massselective detection (GC‐MS).

The object of the study are the roots of Eremostachys laciniata, harvested from wild plants of the flora of the Republic of Dagestan in the vicinity of Derbent. Using MAESTRO 7820 gas chromatograph with an Agilent 5975 mass spectrometer and an autoinjector, the component composition of the hexane and chloroform fractions of the lipophilic complex obtained by extracting dried roots with 96 % ethyl alcohol was determined. The analysis was performed using an HP‐5 capillary quartz column, 30 m x 0,25 mm x 0,25 μm, helium carrier gas. The components were identified using NIST 2.4 mass spectral libraries and literature data.

The results of component analysis of the hexane and chloroform fractions of the lipophilic complex demonstrated a wide range of structurally diverse components. The content of extractive substances extracted from the roots with 96 % alcogol was 3,25 % based on dry raw material. In the lipophilic fractions studied, 42 compounds were identified – mainly terpenes, phytosterols, fatty acids and their esters and aromatic compounds. It was established that the groups of substances studied are extracted from the roots by various solvents unevenly; the nature of their distribution depends, among other things, on polarity.

The phytochemical data presented supplement our knowledge of the component composition of the subterranean organs of Eremostachys laciniata. Further study of this promising medicinal plant could expand the use of preparations from its raw materials in medical and pharmaceutical practice.

1. Ilyina T.A. Bol'shaya illyustrirovannaya entsiklopediya lekarstvennykh rastenii [The Great Illustrated Encyclopedia of Medicinal Plants]. Moscow, Eksmo Publ., 2014, 304 p. (In Russian)

2. Gosudarstvennaya Farmakopeya Rossiiskoi Federatsii [State Pharmacopoeia of the Russian Federation]. XIV edition. In 4 volumes. Moscow, 2018. (In Russian)

3. Rastitel'nye resursy Rossii: Dikorastushchie tsvetkovye rasteniya, ikh komponentnyi sostav i biologicheskaya aktivnost'. T. 4. Semeistva Caprifoliaceae – Lobeliaceae [Plant resources of Russia: Wild flowering plants, their component composition and biological activity. Vol. 4. Families Caprifoliaceae – Lobeliaceae]. St. Petersburg, Moscow, KMK Publ., 2011, 630 p. (In Russian)

4. The Plant List. Version 1.1. 2013. Available at: http://www.theplantlist.org/ (accessed 15.01.2015)

5. Nisar M., Khan S., Dar A., Rehman W., Khan R., Jan I. Antidepressant screening and flavonoids isolation from Eremostachys laciniata (L) Bunge. African Journal of Biotechnology, 2011, vol. 10, no. 9, pp. 1696–1699. http://dx.doi.org/10.5897/AJB10.1254

6. Çalış I., Guvenç A., Armagan M., Koyuncu M., Gotfredsen C.H., Jensen S.R. Secondary metabolites from Eremostachys laciniata. Natural Product Communications, 2008, vol. 3, no. 2, pp. 117–124. http://dx.doi.org/10.1177/1934578X0800300202

7. Zvezdina Е.V., Dayronas J.V., Bochkareva I.I., Zilfikarov I.N., Babaeva E.Yu., Ferubko E.V., Guseynova Z.A., Serebryanaya F.K., Kaibova S.R., Ibragimov T.A. Members of the family Lamiaceae Lindl. as sources of medicinal plant raw materials to obtain neurotropic drugs. Pharmacy and Pharmacology, 2020, vol. 8, no. 1, pp. 4–28. (In Russian) http://dx.doi.org/10.19163/2307‐9266‐2020‐8‐1‐4‐28]

8. Asgharian P., Delazar A., Asnaashari S. Chemical Constituents of Eremostachys macrophylla Montbr. and Auch. Aerial Parts. Pharmaceutical Sciences, 2020, vol. 26, no. 2, pp. 203–208. http://dx.doi.org/10.34172/PS.2019.65

9. Navaei M.N., Mirza M. Chemical composition of the oil of Eremostachys laciniata (L.) Bunge from Iran. Flavour and fragrance journal, 2006, vol. 21, no. 4, pp. 645–646. http://dx.doi.org/10.1002/ffj.1635

10. Bajalan I., Zand M., Goodarzi M., Darabi M. Antioxidant activity and total phenolic and flavonoid content of the extract and chemical composition of the essential oil of Eremostachys laciniata collected from Zagros. Asian Pacific Journal of Tropical Biomedicine, 2017, vol. 7, no. 2, pp. 144–146. http://dx.doi.org/10.1016/j.apjtb.2016.11.022

11. Khan A.M., Agnihotri N.K., Singh V.K., Joshi M.C., Kumar K. Conventional Medicinal Uses and Chemical Structure of Important Secondary Metabolites in the Genus Eremostachys: A Literature Review. An International Peer Reviewed Open Access Journal, 2022, vol. 15, no. 1, pp. 35–44. http://dx.doi.org/10.21786/bbrc/15.1.5

12. Delazar A., Modarresi M., Nazemiyeh H., Fathi‐Azad F., Nahar L., Sarker S.D. Furanolabdane diterpene glycosides from Eremostachys laciniata. Natural Product Communications, 2008, vol. 3, no. 6, pp. 873–876. http://dx.doi.org/10.1177/1934578X0800300609

13. Çalıs I., Baser K.H.C. Review of Studies on Phlomis and Eremostachys Species (Lamiaceae) with emphasis on iridoids, phenylethanoid glycosides, and essential oils. Planta Medica, 2021, vol. 87, no. 14, pp. 1128–1151. http://dx.doi.org/10.1055/a‐1527‐4238

14. Delazar A., Asl B.H., Mohammadi O., Afshar F.H., Nahar L., Modarresi M., Nazemiyeh H., Sarker S.D. Evaluation of analgesic activity of Eremostachys laciniata in mice. Journal of Natural Remedies, 2009, vol. 9, no. 1, pp. 1–7. http://dx.doi.org/10.18311/jnr/2009/213

15. Lindler B.N., Long K.E., Taylor N.A., Lei W. Use of herbal medications for treatment of osteoarthritis and rheumatoid arthritis. Medicines, 2020, vol. 7, no. 11, pp. pp. 67. http://dx.doi.org/10.3390/medicines7110067

16. Mahmood S., Agrawal A. Utility of Herbal plants for treating osteoarthritis and rheumatoid arthritis. Indian Journal of Integrative Medicine, 2022, vol. 2, no. 2, pp. 30–34.

17. Aliev A.M., Murtazaliev R.A., Vagabova F.A., Guseynova Z.A., Ramazanova B.A., Islamova F.I., Alibegova A.N., Osmanov R.M., Mallaliev M.M., Mamalieva M.M., Radzhabov G.K., Anatov D.M., Bussmann R.W. Ethnobotany of Dagestan. Ethnobotany Research and Applications, 2023, vol. 26, pp. 1–63. http://dx.doi.org/10.32859/era.26.66.1‐63

18. Saha P., Biswas D., Roy P., Majumdar M., Roy S., Manna R., Chanda A., Das S., Mukherjee M., Dey S., Das D. Herbs Having Analgesic Activity. Journal for Research in Applied Sciences and Biotechnology, 2023, vol. 2, no. 5, pp. 1–11. https://doi.org/10.55544/jrasb.2.5.1

19. Samarpita S., Rasool M. Majoon chobchini reinstates PDL‐1 expression and blocks dendritic cell‐T helper 17 pathogenic axis in rheumatoid arthritis animal model. Cytokine, 2023, vol. 163, article id: 156136. https://doi.org/10.1016/j.cyto.2023.156136

20. Talukdar A.J., Mani R.K., Malli R., Shree S., Md F. The role of medicinal plants in rheumatoid arthritis‐an updated review. International Journal of Indigenous Herbs and Drugs, 2023, vol. 8, no. 3, pp. 16–20. https://doi.org/10.46956/ijihd.v8i3.459

21. Delazar A., Sarker S.D., Nahar L., Jalali S.B., Modaresi M., Hamedeyazdan S., Babaei H, Javadzadeh Y, Asnaashari S, Moghadam S.B. Rhizomes of Eremostachys laciniata: isolation and structure elucidation of chemical constituents and a clinical trial on inflammatory diseases. Advanced pharmaceutical bulletin, 2013, vol. 3, no. 2, pp. 385–393. http://dx.doi.org/10.5681/apb.2013.062

22. Hariri A.S., Shayesteh S., Asgharian P., Chamanara M., SadrzadehAfshar M.S. Eremostachys binalodensis, a potential therapeutic choice for gingival inflammatory wounds. Journal of Contemporary Medical Sciences, 2021, vol. 7, no 3, pp. 140–144. https://doi.org/10.22317/jcms.v7i3.976

23. Modaressi M., Delazar A., Nazemiyeh H., Fathi‐Azad F.,Smih E., Rahman M.M., Sarker S.D. Antibacterial iridoid glucosides from Eremostachys laciniata. Phytotherapy Research, 2009, vol. 23, no 1, pp. 99–103. http://dx.doi.org/10.1002/ptr.2568

24. Al Kateeb A.I., Tufekci E.F., Baloglu M.C., Zengin G., Yıldıztugay E., Altunoglu Y.C. Antibacterial Effects of Phlomoides molucelloides (Bunge) Salmaki. Kahramanmaraş Sütçü İmam Üniversitesi Tarım ve Doğa Dergisi, 2022, vol. 25, no. Ek Sayı 2, pp. 402–410. https://doi.org/10.18016/ksutarimdoga.v25i73358.107798

25. Ahmadnia P., Nourafcan H., Assadi A., Faramarzi A. Eremostachys laevigata Bunge responses to different extraction solvents and methods: physiological, biochemical, and antibacterial attributes. Notulae Botanicae Horti Agrobotanici Cluj‐Napoca, 2024, vol. 52, no. 2, pp. 13232–13232. https://doi.org/10.15835/nbha52213232

26. Talebi M., Oskouie A.A., Mahboubi A., Khani M., Mojab F. Analysis of Eremostachys hyoscyamoides essential oil composition and assessing the antibacterial and antioxidant properties of the ethanol extract. Heliyon, 2024, vol. 10, no. 21. https://doi.org/10.1016/j.heliyon.2024.e38389

27. Faryabi E., Noori M., Mousavi A., Jafari A. Chemotaxonomy of Wild Lamiaceae Taxa Based on Their Flavonoids Profiles. Journal of Rangeland Science, 2021, vol. 11, no. 3, pp. 269–282.

28. Star D.M., Salih S.H., Mustafa R.A., Fiaq K. Phytochemical Screening and Antifungal Efficacy of Eremostachys lacinata (L.) Bunge. Plant Extract and Potential healthy attribute of Active compounds. Clinical Research and Clinical Reports, 2024, vol. 3, no. 6. http://dx.doi.org/10.31579/2835‐8325/100

29. Ramazanova Z.R., Zilfikarov I.N., Asadulaev Z.M., Guseynova Z.A. Anatomical structure of vegetative and generative organs of Eremostachys laciniata (Lamiaceae). Botanical Journal of the North Caucasus, 2024, no. 1, pp. 28–43. (In Russian) http://dx.doi.org/10.33580/24092444_2024_1_28

30. Flora SSSR [Flora of the USSR]. Moscow, Leningrad, USSR Academy of Sciences Publ., 1954, vol. 21, 704 p. (In Russian)

31. Grossheim A.A. Flora Kavkaza [Flora of the Caucasus]. Leningrad, USSR Academy of Sciences Publ., 1967, vol. 7, 894 p. (In Russian)

32. Zernov A.S., Abilova I.E. Osobennosti biomorfologii Eremostachys laciniata (L.) Bunge (Labiatae) [Features of biomorphology of Eremostachys laciniata (L.) Bunge (Labiatae)]. Materialy X mezhdunarodnoj konferencii po ekologicheskoj morfologii rastenij, posvyashchennoj pamyati I.G. i T.I. Serebryakovyh, T. 2, Moskva, 27–30 noyabrya, 2019. [Procedings of the X International Conference on Ecologial Morphology of Plants, dedicated to the memory of I.G. and T.I. Serebryakov, V. 2, Moskow, 27–30 November, 2019]. Moscow, 2019, pp. 3–8. (In Russian)

33. Murtazaliev R.A. Konspekt flory Dagestana [Conspectus of the flora of Dagestan]. Makhachkala, Epoha Publ., 2009, vol. 3, 304 p. (In Russian)

34. Khan S., Nisar M., Rehman W., Khan R., Nasir F. Anti‐inflammatory study on crude methanol extract and different fractions of Eremostachys laciniata. Pharmaceutical biology, 2010, vol. 48, no. 10, pp. 1115–1118. http://dx.doi.org/10.3109/13880200903517950

35. Mohammad Pour S., Hakimi S., Delazar A., Javad Zadeh Y., Mallah F. Eremostachys laciniata as effective as rectal diclofenac suppository in cesarean section pain relief: A triple‐blind controlled clinical trial. Journal of Endometriosis and Pelvic Pain Disorders, 2020, vol. 12, no. 1, pp. 26–34. https://doi.org/10.1177/2284026519899010