Coumarins of genus Ferula L. (Apiaceae Lindl.)

Authors

  • T.S. Khosnutdinova L.N. Gumilyov Eurasian National University, 2 Satpaev Str., Astana, Kazakhstan
  • N.G. Gemejiyeva Institute of Botany and Phytointroduction, 36 “D” Timiryazev Str., Almaty, Kazakhstan
  • Zh.Zh. Karzhaubekova Institute of Botany and Phytointroduction, 36 “D” Timiryazev Str., Almaty, Kazakhstan
  • N.A. Sultanova L.N. Gumilyov Eurasian National University, 2 Satpaev Str., Astana, Kazakhstan

DOI:

https://doi.org/10.18321/ectj1494

Keywords:

Ferula L., Coumarins, Furanocoumarins, Terpene coumarins, Ethers, Glycosides, Biological activity

Abstract

The biologically active coumarins from Ferula L. species of the family Apiaceae Lindl. for the period 1970 to 2022 have been reviewed. The phytochemical investigation of different parts of Ferula L., including gum resin, leaves, fruits, seeds, roots, rhizomes, and resins led to the separation of different types of coumarins. Nearly 185 coumarins were isolated from 35 species of Ferula L. growing in different countries. Coumarins are represented mainly by umbelliferone (7-O-hydroxycoumarin) derivatives substituted in the C-7 position of aglycone, furanocoumarins and metabolites have terpene fragments, esters and glycosides. Umbelliferon is found as a taxon for the genus Ferula L. Some «unusual» metabolites have a furan fragment attached to the pyrone ring. Coumarins are of the psoralen type, containing a furan ring in the C-6 and C-7 positions of the primary skeleton. The rare coumarins with terpene fragments (hemiterpene, monoterpen, sesquiterpene) were reported. The biological activities of some extracts and individual metabolites such as antiinflammatory, cytotoxicity, antibacterial, antileishmanial, antiviral, antigenotoxic, antitumor, anticoagulant, antioxidant, antimycobacterial, inhibition a-glucosidase, antileishmanial were found.

References

(1). M.S. Sagyndykova, A. Imanbayeva, Y. Suleimen, M. Ishmuratova, Bulletin of the Karaganda University (chemistry series) 96 (2019) 25‒34.

(2). N.V. Pavlov, Flora Kazahstana [Flora of Kazakhstan], Izdatel’stvo akademii nauk Kazahskoj SSR: Alma-Ata, 1963. Vol. 6. p. 466 (in Russian).

(3). L.M. Grudzinskaya, N.G. Gemedzhieva, N.V. Nelina, Zh.Zh. Karzhaubekova, Annotirovannyj spisok lekarstvennyh rastenij Kazahstana [Annotated list of medicinal plants of Kazakhstan] Almaty, 2014. p. 200. (in Russian)

(4). K. Kamoldinov, M. Sobirov, A. Nishonov, et al., Universum: Chemistry and biology 7 (2021) 22–26. URL

(5). Z.-Q. Wang, C. Huang, J. Huang, H.-Y. Han, et al., RSC Adv. 4 (2014) 14373–14377. Crossref

(6). J. Huang, H.-Y. Han, G.-Y. Li, H.-Y. Wang, et al., J. Asian Nat. Prod. Res. 15 (2013) 1100–1106. Crossref

(7). H. Hashemzadeh, M. Iranshahy, M. Iranshahi, H. Raissi, Comput. Biol. Med. 146 (2022) 105566. Crossref

(8). C. Kahraman, G. Topcu, E. Bedir, I.I. Tatli, et al., Saudi Pharm. J. 27 (2019) 525–531. Crossref

(9). R. Niazmand, B. Razavizadeh, J. Food Sci. Technol. 58 (2021) 2148–2159. Crossref

(10). M. Iranshahy, K.H. Mohammad, J. Essent. Oil-Bear. Plants 11 (2013) 350–355. Crossref

(11). R. Han, Y. Sun, R. Ma, D. Wang, et al., Evid.-Based Complement. Altern. Med. 29 (2022) 5092742. Crossref

(12). Z.E. Nazari, M. Iranshahi, Phytother. Res. 25 (2011) 315–323. Crossref

(13). Z. Sattar, M. Iranshahi, Iran J. Basic Med. Sci. 20 (2017) 1–8. Crossref

(14). M. Mohammadhosseini, A. Venditti, S.D. Sarker, L. Nahar, et al., Ind. Crops Prod. 1 (2018) 350–394. Crossref

(15). M.T. Khayat, M. Alharbi, K.F. Ghazawi, G.A. Mohamed, et al., Plants 12 (2023) 902. Crossref

(16). P. Taghinia, M.H. Haddad Khodaparast, M. Ahmadi, J. Food Meas. Charact. 13 (2019) 2980–2987. Crossref

(17). A.R. Kurbonov, M.G. Pimenov, Botanical Journal 101 (2016) 1220–1239. Crossref

(18). E.Kh. Batirov, M.P. Yuldashev, G.A. Nezhinskaya, V.M. Malikov, Chem. Nat. Compd. 5 (1979) 727–728. Crossref

(19). Z.A. Kuliev, T.Kh. Khasanov, V.M. Malikov, Coumarins of Ferula conocaula, Chem. Nat. Compd. 1 (1982) 120–121.

(20). A.A. Nabiev, V.M. Malikov, T.Kh. Khasanov, Chem. Nat. Compd. 19 (1983). Crossref

(21). N.E. Ermatov, A.I. Ban’kovskii, M.E. Perel’son, Chem. Nat. Compd. 2 (1967) 125–127. Crossref

(22). Y. Xing, N. Li, D. Zhou, G. Chen, et al., Planta Med. 83 (2017) 135–142. Crossref

(23). P. Zhou, Y. Takaishi, H. Duan, B. Chen, et al., Phytochemistry 53 (2000) 689–697. Crossref

(24). H. Zarei, R. Rezaee, E. Behravan, F. Soltani, F. Mosaffa, et al., Nat. Prod. Res. 27 (2013) 1016–1019. Crossref

(25). M.H. Abd El-Razek, Y.-C. Wu, F.-R. Chang, J. Chin. Chem. Soc. 54 (2007) 235–238. Crossref

(26). I.A. Kiryanova, Yu.E. Sklyar, M.G. Pimenov, Chem. Nat. Compd. 18 (1982). Crossref

(27). K. Kojima, K. Isaka, P. Ondognii, O. Zevgeegiin, et al., Chem Pharm Bull. 48 (2000) 353–356Crossref

(28). T. Motai, A. Daikonya, S. Kitanaka, Chem. Pharm. Bull. 61 (2013) 618–623. Crossref

(29). M.I. Choudhary, I. Baig, M. Nur-e-Alam, S. Shahzad-ul-Hussan, P. Öndognii, et al., Helv. Chim. Acta 84 (2001). Crossref

(30). M. Iranshahi, F. Amanolahi, B. Schneider, Avicenna J. Phytomed. 2 (2012) 133–138. Crossref

(31). K.A. Eshbakova, A.I. Saidkhodzhaev, Chem. Nat. Compd. 39 (2003) 221–222. Crossref

(32). É.K. Khalilova, A.I. Saidkhodzhaev, Chem. Nat. Compd. 34 (1998) 506–507. Crossref

(33). G. Li, X. Li, L. Cao, L. Zhang, et al., Fitoterapia 103 (2015) 222–226. Crossref

(34). M.S. Abdel-Kader, M.H. Alqarni, S. Baykan, B. Oztürk, et al., Separations 8 (2022) 206. Crossref

(35). V.Y. Bagirov, N.P. Kir’yalov, V.I. Sheichenko, Chem. Nat. Compd. 5 (1969) 504–505. Crossref

(36). D. Dastan, P. Salehi, A. Reza Gohari, S. Zimmermann, et al., Phytochemistry 78 (2012) 170–178. Crossref

(37). A.U. Babekov Terpenoidnye kumariny i slozhnye efiry dvuh vidov roda Ferula L. [Terpenoid coumarins and esters of two species of the genus Ferula L.] Innovacionnye usloviya razvitiya nauki i obrazovaniya v mezhkul’turnom vzaimodejstvii: kompleksnyj podhod, Cuhum, 09–12 dekabrya 2015 goda. Cuhum: Ural’skij gosudarstvennyj pedagogicheskij universitet. 2015. P. 25-28. (in Russian).

(38). G.A. Zhukov, A.P. Prokopenko, Chem. Nat. Compd. 3 (1967) 177–176. Crossref

(39). M.H. Abd El-Razek, S. Ohta, A.A. Ahmed, T. Hirata, Phytochemistry 58 (2001) 1289–1295. Crossref

(40). S. Bashir, M. Alam, A. Adhikari, R.L. Shrestha, et al., Phytochem. Lett. 9 (2014). Crossref

(41). G. Li, J. Wang, X. Li, L. Cao, et al., Phytochem. Lett. 13 (2015) 123–126. Crossref

(42). M. Iranshahi, M. Mojarab, H. Sadeghian, M.Y. Hanafi-Bojd, et al., Phytochemistry 69 (2008) 473–478. Crossref

(43). N.A. Sultanova, Zh.A. Abilov, A.K. Umbetova, M.I. Choudhary, Eurasian Chem.-Technol. J. 15 (2013) 219–226. Crossref

(44). E. Shults, Eurasian Chem.-Technol. J. 15 (2013) 175–187. Crossref

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Published

2023-03-20

How to Cite

Khosnutdinova, T., Gemejiyeva, N., Karzhaubekova, Z., & Sultanova, N. (2023). Coumarins of genus Ferula L. (Apiaceae Lindl.). Eurasian Chemico-Technological Journal, 25(1), 39–56. https://doi.org/10.18321/ectj1494

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