Sesquiterpene coumarins of Ferula tadshikorum Pimenov

Abstract

Eight known sesquiterpene coumarins compounds were isolated from the root of Ferula tadshikorum Pimenov by column chromatography and semi-preparative HPLC. Their structures were identified by the spectroscopic data and comparison with literatures as, mogoltadone (1), badrakemin (2), colladonin (3), nevskin (4), gummosin (5), samarcandin (6), feshurin (7), samarcandin acetate (8). All compounds were isolated from F. tadshikorum for the first time.

Keywords

• Ferula tadshikorum
• sesquiterpene coumarins
• samarcandin acetate
• mogoltadone
• badrakemin

References

1. Sonigra P, Meena M. Metabolic Profile, Bioactivities, and Variations in the Chemical Constituents of Essential Oils of the Ferula Genus (Apiaceae). Front Pharmacol. 2021;11:608649. https://doi.org/10.3389/fphar.2020.608649.
2. Abd El-Razek MH, Wu YC, Chang FR. Sesquiterpene coumarins from Ferula foetida. J Chin Chem Soc. 2007; 54: 235– 238. https://doi.org/10.1002/jccs.200700035.
3. Kh, Jun Li, Eshbakova K, Sagdullaev Sh, Gaoya Xu, Yubo Zhou, Jia Li, Aisa HA. Sesquiterpene coumarins from Ferula samarkandica Korovin and their bioactivity. Phytochemistry. 2021;187:112705. https://doi.org/10.1016/j.phytochem.2021.112705.
4. Gliszczy´nska A, Brodelius PE. Sesquiterpene coumarins. Phytochemistry Rev. 2012; 11: 77–96. https://doi.org/10.1007/s11101-011-9220-6.
5. Iranshahi M, Rezaee R, Sahebkar A, Bassarello C, Piacente S, Pizza C, Sesquiterpene coumarins from the fruits of Ferula badrakema. Pharm Biol. 2009; 47: 344–347. https://doi.org/10.1080/13880200902752884.
6. Iranshahi M, Masullo M, Asili A, Hamedzadeh A, Jahanbin B, Festa M, Capasso A, Piacente S. Sesquiterpene coumarins from Ferula gumosa. J Nat Prod. 2010; 73; 1958–1962. https://doi.org/10.1021/np100487j.
7. Li GZ, Wang JC, Li XJ, Cao L, Lv N, Chen G, Zhu J, Si JY. Two new sesquiterpene coumarins from the seeds of Ferula sinkiangensis. Phytochemistry Lett. 2015; 13: 123–126. https://doi.org/10.1016/j.phytol.2015.06.002.
8. Asghari J, Atabaki V, Baher E, Mazaheritehrani M. Identification of sesquiterpene coumarins of oleo-gum resin of Ferula assa-foetida L. from the Yasuj region. Nat Prod Res. 2016; 30: 350–353. https://doi.org/10.1080/14786419.2015.1050669.

9. Nassar MI, Abumustafa EA, Ahmed AA. Sesquiterpene coumarins from Ferula-assafoetida L. Pharmazie. 1995; 50: 766–767.
10. Tashkhodzhaev B, Turgunov KK, Izotova LY, Kamoldinov KS. Stereochemistry of samarcandin-type sesquiterpenoid coumarins. Crystal structures of Feshurin and nevskin. Chem Nat Compd. 2015 ; 51: 242–246. https://doi.org/10.1007/s10600-015-1253-4
11. Li GZ, Li XJ, Cao L, Zhang LJ, Shen LG, Zhu J, Wang JC, Si JY. Sesquiterpene coumarins from seeds of Ferula sinkiangensis. Fitoterapia. 2015; 103: 222–226. https://doi.org/10.1016/j.fitote.2015.03.022.
12. Xing YC, Li N, Zhou D, Chen G, Jiao K, Wang WL, Si YY, Hou Y. Sesquiterpene coumarins from Ferula sinkiangensis act as neuroinflammation inhibitors. Planta Med. 2007; 83: 135–142. https://doi.org/10.1055/s-0042-109271.
13. Lee CL, Chiang LC, Cheng LH, Liaw CC, El-Razek MH, Chang FR, Wu YC. Influenza A (H1N1) antiviral and cytotoxic agents from Ferula assa-foetida. J Nat Prod. 2009; 72: 1568–1572. https://doi.org/10.1021/np900158f Flora of Uzbekistan, Vol. V, Publ. Acad. Sci. Uzbek, Tashkent, 2023. pp.288
14. Abu Ali ibn Sino (Avetsenna). Canon of medical science. - Tashkent: Publishing House of the Academy of Sciences of the UzSSR, 1954: 1: 548.
15. Rahmonkulov U, Avalboyev O, Uzbekistan rugs .Tashkent: Science and technology. 2016, pp .244. Rakhimov S, Denisova GR. Some features of the underground organs of Ferula tadshikorum M. Pimen (Ferula L.). Bulletin of Altai State Agrarian University. 2017; 8(154): 87.
16. Khamraeva DT, Tukhtaeva DN, Khojimatov OK, Rainer W. B Ferula tadshikorum Pimenov - introduction, chemical composition and use in folk medicine. Ethnobot Res Appl. 2023; (25)24: 1-10.
17. Sharopov FS, Khalifaev PD, Satyal P, Sun Y, Safomuddin A, Musozoda S, Wink M, Setze WN. The chemical composition and biological activity of the essential oil from the underground parts of Ferula tadshikorum (Apiaceae). Record Nat Prod. 2018; 13(1): 18-23. http://doi.org/10.25135/rnp.65.18.02.089.
18. Perel'son M, Bandyshev V, Sklyar YE, Vezhkhovska-Renke K, Veselovskaya NV, Pimenov MG. New terpenoid coumarins from Ferula tadshikorum. Chem Nat Comp. 1976; 12: 533-537. https://doi.org/10.1007/BF00565176 Beselovskaya NV and. Sklyar EY. Deacetyltadzhikorin from Ferula tadshikorum. Chem Nat Comp. 1984: (20)3: 363. https://doi.org/10.1007/BF00575772
19. Khasanov TKh, Saidkhodzhaev AI, Nikonov GK. Structure and configuration of the coumarins mogoltadone and mogoltadin. Chem Nat Comp. 1974; 1: 20-23.
20. Saidkhodzhaev AI, Nikonov GK. Conformation of the configurations of badrakemin and gummosin. Chem Nat Comp, 1974; 1: 12-14. https://doi.org/10.1007/BF00568212
21. Asgharia J, Atabakia V, Bahera E, Mazaheritehrania M. Identification of sesquiterpene coumarins of oleo-gum resin of Ferula assa-foetida L. from the Yasuj region. Nat Prod Res. 2015; 1-4. http://dx.doi.org/10.1080/14786419.2015.105066
22. Abd El-Razek MH, Ohta S, Hirata T. Terpenoid coumarins of the genus Ferula. Heterocycles. 2003; 60: 689–716. https://doi.org/10.3987/rev-02-561.
23. Bagirov Yu, Kir'yalov NP, Sheichenko VI. Structure of samarcandin. Chem Nat Comp. 1970; (6)4: 465-466. https://doi.org/10.1007/BF00564257
24. Saidkhodzhaev AI, Malikov VM, Pimenov MG, Melibaev S. Terpenoid coumarins of Ferula lipskyi and F. vicaria. Chem Nat Comp. 1991; 27(2): 242-243. https://doi.org/10.1007/BF00629772
25. Kir'yalov NP, Bukreeva TV. Samarcandin acetate from the roots of Ferula pseudooreoselinum. Chem Nat Compd.1972; 8: 777–778. https://doi.org/10.1007/BF00564609