year 20, Issue 79 (8-2021)                   J. Med. Plants 2021, 20(79): 24-36 | Back to browse issues page


XML Persian Abstract Print


Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:

Valizadeh G, Nejad Ebrahimi S, Gholami M, Mazaheritehrani M, Rezadoost H, Sonboli A. Rearranged abietane diterpenoids from roots of Teucrium hircanicum L.. J. Med. Plants. 2021; 20 (79) :24-36
URL: http://jmp.ir/article-1-3073-en.html
1- Department of Chemistry, Faculty of Basic Sciences, Golestan University, Gorgan, Iran
2- Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran , s_ebrahimi@sbu.ac.ir
3- Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran
4- Department of Biology, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran
Abstract:   (309 Views)
Background: Medicinal plants play a significant role in preventing and treating diseases due to their traditional uses. Objective: The aim of the study was to isolate, purify and identify phytochemicals from the n-hexane extract of Teucrium hircanicum L. roots and evaluate the antioxidant activity of the extract and its purified compounds. Methods: The n-hexane extract (2.27 g) was extracted from the roots of this plant. The extract was fractionated by column chromatography with normal phase by eluting with n-hexane-EtOAc and following with EtOAc-Methanol. Fractions with similar phytochemical fingerprints combined to produce 23 main fractions. Final purification was carried out by preparative reversed-phase HPLC-UV. The structures of isolated were secured by different spectroscopic methods such as 1D, 2D NMR, and mass spectroscopy methods and comparing of these data with literature reported values. The antioxidant activity of the n-hexane extract of T. hircanicum roots and its purified diterpenoids was evaluated in DPPH assay and radical scavenging activity was calculated. Results: Extraction and isolation methods were used to purify three rearranged abietane-type diterpenoids villosin A (1), teuvincenone B (2) and 5, 8, 11, 13, 15-abietapentaen-7-one (3), a phenethyl ester namely 4-hydroxyphenethyl pentacosanoate (4) and one sterol namely 22-dehydroclerosterol (5). Conclusion: The n-hexane extract from roots of T. hircanicum and three rearranged abietane type diterpenoids were showed good antioxidant activities ranged from 3.5-4.3 μg/ml compared with the reference value (BHT = 16.5 μg/ml).
Full-Text [PDF 593 kb]   (237 Downloads)    
Type of Study: Research | Subject: Pharmacognosy & Pharmaceutics
Received: 2021/03/25 | Accepted: 2021/06/27 | Published: 2021/09/1

References
1. Saranraj P, Sivasakthi S and Deepa MS. Phytochemistry of pharmacologically important medicinal plants-A review. Int. J. Curr. Res. Chem. Pharm. Sci. 2016; 3: 56-66. [DOI:10.22192/ijcrcps.2016.03.11.009]
2. Farombi EO. African indigenous plants with chemotherapeutic potentials and biotechnological approach to the production of bioactive prophylactic agents. Afr. J. Biotech. 2003; 2: 662-671. [DOI:10.5897/AJB2003.000-1122]
3. Saranraj P and Stella D. Antibiogram of nosocomial infection and its antimicrobial drug resistance. Int. J. Pharm. Biol. Arch. 2011; 2: 1598-1610.
4. Piero NM, Njagi MJ, Kibiti MC, Ngeranwa JJN, Njagi NME, Njue MW and Gathumbi KP. Herbal management of diabetes mellitus: A rapidly expanding research avenue. Int. J. Curr. Pharm. Res. 2012; 4: 1-4.
5. Sisodia R, Verma S, Rani A and Dureja P. Antibacterial and antioxidant activity of lichen species Ramalina roesleri. Nat. Pro. Res. 2013; 27: 2235-2239. [DOI:10.1080/14786419.2013.811410]
6. Alves TM, Silva AF, Brandao M, Grandi TSM, Smania EFA, Junior AS and Zani CL. Biological screening of Brazillian medicinal plants. Memorias do Instituto Oswaldo Cruz. 2000; 95: 367-373. [DOI:10.1590/S0074-02762000000300012]
7. Harley RM, Atkins S, Budantsev AL, Cantino PD, Conn BJ, Grayer R, Harley MM, de Kok R, Krestovskaja T, Morales R, Paton AJ, Ryding O, and Upson T. "Labiatae," in Flowering Plants. Dicotyledons: Lamiales (except Acanthaceae including Avicenniaceae). Kadereit JW, (Ed.). Springer, Berlin, Germany. 2004, 167-275. [DOI:10.1007/978-3-642-18617-2_11]
8. Lamaison JL, Petitjean-Freytet C and Carnat A. Medicinal Lamiaceae with antioxidative activities, potential sources of rosmarinic acid. Pharm. Acta Helv. 1991; 66: 185-188.
9. Cuvelier ME, Berset C and Richard H. Antioxidant constituents in sage (Salvia officinalis). J. Agric. Food Chem. 1994; 42: 665-669. [DOI:10.1021/jf00039a012]
10. Khoury M, Stien D, Eparvier V, Ouaini N and Beyrouthy ME. Report on the medicinal use of eleven Lamiaceae species in Lebanon and rationalization of their antimicrobial potential by examination of the chemical composition and antimicrobial activity of their essential oils. J. Evid. Based Complementary Altern. Med. 2016; 33: 1-17. [DOI:10.1155/2016/2547169]
11. Navarro T and El Oualidi J. Synopsis of Teucrium L. (Lamiaceae) in the Mediterranean region and surrounding areas. Fl. Medit. 2000; 10: 349-363.
12. Govaerts RA, Paton A, Harvey Y, Navarro T and Del Rosario Garcia Pena M. World checklist of Lamiaceae. The Board of Trustees of the Royal Botanic Gardens. 2013; Kew, Kew. www.kew.org/wcsp/
13. Stanković M. Teucrium species: Biology and Applications. Springer Nature Switzerland AG. 2020. [DOI:10.1007/978-3-030-52159-2]
14. Ulubelen A, Topcu G and Sonmez U. Chemical and biological evaluation of genus Teucrium. Nat. Pro. Chem. 2000; 23: 591-648. [DOI:10.1016/S1572-5995(00)80139-8]
15. Eshratifar M, Attar F and Mahdigholi K. Micromorphological studies on nutlet and leaf indumentum of genus Teucrium L. (Lamiaceae) in Iran. Turk. J. Botany. 2011; 35: 25-35.
16. Abdollahi M, Karimpour H and Monsef-Esfehani HR. Antinociceptive effects of Teucrium polium L. total extract and essential oil in mouse writhing test. Pharm. Res. 2003; 48: 31-35. [DOI:10.1016/S1043-6618(03)00059-8]
17. Tariq M, Ageel AM, al-Yahya MA, Mossa JS and al-Said MS. Anti-inflammatory activity of Teucrium polium. Int. J. Tissue React. 1989; 11: 185-188.
18. Šamec D, Gruz J, Strnad M, Kremer D, Kosalec I, Grubešić RJ, Karlović K, Lucic A and Piljac-Žegarac J. Antioxidant and antimicrobial properties of Teucrium arduini L. (Lamiaceae) flower and leaf infusions (Teucrium arduini L. antioxidant capacity). Food Chem. Toxicol. 2010; 48: 113-119. [DOI:10.1016/j.fct.2009.09.026]
19. Ardestani A, Yazdanparast R and Jamshidi SH. Therapeutic effects of Teucrium polium extract on oxidative stress in pancreas of streptozotocin-induced diabetic rats. J. Med. Food. 2008; 11: 525-532. [DOI:10.1089/jmf.2006.0230]
20. Shahraki MR, Arab MR, Mirimokaddam E and Palan MJ. The effect of Teucrium polium (Calpoureh) on liver function, serum lipids and glucose in diabetic male rats. Iran. Biomed. J. 2007; 11: 65-68.
21. Gharaibeh MN, Elayan HH and Salhab AS. Hypoglycemic effects of Teucrium polium. J. Ethnopharmacol. 1988; 24: 93-99. [DOI:10.1016/0378-8741(88)90139-0]
22. Mousavi SM, Niazmand S, Hosseini M, Hassanzadeh Z, Sadeghnia HR, Vafaee F and Keshavarzi, Z. Beneficial effects of Teucrium polium and metformin on diabetes induced memory impairments and brain tissue oxidative damage in rats. Int. J. Alzheimers Dis. 2015; Volume 2015, Article ID 493729, 8. pages. [DOI:10.1155/2015/493729]
23. Niazmand S, Esparham M, Hassannia T and Derakhshan M. Cardiovascular effects of Teucrium polium L. extract in rabbit. Pharmacogn. Mag. 2011; 7: 260-264. [DOI:10.4103/0973-1296.84244]
24. Mahmoudabady M, Shafei MN, Niazmand S and Khodaee E. The effects of hydroalchoholic extract of Teucrium polium L. on hypertension induced by angiotensin II in rats. Int. J. Prev. Med. 2014; 5: 1255-1260.
25. BLOIS MS. Antioxidant determination by the use of a stable free radical. Nature. 1958; 181: 1199-1200. [DOI:10.1038/1811199a0]
26. Ulubelen A, Topcu G and Olcal S. Rearranged abietane diterpenes from Teucrium divaricatum subsp. villosum. Phytochemistry 1994; 37: 1371-1375. [DOI:10.1016/S0031-9422(00)90415-1]
27. Carreiras MC, Rodriguez B, de la Torre MC, Perales A, Torres MR, Savona G and Piozzi F. Rearranged abietane diterpenoids from the root of Teucrium polium subsp. vincentinum. Tetrahedron. 1990; 46: 847-860. [DOI:10.1016/S0040-4020(01)81367-3]
28. Fiorentino A, D'Abrosca B, Pacifico S, Scognamiglio M, D'Angelo G and Monaco P. abeo-Abietanes from Teucrium polium roots as protective factors against oxidative stress. Bioorg. Med. Chem. 2010; 18: 8530-8536. [DOI:10.1016/j.bmc.2010.10.037]
29. Vinh LB, Minh Nguyet NT, Yang SY, Kim JH, Vien LT, Huong PTT, Thanh NV, Cuong NX, Nam NH, Minh CV, Hwang I and Kim YH. A new rearranged abietane diterpene from Clerodendrum inerme with antioxidant and cytotoxic activities. Nat. Prod. Res. 2018; 32: 2001-2007. [DOI:10.1080/14786419.2017.1360885]
30. Topçu G, Kolak U, Balci K and Ulubelen A. Structure elucidation of a new rearranged abietane diterpene from a biologically active plant, Salvia eriophora. Nat. Prod. Commun. 2007; 2: 981-986. [DOI:10.1177/1934578X0700201004]
31. Akimanya A, Midiwo JO, Matasyoh J, Okanga F, Masila VM, Walker L, Tekwani BL, Muhammad I and Omosa LK. Two polymethoxylated flavonoids with antioxidant activities and a rearranged clerodane diterpenoid from the leaf exudates of Microglossa pyrifolia. Phytochem. Lett. 2015; 11: 183-187. [DOI:10.1016/j.phytol.2014.12.008]
32. Topçu G and Gören AC. Biological activity of diterpenoids isolated from Anatolian Lamiaceae plants. Rec. Nat. Prod. 2007; 1: 1-16.
33. Yin G, Zeng H, He M and Wang M. Extraction of Teucrium manghuaense and evaluation of the bioactivity of its extract. Int. J. Mol. Sci. 2009; 10: 4330-4341. [DOI:10.3390/ijms10104330]
34. Hu HJ, Zhou Y, Han ZZ, Shi YH, Zhang SS, Wang ZT and Yang L. Abietane diterpenoids from the roots of Clerodendrum trichotomum and their nitric oxide inhibitory activities. J. Nat. Prod. 2018; 81: 1508-1516. [DOI:10.1021/acs.jnatprod.7b00814]
35. Wang WX, Xiong J, Tang Y, Zhu JJ, Li M, Zhao Y, Yang GX, Xia G, Hu JF. Rearranged abietane diterpenoids from the roots of Clerodendrum trichotomum and their cytotoxicities against human tumor cells. Phytochemistry 2013; 89: 89-95. [DOI:10.1016/j.phytochem.2013.01.008]
36. Fan TP, Min ZD, Iinuma M and Tanaka T. Rearranged abietane diterpenoids from Clerodendrum mandarinorum. J. Asian Nat. Prod. Res. 2013; 2: 237-243. [DOI:10.1080/10286020008039917]
37. Kancheva VD and Kasaikina OT. Bio-Antioxidants - A Chemical Base of Their Antioxidant Activity and Beneficial Effect on Human Health. Bentham Science Publishers. 2013; 20: 4784-4805. [DOI:10.2174/09298673113209990161]
38. Rahimi MA, Nazeri V, Andi SA and Sefidkon F. Variation in essential oil composition of Teucrium hircanicum L. from Iran-A rich source of (E)-α-bergamotene. Nat. Prod. Res. 2018; 33: 1-6. [DOI:10.1080/14786419.2018.1466122]
39. Kazemizadeh Z, Basiri A and Habibi Z. Chemical composition of the essential oil of Teucrium hyrcanicum and T. chamaedrys L. SUBSP. chamaedrys from Iran. Chem.Nat. Compd. 2008; 44: 651-653. [DOI:10.1007/s10600-008-9164-2]

Add your comments about this article : Your username or Email:
CAPTCHA

Send email to the article author


Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

© 2021 CC BY-NC 4.0 | Journal of Medicinal Plants

Designed & Developed by : Yektaweb