Triterpenoids from Scorzonera veratrifolia Fenzl

Abstract

DOI: 10.5152/IstanbulJPharm.2018.410411

The genus Scorzonera (Asteraceae) has several species which are used as a vegetable and in folk medicine all around the world. A phytochemical study was carried out on petroleum ether fraction of methanol extract obtained from the roots of Scorzonera veratrifolia Fenzl (Bitlis / Turkey) to investigate the terpenoid composition of the plant. Column chromatography, preparative thin layer chromatography and gas chromatography (GC) were used for separation of the compounds. Their structures were determined by using GC-MS and NMR techniques. Seventeen triterpenoids (ß-amyrin, ß-amyrin acetate, ß-amyrinone, germanicol, germanicol acetate, germanicone, α-amyrin, α-amyrin acetate, α-amyrinone, ψ – taraxasterol, ψ – taraxasterol acetate, taraxasterol, taraxasterol acetate, lupeol, lupeol acetate, lupenone, fern-7-en-3-one) and one sterol (ß-sitosterol) were determined. The presence of these compounds has been shown for the first time in S. veratrifolia. α-amyrinone, ß-amyrin, ß-amyrinone, ψ – taraxasterol and ψ – taraxasterol acetate are new for the genus Scorzonera.

Keywords

• Scorzonera veratrifolia,triterpenoids,sterol,GC-MS

References

1. Ahmad VU, Atta ur R (1994). Handbook of natural products data. Volume 2: pentacyclic triterpenoids. Elsevier Science, Amsterdam.
2. Altınordu F, Martin E, Makbul S, Coşkunçelebi K, Gültepe M (2015). Cytogenetic studies on some Scorzonera L. s.l. (Asteraceae) taxa from Turkey. Turk J Bot 39: 429-438.
3. Bahadır O, Çitoglu GS, Smejkal K, Dall'Acqua S, Özbek H, Cvacka J, Zemlicka M (2010). Analgesic compounds from Scorzonera latifolia (Fisch. and Mey.) DC. J Ethnopharmacol 131: 83-87.
4. Baytop T (1999). Türkiye'de Bitkilerle Tedavi Geçmişte ve Bugün (Therapy with medicinal plants in Turkey). Nobel Tıp, İstanbul.
5. Budzikiewicz H, Wilson JM, Djerassi C (1963). Mass Spectrometry in Structural and Stereochemical Problems. XXXII.1 Pentacyclic Triterpenes. J Am Chem Soc 85: 3688-3699.
6. Chamberlain DF (1975). Scorzonera L. In: PH Davis (ed./eds) FLORA OF TURKEY and the East Aegean Islands, V, Edinburgh University Press, Edinburgh, 632-657.
7. Coşkunçelebi K, Makbul S, Gültepe M, Okur S, Güzel ME (2015). A conspectus of Scorzonera s.l. in Turkey. Turk J Bot 39: 76-87.
8. Dakeng S, Duangmano S, Jiratchariyakul W, U-Pratya Y, Bögler O, Patmasiriwat P (2012). Inhibition of Wnt signaling by cucurbitacin B in breast cancer cells: Reduction of Wnt associated proteins and reduced translocation of galectin-3-mediated β-catenin to the nucleus. J Cell Biochem 113: 49-60.

9. Ding N, Yamashita U, Matsuoka H, Sugiura T, Tsukada J, Noguchi J, Yoshida Y (2011). Apoptosis induction through proteasome inhibitory activity of cucurbitacin D in human T‐cell leukemia. Cancer 117: 2735-2746.
10. Dudhgaonkar S, Thyagarajan A, Sliva D (2009). Suppression of the inflammatory response by triterpenes isolated from the mushroom Ganoderma lucidum. Int J Immunopharmacol 9: 1272-1280.
11. Ezzat SM, Abdallah HM, Fawzy GA, El-Maraghy SA (2012). Hepatoprotective constituents of Torilis radiata Moench (Apiaceae). Nat Prod Res 26: 282-285.
12. Gao Y, Zhang R, Zhang J, Gao S, Gao W, Zhang H, Wang H, Han B (2011). Study of the Extraction Process and In Vivo Inhibitory Effect of Ganoderma Triterpenes in Oral Mucosa Cancer. Molecules 16: 5315.
13. Gawrońska-Grzywacz M, Krzaczek T (2007). Identification and determination of triterpenoids in Hieracium pilosella L. J Sep Sci 30: 746-750.
14. Granica S, Lohwasser U, Johrer K, Zidorn C (2015). Qualitative and Quantitative Analyses of Secondary Metabolites in Aerial and Subaerial of Scorzonera hispanica L. (Black Salsify). Food Chem 173: 321-331.
15. Hooper SN, Chandler RF, Lewis E, Jamieson WD (1982). Simultaneous determination ofSonchus arvensis L. triterpenes by gas chromatography-mass spectrometry. Lipids 17: 60-63.
16. Jehle M, Bano J, Ellmerer EP, Zidorn C (2010). Natural products from Scorzonera aristata (Asteraceae). Nat Prod Commun 5: 725-727.
17. Laszczyk MN (2009). Pentacyclic Triterpenes of the Lupane, Oleanane and Ursane Group as Tools in Cancer Therapy. Planta Med 75: 1549-1560.
18. Menichini F, Statti G, Delle Monache F (1994). Flavonoid glycosides from Scorzonera columnae. Fitoterapia 65: 555-556.
19. Mükemre M, Behçet L, Çakılcıoğlu U (2016). Survey of wild food plants for human consumption in villages of Çatak (Van-Turkey). Indian J Tradit Knowle 15: 183-191.
20. Narayan V, Kodihalli RC, Chiaro C, Cary D, Aggarwal BB, Henderson AJ, Prabhu KS (2011). Celastrol Inhibits Tat-mediated Human Immunodeficiency Virus (HIV) Transcription and Replication. J Mol Biol 410: 972-983.
21. Oliveira P, Turatti I, Camilo Rodrigues de Oliveira D (2006). Comparative analysis of triterpenoids from Mikania cordifolia collected from four different locations. Braz J Pharm Sci 42: 547-552.
22. Öksüz S, Gören N, Ulubelen A (1990). Terpenoids from Scorzonera tomentosa. Fitoterapia 61: 92-93.
23. Paraschos S, Magiatis P, Kalpoutzakis E, Harvala C, Skaltsounis AL (2001). Three New Dihydroisocoumarins from the Greek Endemic Species Scorzonera cretica. J Nat Prod 64: 1585-1587.
24. Sarı A (2010). Two new 3-benzylphthalides from Scorzonera veratrifolia Fenzl. Nat Prod Res 24: 56-62.
25. Sarı A (2012). Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Nat Prod Res 26: 50-55.
26. Sarı A, Özbek B, Özgökçe F (2009). Antimicrobial Activities of Two Scorzonera Species Growing in Turkey. Asian J Chem 21: 4785-4788.
27. Shiojima K, Masuda K, Suzuki H, Lin T, Ooishi Y, Ageta H (1995). Composite Constituents : Forty-Two Triterpenoids Including Eight Novel Compounds Isolated from Picris hieracioides subsp. japonica. Chem Pharm Bull 43: 1634-1639.
28. Thyagarajan A, Jedinak A, Nguyen H, Terry C, Baldridge LA, Jiang J, Sliva D (2010). Triterpenes From Ganoderma Lucidum Induce Autophagy in Colon Cancer Through the Inhibition of p38 Mitogen-Activated Kinase (p38 MAPK). Nutrition and Cancer 62: 630-640.
29. Tsevegsuren N, Edrada R, Lin W, Ebel R, Torre C, Ortlepp S, Wray V, Proksch P (2007). Biologically Active Natural Products from Mongolian Medicinal Plants Scorzonera divaricata and Scorzonera pseudodivaricata. J Nat Prod 70: 962-967.
30. Turan M, Kordali S, Zengin H, Dursun A, Sezen Y (2003). Macro and Micro Mineral Content of Some Wild Edible Leaves Consumed in Eastern Anatolia. Acta Agric Scand Sect B Soil Plant Sci 53: 129-137.
31. Wang B, Li G, Guan H, Yang L, Tong G (2009). A new erythrodiol triterpene fatty ester from Scorzonera mongolica. Acta Pharm Sin 44: 1258-1261.Wu QX, Su YB, Zhu Y (2011). Triterpenes and steroids from the roots of Scorzonera austriaca. Fitoterapia 82: 493-496.
32. Xie Y, Guo QS, Wang GS (2016). Flavonoid Glycosides and Their Derivatives from the Herbs of Scorzonera austriaca Wild. Molecules 21: 803.
33. Yang YJ, Yao J, Jin XJ, Shi ZN, Shen TF, Fang JG, Yao XJ, Zhu Y (2016). Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata. Phytochemistry 124: 86-98.
34. Zidorn C, Ellmerer-Müller EP, Stuppner H (2000). Tyrolobibenzyls - Novel secondery metabolites from Scorzonera humilis. HeIv Chim Acta 83: 2920-2925.