Research Article


DOI :10.5152/IstanbulJPharm.2018.410411   IUP :10.5152/IstanbulJPharm.2018.410411    Full Text (PDF)

Triterpenoids from Scorzonera veratrifolia Fenzl

Betül ÇetinHasan ŞahinAynur Sarı

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.


PDF View

References

  • Acıkara OB, Çitoglu GS, Dall’Acqua S, Smejkal K, Cvacka J, Zemlicka M (2012). A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC. Nat Prod Res 26: 1892-1897. google scholar
  • Acıkara ÖB, Çitoğlu GS, Acqua SD, Cvacka J, Zemlicka M, Smejkal K (2014). Bioassay-guided isolation of the antinociceptive compounds motiol and ß-sitosterol from Scorzonera latifolia root extract. Pharmazie 69: 711-714. google scholar
  • Ahmad VU, Atta ur R (1994). Handbook of natural products data. Volume 2: pentacyclic triterpenoids. Elsevier Science, Amsterdam. google scholar
  • 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. google scholar
  • 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. google scholar
  • Baytop T (1999). Türkiye’de Bitkilerle Tedavi Geçmişte ve Bugün (Therapy with medicinal plants in Turkey). Nobel Tıp, İstanbul. google scholar
  • Benabdelaziz I, Haba H, Lavaud C, Benkhaled M (2014). Triterpenoids and flavonoid from Scorzonera undulata ssp. alexandrina. Int J Chem Biol Sci 5: 1-5. google scholar
  • 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. google scholar
  • Chamberlain DF (1975). Scorzonera L. In: PH Davis, VA Matthews, FK Kupicha, BS Parris (eds) Flora of Turkey and the East Aegean Islands, V, Edinburgh University Press, Edinburgh, 632-657. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • Erden Y, Kırbağ S, Yılmaz Ö (2013). Phytochemical composition and antioxidant activity of some Scorzonera species. Proc Natl Acad Sci, India, Sect B 83: 271-276. google scholar
  • Ezzat SM, Abdallah HM, Fawzy GA, El-Maraghy SA (2012). Hepatoprotective constituents of Torilis radiata Moench (Apiaceae). Nat Prod Res 26: 282-285. google scholar
  • 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. google scholar
  • Gawrońska-Grzywacz M, Krzaczek T (2007). Identification and determination of triterpenoids in Hieracium pilosella L. J Sep Sci 30: 746-750. google scholar
  • 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. google scholar
  • Harkati B, Akkal S, Bayat C, Laouer H, Franca MGD (2010). Secondary metabolites from Scorzonera undulata ssp. deliciosa (Guss.) Maire (Asteracae) and their antioxidant activities. Rec Nat Prod 4: 171-175. google scholar
  • Hooper SN, Chandler RF, Lewis E, Jamieson WD (1982). Simultaneous determination of Sonchus arvensis L. triterpenes by gas chromatography-mass spectrometry. Lipids 17: 60-63. google scholar
  • Jehle M, Bano J, Ellmerer EP, Zidorn C (2010). Natural products from Scorzonera aristata (Asteraceae). Nat Prod Commun 5: 725-727. google scholar
  • Laszczyk MN (2009). Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med 75: 1549-1560. google scholar
  • Menichini F, Statti G, Delle Monache F (1994). Flavonoid glycosides from Scorzonera columnae. Fitoterapia 65: 555-556. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • Öksüz S, Gören N, Ulubelen A (1990). Terpenoids from Scorzonera tomentosa. Fitoterapia 61: 92-93. google scholar
  • 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. google scholar
  • Pateh UU, K. HA, Garba M, Iliya I, Sule IM, Abubakar MS, A.A. A (2009). Isolation of stigmasterol, ß-sitosterol and 2-hydroxyhexadecanoic acid methyl ester from the rhizomes of Stylochiton lancifolius Pyer and Kotchy (Araceae). Nig Journ Pharm Sci 8: 19-25. google scholar
  • Sarı A (2010). Two new 3-benzylphthalides from Scorzonera veratrifolia Fenzl. Nat Prod Res 24: 56-62. google scholar
  • Sarı A (2012). Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Nat Prod Res 26: 50-55. google scholar
  • Sarı A, Özbek B, Özgökçe F (2009). Antimicrobial activities of two Scorzonera species growing in Turkey. Asian J Chem 21: 4785-4788. google scholar
  • 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. google scholar
  • 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. google scholar
  • Tolstikhina VV, Bryanskii OV, Syrchina AI, Semenov AA (1988). Chemical composition of a culture of tissue of Scorzonera hispanica. Chem Nat Compd 24: 655-655. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • Wang B, Li GQ, Qiu PJ, Guan HS (2007). Two new olean-type triterpene fatty esters from Scorzonera mongolica. Chin Chem Lett 18: 708-710. google scholar
  • Wu QX, Su YB, Zhu Y (2011). Triterpenes and steroids from the roots of Scorzonera austriaca. Fitoterapia 82: 493-496. google scholar
  • Xie Y, Guo QS, Wang GS (2016). Flavonoid glycosides and their derivatives from the herbs of Scorzonera austriaca Wild. Molecules 21: 803. google scholar
  • 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. google scholar
  • Zidorn C, Ellmerer-Müller EP, Stuppner H (2000). Tyrolobibenzyls - Novel secondery metabolites from Scorzonera humilis. HeIv Chim Acta 83: 2920-2925. google scholar

Citations

Copy and paste a formatted citation or use one of the options to export in your chosen format


EXPORT



APA

Çetin, B., Şahin, H., & Sarı, A. (2018). Triterpenoids from Scorzonera veratrifolia Fenzl. İstanbul Journal of Pharmacy, 48(2), 23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411


AMA

Çetin B, Şahin H, Sarı A. Triterpenoids from Scorzonera veratrifolia Fenzl. İstanbul Journal of Pharmacy. 2018;48(2):23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411


ABNT

Çetin, B.; Şahin, H.; Sarı, A. Triterpenoids from Scorzonera veratrifolia Fenzl. İstanbul Journal of Pharmacy, [Publisher Location], v. 48, n. 2, p. 23-37, 2018.


Chicago: Author-Date Style

Çetin, Betül, and Hasan Şahin and Aynur Sarı. 2018. “Triterpenoids from Scorzonera veratrifolia Fenzl.” İstanbul Journal of Pharmacy 48, no. 2: 23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411


Chicago: Humanities Style

Çetin, Betül, and Hasan Şahin and Aynur Sarı. Triterpenoids from Scorzonera veratrifolia Fenzl.” İstanbul Journal of Pharmacy 48, no. 2 (Jun. 2025): 23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411


Harvard: Australian Style

Çetin, B & Şahin, H & Sarı, A 2018, 'Triterpenoids from Scorzonera veratrifolia Fenzl', İstanbul Journal of Pharmacy, vol. 48, no. 2, pp. 23-37, viewed 4 Jun. 2025, https://doi.org/10.5152/IstanbulJPharm.2018.410411


Harvard: Author-Date Style

Çetin, B. and Şahin, H. and Sarı, A. (2018) ‘Triterpenoids from Scorzonera veratrifolia Fenzl’, İstanbul Journal of Pharmacy, 48(2), pp. 23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411 (4 Jun. 2025).


MLA

Çetin, Betül, and Hasan Şahin and Aynur Sarı. Triterpenoids from Scorzonera veratrifolia Fenzl.” İstanbul Journal of Pharmacy, vol. 48, no. 2, 2018, pp. 23-37. [Database Container], https://doi.org/10.5152/IstanbulJPharm.2018.410411


Vancouver

Çetin B, Şahin H, Sarı A. Triterpenoids from Scorzonera veratrifolia Fenzl. İstanbul Journal of Pharmacy [Internet]. 4 Jun. 2025 [cited 4 Jun. 2025];48(2):23-37. Available from: https://doi.org/10.5152/IstanbulJPharm.2018.410411 doi: 10.5152/IstanbulJPharm.2018.410411


ISNAD

Çetin, Betül - Şahin, Hasan - Sarı, Aynur. Triterpenoids from Scorzonera veratrifolia Fenzl”. İstanbul Journal of Pharmacy 48/2 (Jun. 2025): 23-37. https://doi.org/10.5152/IstanbulJPharm.2018.410411



TIMELINE


Accepted25.06.2018

LICENCE


Attribution-NonCommercial (CC BY-NC)

This license lets others remix, tweak, and build upon your work non-commercially, and although their new works must also acknowledge you and be non-commercial, they don’t have to license their derivative works on the same terms.


SHARE



Istanbul University Press aims to contribute to the dissemination of ever growing scientific knowledge through publication of high quality scientific journals and books in accordance with the international publishing standards and ethics. Istanbul University Press follows an open access, non-commercial, scholarly publishing.