New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

COŞKUNÇELEBİ, Kamil; Makbul, Serdar; ERİK, İshak

doi:10.3906/kim-2009-17

New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

Ishak ERIK, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Trabzon, Türkiye)

Kamil COŞKUNÇELEBİ, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Biyoloji Bölümü, Trabzon, Türkiye)

Serdar MAKBUL (Recep Tayyip Erdoğan Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Rize, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2021 Cilt: 45 Sayı: 1 Sayfa Aralığı: 199 - 209 Metin Dili: İngilizce DOI: 10.3906/kim-2009-17 İndeks Tarihi: 28-06-2022

New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

Öz:

Chromatographic separation of n-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of the Scorzonera aucheriana DC collected from Sivas province of Turkey yielded nine natural compounds; two new 3-caffeoyl-quinic acid analogs (1-2), one new taraxasterol oleate (3), and six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6),lupeol (7), lupeol acetate (8), and β-sitosterol (9) were characterized. The structures of the isolated compounds were elucidated on the basis of NMR (1H, 13C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.

Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Kamelin RV, Tagaev IU. Survey of species of the genus Scorzonera (Asteracea). Botanical Journal 1986; 71: 1672-1682.
2. Chamberlain DF. Scorzonera L. In: Davis PH (editors). Flora of Turkey and East Aegean Island. Edinburg, UK: Edinburg University Press, 1975, pp. 632-657.
3. Zaika MA, Kilian N, Jones K, Krinitsina AA, Nilova MV et al. Scorzonera sensu lato (Asteraceae, Cichorieae)–taxonomic reassessment in the light of new molecular phylogenetic and carpological analyses. PhytoKeys 2020; 137: 1-85.
4. Coşkunçelebi K, Makbul S, Gültepe M, Okur S, Güzel ME. A conspectus of Scorzonera s.l. in Turkey. Turkish Journal of Botany 2015; 39 (2): 76-87.
5. Baytop T. Türkiye’de bitkiler ile tedavi: geçmişte ve bugün. Ankara, Turkey: Nobel Tıp Kitabevleri, 1999.
6. Şenkardeş I, Bulut G, Doğan A, Tuzlacı E. An ethnobotanical analysis on the wild edible plants of Turkish Astreaceae Taxa. Agriculturae Conspectus Scientificus 2019; 84(1): 17-28.
7. Akkol EK, Acıkara OB, Süntar I, Citoğlu GS, Keleş H et al. Enhancement of wound healing by topical application of Scorzonera species: Determination of the constituents by HPLC with new validated reverse phase method. Journal of Ethnopharmacology 2011; 137 (2): 1018- 1027.
8. Acıkara ÖB, Çitoğlu GS, Dall’Acqua S, Šmejkal K, Cvačka J et al. A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC. Natural Product Research 2012; 26 (20): 1892-1897.
9. Akkol EK, Acıkara ÖB, Süntar I, Ergene B, Çitoğlu GS. Ethnopharmacological evaluation of some Scorzonera species: in vivo antiinflammatory and antinociceptive effects. Journal of Ethnopharmacology 2012; 140 (2): 261-270.
10. Bahadır Ö, Çitoğlu GS, Šmejkal K, Dall’Acqua S, Özbek H et al. Analgesic compounds from Scorzonera latifolia (Fisch. and Mey.) DC. Journal of Ethnopharmacology 2010; 131 (1): 83-87.
11. Çitoğlu GS, Bahadir Ö, Dall’Acqua S. Dihydroisocoumarin derivatives isolated from the roots of Scorzonera latifolia. Turkish Journal of Pharmaceutical Sciences 2010; 7 (3): 205-212
12. Wang B, Li G, Guan H, Yang L, Tong G. A new erythrodiol triterpene fatty ester from Scorzonera mongolica. Acta Pharmaceutica Sinica 2009; 44 (11): 1258-1261.
13. Wang B, Qiu P, Li G, Qu Y. Anti-tumor constituents from Scorzonera mongolica. Chinese Journal of Natural Medicines 2009; 7 (4): 283- 286.
14. Wang B, Yang L, LI G-q, GUAN H-s, TONG G-z. Antitumor triterpenes from Scorzonera mongolica Maxim. Chinese Pharmaceutical Journal 2010; 10: 005.
15. Tsevegsuren N, Edrada R, Lin W, Ebel R, Torre C et al. Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. Journal of Natural Products 2007; 70 (6): 962-967.
16. Paraschos S, Magiatis P, Kalpoutzakis E, Harvala C, Skaltsounis A-L. Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica. Journal of Natural Products 2001; 64 (12): 1585-1587.
17. Zidorn C, Ellmerer-Müller E, Stuppner H. Sesquiterpenoids from Scorzonera hispanica L. Die Pharmazie 2000; 55 (7): 550.
18. Zidorn C, Ellmerer‐Müller EP, Stuppner H. Tyrolobibenzyls–novel secondary metabolites from Scorzonera humilis. Helvetica Chimica Acta 2000; 83 (11): 2920-2925.
19. Zidorn C, Ellmerer EP, Sturm S, Stuppner H. Tyrolobibenzyls E and F from Scorzonera humilis and distribution of caffeic acid derivatives, lignans and tyrolobibenzyls in European taxa of the subtribe Scorzonerinae (Lactuceae, Asteraceae). Phytochemistry 2003; 63 (1): 61-67.
20. Sareedenchai V, Zidorn C. Flavonoids as chemosystematic markers in the tribe Cichorieae of the Asteraceae. Biochemical Systematics and Ecology 2010; 38 (5): 935-957.
21. Wang Y, Wray V, Tsevegsuren N, Lin W, Proksch P. Phenolic compounds from the Mongolian medicinal plant Scorzonera radiata. Zeitschrift für Naturforschung C 2012; 67 (3-4): 135-143.
22. Khobrakova V, Nikolaev S, Tolstikhina V, Semenov A. Immunomodulating properties of lignan glucoside from cultivated cells of Scorzonera hispanica L. Pharmaceutical Chemistry Journal 2003; 37 (7): 345-346.
23. Zidorn C, Spitaler R, Ellmerer-Müller E-P, Perry NB, Gerhäuser C et al. Structure of tyrolobibenzyl D and biological activity of tyrolobibenzyls from Scorzonera humilis. Zeitschrift für Naturforschung C 2002; 57 (7-8): 614-619.
24. Panche A, Diwan A, Chandra S. Flavonoids: an overview. Journal of Nutritional Science 2016; 5: 1-15.
25. Pauli GF, Poetsch F, Nahrstedt A. Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques. Phytochemical Analysis 1998; 9 (4): 177-185.
26. Lin LC, Kuo YC, Chou CJ. Immunomodulatory principles of Dichrocephala bicolor. Journal of Natural Products 1999; 62 (3): 405-408.
27. Sari A, Sahin H, Ozsoy N, Ozbek CB. Phenolic compounds and in vitro antioxidant, anti-inflammatory, antimicrobial activities of Scorzonera hieraciifolia Hayek roots. South African Journal of Botany 2019; 125: 116-119.
28. Sahin H, Sari A, Ozsoy N, Ozbek CB, Koyuncu O. Two new phenolic compounds and some biological activities of Scorzonera pygmaea Sibth. & Sm. subaerial parts. Natural Product Research 2020; 34 (5): 621-628.
29. Yang Y, Liu X, Wu H, He X, Bi Y et al. Radical scavenging activity and cytotoxicity of active quinic acid derivatives from Scorzonera divaricata roots. Food Chemistry 2013; 138 (2-3): 2057-2063.
30. Wang Y, Wray V, Tsevegsuren N, Lin W, Proksch P. Phenolic compounds from the Mongolian medicinal plant Scorzonera radiate. Zeitschrift fuer Naturforschung C: Journal of Biosciences 2012; 67 (3/4): 135-143.
31. Jehle M, Bano J, Ellmerer EP, Zidorn C. Natural products from Scorzonera aristata (Asteraceae). Natural Product Communications 2010; 5 (5): 725-727.
32. Bahadir AO, Saltan IG, Smejkal K, Hosek J, Smejkal K et al. Turkish Scorzonera species extracts attenuate cytokine secretion via inhibition of NF-κB activation, showing anti-inflammatory effect in vitro. Molecules 2015; 21 (1): E43.
33. Sari A. Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC. Natural Product Research 2012; 26 (1): 50-55.
34. Sari A. Two new 3-benzylphthalides from Scorzonera veratrifolia Fenzl. Natural Product Research 2010; 24 (1): 56-62.
35. Elias V, Simoneit BT, Pereira AS, Cabral JA, Cardoso JN. Detection of high molecular weight organic tracers in vegetation smoke samples by high-temperature gas chromatography-mass spectrometry. Environmental Science and Technology 1999; 33 (14): 2369-2376.
36. Sun H, Chen D, Zhang L, Wen X. Pentacyclic triterpene as cholesteryl ester transfer protein inhibitor and its preparation. PCT International Applications. 2016; WO 2016086453 A1 20160609.
37. Sun H, Chen D, Zhang L, Wen X. Pentacyclic triterpene as cholesteryl ester transfer protein inhibitor and its preparation. Faming Zhuanli Shenqing 2015; CN 104725456 A 20150624.
38. Kweifio-Okai G. Triterpene compounds having antiinflammatory and antiarthritic activity. PCT International Applications 1993; WO 9309129 A1 19930513.
39. Khalilov LM, Khalilova AZ, Shakurova ER, Nuriev IF, Kachala VV et al. PMR and 13C NMR Spectra of Biologically Active Compounds. XII. Taraxasterol and its acetate fom the aerial part of Onopordum acanthiu. Chemistry of Natural Compounds 2003; 39: 285-288.
40. Egharevba1 HO, Okwute SK, Okogun JI, Goli JI. A Bioactive triterpene from Laggera pterodonta (Asteraceae) (DC.) Nigerian Journal of Chemical Research 2009; 14 (13-14): 2008-2009.
41. Menichini F, Di Benedetto R, Delle Monache F. A triterpene epoxide and a guaianolide from Ptilostemmon gnaphaloides. Phytochemistry 1996; 41 (5): 1377.-1379.
42. Aratanechemuge Y, Hibasami H, Sanpin K, Katsuzaki H, Imai K et al. Induction of apoptosis by lupeol isolated from Mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells. Oncology Reports 2004; 11 (2): 289-292.
43. Jamal AK, Yaacob WA, Din LB. A chemical study on Phyllanthus reticulate. Journal of Physical Science 2008; 19 (2): 45–50.
44. Marzieh MY, Seyed HRA. New triterpenoids from Peucedanum ruthenicum. Iranian Journal of Pharmaceutical Sciences Autumn 2008; 4 (4): 289-294.
45. Yang Y, Yao J, Jin X, Shi Z, Shen T et al. Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata, Phytochemistry 2016; 124: 86-98. 46. Wu Q, Su Y, Zhu Y. Triterpenes and steroids from the roots of Scorzonera austriaca. Fitoterapia 2011; 82 (3): 493-496.
47. Wang B, Yang L, Li G, Guan H, Tong G. Antitumor triterpenes from Scorzonera mongolica Maxim. Zhongguo Yaoxue Zazhi 2010; 45 (10): 727-732.
48. Wang B, Li G, Guan H, Yang L, Tong G. Two new erythrodiol triterpene fatty esters from Scorzonera mongolica. Yaoxue Xuebao 2009; 44 (11): 1258-1261.
49. Wang B, Qiu P, Li G, Qu Y. Anti-tumor constituents from Scorzonera mongolica. Zhongguo Tianran Yaowu 2009; 7 (4): 283-286.
50. Harkati B, Akkal S, Bayat C, Laouer H, Franca MG et al. Secondary metabolites from Scorzonera undulata ssp. deliciosa (Guss.) Maire (Asteracae) and their antioxidant activities. Records of Natural Products 2010; 4 (3): 171-175.
51. Wang B, Li G, Qiu P, Guan H. Two new olean-type triterpene fatty esters from Scorzonera mongolica. Chinese Chemical Letters 2007; 18 (6): 708-710.
52. Brahim H, Salah A, Bayet C, Laouer H, Dijoux-Franca MG. Evaluation of antioxidant activity, free radical scavenging and cuprac of two compounds isolated from Scorzonera undulata ssp. deliciosa. Advances in Environmental Biology 2013; 7 (4): 591-594.
53. Bahadir-Acikara O, Ozbilgin S, Saltan-Iscan G, Dall’Acqua S, Rjaskova V et al. Phytochemical analysis of Podospermum and Scorzonera n-hexane extracts and the HPLC quantitation of triterpenes. Molecules 2018; 23 (7): 1813.

APA	ERİK İ, COŞKUNÇELEBİ K, Makbul S (2021). New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. , 199 - 209. 10.3906/kim-2009-17
Chicago	ERİK İshak,COŞKUNÇELEBİ Kamil,Makbul Serdar New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. (2021): 199 - 209. 10.3906/kim-2009-17
MLA	ERİK İshak,COŞKUNÇELEBİ Kamil,Makbul Serdar New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. , 2021, ss.199 - 209. 10.3906/kim-2009-17
AMA	ERİK İ,COŞKUNÇELEBİ K,Makbul S New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. . 2021; 199 - 209. 10.3906/kim-2009-17
Vancouver	ERİK İ,COŞKUNÇELEBİ K,Makbul S New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. . 2021; 199 - 209. 10.3906/kim-2009-17
IEEE	ERİK İ,COŞKUNÇELEBİ K,Makbul S "New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana." , ss.199 - 209, 2021. 10.3906/kim-2009-17
ISNAD	ERİK, İshak vd. "New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana". (2021), 199-209. https://doi.org/10.3906/kim-2009-17

APA	ERİK İ, COŞKUNÇELEBİ K, Makbul S (2021). New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. Turkish Journal of Chemistry, 45(1), 199 - 209. 10.3906/kim-2009-17
Chicago	ERİK İshak,COŞKUNÇELEBİ Kamil,Makbul Serdar New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. Turkish Journal of Chemistry 45, no.1 (2021): 199 - 209. 10.3906/kim-2009-17
MLA	ERİK İshak,COŞKUNÇELEBİ Kamil,Makbul Serdar New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. Turkish Journal of Chemistry, vol.45, no.1, 2021, ss.199 - 209. 10.3906/kim-2009-17
AMA	ERİK İ,COŞKUNÇELEBİ K,Makbul S New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. Turkish Journal of Chemistry. 2021; 45(1): 199 - 209. 10.3906/kim-2009-17
Vancouver	ERİK İ,COŞKUNÇELEBİ K,Makbul S New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana. Turkish Journal of Chemistry. 2021; 45(1): 199 - 209. 10.3906/kim-2009-17
IEEE	ERİK İ,COŞKUNÇELEBİ K,Makbul S "New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana." Turkish Journal of Chemistry, 45, ss.199 - 209, 2021. 10.3906/kim-2009-17
ISNAD	ERİK, İshak vd. "New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana". Turkish Journal of Chemistry 45/1 (2021), 199-209. https://doi.org/10.3906/kim-2009-17