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Biological Evaluation, Overpressured Layer Chromatography Separation, and Isolation of a New Acetylenic Derivative Compound from Prangos platychlaena ssp. platychlaena Fruit Essential Oils

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Summary

In the present work, fruits of Prangos platychlaena Boiss. ex Tchihat. ssp. platychlaena (Apiaceae) collected from eastern (sample A) and central (sample B) parts of Turkey were subjected to hydrodistillation to yield essential oils (EOs). The chemical composition of P. platychlaena ssp. platychlaena fruit oil was analyzed by gas chromatography—flame ionization detector (GC—FID) and gas chromatography—mass spectrometry (GC—MS) techniques. An unknown compound with m/z 178 [M]+ in high percentages was detected in both EOs (45.8% and 11.2% in samples A and B, respectively). Column chromatography on silica gel was subsequently followed by the sample A and yielded a new acetylenic derivative (1), which was characterized by spectroscopic techniques as (2S)- 3,5-nonadiyne-2-yl acetate. Samples A and B oils were characterized by a series of acetylenic derivatives like 3,5-nonadiyne (24.5% and 5.8% in A and B, respectively), (Z)-3,5-nonadiyne-7-ene (0.2% in A), and (E)-3,5-nonadiyne-7-ene (0.5% in A). Monoterpenes α-pinene (6.8% and 12.8%), α-phellandrene (0.1% and 17.1%), and β-phellandrene (4.2% and 22.4%) were found to be the major components in P. platychlaena ssp. platychlaena EOs in samples A and B, respectively. The components of P. platychlaena ssp. platychlaena EOs were separated on the overpressured layer chromatography (OPLC) plates, and the plates were subsequently subjected to direct-bioautography assays using three plant pathogens such as Colletotrichum acutatum, C. fragariae, and C. gloeosporioides; however, no antifungal activity was observed. Due to a high yield, sample A was evaluated for its repellent activity against female mosquito Aedes aegypti and attraction of sterile male Mediterranean fruit fly Ceratitis capitata. Sample A demonstrated good repellency against Ae. aegypti in human-based cloth patch bioassays and no attraction to C. capitata in short range bioassays.

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References

  1. K.H.C Baser, N. Kirimer, Nat. Vol. Essent. Oils 1 (2014) 1–50.

    Google Scholar 

  2. M.G. Pimenov, M.V. Leonov, Tur. J. Bot. 28 (2004) 139–145.

    Google Scholar 

  3. Y. Yesil, E. Akalin, J. Fac. Pharm. Istanbul 46 (2016) 23–37.

    Google Scholar 

  4. A. Dogan, G. Bulut, E. Tuzlacı, I. Senkardes, J. Fac. Pharm. Ist. Univ. 44 (2014) 251–262.

    Google Scholar 

  5. I. Kaval, L. Behcet, U. Cakilcioglu, J. Ethnopharmacol. 155 (2014) 171–184.

    Article  Google Scholar 

  6. G. Bulut, E. Tuzlacı, A. Dogan, I. Senkardes, J. Fac. Pharm. Ist. Univ. 44 (2014) 163–179.

  7. A. Uzel, T. Dirmenci, A. Celik, T. Arabaci, Chem. Nat. Comp. 42 (2006) 169–171.

    Article  CAS  Google Scholar 

  8. A. Ulubelen, G. Topcu, N. Tan, S. Olcal, C. Johansson, M. Ucer, H. Birman, S. Tamer, J. Ethnopharmacol. 45 (1995) 193–197.

    Article  CAS  Google Scholar 

  9. N. Kucukboyaci, F. Ayaz, N. Adiguzel, B. Bani, A.C. Goren, Nat. Prod. Com. 11 (2016) 1697–1700.

    Google Scholar 

  10. E. Tyihák, E. Mincsovics, H. Kalász, J. Chromatogr. 174 (1979) 75–81.

    Article  Google Scholar 

  11. E. Mincsovics, M. Garami, L. Kecskés, B. Tapa, Z. Végh, Gy. Kátay, E. Tyihák, J. AOAC Int. 82 (1999) 587–598.

    Article  CAS  Google Scholar 

  12. E. Tyihák, A.M. Móricz, E. Mincsovics, in: E. Tyihák (ed.), Forced Flow Layer Chromatography, Elsevier, Amsterdam, 2016, pp. 49–186.

    Chapter  Google Scholar 

  13. E. Tyihák, E. Mincsovics, in: Sz. Nyiredy (ed.), Planar Chromatography: A Retrospective View For The Third Millennium, Springer Scientific Publisher, Budapest, 2001, p. 137.

  14. N. Tabanca, R.S. Pawar, D. Ferreira, J.P. J. Marais, S.I. Khan, V. Jishi, D.E. Wedge, I.A. Khan, Planta Med. 73 (2007) 1107–1111.

    Article  CAS  Google Scholar 

  15. X. Wang, D.E. Wedge, N. Tabanca, R.D. Johnson, S.J. Cutler, P.F. Pace, B.J. Smith, L. Zhou, Nat. Prod. Commun. 3 (2008) 1079–1084.

    CAS  Google Scholar 

  16. E. Mincsovics, N. Tabanca, A.M. Móricz, D.E. Wedge, E. Tyihák, J. Planar Chromatogr. 23 (2010) 225–226.

    Article  CAS  Google Scholar 

  17. X. Wang, E. Habib, F. Leon, M.R. Radwan, N. Tabanca, J. Gao, D.E. Wedge, S.J. Cutler, Chem. Biodivers. 8 (2011) 2331–2340.

    Article  CAS  Google Scholar 

  18. E. Tyihák, E. Mincsovics, A.M. Móricz, J. Chromatogr. A 1232 (2012) 3–18.

    Article  Google Scholar 

  19. A. Altintas, N. Tabanca, E. Tyihák, P.G. Ott, A. M. Móricz, E. Mincsovics, D.E. Wedge, J. AOAC Int. 96 (2013) 1200–1208.

    Article  CAS  Google Scholar 

  20. A.M. Móricz, P.G. Ott, J. AOAC Int. 98 (2015) 850–856.

    Article  Google Scholar 

  21. A.M. Móricz, D. Krüzselyi, P.G. Ott, J. Planar Chromatogr. 30 (2017) 121–125.

    Article  Google Scholar 

  22. D.H. Hochmuth, in: D.H. Hochmuth (ed.), MassFinder-4, Hochmuth Scientific Consulting, Hamburg, 2008.

  23. R.P. Adams (ed.), Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, Allured Publishing Corporation, Carol Stream, IL, 2007.

  24. M.T.W. Hearn, Org. Magn. Resonance 9 (1977) 141–144.

    Article  CAS  Google Scholar 

  25. R.S. Chauhan, M.C. Nautiyal, A. Tava, M. Mella, Helv. Chim. Acta 95 (2012) 780–787.

    Article  CAS  Google Scholar 

  26. B. Adhikari, H.P. Devkota, K.R. Joshi, T. Watanabe, S. Yahara, Nat. Prod. Res. 30 (2016) 1577–1584.

    Article  CAS  Google Scholar 

  27. K.H. Posey, C.E. Schreck, Mosquito News 41 (1981) 566–568.

    Google Scholar 

  28. N. Tabanca, U.R. Bernier, N.M. Agramonte, M. Tsikolia, J.R. Bloomquist, Curr. Org. Chem. 20 (2016) 2690–2702.

    Article  CAS  Google Scholar 

  29. N.D. Epsky, J. Niogret, Nat. Volatiles Essent. Oil (in press).

  30. H. Noorizadeh, A. Farmany, M. Noorizadeh, Quím. Nova 34 (2011) 1398–1404.

    Article  CAS  Google Scholar 

  31. J.B. Boti, A. Bighelli, C. Cavaleiro, L. Salgueiro, J. Casanova, Flavour Fragr. J. 21 (2006) 268–273.

    Article  CAS  Google Scholar 

  32. A. Orav (ed.), Identification of Terpenes by Gas Chromatography–Mass Spectrometry, CRC Press, Boca Raton, FL, 2001.

  33. C.M. Bignell, P.J. Dunlop, J.J. Brophy, Flav. Fragr. J. 13 (1998) 131–139.

    Article  CAS  Google Scholar 

  34. J. Palá-Paúl, J. Brophy, R. Goldsack, B. Fontaniella, Biochem. Syst. Ecol. 32 (2004) 55–62.

    Article  Google Scholar 

  35. A. Maggio, S. Rosselli, M. Bruno, V. Spadaro, F.M. Raimondo, F. Senatore, Molecules 17 (2012) 10232–10241.

    Article  CAS  Google Scholar 

  36. A.-H. Al-Ja’ fari, R. Vila, B. Freixa, F. Tomi, J. Casanova, J. Costa, S. Cañigueral, Phytochemistry 72 (2011) 1406–1413.

    Article  Google Scholar 

  37. H. Noorizadeh, A. Farmany, J. Chinese Chem. Soc. 57 (2010) 1268–1277.

    Article  CAS  Google Scholar 

  38. J.F. Cavalli, F. Tomi, A.F. Bernardini, J. Casanova, Flavour Frag. J. 18 (2003) 532–538.

    Article  CAS  Google Scholar 

  39. I. Cheraif, H.B. Jannet, M. Hammami, M.L. Khouja, Z. Mighri, Biochem. Syst. Ecol. 35 (2007) 813–820.

    Article  CAS  Google Scholar 

  40. J.J. Brophy, R.J. Goldsack, A. Punruckvong, A.R. Bean, P.I. Forster, B.J. Lepschi, J.C. Doran, A.C. Rozefelds, Flavour Fragr. J. 15 (2000) 342–351.

    Article  CAS  Google Scholar 

  41. D.G. Crosby, N. Aharonson, Tetrahedron 23 (1967) 465–472.

    Article  CAS  Google Scholar 

  42. B. Tao, J.C. Ruble, D.A. Hoic, G.C. Fu, J. Am. Chem. Soc. 121 (1999) 5091–5092.

    Article  CAS  Google Scholar 

  43. https://www.epa.gov/minimum-risk-pesticides/conditions-minimum-risk-pesticides (assessed on September 1, 2017).

  44. P.E. Kendra, W.S. Montgomery, J. Niogret, E.Q. Schnell, M.A. Deyrup, N.E. Epsky, J. Pest Sci. 87 (2014) 681–689.

    Article  Google Scholar 

  45. P.E. Kendra, D. Owens, W.S. Montgomery, T.I. Narvaez, G.R. Bauchan, E.Q. Schnell, N. Tabanca, D. Carillo, PLos One 12 (2017) e0179416.

    Article  Google Scholar 

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Author information

Authors and Affiliations

  1. USDA-ARS, Subtropical Horticulture Research Station, Miami, 33158, FL, USA

    Nurhayat Tabanca & Nancy D. Epsky

  2. USDA-ARS, Natural Products Utilization Research Unit, University, 38677, MS, USA

    David E. Wedge

  3. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, 38677, MS, USA

    Xing-Cong Li

  4. Department of Chinese Herbal Chemistry, Beijing University of Chinese Medicine, Beijing, 100102, China

    Zengping Gao

  5. Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskisehir, 26470, Turkey

    Temel Ozek

  6. Turkey and Anadolu University, Medicinal Plant, Drug and Scientific Research Center (AUBIBAM), Eskisehir, 26470, Turkey

    Temel Ozek

  7. USDA-ARS, Center for Medical, Agricultural, and Veterinary Entomology, , Gainesville, FL, 32608, USA

    Ulrich R. Bernier

  8. Department of Pharmacognosy, Faculty of Pharmacy, Near East University, Lefkosa (Nicosia) TRNC, 10, Mersin, Turkey

    K. Husnu Can Baser

  9. Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskisehir, 26470, Turkey

    Gulmira Ozek

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  1. Nurhayat Tabanca
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  2. David E. Wedge
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  3. Xing-Cong Li
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  4. Zengping Gao
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  7. Nancy D. Epsky
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  8. K. Husnu Can Baser
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  9. Gulmira Ozek
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Correspondence to Nurhayat Tabanca or Gulmira Ozek.

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Tabanca, N., Wedge, D.E., Li, XC. et al. Biological Evaluation, Overpressured Layer Chromatography Separation, and Isolation of a New Acetylenic Derivative Compound from Prangos platychlaena ssp. platychlaena Fruit Essential Oils. JPC-J Planar Chromat 31, 61–71 (2018). https://doi.org/10.1556/1006.2018.31.1.8

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  • DOI: https://doi.org/10.1556/1006.2018.31.1.8

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