Skip to main content
SpringerLink
Log in

Synthesising a novel derivatives of piperine from black pepper (Piper nigrum L.)

  • Original Paper
  • Published:
Journal of Food Measurement and Characterization Aims and scope Submit manuscript

Abstract

Black pepper (Piper nigrum L.) has gained a global consideration because of its volume in the spice industry. This plant has shown great potential for having medical applications and novel biologically active compounds. In black pepper, natural lipophilic amide piperine was isolated. Piperine was isolated from the fruit using glacial acetic acid as solvent. After isolation and characterization of piperine were done, then it is used to prepare new and novel derivatives of piperine through the experimental procedure. The derivatives of piperine were synthesized by condensation of piperic acid with different substituted aromatic amines, to make a new derivative of piperine, such as ((2E, 4E)-5-(1,3-benzodioxol-5-yl)-N-(1,3-benzothiazol-2-yl)penta-2,4-dienamide) and a novel derivative ((2E, 4E)-5-(1,3-benzodioxol-5-yl)-N-(1,3-benzothiazol-2-yl)penta-2,4-dienehydrazide). The structure of piperine and the derivatives were elucidated through a combination of spectrometric techniques, including ultraviolet spectrophotometer, Mass spectrometry Fourier transform infrared spectroscopy, proton nuclear magnetic resonance.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. R.K. Saxena, P. Venkaiah, L. Anitha, R.M. Venu, Int. J. Food Sci. Nutr. 58, 250–260 (2007)

    Article  CAS  Google Scholar 

  2. S. Hartwig, B. Malgorzata, Q. Rolf, S. Wolfgang, L. Gerd, J. Agric. Food Chem. 53, 3358–3363 (2005)

    Article  Google Scholar 

  3. A.C. Nisar, F. Hina, H.A. Bilal, F. Shahid, A. Mohammad, A.K. Mubarak, Asian Pac. J. Trop. Biomed. 2, S1945–S1953 (2012)

    Article  Google Scholar 

  4. T. Jagella, W. Grosch, Eur. Food Res. Technol. 2091, 22–26 (1999)

    Article  Google Scholar 

  5. M. Meghwal, T.K. Goswami, Open Access Scientific Reports 1, 129 (2012). doi:10.4172/scientificreports.129

    Google Scholar 

  6. U. Parimi, D. Kolli, V.R.V. Durvasula, Med. Chem. Res. 22, 5466–5471 (2013)

    Article  Google Scholar 

  7. I. Gulcin, Int. J. Food Sci. Nutr. 56, 491–499 (2005)

    Article  Google Scholar 

  8. Y. Liu, V.R. Yadev, B.B. Aggarwal, M.G. Nair, Nat. Prod. Commun. 5, 1253–1257 (2010)

    Article  Google Scholar 

  9. H.J. Dorman, S. Deans, J. Appl. Microbiol. 88, 308–316 (2000)

    Article  CAS  Google Scholar 

  10. M. Vachana, J.P. Samuel, K. Geema, P.S. Evan, KhR Mahaboob, Inflammation 35, 1348–1356 (2012)

    Article  Google Scholar 

  11. R. El-Hamas, M. Idaomar, A. Alonso-Moraga, S.A. Munoz, Food Chem. Toxicol. 41, 41–47 (2003)

    Article  Google Scholar 

  12. G.A. Agbor, J.A. Vinson, J.E. Oben, J.Y. Ngogang, Nutr. Res. 12, 659–663 (2006)

    Article  Google Scholar 

  13. E.S. Sunila, G. Kuttan, J. Ethnopharmacol. 90, 339–346 (2004)

    Article  CAS  Google Scholar 

  14. O. Dong-yun, Z. Long-hui, P. Hao, X. Li-hui, W. Yao, L. Kun-peng, H. Xian-hui, Food Chem. Toxicol. 60, 424–430 (2013)

    Article  Google Scholar 

  15. R.S. Vijayakumar, D. Surya, N. Nalini, Redox Rep. 9, 105–110 (2004)

    Article  CAS  Google Scholar 

  16. N. Pathak, S. Khandlewal, Eur. J. Pharmacol. 576, 160–170 (2007)

    Article  CAS  Google Scholar 

  17. C.R. Pradeep, G. Kuttan, Clin. Exp. Metastasis 19, 703–708 (2002)

    Article  CAS  Google Scholar 

  18. S. Panda, A. Kar, Hormon. Metab. Res. 35(9), 523–526 (2003)

    Article  CAS  Google Scholar 

  19. N. Pathak, S. Khandelwalm, Environ. Toxicol. Pharmacol. 28, 52–60 (2009)

    Article  CAS  Google Scholar 

  20. K. Srinivasan, Food Res. Int. 38, 77–86 (2005)

    Article  CAS  Google Scholar 

  21. D. Acharaporn, I. Kornkanok, P. Sakonwun, L. Nanteetip, J. Nat. Med. 67, 303–310 (2013)

    Article  Google Scholar 

  22. M.H. Mehmood, A.H. Gilani, J. Med. Food 13, 1086–1096 (2010)

    Article  CAS  Google Scholar 

  23. R.A. Clery, C.J. Hammond, A.C. Wright, J. Essent. Oil Res. 18, 1–3 (2006)

    Article  CAS  Google Scholar 

  24. V. Badmaev, M. Majeed, P.N. Edward, Nutr. Res. 19, 381–388 (1999)

    Article  CAS  Google Scholar 

  25. B. Vladimir, M. Muhammed, P. Lakshmi, J. Nutr. Biochem. 11(2), 109–113 (2000)

    Article  Google Scholar 

  26. R.K. Bhardwaj, H. Glaesser, L. Becquemont, U. Klotz, S.K. Gupta, M.F. Fromm, J. Pharmacol. Exp. Ther. 302, 645–650 (2002)

    Article  CAS  Google Scholar 

  27. R.S. Vijayakumar, N. Nalini, J. Food Biochem. 30, 405–421 (2006)

    Article  CAS  Google Scholar 

  28. T. Velpandian, R. Jasuja, R.K. Bhardwaj, J. Jaiswal, S.K. Gupta, Eur. J. Drug Metab. Pharmacokinet. 26, 241–247 (2001)

    Article  CAS  Google Scholar 

  29. T. Anette, B. Carin, W. Tina, E. Stéphane, S. Ankie, F. Markus, B. Paul, Food Chem. Toxicol. 66, 350–357 (2014)

    Article  Google Scholar 

  30. P.V. Srinivas, J.M. Rao, Phytochemistry 52, 957–958 (1999)

    Article  CAS  Google Scholar 

  31. R. Capasso, A.A. Izzo, F. Borrelli, A. Russo, L. Sautebin, A. Pinto, F. Capasso, N. Mascolo, Life Sci. 71, 2311–2317 (2002)

    Article  CAS  Google Scholar 

  32. K.V. Padalkar, V.G. Gaikar, Sep. Sci. Technol. 43(12–11), 3097–3118 (2008)

    Article  CAS  Google Scholar 

  33. S.R. Sachin, K.R. Virendra, Ind. Crops Prod. 58, 259–264 (2014)

    Article  Google Scholar 

  34. C. Perakis, V. Louli, K. Magoulas, J. Food Eng. 71(4), 386–393 (2005)

    Article  Google Scholar 

  35. A.C. Kumoro, S. Harcharan, H. Masitah, Chin. J. Chem. Eng. 17(6), 1014–1020 (2009)

    Article  CAS  Google Scholar 

  36. A.B. Wood, L.B. Maureen, D.J. James, Flavour Fragr. J. 3, 55–64 (1988)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank technical staff of Chemistry Department at Raparin University and Jamia Hamdard (Hamdard University) to let do the practical work in their chemical laboratories. This work was financed with grants from HCDP programme in Ministry of Higher Education and Scientific Research of Kurdistan – Iraq.

Conflict of interest

The authors declare that they have no conflict of interest. This article does not contain any studies with human or animal subjects.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Raparin, Rania, Kurdistan Region, Iraq

    Dara Muhammed Aziz & Jawameer Rasool Hama

  2. Department of Chemistry, Faculty of Science, Jamia Hamdard (Hamdard University), New Delhi, 110 062, India

    Sarwar M. Alam

Authors
  1. Dara Muhammed Aziz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jawameer Rasool Hama
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sarwar M. Alam
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dara Muhammed Aziz.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aziz, D.M., Hama, J.R. & Alam, S.M. Synthesising a novel derivatives of piperine from black pepper (Piper nigrum L.). Food Measure 9, 324–331 (2015). https://doi.org/10.1007/s11694-015-9239-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11694-015-9239-2

Keywords

Search

Navigation