Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities

doi:10.1007/s13659-020-00259-9

应用天然产物 ›› 2020, Vol. 10 ›› Issue (5): 307-316.DOI: 10.1007/s13659-020-00259-9

Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities

Mohammad Sanad Abu-Darwish^1,2, Célia Cabral^3,4,5, Zulfigar Ali², Mei Wang², Shabana I. Khan², Melissa R. Jacob², Surendra K. Jain², Babu L. Tekwani², Fazila Zulfiqar², Ikhlas A. Khan², Hatem Taifour⁶, Lígia Salgueiro⁷, Thomas Efferth⁸

1 Department of Basic and Applied Sciences, Al-Balqa Applied University, Al-Salt 19117, Jordan;
2 National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA;
3 Coimbra Institute for Clinical and Biomedical Research(iCBR), Faculty of Medicine, University of Coimbra, 3000-548 Coimbra, Portugal;
4 Center for Innovative Biomedicine and Biotechnology(CIBB), University of Coimbra, 3000-548 Coimbra, Portugal

收稿日期:2020-07-29 修回日期:2020-08-01 出版日期:2020-10-24 发布日期:2020-10-23
通讯作者: Célia Cabral
基金资助:
This work has been conducted during the Fulbright visiting scholarship awarded to Prof. Dr. Mohammad Sanad Abu-Darwish during his Sabbatical leave from Al-Balqa’ Applied University, Al-Salt, Jordan, at the National Center for Natural Products Research, School of Pharmacy, University of Mississippi, USA. The authors thank the Dean of Scientific Research, Al-Balqa Applied University, Jordan, the Binational Fulbright Commission in Jordan, Council for International Exchange of Scholars (CIES), and Institute of International Education (IIE), USA. This work was also supported by Foundation for Science and Technology (FCT), Portugal (Strategic Projects UID/NEU/04539/2013, and UID/NEU/04539/2019, UIDB/04539/2020 and UIDP/04539/2020 (CIBB)).

Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities

1 Department of Basic and Applied Sciences, Al-Balqa Applied University, Al-Salt 19117, Jordan;
2 National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA;
3 Coimbra Institute for Clinical and Biomedical Research(iCBR), Faculty of Medicine, University of Coimbra, 3000-548 Coimbra, Portugal;
4 Center for Innovative Biomedicine and Biotechnology(CIBB), University of Coimbra, 3000-548 Coimbra, Portugal

Received:2020-07-29 Revised:2020-08-01 Online:2020-10-24 Published:2020-10-23
Contact: Célia Cabral
Supported by:
This work has been conducted during the Fulbright visiting scholarship awarded to Prof. Dr. Mohammad Sanad Abu-Darwish during his Sabbatical leave from Al-Balqa’ Applied University, Al-Salt, Jordan, at the National Center for Natural Products Research, School of Pharmacy, University of Mississippi, USA. The authors thank the Dean of Scientific Research, Al-Balqa Applied University, Jordan, the Binational Fulbright Commission in Jordan, Council for International Exchange of Scholars (CIES), and Institute of International Education (IIE), USA. This work was also supported by Foundation for Science and Technology (FCT), Portugal (Strategic Projects UID/NEU/04539/2013, and UID/NEU/04539/2019, UIDB/04539/2020 and UIDP/04539/2020 (CIBB)).

摘要/Abstract

摘要： In Jordan, Salvia ceratophylla L. is traditionally used in the treatment of cancer, microbial infections, and urinary disorders. This study aimed:(1) to chemically characterize S. ceratophylla essential oil (EO) from South Jordan, by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS); and (2) to evaluate in vitro the cytotoxic, anti-inflammatory, and antiprotozoal activities of the EO, it's predominant components, and the hexane (A), ethyl acetate (B), methanol (C) and crude-methanol extracts (D). The analysis revealed that the EO has 71 compounds, with linalool (54.8%) as main constituent. Only the hexane extract (A) showed some cytotoxic activity against SK-MEL, KB, BT-549, SK-OV-3, LLC-PK1 and VERO cells lines with IC 50 between 60 and > 100 μg/mL. The EO inhibited NO production (IC₅₀ 90 μg/mL) and NF-κB activity (IC₅₀ 38 μg/mL). The extracts A, B, and D inhibited NO production and NF-κB activity with IC₅₀ between 32 and 150 μg/mL. Linalool considerably inhibited NO production (IC₅₀ 18 μg/mL). The extracts tested did not exhibit antileishmanial activity. Regarding antitrypanosomal activity, the EO exhibited significant results with IC₅₀ 2.65 μg/mL. In conclusion, Jordan S. ceratophylla EO represents a rich source of linalool and bears a promising therapeutic potential for further antitrypanosomal drug development.

关键词: Lamiaceae, Essential oil, Chemical composition, Cytotoxicity, Anti-inflammatory activity, Neglected diseases

Abstract: In Jordan, Salvia ceratophylla L. is traditionally used in the treatment of cancer, microbial infections, and urinary disorders. This study aimed:(1) to chemically characterize S. ceratophylla essential oil (EO) from South Jordan, by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS); and (2) to evaluate in vitro the cytotoxic, anti-inflammatory, and antiprotozoal activities of the EO, it's predominant components, and the hexane (A), ethyl acetate (B), methanol (C) and crude-methanol extracts (D). The analysis revealed that the EO has 71 compounds, with linalool (54.8%) as main constituent. Only the hexane extract (A) showed some cytotoxic activity against SK-MEL, KB, BT-549, SK-OV-3, LLC-PK1 and VERO cells lines with IC 50 between 60 and > 100 μg/mL. The EO inhibited NO production (IC₅₀ 90 μg/mL) and NF-κB activity (IC₅₀ 38 μg/mL). The extracts A, B, and D inhibited NO production and NF-κB activity with IC₅₀ between 32 and 150 μg/mL. Linalool considerably inhibited NO production (IC₅₀ 18 μg/mL). The extracts tested did not exhibit antileishmanial activity. Regarding antitrypanosomal activity, the EO exhibited significant results with IC₅₀ 2.65 μg/mL. In conclusion, Jordan S. ceratophylla EO represents a rich source of linalool and bears a promising therapeutic potential for further antitrypanosomal drug development.

Key words: Lamiaceae, Essential oil, Chemical composition, Cytotoxicity, Anti-inflammatory activity, Neglected diseases

Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities[J]. 应用天然产物, 2020, 10(5): 307-316.

参考文献

1. H. Taifour, A. El-Oqlah, Jordan plant red list, vol. 1 (Royal Botanic Garden, Jordan, 2015)
2. S.A. Oran, Int. J. Biodiv. Cons. 6, 28-40 (2014)
3. N. Gürsoy, B. Tepe, H.A. Akpulat, Rec. Nat. Prod. 6, 278-287 (2012)
4. A. Al-Bakri, G. Othman, F. Afifi, F. Pharmacog, Mag. 6, 264-270 (2010)
5. V. Kasabri, F.U. Afifi, R. Abu-Dahab, N. Mhaidat, Y.K. Bustanji, I.M. Abaza, S. Mashallah, Rev. Roum. Chim. 59, 693-705 (2014)
6. M.B. Shehadeh, S. Sosa, G. Suaifan, R.M. Darwish, Jordan J. Pharm. Sci. 7, 153-161 (2014)
7. V. Cardile, A. Russo, C. Formisano, D. Rigano, F. Senatore, N.A. Arnold, F. Piozzi, J. Ethnopharmacol. 126, 265-272 (2009)
8. M.S. Abu-Darwish, Int. J. Phytomed. 6, 384-390 (2014)
9. J. Bero, M. Frédérich, J. Quetin-Leclercq, J. Phar. Pharmacol. 61, 1401-1433 (2009)
10. A. Tosun, S. Khan, Y.S. Kim, Á. Calín-Sánchez, X. Hysenaj, A. Carbonell-Barrachina, Trop. J. Pharm. Res. 13, 937-942 (2014)
11. T.A. Mokoka, S. Zimmermann, T. Julianti, Y. Hata, N. Moodley, M. Cal, M. Adams, M. Kaiser, R. Brun, N. Koorbanally, M. Hamburger, Planta Med. 77, 1663-1667 (2011)
12. M. Mohammadi, M. Yousefi, Z. Habibi, S. Rahmati, G. Imanzadeh, J. Ess. Oil Bear. Plants 13, 774-778 (2010)
13. E. Bağci, A. Koçak, Sci. Eng. J. Fırat. Univ. 19, 435-442 (2007)
14. K.H.C. Başer, H.G. Ağalar, F. Celep, A. Kahraman, M. Doğan, B. Demirci, B. Turk, J. Pharm. Sci. 12, 53-58 (2015)
15. H.I. Al-Jaber, Jordan J. Chem. 11, 108-119 (2016)
16. R. Abu-Dahab, F. Afifi, V. Kasabri, L. Majdalawi, R. Naffa, Pharmac. Mag. 8, 319-324 (2012)
17. M.R. Loizzo, M. Abouali, P. Salehi, A. Sonboli, M. Kanani, F. Menichini, R. Tundis, R. Nat, Prod. Res. 24, 2278-2285 (2014)
18. I. Orhan, M. Kartal, Q. Naz, A. Ejaz, G. Yilmaz, Y. Kan, B. Konuklugil, B. Sener, M.I. Choudhary, Food Chem. 103, 1247-1254 (2007)
19. A.T. Peana, P.S. D'Aquila, F. Panin, G. Serra, P. Pippia, M.D.L. Moretti, Phytomedicine 9, 721-726 (2002)
20. G.P.P. Kamatou, N.P. Makunga, W.P.N. Ramogola, A.M. Viljoen, J. Ethnopharmacol. 119, 664-672 (2008)
21. N.L. Montesino, M. Kaiser, R. Brun, T.J. Schmidt, Molecules 20, 14118-14138 (2015)
22. M.V.O.B. De Alencar, J.M. Castroe Sousa, H.M.L. Rolim, M.G.F. Medeiros, G.S. Cerqueira, F.R.C. Almeida, A.M.G.L. Citó, P.M.P. Ferreira, J.A.D. Lopes, A.A.C. Melo-Cavalcante, M.T. Islam, Phytother. Res. 31, 175-201 (2017)
23. M. Serakta, Z. Djerrou, H. Mansour-Djaalab, F. KahloucheRiachi, S. Hamimed, W. Trifa, A. Belkhiri, N. Edikra, Y. Hamdi Pacha, Afr. J. Tradit. Complement. Altern. Med. 10, 427-430 (2013)
24. M.S.S. Rosa, R.R. Mendonca-Filho, H.R. Bizzo, I.A. Rodrigues, R.M.A. Soares, T. Souto-Padrón, C.S. Alviano, A.H. Lopes, Antimicrob. Agents Chemother. 47, 1895-1901 (2003)
25. M. Morales, M.C. Navarro, J. Martín, A. Valero, A.M. Lara, S. Barón, F. Morillas, Rev. Ibero-Latinoamericana Paras. 68(1), 65-72 (2009)
26. A.O. Santos, T. Ueda-Nakamura, B.P. Dias, V.F. Veiga, A.C. Pinto, C.V. Nakamura, J. Ethnopharmacol. 120, 204-208 (2008)
27. E. Nibret, M. Wink, Phytomedicine 17, 911-920 (2010)
28. Council of Europe, European pharmacopoeia, 3rd edn. (Council of Europe, Strasbourg, 1997)
29. N.W. Davies, J. Chromatogr. A 503, 1-24 (1990)
30. E. Borenfreund, H. Babich, N. Martin-Alguacil, vitro Cell. Dev. Biol. 26, 1030-1034 (1990)
31. A.M. Taweel, A.M. El-Shafae, S. Perveen, G.A. Fawzy, S.I. Khan, Int. J. Pharm. 11, 372-376 (2015)
32. S.K. Jain, R. Sahu, L.A. Walker, B.L. Tekwani, J. Vis. Exp. 70, 4054 (2012)
33. S. Jain, M. Jacob, L. Walker, B. Tekwani, BMC Complement. Altern. Med. 16, 131 (2016)
34. M. Maksimovic, D. Vidic, M. Milos, M.E.S. Olic, S.A. Zic, S. Siljak-Yakovlev, Biochem. Syst. Ecol. 35, 473-478 (2007)
35. M. Abu-Darwish, Z. Abu-Dieyeh, A. Al-Fraihat, S. Al-dalain, F. Afifi, J. Al-Tabbal, Int. J. Agri. Biol. 13, 981-985 (2010)
36. A.C. Figueiredo, J.G. Barroso, L.G. Pedro, J.J.C. Scheffer, Flavour. Fragr. J. 23, 213-226 (2008)
37. J.L.S. Carvalho-Filho, A.F. Blank, P.B. Alves, P.A.D. Ehlert, A.S. Melo, S.C.H. Cavalcanti, M.F. Arrigoni-Blank, R. Silva-Mann, Rev. Bras. Farmacogn. 16, 24-30 (2006)
38. R. Kumar, S. Sharma, V. Pathania, J. Ess. Oil Res. 25, 23-32 (2013)
39. M. Abdallah, R. Abu-Daha, F. Afifi, Jordan. J. Pharm. Sci. 6, 40-47 (2013)
40. H.I.J. Al-Jaber, Essent. Oil Bear. Pl. 18, 718-724 (2015)
41. S.L.D. Silva, P.M. Figueiredo, T. Yano, Acta Amazo. 37, 281-286 (2007)
42. L.C. Chiang, W. Chiang, M.Y. Chang, L.T. Ng, C.C. Lin, Am. J. Chin. Med. 31, 37-46 (2003)
43. R. Ravizza, M.B. Garibold, R. Molteni, E. Monti, Oncol. Rep. 20, 625-630 (2008)
44. J. Alzeer, B.R. Vummidi, R. Arafeh, W. Rimawi, H. Saleem, N.W. Luedtke, J. Med. Plants Res. 8, 408-415 (2014)
45. R. Zamora, Y. Vodovotz, T.R. Billiar, Mol. Med. 6, 347-373 (2000)
46. S.B. Hassan, H. Gali-Muhtasib, H. Göransson, R. Larsson, Anticancer Res. 30, 1911-1919 (2010)
47. G. Suske, Gene 238, 291-300 (1999)
48. A.R. Black, J.D. Black, J. Azizkhan-Clifford, J. Cell Phys. 188, 143-160 (2001)
49. M. Abdelrahim, I. Samudio, R. Smith, R. Burghardt, S. Safe, J. Bio. Chem. 277, 28815-28822 (2002)
50. E. Chiefari, A. Brunetti, F. Arturi, J.-M. Bidart, D. Russo, M. Schlumberger, S. Filetti, BMC Cancer 2(1), 35 (2002)
51. N.Y. Jiang, B.A. Woda, B.F. Banner, G.F. Whalen, K.A. Dresser, D. Lu, Cancer Epid. Prev. Biom. 17, 1648-1652 (2008)
52. H. Durgha, R. Thirugnanasampandan, G. Ramya, M.G. Ramanth, J. King Saud Uni.-Sci. 28, 390-395 (2015)
53. M.S. Abu-Darwish, C. Cabral, I.V. Ferreira, M.J. Gonçalves, C. Cavaleiro, M.T. Cruz, L. Salgueiro, Biomed. Res. Int. 2013, 538940 (2013)
54. R. SilveiraeSá, L.N. Andrade, D.P. Sousa, Molecules 18, 1227-1254 (2013)
55. J. Ma, H. Xu, J. Wu, C. Qu, F. Sun, S. Xu, Int. Immunopharmacol. 29, 708-713 (2015)
56. M. Tosun, S. Ercisli, M. Sengul, H. Ozer, T. Polat, E. Ozturk, Biol Res. 42, 175-181 (2009)
57. B. Nikmehr, H. Ghaznavi, A. Rahbar, S. Sadr, S. Mehrzadi, S. Chin, J. Nat. Med. 12, 423-427 (2014)
58. S. Ślusarczyk, S. Zimmermann, M. Kaiser, A. Matkowski, M. Hamburger, M. Adams, Planta Med. 77, 1594-1596 (2011)
59. S. Hoet, C. Stévigny, M.F. Hérent, J. Quetin-Leclercq, Planta Med. 72, 480 (2006)

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Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities

Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities

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