Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지
DOI QR코드

DOI QR Code

Essential Oil of Marrubium vulgare: Chemical Composition and Biological Activities. A Review

  • Yabrir, Benalia (Department of Biology, Faculty of Nature and Life Science, Ziane Achour University)
  • Received : 2018.10.09
  • Accepted : 2018.12.09
  • Published : 2019.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Marrubium vulgare, plant species belonging to Marrubium genus, is widespread in the Mediterranean areas, introduced elsewhere and also cultivated in many countries. Its oil is recognized to possess a considerable biological activities with varied chemical composition. This paper aims to overview the chemical composition and biological activities of M. vulgare essential oil's considered as a medicinal plant, widely used in folk medicine overall the world. In essential oils of M. vulgare, germacrene D, ${\beta}$-caryophyllene, ${\beta}$-bisabolene, bicyclogermacrene and carvacrol are generally considered as either mains or minor constituents and each species presents its own composition. Sesquiterpenoids were the dominant fraction while monoterpenoids were present in appreciable or in trace amount. Oxygenated fractions dominated in monoterpenes however, hydrocarbon fraction overpowered in sesquiterpenes. These oils are biologically active, they exhibit an antioxidant and antimicrobial activities and other activities. Due to the variability of composition of essential oil, further studies are necessary, particularly regarding their chemical's which may cause an important change in the biological activities of oils and probably defined different chemotype.

Keywords

References

  1. Harley, R. M.; Atkins, S.; Budantsev, A. L.; Cantino, P. D.; Conn, B. J.; Grayer, R.; Harley, M. M.; de Kok, R.; Krestovskaja, T.; Morales, R.; Paton, A. J.; Ryding O.; Upson, T. In Flowering Plants. Dicotyledons: Lamiales (except Acanthaceae including Avicenniaceae); Kadereit, J. W. Ed.; Springer; Germany, 2004, pp 167-275.
  2. Woodson, R. E. Jr.; Schery, R. W.; Nowicke, J. W.; Epling, C. C. Ann. Mo. Bot. Gard. 1969, 56, 71-111. https://doi.org/10.2307/2395166
  3. Kokkini, S.; Karousou, R.; Hanlidou, E. HERBS 2003, 3082-3090.
  4. Lawrence, B. M. Int. J. Aromather. 2001, 10, 82-98. https://doi.org/10.1016/S0962-4562(01)80002-3
  5. El-Gazzar, A.; Watson, L. New Phytol. 1970, 69, 487-492. https://doi.org/10.1111/j.1469-8137.1970.tb02444.x
  6. Akgul, G.; Ketenoglu, O.; Pinar, N. M.; Kurt, L. Ann. Bot. Fenn. 2008, 45, 1-10. https://doi.org/10.5735/085.045.0101
  7. Lawrence, B. M. Fragrance and flavours; Oxford & IBH Publishing Company Eds, 1989, p 71.
  8. Rodriguez Villanueva, J.; Martin Esteban, J. Phytother. Res. 2016, 30, 1551-1558. https://doi.org/10.1002/ptr.5661
  9. Sabry, R.; Salama, A.; Sharaf-Eldin, M. Arznei Gewurzpfla. 2012, 17, 164-168.
  10. Zawislak, G. Farmacia 2012, 60, 287-292.
  11. Zawislak, G. Acta Agrobot. 2015, 68, 59-62. https://doi.org/10.5586/aa.2015.002
  12. Hmamou, B. D.; Salghi, R.; Zarrouk, A.; Zarrok, H.; Benali, O.; Errami, M.; Hammouti, B. Res. Chem. Intermed. 2013, 39, 3291-3302. https://doi.org/10.1007/s11164-012-0840-2
  13. Nagy, M.; Svajdlenka, E. J. Essent. Oil Res. 1998, 10, 585-587. https://doi.org/10.1080/10412905.1998.9700978
  14. Asadipour, A.; Mehrabani, M.; Nazeri, V.; Tabarraii, M. Ulum-i-Daroei, 2005, 2, 77-82.
  15. Khanavi, M.; Ghasemian, L.; Motlagh, E. H.; Hadjiakhoondi, A.; Shafiee, A. Flavour Fragr. J. 2005, 20, 324-326. https://doi.org/10.1002/ffj.1425
  16. Morteza-Semnani, K.; Saeedi, M.; Babanezhad, E. J. Essent. Oil Res. 2008, 20, 488-490. https://doi.org/10.1080/10412905.2008.9700065
  17. Hamdaoui, B.; Wannes, W. A.; Marrakchi, M.; Ben Brahim, N.; Marzouk, B. J. Essent. Oil Bear. Pl. 2013, 16, 608-612. https://doi.org/10.1080/0972060X.2013.854492
  18. Bayir, B.; Gunduz, H.; Usta, T.; Sahin, E.; Ozdemir, Z.; Kayir, O.; Sen, O.; Aksit, H.; Elmastas, M.; Erenler, R. J. New Res. Sci. 2014, 3, 44-50.
  19. Golparvar, A. R.; Hadipanah, A.; Mehrabi, A. M.; Armin, A. J. Herb. Drugs 2015, 6, 1-5.
  20. Said-Al Ahl, H. A. H.; Gendy, A. S. H.; Mahmoud, A. A.; Mohamed, H. F. Y. Intern. J. Plant Sci. Ecol. 2015, 1, 138-141.
  21. Rezazi, S.; Hanini, S.; Si-Moussa, C.; Abdelmalek, S. J. Agr. Sci. Tech. 2017, 19, 307-322.
  22. Weel, K. G. C.; Venskutonis, P. R.; Pukalskas, A.; Gruzdiene, D.; Linssen, J. P. H. Fett/Lipid, 1999, 10, S395-S400.
  23. Letchamo, W.; Mukhopadhyay, S. J. Hort. Sci. 1997, 72, 741-748. https://doi.org/10.1080/14620316.1997.11515566
  24. Belhattab, R.; Larous, L.; Figueiredo, A. C.; Santos, P. A. G.; Costa, M. M.; Barroso, J. G.; Pedro, L. G. J. Essent. Oil Res. 2006, 18, 369-373. https://doi.org/10.1080/10412905.2006.9699116
  25. Said-Al Ahl, H. A. H.; Sabra, A. S. J. Chem. Pharm. Res. 2016, 8, 863-872.
  26. Kadri, A.; Zarai, Z.; Bekir, A.; Gharsallah, N.; Damak, M.; Gdoura, R. Afr. J. Biotechnol. 2011, 10, 3908-3914.
  27. Abadi, A.; Hassani, A. Int. lett. chem. phys. astron. 2013, 14, 17-24. https://doi.org/10.18052/www.scipress.com/ILCPA.14.17
  28. El-Hawary, S.; EL-Shabrawy, A.; Ezzat, S.; EL-Shibany, F. J. Med. Plants Res. 2013, 7, 1746-1753.
  29. Bokaeian, M.; Saboori, E.; Saeidi, S.; Niazi, A. A.; Amini-Borojeni, N.; Khaje, H.; Bazi, S. Zahedan J. Res. Med. Sci. 2014, 16, 60-64.
  30. Dehbashi, Z.; Mazaheri, M.; Saeedi, S.; Sabbagh, S. K. Adv. Herb. Med. 2016, 2, 9-14.
  31. Zarai, Z.; Kadri, A.; Ben Chobba, I.; Ben Mansour, R.; Bekir, A.; Mejdoub, H.; Gharsallah, N. Lipids Health Dis. 2011, 10, 1-8. https://doi.org/10.1186/1476-511X-10-1
  32. Salama, M. M.; Taher, E. E.; El-Bahy, M. M. Rev. Inst. Med. Trop. Sao Paulo, 2012, 54, 281-286. https://doi.org/10.1590/S0036-46652012000500008
  33. Yabrir, B. Chem. J. Moldova, 2018, 13, 8-23. https://doi.org/10.19261/cjm.2018.506
  34. Ahvazi, M.; Balali, G. R.; Jamzad, Z.; Saeidi, H. J. Med. Plants, 2018, 17, 7-24.
  35. Lodhi, S.; Vadnere, G. P.; Sharma, V. K.; Usman, M. R. J. Intercult. Ethnopharmacol. 2017, 6, 429-452. https://doi.org/10.5455/jice.20170713060840
  36. Smolen, K. Diss. Pharm, 1960, 12, 325-352.
  37. Dmitruk, M.; Haratym, W. Mod. Phytomorphol. 2014, 6, 85.
  38. Ahvazi, M.; Jamzad, Z.; Balali, G. R.; Saeidi, H. Iran. J. Bot. 2016, 22, 39-58.
  39. Lippai, A.; Smith, P. A.; Price, T. V.; Weiss, J.; Lloyd, C. Weed Sci. 1996, 44, 91-99. https://doi.org/10.1017/S0043174500093607
  40. Groenteman, R.; Probst, C.; Bellgard, S.; Prebble, J. Manaaki Whenua; Landcare Research: New Zealand, 2017, p 78.
  41. Benvenuti, S.; Andolfi, L.; Macchia, M. Seed Tech. 2001, 23, 138-144.
  42. Weiss, J.; Ainsworth, N.; Faithfull, I. CRC for Weed Management Systems, University of Adelaide, Australia, 2000, p 6.
  43. Young, J. A.; Evans, R. A. Weed Sci. 1986, 34, 266-270. https://doi.org/10.1017/S0043174500066807
  44. Wiersum, K. F.; Dold, A. P.; Husselman, M.; Cocks, M. Frontis: Medicinal and aromatic plants; Bogers, R. J.; Craker, L. E.; Lange, D.; Springer; Netherlands, 2006, pp 43-57.
  45. Garjani, A.; Tila, D.; Hamedeyazdan, S.; Vaez, H.; Rameshrad, M.; Pashaii, M.; Fathiazad, F. Folia Morphol. 2017, 76, 361-371. https://doi.org/10.5603/FM.a2017.0011
  46. Tahri, N.; El Basti, A.; Zidane, L.; Rochdi, A.; Douira, A. Kastamonu Univ., J. Fores. Fac. 2012, 12, 192-208.
  47. Masoodi, M. H.; Ahmad, B. J. Pharm. Res. 2012, 5, 2668-2671.
  48. Oran, S. A.; Al-Eisawi, D. M. Dirasat 1998, 25, 84-112.
  49. VanderJagt, T. J.; Ghattas, R.; VanderJagt, D. J.; Crossey, M.; Glew, R. H. Life Sci. 2002, 70, 1035-1040. https://doi.org/10.1016/S0024-3205(01)01481-3
  50. Herrera-Arellano, A.; Aguilar-Santamaria, L.; Garcia-Hernandez, B.; Nicasio-Torres, P.; Tortoriello, J. Phytomed. 2004, 11, 561-566. https://doi.org/10.1016/j.phymed.2004.01.006
  51. Knoss, W. Biotechnol. Agric. For. 1999, 43, 274-289.
  52. de Souza, M. M.; de Jesus, R. A.; Cechinel-Filho, V. ; Schlemper, V. Phytomedicine 1998, 5, 103-107. https://doi.org/10.1016/S0944-7113(98)80005-6
  53. Ibrahim, F. M.; Ibrahim, A. Y.; Omer, E. A. World J. Pharm. Sci. 2014, 2, 1664-1670.
  54. Haq, F.; Ahmad, H.; Alam, M. J. Med. Plant. Res. 2011, 5, 39-48.
  55. Lawrence, B. M. In Manual on the essential oil industry: The Isolation of Aromatic Materials from Natural Natural Plant Products; De Silva, K.T. Ed; United Nations Industrial Development Organization; Austria, 1996, pp 57-154.
  56. Rassem, H. H. A.; Nour, A. H.; Yunus, R. M. Aust. J. Basic Appl. Sci. 2016, 10, 117-127.
  57. Scheffer, J. J. C. Phytother. Res. 1996, 10, s6-s7.
  58. Craveiro, A. A.; Matos, F. J. A.; Alencar, J. W.; Plumel, M. M. Flavour Frag. J. 1989, 4, 43-44. https://doi.org/10.1002/ffj.2730040110
  59. Kumar, S. Analytical technique for natural product research, CABI; Boston, USA, 2015, p 204.
  60. Stashenko, E. E.; Jaramillo, B. E.; Martinez, J. R. J. Chromatogr. A. 2004, 1025, 105-113. https://doi.org/10.1016/j.chroma.2003.10.059
  61. Chemat, F.; Lucchesie, M. E. J. Soc. Ouest-Afr. Chim. 2005, 020, 77-99.
  62. Chemat, F.; Abert-Vian, M.; Fernandez, X. In Microwave-assisted Extraction for Bioactive Compounds Theory and Practice: Microwave-Assisted Extraction of Essential Oils and Aromas; Chemat, F.; Cravotto, G. Ed; Food Engineering Series; USA, 2013, pp 53-68.
  63. Pallado, P.; Tassinato, G.; D'Alpaos, M.; Traldi, P. Rapid Commun. Mass Spectrom. 1997, 11, 1335-1341. https://doi.org/10.1002/(SICI)1097-0231(199708)11:12<1335::AID-RCM970>3.0.CO;2-R
  64. Miloudi, K.; Hamimed, A.; Benmimoun, Y.; Bellebna, Y.; Taibi, A.; Tilmatine, A. Carpath. J. Food Sci. Technol. 2018, 10, 104-110.
  65. Zellner, Bd'. A.; Dugo, P.; Dugo, G.; Mondello, L. Analysis of Essential Oils; CRC Press Taylor & Francis Group; Florida, 2010, pp 151-183.
  66. Pengelly, A. The constituents of medicinal plants: An introduction to the chemistry and therapeutics of herbal medicines; A&U Academic; Australia, 1999, p 172.
  67. Bruneton, J. Pharmacognosie, Phytochimie, Plantes medicinales; Lavoisier Tec et Doc Ed; France, 1999, p 1504.
  68. Baudoux, D. Aroma News 1997, 9/97, 1-6.
  69. Laouer, H.; Yabrir, B.; Djeridane, A.; Yousfi, M.; Beldovini, N.; Lamamra, M. Nat. Prod. Commun. 2009, 4, 1133-1138.
  70. Lincoln, D. E.; Langeheim, J. H. Biochem. Syst. Ecol. 1981, 9, 153-160. https://doi.org/10.1016/0305-1978(81)90033-8
  71. Gotsiou, P.; Naxakis, G.; Skoula, M. Biochem. Syst. Ecol. 2002, 30, 865-879. https://doi.org/10.1016/S0305-1978(02)00025-X
  72. Franz, C.; Novak, J. Sources of essential oils; CRC Press Taylor & Francis Group; Florida, 2010, pp 39-81.
  73. Mohammadhosseini, M. J. Med. Plants By-prod. 2016, 5, 169-180.
  74. Adorjan, B.; Buchbauer, G. Flavour Fragr. J. 2010, 25, 407-426. https://doi.org/10.1002/ffj.2024
  75. Nakatsu, T.; Lupo Jr, A. T.; Chinn Jr, J. W.; Kang, R. L. Studies Nat. Prod. Chem. 2000, 21B, 571-631. https://doi.org/10.1016/S1572-5995(00)80014-9
  76. Lahlou, M. Phytother. Res. 2004, 18, 435-448. https://doi.org/10.1002/ptr.1465

Cited by

  1. Marrubium vulgare L.: A Phytochemical and Pharmacological Overview vol.25, pp.12, 2019, https://doi.org/10.3390/molecules25122898
  2. Chemical Characterization of Marrubium vulgare Volatiles from Serbia vol.10, pp.3, 2019, https://doi.org/10.3390/plants10030600
  3. The Botanical, Chemical and Ethnobotanical Diversity of Southern African Lamiaceae vol.26, pp.12, 2021, https://doi.org/10.3390/molecules26123712