Antioxidant Activity and Phenolic Compounds of Lawson Molecule Extracted from Lawsonia inermis (Henna)

Year 2021, , 1 - 16, 01.04.2021

Enayatullah Rahmani , Avni Çakıcı , Elif Çakır

https://doi.org/10.17932/IAU.IJFER.2015.003/ijfer_v07i1001

Abstract

The henna plant (Lawsonia inermis) which is known and used as a dye plant from past to present, plays a role in our lives with its cultural effects. Besides being a cosmetic agent, it has pharmacological properties. Studies have identified about 70 phenolic compounds that it contains such as flavonoids, naphthoquinones, quinoids, naphthalene derivatives, triterpenoids, organic acids, tannins, phenolic and phenolic glycosides. Thanks to these bioactive compounds, it has been determined that it is a medicinal plant with positive impacts on health with its anticarcinogenic, antimicrobial, anti-inflammatory, analgesic and antipyretic properties. The main coloring agent found in its leaves is the lawsone molecule, a red-orange pigment and it is a subgroup of naphthoquinones. Although there are many pharmacological research findings, studies on antioxidant and antimicrobial activities draw more attention. More researches and more in vivo and in vitro studies are needed for pharmacological activities and specific compounds.

Keywords

Henna, Lawson molecule, phenolic compounds, antioxidant activity

References

• 1. Chaudhary, G., S. Goyal, and P. Poonia, Lawsonia inermis Linnaeus: a phytopharmacological review. Int J Pharm Sci Drug Res, 2010. 2(2): p. 91-8.
• 2. Basipogu, B. and N. Syed, Gastro protective activity of Lawsonia inermis (henna), a well-known medicinal plant. International Journal of Applied Research, 2015. 1: p. 833-837.
• 3. Sherrow, V., Encyclopedia of hair: a cultural history. 2006: Greenwood Publishing Group.
• 4. Agarwal, P., S. Alok, and A. Verma, An update on ayurvedic herb henna (Lawsonia inermis L.): A review. International Journal of Pharmaceutical Sciences and Research, 2014. 5(2): p. 330.
• 5. Brahmeshwari, G., M. Surekha, and K. Saini, Antifungal activity of naphthothiazoles derived from Lawsone (Lawsonia inermis). African Journal of Biotechnology, 2012. 11(78): p. 14405-14409.
• 6. Ogunbinu, A.O., et al., Study on the essential oil of Lawsonia inermis (L) Lythraceae. Journal of Essential Oil Bearing Plants, 2007. 10(3): p. 184-188.
• 7. Tadesse, M. and B. Mesfin, A review of selected plants used in the maintenance of health and wellness in Ethiopia. Ethiopian e-Journal for Research and Innovation Foresight, 2010. 2(1): p. 85-102.
• 8. Wright, C. and G.V. Ullas, An improved synthesis of [phenyl‐14C (U)] Lawsone. Journal of Labelled Compounds and Radiopharmaceuticals: The Official Journal of the International Isotope Society, 2002. 45(14): p. 1265-1268.
• 9. Singh, Y., S. Kumar, and M. Singh, Agro History, Uses, Ecology. And Distribution of Henna (Lawsonia Inermis) Henna Cultivation, Improvement and trade Central and Arid zone Jodpur, India, 2005: p. 11-12.
• 10. Rahiman, F.A., et al., Antimicrobial properties of Lawsonia inermis syn. Lawsonia alba in vivo and in vitro. J Food Agric Environ, 2013. 11: p. 502-504.
• 11. Raja, W., M. Ovais, and A. Dubey, Phytochemical screening and antibacterial activity of Lawsonia inermis leaf extract. medicine, 2013. 6(8).
• 12. Siddiqui, B.S., et al., Two new and a known compound from Lawsonia inermis. Helvetica Chimica Acta, 2003. 86(6): p. 2164-2169.
• 13. Siddiqui, B.S., M.N. Kardar, and S. Khan, Two new triterpenoids from Lawsonia alba. Zeitschrift für Naturforschung B, 2005. 60(1): p. 37-40.
• 14. Semwal, R.B., et al., Lawsonia inermis L.(henna): Ethnobotanical, phytochemical and pharmacological aspects. Journal of Ethnopharmacology, 2014. 155(1): p. 80-103.
• 15. Beemelmanns, C., et al., Natural products from microbes associated with insects. Beilstein journal of organic chemistry, 2016. 12(1): p. 314-327.
• 16. Cahyana, A., A. Mafazi, and A. Liandi. Synthesis of antioxidant agents based on improvement of hydroxyl groups prepared from lawsone compounds. in AIP Conference Proceedings. 2020. AIP Publishing LLC.
• 17. Cipriani, F.A., et al., Implicações químicas na sistemática e filogenia de Bignoniaceae. Química Nova, 2012. 35(11): p. 2125-2131.
• 18. Futuro, D.O., et al., The antifungal activity of naphthoquinones: An integrative review. Anais da Academia Brasileira de Ciências, 2018. 90: p. 1187-1214.
• 19. Khalaphallah, R. and W.S. Soliman, Effect of henna and roselle extracts on pathogenic bacteria. Asian Pacific Journal of Tropical Disease, 2014. 4(4): p. 292-296.
• 20. Ganesan, A., The impact of natural products upon modern drug discovery. Current opinion in chemical biology, 2008. 12(3): p. 306-317. 21. Hirakawa, K., et al., Naphthoquinones from juglandaceae. Phytochemistry, 1986. 25(6): p. 1494-1495.
• 22. Jentzsch, J., et al., New Antiparasitic Bis‐Naphthoquinone Derivatives. Chemistry & biodiversity, 2020. 17(2): p. e1900597.
• 23. Mehendale, A.R. and R.H. Thomson, Binaphthoquinones in lomatia ferruginea. Phytochemistry, 1975. 14(3): p. 801-802.
• 24. Pardhasaradhi, M. and M. HariBabu, A new bisjuglone from Juglans regia root bark. 1978.
• 25. Riaz, M.T., et al., Synthesis, biological activity and docking calculations of bis-naphthoquinone derivatives from lawsone. Bioorganic Chemistry, 2021. 114: p. 105069.
• 26. Banerjee, A. and A. Mukherjee, Chemical aspects of santalin as a histological stain. Stain Technology, 1981. 56(2): p. 83-85.
• 27. Diderot, N.T., N. Silvere, and T. Etienne, Xanthones as therapeutic agents: chemistry and pharmacology. Advances in Phytomedicine, 2006. 2: p. 273-298.
• 28. Knight, C.G. and T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles. Biochemical Journal, 1989. 258(3): p. 683-687.
• 29. Lambert, R., et al. PCT Int. Appl. WO 9706178, 1997. in Chem. Abstr. 1997.
• 30. Loh, W.-S., et al., 4a-Hydroxy-9-(2-methoxyphenyl)-4, 4a, 5, 6, 7, 8, 9, 9a-octahydro-3H-xanthene-1, 8 (2H)-dione. Acta Crystallographica Section E: Structure Reports Online, 2011. 67(1): p. o35-o36.
• 31. Yadav, S., B. Nand, and J.M. Khurana, An efficient synthesis of novel 3-hydroxy-12-arylbenzo [a] xanthen-11-ones and 5, 12-diarylxantheno [2, 1-a] xanthene-4, 12-diones using p TSA in [bmim] BF4. Canadian Journal of Chemistry, 2013. 91(8): p. 698-703.
• 32. Kirkland, D., et al., Testing strategies in mutagenicity and genetic toxicology: an appraisal of the guidelines of the European Scientific Committee for Cosmetics and Non-Food Products for the evaluation of hair dyes. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2005. 588(2): p. 88-105.
• 33. Kirkland, D. and D. Marzin, An assessment of the genotoxicity of 2-hydroxy-1, 4-naphthoquinone, the natural dye ingredient of Henna. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2003. 537(2): p. 183-199.
• 34. Marzin, D. and D. Kirkland, 2-Hydroxy-1, 4-naphthoquinone, the natural dye of Henna, is non-genotoxic in the mouse bone marrow micronucleus test and does not produce oxidative DNA damage in Chinese hamster ovary cells. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 2004. 560(1): p. 41-47.
• 35. Al-Rubiay, K.K., et al., Antimicrobial efficacy of henna extracts. Oman medical journal, 2008. 23(4): p. 253.
• 36. Bairagi, G., A. Kabra, and R. Mandade, Anthelmintic activity of Lawsonia inermis L. leaves in Indian adult earthworm. International Journal of Research in Pharmaceutical and Biomedical Sciences, 2011. 2(1): p. 237-240.
• 37. Ozaslan, M., et al., Antitumoral effect of L. inermis in mice with EAC. IJP-International Journal of Pharmacology, 2009. 5(4): p. 263-267.
• 38. Saadabi, M.A., Evaluation of Lawsonia inermis Linn.(Sudanese henna) leaf extracts as an antimicrobial agent. Research Journal of Biological Sciences, 2007. 2(4): p. 419-423.
• 39. Abadehie, F.S., et al., Lawsone-encapsulated chitosan/polyethylene oxide nanofibrous mat as a potential antibacterial biobased wound dressing. Engineered Regeneration, 2022.
• 40. Uddin, N., et al., Bioactive flavonoids from the leaves of Lawsonia alba (Henna). Phytochemistry Letters, 2011. 4(4): p. 454-458.
• 41. Ahmad, I. and A.Z. Beg, Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multi-drug resistant human pathogens. Journal of ethnopharmacology, 2001. 74(2): p. 113-123.
• 42. Pasandi Pour, A. and H. Farahbakhsh, Lawsonia inermis L. leaves aqueous extract as a natural antioxidant and antibacterial product. Natural product research, 2020. 34(23): p. 3399-3403.
• 43. Uma, D., C. Ho, and W. Wan Aida, Optimization of extraction parameters of total phenolic compounds from henna (Lawsonia inermis) leaves. Sains Malaysiana, 2010. 39(1): p. 119-128.
• 44. Zohourian, T.H., et al., Polyphenolic contents and antioxidant activities of Lawsonia inermis leaf extracts obtained by microwave-assisted hydrothermal method. Journal of Microwave Power and Electromagnetic Energy, 2011. 45(4): p. 193-204.
• 45. Tekin V., B.M.F.Z., Kilçar A. Y. , Ünak P., Kına Yapragından Ekstrakte Edilen Lawsone Bilesiginin Radyo isaretlenmesi ve Biyodağılımının Ilaç Kimyasi, Üretimi, Teknolojisi, Standardizasyonu Kongresi. 2013, Kimyagerler Dernegi: Antalya.
• 46. Hosein, H.K.M. and D. Zinab, Phenolic compounds and antioxidant activity of henna leaves extracts (Lawsonia inermis). World Journal of Dairy & Food Sciences, 2007. 2(1): p. 38-41.