81
Views
0
CrossRef citations to date
0
Altmetric
Reviews

Semisynthetic Derivatives of Eugenol and their Biological Properties: A Fleeting Look at the Promising Molecules

, , , , , & show all
Pages 379-404 | Received 03 May 2019, Accepted 10 Oct 2020, Published online: 27 Nov 2020

References

  • Rojas, D.F.C., Fernandes desouza, C.R. and Oliveira W.P. (2014). Clove (Syzygium aromati- cum): a precious spice. Asian Pacific Journal of Tropical Biomedicine. 4(2): 90-96.
  • Grayer, R.J., Kite, G.C., Golstone, F.J., Bryan, S.E., Paton, A. and EliPutievsky. (1996). Infraspecific taxonomy and essential oil chemotypes in sweet basil, Ocimum basilicum. Phytochemistry. 43(5): 1033-1039.
  • Nakamura, T.U., Mendonca-Filho, R. R., Morgado-Diaz, J.A., Maza, P.K., Dias Filho, B.P., Garcia Cortez, D.A., SalesAlviano, D. S., Rosa, D.S., Lopes, C.S.H., Sales Alviano, C. and VataruNakamura, C. (2006). Antileishmanial activity of Eugenol-rich essential oil from Ocimum gratissimum. Parasitology International. 55(2): 99-105.
  • Jaganathan, S.K. and Supriyanto, E. (2012). Antiproliferative and molecular mechanism of Eugenol-induced apoptosis in cancer cells. Molecules. 17: 6290-6304.
  • Pramod, K., Ansari, S.H. and Ali, J. (2010). A natural compound with versatile pharmacological actions. Natural Product Communications. 5(12): 1999-2006.
  • Ahmed, M., Amin, S., Islam, M., Takahashi, M., Okuyama, E. and Hossain, C.F. (2000). Analgesic principle from Abutilon indicum. Die Pharmazie. 55(4): 314-316.
  • Desousa, D.P. (2011). Analgesic-like activity of essential oils constituents. Molecules. 16(3): 2233-2252.
  • Nagababu, E., Rifkind, J.M., Boindala, S. and Nakka, L. (2010). Assessment of antioxidant activity of Eugenol In vitro and In vivo. Free Radicals and Antioxidant Protocols. 610: 165-180.
  • Gulcin, I. (2011). Antioxidant activity of Eugenol: AStructure-Activity Relationship Study. Journal of Medicinal Food. 14(9): 975-985.
  • Rubio, L., Motilva, M-J. and Romero, M-P. (2013). Recent advances in biologically active compounds in herbs and spices: A review of the most effective antioxidant and anti-inflammatory active principles. Critical Reviews in Food Science and Nutrition. 53: 943-953.
  • Zhou, L., Zheng, H., Tang, Y., Yu, W. and Gong, Q. (2013). Eugenol inhibits quorum sensing at sub-inhibitory concentrations. Biotechnology Letters. 35(4): 631-637.
  • Chaieb, K., Hajlaui, H., Zmantar, T., Kahla-Nakbi, A.B., Rouabhia, M., Mahdouani, K. and Bakhrouf, A. (2007). The Chemical Composition and Biological Activity of Clove Essential Oil, Eugenia caryophyllata (Syzigiumaromaticum L. Myrtaceae): a Short Review. Phytotherapy Research. 21(6): 501-506.
  • Park, M.J., Gwak, K.S., Yang, K.W.K., Jeung, E.B., Chang, J.W. and Choi, G. (2009). Effect of citral, Eugenol, nerolidol and α-terpineol on the ultrastructural changes of Trichophytonmenta- grophytes. Fitoterapia. 80(5): 290-296.
  • Cheng, S.S., Liu, J.Y., Chang, E.H. and Chang, S-T. (2008). Antifungal activity of cinnamal- dehyde and Eugenol congeners against wood-rot fungi. Bioresource Technology. 99(11): 5145- 5149.
  • Pereira, F.D.O., Mendes, J.M. and Lima, E.D.O. (2013). Investigation on mechanism of anti- gungal activity of Eugenol against Trichophyton rubrum. Medical Mycology. 51(5): 507-513.
  • Walsh, S.E., Maillard, J-Y., Russell, A.D., Catrenich, C.E., Charbonneau, D.L. and Bartolo, R.G. (2003). Activity and mechanism of action of selected biocidal agents on Gram-Positive and negative bacteria. Journal of Applied Micobiology. 94(2): 240-247.
  • Wang, Y-M., Kong, L-C., Liu, J. and Ma, H-X. (2018). Synergistic effect of Eugenol with colistin against clinical isolated Colistin-resistant Escherichia coli strains. Antimicrobial Resistance and Infection Control. 7(17): 2-9.
  • Pathirana, H.N.K.S., Wimalasena, S.H.M.P., DeSilva, B.C.J. and Joon, H.G. (2019). Anti- bacterial activity of clove essential oil and Eugenol against fish pathogenic bacteria isolated from cultured olive flounder. Slovenian Veterinary Research. 56(1): 31-8.
  • Lopes, A.A., Fonseca, F.N., Rocha, T.M., Freitas, L.B., Araujo, E.V.O., Wong, D.V.T., Junior, C.P.L. and Moreira Leal, L.K.A. (2018). Eugenol as a promising molecule for the treatment of dermatitis: Antioxidant and Anti-inflammatory activities and its Nanoformulation. Oxidative Medicine and Cellular Longevity. Article ID 8194849. 1-13.
  • Oztrurk, A. and Ozbek, H. (2005). The anti-inflammatory activity of Eugenia caryophyllata essential oils: an animal model of anti-inflammatory activity. European Journal of General Medicine. 2(4): 159-63.
  • Mak, K-K., Kamal, M.B., Ayuba, S.B., Sakirolla, R., Kang, Y-B., Mohandas, K., Balijipalli, M.K., Ahmad, S.H. and Pichika, M.R. (2019). A comprehensive review on Eugenol’s anti- microbial properties and industry applications: A transformation from ethnomedicine to industry. Pharmacognosy Reviews. 13(25): 1-9.
  • Miyazawa, M. and Hisama, M. (2001). Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/ Psk1002 umu Test. Journal of Agricultural and Food Chemistry. 49(8): 4019-4025.
  • Han, E.H., Hwang, Y.P., Jeong, T.C., Lee, S.S., Shin, J.G. and Jeong, H.G. (2007). Eugenol inhibit 7,12-dimethylbenz[a]anthracene-induced genotoxicity in MCF-7 cells: Bifunctional effects on CYP1 and NAD(P)H: quinone oxidoreductase. FEBS Letters. 581: 749-756.
  • Abraham, S.K. (2001). Anti-genotoxicity of trans-anethole and Eugenol in mice. Food and Chemical Toxicology. 39(5): 493-498.
  • Irie, Y., Itkazu, N., Ajiki, N., Ishige, A., Watanabe, K. and Keung, W.M. (2004). Eugenol exhibits antidepressant like activity in mice and induces expression of metallothionein-III in the hippocampus. Brain Research. 1011(2): 243-246.
  • Sen, P., Maiti, P.C., Puri, S., Ray, A., Audulov, N.A. and Valdman, A.V. (1992). Mechanism of anti-stress activity of Ocimum sanctum Linn, Eugenol and Tinosporamalabarica in experimental animals. Indian Journal of Experimental Biology. 30(7): 592-596.
  • Muller, M., Pape, H.C., Speckmann, E.J. and Gorji, A. (2006). Effects of Eugenol on spreading depression and epileptiform discharges in rat neocortical and hippocampal tissues. Neuro Science. 140(2): 743-751.
  • Bupesh, G., Meenakumari, K., Prabhu, J., Prabhu, K., Kalaiselvi, V.S., Manikandan, E., Krishnarao, M.R. and Sathyarajeswaran, P. (2016). Molecular Properties and Insilico Neuro- protective Activity of Eugenol Against Glutamate Metabotropic Receptors. International Journal of Pharmaceutical Sciences Review and Research. 40(1): 318-323.
  • Irie, Y. (2006). Effects of Eugenol on the Central Nervous System: Its Possible Application to Treatment of Alzheimer’s Disease, Depression, and Parkinson’s Disease. Current Bioactive Compound. 2(1): 57-66.
  • Kasab, R.B. and Bauomy, A.A. (2014). The Neuroprotective efficiency of the aqueous extract of clove (Syzygium aromaticum) in aluminium-induced neurotoxicity. International Journal of Pharmaceutical Sciences. 6(5): 503-508.
  • Das, A., Harshadha, K., DhineshKannan, S.K., Hari Raj, K. and Jayaprakash, B. (2018). Evaluation of therapeutic potential of Eugenol-A natural derivative of Syzygiumaromaticum on cervical cancer. Asian Pacific Journal of Cancer Prevention. 19(7): 1977-1985.
  • Fadilah, F., Andrajati, R. and Arsianti, A. (2017). In-vitro anticancer activity combination of Eugenol and simple aromatic benzoate compounds against human colon HCT-116 cells and WiDr cells. Journal of Pharmaceutical Sciences and Research. 9(5): 637-641.
  • Fadilah, F., Yanuar, A., Arsianti, A. and Andrajaiti, R. (2017). Phenylpropanoids, Eugenol Scaffold, and its derivatives as anticancer. Asian Journal of Pharmaceutical and Clinical Research. 10(3): 41-46.
  • Tursiloadi, S., Artanti, N. and Sulaswatty, A. (2015). Chemical catalytic and biocatalytic process of clove oil derivatives Review. Journal Kimia Terapan Indonesia. 17(1): 69-85.
  • Wenqiang, G., Shufen, L., Ruixiang, Y., Shaokun, T. and Can, Q. (2007). Comparison of essential oils of clove buds extracted with supercritical carbondioxide and other three traditional extraction methods. Food Chemistry. 101(4): 1558-1564.
  • Quan, L., Li, S., Tian, S., Xu, H., Lin, A. and Gu, L. (2004). Determination of Organochlorine Pesticides residue in ginseng root by orthogonal array design soxhlet extraction and gas chromato- graphy. Chromatographia. 59: 89-93.
  • Garkal, D.J., Taralkar, S.V., Kulkarni, P., Jagtap, S. and Nagawade, A. (2012). Kinetic model for extraction of Eugenol from leaves of Ocimum sanctum Linn (Tulsi). International Journal of Pharmaceutical Applications. 3(1): 267-270.
  • Jeyaratnam, N., Nour, A.H., Kanthasamy, R., Nour, A.H., Yuvaraj, A.R. and Akindoyo, O. (2004). Essential oil from Cinnamomum cassia bark through hydrodistillation and advanced microwave assisted hydrodistillation. Industrial Crops and Products. 92: 57-66.
  • Mostafa, K., Yadollah, Y., Fatemeh, S. and Naader, B. (2004). Comparison of essential oil composition of Carum copticum obtained by supercritical carbon dioxide extraction and hydro- distillation methods. Food Chemistry. 86(4): 587-591.
  • Gonzalez-Rivera, J., Duce, C., Falconieri, D., Ferrari, L., Ghezzi, L., Piras, A. and Tine, M.R. (2016). Coaxial microwave assisted hydrodistillation of essential oils from five different herbs (lavender, rosemary, sage, fennal seeds and clove buds): chemical composition and thermal analysis. Innovative Food Science and Emerging Technologies. 33: 308-318.
  • Golmakani, M.T. and Rezaei, K. (2008). Comparison of microwave-assisted hydrodistillation with the traditional hydrodistillation method in the extraction of essential oils from Thymus vulgaris L. Food Chemistry. 109(4): 925-930.
  • Chatterjee, D. and Bhattacharjee, P. (2013). Supercritical carbon dioxide extraction of Eugenol from clove buds. Process optimization and packed bed characterization. Food and Bioprocess Technology. 6: 2587-2599.
  • Gopalkrishnan, N., Shanti, P.P.V. and Narayanan, S. (1990). Composition of clove (Syzygium aromaticum) bud oil extracted using carbon dioxide. Journal of the Science of Food and Agri- culture. 50: 111-117.
  • Alexandru, L., Gravotto, G., Giordana, L., Binello, A. and Chemat, F. (2013). Ultrasound- assisted extraction of clove buds using batch and flow-reactors: a comparative study on a pilot scale. Innovative Food Science and Emerging Technologies. 20: 167-172.
  • Khalil, A.A., Rahman, U., Khan, M.R., Sahar, A., Mehmood, T. and Khan, M. (2017). Essential oil Eugenol: sources, extraction techniques and nutraceutical perspectives. The Royal Society of Chemistry. 7: 32669-32681.
  • Raja, M.R.C., Srinivasan, V., Selvaraj, S. and Mahapatra, S.K. (2015). Versatile and synergistic potential of Eugenol: A review. Pharmaceutica Analytica Acta. 6(5): 1-6.
  • Anuj, G., and Sanjay, S.(2010). Eugenol: A potential phytochemical with multifaceted therapeutic activities. Pharmacology online. 2: 108-120.
  • Baharara, J., Ramezani, T., Mousavi, M. and Kouhestanian, K. (2015). Eugenol suppressed matastasis of breast carcinoma cells and migration by regulation of MMP-9 and Paxilin gene expression. Scholars Journal of Agriculture and Veterinary Sciences. 2(2B): 125-130.
  • Vidhya, N. and Devaraj, N.S. (2011). Induction of apoptosis by eugenol in human breast cancer cells. Indian Journal of Experimental Biology. 49(11): 871-878.
  • Kim, S.S., Oh, O-J., Min, H-Y., Park, E-J., Kim, Y., Park, H.J., Han, Y.N. and Lee, S.K. (2003). Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sciences. 73(3): 337-348.
  • Carrasco, A.H., Espinoza, C.L., Cardile, V., Gallardo, C., Cardona, W., Lombardo, L., Catalan, K.M., Cuellar, M.F. and Russo, A. (2008). Eugenol and its synthetic analogues inhibit cell growth of human cancer cells. Journal of Brazilian Chemical Society. 19(3): 543-48.
  • Nam, H, and Kim, M-M. (2013). Eugenol with antioxidant activity inhibits MMP-9 related to metastasis in human fibrosarcoma cells. Food and Chemical Toxicology. 55: 106-112.
  • Rahman, M.F., Haykal, M.N., Siagian, N.A., Sriepindonnta, P.M. and Tampubolon, N.A. (2018). Synthesis and proapoptotic activity on cervical cancer cell of ester Eugenol 1-(3-methoxy- 4-hydroxy) phenyl-2-propylmethanoate. International Conference on Chemistry and Material science (IC2MS). 299: 1-7.
  • Hidalgo, M.E. and Dela Rosa, C. (2009). Antioxidant capacity of Eugenol derivatives. Quimica Nova. 32(6): 1467-70.
  • Sadeghian, H., Seyedi, S.M., Attaran, N., Jabbari, A. and Jafari, Z. (2011). Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors. Jorural of Enzyme Inhibition and Medicinal Chemistry. 26(2): 238-44.
  • Farias, M.A., Oliveira, P.S., Filipe, S., Dutra, P., Fernandes, T.J., Depereira, C.M.P., De oliveira, S.Q., Stefanello, F.M., Lencina, C.L. and Barschak, A.G. (2013). Eugenol dereivatives as potential antioxidants: is phenolic hydroxyl necessary to obtain an effect. Journal of Pharmacy and Pharmacology. 66: 733-46.
  • Martins, R.M., Farias, M.D.A., Neda, l. F., Pereira, C.M.P.D., Lencina, C. and Lund, R.G. (2016). Antimicrobial and cytotoxic evaluation of Eugenol derivatives. Medicinal Chemistry Research. 25: 2360-2367.
  • Desouza, T.B., Orlandi, M., Coelho, L.F.L., Maloquias, L.C.C., Tranches Dias, A.L., Carvalho, R.R.D., Silva, N.C. and Carvalho, D.T. (2014). Synthesis and invitro evaluation of antifungal and cytotoxic activities of Eugenol glycosides. Medicinal Chemistry Research. 23: 496-502.
  • Vinay, D.V., Jayashekar, P., Padmaja, V., Kurien, J. and William, H. (2014). Synthesis and biological evaluation of 2-allyl-5-hydroxy-4-mehoxy benzaldehyde derivatives for antihyper- lipidemic activity. Journal of Pharmaceutical and Biological Sciences. 2(4): 36-43.
  • Ahmed, A., Younus wani, M., Khan, A., Manzoor, N. and Molepo, J. (2015). Synergistic interactions of Eugenol-tosylate and its congeners with fluconazole against candida albicans. Plos One. 1-7.
  • Abdul rahim, N.H.C., Ansari, A., Ismail, N. and Osman, H. (2017). Synthesis and antibacterial study of Eugenol derivatives. Asian Journal of Chemistry. 29(1): 22-26.
  • Santos de carvalho, L.I., Alvarenga, D.J., Ferreira docarmo, L.C., Gomes de oliveira, L., Silva N.C., Trances dias, A.L., Leomil coelho, L.F., Belarmino desouza, T., Ferreira dias, D. and Carvalho, D.T. (2017). Antifungal activity of new Eugenol-benzoxazole hybrids against Candida spp. Journal of Chemistry. 1-8.
  • Bansode, T.N. (2017). Green synthesis and antimicrobial activity of some Eugenol derivatives. Journal of Chemical and Pharmaceutical Research. 9(4): 145-47.
  • Maida da silva, F.F., Queiroz monte, F.J., Gomes de lemos, T.L., Garcia do nascimento, P.G., Medieros costa, A.K. and Monta de paiva, L.M. (2018). Eugenol derivatives: synthesis, characterization and evaluation of antibacterial and antioxidant activities. Chemistry Central Journal. 12(34): 1-9.
  • Anushree, A.M., Caluvaraju, K.C., Ramachanra setty, S. and Revana siddappa, B.C. (2019). Design, Synthesis, Anti-inflammatory Activity of Eugenol incorporated 1,3,4-oxadiazole derivatives. Journal of Pharmaceutical, Chemical and Biological Sciences. 7(2): 125-37.
  • Olea, A.F., Bravo, A., Martinez, R., Thomas, M., Sedan, C., Espinoza, L., Zambrano, E., Carvajal, D., Silva-moreno, E. and Carrasco, H. (2019). Antifungal activity of Eugenol derivatives against botrytis cinerea. Molecules. 24: 1-4.
  • Awasthi, P.K., Dixit, S.C., Dixit, N. and Sinha, A.K. (2008). Eugenol derivatives as future potential drugs. Journal of Pharmcy Research. 1(2): 215-20.
  • Ngadiwiyana., Ismiyarto., Gunawan., Sarjona, P.R., Prasetya, N.A., Kusworo, T.D. and Susanto, H. (2019). One pot reaction to synthesize allyl etherified Eugenol from clove oil. IOP Conference Series: Materials Science and Engineering. 509: 1-6.
  • Pinto, S.M.L., Rivera, Y., Sandoval, L.V.H., Lizarazo, J.C., Rincon, J. J. and Mendez, Y. V. (2019). Semisynthetic eugenol derivatives as antifungal agents against dermatophytes of the genus Trichophyton. Journal Of Medical Microbiology. 68: 1109-1117.
  • Pinto, S.M.L., Sandoval, L.V.H. and Vargas, L.Y. (2019). In vitro susceptibility of Microsporum spp. and mammalian cells to Eugenia caryophyllus essential oil, eugenol and semisynthetic derivatives. Mycoses. 62: 41-50.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.