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Plant Profiler

Clove (Syzygium aromaticum)


Clove (Syzygium aromaticum) Image

Synonyms / Common Names / Related Terms
2-methoxy-4-(2-propenyl)-phenol, Caryophylli atheroleum, Caryophylli Flos, caryophyllum, caryophyllus, Caryophyllus aromaticus, cengke, cengkeh, chiodo di garofano (Italian), choji, chor boghbojh, chor poghpch, cinnamon nails, clau, clavos, clou de girofle, Clous de Girolfe (French), clovas de comer, clove bud, clove bud oil, clove cigarettes, clove essential oil, clove leaf, craveiro da india, cravinho, cravo, cravo de olor, cuisoare, ding heung, ding xiang, dinh huong, dok chan, dried clove, Eugenia aromatica, Eugenia bud, Eugenia caryophyllata, Eugenia caryophyllus, faranfil, Flores Caryophylli, gahn plu, garifalo, garifallo, garifano, garn ploo, Gewurznelken Nagelein (German), gozdzik, gozdzikow korzenny, graambu, ground clove, gvazdikelia, gvozdika, harilik nelgipuu, hrebicek, iltze kanela, jeonghyang, jeonghyong namu, jonghyang, kabsh qarunfil, kala, kalmpir, kan phou, kan phu, karafuu, karamfil, kariofilla, kariofilo, khan pluu, khlam puu, klabong pako, klincic, klinceky, klincki, krambu, kreteks, krinfud, kruidnagel, krustnaglinas, kryddnejlikor, kryddernellike, kullobu, kurobu, kvapnusis gvazdikmedis, labanga, labango, laung, lavang, lavanga, lavangalu, lavnagamu, lay hnyin, leoung, ley nyim bwint, mikhak, mikhaki, mixaki, moschokarfi, Myrtaceae (family), nageljnove zbice, nagri, negull, neilikka, nejlikor, nelk, nelke, nellik, nellike, oil of clove, oleum caryophylli, pentogen (clove oil), qalampir, shriisanjnan, Syzigium aromaricum (L) Merr. and Perry., szegfu, szegfuszeg, tropical myrtle, tsiporen.

Note: Do not confuse clove with baguacu, black plum, Eugenia cumini, Eugenia edulis, Eugenia jambolana, Eugenia umbelliflora, Jamun, java apple, java plum, SCE, Syzigium cordatum, Syzygium cumini, Syzygium samarangense, water apple, or wax apple.

 

Mechanism of Action

Pharmacology:

  • Constituents: Alpha-humulene13, benzoates25, eugenol (4-alil-2-metoxiphenol), eugenol acetate5,14,10,13, ethyl acetate8, beta caryophyllene13, isoeugenol13, phenylpropanoids8, dehydrodieugenol8, methyleugenol13, methyl salicylate13, trans-coniferyl aldehyde8, and triterpenes (oleanolic acid)9 are constituents of clove. Eugenol, a volatile oil extracted from clove, is believed to be responsible for many of the therapeutic and toxic actions of clove.
  • Analgesic / anesthetic effects: One randomized trial found that a homemade clove gel is as effective as an oral anesthetic benzocaine 20% gel15. However, the clove component eugenol may inhibit prostaglandin biosynthesis and thereby depress pain sensory receptors16. It is unclear whether clove displays an anesthetic or analgesic mechanism of action or both. Additional study is needed to clarify these findings.
  • Antibacterial effects: Flower extract of clove and ethanol extract were shown to inhibit the growth of Helicobacter pylori26,3. Oil of clove showed a germicidal effect against Klebsiella pneumoniae, Pseudomonas aerugenosa, Clostridium perfringes, Escherichia coli, Proteus vulgaris, Mycobacterium smegmatis, Bacillus subtilis, Salmonella enterica, Listeria monocytogenes, Candida albicans, and five strains of Staphylococcus aureus27,28,29,7. Hemolysis due to alpha-toxin produced by Staphylococcus aureus was significantly reduced after a culture with clove oil4. The oil also significantly decreased the production of enterotoxin A and enterotoxin B, also produced by S. aureus. Schapoval et al., however, found no anti-microbial properties when they used extracts of dried and fresh leaves of clove30.
  • Anticancer effects: Eugenol-treated HL-60 cells displayed features of apoptosis including DNA fragmentation and formation of DNA ladders in agarose gel electrophoresis. Eugenol transduced the apoptotic signal via ROS generation, thereby inducing mitochondrial permeability transition (MPT), reducing anti-apoptotic protein bcl-2 levels, inducing cytochrome c release to the cytosol, and subsequent apoptotic cell death2.
  • Antifungal effects: Hasan et al. found that clove oil may prevent mycotoxin production by Aspergillus species18. Similarly, another study has found that clove had a high inhibitory effect on dermatophytic fungi19. Antifungal activity of eugenol involved alteration of both membrane and cell wall of the yeast5. A similar in vitro study indicated that eugenol exerted an anticandidal effect by a mechanism implicating an important envelope damage6. The fungicidal activity was similar with nystatin used as a reference treatment. Essential oils were tested for activity against common fungi causing spoilage of bakery products, Eurotium amstelodami, E. herbariorum, E. repens, E. rubrum, Aspergillus flavus, A. niger, and Penicillium corylophilum11. Clove essential oil was found to totally inhibit the microorganisms tested. Saccharomyces cerevisiae cell lysis was shown by the release of substances absorbing at 260nm20. In addition, scanning electron microscopy analyses revealed that the surface of treated cells by clove oil was significantly damaged.
  • Antihistamine properties: In a rat study, clove, specifically the eugenol in clove, showed antihistamine and antianaphylactic activity21.
  • Anti-inflammatory effects: Substrate dependent enzyme kinetics showed that the inhibitory effect of eugenol on 5-LO is of a non-competitive nature. Eugenol significantly inhibited the formation of LTC(4) in calcium ionophore A23187 and arachidonic acid (AA) stimulated polymorphonuclear leukocytes PMNL cells. These data suggest that eugenol inhibits 5-lipoxygenase (5-LO) by non-competitive mechanism and also inhibits formation of leukotriene C(4)(LTC(4)) in human PMNL cells and thus may have beneficial role in modulating 5-LO pathway in human PMNL cells17. Eugenol also suppressed cyclooxygenase-2 expression in lipoplysaccharide stimulated mouse macrophage RAW264.7 cells31. Theoretically, clove may inhibit cyclooxygenase and lipoxygenase metabolic pathways, thereby inhibiting prostaglandin and leukotriene biosynthesis.
  • Antimutagenic effects: Three studies examined the mutagenicity of various herbs and concluded that clove may possess anti-mutagenic properties32,33,34,8.
  • Antipyretic effects: A study found that eugenol possesses greater antipyretic properties than acetaminophen when given intravenously in small doses to rabbits22. When clove water extract is applied to rat enterocytes, it can permeate the membrane and inhibit N(+)/K(+) ATPase35.
  • Chemoprotective effects: Clove may have chemoprotective properties against liver and bone marrow toxicity (anecdotal).
  • Hepatic properties: In a rat study, clove reduced levels of cytochrome P450 enyzmes24.
  • Insecticidal effects: Significant correlations among adulticidal, nymphicidal, and ovicidal activities against Trialeurodes vaporariorum (greenhouse whitefly) were observed with clove leaf oil12.
  • Mitochondrial effects: ATPases Na+/K+ ATPase, Cu2+-ATPase, and F0F1ATPase are possible intracellular targets for the action of clove spice's components that result in: a decrease in ATP level, defects in proton and ion transports leading to electrolyte imbalance and derangements in mitochondrial function36.
  • Renal effects: Based on a case report, ingested clove oil may be nephrotoxic1.
  • Vasorelaxant effects: In a rat study, eugenol from clove showed vasorelaxant properties23.

 

Pharmacodynamics/Kinetics:

  • Rat hepatocytes actively metabolize the clove component eugenol, suggesting liver metabolism of the agent37.
  • Volunteers were given 12 gingersnaps, which were high in methyleugenol, (a constituent of clove), for breakfast38. Blood was drawn immediately before the mean and at 15, 30, 60, and 120 minutes afterward. The mean ± standard deviation fasting level of methyleugenol in serum was 16.2 ± 4.0pg/g wet weight. Peak blood levels were found at 15 minutes (mean ± SD, 53.9 ± 7.3pg/g wet weight), followed by a rapid decline; the half-life of elimination was about 90 minutes.

 

References

  1. Lane, B. W., Ellenhorn, M. J., Hulbert, T. V., and McCarron, M. Clove oil ingestion in an infant. Hum Exp Toxicol 1991;10(4):291-294. 1679654
  2. Yoo, C. B., Han, K. T., Cho, K. S., Ha, J., Park, H. J., Nam, J. H., Kil, U. H., and Lee, K. T. Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett 7-8-2005;225(1):41-52. 15922856
  3. Li, Y., Xu, C., Zhang, Q., Liu, J. Y., and Tan, R. X. In vitro anti-Helicobacter pylori action of 30 Chinese herbal medicines used to treat ulcer diseases. J Ethnopharmacol 4-26-2005;98(3):329-333. 15814268
  4. Smith-Palmer, A., Stewart, J., and Fyfe, L. Influence of subinhibitory concentrations of plant essential oils on the production of enterotoxins A and B and alpha-toxin by Staphylococcus aureus. J Med Microbiol 2004;53(Pt 10):1023-1027. 15358826
  5. Bennis, S., Chami, F., Chami, N., Bouchikhi, T., and Remmal, A. Surface alteration of Saccharomyces cerevisiae induced by thymol and eugenol. Lett Appl Microbiol 2004;38(6):454-458. 15130138
  6. Chami, N., Bennis, S., Chami, F., Aboussekhra, A., and Remmal, A. Study of anticandidal activity of carvacrol and eugenol in vitro and in vivo. Oral Microbiol Immunol 2005;20(2):106-111. 15720571
  7. Leuschner, R. G. and Ielsch, V. Antimicrobial effects of garlic, clove and red hot chilli on Listeria monocytogenes in broth model systems and soft cheese. Int J Food Sci Nutr 2003;54(2):127-133. 12701369
  8. Miyazawa, M. and Hisama, M. Antimutagenic activity of phenylpropanoids from clove (Syzygium aromaticum). J Agric Food Chem 10-22-2003;51(22):6413-6422. 14558756
  9. Somova, L. O., Nadar, A., Rammanan, P., and Shode, F. O. Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. Phytomedicine 2003;10(2-3):115-121. 12725563
  10. Dip, E. C., Pereira, N. A., and Fernandes, P. D. Ability of eugenol to reduce tongue edema induced by Dieffenbachia picta Schott in mice. Toxicon 2004;43(6):729-735. 15109894
  11. Guynot, M. E., Ramos, A. J., Seto, L., Purroy, P., Sanchis, V., and Marin, S. Antifungal activity of volatile compounds generated by essential oils against fungi commonly causing deterioration of bakery products. J Appl Microbiol 2003;94(5):893-899. 12694455
  12. Choi, W. I., Lee, E. H., Choi, B. R., Park, H. M., and Ahn, Y. J. Toxicity of plant essential oils to Trialeurodes vaporariorum (Homoptera: Aleyrodidae). J Econ Entomol 2003;96(5):1479-1484. 14650521
  13. Yang, Y. C., Lee, S. H., Lee, W. J., Choi, D. H., and Ahn, Y. J. Ovicidal and adulticidal effects of Eugenia caryophyllata bud and leaf oil compounds on Pediculus capitis. J Agric Food Chem 8-13-2003;51(17):4884-4888. 12903940
  14. Chami, F., Chami, N., Bennis, S., Trouillas, J., and Remmal, A. Evaluation of carvacrol and eugenol as prophylaxis and treatment of vaginal candidiasis in an immunosuppressed rat model. J Antimicrob Chemother 2004;54(5):909-914. 15456732
  15. Alqareer, A., Alyahya, A., and Andersson, L. The effect of clove and benzocaine versus placebo as topical anesthetics. J Dent 2006;34(10):747-750. 16530911
  16. Pongprayoon, U., Baeckstrom, P., Jacobsson, U., Lindstrom, M., and Bohlin, L. Compounds inhibiting prostaglandin synthesis isolated from Ipomoea pes-caprae. Planta Med 1991;57(6):515-518. 1818340
  17. Raghavenra, H., Diwakr, B. T., Lokesh, B. R., and Naidu, K. A. Eugenol--the active principle from cloves inhibits 5-lipoxygenase activity and leukotriene-C4 in human PMNL cells. Prostaglandins Leukot Essent Fatty Acids 2006;74(1):23-27. 16216483
  18. Hasan, H. A. and Issa, A. A. Influences of chemical fertilizers (in vitro) on aflatoxin and citrinin synthesis by two strains of aspergilli. Folia Microbiol (Praha) 1993;38(6):456-458. 8150393
  19. el Naghy, M. A., Maghazy, S. N., Fadl-Allah, E. M., and el Gendy, Z. K. Fungistatic action of natural oils and fatty acids on dermatophytic and saprophytic fungi. Zentralbl Mikrobiol 1992;147(3-4):214-220. 1609554
  20. Chami, F., Chami, N., Bennis, S., Bouchikhi, T., and Remmal, A. Oregano and clove essential oils induce surface alteration of Saccharomyces cerevisiae. Phytother Res 2005;19(5):405-408. 16106385
  21. Kim, H. M., Lee, E. H., Kim, C. Y., Chung, J. G., Kim, S. H., Lim, J. P., and Shin, T. Y. Antianaphylactic properties of eugenol. Pharmacol Res 1997;36(6):475-480. 9508673
  22. Feng, J. and Lipton, J. M. Eugenol: antipyretic activity in rabbits. Neuropharmacology 1987;26(12):1775-1778. 3501843
  23. Damiani, C. E., Rossoni, L. V., and Vassallo, D. V. Vasorelaxant effects of eugenol on rat thoracic aorta. Vascul Pharmacol 2003;40(1):59-66. 12646411
  24. Kumari, M. V. Modulatory influences of clove (Caryophyllus aromaticus, L) on hepatic detoxification systems and bone marrow genotoxicity in male Swiss albino mice. Cancer Lett 1991;60(1):67-73. 1913628
  25. Yasuda, M., Sonda, T., Hiraoka, T., Horita, A., and Tabata, M. Effects of the molecular properties of mixed solvents on the elution of alkyl benzoates in RPLC. Anal Sci 2003;19(12):1637-1641. 14696928
  26. Bae, E. A., Han, M. J., Kim, N. J., and Kim, D. H. Anti-Helicobacter pylori activity of herbal medicines. Biol Pharm Bull 1998;21(9):990-992. 9781854
  27. Briozzo, J., Nunez, L., Chirife, J., Herszage, L., and D'Aquino, M. Antimicrobial activity of clove oil dispersed in a concentrated sugar solution. J Appl Bacteriol 1989;66(1):69-75. 2542213
  28. Martinez Nadal NG and Montalvo AE. Antimicrobial properties of bay and other phenolic essential oils. Cosmet Perfum 1973;88(10):37-38.
  29. Friedman, M., Henika, P. R., Levin, C. E., and Mandrell, R. E. Antibacterial activities of plant essential oils and their components against Escherichia coli O157:H7 and Salmonella enterica in apple juice. J Agric Food Chem. 9-22-2004;52(19):6042-6048. 15366861
  30. Schapoval, E. E., Silveira, S. M., Miranda, M. L., Alice, C. B., and Henriques, A. T. Evaluation of some pharmacological activities of Eugenia uniflora L. J Ethnopharmacol 1994;44(3):137-142. 7898120
  31. Kim, S. S., Oh, O. J., Min, H. Y., Park, E. J., Kim, Y., Park, H. J., Nam, Han Y., and Lee, S. K. Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci 6-6-2003;73(3):337-348. 12757841
  32. Soudamini, K. K., Unnikrishnan, M. C., Sukumaran, K., and Kuttan, R. Mutagenicity and anti-mutagenicity of selected spices. Indian J Physiol Pharmacol 1995;39(4):347-353. 8582746
  33. Zheng, G. Q., Kenney, P. M., and Lam, L. K. Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents. J Nat Prod 1992;55(7):999-1003. 1402962
  34. Abraham, S. K. and Kesavan, P. C. Evaluation of possible mutagenicity of the condiment clove when administered alone or in combination with caffeine in Drosophila melanogaster. Indian J Exp Biol 1978;16(4):518-519. 98437
  35. Kreydiyyeh, S. I., Usta, J., and Copti, R. Effect of cinnamon, clove and some of their constituents on the Na(+)- K(+)-ATPase activity and alanine absorption in the rat jejunum. Food Chem Toxicol 2000;38(9):755-762. 10930696
  36. Usta, J., Kreydiyyeh, S., Barnabe, P., Bou-Moughlabay, Y., and Nakkash-Chmaisse, H. Comparative study on the effect of cinnamon and clove extracts and their main components on different types of ATPases. Hum Exp Toxicol 2003;22(7):355-362. 12929725
  37. Thompson, D. C., Constantin-Teodosiu, D., and Moldeus, P. Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem Biol Interact 1991;77(2):137-147. 1991333
  38. Schecter, A., Lucier, G. W., Cunningham, M. L., Abdo, K. M., Blumenthal, G., Silver, A. G., Melnick, R., Portier, C., Barr, D. B., Barr, J. R., Stanfill, S. B., Patterson, D. G., Jr., Needham, L. L., Stopford, W., Masten, S., Mignogna, J., and Tung, K. C. Human consumption of methyleugenol and its elimination from serum. Environ Health Perspect 2004;112(6):678-680. 15121510




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