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Glimpse of eugenol in cloves Desember 28, 2012

Posted by priyosetyoko in Uncategorized.

            The spice known as clove  is the dried flowerbud of the clove tree, Eugenia caryophyllata Thunb. (=Syzygium aromaticum  (L.) Merr. & L.M. Perry) (Myrtaceae), which has a nail-like appearance leading to its vernacular names in several languages such as Dutch (nagel), Spanish (clavo and Portugese (cravo). Clove, native to the small islands of Maluku in Eastern Indonesia also known as the “Spice Islands”, has been traded from one end of the World to the other, being a highly sought afte commodity in medieval Europe for medicinal and culinary purposes. During the fourteenth century the clove trade acted as a stimulant in the establishment of commerce at ports especially in Asia and Europe where it was traded for large profits.  The high clove trade price inspired exploration expeditions in the search for new sources of this highly praised spice and the establishment of new sea routes. Throughout the following centuries its trade  went through several phases such as increased trade prices, struggle over control of the industry, warfare, decreased trade prices and even smuggling of seedlings for cultivation.

             Eugenol is an extraordinarily versatile molecule and has been included as an ingredient in cosmetics and several popular perfumes, for example Opium® and Kouros® by Yves Saint Laurent, as a spicy flavourant in whisky, ice cream, baked  goods and candy in restricted concentrations, mouthwashes, pharmaceutical and dental preparations. In dentistry it is used in combination with zinc oxide to form a polymerised eugenol cement used for surgical dressings, temporary fillings, pulp capping agents and cavity liners. Eugenol is the key ingredient in clove cigarettes unique to Indonesia, known as kretek. These cigarettes were extremely popular and about 10 billion were produced in 1939, 20 billion in 1972 and 67 billion in 1982, but their use has declined sharply due to reports of deleterious health effects. Eugenol was the first natural compound used in the synthesis of vanillin during the late 19th and early 20th century. However, most vanillin nowadays is produced from phenol or lignin. Eugenol is also used as an industrial source to produce isoeugenol and methyleugenol.

              The name eugenol originated from the scientific name of cloves: Eugenia aromaticum or Eugenia caryophyllata. Essential oil extracted from the cloves contains almost 72–90% eugenol. Cloves are widely grown in Indonesia, Madagascar and also in other countries like India and Sri Lanka.  Further, aromatic plants like  Cinnamomum tamala,  Myristica fragrans,  Melissa officinalis,  Ocimum basilicum, Ocimum tenuiflorum, Illicium anisatum and  Cinnamomum verum also contain eugenol . Eugenol is a member of the allyl-benzene class of chemical compounds. It is an allyl chain-substituted guaiacol. Guaiacol is naturally occurring organic compound with the formula C6H4(OH) (OCH3). It appears as a clear to pale yellow oily liquid. Eugenol is generally well soluble in organic solvents and it is sparingly soluble in water. Eugenol is reported to possess anticancer activity against various cancers. Additionally, the molecular mechanism of eugenol-induced apoptosis in melanoma, osteosarcoma, leukemia, gastric, skin tumors and mast cells has been well documented. The current review will delineate the antiproliferative activity and molecular mechanism of the eugenol-induced apoptosis in the above-mentioned cancer types.


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