Relationship between eugenol and isoeugenol derivatives

relationship between eugenol and isoeugenol derivatives

STRUCTURE – ANTIOXIDANT ACTIVITIES RELATIONSHIP ANALYSIS OF ISOEUGENOL, EUGENOL, VANILIN AND THEIR DERIVATIVES. Evaluation of the antibacterial activity of eugenol derivatives using the inhibition zone technique, . Isoeugenol, NA, NA, , NA, NA, NA In the specific case of eugenol, the relationship between the hydroxyl group and the. Infrared and Raman Spectroscopy of Eugenol, Isoeugenol, and Methyl Eugenol: Conformational Analysis and Vibrational Assignments from.

Therefore, this work carried out the synthesis, purification, characterization, and evaluation of the antioxidant and antibacterial potential of 19 eugenol derivatives. In addition, the derivatives were active against bacterial strains Escherichia coli, Staphylococcus aureus that eugenol itself showed no activity, thus increasing the spectrum of antibacterial action. Electronic supplementary material The online version of this article Introduction Molecular modification in structures of biologically active substances that occur naturally is one of the main strategies to enhance healthy biological effects, as well as to reduce eventual side effects [ 1 — 3 ].

More recent data December show that of the drugs used as anti-infectious agents antibacterial, antifungal, parasitic, and antiviralexcluding vaccines, recognized by public health agencies in the world, approximately Thus, it is clear that this is a line of research with great potential for obtaining new drugs [ 5 ].

Eugenol, a natural substance used as a target molecule for the manufacture of bioactive compounds, was first isolated in and its commercial production began in in the United States. It can be produced synthetically; however, it is mainly extracted from Ocimum tenuiflorum, Cassia fistula, Zieria smithii, and Pimenta racemosa.

Eugenol and Isoeugenol Derivatives Group - information sheet

Classified as a phenylpropanoid of the allyl-phenol type, eugenol is a pale yellow oil with clove odor and spicy taste. With numerous applications in the pharmaceutical, food, agricultural, and cosmetics industries [ 67 ], it showed promising antimicrobial and antioxidant effects [ 8 — 12 ], when evaluated against the fungi Cladosporium spp. Other activities are reported in literature, such as antiviral [ 1415 ], anti-inflammatory [ 16 ], and inhibitor of platelet aggregation [ 17 ].

relationship between eugenol and isoeugenol derivatives

In addition, its anti-Leishmania activity together with its low cytotoxicity qualifies it as a promising source of new leishmanicidal [ 18 ]. Together with other spice constituents, eugenol is under detailed investigation for its biological effects in the human body [ 1415 ]. Eugenol 1 isomer, namely isoeugenol 2 and methyl eugenol 3 also play vital role in devolvement of organic, medicinal, natural products, and carbohydrate chemistry. Isoeugenol 2 has been widely used as a key molecule for development of organic synthetic methodologies; similarly methyl eugenol 3 is used as a flavor in many food products, as a fragrance ingredient in perfumes, toiletries, and detergents, and as insect attractant in some pesticide formulations.

As such Eugenol is commercially available in large quantities [ 1617 ]; and the specific structure and ready availability of eugenol has turned this natural product into an interesting starting material, a useful building block for complex synthesis, as well as a valuable substrate for various biotransformations [ 18 ]. The current review will highlight the medicinal biography of eugenol and its derivatives.

Eugenol and Isoeugenol Derivatives Group -

Occurrence of Eugenol Being a major component of clove; taste of clove is imparted by the chemical eugenol [ 19 ]. Eugenol is a compound found in certain plants, such as basil, cinnamonlemon balm, and nutmeg, however, it is primarily extracted from clove plants. Cloves are used in Indian ayurvedic medicine, Chinese medicine, and western herbalism and dentistry ; where the essential oil is used as an anodyne painkiller for dental emergencies.

Cloves are used as a carminative, to increase hydrochloric acid in the stomach and to improve peristalsis. Cloves are also said to be a natural anthelmintic [ 21 ].

The various basils have similar diverse scents, as the herbs have number of different essential oils that come together in different proportions in variety of breeds. The strong clove scent of sweet basil is derived from eugenol, the same chemical as actual cloves.

relationship between eugenol and isoeugenol derivatives

The flavor of cinnamon is due to eugenol, mostly found in the leaves [ 22 ] Figure 1. Isolation of Eugenol Eugenol, the principal ingredient in clove oil, is a familiar aroma in many dental offices as it is frequently mixed into a paste and used in medicines [ 2324 ].

It is clear pale yellow oil with a warm, pungent, yet pleasing aroma as the smell of bay leaves and clove. Generally, eugenol is isolated from clove oil; as concentration of eugenol in it is high up to Clove is one of the most important herbs in traditional medicine and its scientific name is Syzygium aromaticum.

Eugenol and Isoeugenol Derivatives Group - information sheet -

Commercial eugenol is derived by steam distillation and refinement of oil of clove bud and leaf, cinnamon leaf or basil [ 2627 ]. Cinnamomum zeylanicum is one of the oldest herbal medicines mentioned in Chinese texts years ago [ 28 ]. Holy Basil Ocimum sanctum is one of the most widely grown herbs for therapeutic use [ 3031 ].

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Hahn and Burkett reported extraction of eugenol from different preparations of Holy Basil [ 32 ]. Biologically Active Synthetic Derivatives of Eugenol In Recent years, the derivatives synthesized from natural products have been found to possess huge biological activities. Eugenol is interesting naturally occurring phenolic monoterpene belonging to phenylpropanoids group, having versatile actions against bacteria, pathogens and harmful microorganisms.

Currently world reputed organizations have taken interests in drug discovery particularly of natural origin. Which showed potential human tumor cell growth inhibitory effect [ 33 ]. Accompanying studies on the structure-activity relationships are mainly associated to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring [ 35 ].

Ether derivatives possessing alkyl or aryl groups substituting the hydroxyl group 19 presented promising activities as compared to the esters of eugenol [ 37 ]. For comparative purposes the study was also extended on six naturally occurring eugenol analogues [ 38 ]. All the derivatives found to inhibit PGE2 and collagen induced platelet aggregation in different extent of series [ 39 ].

Eugenol ether 32 has been proved to have a beneficial effect, protecting injured ECV cells with an EC50 value of 0. Rugulactone, a natural pyrone found in Cryptocaria Rugulosa, which is important factor for inhibition of NK-kB and this factor plays vital role in DNA sequencing [ 42 ]. The compounds synthesized were evaluated for antileishmanial activity against L. A number of substituted cinnamylphenol derivatives 42 containing eugenol moiety have been reported by Ito et al.

A new series of 1,3,5-trisubstituted pyrazolines 44 has been synthesized by Bhat et al. The synthesized derivatives exhibited significant antibacterial activities compared to gentamycin and moderate antifungal activity in comparison with griseofulvin [ 48 ].