The Multiple Faces of Eugenol. A Versatile Starting Material and Building Block for Organic and Bio-Organic Synthesis and a Convenient Precursor Toward Bio-Based Fine Chemicals

Kaufman, Teodoro S.

doi:10.5935/0103-5053.20150086

Cited by 44 publications

(48 citation statements)

References 2 publications

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“…& Perry (Myrtaceae)], shows relevant pharmacological activities, especially the antibacterial and antifungal actions [11]. Some authors have described the synthesis of eugenol derivatives in order to optimize its activities.…”

Section: Introductionmentioning

confidence: 99%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b , 5c, and 5d ) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b and 5d ) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.

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Section: Introductionmentioning

confidence: 99%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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“…Nevertheless, low stability with light and high temperatures partially limits the therapeutic use of eugenol. For this reason, the esterification of the phenolic hydroxyl group has been suggested to create more stable bioactive derivatives . With this perspective, the enzymatic approach herein described can be considered of great interest.…”

Section: Resultsmentioning

confidence: 99%

“…The efficiency of this compound in therapeutic treatments is limited by its poor water solubility, however . Nevertheless, in virtue of its easy access and polyfunctional structure, it is considered as a useful starting material to produce valuable derivatives through chemical synthesis and biotransformation . Biotechnological approaches based on the use of hydrolytic enzymes as biocatalysts have been proven efficient for the preparation of many attractive esters; despite this, applications of hydrolases on an industrial scale remain limited.…”

Section: Introductionmentioning

confidence: 99%

“…2 Nevertheless, in virtue of its easy access and polyfunctional structure, it is considered as a useful starting material to produce valuable derivatives through chemical synthesis and biotransformation. 1,3,4 Biotechnological approaches based on the use of hydrolytic enzymes as biocatalysts have been proven efficient for the preparation of many attractive esters; 5 despite this, applications of hydrolases on an industrial scale remain limited. In general, the systems that have been developed suffer from high operational costs that make scaling-up difficult.…”

Section: Introductionmentioning

confidence: 99%

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Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Giovannini

Catani

Massi

et al. 2019

Flavour & Fragrance J

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The enzymatic synthesis of biologically active compounds is receiving increasing interest from academic and industrial researchers. Herein, we report on the continuous‐flow enzymatic production of eugenol esters with packed‐bed microreactors prepared with the Novozym 435 and Lipozyme RM IM lipases. After optimization of the independent process variables, namely temperature (68 °C), flow rate (8 μL min−1), and eugenol/isobutyric anhydride molar ratio (1 : 5) by means of experimental design methodologies, the unprecedented continuous‐flow production of eugenyl isobutyrate has been achieved with steady‐state conversions of 77 and 70%, using packed‐bed microreactors prepared with Novozym 435 and Lipozyme RM IM, respectively. With acetic anhydride as the acylating agent, the same reactors, under the same conditions, afforded eugenyl acetate with steady‐state conversions of 82% (Novozym 435) and 90% (Lipozyme RM IM). The two ester products have been tested against phytopathogenic and dermatophytic fungi, demonstrating interesting action against dermatophytic fungi. The reported results demonstrated the suitability of the enzymatic packed‐bed microreactors as a sustainable and scalable technology for the solvent‐free continuous‐flow production of biologically active esters of eugenol.

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“…They are well-known naturally occurring phenolic monoterpenoids found primarily in oils of oregano, thyme, and marjoram, and are recognized as traditional therapeutic agents [16,17]. All the major groups of angiosperms biosynthesize these biocides [18]. Currently, these biocides are used in food flavouring ingredients and preservatives, as well as a fragrance ingredients in cosmetic formulations [19].…”

Section: Introductionmentioning

confidence: 99%

Comparative Anti-Proliferative Studies of Natural Phenolic Monoterpenoids on Human Malignant Tumour Cells

Rajput¹,

Bagul²,

Tadavi³

et al. 2016

Med Aromat Plants

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In present study we report prominent effect of carvacrol (5-isopropyl-2-methyl phenol), thymol (2-isopropyl-5-methyl phenol) and eugenol (4 allyl-2-methoxyphenol) on Human melanoma cells. These three compounds were screened for Anti-proliferative test by using Sulforhodamine B (SRB) assay. For this investigation we used human breast melanoma cell line MCF-7, human skin melanoma cell line SK-MEL-2, human colon melanoma cell line HCT-15 and human pancreatic melanoma cell line MIAPaCa-2. Carvacrol was identified as most potent molecule with low GI 50 value as 0.1 μL for selected human cancer cell lines; which is comparatively equal to standard drug 14 Adriamycin (ADR). Thymol and Eugenol also exhibited remarkable GI 50 for human cancer cell 15 lines.

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The Multiple Faces of Eugenol. A Versatile Starting Material and Building Block for Organic and Bio-Organic Synthesis and a Convenient Precursor Toward Bio-Based Fine Chemicals

Cited by 44 publications

References 2 publications

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Comparative Anti-Proliferative Studies of Natural Phenolic Monoterpenoids on Human Malignant Tumour Cells

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