Isoeugenol

The leaves of Japanese red pine (Pinus densiflora Sieb. et Zucc.)

Molecular interactions of active constituents of essential oils in zwitterionic lipid bilayers.[Pubmed:29596800]

Chem Phys Lipids. 2018 Jul;213:76-87.

Eugenol and its related compounds are major active constituents of essential oils and have been extensively used as food flavoring agents with significant lipid peroxidation inhibition activity, highlighting the importance of understanding detailed molecular mechanisms behind their interactions with lipid bilayer. For this, we studied antioxidant activity of essential oils rich extract of Cinnamomum tamala leaves and molecular dynamics simulations of eugenol, Isoeugenol, methyleugenol, acetyleugenol and eugenol oxide in POPC and PLPC lipid bilayers. All the compounds penetrated into bilayer however, Isoeugenol showed highest affinity for the pure POPC and PLPC bilayers with lowest free energy profiles, formed more H-bonds with bilayer oxygen atoms and more pronounced changes in area per lipid and thickness of the bilayer, thus more efficient for scavenging radicals coming from outside as well as centrally located lipid peroxyl radicals. These molecular interactions rationalize the difference in inhibition activities of lipid peroxidation by eugenol and its related compounds.

Field Trapping Bactrocera latifrons (Diptera: Tephritidae) with Select Eugenol Analogs That Have Been Found to Attract Other 'Non-Responsive' Fruit Fly Species.[Pubmed:29723960]

Insects. 2018 May 1;9(2). pii: insects9020050.

Bactrocera latifrons (Hendel) (Diptera: Tephritidae) is a pest fruit fly species native to Oriental Asia which has invaded and established in Hawaii and Tanzania and has been recovered in detection trapping in California. It is largely non-responsive to the male lures cuelure and methyl eugenol. Alpha-ionol + cade oil is a moderately effective male B. latifrons attractant, but is not as attractive as cuelure or methyl eugenol are to other fruit fly species. An improved attractant is therefore desired. With the recent success in finding other non-responsive fruit fly species attracted to Isoeugenol, methyl-Isoeugenol, or dihydroeugenol in Australia and other countries, we wanted to assess whether B. latifrons might also respond to these “eugenol analogs.” Working with wild B. latifrons populations in Hawaii, we assessed the relative catch of B. latifrons in traps baited with the eugenol analogs with catch in traps baited with alpha-ionol, alpha-ionol + cade oil, or alpha-ionol + eugenol. Catch was significantly higher in traps baited with alpha-ionol + cade oil relative to traps with any of the other baits. There was, though, some male B. latifrons catch in traps baited with dihydroeugenol or Isoeugenol but none in traps baited with methyl-Isoeugenol.

Benzoxazine derivatives of phytophenols show anti-plasmodial activity via sodium homeostasis disruption.[Pubmed:29615339]

Bioorg Med Chem Lett. 2018 May 15;28(9):1629-1637.

Development of new class of anti-malarial drugs is an essential requirement for the elimination of malaria. Bioactive components present in medicinal plants and their chemically modified derivatives could be a way forward towards the discovery of effective anti-malarial drugs. Herein, we describe a new class of compounds, 1,3-benzoxazine derivatives of pharmacologically active phytophenols eugenol (compound 3) and Isoeugenol (compound 4) synthesised on the principles of green chemistry, as anti-malarials. Compound 4, showed highest anti-malarial activity with no cytotoxicity towards mammalian cells. Compound 4 induced alterations in the intracellular Na(+) levels and mitochondrial depolarisation in intraerythrocytic Plasmodium falciparum leading to cell death. Knowing P-type cation ATPase PfATP4 is a regulator for sodium homeostasis, binding of compound 3, compound 4 and eugenol to PfATP4 was analysed by molecular docking studies. Compounds showed binding to the catalytic pocket of PfATP4, however compound 4 showed stronger binding due to the presence of propylene functionality, which corroborates its higher anti-malarial activity. Furthermore, anti-malarial half maximal effective concentration of compound 4 was reduced to 490nM from 17.54microM with nanomaterial graphene oxide. Altogether, this study presents anti-plasmodial potential of benzoxazine derivatives of phytophenols and establishes disruption of parasite sodium homeostasis as their mechanism of action.

Appetite-enhancing effects of vanilla flavours such as vanillin.[Pubmed:29569223]

J Nat Med. 2018 Jun;72(3):798-802.

Vanilla flavour is familiar to consumers through foods, cosmetics, household products and some medicines. Vanilla flavouring agents typically contain vanillin or its analogue ethyl vanillin. Our previous study revealed that the inhalation of eugenol, which contains a vanillyl group, has an appetite-enhancing effect, and the inhalation of aroma compounds containing the vanillyl group or its analogues led to increased food intake in mice. Here, we found that vanillin, ethyl vanillin and eugenol showed appetite-enhancing effects, whereas Isoeugenol and safrole did not. These results suggest that the appetite-enhancing effects could be attributable to the vanillyl group and could be affected by the position of the double bond in the aliphatic chain. Furthermore, the results of intraperitoneal administration of eugenol and vanillin suggest that their appetite-enhancing effects could occur via stimulation of olfactory receptors.

Chemical Composition and Antioxidant Potential of Essential Oil and Organic Extracts of Euphorbia tithymaloides L. from Kushtia Region.[Pubmed:29493467]

Anticancer Agents Med Chem. 2018;18(10):1482-1488.

BACKGROUND: In the traditional system of medicine, leaves and stem bark of Euphorbia tithymaloides L. have been used for the treatment of asthma, persistent coughing, laryngitis, skin diseases and mouth ulcers. Some studies have reported the anti-inflammatory and antimicrobial activities of phytochemicals from the leaf; however, the analysis of essential oil and its antioxidant property is still unexplored. METHODS: This study evaluates the in vitro antioxidant potential of the essential oil and organic extracts from aerial parts of Euphorbia tithymaloides L. RESULTS: Thirty one compounds representing 96.37% of total oil were detected by GC-MS, of which eugenol (22.52%), phenyl ethyl alcohol (14.63%), 3-pentanol (9.22%), caryophyllene oxide (7.73%), Isoeugenol (7.32%), pentadecanol (5.14%), spathulenol (5.11%) and alpha-pinene (3.32%) were the major compounds. The oil and ethyl acetate extract displayed potent DPPH (IC50 = 13.67 and 17.59 microg/mL, respectively) and superoxide (IC50 = 21.83 and 42.34 microg/mL, respectively) radical-scavenging activities among all the tested samples. The oil and methanol extract also exhibited remarkable nitric oxide radical-scavenging activities (IC50 = 90.45 and 112.63 microg/mL, respectively) among other extracts. Furthermore, the methanol extract contained the highest amount of total phenolics as compared to other samples. CONCLUSION: The results demonstrate that the oil and extracts of E. tithymaloides could serve as natural antioxidants for using in pharmaceutical or cosmetic industries.

Efficient Mechanochemical Bifunctional Nanocatalysts for the Conversion of Isoeugenol to Vanillin.[Pubmed:29666790]

Front Chem. 2018 Apr 3;6:77.

A bifunctional nanocatalyst composed of iron containing SBA-15 material modified with sulfonic acid groups was synthesized by a mechanochemical approach. A full characterization of the obtained nanocatalyst was performed by N2 physisorption isotherms analysis, transmission electron microscopy (TEM), X-ray powder diffraction (XRD) and Fourier-Infrared Spectroscopy (FT-IR). The mechanochemically synthesized nanocatalyst displays a high Isoeugenol conversion to vanillin under mild conditions using H2O2 as oxidizing agent. Interestingly, this conversion resulted to be higher than that one obtained with the same material synthesized by an impregnation method. Additionally, the nanocatalyst showed excellent reusability over four successive runs under the studied reaction conditions.

Methyl-isoeugenol, a Highly Attractive Male Lure for the Cucurbit Flower Pest Zeugodacus diversus (Coquillett) (syn. Bactrocera diversa) (Diptera: Tephritidae: Dacinae).[Pubmed:29618022]

J Econ Entomol. 2018 May 28;111(3):1197-1201.

Effective male fruit fly attractants, such as cue lure (CL) and methyl eugenol (ME), are important in the monitoring and management of pest species through lure and kill techniques of trapping and male annihilation. However, some species are only weakly responsive to these lures, making their detection and control difficult. Zeugodacus diversus (Coquillett), a pest of cucurbit flowers in Asia, is weakly attracted to ME. Recently in Australia and Papua New Guinea, the eugenol analogues Isoeugenol, methyl-Isoeugenol, and dihydroeugenol were found to be effective attractants for species with a weak response to ME and CL, as well as several nonresponsive species. Additionally, studies from the early 1900s indicated that Z. diversus was attracted to Isoeugenol. To determine if these eugenol analogues may be more effective attractants for Z. diversus, we field tested them in Bangladesh in comparison to ME, as well as CL and zingerone. Z. diversus was significantly more attracted to all three eugenol analogues than ME, with it most attracted to methyl-Isoeugenol. Its attraction to methyl-Isoeugenol was 49 times greater than its attraction to ME (respective means 23.58 flies/trap/day (FTD) and 0.48 FTD). Z. diversus was also consistently trapped at methyl-Isoeugenol at all trap clearances including when populations were low, whereas it was only trapped at ME at 6 out of the 13 clearances. This study demonstrates that methyl-Isoeugenol is a highly attractive lure for Z. diversus and would be a valuable inclusion as an attractant in monitoring and male annihilation programs.

Isoeugenol is an essential oil constituent of nutmeg, clove, and cinnamon. Isoeugenol inhibits growth of Escherichia coli and Listeria innocua with MICs of 0.6 mg/mL and 1 mg/mL, respectively.

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