Preparation of mesoporous silica nanoparticle with tunable pore diameters for encapsulating and slowly releasing eugenol
Tianlu ZhangZhiguo LüJianze WangJie ShenQiulian HaoYan LiJun YangYunwei NiuZuobing XiaoLei ChenXin Zhang
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Abstract Effects of eugenol esters with different alkyl chain lengths and combinations of eugenol + eugenol esters on sunflower oil oxidation at 338, 358, and 378 K are evaluated by determining different kinetic parameters. Also, water content and reverse micelles size of sunflower oil samples are monitored during oxidation. Eugenyl acetate shows higher antioxidant activity than eugenol in sunflower oil, while eugenyl butyrate, eugenyl hexanoate, and eugenyl decanoate shows lower antioxidant activity than eugenol. Antioxidant activity of eugenol esters decreases by increasing their alkyl chain length. Eugenol shows a synergistic effect with eugenyl acetate and eugenyl butyrate on increasing the induction period and antioxidant activity values, while it shows an antagonistic effect with eugenyl hexanoate and eugenyl decanoate. Also, combinations of eugenol + eugenyl acetate, as well as, eugenol + eugenyl butyrate stabilize the reverse micelles at longer period of time (3263 min for eugenol + eugenyl acetate and 2900 min for eugenol + eugenyl butyrate) than eugenol (2750 min). In addition, eugenol + eugenyl acetate and eugenol + eugenyl butyrate decrease the magnitude of temperature‐related effects on sunflower oil oxidation to the higher extent than eugenol did. Practical applications : Recent studies have suggested that the antioxidants with ability to locate at the active sites of lipid oxidation can efficiently reduce lipid oxidation in bulk oil. Despite a remarkable focus on antioxidant activity of eugenol, there is no information regarding improving its interfacial performance through esterification method. Also, there are few published data regarding the effects of esterified antioxidants on physicochemical changes during the oxidation of bulk oil. In this study, eugenol is esterified with anhydrides with different alkyl chain lengths to increase its accessibility to the active site of lipid oxidation, that is, water–oil interface of reverse micelles in sunflower oil. Effects of eugenol esters on stability of reverse micelles and critical reverse micelles concentration of lipid hydroperoxides have been investigated for the first time.
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Methyl eugenol
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Abstract Given the insecticidal potential of eugenol as a fumigant, this work aimed to determine the diffusion coefficient of eugenol emanating from a pure standard solution (99%), as well as from clove essential oil ( Eugenia caryophillata Thunb. (Myrtaceae)) through rice grain; to chemically analyse the volatile composition of commercially available eugenol and clove essential oil; and to evaluate the mortality of Sitophilus zeamais Motschulsky (Coleoptera: curculionidae) after exposure to eugenol inside a test chamber filled with rice. The solid phase microextraction method of extracting and quantifying eugenol by gas chromatography presented a good analytical response for the quantification of the analyte. There was no significant difference between the diffusion coefficient of eugenol diffusing from pure eugenol or from clove essential oil. The diffusion coefficient of eugenol through rice with the conditions herein adopted is 1.09 × 10 −3 cm 2 s −1 . The characterization of clove essential oil confirmed the presence of eugenol as its major component (74.25%). A difference was observed in the composition of the distinct phases evaluated. The exposure of adult S. zeamais to diffused eugenol from pure eugenol over seven days resulted in significantly higher mortality rates (~37%) than eugenol diffused from clove essential oil (~11%). No differences in mortality rates were observed in individuals placed at different positions inside the test chamber during eugenol fumigation.
Methyl eugenol
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Eugenol "purified" by HPLC20 was compared to commercial USP eugenol to determine if any difference exists between the inflammatory response caused by each. Mixtures of each eugenol with zinc oxide were also compared. Each material was injected subcutaneously beneath the abdominal skin of 40 Walter Reed white rats. Ten animals were sacrificed at four different dates, and the degree of necrosis and inflammation was compared. The purified eugenol caused less necrosis and inflammation at all times than did the commercial eugenol. The purified ZOE mixture produced less necrosis and inflammation than the commercial ZOE mixture at each sacrifice date. The two mixtures of ZOE and the two samples of eugenol produced roughly parallel amounts of inflammation, suggesting that the degree of inflammation of ZOE mixtures is strongly influenced by the amounts of free eugenol in the mixtures. This study suggests that the impurities in commercial eugenol do cause an increase in the inflammatory response in the rat system studied. This increase is most evident at day two and after day ten.
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본 연구는 한방스킨의 원료로 널리 사용되고 있는 8가지 생약의 휘발성증류추출액 중 항산화 및 항염증활성이 가장 강한 정향의 증류추출액으로부터 주된 향기성분을 SDE법으로 추출한 후 GC-MS로 확인하였으며, 주된 향기성분인 eugenol과 그 유도체를 합성한 후 항산화 및 항염증활성을 측정하고 비교하였으며, 아울러 HPLC를 이용하여 정향의 eugenol 및 그 유도체를 정량분석 하였다. 8가지 생약의 휘발성증류추출액 중 정향의 증류추출액이 가장 강한 항산화활성(ICsub50/sub=8.85 μg/mL) 및 COX-2 저해활성(10 μg/mL 농도에서 저해율은 58.15%)을 나타내었으며, 반면 15-LOX 저해활성(25 μg/mL 농도에서 저해율은 86.15%)은 당귀 다음으로 가장 높았다. 정향 증류추출액의 휘발성 향기성분을 SDE법으로 추출한 후 GC-MS를 이용하여 분석한 결과, eugenol, trans-caryophyllene 및 acetyl eugenol을 확인하였다. 한편, eugenol 및 그 유도체(methyl eugenol 및 acetyl eugenol)의 항산화 및 항염증 활성을 측정한 결과, eugenol(ICsub50/sub=5.99 μg/mL)이 가장 높은 항산화활성을 나타낸 반면, methyl eugenol 및 acetyl eugenol은 거의 활성을 나타내지 않았다. COX-2의 경우 20 μg/mL 농도에서 eugenol(85.35%)이 가장 강한 저해활성을 나타낸 반면, 15-LOX는 20 μg/mL 농도에서 methyl eugenol(83.29%)이 가장 높은 저해활성을 나타내었다. 정향 에탄올추출물의 eugenol 및 유도체의 함량을 HPLC로 분석한 결과, eugenol 및 acetyl eugenol이 각각 6.95%, 1.85% 함유되어 있었으며 methyl eugenol은 검출되지 않았다. 이와 같이 정향 유래의 eugenol 및 그 유도체는 안전성이 문제시되고 있는 합성항산화제 및 항염증제를 대체할 수 있는 천연 유래의 항산화 및 항염증물질로서 잠재적 가치가 있어 향후 기능성식품, 화장품 및 의약품 소재로 널리 사용될 수 있을 것으로 생각된다.
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In connection with an investigation of the correlation between s tructurc and reactivity of eugenol isomers, o-eugenol, 3-allyl-2-methoxyphenol and chavibctol were synthcs ized.A five-step synthesis was found to be most suitable for the preparation of 3-ally l-2-mcthoxyphe nol.An improved separation of chavibetol from euge nol was achicved by gas chromatography. I I.' ~ 1 Th~ researr h work wnssupported by
Reactivity
Methyl eugenol
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The aim of this study was to investigate the effect of peroxidase on eugenol and its modification which results with formation of insoluble compounds that can be easily removed from the clove essential oil. This reaction could be potentially used for the removal of eugenol from various samples. According to the obtained results it can be concluded that peroxidase affects eugenol and causes its modification which has been confirmed using spectrophotometric and chromatographic techniques. The results show that time of reaction between clove essential oil and enzyme is proportional to the degree of eugenol degradation, and that four hour reaction results with almost full disaperance of eugenol from oil sample (degradation of 93%).
Degradation
Methyl eugenol
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A laboratory experiment was conducted to quantify the eugenol in seeds primed with plant based eugenol (tulsi leaf extract, clove bud extract) and commercial eugenol, and also in the roots of resultant seedlings by developing and verifying a rapid and accurate Reverse Phase High-Pressure Liquid Chromatography method. The tomato, brinjal, and chilli seeds were primed (12hrs, 6hrs, and 12hrs respectively) with a standardized concentration of plant based and commercial eugenol. The different priming treatments such as T1-Control, T2-Hydropriming, T3-Purple tulsi extract (3%), T4-Clove bud extract (2%), and T5-Commercial eugenol (0.25%) were adopted in this experiment. The results revealed that the maximum quantity of eugenol was recorded in seeds as well as roots of tomato and brinjal which were primed with clove bud extract (2%), whereas in chilli, the seeds primed with commercial eugenol (0.25%) followed by clove bud extract (2%) recorded the maximum quantity of eugenol in seeds and roots of resultant seedlings, respectively. Eugenol content was absent in control and hydroprimed seeds and seedlings (root). The results also indicate that more than 90 per cent of eugenol was transferred from primed seeds to the roots of all three crops in the case of plant based eugenol.
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To test the anesthetic effect of emulsified eugenol to Cyprinus carpio Linnaeus, eugenol was emulsified with Tween 80, Span 80, ethanol and water. Then the start time, time length of anesthesia and LD50 of emulsified eugenol to Cyprinus carpio Linnaeus was determined contrastively with alcoholic eugenol. Results showed that the start time of anesthesia of emulsified eugenol was longer than these of alcoholic eugenol under the same concentration of eugenol. The time length and LD50 of anesthesia of emulsified eugenol were five times longer and 2.15 times large respectively than that of alcoholic eugenol. So, the anesthetic effect of emulsified eugenol on Cyprinus carpio Linnaeus was slower, gentler, longer and safer than alcoholic eugenol. It was more proper to be applied for fish farming than alcoholic eugenol as a fish anesthetic agent.
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Eugenol is a phytochemical present in herbal and medicinal plants. It possess anti tubercular, anti-inflammatory, anti-mutagenic properties. Commercial or synthesised eugenol is used extensively in the market nowadays. The aim is to evaluate the anti-microbial property of eugenol extracted from both the powder and leaf samples of Ocimum sanctum (tulsi) and to have a comparative analysis of the synthetic eugenol and the naturally extracted eugenol from tulsi leaves. The eugenol is extracted from tulsi leaves by steam distillation. For quantitative analysis of the natural eugenol, HPLC and UV Spectroscopy are performed with commercial eugenol as the reference. While Raman Spectroscopy is performed for qualitative analysis of the constituents of tulsi leaves. Membrane casting is done with eugenol as the core ingredient and porosity of the membrane is checked by SEM. Further microbial assay is performed to evaluate the effect of eugenol. From the results it can be concluded that the eugenol extracted from the powder and fresh leaves of tulsi has anti-microbial effect and the membrane composed of eugenol has the capability to retain the eugenol. Keywords: Ocimum sanctum, eugenol, anti-microbial, membrane,anti-microbial.
Phytochemical
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Achieving particle size control and pore size control is crucial when utilizing mesoporous silica to perform fundamental studies. Pore size can be controlled by adjusting the reaction condition during the synthesis of mesoporous silica. Here realizing that different sizes of particles fall at different speeds in the liquid, we achieve a narrow particle size selection through the sediment of the mesoporous silica in water. By applying particle size selection on mesoporous silica with different pore sizes, silica particles with the exact pore sizes but different particle sizes, or with varying sizes of pore but exact particle sizes are obtained.
Particle (ecology)
Mesoporous organosilica
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