• Title/Summary/Keyword: Acetone cation

Search Result 40, Processing Time 0.025 seconds

Photocyclization Reactions of N-(Trimethylsilylmethoxyalkyl)Phthalimides. Efficient and Regioselective Route to Heterocycles

  • Yoon Ung Chan;Oh Ju Hee;Lee, Sang Jin;Kim, Dong Uk;Lee, Jong Gun;Kang Kyung-Tae;Mariano Patrick S.
    • Bulletin of the Korean Chemical Society
    • /
    • v.13 no.2
    • /
    • pp.166-172
    • /
    • 1992
  • Studies have been conducted to explore single electron transfer (SET) induced photocyclization reactions of N-(trimethylsilylmethoxyalkyl)phthalimides(alkyl=E thyl, n-propyl, n-butyl, n-pentyl, and n-octyl). Photocyclizations occur in methanol in high yields to produce cyclized products in which phthalimide carbonyl carbon is bonded to the carbon of side chain in place of the trimethylsilyl group. Mechanism for these photocyclizations involving intramolecular SET from oxygen in the $\alpha-silylmethoxy$ groups to the singlet excited state phthalimide moieties followed by desilylation of the intermediate $\alpha-silylmethoxy$ cation radicals and cyclization by radical coupling are proposed. In contrast, photoreaction of N-(trimethylsilylmethoxyethyl) phthalimide in acetone follows different reaction routes to produce two cyclized products in which carbon-carbon bond formation takes place between the phthalimide carbonyl carbon and the carbon $\alpha$ to silicon and oxygen atoms via triplet carbonyl hydrogen abstraction triplet carbonyl silyl group abstraction pathways. The normal singlet SET pathway dominates these triplet processes for photoreaction of this substance in methanol. The efficient and regioselective cyclization reactions observed for photolysis in methanol represent synthetically useful processes for construction of medium and large ring heterocyclic compounds.

Isolation of Alliin in Garlic and Its Quantitative Determination by High Performance Liquid Chromatography and Studies on the Antimicrobial Efforts of Alliin and Ethanol Extracts from Korean Garlic(Alliium sativum L.) (마늘 중 고속 액체 크로마토그래피에 의한 알린의 분리 및 정량과 Alliin과 에탄올 추출물의 항균효과에 관한 연구)

  • 위성언
    • The Korean Journal of Food And Nutrition
    • /
    • v.16 no.4
    • /
    • pp.296-302
    • /
    • 2003
  • First. the purification and analysis of alliin in garlic from different origins by alliin-HPLC determination method were studied. Allinase in garlic was inactivated by heating in boiling water followed by extraction of alliin in garlic with 80% methanol. To remove free amino acids and alliin homologs in garlic, garlic extract was separated by cation exchange column which was packed with amberlite CG-120 resin using 40L d-water as eluent. Alliin in garlic extract was crystallized in a mixture of acetone (50$^{\circ}C$):H$_2$O:acetic acid=70:29:1 and then recrystallized in a mixture of acetone (50$^{\circ}C$):H$_2$O:acetic acid=75:24:1. Obtained alliin was identified by melting point. TLC, microscope observation and mass spectrometry. High performance liquid chromatography (HPLC) following pre-column derivatization of cystein derivatives with o-phthaldialdehyde/2-mercaptoethanol has succeessfully been applied to the analysis of various garlics. Each alliic of standard solution and garlic extract was derivatized to isoindole derivative by o-phthaldialdehyde /2-mercaptoethanol and then analyzed by HPLC. Six point calibration was done by using alliin peak area. Lineality was observed at 0 ∼ 1.0mg/ml of alliin concentration. Weighted regression line function was Y=6254X - 256077. By this function, alliin contents in various garlics were 0.34 ∼ 0.73% fresh weight. Second study was designed to evaluate the effects of garlic extracts of various concentrations on the growth of various pathogenes (Eubacterium limonsum, Bacteroides fragilis, Salmonella typhimurium, Salmonella typhi, Shigella sonnei, Kiebsiella pneumoniae, Enterobacter cloacae, Pserdomonas aeruginosa, Escherichia coli). For antimicrobial effects against microorganism, totally minimal inhibition concentrations (MIC) of alliin were from 5,000 to 20,000ppm. MIC of ethanol extract were 1,250 to 10,000ppm.

Screening of Biological Activity of Caragana sinica Extracts (골담초(Caragana sinica) 추출물의 생리활성 탐색)

  • Jeon, Young-Suk;Jo, Bun-Sung;Park, Hye-Jin;Kang, Sun-Ae;Cho, Young-Je
    • Journal of the Korean Society of Food Science and Nutrition
    • /
    • v.41 no.9
    • /
    • pp.1211-1219
    • /
    • 2012
  • In this study, extracts from Caragana sinica flowers and leaves were tested for antioxidant and angiotensin converting enzyme inhibitory activities, along with xanthine oxidase, tyrosinase, elastase, and astringent effects. Total phenolic compounds of acetone extracts from Caragana sinica flowers and leaves were the highest at 3.42 and 2.98 mg/g, respectively, when various extraction solvents were used. Optimal conditions for extraction of phenolic compounds from Caragana sinica leaves and flowers were 70% ethanol for 18 hr. DPPH scavenging activities were the highest in 70% ethanol extracts of Caragana sinica. ABTS radical cation decolorization values of 70% ethanol extracts were higher than those 60% ethanol extracts at 74%. Antioxidant protection factor was 1.2 PF in 70% ethanol extracts from Caragana sinica flowers and leaves. TBARS was lower than that of control (0.54 ${\mu}M$) in all sections. Angiotensin converting enzyme inhibitory activity of Caragana sinica flower extract was 80~90% at a phenolic concentration of 0.2~1.0 mg/mL, whereas xanthin oxidase inhibitory activity of Caragana sinica leaf extract was higher than that of flower extract. Tyrosinase inhibitory activity, which is related to skin-whitening, was above 20%, whereas elastase inhibitory activity related to anti-wrinkle effect was above 50% at a phenolic concentration of 0.8 mg/mL. Astringent effects of Caragana sinica flower and leaf extracts were higher than tannic acid as a control at an equivalent concentration. This result suggests that extracts from Caragana sinica flowers and leaves are suitable as functional foods having anti-hypertension, anti-gout, and medicinal cosmetic activities, including whitening and anti-wrinkle effects.

Complex Formation of Substituted Benzo-1,4,7,10,13-pentaoxacyclopentadecane (B15C5) with Nd(Ⅲ) (Nd(Ⅲ)과 치환된 Benzo-1,4,7,10,13-pentaoxacyclopentadecane (B15C5)와의 착물 형성에 관한 연구)

  • Kim, Hae-Joong;Kim, Jeong;Kim, Si-Joong
    • Journal of the Korean Chemical Society
    • /
    • v.39 no.6
    • /
    • pp.440-445
    • /
    • 1995
  • The chemical compositions and stability constants, thermodynamic parameters for the neodymium(Ⅲ) complexes of substituted benzo-1,4,7,10,13-pentaoxacyclopentadecane(B15C5) have been determined by spectrophotometry and conductometry in methanol solution at various temperatures. As substituents, CH3, Br, CHO, NO2, and 3,4-(NO2)2 were used. In methanol solution the ratios of neodymium(Ⅲ) to the ligands in the complexes are 1 : 1. The stability constants were increased in order of B15C5-3,4-(NO2)2 < B15C5-NO2 < B15C5-CHO < B15C5-Br < B15C5 < B15C5-CH3. This observation can be explained in terms of the substituent effect. The order of stability constants was dimethylsulfoxide < acetone < acetonitrile in solution and the magnitudes were found to be inversely proportional to the solvents donicities. These results could be understood in terms of solvent basicity, ligand basicity, solvation of the cation, and entropy changes of complex formation.

  • PDF

Anti-wrinkle Effect of Chestnut Leaf (밤나무잎의 항주름 효과)

  • Jang, Min Jung;Jun, Dong Ha;Kim, Sea Hyun;Han, Sang Ik;Lee, Jin Tae
    • Journal of Life Science
    • /
    • v.23 no.6
    • /
    • pp.751-756
    • /
    • 2013
  • This research old age chestnut tree that loss function chestnut leaf renewal efficiency enlargement and development of cosmeceutical product by purpose. Chestnut leaf (CL) exhibits numerous pharmacological effect including anti-allergy and anti-microbial properties. However, the anti-wrinkle effect of CL is not completely understood. In this study, to find a possible explanation for the anti-wrinkle effects of CL, we evaluated the effects of CL on radical scavenging activity, elastase inhibition activity and collagenase inhibition activity. CL was extracted with various solvents including water (CLW), 70% ethanol (CLE) and 70% acetone (CLA). The results showed that CLW, CLE, and CLA have the radical scavenging activity. In addition, we showed that CLW, CLE, and CLA have the elastase inhibition activity and collagenase inhibition activity. Consequently, the CL has a potent anti-wrinkle effect and it could be a useful cosmeceutical product for anti-aging purposes.

Antioxidant Effects of Solvent Fraction from Sanguisorbae officinalis L. with Acetone (오이풀 아세톤 추출물을 이용한 용매 분획물의 항산화 효과)

  • Kim, Hui-Yeong;Yeo, Shin-Il;Lee, Jin-Tae
    • Journal of Applied Biological Chemistry
    • /
    • v.54 no.2
    • /
    • pp.89-93
    • /
    • 2011
  • The solvent extracts of Sanguisorbae officinalis L. were investigated for the activities of antioxidants as a functional ingredient for cosmetic products. The electron donating effect of ethyl acetate layer and n-butyl alcohol layer was appeared similar activity with positive control butylated hydroxy anisole (BHA) at all concentrations. In addition, in 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical scavenging assay, ethyl acetate layer, n-butyl alcohol layer and water layer were over 99% effect at all concentrations and higher than that of BHA. Also in hydrogen peroxide scavenging assay, ethyl acetate layer and n-butyl alcohol layer were higher than that of positive control ascorbic acid. The measured superoxide dismutase (SOD)-like activity of n-butyl alcohol was more than 50% at concentration of 1,000 ${\mu}g/mL$ and superoxide anion radical scavenging ability showed more than 45% at 1,000 ${\mu}g/mL$ of n-butyl alcohol layer. All these findings suggested that ethyl acetate layer and n-butyl alcohol layer have a great potential as a cosmeceutical ingredient with an antioxidant effect.

Flavonoid and Phenol Contents and Antioxidant Effect of Wine By-product Extracts (포도주 부산물의 총 플라보노이드와 총 페놀 함량 및 항산화 효과)

  • Baek, Jae Yeol;Lim, Sun-Young
    • Journal of Life Science
    • /
    • v.26 no.8
    • /
    • pp.948-954
    • /
    • 2016
  • We investigated the flavonoid and phenol contents and antioxidant effect of wine by-product extract. Antioxidant effects were measured with 1,1-diphenyl-2-picryhydrazyl (DPPH) and 2.2'-azino-bis(3-ethylbenothiazoline-6-sulfonic acid) diammonium salt radical cation (ABTS+) assays. Cellular reactive oxygen species (ROS) were measured with the dichlorofluorescein-diacetate (DCFH-DA) assay. The flavonoid and phenol contents of the methanol (MeOH) extract were greater than those of the acetone+methylene chloride (A+M) extract. Among fractions, the 85% aqueous methanol (85% aq. MeOH) fraction contained the highest flavonoid contents, while the n-BuOH fraction had more phenol contents. In the DPPH and ABTS assays, the MeOH extract showed a scavenging effect greater than that of the A+M extract (p<0.05). The n-BuOH fraction (0.5 mg/ml concentrations) showed scavenging effects of 72% and 92%, respectively, in the DPPH and ABTS assays (p<0.05). However, the 85% aq. MeOH fraction showed a 90% scavenging effect in the DPPH assay only. In 120 min ROS production assay, all tested fractions dose-dependently decreased cellular ROS production induced by H2O2 in comparison with that produced by exposure to the extract-free control. The MeOH extract showed a higher sinhibitory effect on cellular ROS producing than that of the A+M extract at all concentrations tested. Treatment with the n-BuOH fraction (0.1 mg/ml concentrations) inhibited cellular ROS production by 60%. These results indicate that the n-BuOH fraction of wine by-product extract inhibited cellular oxidation and may contain valuable bioactive compounds such as flavonoids and phenols.

Comparison of Flavonoid Content and Antioxidant Effect of Extracts from Stachys sieboldii Miq. and Lycopus lucidus Turcz (초석잠 및 택란 추출물의 플라보노이드 함량 및 항산화 활성 비교)

  • Lee, Jung Woo;Lim, Sun Young
    • Journal of Life Science
    • /
    • v.28 no.7
    • /
    • pp.841-848
    • /
    • 2018
  • The flavonoid content and antioxidant effects of extracts from Stachys sieboldii Miq. and Lycopus lucidus Turcz were compared. The flavonoid content of the acetone + methylene chloride (A+M) extract of L. lucidus Turcz was 233.2 mg/g, suggesting that the extract was greater than that of S. sieboldii Miq. In the DPPH assay and the A+M and methanol (MeOH) extracts from L. lucidus Turcz had greater scavenging effects than those of S. sieboldii Miq. (p<0.05). The A+M extract from L. lucidus Turcz (0.5 mg/ml concentration) had an 82% scavenging effect in the DPPH assay. In the ABTS assay, A+M extracts from both S. sieboldii Miq. and L. lucidus Turcz (0.5 mg/ml concentration) had scavenging effects of 90% and 88%, respectively (p<0.05), suggesting that both A+M extracts had greater scavenging effects than those of both MeOH extracts. In a 120 min ROS production assay, all tested extracts dose-dependently decreased the cellular ROS production that was induced by $H_2O_2$, as compared to those produced by exposure to the extract-free control. The A+M extracts from both S. sieboldii Miq. and L. lucidus Turcz had greater inhibitory effects on cellular ROS production than those of both MeOH extracts at all concentrations tested. Treatment with the A+M extracts from S. sieboldii Miq. and L. lucidus Turcz (0.25 mg/ml concentration) inhibited the cellular ROS production by 60% and 86%, respectively. These results suggest that the A+M extracts of Stachys sieboldii Miq. and L. lucidus Turcz inhibit cellular oxidation and may contain valuable bioactive compounds, such as flavonoids.

Functional Properties of Walnut in Cosmetics (호두의 화장품 기능성)

  • Kim, Mee-Kyung;Kim, Jin-Sung;Jo, Bun-Sung;Kim, Jeung-Hoan;Lee, In-Cheol;Lee, Myung-Sup;Cho, Young-Je
    • Journal of Life Science
    • /
    • v.21 no.6
    • /
    • pp.858-864
    • /
    • 2011
  • The phenolic compounds of walnut extracts by various solvents were shown to be 24.3 mg/g in hot water, 34.4 mg/g in ethanol, 32.5 mg/g in methanol and 15.1 mg/g in acetone. In a comparison of phenolic compounds from hot water and different concentrations of ethanol, which are harmless, 60% ethanol extract and hot water extract were 34.7 mg/g, 24.6 mg/g. The electron donating ability (EDA) of walnut extracts in hot water and 60% ethanol were 78.1% and 80.6%. According to ABTS radical cation decolorization for antioxidant activity, hot water and 60% ethanol extract showed high antioxidant activities of 98.1% and 98.3%. Antioxidant protection factor (PF) were $1.1{\pm}0.2$ PF and $1.1{\pm}0.4$ PF in hot water and 60% ethanol extract. In TBARs inhibitory activity, each extract showed high antioxidant activities at 60% and 75%. Anti-inflammation effects of walnut extract were tested, and inhibition of NO was 50% in 100 ${\mu}g/ml$ phenolics. Inhibitory activity against iNOS and COX-2 were shown, through Western blot, to be 10% in 100 ${\mu}g/ml$ phenolics. Tyrosine inhibitory activity of 60% ethanol extract was 43%, and astringent effect of 60% ethanol extract was 55%. These results suggest that walnut extracts are suitable for functional cosmetics requiring skin-whitening and anti-wrinkle activity.

Physicochemical Properties of the Synthetic Hectorite (합성 헥토라이트의 물리화학적 특성)

  • Chae, Soo-Chun;Jang, Young-Nam;Bae, In-Kook;Jang, Hee-Dong;Ryou, Kyung-Won;Chae, Young-Bae
    • Journal of the Mineralogical Society of Korea
    • /
    • v.21 no.3
    • /
    • pp.313-320
    • /
    • 2008
  • Hectorite was synthesized under hydrothermal conditions and its physicochemical properties have been investigated in terms of temperature, pH, and organic agent to observe the change of doll basal spacing. The IR, CEC, MB, swelling volume and specific surface area of the hectorite were measured for the characterization. The solid/liquid ratio of hectorite to distilled water before mixing with other materials was also determined for its use as a multi-functional material. The $d_{001}$ basal spacing decreased from $12.63\;\AA$ at room temperature to $10.19\;\AA$ at $650^{\circ}C$ in the heating tests. As the pH of hectorite slurry increased. the $d_{001}$ basal spacing decreased. reaching the lowest value of $13.33\;\AA$ at pH 7 and afterward, increased. All the fool basal spacings of the hectorite increased when it was intercalated with the following solvents: $12.86\;\AA$ in diethyl ether, $13.31\;\AA$ in acetonitrile. $13.59\;\AA$ in methanol, $14.05\;\AA$ in ethanol, $15.69\;\AA$ in acetone, and $17.42\;\AA$ in ethylene glycol. Our IR analysis results were in good agreement with those of other researchers. The CEC, MB, swelling volume and specific surface area of hectorite were determined to be 105 cmol/kg, 80 cmol/kg, $68\sim74ml/2g$ and $213m^{2}/g$, respectively. Also, the hectorite to distilled water ratio of 2 to 100 was found to be most favorable for mixing with other materials such as the solvents mentioned above.