• Title/Summary/Keyword: carbonyl group

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Anti-complement Activity of Triterpenoids from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo;Na, Min-Kyun;Min, Byung-Sun;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.4
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    • pp.249-253
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    • 2008
  • Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

Synthesis of Blue Emitting Materials for Organic Light Emitting Device (유기발광디바이스용 청색발광재료의 합성)

  • Chung, Pyung Jin;Cho, Min Ju
    • Applied Chemistry for Engineering
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    • v.16 no.6
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    • pp.755-759
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    • 2005
  • This study was based on organic electroluminescence display. Especially, DPAVBi, AVBi and DPVBi for the emitting materials were synthesized by Wittig, Wittig-Horner reaction. This reaction was conducted between phosphorous ylide and 4-(diphenylamino)benzaldehyde, 9-anthraldehyde and benzophenone. The structural property of reaction products were analyzed by FT-IR, $^1H-NMR$ spectroscopy and thermal stability, reactivity and PL property were analyzed by melting point, yield and emission spectrum, respectvely. The photoluminescence spectra of a pure DPAVBi, AVBi and DPVBi were observed at approximately 445nm, 484nm and 450nm, respectively. In this study, it was known that DPAVBi, AVBi, DPVBi had a different reaction properties according to stability of ${\alpha}$-position carbonyl group of the aldehyde, ketone.

A Series of Quinoline-2-carboxylic Acid Derivatives: New Potent Glycine Site NMDA Receptor Antagonists

  • 김란희;최진일;최승원;이광숙;정영식;박우규;성철민;박노상
    • Bulletin of the Korean Chemical Society
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    • v.18 no.9
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    • pp.939-945
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    • 1997
  • Several types of 4-substituted-quinoline-2-carboxylic acid derivatives possessing different substituents at C4-position such as sulfonyl, phosphonyl, carbonyl groups, or a flexible alkyl chain have been synthesized and evaluated for their in vitro antagonistic activity at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Of them, 5,7-dichloro-4-(tolylsulfonylamino)-quinoline-2-carboxylic acid 9 was found to have the best in vitro binding affinity with IC50 of 0.57 μM. On the other hand, in compounds 21 and 22 the introduction of flexible alkyl chains on C4 of the quinoline mother nuclei caused a significant decrease of the in vitro binding affinity. In addition, replacement of polar carboxylic acid group on C2 by neutral bioisosteres in compounds 23a-d also seems to be disadvantageous to in vitro activity. In the structure-activity relationship (SAR) study of the 4-substituted quinoline-2-carboxylic acid acid derivatives, it was realized that the substitution pattern on C4 significantly influences on the binding affinity for the glycine site of NMDA receptor and the binding affinity might be increased by the introduction of a suitable electron rich substituent at C4 which has the ability of H-bonding donor.

Cationic Iridium(I) Complex of Ethyl Cinnamate and Hydrogenation of Unsaturated Esters with Iridium(I)-Perchlorato Complex

  • Yang, Kyung-Joon;Chin, Chong-Shik
    • Bulletin of the Korean Chemical Society
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    • v.7 no.6
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    • pp.466-468
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    • 1986
  • Reaction of $Ir(ClO_4)(CO)(PPh_3)_2$ with trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ produces a new cationic iridium(I) complex, [Ir (trans-$C_6H_5CH$ = $CHCO_2C_2H_5)(CO)(PPh_3)_2]ClO_4$ where trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ seems to be coordinated through the carbonyl oxygen rather than through the $\pi$-system of the olefinic group according to the spectral data. It has been found that Ir$(ClO_4)(CO)(PPh_3)_2$ catalyzes the hydrogenation of $CH_2$ = $CHCO_2C_2H_5$, trans-$CH_3CH$ = $CHCO_2C_2H_5$ and trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ to $CH_3CH_2CO_2C_2H_5$, $CH_3CH_2CH_2CO_2C_2H_5$ and $C_6H_5CH_2CH_2CO_2C_2H_5$, respectively at room temperature under the atmospheric pressure of hydrogen. The relative rates of the hydrogenation of the unsaturated esters are mostly understood in terms of steric reasons.

Effect of Several Exterior Adhesive Types on Dimensional Stability of Bamboo Oriented Particleboard

  • Iswanto, Apri Heri;Munthe, Rensus;Darwis, Atmawi;Azhar, Irawati;Susilowati, Arida;Prabuningrum, Dita Sari;Fatriasari, Widya
    • Korean Journal of Materials Research
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    • v.29 no.5
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    • pp.277-281
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    • 2019
  • The objective of this research is to evaluate the effect of adhesive types on dimensional stability of bamboo-oriented particleboard. The materials used in this research are bamboo tali(Gigantochloa apus J.A & J.H. Schult. Kurz), UF/MDI(8, 10, 12 % level), and MF, MDI, and PF at 7 % level. Particle and adhesive are mixed using a blending machine; then, mat forming and hot pressing processes are performed using adhesive-suitable temperature and time references. MDI resin is set at $160^{\circ}C$ temperature for 5 minutes. PF resin and MF resin are pressed at $170^{\circ}C$ for 10 minutes, and $140^{\circ}C$ for 10 minutes, respectively, while UF/MDI sets at temperature of $140^{\circ}C$ for 10 minutes. The results show that particleboard using PF resin produces the lowest thickness swelling value. The particleboard using UF/MDI resin also produces good response for thickness swelling value. Interesting things happen in that UF/MDI adhesive produces a thickness swelling value better than that of MDI resin. FTIR analysis on particleboard bonded by UF/MDI resin combination shows the presence of carbonyl group C=O vibration on multi substitution of urea at wave number of around $1,700cm^{-1}$.

Cyanide detection based on natural dyes reaction from blue butterfly pea flowers (Clitoria Ternatea)

  • Chotichayapong, Chatrachatchaya;Kuchaiyaphum, Pusita;Butwong, Nutthaya;Bua-ngern, Worapong
    • Analytical Science and Technology
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    • v.35 no.4
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    • pp.153-160
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    • 2022
  • A green spectrophotometric method for the determination of cyanide has been proposed using, a green reagent, aqueous extract of blue butterfly pea. The test tube was filled with anthocyanin rich extract (pH 6) and cyanide solution. The reaction was kept constant for 10 minutes at room temperature. The reaction mixture changed color from blue to green as the amount of CN-ions increased. The 620 nm peak intensity increased with CN concentration. Therefore, this wavelength was used for all cyanide analyses. The cyanide calibration curve had a linear range of 0.25-1.00, 1.00-4.00, and 4.00-10.00 mg/L, with a satisfactory correlation coefficient of 0.99 and a LOD of 0.57 mg/L. The recovery ranged from 8.33 to 76.94 percent, indicating that this method is inaccurate at low cyanide concentrations. The intra-day and intermediate precision relative deviations were 0.391-0.871 % and 1.112-1.583 %. An H-bond forms between the C-4 group of the B-carbonyl ring and the HCN molecule according to the B3LYP/TZVP calculation. The method is convenient for cyanide concentrations above the LOQ of 1.09 mg/L, cost-effective, and capable of reducing toxic solvents with acceptable precision. The method could also be used to detect total cyanide in biological, environmental, and industrial waste samples.

Simple and Efficient Method for the Enantiomeric discrimination of Racemates (라세미 화합물의 거울상 이성질체 구분을 위한 간단하고 효과적인 방법)

  • Ho Sik Rho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.49 no.2
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    • pp.141-146
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    • 2023
  • The efficient use of a chiral shift agent (3) containing bifunctional group (thiourea and tertiary amine) for the determination of the enantiomeric purity of racemic mixture (Hemiesters) has been studied. The diastereomeric complexes derived from a chiral shift agent (3) with various hemiesters gave rise to well separate signals of the methoxy protons of hemiesters. Good splitting signals for enantiomers of hemiesters in 1H NMR are originated form the hydrogen bonds between carbonyl groups of hemiester and bifunctional groups of a chiral shift agent (3) such as thiourea moiety and tertiary amine. This study provides a quick and simple way to determine the chiral purity of hemiester using chiral transfer agent (3).

Protective Effect of Soybean Sauce and Melanoidin on Lipid Oxidation in Rats Fed High PUFA Oils (고도불포화지방산 함량이 높은 유지를 섭취시킨 흰쥐에서 양조간장과 멜라노이딘의 지질산화 억제효과)

  • 이상조;류승희;이영순;송영선;문갑순
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.32 no.6
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    • pp.913-920
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    • 2003
  • Soybean sauce fermented with soybean and wheat, has been a major condiment of Korean diets from centuries ago. Melanoidin, a brown pigment generally found in various food systems, is a final product produced in amino-carbonyl reaction during soybean sauce processing. Antioxidative activities of soybean sauce and melanoidin were investigated in vitro system using linoleic acid emulsion. Soybean sauce and glucose-lysine model melanoidin showed the stronger antioxidative effect than control by ferric thiocyanate and conjugated diene assays. In addition, DPPH radical scavenging effect of soybean sauce was higher than melanoidin, which was ascribed to soluble peptide and low molecular protein existing in soybean sauce. To ascertain antioxidative effect of dietary soybean sauce and melanoidin in vivo, the male Wister rats were fed 10% soybean sauce or 10% glucose-lysine model melanoidin with corn oil or fish oil for 5 weeks. Fatty acid compositions in liver and plasma were influenced by oil source. Therefore, EPA and DHA contents of fish oil group were higher than those of corn oil group. When the inhibitory effect of soybean sauce and melanoidin on lipid peroxidation using TBARS methods was measured, fish oil group (FC) showed higher malondialdehyde (MDA) content than corn oil group (CC). However, supplementation of soybean sauce and melanoidin to fish oil group attenuated MDA formation. In the levels of phosphatidyl choline hydroperoxide (PCOOH) in liver and plasma by CL (chemiluminescence)-HPLC method, PCOOH in FC group was significantly higher than that of CC group both in liver and plasma. Supplementation of soybean sauce to fish oil groups significantly inhibited the formation of PCOOH in plasma and liver, while melanoidin suppressed hepatic PCOOH formation. Based on these results, it can be suggested that soybean sauce possesses stronger antioxidative potential than melanoidin.

Reaction of Phosphorus Ylides with Carbonyl Compounds in Supercritical Carbon Dioxide (초임계 이산화탄소에서의 유기인 일리드와 카르보닐 화합물의 반응)

  • Jeong, Kyung-Il;Kim, Hak-Do;Shim, Jae-Jin;Ra, Choon-Sup
    • Journal of the Korean Chemical Society
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    • v.48 no.1
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    • pp.28-32
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    • 2004
  • The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 $^{\circ}C$, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellant yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under $scCO_2$ condition than in THF. The reaction of (benzylene)triphenylphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possibile tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.

Quality Characteristics of Citron Treated Mackerel Oil and Fillet during Refrigerated Storage (유자액 처리에 의한 고등어유와 필렛의 냉장 저장중 품질 특성)

  • Jung, Bok-Mi;Chung, Gyu-Hwa;Jang, Mi-Soon;Shin, Suk-U
    • Korean Journal of Food Science and Technology
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    • v.36 no.4
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    • pp.574-579
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    • 2004
  • Quality characteristics of citron-treated mackerel oil and fillet during refrigerated storage were evaluated. Citron-treated and non-treated mackerel oil and fillet were estimated by periodical measurements of acid, peroxide, carbonyl, volatile basic nitrogen, trimethylamine-N, and thiobarbituric acid values. Volatile basic nitrogen and trimethylarnine-N values in mackerel fillet treated with citron for 25 days during refrigerated storage were significantly lower than those of citron non-treated mackerel fillet, with those of boiled citron water-treat group significantly decreasing compared to 1 and 2% citron extract groups. Acid, peroxide, carbonyl, and thiobarbituric acid values of citron-treated mackerel oil were significantly lower than those of citron non-treated mackerel oil throughout storage period. Overall acceptability of salted mackerel fillets treated with boiled citron water and 1% citron extract was significantly than those of control and 2% citron extract. Results indicate application of citron juice on mackerel surface may be useful to lower rancidity degree and fish odor during refrigerated storage.