• Title/Summary/Keyword: Amide compounds

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Characterization of intrinsic molecular structure spectral profiles of feedstocks and co-products from canola bio-oil processing: impacted by source origin

  • Alessandra M.R.C.B., de Oliveira;Peiqiang, Yu
    • Animal Bioscience
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    • v.36 no.2
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    • pp.256-263
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    • 2023
  • Objective: Feed molecular structures can affect its availability to gastrointestinal enzymes which impact its digestibility and absorption. The molecular spectroscopy-attenuated total reflectance Fourier transform infrared vibrational spectroscopy (ATR-FTIR) is an advanced technique that measures the absorbance of chemical functional groups on the infrared region so that we can identify and quantify molecules and functional groups in a feed. The program aimed to reveal the association of intrinsic molecular structure with nutrient supply to animals from canola feedstocks and co-products from bio-oil processing. The objective of this study was to characterize special intrinsic carbohydrate and protein-related molecular structure spectral profiles of feedstock and co-products (meal and pellets) from bio-oil processing from two source origins: Canada (CA) and China (CH). Methods: The samples of feedstock and co-products were obtained from five different companies in each country arranged by the Canola Council of Canada (CCC). The molecular structure spectral features were analyzed using advanced vibrational molecular spectroscopy-ATR-FTIR. The spectral features that accessed included: i) protein-related spectral features (Amide I, Amide II, α-helix, β-sheet, and their spectral intensity ratios), ii) carbohydrate-related spectral features (TC1, TC2, TC3, TC4, CEC, STC1, STC2, STC3, STC4, TC, and their spectral intensity ratios). Results: The results showed that significant differences were observed on all vibrationally spectral features related to total carbohydrates, structural carbohydrates, and cellulosic compounds (p<0.05), except spectral features of TC2 and STC1 (p>0.05) of co-products, where CH meals presented higher peaks of these structures than CA. Similarly, it was for the carbohydrate-related molecular structure of canola seeds where the difference between CA and CH occurred except for STC3 height, CEC and STC areas (p>0.05). The protein-related molecular structures were similar for the canola seeds from both countries. However, CH meals presented higher peaks of amide I, α-helix, and β-sheet heights, α-helix:β-sheet ratio, total amide and amide I areas (p<0.05). Conclusion: The principal component analysis was able to explain over 90% of the variabilities in the carbohydrate and protein structures although it was not able to separate the samples from the two countries, indicating feedstock and coproducts interrelationship between CH and CA.

Synthesis of Lipophilic Benz[cd]indole Antifolates and Their Antitumor Activity In Vitro (지용성 Benz[cd]indole 엽산길항제의 합성 및 In Vitro 항암활성)

  • Baek Du-Jong
    • YAKHAK HOEJI
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    • v.49 no.1
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    • pp.60-67
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    • 2005
  • Nonclassical aminobenz[cd]indole antifolates 4, 5 and 6, in which the glutamic acid moiety of the classical antifolates is substituted by 2-phenylglycinamide or 3-aminobenzamide, were synthesized and their in vitro antitumor activity was evaluated. The purpose of this substitution is that the lipophilicity is enhanced due to the aromatic ring of the target compounds for the passive transport through lipid membrane of cells while the hydrogen bonding of the amide is retained in the active site of the enzyme, thymidylate synthase, where the glutamate is originally present. The target compounds were highly cytotoxic against tumor cell lines of murine and human origin with micromolar to nanomolar $IC_{50}$ values. Most effective was compound 4 ($N^6-methyl-N^6$-[4-[(${\alpha}$(S)-aminocarbonylbenzyl) aminocarbonyl]benzyl]-2,6-diaminobenz[cd]indole)with $IC_{50}$ of 2 nM against SW480, human colon adenocarcinoma cell line, which is 650-fold more potent than the reference compound 3.

Maillard Reaction Products Formed from D-Glucose-Glycine, System and Their Formation Mechanism (D-Glucose-Glycine 계의 Maillard 반응생성물 및 그 생성기구)

  • KIM Seon-Bong;PARK Yeung-Ho
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.19 no.1
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    • pp.45-51
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    • 1986
  • Equimolar aqueous solutions of D-glucose and glycine were heated at $50^{\circ}C\;and\;95^{\circ}C$ at pH 6.7. The headspace volatiles and the ether extracts from the reaction mixture were analyzed by gas chromatography and gas chromatography-mass spectrometry using a fused silica capillary column. The major components formed were identified as diacetyl, three furfurals, two pyrroles, one furanone, two pyranones and two amides. In order to elucidate the formation mechanisms of the amides formed front amino-carbonyl reaction, two model systems were adopted. N-butylacetamide were formed as major components from diacetyl-butylamine ana glyoxal-butylamine systems, respectively. The results obtained suggest that such ${\alpha}-dicarbonyls$ as 3-deoxy-D-erythro-2,3-hexodiulose and diacetyl generated in the amino-carbonyl reaction react with amino compounds, amides then being formed by cleavage of the C-C bond in the ${\alpha}-dicarbonyls$.

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Synthesis of (5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8α-octahydroazulen-5-yl) Acrylic Acid (Rupestonic Acid) Amide Derivatives and in vitro Inhibitive Activities against Influenza A3,B and Herpes Simplex Type 1 and 2 Virus

  • Yong, Jian-Ping;Lv, Qiao-Ying;Aisa, Haji Akber
    • Bulletin of the Korean Chemical Society
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    • v.30 no.2
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    • pp.435-440
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    • 2009
  • 19 Aromatic ring and L-amino acid ester contained rupestonic acid amide derivatives 2a~2l, 3a~3g were synthesized and preliminarily evaluated in vitro against influenza virus $A_3$,B and herpes simplex virus type 1 (HSV-1), 2(HSV-2) by the national center for drug screening of China. The rusults showed that 2i possessed the highest inhibition against both influenza virus $A_3\;(TC_{50}\;=\;120.6\;{\mu}mol/L,\;IC_{50}=\;19.2\;{\mu}$mol/L, SI = 6.3) and B (T$C_{50}\;=\;120.6\;{\mu}mol/L,\;IC_{50}=\;29.9\;{\mu}$mol/L, SI = 4.0); 2g was more active against influenza $A_3$ virus at very low cytotoxicity ($TC_{50}\;>\;2092.1\;{\mu}mol/L,\;IC_{50}=\;143.7\;{\mu}mol/L,$ SI > 14.6) than the parent compound; Compounds 2b, 2c, 2f showed higher activities both against HSV-1 and HSV-2 than that of the parent compound, and 2f was the most potent inhibitor of HSV-1 ($TC_{50}\;=\;200.0\;{\mu}mol/L,\;IC_{50}\;=\;11.3\;{\mu}mol$/L, SI = 17.7 ) and HSV-2 ($TC_{50}\;=\;200.0\;{\mu}mol/L,\;IC_{50}\;=\;20.7\;{\mu}mol$/L , SI = 9.7).

Asparagine Biosynthesis in Soybean Sprouts (콩나물의 Asparagine 생합성(生合成)에 관(關)한 연구(硏究))

  • Byun, Si-Myung;Huh, Nam-Eung;Lee, Chun-Yung
    • Applied Biological Chemistry
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    • v.20 no.1
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    • pp.33-42
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    • 1977
  • Asparagine biosynthesis by soybean sprouts grown under the dark conditions has been demonstrated. The amount of free asparagine synthesized in ten day-old soybean sprouts increases to 22.7% on the dry weight base. The effects of nitrogen compounds such as $NH_4Cl,\;(NH_4)_2SO_4$ and urea on asparagine synthesis during the sprouting were examined and the results showed that urea was more effective than other two compounds. Glutamine-dependent asparagine synthetase was partially purified (8.6 folds) through ammonium sulfate fractionation, followed by Sephadex G-150 gel filtration. The enzyme was very labile and required protection by thiol groups or high level of glycerol. The mixture of ATP and $Mg^{++}$ ion also stabilized the enzyme activity. The enzyme utilized glutamine more effectively than ${NH_4}^+$ as an amide donor for the formation of asparagine. The enzyme required L-aspartate (Km=3.1 mM), L-glutamine, ATP and $Mg^{++}$. It showed pH optimum of 7.5 and catalyzed the formation of ${\beta}-aspartyl$ hydroxamate in the presence of L-aspartate, ATP, $Mg^{++}$ and $NH_2OH$ in the reaction mixture.

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The Effect of Gamma-Irradiation on Aqueous Solutions of Triglycine 3. Mechanism for Gamma-ray Induced Degradation Products (Triglycine 수용액에 미치는 감마선의 영향 3. 감마선에 의한 분해산물에 관하여)

  • ;LEONE, Charles A
    • The Korean Journal of Zoology
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    • v.7 no.2
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    • pp.1-5
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    • 1964
  • Carbonyl compounds, glycine, ammonia, carbon dioxide and hydrogen have been identified in gamma-irradiated oxygenated aqueous solutions of triglycine. The reactions occurring in this system are postulated only by representing the initial process and the final products. The triglycine molecule undergoes a reaction to form an intermediate giving rise to carbonyl compounds and acid amides. These compounds are decomposed to acetamide, glycine, glyoxylic acid, formic acid, oxalic acid, ammonia, and carbon dioxide by free radical attack in the primary and/or secondary reactions. It is also possible that the unrecognized reactions may give rise to products formed by radical-radical combinations. Satisfactory material balance for all the products have to wait until the completion of a study now in progress.ogress.

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Nitrogen fractionation of organic materials applied to Korean ginseng (고려인삼(高麗人蔘) 유기질비료의 질소성장(窒素性狀)에 대하여)

  • Hong, Jung-Kook;Park, Hoon;Lee, Chong-Hwa
    • Korean Journal of Soil Science and Fertilizer
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    • v.12 no.2
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    • pp.91-97
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    • 1979
  • 1. Nitrogenous compounds of-organic materials as nitrogen sources for Korean ginseng were characterized according to their solubility and chemical forms. 2. The extractable fractionation was as follows : Yakto group : non-extractable N > acid hydrolyzable N > acid nonhydrolyzable N > water sol. N, Litter group : acid hydrolyzable N > non-extractable N > water sol. N > acid non-hydrolyzable N, Bone meal : acid hydrolyzable N > water sol. N > acid non-hydrolyzable N. 3. Nitrogenous compounds in the water sol. fraction were : Yakto group and Litter group : humus N > amino acid N > nitrate N (recognized only in Yakto group) > ammonia N > hexosamine N > amide N, Bone meal : amino acid N > humus N > ammonia N > amide N. And nitrogenous compounds in the acid hydrolyzable fraction were : amino acid N > humus N ${\simeq}$ ammonia N > hexosamine N. 4. Availability was discussed about the major nitrogenous compounds (amino acid, humus and inorganic N) and the solubility.

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Holographic Quantitative Structure-Toxicity Relationships on the Skin Sensitization of Alkyl-3,4- dihydroxybenzoate and N-Alkyl -3,4- dihydroxybenzamide Derivatives (Alkyl-3,4-dihydroxybenzoate와 N-Alkyl-3,4-dihydroxybenzamide 유도체의 피부 감작성에 관한 홀로그래피적인 정량적 구조와 독성과의 관계(HQSTR))

  • Kim Sang-Jin;Sung Nack-Do;Jung Hoon-Sung
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.31 no.1 s.49
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    • pp.91-96
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    • 2005
  • Holographic quantitative structure-toxicity relationships (HQSTR) of alkyl-3,4-dihydroxybenzoate (A) and N-alkyl-3,4-dihydroxybenzamide (B) derivatives were analyzed and discussed. The HQSTR model X for the skin sensitivity showed the best predictability based on the cross-validated $r^2_{cv}.$ ($q^2 = 0.744$), non cross-validated, and conventional coefficient ($r^2_{ncv}.$=0.978). The relationships between melanogenesis inhibitory activities and skin sensitization of compounds have a tendency to a reciprocal proportion. Therefore, the more higher melanogenesis inhibitory activities of compounds were, the more lower skin sensitization of compounds became. The side chain, C1 ${\~}$ C3 part of R1-substituents in (A) and (B) did not exhibit any contribution to skin sensitization. Particularly, it is reveals that the skin sensitization of ester (A) were slightly lower (A < B) than that of amide (B) and melanogenesis Inhibitory activities of (A) were slightly higher (A > B) than that of (B). It is founded that the alkyl-3,4-dihydroxybenzoate derivatives (A) were an ideal compound as an ingredient of whitening agents.

Evaluation of the antimalarial activity of SAM13-2HCl with morpholine amide (SKM13 derivative) against antimalarial drug-resistant Plasmodium falciparum and Plasmodium berghei infected ICR mice

  • Hyelee Hong;Kwonmo Moon;Thuy-Tien Thi Trinh;Tae-Hui Eom;Hyun Park;Hak Sung Kim;Seon-Ju Yeo
    • Parasites, Hosts and Diseases
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    • v.62 no.1
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    • pp.42-52
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    • 2024
  • Antimalarial drugs are an urgently need and crucial tool in the campaign against malaria, which can threaten public health. In this study, we examined the cytotoxicity of the 9 antimalarial compounds chemically synthesized using SKM13-2HCl. Except for SKM13-2HCl, the 5 newly synthesized compounds had a 50% cytotoxic concentration (CC50) >100 μM, indicating that they would be less cytotoxic than SKM13-2HCl. Among the 5 compounds, only SAM13-2HCl outperformed SKM13-2HCl for antimalarial activity, showing a 3- and 1.3-fold greater selective index (SI) (CC50/IC50) than SKM13-2HCl in vitro against both chloroquine-sensitive (3D7) and chloroquine -resistant (K1) Plasmodium falciparum strains, respectively. Thus, the presence of morpholine amide may help to effectively suppress human-infectious P. falciparum parasites. However, the antimalarial activity of SAM13-2HCl was inferior to that of the SKM13-2HCl template compound in the P. berghei NK65-infected mouse model, possibly because SAM13-2HCl had a lower polarity and less efficient pharmacokinetics than SKM13-2HCl. SAM13-2HCl was more toxic in the rodent model. Consequently, SAM13-2HCl containing morpholine was selected from screening a combination of pharmacologically significant structures as being the most effective in vitro against human-infectious P. falciparum but was less efficient in vivo in a P. berghei-infected animal model when compared with SKM13-2HCl. Therefore, SAM13-2HCl containing morpholine could be considered a promising compound to treat chloroquine-resistant P. falciparum infections, although further optimization is crucial to maintain antimalarial activity while reducing toxicity in animals.