• Journal of Applied Biological Chemistry
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• v.66
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• pp.213-220
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• 2023

The most common skin disease, acne, often occurs in adolescence, but it is also detected/observed in adults due to air pollution and drug abuse. One of the causative agents of acne, Cutibacterium acnes (C. acnes) plays a role in the development of skin acne by inducing inflammatory mediators. Torreya nucifera (TN) is an evergreen tree of the family Taxaceae, having well reported antioxidant, anti-proliferative, liver protection, and nerve protection properties. Improvement of these bioactive properties of natural products is one of the purposes of natural product chemistry and pharmaceuticals. We believe biorenovation could be one improvement strategy that utilizes microbial metabolism to produce unique derivatives having enhanced bioactivity. Therefore, in this study, the C. acnes-induced RAW264.7 inflammation model was used to evaluate the anti-inflammatory activity of the biorenovated Torreya nucifera product (TNB). The results showed improved viability of TNB-treated cells compared to TN-treated cells in the concentration range of 50, 100, and 200 ㎍/mL. At non-toxic concentrations, TNB inhibited the production of nitric oxide and prostaglandin E2 by suppression of inducible nitric oxide synthase and cyclooxygenase-2 protein expression. TNB also attenuated the expression of interleukin-1β, interleukin-6, interleukin-8, and tumor necrosis factor-α induced by C. acnes. Furthermore, TNB inhibited the nuclear factor-κB signaling pathway, a transcription factor known to regulate inflammatory mediators. Based on these results, this study suggests the potential of using TNB as natural material for the treatment of acnes and thus, supporting our postulation of biorenovation as an bioactivity improvement strategy.

• Journal of Applied Biological Chemistry
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• v.66
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• pp.46-52
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• 2023

The most abundant flavanone of grapefruits, naringenin (NN), is well known for its hepatoprotective, anti-lipid peroxidation and anti-carcinogenic effects. We generated three derivatives from NN using this technique in previous studies. Among them, it was confirmed that naringenin-7-O-phosphate (N7P), whose biological and physicochemical properties were not reported, showed a water solubility 45 times higher than that of NN. Therefore, in this study, the anti-inflammatory activity was evaluated in RAW 264.7 cells to investigate the potential physiological activity of N7P. As a result, N7P showed nitric oxide (NO) inhibitory activity at concentrations that did not show toxicity. In addition, prostaglandin E₂ (PGE₂) showed significant inhibitory activity from the lowest concentration of 12.5 μM and showed increased inhibitory activity compared to NN. In addition, as a result of western blot, N7P showed increased cyclooxygenase-2 (COX-2) inhibitory activity than NN, and effectively inhibited NO and PGE₂ by significantly inhibiting their expression pathways. N7P also inhibited inflammatory cytokines, including tumor necrosis factor-α, interleukin-6. Based on these results, we propose that N7P can be used as a potent antiinflammatory agent.

• The Korean Journal of Pesticide Science
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• v.16 no.1
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• pp.1-10
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• 2012

Fungicidal activities against phytopathogenic fungi of diarylthiazole compound of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-fluorophenyl)thiazol-5-yl]-1-methylpiperidine (I) have been determined to be excellent and compound I was used as the leading compounds in this study. Furthermore, the compound was synthesized by reacting them with five functional groups, 4-fluoro-3-methylphenyl, 4-fluoro-3-chlorophenyl, 4-chloro-2-fluorophenyl, 4-bromo-3-methylphenyl and 2,4-dichlorophenyl groups instead of 4-fluorophenyl group. Also, 2-amino-, 2-(N-ethoxycarbonyl)piperidin-4-yl-, and 2-piperidin-4-yl-thiazole were introduced as the leads instead of 2-N-methylpiperidine-4-yl-thiazol of compound I. VIII-1~VIII-5 and XIII-1~XV-5 compounds were newly synthesized and their structures were confirmed by $^1H$-NMR-spectrum. The fungicidal activities of all the synthesized compounds against Phytophthora capsici were examined using the whole plant method. Among the VIII-1~VIII-5 and XIII-1~XV-5 chemicals, XIV-3 showed the most potent antifungal activity in vivo. While the $EC_{50}$ and $EC_{90}$ values of the commercial fungicide dimethomorph and I were $4.26{\pm}0.02$, $14.72{\pm}0.05$ and $1.01{\pm}0.11$, $6.31{\pm}0.09mM$, those of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-chloro-2-fluorophenyl)thiazol-5-yl]-1-methylpiperidine (XIV-3) was $0.98{\pm}0.21$ and $5.85{\pm}0.05mM$. Therefore, XIV-3 can be considered as a viable candidate for the control of plant diseases caused by P. capsici, and further studies will be conducted on the mode of action XIV-3.

• Journal of Mushroom
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• v.9 no.4
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• pp.186-189
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• 2011

The transitivity of Chemical constituents by Pleurotus ostreatus cultivated in different raw sawdusts, which are Juglans mandchurica, Cudrania tricuspidata and Lindera glauca, was investigated. The HPLC chromatography patterns on the chemical constituents of P. ostreatus showed the similar chromatography patterns in all different raw sawdusts and control sawdust. The unknown chemical constituents of P. ostreatus cultivated in the 10%, 20% mixed medium added 10 %, 20% different raw sawdusts, respectively, were increased. But the significance results in the mixed medium added 50% different raw sawdusts were not showed. The chromatography patterns of mycelia grown in media added the 80% MeOH extracts of three tree species showed the similar patterns in comparison with control mycelia. In the results, the secondary metabolites of functional media were not degrade and changed to other derivatives compounds by P. ostreatus.

• Journal of Mushroom
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• v.9 no.4
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• pp.194-197
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• 2011

The transitivity of Chemical constituents by Pleurotus ostreatus cultivated in different raw sawdusts, which are Acer tegmentosum MAX, Rhus verniciflura, was investigated. The HPLC chromatography patterns on the chemical constituents of P. ostreatus showed the similar chromatography patterns in the different raw sawdusts and control sawdust. The unknown chemical constituents of P. ostreatus cultivated in the mixed medium added 10 %, 20% raw sawdusts, respectively, were increased. But the significance results in the mixed medium added 50% raw sawdusts were not showed. The chromatography patterns of mycelia grown in media added the 80% MeOH extracts of A. tegmentosum and R. verniciflura showed the similar patterns in comparison with control mycelia. In the results, the secondary metabolites of functional media were not degrade and changed to other derivatives compounds by P. ostreatus.

• Korean Journal of Environment and Ecology
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• v.28 no.5
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• pp.574-587
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• 2014

In this study, vertical distribution patterns of Quercus mongolica Fisch. ex Ledeb. and Q. serrata Murray in Korea were recognized and possibility of introgressive hybridization and gene flow between Q. mongolica and Q. serrata in Mt. Jiri was inferred by flavonoid analyses. The most critical factor on distribution patterns was the altitude in accordance with temperature condition. A zonal distribution was recognized: Quercus mongolica zone in the upper area and Q. serrata zone in the lower area. In Central Korea, the range of vertical distribution of Q. mongolica was above alt. 100m, almost everywhere, whereas that of Q. serrata was from alt. 0 m to alt. 500(-700) m, and the species is rare above that altitude. But in Southern Korea, Q. serrata is found up to above alt. 1,000 m, whereas frequency of Q. mongolica reduces as elevation in decline and the species is rare below alt. 300 m, even though pure stands being formed on higher mountain slope. Altitudinal distribution of the two species, however, overlaps, where the two species occur together. Thirty-seven individuals of Q. mongolica and Q. serrata in Mt. Jiri and other area were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols kaempferol, quercetin, isorhamnetin, myricetin, and four compounds among the flavonoid compounds were acylated. Kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside and its acylated compounds were major constituents and present in all individuals. Quercus mongolica is distinguished from Q. serrata by the presence of quercetin 3-O-arabinosylglucoside and by high concentration of three acylated compounds, acylated kaempferol 3-O-glucoside, quercetin 3-O-glucoside, quercetin 3-O-galactoside, and by relatively low concentration or lacking of rhamnosyl flavonol compounds. There are intraspecific variations in flavonoid profiles for Q. mongolica and Q. serrata, the flavonoid profiles for individuals of two species in hybrid zone (sympatric zone) tend to be similar to each other, qualitatively and quantitatively. These findings strongly suggest that gene exchange or gene flow occurs through the introgressive hybridization between Q. mongolica and Q. serrata in Mt. Jiri. Therefore, Quercus crispula, occupying morphologically intermediate position between Q. mongolica and Q. serrata, is suspected of being a hybrid taxon of two putative parental species.

• Journal of the Korean Chemical Society
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• v.29 no.5
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• pp.522-532
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• 1985

The reactions of p-nitrophenyldiphenylphosphate (p-NPDPP) with anions of benzimidazole (BI) and its 2-alkyl derivatives (R-BI) are strongly catalyzed by the micelles of cetyltrimethyl ammonium bromide (CTABr). On the other hand, the first order rate constants $(k'_{R-BI^-})$ and the second order rate constants $(k_{m(R-BI^-)})$ of the reactions mediated by R-$BI^-$in the micellar pseudophase are much smaller than those mediated by $BI^-$. In order to explain the slower rates of the micellar reactions mediated by R-$BI^-$, we compared the concentration-ratios ([R-$BI^-$]/[$BI^-$]) with the first order rate constant-ratios $(k'_{R-BI^-}/k'_{BI^-})$ and the second order constant-ratios $(k_{m(R-BI^-)}/k_{m(BI^-)})$ for the reactions taking place in the micellar pseudophase. The rate constant-ratios were much smaller than the concentration-ratios. For example in a 5 ${\times}10^{-4}$M butyl-BI solution, the two ratios were 0.089 and 0.430 (for the first order) respectively, and in a $10^{-4}$M butyl-BI solution the former was 0.100 (for the second order). This predicts that the reactivities of R-$BI^-$ in the micellar pseudophase are much smaller than that of $BI^-$. Based on the values of several kinetic parameters measured for dephosphorylation of p-NPDPP mediated by R-$BI^-$, a schemetic model is proposed. Due to the hydrophobicity and the steric effect of the alkyl substituents, these groups would penetrate into the core of the micelle for stabilization by van der Waals interaction with long cetyl groups of CTABr. Consequently, the movements of R-$BI^-$ bound to the micelle should be restricted, leading to decreased collison frequencies between the nucleophiles and p-NPDPP. We refer this as an "anchor effect". This effect became more predominent when a larger alky group in R-BI was employed and when a greater concentration of R-BI was used.

• Korean Chemical Engineering Research
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• v.49 no.3
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• pp.330-337
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• 2011

In this research, the preparation processes for making a series of $\omega$-mercapto alkylamine 1 and $\omega$-mercapto alkanoic acid 2 useful for studying of the self-assembled monolayer(SAM) are described. The preparation methods of the first goal materials, $\omega$-mercapto alkylamines 1 were carried out as follows: First, $\omega$-phthalimide alkanol 3 was synthesized from commercially available potassium phthalimide derivatives and $\omega$-bromoalkanol in DMF at $80{^{\circ}C}$ via substitution reaction. After refluxing $\omega$-phthalimide alkanol 3 with hydrazine hydrate in ethanol followed by treating with c-HCl, $\omega$-aminoalkanol 4 was obtained in 76-98% yield, accompanied with side-product 5. Bromination of hydroxyl moiety of $\omega$-aminoalkanol 4 using aqueous hydrobromic acid furnished $\omega$-bromoamine 6 in 34-97% yields. Substitution reaction 6 with thiourea in 95% ethanol gave $\omega$-aminoalkanthiuronium 7, which was treated with aqueous strong base and aqueous strong sulfuric acid gave desired products, $\omega$-mercapto alkylamines 1 through overall 5 steps. The second target material, $\omega$-mercapto alkanoic acid 2 was prepared via 2 steps. $\omega$-bromo alkanoic acid was reacted with thiourea to give $\omega$-thiourea alkanoic acid 7 in 69-85%, which was treated with aqueous strong base and strong acid to furnish $\omega$-mercapto alkanoic acid 2 in 50-98%. The fabricated long-chain alkylthiol(LCAT) can be used as linkers to immobilize protein, enzyme and various kinds of biomolecules on the surface of metallic materials(Au, Pt, Ti) by SAM, and can be useful chemical tools for the application study on the surface modification of metallic materials.

• Korean Journal of Food Science and Technology
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• v.47 no.1
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• pp.27-36
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• 2015

The improved analytical method with gas chromatography (GC) and GC-mass spectrometry was established to identify and quantify disaccharides and trisacchrides in honey. In this method, the analysis of trimethylsilyl (TMS), TMS-oxime and TMS-methoxime sugars takes into account the determination of a single peak of complete separation on the chromatogram. The number of possible peaks for the qualitative and quantitative determination of TMS, TMS-oxime, and TMS-methoxime sugars was 17, 22, and 25, respectively. This new analytical method allowed for the determination of diand trisaccharides in honey by TMS-oxime and TMS-methoxime derivatives. This study suggested that the improved method is more suitable and precise than the other analytical methods for the simultaneous determination of sugars in honey.

• Journal of Food Hygiene and Safety
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• v.33 no.4
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• pp.266-271
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• 2018

The Ministry of Food and Drug Safety (MFDS) is amending its test methods for health-functional foods (dietary food supplements) to establish regulatory standards and specifications in Korea. In this regard, we continue our research on developing analytical methods for the items. Octacosanol is the major component of polycosanol and is a high-molecular-mass primary fatty alcohol, obtained from sugar cane wax. Previous researchers have shown that octacosanol can lower cholesterol and has antiaggregatory properties, cytoprotective uses, and ergogenic properties for human health. Recently, octacosanol products have been actively introduced into the domestic market because of their functional biological activity. We have developed a sensitive and selective test method for octacosanol that the TMS derivatives by means of gas-chromatographic-tandem mass spectrometry (GC-MS). The trimethylsilyl ether derivative of the target analyte showed excellent chromatographic properties. The procedure was validated in the range of $12.5{\sim}200{\mu}g/L$. Standard calibration curves presented linearity with the correlation coefficient ($r^2$) > 0.999, and the limits of detection (LOD) and limits of quantitation (LOQ) were $4.5{\mu}g/L$ and $13.8{\mu}g/L$, respectively. The high recoveries (92.5 to 108.8%) and precision (1.8 to 2.4%) obtained are in accordance with the established validation criteria. Our research can provide scientific evidence to amend the octacosanol test method for the Health-Functional Food Code.