• Title/Summary/Keyword: Sulfonic acids

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Antioxidant and angiotensin I-converting enzyme inhibitory activities of northern shrimp (Pandalus borealis) by-products hydrolysate by enzymatic hydrolysis

  • Kim, Sang-Bo;Yoon, Na Young;Shim, Kil-Bo;Lim, Chi-Won
    • Fisheries and Aquatic Sciences
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    • v.19 no.7
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    • pp.29.1-29.6
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    • 2016
  • In the present study, we investigated to the antioxidant and angiotensin I-converting enzyme (ACE) inhibitory activities of the northern shrimp (Pandalus borealis) by-products (PBB) hydrolysates prepared by enzymatic hydrolysis. The antioxidant and ACE inhibitory activities of five enzymatic hydrolysates (alcalase, protamex, flavourzyme, papain, and trypsin) of PBB were evaluated by the 2, 2'-azino-bis [3-ethylbenzothiazoline-6-sulfonic acid] ($ABTS^+$) radical scavenging and superoxide dismutase (SOD)-like activities, reducing power and Li's method for ACE inhibitory activity. Of these PBB hydrolysates, the protamex hydrolysate exhibited the most potent ACE inhibitory activity with $IC_{50}$ value of $0.08{\pm}0.00mg/mL$. The PBB protamex hydrolysate was fractionated by two ultrafiltration membranes with 3 and 10 kDa (below 3 kDa, between 3 and 10 kDa, and above 10 kDa). These three fractions were evaluated for the total amino acids composition, antioxidant, and ACE inhibitory activities. Among these fractions, the < 3 kDa and 3-10 kDa fractions showed more potent $ABTS^+$ radical scavenging activity than that of > 10 kDa fraction, while the > 10 kDa fraction exhibited the significant reducing power than others. In addition, 3-10 kDa and > 10 kDa fractions showed the significant ACE inhibitory activity. These results suggested that the high molecular weight enzymatic hydrolysate derived from PBB could be used for control oxidative stress and prevent hypertension.

Comparison of the plant uptake factor of perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic acid (PFOS) from the three different concentrations of PFOA and PFOS in soil to spinach and Welsh onion

  • Lee, Deuk-Yeong;Choi, Geun-Hyoung;Rho, Jin-Ho;Lee, Hyo-Sup;Park, Sang-Won;Oh, Kyeong-Yeol;Kim, Jin-Hyo
    • Journal of Applied Biological Chemistry
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    • v.63 no.3
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    • pp.243-248
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    • 2020
  • The long-chained perfluoroalkyl acids (PFAAs), perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS), are a potential exposure risk in the environment, specifically for humans due to high levels of bioaccumulation, persistence, and toxicity. In the current study, the plant uptake factors (PUFs) of spinach and Welsh onion were investigated on the three different concentration levels of PFOA and PFOS in soil. Spinach and Welsh onion were divided into three residue groups, a control group and two levels of PFOA and PFOS. The PFAAs spiked soils were aged for six months and the extractable residue of PFOS in the aged soil was reduced to 30-59% of the initial spiked concentrations for PFOS, while PFOA showed almost the same initial spiked concentrations. The PUFs for PFOA and PFOS were 0.111-2.821 and 0.047-3.175 for spinach, and 0.203-0.738 and 0.035-0.181 for Welsh onion, respectively. The highest PUF values in both vegetable were displayed when the residual concentration of PFAAs were part-per-billion (ppb) or sub-ppb in soil.

Reaction of Diisobutylaluminum Hydride-Dimethyl Sulfide Complex with Selected Organic Compounds Containing Representative Functional Groups. Comparison of the Reducing Characteristics of Diisobutylaluminum Hydride and Its Dimethyl Sulfide Complex

  • Cha, Jin-Soon;Jeong, Min-Kyu;Kwon, Oh-Oun;Lee, Keung-Dong;Lee, Hyung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.873-881
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    • 1994
  • The approximate rate and stoichiometry of the reaction of excess diisobutylaluminum hydride-dimethyl sulfide complex($DIBAH-SMe_2$) with organic compounds containing representative functional group under standardized conditions (toluene, $0{\circ}C$) were examined in order to define the reducing characterstics of the reagent and to compare the reducing power with DIBAH itself. In general, the reducing action of the complex is similar to that of DIBAH. However, the reducing power of the complex is weaker than that of DIBAH. All of the active hydrogen compounds including alcohols, amines, and thiols evolve hydrogen slowly. Aldehydes and ketones are reduced readily and quantitatively to give the corresponding alcohols. However, $DIBAH-SMe_2$ reduces carboxylic acids at a faster rate than DIBAH alone to the corresponding alcohols with a partial evolution of hydrogen. Similarly, acid chlorides, esters, and epoxides are readily reduced to the corresponding alcohols, but the reduction rate is much slower than that of DIBAH alone. Both primary aliphatic and aromatic amides examined evolve 1 equiv of hydrogen rapidly and are reduced slowly to the amines. Tertiary amides readily utilize 2 equiv of hydride for reduction. Nitriles consume 1 equiv of hydride rapidly but further hydride uptake is quite slow. Nitro compounds, azobenzene, and azoxybenzene are reduced moderately. Cyclohexanone oxime liberates ca. 0.8 equiv of hydrogen rapidly and is reduced to the N-hydroxylamine stage. Phenyl isocyanate is rapidly reduced to the imine stage, but further hydride uptake is quite sluggish. Pyridine reacts at a moderate rate with an uptake of one hydride in 48 h, while pyridine N-oxide reacts rapidly with consumption of 2 equiv of hydride for reduction in 6h. Similarly, disulfides and sulfoxide are readily reduced, whereas sulfide, sulfone, and sulfonic acid are inert to this reagent under these reaction conditions.

Reducing Characteristics of Potassium Tri-sec-butylborohydride

  • Yoon, Nung-Min;Hwang, Young-Soo;Yang, Ho-Seok
    • Bulletin of the Korean Chemical Society
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    • v.10 no.4
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    • pp.382-388
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    • 1989
  • The approximate rates and stoichiometry of the reaction of excess potassium tri-sec-butylborohydride ($K_s-Bu_3BH$) with selected organic compounds containing representative functional groups were determined under the standard conditions (0$^{\circ}C$, THF) in order to define the characteristics of the reagent for selective reductions. Primary alcohols evolve hydrogen in 1 h, but secondary and tertiary alcohols and amines are inert to this reagent. On the other hand, phenols and thiols evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of norcamphor gives 99.3% endo- and 0.7% exo-isomer of norboneols. The reagent rapidly reduces cinnamaldehyde to the cinamyl alcohol stage and shows no further uptake of hydride. p-Benzoquinone takes up one hydride rapidly with 0.32 equiv hydrogen evolution and anthraquinone is cleanly reduced to the 9,10-dihydoxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively, however further reduction does not occur. Anhydrides utilize 2 equiv of hydride and acyl chlorides are reduced to the corresponding alcohols rapidly. Lactones are reduced to the diol stage rapidly, whereas esters are reduced moderately (3-6 h). Terminal epoxides are rapidly reduced to the more substituted alcohols, but internal epoxides are reduced slowly. Primary and tertiary amides are inert to this reagent and nitriles are reduced very slowly. 1-Nitropropane evolves hydrogen rapidly without reduction and nitrobenzene is reduced to the azoxybenzene stage, whereas azobenzene and azoxybenzene are inert. Cyclohexanone oxime evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine and quinoline are reduced slowly, however pyridine N-oxide takes up 1.5 equiv of hydride in 1 hr. Disulfides are rapidly reduced to the thiol stage, whereas sulfide, sulfoxide, sulfonic acid and sulfone are practically inert to this reagent. Primary alkyl bromide and iodide are reduced rapidly, but primary alkyl chloride, cyclohexyl bromide and cyclohexyl tosylate are reduced slowly.

Antioxidant and anti-inflammatory activity of parts of Rhus javanica L. (붉나무의 부위 별 항산화 및 항염증 활성)

  • Choi, Ji-Soo;Han, Sang-Don;Jang, Tae-Won;Lee, Seung-Hyun;Park, Jae-Ho
    • Journal of Applied Biological Chemistry
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    • v.62 no.2
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    • pp.195-202
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    • 2019
  • Rhus javanica L. is Anacardiaceae plant distributed in East Asia. We evaluated the antioxidant activity and antiinflammatory effect of leaf, branch, root of ethyl acetate fraction from R. javanica. To confirm effective each extraction, The antioxidant activity was evaluated using 1,1-Diphenyl-2-picryl-hydrazyl and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) scavenging activity assays, and the anti-inflammatory activity was evaluated based on inhibitory activities on the protein and mRNA expression of iNOS and COX-2 in LPS-induced RAW264.7 cells. The phenolic compounds content of each extract was analyzed with Folin reagents and HPLC/PDA method. The gallic acids were identified and quantified. The roots of R. javanica showed strong antioxidant activity. Its total phenolic compounds content were higher than the orders. In addition, anti-inflammatory activity inhibited the protein and mRNA expression of nitric oxide production factor, following the same pattern as contents of phenolic compounds included gallic acid and its antioxidant activity. In conclusion, R. javanica showed effective antioxidant and anti-inflammatory activity. Especially, the roots were evaluated to be highly valuable as a natural resource for reducing inflammation.

Rice bran fermentation by lactic acid bacteria to enhance antioxidant activities and increase the ferulic acid, ρ-coumaric acid, and γ-oryzanol content

  • Le, Bao;Anh, Pham Thi Ngoc;Kim, Jung-Eun;Cheng, Jinhua;Yang, Seung Hwan
    • Journal of Applied Biological Chemistry
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    • v.62 no.3
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    • pp.257-264
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    • 2019
  • Rice bran is considered a natural source of antioxidants. In this study, rice bran was fermented with lactic acid bacteria to increase its antioxidant activity. Four strains isolated from fermented food, Lactobacillus plantarum MJM60383, Lactococcus lactis subsp. lactis MJM60392, Lactobacillus fermentum MJM60393, and Lactobacillus paracasei MJM60396, were confirmed as safe through stability tests such as safety assessment for biogenic amine production, hemolytic activity, and mucin degradation, and showed high reducing capacity. The antioxidant activity of rice bran fermentation altered by these strains was evaluated using several methods including measurement of $Fe^{2+}$ chelating activity and scavenging activity by 1,1-diphenyl-2-picryl-hydrazil (DPPH), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and nitric oxide assays. In this study, the total phenolic content and ${\gamma}$-oryzanol were evaluated by high-performance liquid chromatography. Compared to non-fermented rice bran and a commercial product, rice bran fermented with Lactococcus lactis subsp. lactis MJM60392 showed the highest phenolic content (844.13 mg GAE/g). Moreover, the content of ferulic acids, ${\rho}$-coumaric acid, and ${\gamma}$-oryzanol in rice bran increased after fermentation with L. lactis subsp. lactis MJM60392 and L. fermentum MJM60393 compared to other samples. Indeed, the DPPH radical scavenging activity and NO scavenging activity were also found to be high in these fermented rice brans. These results indicated that fermentation with lactic acid bacteria increases the active compound levels and the potent antioxidant activities of rice bran.

Effect of Defatted Torreya nucifera Seed Extract on the Cross-linking of Advanced Glycation End Products to Collagen (비자 유박 추출물이 최종당화산물과 콜라겐 교차결합에 미치는 효과)

  • Son, Dahee;Kim, Minkyung;Park, Deokhoon;Jung, Eunsun
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.45 no.1
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    • pp.19-25
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    • 2019
  • Advanced glycation end products (AGEs) are final products formed by glycation reaction between reducing sugars and proteins, lipids or nucleic acids. These AGEs are related to progress of skin aging. In this study, we evaluate anti-aging activity of Defatted Torreya nucifera seed extract (DTSE) through antioxidant, anti-glycation, anti-elastase and inhibitory and breaking activity on the cross-linking of AGEs to collagen assay. Results showed that DTSE contained polyphenols and flavonoids. The $IC_{50}$ values of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging activity were $16.4{\mu}g$ (Dried materials, DM)/mL and $16.7{\mu}g\;DM/mL$, respectively. DTSE also inhibited the formation of AGEs, elastase activity and cross-linking of AGEs to collagen as well as broke existing cross-linking of AGEs to collagen in a dose-dependent manner. Consequently, our findings suggest that DTSE could be useful as a cosmetic material with anti-aging activity.

Reducing Characteristics of Potassium Triethylborohydride

  • Yoon, Nung-Min;Yang H.S.;Hwang, Y.S.
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.285-291
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    • 1987
  • The approximate rates, stoichiometries and products of the reaction of potassium triethylborohydride $(KEt_3BH)$ with selected organic compounds containing representative functional groups under the standard condition $(0^{\circ}C,$ THF) were examined in order to explore the reducing characteristics of this reagent as a selective reducing agent. Primary alcohols, phenols and thiols evolve hydrogen rapidly whereas secondary and tertiary alcohols evolve very slowly. n-Hexylamine is inert to this reagent. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of noncamphor gives 3% exo- and 97% endo-norboneol. Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-dihydroxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively but further reduction does not occur. Anhydrides utilize 2 equiv of hydride to give an equimolar mixture of acid and alcohol. Acid chlorides, esters and lactones are rapidly and quantitatively reduced to the corresponding alcohols. Epoxides are reduced at moderate rates with Markovnikov ring opening to give the more substituted alcohols. Primary amides liberate 1 equiv of hydrogen rapidly. Further reduction of caproamide is slow whereas benzamide is not reduced. Tertiary amides are reduced slowly. Benzonitrile utilizes 2 equiv of hydride in 3 h to go to the amine stage whereas capronitrile takes only 1 equiv. The reaction of nitro compounds undergo rapidly whereas azobenzene and azoxybenzene are reduced slowly. Cyclohexanone oxime rapidly evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine N-oxide and pyridine is reduced rapidly. Disulfides are rapidly reduced to the thiol stage whereas sulfoxide, sulfonic acid are practically inert to this reagent. Sulfones and cyclohexyl tosylate are slowly reduced. Octyl bromide is reduced rapidly but octyl chloride and cyclohexyl bromide are reduced slowly.

Dehydration of D-Xylose into Furfural Using Propylsulfonic Acid Modified Mesoporous Silica (황산 표면개질 메조다공 실리카를 이용한 푸르푸랄 제조에 관한 연구)

  • Kim, Eun-Gyu;Kim, Saet-Byul;Park, Eun-Duck;Kim, Sang-Wook
    • Clean Technology
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    • v.16 no.2
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    • pp.95-102
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    • 2010
  • Sulfonic acid (-SO3H) functionalized mesoporous silica containing HMS, SBA 15(S15), MCM 41(M41) were synthesized by post-synthesis and co-condensation method. Their catalytic performance is tested by dehydration reaction of D-xylose to furfural. As a result, good conversion and selectivity was obtained using water as an environmentally friendly solvent. Additionally, increased amounts of sulfuric acid in catalysts resulted in improved conversion of D-xylose. All of the acid-functionalized mesoporous silica showed higher selectivity than other solid acids such as ${\gamma}-Al_{2}O_{3}$ and zeolite.

Secretory Production of the Hericium erinaceus Laccase from Saccharomyces cerevisiae

  • Jin Kang;Thuat Van La;Mi-Jin Kim;Jung-Hoon Bae;Bong Hyun Sung;Seonghun Kim;Jung-Hoon Sohn
    • Journal of Microbiology and Biotechnology
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    • v.34 no.4
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    • pp.930-939
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    • 2024
  • Mushroom laccases play a crucial role in lignin depolymerization, one of the most critical challenges in lignin utilization. Importantly, laccases can utilize a wide range of substrates, such as toxicants and antibiotics. This study isolated a novel laccase, named HeLac4c, from endophytic white-rot fungi Hericium erinaceus mushrooms. The cDNAs for this enzyme were 1569 bp in length and encoded a protein of 523 amino acids, including a 20 amino-acid signal peptide. Active extracellular production of glycosylated laccases from Saccharomyces cerevisiae was successfully achieved by selecting an optimal translational fusion partner. We observed that 5 and 10 mM Ca2+, Zn2+, and K+ increased laccase activity, whereas 5 mM Fe2+ and Al3+ inhibited laccase activity. The laccase activity was inhibited by the addition of low concentrations of sodium azide and ⳑ-cysteine. The optimal pH for the 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt was 4.4. Guaiacylglycerol-β-guaiacyl ether, a lignin model compound, was polymerized by the HeLac4c enzyme. These results indicated that HeLac4c is a novel oxidase biocatalyst for the bioconversion of lignin into value-added products for environmental biotechnological applications.