• Korean Journal of Fisheries and Aquatic Sciences
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• v.54 no.5
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• pp.644-651
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• 2021

Viral hemorrhagic septicemia virus (VHSV) is a fish pathogen responsible for causing enormous economic loss to the aquaculture industry not only in Korea but worldwide. Thus, it is necessary to identify natural compounds that can be used to control the spread of VHSV. In this study, the anti-VHSV activities of five catechol derivatives, i.e., catechol, pyrogallol, 3-methyl catechol, veratrole, and 3-methyl veratrole-extracted from green tea-were assessed. The antiviral activities of these derivatives were found to be dependent on their structure, i.e., the hydroxyl or methoxyl group and their substituent groups-on the benzene ring. Catechol, pyrogallol, and 3-methyl catechol exhibited relatively high 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities than veratrole, and 3-methyl veratrole. Moreover, 3-methyl catechol harboring a methyl substituent group increased the viability of the virus-infected cells and resulted in a 2.86 log reduction in the gene copies of VHSV N (per mL) in real-time PCR analysis. In conclusion, the catechol derivatives harboring hydroxyl groups in their benzene ring exhibited higher antioxidant activities than those harboring the methoxyl groups. However, catechol derivatives with a methyl group at the 3'-position of the benzene ring exhibited higher antiviral activity than those harboring a hydroxyl group. To our knowledge, this is the first study to evaluate the relationship between the structure and the anti-VHSV activity of catechol derivatives.

• Microbiology and Biotechnology Letters
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• v.17 no.3
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• pp.224-230
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• 1989

For the production of catechol from benzene, bacteria capable of assimilating benzene as a sole carbon and energy source were isolated from soils. Among them, newly isolated strain, KY-114 hay-ing the best ability of producing catechol from benzene was selected and a mutant Pseudomonas sp. HW-103 was developed from Pseudomonas sp. KY-114 by using mutagenesis induced by N-methyl - N'- nitro - N -nitrobo guanidine. The catechol reduction from benzone by Pseudomonas sp. HW-103 was investigated under various conditions. The highest catechol concentration (0.61 g/$\ell$) was obtained in the growth medium (pH 6.5) containing 1% sodium citrate, 0.75% (NH$_4$)$_2$SO$_4$, 0.15% benzene and other minerals at 3$0^{\circ}C$ after incubating of 15hrs. In the catechol production through the reaction with resting rolls, 2.5 g/1 of catechol was produced from 4 g/$\ell$ of benzene after incubation of 10 hrs under the optium conditions, which correponds to 45% of theoretical catechol yield.

• YAKHAK HOEJI
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• v.37 no.1
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• pp.36-40
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• 1993

The 4-(2'-(N-(l-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-l- hydroxy-2-pyridone which has isoelectronic and isosteric structural similarity with dobutamine without having the Catechol-O- Methyltransferase(COMT) vulnerable m-hydroxy group was synthesized via 12 synthetic steps.

• Bulletin of the Korean Chemical Society
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• v.15 no.3
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• pp.198-204
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• 1994

Chemical shifts in aqueous sodium dodecylsulfate(SDS) micellar solution solublizing phenol, catechol, resorcinol, hydroquinone have been measured to investigate solubilization properties. Proton nuclear magnetic resonance frequencies of solubilizates as well as those of the ${\alpha}$-methylene, middle methylene and terminal methyl of SDS shift linearly as a function of solubilizate concentration. From the plots of observed chemical shift (v) vs solubilizate concentration, slope (a) and solubilizate free chemical shift ($v_0$) are obtained. They are very informative to solubilization site of the systems. Catechol and phenol solubilized SDS and catechol solubilized dodecylpyridinium chloride(DPC), dodecyltrimethylammonium bromide(DTAB) systems are studied using the same method to compare head group effect and middle methylene proton signal splitting. It is proposed that phenol and catechol are inserted into micellar interior and the number of methylenes assigned to the higher field peaks is 5.0${\pm}$0.5.

• YAKHAK HOEJI
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• v.39 no.5
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• pp.506-510
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• 1995

The 5-(2'-(N-(1-methyl-3'-carbamylphenyl)-n-propyl))aminoethyl)-8- hydroxy-4-methyl-carbostyril derivatives which have isoelectronic and isosteric structural similarity with dobutamine without having the Catechol-O-Methyltransferase (COMT) vulnerable m-hydroxy group were synthesized via 7 synthetic steps, and their stabilities in phosphate buffer solution(pH=7.4), human blood. 80% human plasma and 20% rat liver homogenate were determined in vitro condition.

• Journal of Microbiology and Biotechnology
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• v.9 no.3
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• pp.249-254
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• 1999

A catechol 2,3-dioxygenase (C23O) was purified to apparent homogeneity from Pseudomonas putida SU10 through several purification steps consisting of ammonium sulfate precipitation and chromatographies on DEAE 5PW, Superdex S-200, and Resource-Q. Gel filtration indicated a molecular mass under nondenaturing conditions of about 130 kDa. The enzyme has a subunit of 34 kDa as was determined by SDS-PAGE. These results suggest that the native enzyme is composed of four identical subunits. The N-terminal amino acid sequence (30 residues) of the enzyme has been determined and exhibits high identity with other extradiol dioxygenases. The reactivity of this enzyme towards catechol and methyl-substituted catechols is somewhat different from that seen for other catechol 2,3-dioxygenases, with 4-methylcatechol cleaved at a higher rate than catechol or 3-methylcatechol. $K_m$ values of the enzyme for these substrates are between 3.5 and 5.7 M.

• Bulletin of the Korean Chemical Society
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• v.18 no.11
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• pp.1166-1172
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• 1997

[FeⅢ(BLPA)DBC]BPh4, a new functional model for the catechol dioxygenases, has been synthesized, where BLPA is bis((6-methyl-2-pyridyl)methyl)(2-pyridylmethyl)amine and DBC is 3,5-di-tert-butylcatecholate dianion. The BLPA complex has a structural feature that iron center has a six-coordinate geometry with N4O2 donor set. It exhibits EPR signals at g=5.5 and 8.0 which are typical values for the high-spin FeⅢ (S=5/2) complex with axial symmetry. The BLPA complex reacts with O2 within a few hours to afford intradiol cleavage (75%) and extradiol cleavage (15%) products which is very unique result of all [Fe(L)DBC] complexes studied. The iron-catecholate interaction of BLPA complex is significantly stronger, resulting in the enhanced covalency of the metal-catecholate bonds and low energy catecholate to FeⅢ charge transfer bands at 583 and 962 nm in CH3CN. The enhanced covalency is also reflected by the isotropic shifts exhibited by the DBC protons, which indicate increased semiquinone character. The greater semiquinone character in the BLPA complex correlates well with its high reactivity towards O2. Kinetic studies of the reaction of the BLPA complex with 1 atm O2 in CH3OH and CH2Cl2 under pseudo-first order conditions show that the BLPA complex reacts with O2 much slower than the TPA complex, where TPA is tris(2-pyridylmethyl)amine. It is presumably due to the steric effect of the methyl substituent on the pyridine ring. Nevertheless, both the high specificity and the fast kinetics can be rationalized on the basis of its low energy catecholate to FeⅢ charge transfer bands and large isotropic NMR shifts for the BLPA protons. These results provide insight into the nature of the oxygenation mechanism of the catechol dioxygenases.

• Bulletin of the Korean Chemical Society
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• v.21 no.9
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• pp.923-928
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• 2000

[FeIII(BBA)DBC]ClO4 as a new functional model for catechol dioxygenases has been synthesized, where BBA is a bis(benzimidazolyl-2-methyl)amine and DBC is a 3,5-di-tert-butylcatecholate dianion.The BBA complex has a structuralfeature that iron cent er has a five-coordinate geometry similar to that of catechol dioxygenase-substrate complex.The BBA complex exhibits strong absorptionbands at 560 and 820 nm in CH3CN which are assigned to catecholate to Fe(III) charge transfer transitions. It also exhibits EPR signals at g = 9.3 and 4.3 which are typical values for the high-spin FeIII (S = 5/2) complex with rhombicsymmetry. Interestingly, the BBA complex reacts with O2 within an hour to afford intradiol cleavage (35%) and extradiol cleavage (60%) products. Surprisingly, a green color intermediate is observed during the oxygenation process of the BBA com-plex in CH3CN. This green intermediate shows a broad isotropic EPR signal at g = 2.0. Based on the variable temperature EPR study, this isotropic signalmight be originated from the [Fe(III)-peroxo-catecholate] species havinglow-spin FeIII center, not from the simple organic radical. Consequently,it allows O2 to bind to iron cen-ter forming the Fe(III)-superoxide species that converts to the Fe(III)-peroxide intermediate. These present data can lead us tosuggest that the oxygen activation mechanism take place for the oxidative cleavingcatechols of the five-coordinate model systems for catechol dioxygenases.

• Archives of Pharmacal Research
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• v.16 no.3
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• pp.213-218
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• 1993

($\pm$)-Higenamine is known as a cardiotonic principle of aconite root (root of Aconitum spp., Ranunculaceae). A simple and sensitive detection method for higenamine was developed by using gas chromatography-mass spectrometry (GC/MS). The recovery of higenamine after extraction and concentration with XAD-2 resin column was around 95% from rat biological fluids such as bile, plasma and urine. The limits of detection of higenamine in these biological fluids were approximately 0.1 ng/ml each. It has well been suggested that tetrahydroisoquinolines possessing catechol moiety such as higenamine should be subjected to the catechol-O-methyl transferase (COMT) activity in vivo. We detected two major peaks of presumed metabolites of higenamine in the total ion chromatogram obtained from the rat urine sample after the oral adminstration of ($\pm$)-higenamine. The scan mass spectrum of one of the metabolties coincided with those obtained from coclaurine $(C_6$-O-methyl higenamine) and those of the other metabolite are suggestive of isococlaurine $(C_7$-O-methyl higenamine).

• Journal of Environmental Health Sciences
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• v.18 no.2
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• pp.92-101
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• 1992

Halogen substituted-phenol and analog phenol degrading strains were identified as Aeromonas, Moraxella, and Flavobacterium genus. Optimal degrading condition was generally 50~100 $\mu$M substituted-phenol as carbon source, $NH_4NO_3$ as nitrogen source, 30$\circ$C , and initial pH 7.2. $\rho$-Chlorophenol degrading strain of Aeromonas sp. C4 had biodegradability to the various substituted-phenols. Flavobacterium sp. M9 had substrate specificity to methyl substituted-function. Catechol was cleavaged by catechol 1, 2-dioxygenase in Aeromonas sp. C4, Moraxella sp. N7, and Flavobacterium sp. M9.