• Microbiology and Biotechnology Letters
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• v.47 no.2
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• pp.242-249
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• 2019

Biosynthesis of indole-3-acetate (IAA) from L-tryptophan via indole-3-pyruvate pathway requires three enzymes including aminotransferase, indole-3-pyruvate decarboxylase, and indole-3-acetate dehydrogenase. To establish a bio-based production of IAA, the aspC, ipdC, and iad1 from Escherichia coli, Enterobacter cloacae, and Ustilago maydis, respectively, were expressed under control of the tac, ilvC, and sod promoters in C. glutamicum. Cells harboring ipdC produced tryptophol, indicating that the ipdC product is functional in this host. Analyses of SDS-PAGE and enzyme activity revealed that genes encoding AspC and Iad1 were efficiently expressed from the sod promoter, and their enzyme activities were 5.8 and 168.5 nmol/min/mg-protein, respectively. The final resulting strain expressing aspC, ipdC, and iad1 produced 2.3 g/l and 7.3 g/l of IAA from 10 g/l L-tryptophan, respectively, in flask cultures and a 5-L bioreactor.

• Bulletin of the Korean Chemical Society
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• v.5 no.3
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• pp.121-126
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• 1984

The charge transfer complex formations between indole derivatives and methylviologen were investigated spectroscopically. In aqueous solutions near room temperature, the order of complex stability was tryptamine < tryptophan < indole < indole acetate, which is the reverse order of the magnitude of molar absorptivities. This was interpreted as involvement of contact charge transfer. The decrease of enthalpy of complex formation (-${\Delta}$H) was highest in tryptamine, and lowest in indole acetate. ${\Delta}$H and entropy of complex formation (${Delta}$S) varied nearly in a linear fashion with isokinetic temperature $242^{\circ}$K. These results were attributed to the hydration-dehydration properties of the side chains in indole derivatives. Except indole acetate, the complex formations were greatly enhanced by the addition of sodium dodecyl sulfate(SDS). However, the direct relationship between the enhanced complex formation and SDS micelle formation was not found. The enhanced charge transfer interaction inSDS solutions was attributed to the increased ${\Delta}$S by interaction between methylviologen and SDS in premicellar level. The order of complex stability in SDS solutions was indole acetate < tryptophan < trypamine < indole, which reflects the hydrophobicity of indole derivatives as well as electrostatic interaction between indole derivatives and methylviologen associated with SDS.

• Bulletin of the Korean Chemical Society
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• v.6 no.3
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• pp.145-148
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• 1985

The effect of anionic polyelectrolytes, poly(styrenesulfonate) (PSS) and poly(vinylsulfonate) (PVS), on the charge transfer complexing between indole derivatives and methyl viologen($MV^{++}$) cation was investigated. The results were compared with effect of NaCl and an anionic surfactant, sodium dodecylsulfate (SDS). Both PSS and PVS enhanced the complex formation of neutral species (indole and indole acetate at low pH), zwitter ionic tryptophan, and positively charged tryptamine and tryptophan at low pH with $MV^{++}$. This result was attributed to the contribution of hydrophobic interaction, in addition to electrostatic interaction. The enhancing effect of PSS was much higher than that of PVS reflecting the higher hydrophobicity of PSS. The interaction between indole acetate anion and $MV^{++}$ was greatly reduced by addition of PVS and PSS. The higher charge density of PVS was appeared as greater reducing effect indicating the importance of electrostatic force in this case. In all cases, the effect of polyelectrolytes showed maxima, and further addition of PVS and PSS decreased the effect. This behavior was explained in terms of distribution of indole derivatives and $MV^{++}$ in domain of polyanions. The complex formation constants and molar absorptivities of complexes were determined, and the values were compared with those in water and SDS solutions.

• Applied Chemistry for Engineering
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• v.10 no.1
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• pp.135-137
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• 1999

For the synthesis of new anti-inflammatory agents as indol derivatives, we have synthesized ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester. It was a new method for ${\alpha}$-substituted etodolac carboxylic acid. The synthetic process was composed of four steps, and 7-ethylindole and oxalyl chloride were used as starting materials. The third step, cyclization was carried out by addition of borontrifluoride diethyl etherate in 66% yield. The step of reduction and cyclization were simplified successfully. The final product, ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester was obtained in 66% yield by the reaction of methyl 1,8-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate (etodollic acid methyl ester) and benzoyl chloride.

• YAKHAK HOEJI
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• v.34 no.1
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• pp.15-21
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• 1990

-4,9-dione derivatives were prepared from $2-chloro-3-({\alpha}-accetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. $2-Chloro-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ was reacted with amines to give $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ derivatives. Subsequent treatment of $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium ${\alpha}-cyano$ ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.

• Archives of Pharmacal Research
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• v.15 no.1
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• pp.1-4
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• 1992

4-Acetylantipyrine 1 underwent condensation with 4-formyl-antipyrine 2 to give 3. Condensation of either 3 with 1 or 1 with 2 in a molar ratio of (2 :1) afforded 4. Cyclization of 4 in the presence of PPA and ammonium acetate or 4-aminoantipyrine in the presence of glacial acetic acid gave 5-6 respectively. Claisen condensation of 1 with ethyl acetate and diethyl oxalate afforded compounds 8-10. The reaction of 1 and 2 with indole in ethanol/conc. hyddrochloric acid was also investigated.

• Journal of the Korean Society of Food Science and Nutrition
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• v.41 no.12
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• pp.1701-1707
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• 2012

3,3'-Diindolylmethane (DIM) is a major in vivo derivative of the putative anticancer agent indole-3-carbinol, which is present in cruciferous vegetables and has been reported to have anti-carcinogenic properties. An abnorrmally elevated level of cyclooxygenase-2 (COX-2) has been implicated in the pathogenesis of carcinogenesis. To investigate the mechanism by which DIM exhibits anti-carcinogenic effects, we investigated the effects of DIM on COX-2 expression in MCF-10A human mammary epithelial cells treated with the tumor promoter 12-O-tetradecanoylphorbol 13-acetate (TPA). DIM inhibited TPA-induced COX-2 expression and suppressed the synthesis of prostaglandin $E_2$, one of the major products of COX-2. Nuclear factor-kappa B ($NF-{\kappa}B$) is a transcription factor known to play a role in regulation of COX-2 expression. Treatment of MCF-10A cells with TPA increased nuclear translocation of phospho-p65, with the maximal levels being reached at 1 hour, while DIM inhibited the TPA-induced nuclear translocation of phospho-p65. Overall, we demonstrated that DIM suppresses phorbol ester-induced $PGE_2$ production and COX-2 expression in MCF-10A cells. The reduction in COX-2 levels by DIM maybe mediated through inhibition of $NF-{\kappa}B$ signaling.

• Microbiology and Biotechnology Letters
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• v.24 no.1
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• pp.105-110
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• 1996

Mugwort has been known as a traditional substitutive foodstuff and as showing a physiologically beneficial function to a human being. Therefore, effect of mugwort extract in terms of mutagenicity and desmutagenicity was investigated to berify its function. Ethanol extract from mugwort did not exhibit any mutagenicity. On the contrary, inhibitory effects of the ethanol extract were observed on mutagenicity induced by aflatoxin $B_{1}(AFB_1)$, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole(Trp-P-1), 3-amino-1-methyl-5H-pyrido[4,3-b]indole(Trp-P-2) and 2-nitroflourene(2NF) using Salmonella typhimurium reversion assay. On direct-acting mutagen(2NF, 3${\mu}$g/plate), ethanol extract showed a slight inhibitory effect of 19.7~22.9%, however on indirect-acting mutagen such as AFB1(2${\mu}$g/plate), Trp-P-1(1${\mu}$g/plate) and Trp-P-2(1${\mu}$g/plate), we observed higher inhibitory effect of 47.9~61.2%, 64.1~70.7%, 67.4~78.7%, respectively. Step-wise fractionation of the ethanol extract was done by using hexane, chloroform, ethyl acetate and water to obtain effective fraction. Among them, hexane, chloroform, and ethyl acetate fractions showed high inhibition of 63.0~80.0%, 77.5~82.1%, and 68.5~83.1%, respectively on the mutagenicity of $AFB_1$ in Sal. typhimurium TA98. Consequently, these results indicated that mugwort extract contains some compound(s) which may show desmutagenicity.

• Korean Journal of Food Science and Technology
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• v.31 no.4
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• pp.1065-1070
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• 1999

This study was performed to determine the antimutagenic and cytotoxic effect of Aster scaber root ethanol extract on Salmonella typhymurium TA98, TA100 and cancer cell lines using Ames test and cytotoxicity assay, respectively. Cancer cell lines include chronic myelogenous leukemia(K562), human gastric carcinoma(KATOIII), human hepatocellular carcinoma(Hep3B) and human breast adenocarcinoma(MCF-7). Futher fractionations with hexane, chloroform, ethyl acetate, butanol and water from ethanol extract of Aster scaber root were performed to obtain effective fraction. Ethanol extract and ethyl acetate fraction showed 79% and 82% inhibitory effect on the mutagenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine(MNNG) against TA100, while 48% and 60% inhibition was observed on the mutagenesis induced by 4-nitroquinoline-l-oxide(4NQO) against TA98. In the meanwhile, ethyl acetate fraction showed 78% and 85% inhibitory effect on the mutagenesis induced by benzo(${\alpha}$)pyrene[B(${\alpha}$)P] against TA98 and TA100, respectively, while 83% inhibition was observed on the mutagenesis induced by 3-amino-l,4-dimethyl-5H-pyrido(4,3-b) indole(Trp-P-1) against TA98. Ethyl acetate fraction (0.125 mg/ml) showed the strongest cytotoxic effect against K562, KATOIII, Hep3B and MCF-7 at the same concentration compared to those of other fractions. Ethanol extract and water fraction showed the least inhibitory effect.

• Natural Product Sciences
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• v.26 no.3
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• pp.214-220
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• 2020

Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH₂Cl₂), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H₂O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH₂Cl₂ fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of ¹³C and ¹H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.