• Advances in environmental research
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• 제4권1호
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• pp.39-48
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• 2015

Bisphenol A is widely used in plastic and other industrial consumer products. Release of bisphenol A and its analogues into the aquatic environment during manufacture, use and disposal has been a great scientific and public concern due to their toxicity and endocrine disrupting effects on aquatic wildlife and even human beings. More recent studies have shown that these alkylphenols may affect the molting processes and survival of crustacean species such as American lobster, crab and shrimp. In this study, we have developed gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometric (GC-MS) methods for the determination of bisphenol A and its analogues in shrimp Macrobrachium rosenbergii, blue crab Callinectes sapidus and American lobster Homarus americanus samples. Bisphenol A, 2,4-bis-(dimethylbenzyl)phenol and 4-cumylphenol were found in shrimp in the concentration ranges of 0.67-5.51, 0.36-1.61, and < LOD (the limit of detection)-1.96 ng/g (wet weight), and in crab of 0.10-0.44, 0.13-0.62, and 0.26-0.58 ng/g (wet weight), respectively. In lobster tissue samples, bisphenol A, 2-t-butyl-4-(dimethylbenzyl)phenol, 2,6-bis-(t-butyl)-4-(dimethylbenzyl)phenol, 2,4-bis-(dimethybenzyl)phenol, 2,4-bis-(dimethylbenzyl)-6-t-butylphenol and 4-cumylphenol were determined at the concentration ranges of 4.48-7.01, 1.23-2.63, 2.71-9.10, 0.35-0.91, 0.64-3.25, and 0.44-1.00 ng/g (wet weight), respectively. At these concentration levels, BPA and its analogs may interfere the reproduction and development of crustaceans, such as larval survival, molting, metamorphosis and shell hardening.

• Bulletin of the Korean Chemical Society
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• 제6권6호
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• pp.358-361
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• 1985

Thianthrene cation radical perchlorate (1) reacted with azo-bis-2-phenoxy-2-propane (6) to give thianthrene (2), cisthianthrene-5,10-dioxide, 5-(p-hydroxyphenyl) thianthrenium perchlorate (10), acetone, phenol, and 5-(2-propenyl) thianthrenium perchlorate (11) when the mole trtio of 1 to 6 was 1:1. Among the products, 11 was a new compound. However, when the corresponding mole ratio was 5:1, 11 was not formed. Similar result was obtained for azo-bis-2-(p-nitrophenoxy)-2-propane.

• Bulletin of the Korean Chemical Society
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• 제21권11호
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• pp.1111-1114
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• 2000

The kinetic study of the enaryloxynitriles via the nucleophilic vinylic substitution reaction of various phenol derivatives with 1-chloro-1-phenyl-2,2-dicyanoethene (1) was conducted in the presence of 1,4-diazabicyclo[2,2,2]octane (DABCO). Nucleo philic vinylic substitution of phenol derivatives with electrophilic olefins carrying sluggish leaving group involves a third-order reaction. The reaction was applied to solution polymerization of diphenol derivatives with p-bis(1-chrolo-2,2-dicyanovinyl)benzene (2), which yielded various polyenaryloxynitriles with moderate molecular weight.

• Biomolecules & Therapeutics
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• 제24권4호
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• pp.402-409
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• 2016

It has been found that 4-isopropyl-2,6-bis(1-phenylethyl)phenol (KTH-13), a novel compound isolated from Cordyceps bassiana, is able to suppress tumor cell proliferation by inducing apoptosis. To mass-produce this compound, we established a total synthesis method. Using those conditions, we further synthesized various analogs with structural similarity to KTH-13. In this study, we aimed to test their anti-cancer activity by measuring anti-proliferative and pro-apoptotic activities. Of 8 compounds tested, 4-methyl-2,6-bis(1-phenylethyl)phenol (KTH-13-Me) exhibited the strongest anti-proliferative activity toward MDA-MB 231 cells. KTH-13-Me also similarly suppressed the survival of various cancer cell lines, including C6 glioma, HCT-15, and LoVo cells. Treatment of KTH-13-Me induced several apoptotic signs in C6 glioma cells, such as morphological changes, induction of apoptotic bodies, and nuclear fragmentation and chromatin condensation. Concordantly, early-apoptotic cells were also identified by staining with FITC-Annexin V/PI. Moreover, KTH-13-Me highly enhanced the activation of caspase-3 and caspase-9, and decreased the protein level of Bcl-2. In addition, the phosphorylation levels of Src and STAT3 were diminished in KTH-13-Me-treated C6 cells. Therefore, these results suggest that KTH-13-Me can be developed as a novel anti-cancer drug capable of blocking proliferation, inducing apoptosis, and blocking cell survival signaling in cancer cells.

• Bulletin of the Korean Chemical Society
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• 제35권7호
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• pp.2038-2042
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• 2014

4-(tert-Octyl)phenol derivatives bearing the D-mannitol substructure (6a, 6b, 7) were prepared from $\small{D}$-mannitol and evaluated their anticancer activity against human lung (A549) and prostate (Lncap, Du145, PC3) cancer cell lines. Among derivatives tested, the bis(tert-octyl)phenoxy compound 7 exhibited strongest proliferation inhibitory activities against human cancer cell lines tested, especially high sensitivity to human Du145 prostate cancer cells ($IC_{50}=7.3{\mu}M$).

• 한국식품저장유통학회지
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• 제12권1호
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• pp.68-74
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• 2005

본 연구에서는 우리나라의 전통차의 계승과 새로운 식품의 개발하고자 생강나무의 잎을 이용한 차의 제조방법에 따른 향기성분의 변화를 조사하였다. 재차방법에 따른 향기성분은 덖음차 81종, 찐후덖음차 78종, 자연건조차 88종, 발효차 86종, 찐차 72종 및 인공건조차 89종의 분리할 수 있었다. 생강나무 잎차의 향기성분은 $\beta-piepne$을 비롯한 hydrocarbone류가 45종이 동정되었으며, 가장 많은 종류의 성분이 분포되었다. Alcohol류는 L-linalool, n-octanoal, phenyl acetaldehyde, $(-)-\alpha-terpineol$, elemol, cholest-5-en-3-ol, 등 16종, 2-nitro-2(3-hydroxybuthyl) -clododexanone, 3-(3-butenyl)-2,3-epoxy-cyclohexanone, 2-ethyl-2-propyl- cyclo-hexanone 등 11종의 ketone류가, phenyl acetaldehyde, tetradecanal, 10-undecanal, 4-Bromo-2- methylbutanal 등 8종의 aldehyde류가 동정되었다. 또한 ester류는 methyl 9, 12, 15-octadecatrienate, didodecyl phthalate, 1,2-benzenediccar-baboxy acid-bis(2-ethylhexyl) ester 3종류가 동정되었고, 또한 phenol류는 2,6-bis(1,1-dimethylethyl)-4-methyl-phenol이 동정되었다.

• Bulletin of the Korean Chemical Society
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• 제22권9호
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• pp.999-1004
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• 2001

(1-Chloro-2,2-dicyanovinyl)benzene or 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene was reacted with 2-amino-phenol to give the model compound, hydroxy enaminonitrile, which was found to undergo thermal cyclization reaction to form the corresponding benzoxazole. This intramolecular cyclization reaction is expected to occur through nucleophilic attack to electropositive enamine carbon by ortho-hydroxy group on the phenyl ring, which is accompanied by the release of neutral malononitrile through rearrangement. From each bifunctional monomer, o-hydroxy substituted polyenaminonitrile was prepared and characterized as a new precursor polymer for well-known aromatic polybenzoxazole. Also the unusual macrocyclic dimer formation from the 1,4-bis(1-chloro-2,2-dicyanovinyl)benzene and 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane polymerization reaction system was discussed. The thermal cyclization reactions and the properties of polymers were investigated using FT-IR and thermal analysis (DSC & TGA).

• The Korean Journal of Physiology and Pharmacology
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• 제20권3호
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• pp.253-259
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• 2016

Previously, we found that KTH-13 isolated from the butanol fraction of Cordyceps bassiana (Cb-BF) displayed anti-cancer activity. To improve its antiproliferative activity and production yield, we employed a total synthetic approach and derivatized KTH-13 to obtain chemical analogs. In this study, one KTH-13 derivative, 4-(tert-butyl)-2,6-bis(1-phenylethyl)phenol (KTH-13-t-Bu), was selected to test its anti-cancer activity. KTH-13-t-Bu diminished the proliferation of C6 glioma, MDA-MB-231, LoVo, and HCT-15 cells. KTH-13-t-Bu induced morphological changes in C6 glioma cells in a dose-dependent manner. KTH-13-t-Bu also increased the level of early apoptotic cells stained with annexin V-FITC. Furthermore, KTH-13-t-Bu increased the levels of cleaved caspase-3 and -9. In contrast, KTH-13-t-Bu upregulated the levels of pro- and cleaved forms of caspase-3, -8, and -9 and Bcl- 2. Phospho-STAT3, phospho-Src, and phospho-AKT levels were also diminished by KTH13-t-Bu treatment. Therefore, these results strongly suggest that KTH-13-t-Bu can be considered a novel anti-cancer drug displaying pro-apoptotic activity.

• The Plant Pathology Journal
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• 제38권1호
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• pp.33-45
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• 2022

To screen antagonistic fungi against plant pathogens, dual culture assay (DCA) and culture filtrate assay (CFA) were performed with unknown soil-born fungi. Among the different fungi isolated and screened from the soil, fungal isolate ANU-301 successfully inhibited growth of different plant pathogenic fungi, Colletotrichum acutatum, Alternaria alternata, and Fusarium oxysporum, in DCA and CFA. Morphological characteristics and rDNA internal transcribed spacer sequence analysis identified ANU-301 as Aspergillus terreus. Inoculation of tomato plants with Fusarium oxysporum f. sp. lycopersici (FOL) induced severe wilting symptom; however, co-inoculation with ANU-301 significantly enhanced resistance of tomato plants against FOL. In addition, culture filtrate (CF) of ANU-301 not only showed bacterial growth inhibition activity against Dickeya chrysanthemi (Dc), but also demonstrated protective effect in potato tuber against soft rot disease. Gas chromatography-tandem mass spectrometry analysis of CF of ANU-301 identified 2,4-bis(1-methyl-1-phenylethyl)-phenol (MPP) as the most abundant compound. MPP inhibited growth of Dc, but not of FOL, in a dose-dependent manner, and protected potato tuber from the soft rot disease induced by Dc. In conclusion, Aspergillus terreus ANU-301 could be used and further tested as a potential biological control agent.

• 한국응용과학기술학회지
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• 제33권3호
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• pp.521-528
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• 2016

The antioxidant activity of 70% methanol, 70% ethanol and chloroform-methanol (CM, 2:1, v/v) extracts from turmeric (Curcuma longa L.) was investigated in this study. The antioxidant potential of various extracts of turmeric was evaluated by using different antioxidant tests, namely DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity, ABTS [2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt] radical scavenging activity, ferric reducing antioxidant power and ${\beta}$-carotene bleaching assays as well as total phenol content and total flavonoid content. All extracts exhibited abundant total phenol content, total flavonoid content and strong antioxidant activity. Particularly, higher activity was exhibited by CM extract with $46.32{\pm}0.35mgCAE/g$ and $15.58{\pm}0.39 mgQE/g$ of total phenol content and total flavonoid content. Generally, antioxidant activity of various extracts from turmeric increased in the following order: 70% methanol extract, 70% ethanol extract and CM extract, respectively. Results suggested that turmeric could be widely used as a source of antioxidant and a kind of functional material in food.