• Natural Product Sciences
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• v.21 no.3
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• pp.192-195
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• 2015

An antibacterial benzoquinone, 2,6-dimethoxy-1,4-benzoquinone, isolated from Ficus foveolata stems was used as a standard marker for establishment of quantitative HPLC analysis for the stem extracts of F. foveolata. The method utilized a TSK-gel ODS-80Ts column (5 μm, 4.6 × 250 mm) with the mixture of methanol and 5% acetic acid in water (24:76, v/v) as the mobile phase at a flow rate of 1 mL/min, and quantitative detection at 289 nm. The parameters i.e. linearity, intraday and interday precision, accuracy, specificity and sensitivity of the method were evaluated for method validation. The recoveries of the method were 99.5 - 103.6% and good linearity (R² ≥ 0.9999) was obtained. A high degree of specificity, sensitivity as well as repeatability and reproducibility (RSD less than 2 and 5%, respectively) were also achieved. Chloroform was served as the most suitable solvent for extraction of 2,6-dimethoxy-1,4-benzoquinone. The optimised sample preparation and HPLC method can be practically used in the routine quality control process of F. foveolata stem extracts.

• Archives of Pharmacal Research
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• v.24 no.4
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• pp.312-315
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• 2001

Repeated column chromatographic separation of the $CH_{2}Cl_{2}$ extract of Artemisia stolonofera (Asteraceae) led to the isolation of a triterpene (I), a sesquiterpene (II), two aromatic compounds (III and IV) and a benzoquinone (V). Their structures were determined by spectroscopic means to be simiarenol (I), (1S,7S)-1 $\beta$-hydroxygermacra-4(15),5, 10(14)-triene (II), 3'-methoxy-4'-hydroxy-trans-cinnamaldehyde (III), vanillin(IV) and 2,6-dimethoxy-1,4-benzoquinone (V), respectively. Among these products, compound V showed significant cytotoxicity against five human tumor cell lines in vitro, A549 (non small cell lung adenocarcinoma), SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), XF498 (CNS) and HCT15 (colon) with ED_{50}$ values ranging from 1.33~4.22${\mu}g/ml$.

• Food Engineering Progress
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• v.14 no.4
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• pp.292-298
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• 2010

Wheat germ contains the glycosylated forms of 2-methoxy-p-benzoquinone (2-MBQ) and 2,6-dimethoxy-p-benzoquinone (2,6-DMBQ), both of which have antimicrobial and immunostimulatory effects. Conversion of glycosylated 2-MBQ and 2,6-DMBQ to their more functional unglycosylated forms requires enzymatic action of $\beta$-glucosidase. We investigated the applications of lactic acid bacteria and yeast that produce $\beta$-glucosidase as starters for production of unglycosylated 2-MBQ and 2,6-DMBQ from wheat germ. Lactobacillus zeae and Pichia pijperi were selected through $\beta$-glucosidase enzyme assays for 37 yeast strains and five strains of lactic acid bacteria. Lb. zeae was more efficient than P. pijperi at producing 2-MBQ and 2,6-DMBQ from wheat germ. After 48 hr of fermentation with a mixed culture of Lb. zeae and P. pijperi, the concentration of 2-MBQ was 0.46${\pm}$0.07 mg/g, indicating an approximately 1.6-fold higher concentration than that obtained by pure culture of Lb. zeae. However, the concentration of 2,6-DMBQ was not significantly enhanced by fermentation with a mixed culture of Lb. zeae and P. pijperi.

• Journal of Microbiology and Biotechnology
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• v.20 no.8
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• pp.1204-1209
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• 2010

We evaluated the antibacterial activities of selected edible Korean plant seeds against the food-borne pathogens Staphylococcus aureus KCTC1927, Escherichia coli KCTC2593, Salmonella typhimurium KCTC2054, and Bacillus cereus KCTC1014. While screening for antibacterial agents, we discovered that wheat germ extract contains 2,6-dimethoxy-1,4-benzoquinone (DMBQ) and is highly inhibitory to S. aureus and B. cereus. This is the first report of the antibacterial activity of wheat germ extract. We also investigated the antibacterial activities of the 1,4-benzoquinone standards 1,4-benzoquinone (BQ), hydroquinone (HQ), methoxybenzoquinone (MBQ), and 2,6-dimethoxy-1,4-benzoquinone (DMBQ). DMBQ and BQ were the most highly inhibitory to S. aureus and S. typhimurium, followed by MBQ and HQ. MICs for DMBQ and BQ ranged between 8 and 64 ${\mu}g/ml$ against the four foodborne pathogens tested. DMBQ and BQ showed significant antibacterial activity; the most sensitive organism was S. aureus with an MIC of 8 ${\mu}g/ml$. BQ exhibited good activity against S. typhimurium (32 ${\mu}g/ml$) and B. cereus (32 ${\mu}g/ml$). The results suggest that wheat germ extract has potential for the development of natural antimicrobials and food preservatives for controlling foodborne pathogens.

• Food Engineering Progress
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• v.23 no.1
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• pp.22-29
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• 2019

This study was carried out using Celluclast 1.5L to increase the content of 2,6-DMBQ and water extractable arabinoxylan in wheat germ extract. Extraction temperatures were 30℃, 45℃ and 60℃. The extraction times were 0, 6, 12, 18, 24 and 30 h. The pH of the extract decreased rapidly from 18 h at 30℃ in both water- and enzyme-treated extracts. 2,6-DMBQ of water- and enzyme-treated extracts increased with the extraction time. At 30-hour extraction time, enzyme-treated extract increased 27.60% at 30℃ extraction temperature than water extraction. Extraction temperatures of 45℃ and 60℃ were increased by 65.03% and 151.05%, respectively. The highest content of water-extractable arabinoxylan was 15.23±0.08 mg/g when the enzyme was treated at an extraction temperature of 60℃ for 30 h. At 30=hour extraction time, enzyme-treated extract increased 7.92% at 30℃ extraction temperature compared to water extraction. Extraction temperatures of 45℃ and 60℃ were increased by 31.20% and 54.38%, respectively.

• Proceedings of the Korean Society of Applied Pharmacology
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• 2001.11a
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• pp.80-80
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• 2001

The roots of Scutellaria baicalensis Georgi have been used in the chinese medicine for the treatment of inflammation, fever and headache. Recent studies had shown that baicalin and baicalein showed a detoxifying effect and could inhibit peripheral capillary permeability, and Wogonin was found to inhibit the proliferation of tumor cells. Wogonin has been synthesized as shown in schem. Compound 2 was prepared from 2,6-dimethoxy-1,4-benzoquinone(1) followed by acylation to give compound 3. The base treatment of 3 gave cyclized product which was carried by deprotection of methyl group chemoselectively. Overall step included relatively simple ten steps.

• Korean Journal of Food Science and Technology
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• v.51 no.2
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• pp.97-102
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• 2019

Wheat germ, which is rich in nutrients and phytochemicals, is a by-product during the milling process of wheat kernel. In this study, we aimed to increase the amount of bioactive 2,6-dimethoxy-1,4-benzoquinone (2,6-DMBQ) in wheat germ using the cell-wall-degrading enzyme cellulase (Celluclast 1.5L). The amounts of organic acids, free sugars, and 2,6-DMBQ in wheat germ treated with Celluclast 1.5L were evaluated at various reaction times and temperatures. The results of reversed-phase high-performance liquid chromatography of Celluclast 1.5L-treated wheat germ revealed 2,6-DMBQ, four organic acids (tartaric, acetic, lactic, and succinic acids), and three free sugars (sucrose, fructose, and glucose). As reaction time and temperature of the mixture of wheat germ and Celluclast 1.5L increased, the contents of four organic acids, glucose, fructose, and 2,6-DMBQ increased, but that of sucrose decreased. Taken together, these results suggest that Celluclast 1.5L-treated wheat germ containing increased amounts of 2,6-DMBQ serves as a source of functional ingredients in food industry.

• Natural Product Sciences
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• v.17 no.4
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• pp.267-272
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• 2011

In our search for bioactive phenolics from plants, the culms of Phyllostachys bambusoides has been selected for investigation of anti-cariogenic and 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging agents based on the initial screening results. Fractionation process of n-hexane and $CHCl_3$ extracts afforded four phenolic constituents, ferulic acid (1), vanillin (2), coniferaldehyde (3), and coniferyl alcohol (4) as guided by their DPPH free radical scavenging activities. Additionally, activity-guided fractionation of EtOAc extract with anti-cariogenic activity has resulted in the isolation of coniferaldehyde (3), 2,6-dimethoxy-p-benzoquinone (5), p-methoxycinnamic acid (6), (${\pm}$)-balanophonin (7), and 6-methoxychromanone (8). The structures of 1 - 8 were determined by spectroscopic data interpretation, and also by comparison of their data with the published values. Phenolic compounds 1 - 4 exhibited similar DPPH radical scavenging activities compared with the synthetic antioxidant, butylated hydroxytoluene (BHT), and compounds 3 and 5 - 8 showed significant antibacterial activity against cariogenic oral streptococci, Streptococcus mutans and S. sobrinus.

• Journal of the Korean Society of Food Science and Nutrition
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• v.42 no.7
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• pp.1003-1007
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• 2013

In this study, the antibacterial activities of selected barleys (UB, unhulled barley; PB, pearl barley; and NB, naked barley) and wheat (WG, wheat with germ and endosperm) extracts were evaluated against the food-borne pathogens Staphylococcus aureus KCTC 1927, Escherichia coli KCTC 2593, Salmonella Typhimurium KCTC 2054, and Bacillus cereus KCTC 1014. The amount of the antibacterial biomarker, 2,6-dimethoxy-1,4-benzoquinone (DMBQ), present in selected barleys and wheat, was measured by HPLC. Furthermore, antioxidant activity of samples was determined using the oxygen radical absorbance capacity (ORAC) assay. WG ($22.35{\pm}0.04mm$) was found to be highly inhibitory to Staphylococcus aureus followed by UB ($17.91{\pm}0.10mm$), PB ($16.87{\pm}0.05mm$), and NB ($15.69{\pm}0.20mm$). The antibacterial activity of the selected grains was correlated with antioxidant activities and the amount of DMBQ (Pearson's correlation coefficient, 0.7831). The antioxidant activity of the selected grains was also correlated with the total phenolic content (Pearson's correlation coefficient, 0.9934). WG extract showed significantly higher antibacterial activity, compared with barley extracts such as UB, PB, and NB. The results of this study suggest that barley has a potential in the development of natural antimicrobials and food preservatives for controlling food-borne pathogens.