• Bulletin of the Korean Chemical Society
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• v.32 no.1
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• pp.153-156
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• 2011

A concise synthesis of (${\pm}$)-rhinacanthin A is achieved in two steps by epoxidation of dehydro-$\alpha$-lapachone, followed by chemo- and regioselective reduction. Dehydro-$\alpha$-lapachone was also synthesized in two steps starting from 4-methoxy-1-naphthol by ethylenediamine diaetate (EDDA)-catalyzed benzopyran formation and a CAN-mediated oxidation reaction. $\beta$-Lapachone was synthesized in three steps from 4-methoxy-1-naphthol by benzopyran formation, catalytic hydrogenation, and Jones oxidation. As additional reactions, synthesis of pyranonaphthoquinone derivatives with the pyranokunthone B skeleton has been achieved in a single step from readily available 2-hydroxy-6-methoxy-1,4-naphthoquinone and 2-hydroxy-7-methoxy-1,4-naphthoquinone.

• Korean Journal of Environmental Biology
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• v.34 no.4
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• pp.281-291
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• 2016

Bloom of small centric diatom Stephanodiscus is quite occasional in winter season in temperate freshwater ecosystems. It often leads to degradation of water quality and affects the quality of supplied drinking water. In a previous study, we have found that naphthoquinone (NQ) 4-6 derivate is an effective tool for efficient mitigation of natural S. hantzschii blooms. In the present research, polylactide (PLA) and agar foam were used as immobilized agent for NQ 4-6 to improve the efficiency of NQ 4-6 compound releasing process for its application under various field conditions. Mesocosm experiments at 10 ton scale suggested that the abundance of S. hantzschii was continuously increased in the control and upon treatment of the mesocosm with immobilized NQ 4-6 from PLA and agar foam. Their algicidal activities were 78.8% and 77.1%, respectively, on S. hantzschii after 10 days. In the mesocosm experiments, the dynamics of biotic (bacteria, HNFs, ciliates, zooplankton) and abiotic (water temperature, dissolved oxygen, pH, conductivity, nutrients) factors remained unaffected. They exhibited similar trends in the control and treatment groups. Therefore, the immobilized NQ 4-6 from PLA and agar foam has potential to be used as an alternative algicidal substance to effectively mitigate natural S. hantzschii blooms under various field conditions. In addition, it not only can be used to control S. hantzschii, but also is an effective technique. The immobilized NQ 4-6 showed stable controlled release in desired system.

• Korean Journal of Pharmacognosy
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• v.27 no.3
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• pp.238-245
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• 1996

The activity guided fractionation of $CH_2Cl_2$ soluble part of Platycarya strobilacea leaves(Juglandaceae) has led to the isolation of eight active principles, identified as 5-hydroxy-2-methoxy-1,4-naphthoquinone(1), ursolic acid(2), gallic acid(3), 4,8-dihydroxynaphthalene $1-O-{\beta}-_D-glucoside(4)$, eriodictyol(5), quercetin $3-O-(2'-O-galloyl)-{\beta}-_D-glucoside(6)$. quercetin $3-O-(2'-O-galloyl)-{\beta}-_D-galactoside(7)$ and quercetin $3-O-{\alpha}-_L-rhamnoside(8)$ by the means of chemical and spectral evidence, respectively.

• Natural Product Sciences
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• v.15 no.1
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• pp.22-26
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• 2009

Phytochemical investigation of the roots of Echiochilon fruticosum resulted in the isolation of two naphthoquinone derivatives. Compound 1 was identified as anhydroalkanin while compound 2 was identified as a new derivative 5-hydroxy 8-methoxy 2-(4-methylpent-1,3-dienyl) naphthalene-1,4-dione named as echiochiloquinone. In addition, caffeic acid 3, caffeic acid methyl ester 4 were isolated. The structures were determined by physical, chemical and spectral methods. The anti-inflammatory activity of the root extracts and compound 2 was evaluated utilizing both cotton pellet-induced and carragenin-induced rat paw edema. The ulcerogenic effect was also studied.

• Journal of Microbiology and Biotechnology
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• v.12 no.5
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• pp.858-863
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• 2002

An antimicrobial compound was isolated from the MeOH extract of Catalpa ovata G.$D_{ON}$ fruits, and its structure was Identified as 4,9-dihydroxy-2,2-dimethyl-3,4-Uihydronaphtho[2,3-b]pyran-5,10-dione (HMNP). The antimicrobial activity of the Un was determined by measuring the dose-response inhibiton of microbial growth in liquid cultures and then compared with that of lapachol, a well known antimicrobial 1,4-naphthoquinone. The antimicrobial activity of the HMNP was more effective than that of lapachol over a wide range of test organisms. Gram-positive bacteria, yeast, and fungi ($IC_{50}$ $20-75\muM$) were found to be more sensitive to the HMNP than Cram-negative bacteria ($IC_{50}$ > $100\muM$). The HMNP also inhibited germination of spores of many fungi. The morphological defurmation of the fungal spores was induced by the treatment of HMNP, as illustrated by Scanning Electron Microscopy (SEM).

• Journal of the Korean Society of Clothing and Textiles
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• v.24 no.7
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• pp.1081-1087
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• 2000

Gromwell colorants were extracted with methanol and dried. Four fractions were obtained by silica gel adsorption column chromatography using step-wise elution method. Relative ratio of four fraction is 1.00:0.07:0.22:0.30(Fl:F2:F3:F4) and gromwell colorants mainly consist of Fl, F3 and F4. IR analysis shows that each fraction has similar structure. Main component of gromwell extracts is acetyl derivative of naphthoquinone, and the rest are isobutyl derivative and isovaleryl derivative etc., in order. Gromwell colorants exhibit relatively good affinity to protein and polyamide fibers, but low affinity to cellulose and regenerated cellulose fibers.

• Korean Journal of Plant Tissue Culture
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• v.24 no.3
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• pp.149-152
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• 1997

To search for a compound inhibiting the petunia callus growth from Streptomyces sp., we investigated the activity in the culture broth of 400 strains. The active compound was successively purified with solvent fractionation, silica gel column chromatography from Streptomyces sp. 9602 strain, and identified as 2, 5, 7-trihydroxy-3-(5'-hydroxyhexyl)-1, 4-naphthoquinone by 1H-NMR, EI-MS, IR and UV. It inhibited the callus growth of petunia by 50% at $32\mu\textrm{g}$/mL.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.336.2-336.2
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• 2002

Several 1 A-naphthoquinone derivatives have been reported to possess many pharmacological effects such as anti-viral. anti-fungal. anti-cancer and anti-platelet activities. We have reported that 2-chloro-3-［4-(ethyICarbOxy)-phenyl］-amino-1.4-naphthoquinone(NQ12) had a potent inhibitory effect on the platelet aggregation in vitro and thrombosis in vivo. However. little has been known about functional roleot NQ12 on vascular smooth muscle cells (VSMCs). (omitted)

• Archives of Pharmacal Research
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• v.22 no.4
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• pp.384-390
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• 1999

Thirty-four glutathione conjugates of 5,8-dimethoxy-1,4-naphthoquinones (DMNQ) were synthesized and their structure was determined. The yield of GSH conjugate was dependent on size of alkyl group; the longer the size of alkyl group was, the lower was the yield. It was also found that the length of alkyl side chain influenced the chemical shift of quinonoid protons; the quinonoid protons of 2-glutathionyl DMNQ derivatives with R=H to propyl, 6.51-6.59 ppm vs. other ones with R=butyl to heptyl, 6.64-6.68 ppm. this was explained to be due to a folding effect of longer alkyl group. Glutathione (GSH) reacted with DMNQ derivative first to form a 1,4-adduct (2- or 3-glutathionyl-1,4-dihydroxy-5,8-dimethoxynaphthalenes) and then the adduct was autooxidized to 2- or 3-glutathionyl-DMNQ derivatives. Moreover, GSH reduced DMNQ derivatives to their hydrogenated products. It was suggested that such an organic reaction might play an important role for a study of metabolism or toxicity of DMNQ derivative sin the living cells.

• Natural Product Sciences
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• v.13 no.4
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• pp.328-331
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• 2007

The methanolic extract of the roots of Lithospermum erythrorhizon (Boraginaceae) was found to show inhibitory activity towards farnesyl protein transferase (FPTase). Bioassay-guided fractionation of the methanolic extract resulted in the isolation of three naphthoquinone compounds, as inhibitors of FPTase. These compounds inhibited the FPTase activity in a dose-dependent manner.