• Ecology and Resilient Infrastructure
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• v.7 no.1
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• pp.72-81
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• 2020

Blooms of the small centric diatom Stephanodiscus is quite occasional in winter season in temperate freshwater ecosystems. Often, it leads to degradation of water quality and affects quality of supplied drinking water. In previous studies, naphthoquinone (NQ) compounds have been shown to be effective and selective for controlling winter bloom species Stephanodiscus hantzschii. We conducted a 5 ton scale mesocosm experiment to investigate the effects of NQ on native Stephanodiscus sp. collected from Nakdonggang River in water. After treatment with NQ 4-6 compound (0.2 μM), the cell density of Stephanodiscus sp. was rapidly reduced from 5 × 10³ cells mL^-1 to 0.2 × 10³ cells mL^-1 for 10 days. Additionally, NQ 4-6 compound did not affect physicochemical factors (water temperature, dissolved oxygen, pH, conductivity, nutrients) and biological factors (bacteria, heterotrophic nanoflagellates, zooplankton). Therefore, these findings suggest that the NQ 4-6 compound has potential as an alternative algicidal substances to effectively mitigate natural Stephanodiscus sp. blooms, and the application of NQ 4-6 compound will restore the healthy aquatic ecosystems.

• 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.

• Proceedings of the PSK Conference
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• 2001.04a
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• pp.119.2-119.2
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• 2001

• Archives of Pharmacal Research
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• v.22 no.4
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• pp.414-416
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• 1999

A shkionin derivative was isolated from the roots of Lithospermum erythrorhizon with silica gel column chromatography and preparative TLC. The structure of the isolated pigment was identified as propionylshikonin by NMR and mass spectrometric analysis. The isolation of propionylshiknin was for the first time in the nature.

• 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).

• Ecology and Resilient Infrastructure
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• v.4 no.3
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• pp.130-141
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• 2017

We evaluated the field application feasibility that biologically derived substances (Naphthoquinone derivate: NQ 2-0) can be used for the eco-friendly mitigation of natural harmful cyanobacterial blooms in freshwater. We conducted a 30 ton scale mesocosm experiment to investigate the effects of NQ 2-0 on biotic and abiotic factors in water collected from Gi-heung reservoir. In the mesocosm experiments, the abundance of Microcystis sp. was continuously increased in the control. However, the Microcystis sp. cell density was sharply decreased on the $10^{th}$ day. In the treatment, NQ 2-0 showed the strong and selective algicidal activity toward the target cyanobacteria (Microcystis sp.). Accordingly, the algicidal activity of NQ 2-0 compound increased gradually until $10^{th}$, $15^{th}$ days and algal biomass was decreased to 99.4 and 100 %, respectively. NQ 2-0 compound was not only selective algicidal activity but also the growth of other phytoplankton and increased the Shannon-Wiener diversity index of phytoplankton. In the mesocosm experiments, the dynamics of biotic (bacteria, heterotrophic nanoflagellate, ciliates, zooplankton) and abiotic (water temperature, dissolved oxygen, pH, conductivity, nutrients) factors remained unaffected. These results suggest that NQ 2-0 could be a selective and ecologically safe algicide to mitigate harmful cyanobacterial blooms. In addition, it is believed that NQ 2-0 will play a major role in forming a healthy aquatic ecosystem by facilitating habitat and food supply of aquatic organisms.

• Ecology and Resilient Infrastructure
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• v.3 no.1
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• pp.22-34
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• 2016

We developed a biologically-derived substance naphthoquinone (NQ) derivate for the eco-safe mitigation of harmful cyanobacteria blooms such as Microcystis and Dolichospermum. NQ was reacted with various substituents ($R_n$) to produce different NQ derivatives. We tested a total of 92 algicidal compounds based on the algicidal activity of Microcystis and Dolichospermum. 22 compounds of NQ were selected as candidates (algicidal activity >80% at $1{\mu}M$). Among them, NQ 40 compound showed the highest algicidal activity of 99.6% and 100% at the optimal concentration of $1{\mu}M$ on Microcystis and Dolichospermum, respectively. No algicidal effects of NQ 40 ($1{\mu}M$) were observed against non-target algae such as Stephanodiscus, Cyclotella and Peridinium. According to the results of acute eco-toxicity assessment, the $EC_{50}$ values of NQ 40 compound for Selenastrum capricornutum and Daphnia magna were 3.2 and $14.5{\mu}M$, respectively, and the $LC_{50}$ for Danio rerio was $15.7{\mu}M$. In addition, for D. magna chronic eco-toxicity assessment, no toxicity toward survival, growth and reproduction was observed. Therefore, we suggested the NQ 40 ($1{\mu}M$) compound as an alternative eco-safe algicidal substance to effectively mitigate harmful cyanobacteria blooms.

• Korean Journal of Environmental Biology
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• v.38 no.1
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• pp.114-126
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• 2020

Bloom-forming toxic cyanobacteria Microcystis spp. are common in the summer season in temperate freshwater ecosystems. Often, it leads to the degradation of water quality and affects the quality of drinking water. In a previous study, NQ (naphthoquinone) compounds were shown to be effective, selective, and ecologically safe algicides for Microcystis spp. blooms. To analyze the superiority of developed NQ derivatives, we conducted a microcosm experiment using clay, which is frequently used in South Korea. Similar to previous studies, the NQ 40 and NQ 2-0 compounds showed high algicidal activities of 99.9% and 99.6%, respectively, on Microcystis spp. at low concentrations (≥1 μM) and enhanced phytoplankton species diversity. However, when treated with clay, a temporary algicidal effect was seen at the beginning of the experiment that gradually increased at the end. In addition, treatment with the NQ compounds did not affect either the abiotic or biological factors, and similar trends were observed with the control. These results showed that the NQ 2-0 compound was more effective, with no ecosystem disturbance, and more economical than the currently used clay. These results suggest that NQ 2-0 compound could be a selective, economically and ecologically safe algicide to mitigate harmful cyanobacterial blooms in the field.

• Advances in Traditional Medicine
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• v.5 no.4
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• pp.283-293
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• 2005

Our previous study showed that a novel synthetic shikonin derivative, 6-(1-hydroxyimino-4-methylpentyl)5,8-dimethyoxy 1,4-naphthoquinone S-52 (DMNQ S-52) induced apoptosis. In the present study, we investigated its anti-metastatic activities as compared with shikonin because DMNQ S-52 was synthesized for overcoming weak points of shikonin such as high toxicity, low solubility and deleterious effects. DMNQ S-52 showed the weaker cytotoxicity $(IC_{50};\;12.3{\pm}1.6\;{\mu}M)$ against Lewis lung carcinoma (LLC) cells than that of shikonin $(IC_{50};\;4.2{\pm}1.1\;{\mu}M)$. DMNQ S-52, at non-toxic concentrations $(less\;than\;10\;{\mu}M)$, significantly inhibited the invasion and migration of LLC cells. DMNQ S-52 also significantly inhibited the production of MMP-9, MTl-MMP and uPAR. Moreover, daily i.p. administration of DMNQ S-52 at dose of 5 mg/kg in mice resulted in a potent inhibition of the primary tumor size of LLC in the lung as well as the metastasis of lymph nodes. These findings suggest that the DMNQ S-52 has therapeutic potential to inhibit metastasis via inhibition of MMP family and uPA/plasminogen system.

• Biomolecules & Therapeutics
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• v.23 no.5
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• pp.428-433
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• 2015

Acetylshikonin, a natural naphthoquinone derivative compound, has been used for treatment of inflammation and cancer. In the present study, we have investigated whether acetylshikonin could regulate the NF-${\kappa}B$ signaling pathway, thereby leading to suppression of tumorigenesis. We observed that acetylshikonin significantly reduced proliferation of several cancer cell lines, including human pancreatic PANC-1 cancer cells. In addition, acetylshikonin inhibited phorbol 12-myristate 13-acetate (PMA) or tumor necrosis-${\alpha}$ (TNF-${\alpha}$)-induced NF-${\kappa}B$ reporter activity. Proteome cytokine array and real-time RT-PCR results illustrated that acetylshikonin inhibition of PMA-induced production of cytokines was mediated at the transcriptional level and it was associated with suppression of NF-${\kappa}B$ activity and matrix metalloprotenases. Finally, we observed that an exposure of acetylshikonin significantly inhibited the anchorage-independent growth of PANC-1 cells. Together, our results indicate that acetylshikonin could serve as a promising therapeutic agent for future treatment of pancreatic cancer.