• Journal of Haehwa Medicine
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• v.21 no.1
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• pp.125-133
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• 2012

본 논문은 피부미백에 관한 실험적 연구로서, 봉선화(Impatiens balsamina Linne)의 성분 중에서 하이드록시-나프타-퀴논(hydroxynaphthoquinone)이 멜라닌 생성억제 효능, 색소침착 저해 효과 등의 미백 활성이 있는 것으로 밝혀졌다. 피부흑화(melanogenesis)는 멜라닌 색소생성세포(melanocyte)에서 자외선 등의 자극에 대한 방어기작으로 멜라닌 생성 활동이 증가되고 이로 말미암아 만들어진 다량의 멜라닌이 각질형성세포(keratinocyte)로 전이되어 피부 표피층에 축척된 결과이다. 비록 멜라닌이 피부에 보호작용을 하나 피부의 과색소 침착은 기미, 주근깨, 피부염증 후의 피부흑화, 노인성 색소반점 등을 일으키며 이로 인해 피부미용 상의 불편뿐만 아니라 정신적으로 부정적인 영향을 미쳐 사회활동에 불편을 초래하기도 한다. 멜라닌 생성 과정은 아미노산의 일종인 티로신(tyrosine)에 티로시나제(tyrosinase)라는 효소가 작용하여 도파(DOPA), 도파퀴논(dopaquinone)으로 바뀐 후 비효소적인 산화 반응을 거쳐 만들어 지며, 이것이 피부 내에 이상 침착하여 기미, 검버섯 등이 생기는 것이라고 알려져 있다. 이와 같은 색소침착, 기미, 반점 등의 완화, 예방 및 치료에는 멜라닌 생성을 억제하는 물질, 예를 들면 하이드로퀴논(hydroquinone), 알부틴, 비타민 C 및 그 유도체 등이 개발되어 사용되고 있으나 이 중, 하이드로퀴논은 일단 효과가 인정되고 있지만 감작성이 있기 때문에 일반적으로 사용이 제한되고 있다. 아스콜빈산은 쉽게 산화되어, 이를 배합한 제품에는 변색, 변취가 되는 문제를 야기하고, 식물추출물 유래의 물질들은 식물의 산지에 따라 효능의 차이가 심하여 제품의 균질성이 유지되기 어렵다. 이러한 이유로 많은 멜라닌 생성을 억제하는 물질을 개발하기 위한 연구들이 계속 진행하고 있다. 2-히드록시-[1,4]나프토퀴논 유도체는 다음과 같은 구조를 나타낸다. 상기 구조에서 R은 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬로서, 바람직하게는 C1 내지 C10의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이고, 보다 바람직하게는 C1 내지 C5의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이다. 실험에 활용된 화합물은 다음과 같은 반응식으로 얻어졌다. 2-히드록시-[1,4]나프토퀴논과 포타슘카보네이트(K2CO3)를 아세토니트릴에 용해한 후, 저온수조로 냉각하고 알킬할라이드를 적당한 당량비로 천천히 적하하여 히드록시기와 에테르(ether) 반응을 통하여 얻어질 수 있다. 상기 반응식에서 R은 C1~10의 포화 또는 불포화된 알킬기로서 직쇄형 또는 분지쇄형 모두 가능하다. 상기 화합물인 2-히드록시-[1,4]나프토퀴논(2-hydroxynaphthoquinone)은 배양된 쥐의 멜라노마 세포에 대하여 하이드로퀴논과 대등한 멜라닌 생성 억제효과를 보였다. 하이드로퀴논은 저농도에서 강력한 멜라닌 생성 억제효과를 보이지만 상기 화합물들은 보다 낮은 농도에서도 세포독성을 나타내지 않으며 하이드로퀴논보다 높은 멜라닌 생성 억제 효과를 보였다.

• 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.

• YAKHAK HOEJI
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• v.36 no.2
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• pp.110-114
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• 1992

In order to evaluate the antimicrobial effect of 2, 3-substituted-1, 4-naphthoquinone derivatives, we newly synthesized several 2-chloro, 2-bromo and 2-hydroxy-1, 4-naphthoquinones and subjected to antibacterial and antifungal activities, in vitro, against Escherichia coli NIHJ, Staphylococcus aureus ATCC6538p, Candida albicans 10231, Aspergillus niger 1231 and Tricophyton mentagrophytes 6085. Among these derivatives 3, 9, 18 and 23 showed the potent antibacterial activities. 18, 23 and 28 have the antifungal activities. However, these compounds have no significant hemolytic activity at concentrations higher than that required for showing the antibacterial and antifungal activities.

• 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.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.

• Polymer(Korea)
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• v.30 no.2
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• pp.162-167
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• 2006

Polyamic acid (PAA) was prepared from cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA) and 4,4'-fiaminodiphenyl ether (DDE). In order to impart a photosensitivity to the PAA, diazonaphthoquinone (DNQ) derivative (DI) was added. However, the addition of the DI was not enough to inhibit the dissolution of the PAA for a aqueous alkal solution. Therefore, we had synthesized poly(amic acid ester)s by an adding 1,2-epoxy-3-phenoxypropane to the PAA. That is, an acidity of the PAA could be controlled by an esterification reaction of 1,2-epoxy-3-phenoxypropane with the PAA. Significant difference of a dissolution rate of the poly(amic acid ester) between an o(posed and unexposed area was observed at an acid content of 60% and less. Resolution of the positively patterned film showed about $25{\mu}m$ at the exposure dose of $200mJ/cm^2$.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.141-148
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• 2000

A new synthetic method of 6-(1-oxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones was developed, 2-formyl-1,4,5,8-tetramethoxynaphthalene was oxidized to form 6-formyl-5,8-dimethoxy-1,4-naphthoquinone(DMNQ). This was selectively reduced and benzylated to produce 6-formyl-5,8-dimethoxy-1,4-dibenzyloxynaphthalene, to which various alkylmagnesium halide were added, followed by debenzylation and oxidation in sequence, yielding 6-(1-hydroxyalkyl)-DMNQ derivatives. 6-(1-hydroxyalkyl)-5,8-diethoxy-1,4-naphthalene (DENQ) derivatives were synthesized by similar procedure. 1'-OH of the naphthoquinone derivatives was acylated with various alkanoic acids to give 6-(1-acyloxyalkyl)-DMNQ or DENQ derivatives. TOPO-I inhibitory activity and cytotoxicity of DENQs were less potent than that of DMNQs. Among the DMNQ and DENQ analogues, the ones with alkyl group being heptyl were most potent in TOPO-I inhibition $IC_{50}$/; 30.1, 36.4 $\mu$M). DUNQ derivatives with a longer side chain exhibited a weaker cytotoxicity. A correlation between size of the alkyl side chain and cytotoxicity was not observed for DENQ derivatives. Acylation of 1'-hydroxyl group, in general, decreased both TOPO-I inhibitory activity and cytotoxicity T/C (%) values of the DENQ derivatives on S-180 intraperitoneal tumor were larger than those of DMNQ derivatives. Among the compounds synthesized,6-(1-hydroxyheptyl)-DENQ and 6-(1-hex-anoyloxyoctyl)-DMNQ showed the highest T/C values of 183% and 182%, respectively.

• 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.

• Ecology and Resilient Infrastructure
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• v.2 no.3
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• pp.224-236
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• 2015

We conducted the algicidal activity screening tests using 10 L microcosm to investigate the possibility of the field application of naphthoquinone derivative Nq 4-6 compound as an algicide. We determined its application range to assess its algicidal effects on the phytoplankton and to evaluate the response of the planktonic community and the water environment to this chemical. From results of the microcosm experiments, Nq 4-6 compound showed high algicidal activity on the centric diatoms such as Stephanodiscus hantzschii and Cyclotella meneghiniana, but it had no effect on other phytoplankton. The abundance of S. hantzschii continuously increased in the control, but its cell density decreased 1 day after the Nq 4-6 treatment. In particular, Nq 4-6 showed algicidal activity of 94.4% against S. hantzschii 7 days after the treatment. The dominance index of phytoplankton community was lower in the treatment than in the control. The diversity index, richness index and evenness index of phytoplankton community was higher in the treatment. Environmental factors and biological factors did not show specific changes after the Nq 4-6 compound treatment. Therefore, the results of this study demonstrates that Nq 4-6 is an effective agent for the control of S. hantzschii blooms, and that the microcosm tests play a crucial role when assessing field application.