• Korean Journal of Weed Science
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• v.31 no.3
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• pp.240-249
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• 2011

The potential of juglone a plant naphthoquinone as a natural herbicide on new target, 7-keto-8-amino pelargonic acid synthetase (KAPAS) in the early step of biotin biosynthesis pathway, was performed in vitro and in vivo. Juglone effectively inhibited KAPAS activities in vitro and the $IC_{50}$ was $9.5{\mu}M$. Foliar application of juglone showed very good herbicidal activity to the eight-tested weed species. Among them, Solanum nigrum was completely controlled at a concentration of $250{\mu}g\;mL^{-1}$ with main symptoms of desiccation or burndown. Digitaria sanguinalis and Aeschynomene indica were also sensitive to juglone treatment. All eight weed species were controlled by 90~100% at a concentration of $500{\mu}g\;mL^{-1}$. However, soil application of juglone to Digitaria sanguinalis did not show any herbicidal symptoms. Cellular leakage from cucumber leaf squares treated with juglone increased depending on the concentrations increased from 6.25 to $100{\mu}M$ after 24 hours incubation with or without light. However, chlorophyll loss in cucumber leaf squares was negligible. Biotin supplements significantly rescued the inhibition of germination rate of Arabidopsis thaliana seeds previously inhibited by the juglone. Our results suggest that the juglone is a possible environmental friendly herbicide candidate with a new target KAPAS inhibiting activity.

• Bulletin of the Korean Chemical Society
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• v.34 no.1
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• pp.68-74
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• 2013

The surface enhanced Raman spectrum of juglone, a traditional natural dye, has been observed by a custom-built micro-Raman setup. The spectral features of juglone significantly differ from those of lawsone, a structural isomer of juglone; only small red shifts of the double bond stretching bands are observed, and strong SERS bands are observed in the lower frequency regions as well. The DFT computations reveal that juglone coordinated to an $Ag^+$ adatom with $H^+$ release best correlates with the observed vibrational characteristics in the SERS spectrum among the plausible configurations of juglone coordinated to an adatom on the Ag surface, in line with the previously studied lawsone case. The differences in the SERS spectra of juglone and lawsone are attributed to the different locations of the hydroxyl group in the two isomers.

• Journal of Microbiology and Biotechnology
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• v.16 no.10
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• pp.1591-1596
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• 2006

Acaricidal effects of materials derived from Caesalpinia sappan heartwoods against Dermatophagoides farinae and D. pteronyssinus were assessed and compared with those evidenced by commercial benzyl benzoate and DEET. The observed responses varied according to dosage and mite species. The $LD_{50}$ values of the methanol extracts derived from C. sappan heartwoods were 6.13 and $5.44{\mu}g/cm^3$ against D. farinae and D. pteronyssinus, respectively. Furthermore, the ethyl acetate fraction derived from the methanol extract was approximately 8.71 more toxic than DEET against D. farinae, and 4.73 times more toxic against D. pteronyssinus. The biologically active constituent from the ethyl acetate fraction of C. sappan heartwood extract was purified via silica gel chromatography and high-performance liquid chromatography. The structure of the acaricidal component was analyzed by $GC-MS,\;^1H-NMR,\;^{13}C-NMR,\;^1H-^{13}C\;COSY-NMR$, and DEPT-NMR spectroscopy, and identified as juglone (5-hydroxy-l,4-naphthoquinone). Based on the $LD_{50}$ values of juglone and its derivatives, the most toxic compound against D. farinae was juglone ($0.076{\mu}g/cm^3$), followed by benzyl benzoate ($9.143{\mu}g/cm^3$) and 2methyl-l,4-naphthoquinone ($40.0{\mu}g/cm^3$). These results indicate that the acaricidal activity of C. sappan heartwoods is likely to be the result of the effects of juglone. Additionally, juglone treatment was shown to effect a change in the color of the cuticles of house dust mites, from colorless-transparent to dark brownish-black. Accordingly, as a naturally occurring acaricidal agent, C. sappan heartwood-derived juglone should prove to be quite 'useful as a potential control agent, lead compound, and house dust mite indicator.

• Journal of the Korean Society of Clothing and Textiles
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• v.30 no.12 s.159
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• pp.1708-1713
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• 2006

The purpose of this study is to investigate the efficacy of juglone, which shows hish affinity to wool, for hair dyeing as a natural dye. Before dyeing hair with juglone, virgin hair was bleached by a conventional method using hair shops in the city. In order to study the dyeing properties of juglone on hair, the effects of dyeing conditions on dye uptake, color, tensile strength, and morphology were investigated. And the effect of Fe-mordanting on color change was also investigated. Dye uptake changed marginally as dye concentration increased in the range of 0.02-0.04g. Dye uptake increased progressively is dyeing time increased in the range of 10-20 min. Juglone produced YR colors on hair and the color of dyed hair got duller as juglone concentration increased. The hair was little damaged by bleaching, but cuticles were melted and stripped away by dyeing for longer time. Tensile strength retention decreased up to 65% at 20 min dyeing. Simultaneous mordanting with Fe did not improved dye uptake, but led to darker brown color compared with unmordanted hair.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.185.3-185.3
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• 2003

Juglone and naphthazarine derivatives were newly systhesized for the evaluation of antifungal activities. These derivatives were prepared by methylation of juglone and 2, 3-dichloro-5, 8-dihydroxy-l, 4-naphthoquinone, and by regioselective nucleophilic subsitution with arylthiols. All compounds were tested in vitro for their growth inhibitory activities against pathogenic fungi by the standard method. The MIC values were determined by comparison to flucytosine as a standard agent. (omitted)

• Korean Journal of Pharmacognosy
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• v.27 no.4
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• pp.301-308
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• 1996

Hairy roots induced from stems of Rubia cordifolia var. pratensis were cultured in the liquid medium under a variety of auxins to find the optimal condition for the growth and production of pigments. Culture of the hairy roots on NN liquid medium containing NAA 0.5 mg/l was best for growth of hairy roots. Production of yellow anthraquinone derivatives and purpurin in hairy roots was enhanced by the culture on NN liquid medium without auxins. Effects of L-phenylalanine, L-tyrosine and juglone, synthesized via the shikimic acid pathway, on growth and production of pigments in hairy roots were studied in the present study. Concentration of exogeneous L-phenylalanine. L-tyrosine and juglone in liquid culture system of hairy root containing NAA 0.1 mg/l was decreased quickly in its early stages of the culture period. Addition of juglone to NN liquid medium containing NAA 0.1 mg/l enhanced the productivity of pigments in hairy roots.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.350.3-351
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• 2002

2-Arylthio-, 2-arylthio-5-methoxy-, 2, 3-bisarylthio-juglones and 2, 3-bisarylthio-5, 8-dimethoxy-1, 4-naphthoquinones were newly systhesized for the evaluation of antifungal activities. These derivatives were prepared by methylation of juglone and 2, 3-dichloro-5, 8-dihydroxy-1, 4-naphthoquinone. and by resioselective nucleophilic subsitution with arylthiols. All compounds were tested in vitro for their growth inhibitory activities against pathogenic fungi by the standard method. The MIC values were determined by comparison to flucytosine as a fungicidal standard agent. In general. In general. most juglone derivatives shows in vitro antifungal activities. Among them. 2-arylthio-5-methoxy-juglones showed most potent antifungal activities against all pathogenic fungi.

• Journal of Korean Society of Forest Science
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• v.97 no.3
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• pp.199-203
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• 2008

By comparison of mass fragmentation pattern of each component with two modern MS libraries (NIST and Wiely 6), those were identified to one aliphatic alcohol (3-ethyl-2-methyl-1-pentene-3-ol) and three naphthoquinone derivatives (1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone (juglone) and 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin)). According to the quantitative study with authentic compounds of three naphthoquinone derivatives, 1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone were the major volatile components in the root shell of Juglans mandshurica and their amounts were ca. $54.4{\mu}g/g$ and $21.3{\mu}g/g$, respectively.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1994.04a
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• pp.248-248
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• 1994

목적 : 가래나무는 일부 민간방과 한방에서 암 치료의 목적으로 사용되고 있다. 아울러 이 식물을 대상으로 세포독성물질의 분리, 구조결정에 관한 연구는 이미 보고되어 있는 성분인 juglone이 새포독성을 나타낸다는 단편적인 보고만 있을뿐 전혀 되어있지 않은 상태이다. 본 연구는 국내에서 자생하는 가래나무 (Juglans mandchurica)로부터 세포독성물질을 분리, 구조결정함으로서 새로운 항암제 개발에 일차적인 자료를 제공하는 것을 그 목적으로 한다. 방법 : 가래나무 뿌리의 methanol 추출물을 hexane, chloroform, ethyl acetate. n-buthanol, water로 분획하고 세포독성을 측정하였으며, 이들중 ethyl acetate 분획으로부터 세포독성을 나타내는 물질들을 분리하였으며 현재 이들의 구조를 분광분석학적인 방법으로 결정하고 있다. 결과 : 현재까지 분리된 물질들은 약한 세포독성을 나타내고있으며, 그들 중 한물질의 구조를 결정하였다.

• Applied Biological Chemistry
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• v.48 no.1
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• pp.1-15
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• 2005

Pathogens, insects and weeds have significantly reduced agricultural productivity. Thus, to increase the productivity, synthetic agricultural chemicals have been overused. However, these synthetic compounds that are different from natural products cannot be broken down easily in natural systems, causing the destruction of soil quality and agricultural environments and the gradually difficulty in continuous agriculture. Now agriculture is faced with the various problems of minimizing the damage in agricultural environments, securing the safety of human health, while simultaneously increasing agricultural productivity. Meanwhile, plants produce secondary metabolites to protect themselves from external invaders and to secure their region for survival. Plants infected with pathogens produce antibiotics phytoalexin; monocotyledonous plants produce flavonoids and diterpenoids phytoalexins, and dicotylodoneous plant, despite of infected pathogens, produce family-specific phytoalexin such as flavonoids in Leguminosae, indole derivatives in Cruciferae, sesquitepenoids in Solanaceae, coumarins in Umbelliferae, making the plant resistant to specific pathogen. Growth inhibitor or antifeedant substances to insects are terpenoids pyrethrin, azadirachtin, limonin, cedrelanoid, toosendanin and fraxinellone/dictamnine, and terpenoid-alkaloid mixed compounds sesquiterpene pyridine and norditerpenoids, and azepine-, amide-, loline-, stemofoline-, pyrrolizidine-alkaloids and so on. Also plants produces the substances to inhibit other plant growths to secure the regions for plant itself, which is including terpenoids essential oil and sesquiterpene lactone, and additionally, benzoxazinoids, glucosinolate, quassinoid, cyanogenic glycoside, saponin, sorgolennone, juglone and lots of other different of secondary metabolites. Hence, phytoalexin, an antibiotic compound produced by plants infected with pathogens, can be employed for pathogen control. Terpenoids and alkaloids inhibiting insect growth can be utilized for insect control. Allelochemicals, a compound released from a certain plant to hinder the growth of other plants for their survival, can be also used directly as a herbicides for weed control as well. Therefore, the use of the natural secondary metabolites for pest control might be one of the alternatives for environmentally friendly agriculture. However, the natural substances are destroyed easily causing low the pest-control efficacy, and also there is the limitation to producing the substances using plant cell. In the future, effects should be made to try to find the secondary metabolites with good pest-control effect and no harmful to human health. Also the biosynthetic pathways of secondary metabolites have to be elucidated continuously, and the metabolic engineering should be applied to improve transgenics having the resistance to specific pest.