• Title/Summary/Keyword: purpurin

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Synthesis and Photodynamic Activities of Pyrazolyl and Cyclopropyl Derivatives of Purpurin-18 Methyl Ester and Purpurin-18-N-butylimide

  • Yoon, Il;Park, Ho-Sung;Cui, Bing Cun;Kim, Jung-Hwa;Shim, Young-Key
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.169-174
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    • 2011
  • The synthesis of new pyrazolyl and cyclopropyl derivatives of purpurin-18 methyl ester and purpurin-18-N-butylimide 1a, 1b, 2a, 2b and 8 is described. The new compounds were characterized by NMR, UV-vis spectroscopy and mass spectrometry. UV-vis spectra of the new compounds showed long wavelength absorption of ranges 692 - 708 nm ($\lambda_{max}$). Photodynamic effects of the chlorin derivatives 1a, 1b, 2a and 2b were investigated by WST-1 assay in A549 cells, and showed good photodynamic activities with high photocytotoxicity and low cytotoxicity in the dark. In comparison between pyrazolyl and cyclopropyl derivatives, purpurin-18 methyl ester compounds 1a and 1b showed comparable photocytotoxicity result of the cell viabilities, otherwise, pyrazolyl derivative of purpurin-18-N-butylimide 2a showed better cell viabilities than those of cyclopropyl derivative 2b. And cyclopropyl derivative of purpurin-18-N-butylimide 2b showed higher dark cytotoxicity than that of others.

Efficient Synthesis and in vitro PDT Effect of Purpurin-18-N-Aminoimides

  • Cui, Bing Cun;Cha, Min-Uk;Li, Jia Zhu;Park, Ho-Sung;Yoon, Il;Shim, Young-Key
    • Bulletin of the Korean Chemical Society
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    • v.31 no.11
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    • pp.3313-3317
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    • 2010
  • A simple and efficient synthetic route for making purpurin-18-N-aminoimides is described. The purpurin-18-Naminoimides are obtained by treatment of purpurin-18 methyl ester with various amines. These new compounds have long wavelength absorptions in the range of 706 - 711 nm. In preliminary screening, the purpurin-18-N-aminoimides have shown promising photosensitizing activity for the cancer cell by in vitro study in photodynamic therapy.

Studies on the Production of Anthraquinone Derivatives by Tissue Culture of Rubia Species

  • Shin, Soon-Hee
    • Archives of Pharmacal Research
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    • v.12 no.2
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    • pp.99-102
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    • 1989
  • The tissue culture of Rubia cordifolia var. pratensis and R. akane were performed to enhance the biosynthesis of anthraquinone pigments under various conditions. The production of alizarin and purpurin in the callus was separately analysed and was quantitatively compared. The pigment biosynthesis was more active in the callus from R. cordifolia var. pratensis than from R. akane. The addition of ${\alpha}-ketoglutaric$ acid, a biosynthetic precursor of anthraquinones, enhanced the production of alizarin and purpurin remarkably.

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Comparison of TLC and GC-MS Method in the Analysis of Dye Extracted from Madder Plant (꼭두서니 추출염료에 대한 TLC와 GC-MS 분석법의 비교 연구)

  • ;S. Kay Obendorf
    • The Research Journal of the Costume Culture
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    • v.12 no.4
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    • pp.579-590
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    • 2004
  • This research was aimed to investigate and compare the effectiveness of TLC and GC-MS methods in the analysis of chromophoric substances extracted from madder plant. Alizarin and purpurin 0.3% solution were used as comparative standards; madder extraction was prepared by heating the solution of powdered madder at 80℃, pH 1.5, for 90 min. Best elution solvent for TLC in silica gel plate was toluene:ethyl acetate=9:1, which resulted in red and yellow spots from madder extraction each of which showed R/sub f/ values 0.32-0.43 and 0.07-0.11. Although the red spot in particular exhibited similar characteristics as standard purpurin in color, shape, and R/sub f/ values, the result was inconsistent throughout different TLC trials. GC-MS analysis showed only small amount of alizarin and no purpurin in the madder extraction. Other chromophoric substance such as 2-furancarboxaldehyde, 5-(hydroxymethyl)-, anthralin, and danthron were also detected in small amounts. The result indicated that TLC was less sensitive to detecting and identifying the natural dyestuff which is generally constituted with a number of similar but chemically different chromophoric substances.

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Dye Extraction and Silk Dyeing of Rubia Cordifolia Using Solvents (용제를 사용한 Rubia cordifolia의 색소 추출 및 Silk 염색)

  • Lim, Jee Young;Jang, Jeong Dae
    • Journal of the Korean Society of Clothing and Textiles
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    • v.37 no.4
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    • pp.506-513
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    • 2013
  • Rubia cordifolia L (Indian madder) contains red color purpurin (65-67%) and yellow color munjistin (10-12%) as well as nordamncanthal (9-10%). Purpurin is a traditional red dye. The purpose of this research is to increase the dyeability of silk and light fastness of dyed silk fabric. We dyed silk fabrics after pretreatment to remove the yellow component of madder using various solvents such as ethyl acetate, ethanol, methanol, chloroform, and acetone. The total K/S value was the highest in the case of chloroform and reflectance was the lowest at the red color region from 470nm to 530nm. Chloroform dissolved the yellow color of Rubia cordifolia; in addition, we found that the total K/S value increased and the ${\Delta}E$ value decreased by chloroform pretreatment for silk dyeing.

Effects of compounds related to signal transduction on anthraquinone biosynthesis in transformed cells of Rubia cordifolia var. pratensis (형질전환시킨 갈퀴꼭두서니 세포의 색소생합성에 미치는 수종의 신호전달 cascade 관련물질의 효과)

  • Lyu, Lee;Shin, Seung-Won
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.235-239
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    • 2000
  • The effects of several compounds related to signal transduction cascade were determined to induce the production of alizarin and purpurin in the hairy root culture system of Rubia cordifolia var. pratensis. It was found that out of five tested compounds jasmonic acid(1 mg/l) and methyl jasmonate(1 mg/l) stimulated strongly the biosynthesis of the pigments while linolenic acid(1 mg/l) induced no significant increase of the product. Yeast extract(600 mg/l) and arachidonic acid(1 mg/l) showed relatively mild inducing effects on production of alizarin. The effects of jasmonic acid and methyl jasmonate were reduced by treatment with cycloheximide(2.8 mg/l).

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The Study on the Dyeing Properties of Rubia akane Nakai (꼭두서니의 염색성에 관한 연구)

  • 주영주
    • Journal of the Korean Society of Clothing and Textiles
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    • v.26 no.9
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    • pp.1301-1307
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    • 2002
  • This paper surveys the mordanting and dyeing properties of Rubia akane Nakai appropriate extraction, dyeing and mordanting conditions of Rubia akane Nakai were determined, and the effect of mordanting method on dye uptake and color fastness of the dyed fabric was investigated. The optimum temperature to extract Rubia akane Nakai was during 1 hour in 8$0^{\circ}C$. The effective dyeing temperature and time of silk were 8$0^{\circ}C$, 1hour. The silk fabrics dyed with purpurin appeared red color, with alizarine appeared yellow-brown and with Rubia akane Nakai appeared yellow orange. K/S value of the dyeing fabrics was increased by pre-mordanting treatment. Mordant as Sn and Fe was better than anything else in K/S value. Mordanting treatment method affected color change of the dyed silk. In the case of Rubia akane Ntkai light fastness was increased by Fe and Al mordant treatment, Perspiration fastness of Rubia akane Nakai appeared more than 3 grades geneally. Fastness of abrasion and dry-cleaning appeared mon than 4~5 grades and these fastness improvement were generally effective for post-mordanting treatment.

Analysis of Dyes and Mordants of 16~17th Century Textiles Excavated from Daejeon (16~17세기 출토염직품의 염료와 매염제 분석)

  • Baek, Young-Mee;Kwon, Young-Suk;Goto-Doshida, Sumiko;Saito, Masako
    • Journal of Conservation Science
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    • v.28 no.2
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    • pp.119-129
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    • 2012
  • Excavated textiles provide very important research data on the costume culture of the Joseon dynasty. In particular, dyed textiles are indispensable for textile conservation research and for restoration of remains as well as for general costume culture research. Unfortunately, a prolonged burial environment causes the colors to change and gradually fade after excavation. Therefore, it is very difficult to identify the original color. In this study, natural dyed samples of red, yellow, purple and blue were prepared and analyzed using HPLC-PDA. Dyes of colorants extracted from excavated textile remains were analyzed by HPLC. In addition, mordants were analyzed using (SEM-EDX) in order to estimate the original color. The 16~17th Century's three samples were analyzed, sample 1, and 2 from Eunjin Song's Song Mun-Chang excavated at the Songchon-dong in Daejeon, and sample 3 from Yeosan Song's Song, Hee-Jong excavated at the Mokdal-dong in Daejeon. From the HPLC results, alizarin, purpurin, and indigo were detected on sample 1, alizarin and purpurin on sample 2, ellagic acid and indigo on sample 3. Therefore they were dyed with madder and indigo (sample 1), madder (sample2), pomagranted and indigo (sample 3). Al mordant was identified on three samples.

Production of Anthraquinone Derivatives by Hairy Roots of Rubia cordifolia var. pratensis (갈퀴꼭두선이의 Hairy Root 배양에 의한 Anthraquinone계 색소생산 연구(II))

  • Kim, You-Sun;Shin, Seung-Won
    • 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.

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Anthraquinones from Cell Suspension Culture of Morinda elliptica

  • Jasril, Jasril;Lajis, N.H.;Abdullah, M.A.;Ismail, N.H.;Ali, A.M.;Marziah, M.;Ariff, A.B.;Kitajima, M.;Takayama, H.;Aimi, N.
    • Natural Product Sciences
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    • v.6 no.1
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    • pp.40-43
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    • 2000
  • The chemical investigation on the cell suspension culture of Morinda elliptica L. yielded eight anthraquinones, two of which, anthragallol-1,2-dimethyl ether (3) and purpurin-1-methyl ether (4), have not been isolated from the original plant. Other compounds isolated include nordamnacanthal (1), alizarin-1-methyl ether (2), rubiadin (5), soranjidiol (6), $lucidin-{\omega}-methyl$ ether (7), and morindone (8). The structures of anthraquinones were established based on spectral studies.

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