• Title/Summary/Keyword: $C_8$-methoxy

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Examination of Berberine Dye using GC-MS after Selective Degradation Treatments (GC-MS를 이용한 Berberine 염료의 퇴화 거동 연구)

  • Ahn, Cheun-Soon
    • Journal of the Korean Society of Clothing and Textiles
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    • v.33 no.12
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    • pp.2002-2010
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    • 2009
  • The degradation behavior of berberine is examined using GC-MS to select the fingerprint products that can be used to identify berberine dye in badly faded archaeological textiles. A total of $100^{\circ}C$ thermal and $H_2O_2/UV/O_2$ degradation systems were used to degrade berberine chloride 0.1% solution up to 408 hours. The samples were analyzed using the GC-MS. Dihydroberberine, 2-pteridinamine, 6,7-dimethyl-N-[(trimethylsilyl) oxy]-, and 8-methoxy-11-[3-methylbutyl]-11H-indolo[3,2-c]-quinoline, 5-oxide were detected as the major products of thermal degradation and identified as the fingerprint products for berberine dye at the early stage of degradation. Isobenzofuran-1,3-dione,4,5-dimethoxy-, 9H-fluorene,3,6-bis(2-hydroxyethyl)-,1,3-dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro-, and 3-tert-butyl-4-hydroxyanisole were detected as the major products generated by the $H_2O_2/UV/O_2$ degradation and identified as the fingerprint products for berberine dye under severe degradation conditions.

Synthesis and Biological Activities of New 5-Substituted Uracil Derivatives (새로운 5-치환 Uracil 유도체의 합성 및 생물활성)

  • Yi, Won-Hui;Park, Jung-Sup;Won, Jeong-Hee;Lee, Chong-Ock;Ryu, Eung-K.
    • YAKHAK HOEJI
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    • v.35 no.6
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    • pp.497-503
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    • 1991
  • Six novel 5-substituted-1-[2-(3-methoxy-2-hydroxyphenyl)-1-methoxyethyl]uracils 2a-f were prepared by condensation of 2,4-bis(trimethylsilyloxy)-5-substituted uracils with 2,7-dimethoxy-2,3-dihydrobenzofuran (9) in the presence of Lewis acid. The 2,3-dihydrobenzofuran derivative 9 was obtained by intramolecular acetalization of 2-acetoxy-3-methoxyphenyl acetaldehyde (8) which was synthesized by oxidative cleavage of 1-allyl-2-acetoxy-3-methoxybenzene (7) using osmium tetroxide followed by $NaIO_4$. Compounds 2a-f were evaluated for in vitro antiviral activity against HSV-1, HSV-2 and HRV. None of these compounds showed activity with $ID_{50}$ values up to $100\;{\mu}g/ml$ except for 5-chlorouracil derivative 2d which exhibited antiviral activity against HSV-1 with $ED_{50}$ $30\;{\mu}g/ml$. In the antitumor activity against L1210 and P388 leukemia cell lines, 2d showed activity with $ID_{50}$ values of $14\;{\mu}g/ml$ and $11.6\;{\mu}g/ml$, and 2c with $ID_{50}$ values of $22.9\;{\mu}g/ml$ and $8.8\;{\mu}g/ml$, respectively.

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Silene Intermediates. The Reaction of Chlorodiphenylvinylsilane with tert-Butyllithium

  • Lee, Myoung-Euy;Lee, Jin-Kyu;Kim, Chang-Hwan
    • Bulletin of the Korean Chemical Society
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    • v.8 no.5
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    • pp.355-358
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    • 1987
  • The reaction of t-butylithium with chlorodiphenylvinylsilane at low temperatures in hexane gave a 52% yield of the two isomeric 1,1,3,4-tetraphenyl-2,4-dineopenty-1,3-disilacyclo butanes mixture, formed by a head-to-tail dimerization of 1,1-diphenyl-2-neopentylsilene intermediate. In the presence of the trapping agents such as trimethylmethoxysilane and anthracene, the expected trapped adducts, 1-methoxy-l,l-diphenyl-2-trimethylsilyl-4,4-dimethyl-1-silapentane and 2,2-diphenyl-3-neopentyl-(5,6 : 7,8)-dibenzo-2-silabicyclo-(2.2.2)-octane, were obtained in 74% and 46% yields, respectively. These products were separated and their stereochemistry were assigned on the basis of $^1H$- and $^{13}C$-NMR data.

Antimutagenic Effects and Compounds Identified from Hexane Fraction of Persimmon Leaves (감잎 핵산획분의 항돌연변이 효과와 항돌연변이 물질의 GC-MS를 이용한 동정)

  • Moon, Suk-Hee;Kim, Jeong-Ok;Rhee, Sook-Hee;Park, Kun-Young;Kim, Kwang-Hyuk;Rhew, Tae-Hyong
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.22 no.3
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    • pp.307-312
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    • 1993
  • Methanol extract of dried persimmon leaves was fractionated to hexane, chloroform, ethyl acetate, butanol, and aqueous tractions. Hexane, butanol, and aqueous fractions had high yields of extracts. Hexane fraction among these fractions showed the highest inhibition rate on the mutagenicities of aflatoxin (AFB$_1$), dimethyl-amino-bi-phenyl (DMAB), N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), and 4-nitroquinoline-1-oxide (4-NQO) in Salmonella typhimurium TA100. Hexane fraction was further fractionated into eight fractions by silica gel column c-hromatography and thin layer chromatography (TLC). The fraction 5 on TLC exhibited the highest antimutagenic activity on AFB$_1$, DMAB, and MNNC. 1'-oxocannabinol, 3B-acetoxy-17-methyl-5a-18 (13-17) abeoardrost-13-one, 4-methoxy-2'6'-dinitro-3, 5-di-t-butylbiphenyl, 8, 9-dihydro-5, 6-dimethoxy-dibenz [c, h]isoquino [2, 1, 8-1 ma]carbazole-11, 16-dione were tentatively identified from this antimutagenic fraction by GC-MS.

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Growth Characteristics and Ingredient Analysis According to the Transplanting Date and Distance of Dendranthema (L.). (감국 정식시기와 거리에 따른 생육특성과 성분 분석)

  • Jung, J.H.;Park, N.B.
    • Journal of Practical Agriculture & Fisheries Research
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    • v.22 no.1
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    • pp.65-77
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    • 2020
  • In order to industrialize of Dendranthema indicum (L.) DesMoul., which is a lot of commercially available and is synonymous with chrysanthemum tea, in the autumn of 2018, Dendranthema indicum (L.) DesMoul. seeds were collected from its own native region, and the seeds were germinated after refrigerated storage. Young seedlings were subjected to experiments in February, March, and April in the open field to examine the effects on the harvesting of leaves by distance and the growth of leaves and stems. The results of analyzing the components by collecting the leaves+stem after collecting the flower of Dendranthema indicum (L.) DesMoul. are as follows. 1. When D. indicum (L.) DesMoul. seedlings were planted according to the transplanting date, the number of flowers was 17.1 in the transplanting date in April. The diameter of the flower was 2.9cm, 16ea, 6.5~6.6g in the fresh weight, and the dry weight of the case was 1.1~1.2g. The leaves were 46~47ea in March and April in the planted area, 5.2~5.3cm in leaf length and 3.5~3.6cm in leaf width. 2. When planted D. indicum (L.) DesMoul. seedlings according to transplanting distance, the number of flowers was 16.2 when planted at 20×20cm intervals and, 16.8~17.1 at 30×30~50×50cm intervals. The diameter of the flower was 2.7~2.8cm, the number of petals was 8, the length of the petal was 0.8 cm, and fresh weight was 6.5~6.6g per flower. Leaves had the largest number of 47 of 30×30cm and 40×40cm, and leaf length appeared at the longest 6.2cm in the 50×50cm treatment area, but 5.2cm in the other treatment areas. 3. The extraction yield of D. indicum (L.) DesMoul. leaves+stems was 7.93%, and the extraction solvent colors were light green at 50, 60% and green at 70, 80, 90, 100%. The extraction yield of D. indicum (L.) DesMoul. flowers was 7.58%, the color of the extraction solvent was light yellow at 50, 60 and 70%, yellow at 80 and 90%, and dark yellow at 100%. 4. We confirmed 11 kinds of ingredients such as in D. indicum (L.) DesMoul. flowers are gallic acid, 4-hydroxy benzoic acid, methyl gallate, 4-hydroxy-3-methoxy benzoic, caffeic acid, salicylic acid, p-coumaric acid, sinapic acid, naringin, 4-melthoxyben, flavone. The content was 29.200-36.900ppm. 5. The components contained in the D. indicum (L.) DesMoul. leaf+stem, salicylic acid appeared at 6,129.526ppm, and the next 4-methoxyben was 1,966.714ppm. It was methyl gallate 8.197ppm, 4-hydroxy-3-methoxy benzoic 6.994ppm, caffeic acid 5.566ppm, flavone 4.522ppm, p-coumaric acid 3.787ppm, gallic acid 1.893ppm that appeared in the content below 10ppm.

Compounds from the Seeds of Myristica fragrans and Their Cytotoxic Activity

  • Cuong, To Dao;Lim, Chae-Jin;Trang, Tran Thi Thu;Bae, Yoon-Ho;Thu, Nguyen Van;Tung, Nguyen The;Hung, Tran Manh;Woo, Mi-Hee;Choi, Jae-Sue;Min, Byung-Sun
    • Natural Product Sciences
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    • v.18 no.2
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    • pp.97-101
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    • 2012
  • Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7'-(3',4'-methylenedioxyphenyl)-8,8'-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

The Behavior of the Formation of (111) Twins in $BaTiO_3$ Synthesized by Sol-Gel Route (졸-겔법으로 제조한 $BaTiO_3$에서(111)쌍정의 생성거동)

  • Yoo, Young-Sung;Kim, Young-Jung;Kim, Hwan
    • Korean Journal of Materials Research
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    • v.6 no.2
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    • pp.175-181
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    • 1996
  • Ti(i-OC3H7)와 Ba(OH)2.8H2Or 그리고 공통용매로서 2-Methoxy Ethanol을 이용하여 균일 용액을 제조하고, 이로부터 미세하고 조성비가 균일한 BaTiO3분말을 제조하였다. 이러한 졸-겔법으로 제조된 분말을 TG-DTA와 XRD 분석으로 결정화 및 상변화를 관찰하였다. 각 온도별로 하소된 분말에서 (111)쌍정의 생성여부를 TEM을 이용해 관찰한 결과, 합성된 BaTiO3 분말에서는 하소중(111)쌍정의 생성이 활발히 일어나지 않는 것으로 판단되었다. 특히(111) 쌍정판은 합성된 겔을 120$0^{\circ}C$에서 하소한 후 이를 140$0^{\circ}C$에서 소결한 경우에만 관찰할 수 있었다. 이러한 하소온도의 영향은 원료분말의 입자크기나 형상이 쌍정 생성에 큰 영향을 미침을 의미하는 것으로, 본 연구에서는 이를 근거하여 (111) 쌍정의 생성에 대해서 고찰하였다.

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The Crystal Structure of Metoclopramide

  • Shin, Whan-chul;Chang, Tai-Sik;Koo, Chung-Hoe
    • Bulletin of the Korean Chemical Society
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    • v.4 no.3
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    • pp.123-127
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    • 1983
  • The crystal structure of metoclopramide, $C_14H_22ClN_3O_2$, has been determined by X-ray diffraction techniques using diffractometer data obtained by the ${\omega}-2{\theta}$ scan technique with Mo $K\alpha$ radiation from a crystal with space group symmetry $P{\overline{1}}$ and unit cell parameters a = 7.500(1), b = 8.707(2), c = 13.292(2) ${\AA}$; ${\alpha}$ = 101.70(2), ${\beta}$ = 81.20(2), and ${\gamma}$ = $114.90(l)^{\circ}$. The sructure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.055 for the 1524 observed reflections. The bent overall-conformation of the molecule seems to be determined mainly by the bifurcated intramolecular hydrogen bond from the amide nitrogen atom to the methoxy oxygen and the amine nitrogen atoms. The crystal packing consists of the hydrogen bonds, ${\pi}-{\pi}$ interaction and hydrophobic interaction.

2-(Trimethylammonium) Ethyl (R)-3-Methoxy-3-oxo-2-Stearamidopropyl Phosphate Suppresses Osteoclast Maturation and Bone Resorption by Targeting Macrophage-Colony Stimulating Factor Signaling

  • Park, So Jeong;Park, Doo Ri;Bhattarai, Deepak;Lee, Kyeong;Kim, Jaesang;Bae, Yun Soo;Lee, Soo Young
    • Molecules and Cells
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    • v.37 no.8
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    • pp.628-635
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    • 2014
  • 2-(Trimethylammonium) ethyl (R)-3-methoxy-3-oxo-2-stearamidopropyl phosphate [(R)-TEMOSPho], a derivative of an organic chemical identified from a natural product library, promotes highly efficient megakaryopoiesis. Here, we show that (R)-TEMOSPho blocks osteoclast maturation from progenitor cells of hematopoietic origin, as well as blocking the resorptive function of mature osteoclasts. The inhibitory effect of (R)-TEMOSPho on osteoclasts was due to a disruption of the actin cytoskeleton, resulting from impaired downstream signaling of c-Fms, a receptor for macrophage-colony stimulating factor linked to c-Cbl, phosphoinositol-3-kinase (PI3K), Vav3, and Rac1. In addition, (R)-TEMOSPho blocked inflammation-induced bone destruction by reducing the numbers of osteoclasts produced in mice. Thus, (R)-TEMOSPho may represent a promising new class of antiresorptive drugs for the treatment of bone loss associated with increased osteoclast maturation and activity.

Structural Analysis and Biological Activities of Sesquiterpene Lactones Isolated from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 분리한 Sesquiterpene Lactone들의 구조규명 및 생리활성)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1285-1295
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    • 2017
  • Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.