• Title/Summary/Keyword: coumarin group

Search Result 36, Processing Time 0.029 seconds

C-H···π and C-H···O Interactions in Coumarin 6 : 3-(2-benzothiazolyl)-7-(diethylamino)-coumarin

  • Li, Xiaochuan;Son, Young-A
    • Textile Coloration and Finishing
    • /
    • v.22 no.2
    • /
    • pp.83-87
    • /
    • 2010
  • Crystal structure of coumarin 6 has been solved by X-ray diffraction. The crystals are triclinic, space group P-1, with a=8.823(2) ${\AA}$, b=8.898(2) ${\AA}$, c=11.025(9) ${\AA}$, ${\alpha}$=86.41(3)$^{\circ}$, ${\beta}$=85.39(3)$^{\circ}$, ${\gamma}$=76.23(3)$^{\circ}$, Mr=350.42, V=837.1(3) ${\AA}^3$, Z=2 and R=0.0516. The molecules are packed parallel to each other by weaker ${\pi}{\cdots}{\pi}$ and C-H${\cdots}{\pi}$ interactions. The detailed geometry of C-H${\cdots}{\pi}$ interactions were discussed. The hydrogen bonds and non-traditional C-H${\cdots}O$ interactions join the no-parallel molecules together. All the molecules packed wall-like with the molecular brick.

The Compositional Differences of Sipjeondaebo-tang(Siquandabu-tang) Decoctions Extracted by Different Extraction Method and Extraction Time (전탕 방법 및 전탕 시간에 따른 십전대보탕 전탕액 비교 연구)

  • Kim, Jung-Hoon;Seo, Chang-Seob;Jeon, Woo-Young;Shin, Hyeun-Kyoo
    • The Journal of Korean Obstetrics and Gynecology
    • /
    • v.25 no.2
    • /
    • pp.108-119
    • /
    • 2012
  • Objectives: This study was performed to compare the differences between decoctions extracted by different extraction method and extraction time. Methods: Decoctions were prepared with pressurized or non-pressurized extraction for 60, 120 and 180min. The yield of extract, total soluble solid content, hydrogen ion concentration(pH) and the content of reference compound in Sipjeondaebo-tang (Siquandabu-tang) were investigated. Results: While yields and the total soluble solid of decoction were higher in pressurized method proportional to extraction time, pH values were lower in pressurized method and showed decreasing values with increasing extraction time. Albilflorin, ferulic acid, nodakenin, coumarin, cinnamaldehyde and glycyrrhizin were contained in decoctions by pressurized extraction method more than non-pressurized method whereas the content of coumarin was higher in decoctions by non-pressurized extraction method. In addition, coumarin was extracted increasingly with extraction time in decoctions by pressurized method, however, nine compounds except cinnamaldehyde showed the tendency of increasing proportional to extraction time. Conclusions: The results show that extraction methods including pressurized or non-pressurized extraction, and extraction time could affect the physicochemical characteristic or composition of Sipjeondaebo-tang(Siquandabu-tang) decoction.

Apoptosis in Leukemic Cells Induced by Anti-Proliferative Coumarin Isolated from the Stem Bark of Fraxinus rhynchophylla

  • Lee, Beom Zoo;Lee, Ik Soo;Pham, Chau Ha;Jeong, Soon-Kyu;Lee, Sulhae;Hong, KwangWon;Yoo, Hee Min
    • Journal of Microbiology and Biotechnology
    • /
    • v.30 no.8
    • /
    • pp.1214-1221
    • /
    • 2020
  • Esculetin 6-O-β-D-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside (EAG) is a coumarin glycoside isolated from the stem bark of Fraxinus rhynchophylla. This study scrutinized the anti-proliferative activity of EAG on blood cancer-derived Jurkat leukemic cells. Cell viability assays in leukemic cancer cells determined that EAG possesses potent anti-proliferative effects. Moreover, treatment with EAG increased the proportion of apoptotic cells, resulted in cell cycle arrest being induced at the subG0/G1 phase, and reduced the proportion of cells present in the S phase. In addition, mitochondrial membrane potential was reduced by EAG in Jurkat cells. Additionally, EAG triggered apoptosis that was mediated by the downregulation of BCL-XL, p-IκBα, and p-p65 expressions in addition to the upregulation of cleaved Caspase 3 and BAX expressions. These findings revealed that the toxic effect of EAG was mediated by intracellular signal transduction pathways that involved a mechanism in which reactive oxygen species (ROS) were upregulated. Thus, this study concludes that EAG could potentially serve as a therapeutic agent for leukemia.

Biological Activity of Natural Coumarins (천연(天然)쿠마린의 생리활성(生理活性))

  • Shin, Kuk-Hyun;Chi, Hyung-Joon
    • Korean Journal of Pharmacognosy
    • /
    • v.10 no.1
    • /
    • pp.1-8
    • /
    • 1979
  • The naturally occurring coumarins are likely to be a large and important group of plant products which are not only metabolic products of the living cells but possess varied physiological and pharmacological actions. Investigations concerning various biological activities of natural coumarins have been undertaken by many investigators in continuing effort. The authors describe on experimental results of biological activities of coumarin derivatives with particular emphasis on 10 different activities that are considered to be of importance in view of the development of new drugs from natural resources.

  • PDF

Antioxidative and Macrophage Phagocytic Activities and Functional Component Analyses of Selected Korean Chestnut (Castanea crenata S. et Z.) Cultivars (국내산 밤 일부 품종의 기능성 성분분석과 항산화 및 대식세포 활성)

  • Lee, Hyeon-Ju;Chung, Mi-Ja;Cho, Jae-Youl;Ham, Seung-Shi;Choe, Myeon
    • Journal of the Korean Society of Food Science and Nutrition
    • /
    • v.37 no.9
    • /
    • pp.1095-1100
    • /
    • 2008
  • Antioxidative and macrophage phagocytic activities and contents of functional component in selected Korean chestnuts (Dantaek, Daebo, Okkwang, Seokchu, Byunggo) were evaluated. Coumarin, gallic acid and catechin in inner skin and whole kernel of selected Korean chestnuts were detected by HPLC. The predominant functional components in inner skin of chestnut were catechin, followed by gallic acid and coumarin. However, the whole kernel had only gallic acid. Thus, the antioxidant properties of gallic acid and catechin were evaluated through DPPH radical-scavenging activity and SOD like activity. Gallic acid and catechin at 6.0 mg/100 g exhibited 69.4% and 38.3% of scavenging activities on DPPH radical, respectively. DPPH radical-scavenging activity of gallic acid increased in a concentration-dependent manner. Gallic acid was found to possess higher DPPH radical-scavenging activity than equivalent amount of catechin at all concentrations, whereas catechin was found to have higher SOD like activity than gallic acid. In addition, pre-incubation of macrophage with white kernel extract from Byunggo resulted in a significant increase of phagocytic activity and yellow kernel extracts from Byunggo, Dantaek, Daebo and Okkwang, leading to an increase in phagocytic activity compared with untreated cells. Yellow kernel extracts was found to have higher phagocytic activity than white kernel extracts. Byunggo had the highest phagocytic activity. The results suggest that the Korean chestnut may provide a natural source of antioxidants and active immunity.

The Effect of Scoparone on the Hepatic Bromobenzene Metabolizing Enzyme System in Rats (간의 Bromobenzene 대사계에 미치는 Scoparone의 효과(I))

  • Kim, Eun-Ju;Lee, Chung-Kyu;Choi, Jong-Won
    • Korean Journal of Pharmacognosy
    • /
    • v.23 no.2
    • /
    • pp.81-88
    • /
    • 1992
  • The effects of scoparone, one of coumarin derivative on the hepatic bromobenzene metabolizing enzyme system was estimated in rats. Scoparone pretreatment revealed dose-dependently the recovery of decrease in epoxide hydrolase activity due to the bromobenzene(310 mg/kg, i.p.) treatment. And also scoparone and scopoletin (each 5mg/kg, p.o.) pretreatments showed two times increase in the $V_{max}$ values compared to those of bromobenzene-treated group which were calculated from tripartite reciprocal plots. The mode of protective effect of scoparone against bromobenzene induced toxicity is considered to be due to the induction of microsomal enzyme activity by scopoletin, the intermediate metabolite of scoparone. The changes in cytochrome P-450 activity, aminopyrine N-demethylation, aniline hydroxylation and glutathione S-transferation in scoparone-treated group were not significantly different from those of the control group.

  • PDF

Crystal and Molecular Structure of Methyl 12-(3-bromophenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carboxylate

  • Kothandan, Gugan;Ganapathy, Jagadeesan;Damodharan, Kannan;Sanmargam, Aravindhan
    • Journal of Integrative Natural Science
    • /
    • v.7 no.2
    • /
    • pp.92-102
    • /
    • 2014
  • The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a = 28.633(3) ${\AA}$, b= 9.3215(7) ${\AA}$ and c= 24.590(2) ${\AA}$ [alpha & gamma=$90^{\circ}$ beta= $115.976(3)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [119.74 $(2)^{\circ}$] and N1-S1-C5 [$105.57(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($316.2(1)^{\circ}$) indicates that N1 is in sp2 hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. The carboxylate group of atoms were disordered over two positions with site occupancy factors 0.598 (9):0.402 (9). Crystal structure and packing is stabilized by $C-H{\ldots}O$ intra and inter molecular hydrogen bond interactions.

Antithrombotic Effect of the BuOH Soluble Fraction of Angelica dahurica Root (백지 BuOH 가용분획의 항혈전 활성에 관한 연구)

  • Kim, Chang-Min;Kwon, Yong-Soo;YunChoi, Hye-Sook
    • Korean Journal of Pharmacognosy
    • /
    • v.26 no.1
    • /
    • pp.74-77
    • /
    • 1995
  • Several coumarins isolated from Angelica sp. were described to show inhibitory effects against human platelet aggregation. The anti-thrombotic and anti-platelet potential was evaluated, in this paper, with the BuOH soluble fraction of Angelica dahurica root. The BuOH fraction was divided into five subfractions fr. A - E and tested in the mouse model of thrombosis. Survival was enhanced to 35% with fr. A or fr. E treated (500 mg/Kg, p.o.) group of mice compared with 5% survival of the control group. However, none of the 8 coumarin glycosides obtained from fr. A, at the conc. of 0.5 mg/ml, showed inhibitory effects against rat platelet aggregation induced by ADP or collagen.

  • PDF

Crystal and Molecular Structure of 12-(2-Methoxyphenyl)-9-[(4-methylbenzene)sulfonyl]-22-oxo-13,21-dioxa-9-azapentacyclo [12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-heptaene-11-carbonitrile

  • Ganapathy, Jagadeesan;Damodharan, Kannan;Manickam, Bakthadoss;Sanmargam, Aravindhan
    • Journal of Integrative Natural Science
    • /
    • v.7 no.3
    • /
    • pp.149-158
    • /
    • 2014
  • The crystal structure of the title compounds with both coumarin and sulfonamide moieties were examined. These two groups have very special for their pharmaceutical and medicinal properties have been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=$8.5775(4){{\AA}$, b=$24.9943(13){\AA}$ and c=$13.7319(7){\AA}$ [alpha & gamma=$90^{\circ}$ beta=$103.558(2)^{\circ}$]. In the structure The S1 atom shows a distorted tetrahedral geometry, with O1-S1-O2 [$121.08(1)^{\circ}$] and N1-S1-C5 [$105.85(1)^{\circ}$] angles deviating from ideal tetrahedral values are attributed to the Thrope-Ingold effect. The sum of bond angles around N1 ($354.9^{\circ}$) indicates that N1 is in $sp^2$ hybridization. The Pyridine ring adopts boat conformation and pyran rings adopt a sofa conformation. Crystal structure is stabilized by C-H...O intra molecular hydrogen bond interactions.