• Title/Summary/Keyword: ${\beta}$-Sitosterol

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Lipoxygenase Inhibitory Constituents from Indigofera oblongifolia

  • Sharif, Ahsan;Ahmed, Ejaz;Malik, Abdul;Riaz, Naheed;Afza, Nighat;Nawaz, Sarfraz Ahmad;Arshad, Muhammad;Shah, Muhammad Raza;Chaudhary, Muhammad Iqbal
    • Archives of Pharmacal Research
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    • v.28 no.7
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    • pp.761-764
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    • 2005
  • Indigin, alkylated xanthene (1) and indigoferic acid (2) have been isolated from the chloroform soluble fraction of Indigofera oblongifolia, along with $\beta$-sitosterol (3) and 3-hydroxybenzoic acid (4), which are reported for the first time from this species. Their structures were determined through spectroscopic techniques. Both the new compounds 1 and 2 showed significant activity against enzyme lipoxygenase, while 2 further showed moderate inhibition against BChE.

The Chemical Constituents of the Stem Barks of Fraxinus rhynchophylla (물푸레나무(Fraxinus rhynchophylla) 수피의 추출성분)

  • Yang, Eun-Ju;Lee, Dong-Geun;Lee, Jong-Won;Kim, Yae-Sil;Lim, Sun-Ha;Song, Kyung-Sik
    • Applied Biological Chemistry
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    • v.50 no.4
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    • pp.348-351
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    • 2007
  • The stem barks of Fraxinus rhynchophylla was extracted with 95% EtOH, and the concentrated extract was successively partitioned with $CH_2Cl_2$, n-BuOH, and $H_2O$ in order to investigate the major phytochemicals. From the $CH_2Cl_2$ soluble fraction, a sterol (1) was isolated through the repeated silica gel column chromatographies. Three additional compounds (2-4) were isolated from the n-BuOH soluble fraction through silica gel, RP-18, and Sephadex LH-20 column chromatographies. Their chemical structures were elucidated as daucosterol $(1;{\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside)$, caffeic acid (2), 6,8-dihydroxy-7-methoxycoumarin (3), and coniferaldehyde glucoside (4) by comparing their spectral data with those in the literatures. All isolates (1-4) were the first to be isolated from F. rhynchophylla.

Chemical Constituents of Saposhnikovia divaricata (방풍의 화학 성분)

  • Kim, So-Jun;Chin, Young-Won;Yoon, Kee-Dong;Ryu, Min-Youl;Yang, Min-Hye;Lee, Je-Hyun;Kim, Jin-Woong
    • Korean Journal of Pharmacognosy
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    • v.39 no.4
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    • pp.357-364
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    • 2008
  • The roots of Saposhnikovia divaricata Schischk. (Umbelliferae) have been known to possess analgesic, anti-inflammatory, anti-parasitic and anti-bacterial activities, and used for curing headaches, fever and arthralgia. In this study, we aimed to isolate active constituents to provide phytochemical data for the quality control of this plant. Nine coumarins, eight chromones, three sterols and a coumarolignan were isolated from EtOAc-soluble fraction of the roots of S. divaricata through repetive column chromatography method using silica gel, ODS gel, Sephadex-LH 20, MPLC and HPLC. By analyses of spectroscopic data and comparison of their data with those of published values, the compounds were identified as 3'-O-angeloylhamaudol (1), ${\beta}$-sitosterol (2), marmesin (3), phellopterin (4), anomalin (5), imperatorin (6), xanthotoxin (7), deltoin (8), bergapten (9), stigmasterol (10), ledebouriellol (11), hamaudol (12), 8'-epicleomiscosin A (13), xanthoarnol (14), cimifugin (15), 5-O-methylvisamminol (16), daucosterol (17), 4'-O-${\beta}$-D-glucosyl-5-O-methylvisamminol (18), nodakenin (19), sec-O-glucosylhamaudol (20), prim-O-glucosylcimifugin (21). Among them, 8'-epicleomiscosin (13) was firstly reported from Umbelliferae family and xanthoarnol (14) and nodakenin (19) were isolated from this plant for the first time.

Cytotoxic and Antioxidant Compounds Isolated from the Cork of Euonymus alatus Sieb.

  • Jeong, Su Yang;Zhao, Bing Tian;Kim, Young Ho;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
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    • v.19 no.4
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    • pp.366-371
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    • 2013
  • Seventeen compounds (1 - 17), ${\beta}$-sitosterone (1), lupenone (2), arborinone (3), ${\beta}$-sitosterol (4), lupeol (5), epi-lupeol (6), taraxerol (7), betulinic acid (8), 24R-methyllophenol (9), germanicol (10), hexatriacontane (11), nonacosan-1-ol (12), benzoic acid (13), tetradecyl(E)-ferulate (14), di(2-ethylhexyl) phthalate (15), trilinolein (16) and monopalmitin (17), were isolated from the methylene chloride-soluble fraction of the cork of Euonymus alatus Sieb. The structures of these compounds were elucidated on the basis of spectroscopic evidence. Compounds 6, 11, 13 and 14 were isolated for the first time from this plant. Compound 4 showed moderate cytotoxic activity with an $IC_{50}$ value of 6.22 ${\mu}M$ in HL-60 cell line. Compound 9 exhibited moderate cytotoxic activity with $IC_{50}$ values of 63.31, 15.45, 15.14 and 21.72 ${\mu}M$ in four kinds of human cancer cell lines, Jurkat T, HeLa, HL-60 and MCF-7, respectively. Compound 17 showed moderate cytotoxic activity with an $IC_{50}$ value of 70.71 ${\mu}M$ in Jurkat T cell line. In addition, compounds 2, 3, 14 and 16 exhibited weak antioxidant activity with $IC_{50}$ values of 151.76, 170.79, 137.46 and 139.37 ${\mu}M$, respectively.

In Vitro Peroxynitrite Scavenging Activity of 6-Hydroxykynurenic Acid and Other Flavonoids from Gingko biloba Yellow Leaves

  • Hyun, Sook-Kyung;Jung, Hyun-Ah;Chung, Hae-Young;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1074-1079
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    • 2006
  • As part of our research on phytochemicals that exert protective effects against diseases related to reactive nitrogen species, we have evaluated the scavenging activity of the yellow leaves of Ginkgo biloba on $ONOO^{-}$. The methanol extract and ethyl acetate fraction obtained from yellow leaves of G. biloba evidenced a marked scavenging activity on authentic $ONOO^{-}$. Repeated column chromatography of the active ethyl acetate soluble fraction on silica gel, Sephadex LH-20, and RP-18, resulted in the purification of 15 known compounds, including sciadopitysin (1), ginkgolide B (2), bilobalide (3), isoginkgetin (4), kaempferol (5), luteolin (6), protocatechuic acid (7), bilobetin (8), amentoflavone (9), ${\beta}-sitosterol$ glucopyranoside (10), kaempferol 3-O-rhamnopyranoside (11), kaempferol 3-O-glucopyranoside (12), kaempferol $3-O-[{6^{'}-O-p-coumaroyl-{\beta}-D-glucopyranosyl(1{\rightarrow}2)-{\alpha}-L-rhamnopyranoside]$ (13), kaempferol 3-O-rutinoside (14), and 6-hydroxykynurenic acid (15). Among the compounds isolated, flavonoids (5, 6 and 11-14), protocatechuic acid (7), and 6-hydroxykynurenic acid (15) all exhibited marked scavenging activities on authentic $ONOO^{-}$. The $IC_{50}$ values of 5-7, 11-14 and 15 were as follows: $2.86{\pm}0.70,\;2.30{\pm}0.04,\;2.85{\pm}0.10,\;5.60{\pm}0.47,\;4.16{\pm}1.65,\;2.47{\pm}0.15,\;3.02{\pm}0.48,\;and\;6.24{\pm}0.27\;{\mu}M$, respectively. DL-Penicillamine ($IC_{50}=4.98{\pm}0.27\;{\mu}M$) was utilized as a positive control. However, the other compounds (1-4, 8-10) exerted no effects against $ONOO^{-}$.

Studies on the Chemical Constituents from the Seeds of Zizyphus jujuba var. inermis

  • Lee, Nam Kyung;Shin, Hyun Jung;Kim, Wan-Seok;In, Gyo;Han, Chang Kyun
    • Natural Product Sciences
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    • v.23 no.4
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    • pp.258-264
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    • 2017
  • This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ${\rho}$-menth-8-ene, and ${\gamma}$-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, ${\beta}$-sitosterol, stigmasterol, stigmasta-5,23-dien-$3{\beta}$-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-${\rho}$-coumaroyl-alphitolic acid, 3-O-trans-${\rho}$-coumaroyl-alphitolic acid, 2-O-cis-${\rho}$-coumaroyl-alphitolic acid, 2-O-trans-${\rho}$-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-${\rho}$-coumaroyl-maslinic acid, and 3-O-trans-${\rho}$-coumaroyl-maslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.

Isolation of Daucosterol and Naphthalene glucoside from Seeds of Cassia mimosoides var. nomame Makino (차풀 종자로부터 Daucosterol과 Naphthalene glucoside의 분리)

  • Park, Jun-Hong;Kwon, Sun-Jin
    • Korean Journal of Plant Resources
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    • v.22 no.1
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    • pp.26-30
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    • 2009
  • Daucosterol and naphthalene glycoside were isolated from the seeds of Cassia mimosoides var. nomame Makino. The isolated compounds were identified by spectral means including 1D, 2D-NMR and FAB-MS experiments. Daucosterol was characterized as ${\beta}$-sitosterol-3-O-${\beta}$-D-glucoside and naphthalene glucoside was done as 2-acetyl-3-methyl-6-methoxynaphthalene-1,8-diol 8-O-glucosyl-(1${\rightarrow}$6)-glucoside. These compounds were isolated for the first time from Cassia mimosoides var. nomame Makino.

Study on the Synthesis of N,N'-Dicyclohexylcarbodiimide from N,N'-Dicyclohexylurea (디사이클로헥실우레아로부터 디사이클로헥실카르보디이미드의 합성에 관한 연구)

  • Kim, Jae Young;Chung, Dae-Won
    • Applied Chemistry for Engineering
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    • v.22 no.3
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    • pp.319-322
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    • 2011
  • N,N'-Dicyclohexylcarbodiimide (DCC) known as powerful dehydrating reagent in amide or ester synthesis is converted into N,N'-dicyclohexylurea (DCU) during the reaction. In the paper, DCU was recovered from the reaction for the synthesis of the hydrophilic derivative of ${\beta}$-sitosterol, and the purification of the recovered DCU and the dehydration of DCU into DCC were investigated. In the presence of tosyl chloride, (TsCl) and triethylamine (TEA), DCU was converted into DCC, and the optimum molar ratio of [DCU] : [TsCl] : [TEA] was found to be 1.0 : 1.5 : 3.0. Pure DCC was obtained with a 46% yield by the sublimation after the purification process, and characterized by GC/MS, FT-IR and $^{13}C-NMR$.

The Origin of Molluscs Sterol (1) The Sterol Compositon of Bivalves and Snails (연체동물의 스테롤의 기원에 관하여 (1) 2매패와 권패의 스테롤 조성의 차이)

  • JOH Yong Goe;KIM Yong Keun
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.9 no.3
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    • pp.185-193
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    • 1976
  • The sterol compositions of the Pelecypoda, M. sultataria, S. sachalinensis, and the Gastropoda, H. discus hannai Inc, T. cornutus were investigated. The results areas follows: 1. The contents of the unsaponifiables and sterols of the Pelecypoda, M. sulcataria, S. sathalinensis, and the Gastropoda, H. discus hannai Ino, T. cornutus, are $12.0\%,\;11.8\%,\;and\;16.2\%,\;15.3\%$, respectively. 2. The complex sterols from the Pelecypoda and Gastropoda are well separated on Silica Gel HF 254 TLC impregnated with $15\%$ silver nitrate. 3. The prominent sterols of the Pelecypoda, M. sulcateria and S. sachalinensis, are 22-trans-24-norcholesta-5, $22-dien-3\beta-ol$ $3.0\%\;3.9\%$ 22-dehydrocholesterol $6.7\%,\;10.2\%$, cholesterol $39.0\%,\;48.6\%$ brassicasterol $14.1\%,\;13.8\%$ 24-methylenecholesterol $19.4\%,\;11.5\%$, stigmasterol $2.4\%,\;0\%$ $\beta-sitosterol\;10.5\%,\;11.9\%$, and fucosterol $4.3\%,\;0\%$. 4. Abalone, H. discus hannai Ino, and T. cornutus contain cholesterol $98.0\%,=97.5\% as main component with small amounts of 22-dehydrocholesterol, brassicasterol and desmosterol. In H. discus hannai rno, 24-methylenecholesterot and fucosterol are also found.

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Variation in Cartenoid Pigment and lipids of the Arkshell, (Anadara broughtonii) according to the Environmental Factors of the Growing Area (서식환경요인에 따른 피조개육의 Carotenoid색소와 지질성분의 변화)

  • Ha, Bong-Senk;Kang, Dong-Soo;Kim, Yung-Gwan;Kim, Kui-Shik
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.18 no.1
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    • pp.71-92
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    • 1989
  • The seasonal variations of environmental sea water, arid carotenoid and lipid composition of reddish muscle tissue of arkshell, Anadara broughtonii in Chungmu and $Y{\check{o}}su-area$ were investigated. In the sea water, pH value, salinity, electrical conductivity of Chungmu and $Y{\check{o}}su-area$ were similar tendency, but water temperature in annual average at Chungmu-area was about $2^{\circ}C$ higher than that of $Y{\check{o}}su-area$. The concentration of nitrite-nitrogen, ammonia-nitrogen, phosphate-phosphours at Chungmu-area were slightly higher than those at $Y{\check{o}}su-area$. Meanwhile the concentration of silicate-silicious at $Y{\check{o}}su-area$ was about 2 times higher than that of Chungmu-area. The bacterial density of the sea water was ranged from 3.6 to 93/100ml for coliform and 3.0 to 15/100ml for fecal colifrom at Chungmu-area, but the coliform was ranged 7.3 to 150/100ml and the fecal coliform was ranged 3.6 to 20/100ml at $Y{\check{o}}su-area$. Among the coliform, 8.9% Escherichia coli, 33.9% Citrobacter freundii, 41.1% Enterobacter aerogenes groups were classified and 16.1% was not identified. In the hemoglobin content of reddish muscle tissue of arkshell, one from Chungmu-area was ranged from 1.1 to 2.5 g /dl and one from $Y{\check{o}}su-area$ was ranged from 1.7 to 4.4 g /dl. In total carotenoid content, 0.80 to 1.28mg/100 g muscle was in Chungmu-area and 0.45 to 0.99mg/100 g muscle was in $Y{\check{o}}su-area$. Among the carotenoid compositions, pectenolone content was 63.0% in annual average from Chungmu area and 59.6% from $Y{\check{o}}su-area$, 6.5% from Chungmu area and 18.9% from $Y{\check{o}}su-area$ in ${\beta}-carotene$, 9.9% from Chungmu-area and 9.1% from Yosu-area in pectenoxanthin, 11.2% from Chungmu-area and 5.2% from $Y{\check{o}}su-area$ in diatoxanthin monoester were observed. In the seasonal variation for the major carotenoids, the content of pectenolone was continuously incresedbefore spawning period and showed the maximum in July, but decresed after spawning period. Diatoxanthin monoester was gradually incresed during all growing period from March to next January. And ${\beta}-carotene$ was decresed before spawning period and showed the maximum in July but incresed after spawning period. The major fatty acids of total lipid and fractionated lipid classes from total lipid namely neutral-, glyco- and phospholipid were $C_{16:0},\;C_{18:1},\;C_{22:6},\;C_{20:2},\;C_{18:2},\;C_{20:5}\;and\;C_{18:3}$ acid in the muscle tissue of arkshell. The content of neutral lipid showed about 2 times higher than polar lipid in the muscle tissue of arkshell from both Chungmu and, $Y{\check{o}}su-area$. The content of total and neutral lipid was decresed during spawning period. In the seasonal variation for fatty acid compositions, the content of polyenenoic acid in total and neutral lipid was decresed and saturated acid was incresed. On contrary, polyenoic acid in glyco and phospholipid was incresed and saturated acid was decresed during spawning period from July to September. The sterol composition in total lipid were mainly consisted of cholesterol, campesterol, brassicasterol and ${\beta}-sitosterol$. Especially, the rate of content in cholesterol showed decrese during spawning period butcampesterol showed increse from March to November.

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