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Dan Yuan, Yingni Pan, Yan Chen, Toshio Uno, Shaohui Zhang, Yoshihiro K ...
2008 Volume 56 Issue 1 Pages
1-6
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
JOURNAL
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Basic hydrolysis procedure is often included in the sample preparation in order to quantify malonylglucosides or acetylglucosides of soy materials. However, it is preferable not to use NaOH as a hydrolytic reagent considering the effect of its alkalinity on the successive injection to HPLC and low acidity of soy isoflavones. This paper presents an improved method for basic hydrolysis using ammonia as a hydrolytic reagent without the additional neutralization step. Moreover, by means of HPLC and LC-MS methods, a systematic quality evaluation of natural soy materials from Chinese markets were established and discussed, inclusive of soybeans, black soybeans, defatted soy flours, as well as the distribution of isoflavones in the seed coat, hypocotyl and cotyledon. The results indicate that HPLC profiling patterns of originating various isoflavone constituents of Chinese soybeans was similar to those of Japanese ones, and those of Chinese black soybeans was similar to those of American ones. The average content level of total soy isoflavones of Chinese soybeans and black soybeans were a little lower than that of American and Japanese ones. Additionally, the thorough analysis for Semen Sojae Praeparatum, a Chinese herbal medicine made from fermented black soybeans or soybeans was done for the first time and the characteristic of its HPLC profiling patterns shows the higher content of isoflavone glucosides and aglycones than those of natural soy materials.
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Noboru Sekiya, Atsushi Nishiwaki, Akio Nishiura, Masanobu Yamamoto, Ka ...
2008 Volume 56 Issue 1 Pages
7-11
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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We studied the effects of dextran, dextrin, and disintegrants on the chemical stability of Opalmon tablets containing Limaprost-alfadex (Limaprost/α-cyclodextrin complex) and found that the addition of dextran or dextrin significantly improved the chemical stability of Opalmon tablets under high humidity, compared to lactose. We also examined how dextran stabilizes Limaprost in Opalmon tablets and studied the formulation of Opalmon tablets in order to achieve higher chemical stability, rapid dissolution and reduced stickiness. The results suggested that dextran increases stabilization after moisture adsorption by decreasing the dissociation of Limaprost-alfadex to the free drug and α-cyclodextrin in the dextran matrix, when compared with the lactose matrix. The stickiness of Opalmon tablets containing dextran and dextrin was negligible when dextran and dextrin amounted to less than 20% of the formulation. By selecting a proper disintegrant, we obtained Opalmon tablets with higher chemical stability and rapid dissolution properties.
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Jiang-Ning Hu, Xue-Mei Zhu, Li-Kun Han, Masato Saito, Yin-Shi Sun, Mas ...
2008 Volume 56 Issue 1 Pages
12-16
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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To investigate the anti-obesity effects of escins extracted from the seeds of
Aesculus turbinata B
LUME, anti-obesity models
in vitro and
in vivo were employed. In a preliminary experiment, different solvent fractions of
Aesculus turbinata Bl
UME as well as two isolated compounds were tested for their effects on pancreatic lipase (PL)
in vitro. Subsequently, female ICR mice were fed a high fat diet with or without different concentrations of total escins for 11 weeks to examine body weight, parametrial adipose tissue weight, and hepatic triacylglycerol (TG) and total cholesterol (TC) contents. Plasma triacylglycerol levels (TG) after oral administration of lipid emulsions to rats were also investigated. The results showed that total escins (1 mg/ml) as well as two compounds isolated from total escins, namely escin Ib and IIa, showed inhibitory effects on PL activity.
In vivo, total escins suppressed the increase in body weight, parametrial adipose tissue weight, TG content, and TC content in mice's liver; TG content in rat plasma was also reduced at 1, 2 and 3 h after oral administration of the lipid emulsion plus different concentrations of escins compared to those in the lipid emulsion groups. Meanwhile, mice fed a high fat diet plus 2% total escins for 3 d had an increased TG level in the feces compared to the HF group. The reason for this may be due to a delay in the intestinal absorption of dietary fat by inhibiting PL activity.
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Mukhtar Ahmad Mukhtar Ahmad Bhat, Sayeed Ahmad, Junaid Aslam, Abdul Mu ...
2008 Volume 56 Issue 1 Pages
17-21
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Various
in vitro grown tissues (non-regenerative callus, regenerative callus and microshoot derived leaves) of
Solanum nigrum L. were cultured under salinity stress (0—150 m
M NaCl) for enhanced production of solasodine, a steroidal alkaloid and an alternative to diosgenin, which is used as a precursor for the commercial production of steroidal drugs. The role of plant growth regulators and various concentrations of NaCl during
in vitro production of solasodine was studied. The
in vitro yield was compared with the yield from leaves of field grown plant. Solasodine content was maximum (2.39 mg/g dry wt.) in regenerative callus when grown on medium added with 150 m
M NaCl; followed by
in vitro raised leaf of microshoot. Quantitative estimation of solasodine was carried out using a new HPTLC method, which is validated for its recovery and precession. The proposed HPTLC method showed a good linear relationship (
r2=0.994) in 50—2000 ng/spot concentration ranges. The data demonstrate that the solasodine production in cultures was growth dependent.
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Siling Wang, Guanhao Ye, Paul Wan Sia Heng, Mingxin Ma
2008 Volume 56 Issue 1 Pages
22-27
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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This study compared the granulation processes for different formulations using a laboratory-scale high shear mixer. The effects of critical process parameters (impeller speed, chopper speed and kneading time) on granule characteristics were evaluated. The characteristics of the granules studied included the size distribution, friability and morphological properties. The flow profiles of the wet mass and material deposition during the process were also studied. The results obtained showed that the effect of the impeller speed was determined by the starting material system. On the other hand, chopper speeds from 1200 to 3600 rpm and kneading times from 120 to 240 s had a consistent influence on all formulations. Moreover, it was found that the toroidal flow pattern of the wet mass could be maintained for a longer period and granules with a good spherical shape were obtained by removing the chopper during the last 120 s of the granulation process. In addition, the use of the pregelatinized starch in the formulation also led to a reduction in the wall adhesion of the material. It was concluded that the effectiveness of high shear wet granulation could be improved by choosing a proper combination of starting material and process parameters and by monitoring the mass motion during the process.
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Gedela Srinubabu, Bandaru Veera Venkata Ratnam, Allam Appa Rao, Medich ...
2008 Volume 56 Issue 1 Pages
28-33
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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A rapid tandem mass spectrometric (MS-MS) method for the quantification of Oxcarbazepine (OXB) in human plasma using imipramine as an internal standard (IS) has been developed and validated. Chromatographic separation was achieved isocratically on a C18 reversed-phase column within 3.0 min, using a mobile phase of acetonitrile–10 m
M ammonium formate (90 : 10 v/v) at a flow rate of 0.3 ml/min. Quantitation was achieved using multiple reaction monitoring (MRM) scan at MRM transitions
m/
z 253>208 and
m/
z 281>86 for OXB and the IS respectively. Calibration curves were linear over the concentration range of 0.2—16 μg/ml (
r>0.999) with a limit of quantification of 0.2 μg/ml. Analytical recoveries of OXB from spiked human plasma were in the range of 74.9 to 76.3%. Plackett–Burman design was applied for screening of chromatographic and mass spectrometric factors; factorial design was applied for optimization of essential factors for the robustness study. A linear model was postulated and a 2
3 full factorial design was employed to estimate the model coefficients for intermediate precision. More specifically, experimental design helps the researcher to verify if changes in factor values produce a statistically significant variation of the observed response. The strategy is most effective if statistical design is used in most or all stages of the screening and optimizing process for future method validation of pharmacokinetic and bioequivalence studies.
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Ayman Abouel Fetouh Gouda, Ragaa El-Sheikh, Alaa Sayed Amin
2008 Volume 56 Issue 1 Pages
34-40
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Four simple, quick and sensitive methods are described for the spectrophotometric determination of gatifloxacin. The methods are based on the reaction of gatifloxacin as n-electron donor with 7,7,8,8-tetracyanoquinodimethane (TCNQ); 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ); chloranilic acid (CLA) and
p-chloranil (CL) as π-acceptors to give highly colored complex species. The colored products are quantitated spectrophotometrically at 460, 841, 530 and 545 nm for DDQ, TCNQ, CLA and CL, respectively. Optimization of the different experimental conditions is described. Beer's law is obeyed in the concentration ranges 5—60, 1.5—18, 30—360 and 20—240 μg ml
−1 of gatifloxacin, but for more accurate analysis, Ringbom optimum concentration range was found to be 7.5—55, 3—16, 35—350 and 25—230 μg ml
−1 of gatifloxacin for DDQ, TCNQ, CLA and CL, respectively. The limits of detection and quantification were calculated and the relative standard deviations for different concentrations of gatifloxacin using various acceptors were <1.28%. The association constants of 1 : 1 complexes and standard free energy changes using Benesi–Hildebrand plots were studied. The proposed methods were successfully applied to the determination of gatifloxacin in pharmaceutical dosage forms without interference from common additives encountered.
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Bolat Makabel, Yuying Zhao, Bin Wang, Yanjing Bai, Qingying Zhang, Li ...
2008 Volume 56 Issue 1 Pages
41-45
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Alisol A 24-acetate is one of the main active triterpenoid compounds isolated from
Rhizoma Alismatis, which is a famous Traditional Chinese Medicine, and has been determined for the quality control of this crude drug. In this study, alisol A 24-acetate was found to be unstable in solvents and its stability in different solvents was investigated in detail. The results showed that alisol A 24-acetate and 23-acetate inter-transformed in solvents and the transformation rate was more rapid in protic solvents than in aprotic solvents. Moreover, both alisol A 24-acetate and 23-acetate were deacetylated to yield alisol A when kept in methanol for a long time. This is the first report on the structural transformation between alisol A 24-acetate, alisol A 23-acetate and alisol A. In addition, the single crystal X-ray structure of alisol A 24-acetate and the NMR data of alisol A 23-acetate were also reported for the first time.
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Xin-Luan Wang, Nai-Li Wang, Yan Zhang, Hao Gao, Wai-Yin Pang, Man-Sau ...
2008 Volume 56 Issue 1 Pages
46-51
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Drynaria fortunei (K
UNZE) J. S
M. (DFE) is one of the most frequently used traditional Chinese medicines prescribed for the treatment of osteoporosis in China. The present study was designed to investigate the osteoprotective constituents from
Drynaria fortunei. The 60% ethanol extract of the rhizome of
D. fortunei (DFE) was chromatographed on a D-101 macroporous resin column (φ 25×150 cm); three fractions (DFA eluted with water, DFB eluted with 30% and 50% ethanol, and DFC eluted with 95% ethanol) were obtained and their osteoprotective activity as examined both
in vivo and
in vitro. DFB showed significant activity on both the proliferation of UMR106 cells and promoting bone mineral density (BMD) in ovariectomized (OVX) mice. A bioactivity-guided method led to the isolation of 11 flavonoids from this fraction (DFB) with antiosteoporotic activity, including two new compounds, kaempferol 3-
O-β-
D-glucopyranoside-7-
O-α-
L-arabinofuranoside (1) and (
R)-5,7,3′,5′-tetrahydroxy-flavanone 7-
O-neohesperidoside (2), along with nine known ones: three flavanones (3—5), one flavone (7), one flavonol (6), two chromones (8, 10), maltol glucoside (9), and (−)-epicatechin (11). Compounds 4—11 are reported for the first time from this genus. We investigated the proliferative effects of the 11 compounds in the UMR106 osteoblastic cell line
in vitro. All compounds exhibited the proliferative activity in the UMR106 cells at most of the concentrations tested. Most compounds are reported for the first time from the
Drynaria genus and this was the first study of their proliferative activity in osteoblast-like cells. The main peaks in the HPLC fingerprint of the active fraction (DFB) were also identified.
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Yupei Shan, Lingling Xu, Yang Lu, Xiaobing Wang, Qitai Zheng, Lingyi K ...
2008 Volume 56 Issue 1 Pages
52-56
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Three new minor labdane diterpene glycosides, forskoditerpenoside C, D, and E (1—3), and a novel labdane diterpene forskoditerpene A (4) were isolated from the ethanol extract of the whole plant of
Coleus forskohlii. Their structures and relative stereochemistry were elucidated on the basis of extensive spectroscopic analyses including 1D-, 2D-NMR, and HR-ESI-MS experiments. Compounds 1—3 showed an unusual 8,13-epoxy-labd-14-en-11-one glycoside pattern. They showed relaxative effects on isolated guinea pig tracheal spirals
in vitro. Compound 4 with a cyclopropyl, confirmed by a single-crystal X-ray diffraction determination, is the first known labdane derivative with a spiro element.
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Abu Bakar Md., Yumiko Suzuki, Masayuki Sato
2008 Volume 56 Issue 1 Pages
57-59
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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N-Heterocyclic carbenes (NHCs) were generated
in-situ from imidazolium and imidazolinium salts by deprotonation of C-2 hydrogen and were used as ligands in the copper-catalyzed addition of diethylzinc to
N-sulfonylimines. The copper–NHC complexes were shown to possess an efficient ligand acceleration effect (LAE).
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Masanori Kuroyanagi, Ryuya Ikeda, Hui Yuan Gao, Norio Muto, Keisuke Ot ...
2008 Volume 56 Issue 1 Pages
60-63
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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In the screening of biologically active constituents from woody plants, the methanol extract of leaves of
Chamaecyparis obtusa showed potent neurite outgrowth-promoting activity in neuronal PC12 cells. The ethyl acetate-soluble fraction of the methanol extract showed potent activity and was separated by means of various chromatographic methods to give the two new compounds 1 and 2, as well as 11 known lignan and sesquiterpene derivatives. The structures of the new compounds were determined to be 9-
O-acetyldihydrosesamin (1) and 9-
O-(11-hydroxyeudesman-4-yl)dihydrosesamin (2), respectively, in NMR studies including 2D-NMR experiments. Of the 13 compounds, the known compound hinokinin (5) and the new compound 2 showed potent neurite outgrowth-promoting activity in PC 12 cells.
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Naoki Yamakawa, Masamitsu Sumimoto, Takashi Matsumoto, Koji Yuto, Yuzo ...
2008 Volume 56 Issue 1 Pages
64-69
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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1H-NMR spectra of square-planar complexes with the formula [Pt(L
1)(L
2)]X
2 where L
1 is 2,2′-bipyridine (bpy) or 1,10-phenanthroline (phen) and L
2 is
N-(1-naphthyl)methyl-1,2-ethanediamine (Npen) or
N-(9-anthryl)methyl-1,2-ethanediamine (Aten) indicate that the
N-naphthylmethyl and
N-anthrylmethyl groups are forced to adopt a pseudo axial disposition due to intramolecular repulsion of hydrogen atoms of the aromatic diimines. The aromatic–aromatic interactions in the
N-arylmethyl-1,2-ethanediamine complexes and aromatic diimines caused them to undergo intramolecular stacking.
1H-NMR spectra of these complexes showed a significant concentration and temperature dependence. The monomer–dimer equilibrium was estimated, based on the concentration dependency. Restricted single bond rotation was estimated from temperature dependency data. The rotation of the anthracene ring of the [Pt(bpy)(Aten)]
2+ complex showed an activation energy of
ca. 38 kJ mol
−1, which is in good agreement with a mechanism involving successive rotations about single bonds with restriction by intramolecular aromatic–aromatic ring interactions.
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Malgorzata Sznitowska, Malgorzata Klunder, Marcin Placzek
Article type: Notes
2008 Volume 56 Issue 1 Pages
70-74
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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The aim of this study was to find a biocompatible, lecithin-based carrier for paclitaxel (PTX) suitable for intravenous infusion and ensuring a soluble PTX concentration of 100 mg/100 ml or higher for at least 24 h. Aqueous dispersions of egg or soya lecithin (water–lecithin dispersions, WLD), mixed micellar (MM) solutions of egg lecithin and sodium deoxycholate, and formulations containing lecithin plus the co-surfactants and co-solvents poloxamer, polysorbate, Span, benzalkonium chloride, and macrogol were investigated. Amorphous PTX was prepared by lyophilization. PTX co-lyophilized with surfactants was also studied. Unlike crystalline PTX, the drug in an amorphous form is easily soluble in 1—5% (w/w) WLD or in MM. The highest solubility (up to 570 mg/100 ml) was achieved in 5% WLD. Dissolved PTX precipitated from all tested formulations over 24 h. Despite this, concentrations of dissolved PTX of 100 mg/100 ml or higher were observed after 24 h in 5% egg WLD, 1—5% soya WLD, and in 5% MM (lecithin : deoxycholate ratio 1 : 1 w/w). When four different batches of 5% egg WLD were prepared, containing PTX in clinically relevant concentration of 100 mg/100 ml, no precipitation of PTX was observed within 24 h and this formulation is the most promising candidate for further
in vivo studies. Neither additional surfactants nor co-lyophilization increased PTX solubility in the lecithin-based carriers. The use of parenteral emulsions as solvents for the co-lyophilized PTX also failed to increase the solubility of the drug up to the target concentration.
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Xiao-Qiu Liu, Li-Li Du, Wei-Wei Li, Hong-Feng Guan, Fang Liu
Article type: Notes
2008 Volume 56 Issue 1 Pages
75-78
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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A qualitative and quantitative analysis method was established to improve quality assessment standards for Rhizoma Polygoni Bistortae (
Polygonum bistorta L.) and differentiate commercial bistorta rhizome from closely related herbs by TLC and HPLC-DAD fingerprinting. Three compounds including phenolic acid and flavane were identified by comparison with standard compounds and quantified simultaneously by HPLC-DAD simultaneously. A comprehensive validation of the method that included sensitivity, linearity, repeatability and recovery was conducted.
Paris polyphylla S
M., a herb often mixed with
Polygonum bistorta L. in China due to their same popular name “Caoheche” in history, was successfully distinguished by thin-layer chromatography (TLC) fingerprinting of the petroleum-soluble fraction.
Polygonum paleaceum W
ALL., another herb often mixed with
Polygonum bistorta L. due to their similar external appearances, was distinguished by HPLC fingerprinting.
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Ahmad Shaabani, Ali Maleki
Article type: Notes
2008 Volume 56 Issue 1 Pages
79-81
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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The direct conversion of α-hydroxy ketones and α-keto oximes into quinoxaline derivatives in the presence of a catalytic amount of ceric ammonium nitrate
via metal-catalyzed aerobic oxidation followed by
in situ trapping with aromatic 1,2-diamines in water as a green and efficient reaction media, is reported.
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Marie-Eve Bradette-Hébert, Jean Legault, Serge Lavoie, Andr&eac ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
82-84
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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A new labdane diterpene, 9α,16ξ-dihydroxy-6-oxo-7,13-labdadien-15,16-olide (solicanolide, 1) and six known compounds identified as quercetin (2), 3-
O-caffeoylquinic acid (3, neochlorogenic acid), 5-
O-caffeoylquinic acid (4, chlorogenic acid), 4,5-di-
O-caffeoylquinic acid (5), 3,5-di-
O-caffeoylquinic acid (6) and 3,4-di-
O-caffeoylquinic acid (7) were isolated from the flowers of
Solidago canadensis. To our knowledge, compound 7 was isolated for the first time in
S. canadensis. This work describes the isolation of compounds 1—7 and the structure elucidation of a new compound identified as compound 1. Solicanolide (1) showed cytotoxic activity against A549 (IC
50: 13±2 μ
M), DLD-1 (IC
50: 26±2 μ
M) and WS1 (IC
50: 17±1 μ
M) cell lines.
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JunPil Jang, MinKyun Na, Phuong Thien Thuong, Dieudonné Njamen, ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
85-88
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Phytochemical study on an EtOAc-soluble extract of the root bark of
Erythrina mildbraedii resulted in the isolation of six prenylated flavonoids 1—6. Based on physicochemical and spectroscopic analyses, their structures were determined to be new natural products licoflavanone-4′-
O-methyl ether (1), 2′,7-dihydroxy-4′-methoxy-5′-(3-methylbut-2-enyl)isoflavone (2), and (3
R)-2′,7-dihydroxy-3′-(3-methylbut-2-enyl)-2‴,2‴-dimethylpyrano[5‴,6‴ :4′,5′]isoflavan (3), along with three known compounds erythrinin B (4), abyssinin II (5), and parvisoflavone B (6). All the isolates, except for compound 4, inhibited PTP1B activity
in vitro with IC
50 values ranging from 5.3 to 42.6 μ
M. This result further suggests that the prenyl group on the B ring of flavonoids plays an important role in suppressing the enzyme PTP1B.
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Kazuko Yoshikawa, Naoki Kokudo, Masami Tanaka, Tatsuro Nakano, Hirofum ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
89-92
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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From
Cladonia rangiferina were isolated two novel abietane diterpenoids, hanagokenols A (1) and B (2). Also in this investigation, four known abitetane diterpenoids (3—6), four known labdane diterpenoids (7—10), one known isopimarane diterpenoid (11), and six known aromatic compounds were isolated. These structures were elucidated primarily through extensive NMR experiments. Hanagokenol A (1) was a unique abietane diterpene having an ether linkage between C-6 and C-18 of sugiol. Hanagokenol B (2) is also a unique secoabietane diterpene, having γ-lactone which occurred by cleavage and subsequently oxidation between C-6/C-7 of 12-hydroxydehydroabietinol. Furthermore, all the isolated compounds (1—17) were tested for the antimicrobial activity against methicillin-resistant
Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).
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Hiroyuki Fuchino, Setsuko Sekita, Kanami Mori, Nobuo Kawahara, Motoyos ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
93-96
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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A new furostan-type saponin (1) was isolated from the methanolic extract of
Brunfelsia grandiflora leaves, together with four known compounds. The chemical structure of 1 was determined by spectroscopic analysis and chemical reaction to be 26-
O-β-
D-glucopyranosyl 22α-methoxyfurost-3β,26-diol 3-
O-β-
D-xylopyranosyl(1→3)-{β-
D-glucopyranosyl(1→2)}-β-
D-glucopyranosyl(1→4)-β-
D-glucopyranoside. Compound 1 showed potent leishmanicidal activity
in vitro against
Leishmania major.
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Soong-Yu Kuo, Tian-Jye Hsieh, Yau-Der Wang, Wen-Li Lo, Yen-Ray Hsui, C ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
97-101
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Two new butanolides, subamolide D (1) and subamolide E (2), and a new secobutanolide, secosubamolide A (3), along with 21 known compounds were isolated from the leaves of
Cinnamomum subavenium. The structures of 1—3 were determined by spectroscopic analysis. Propidium iodide staining and cytometry analysis were used to evaluate the cell cycle progression of the treated SW480 cells and it was found that 1 and 2 caused DNA damage in a dose- and time-dependent manner.
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Pei Hua Zhao, Li Mei Sun, Xiu Jin Liu, Mei Ai Cao, Cheng Shan Yuan
Article type: Notes
2008 Volume 56 Issue 1 Pages
102-104
Published: January 01, 2008
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Chemical investigation of the roots of
Dictamnus radicis Cortex led to the isolation of a new limonoid isodictamdiol (1) and a known dictamdiol (2), the first 5
S/9
S-type degraded limonoids, together with other six known limonoids (3—8). The chemical structures were identified on the basis of modern spectroscopic methods, including IR, MS, NMR (
1H-NMR,
13C-NMR,
1H–
1H COSY, HMQC, HMBC, NOESY). Additionally, the absolute configurations of limonoid isodictamdiol (1) and dictamdiol (2) were separately elucidated by single crystal X-ray diffraction, as well as their circular dichroism spectra. Furthermore, all compounds were evaluated for antibacterial activity against three bacterial cultures.
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Ju Sun Kim, Min-Hye Yean, Eun-Ju Lee, Hye Sil Jung, Joo Young Lee, Yoo ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
105-108
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Two new cycloartane-type triterpenoid saponins were isolated from the roots of
Astragalus membranaceus (F
ISCH.) B
GE. (Leguminosae) cultivated in Kangwon province, Korea. These saponins were named astramembranosides A and B and were established to be cycloastragenol 6,25-di-
O-β-
D-glucopyranoside (astramembranoside A) and cyclocanthogenin 3-
O-β-
D-glucopyranosyl(1→2)-β-
D-xylopyranoside (astramembranoside B) on the basis of chemical and spectral evidence. In addition, 12 known saponins were also isolated from the same materials. Although cycloastragenol 3-
O-xyloside and agroastragalosides I and II have already been isolated from
A. membranaceus adventitious roots, these three saponins together with brachyoside B and azukisaponin V methyl ester were isolated for the first time from this plant.
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Chi-Shiun Chiang, Ching-Fang Yu, Li-Wu Chiang, Shao-Wei Chen, Jem-Mau ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
109-111
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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A cell survival assay of the four arabinosyl uridine analogs with functionalities of 5-fluoro, 5-fluorovinyl, 5-iodo, and 5-iodovinyl as potential positron-emitter tagged probe for monitoring cancer gene therapy were performed. Cytotoxicities of 5-fluoro-, 5-iodo-, 5-fluorovinyl, and 5-iodovinyl arabinosyl uridines against SR-39 thymidine kinase transfected murine prostate cancer cells have been evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. None of them showed significant bioactivity. A
syn conformation derived from intra-hydrogen bonding was suggested for the unfavorable interaction and diminished bioactivity.
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Akimori Wada, Fei Wang, Masayoshi Ito
Article type: Notes
2008 Volume 56 Issue 1 Pages
112-114
Published: January 01, 2008
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A convenient synthesis of 3,4-didehydroretinal was developed. The Horner–Emmons reaction between 3,4-didehydro-β-ionone and diphenyl phosphonate in the presence of crown ether gave the retinonitrile as an isomeric mixture, in which the newly produced double bond was predominantly 11
Z-form. After separation of the 11
Z-form retinonitrile, it was converted into the corresponding retinal in good yield without isomerization of the double bonds.
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UiJoung Youn, Quan Cheng Chen, Ik Soo Lee, HongJin Kim, Jae-Kuk Yoo, J ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
115-117
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Two new lignans, 4-methoxymagnaldehyde B (1) and coumanolignan (2), were isolated from the stem bark of
Magnolia obovata, together with 11 known compounds (3—13). The structures of compounds 1 and 2 were determined to be 5′-allyl-2′-hydroxyphenyl-4-methoxy-3-cinnamic aldehyde (1) and 6-allyl-8-(5′-allyl-2′-hydroxyphenyl)coumarin (2) on the basis of spectroscopic and physicochemical analyses including 2D NMR and high-resolution EI-MS. Compounds 1—8, 11, 12, and 13 were tested
in vitro for their cytotoxic activities against the HeLa, A549, and HCT116 cancer cell lines. Among the compounds tested, compound 1 showed the strongest cytotoxic activity against the HCT116 cancer cell line, with an IC
50 value of 1.3 μg/ml.
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Masako Kinoshita, Takahiro Miyake, Yuusuke Arima, Minako Oguma, Hiroyu ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
118-123
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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The reported enzymatic resolution products {acetate of (1
S,4a
S,8a
S)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-
trans-naphthalene-1-methanol-2-ethylene acetal} (8a
S)-5 (>99% ee)] and [(1
R,4a
R,8a
R)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-
trans-naphthalene-1-methanol-2-ethylene acetal (8a
R)-4 (98% ee) were converted to (+)-α-polypodatetraene (1) and methyl (5
R,10
R,13
R)-labda-8-en-15-oate (2), respectively. For the synthesis of (5
R,10
R,13
R)-2, chiral isoprene congener (3
S)-26 corresponding to the right part of 2 was synthesized based on the lipase-assisted resolution of (±)-2-methyl-3- (
p-methoxyphenyl)propanol (17).
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Makoto Makoto Iwashima, Natsuko Tako, Tomoyo Hayakawa, Takayuki Matsun ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
124-128
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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Two new chromane type meroterpenoids were isolated from the methanolic extract of the brown alga,
Sargassum micracanthum. Their structures were elucidated based on spectroscopic analysis and chemical conversion. The absolute stereochemistry of the methyl group at C-8′ in 1 and related compounds were determined by modified Mosher's method.
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Ko Yasumoto, Akinori Nishigami, Hiroaki Aoi, Chise Tsuchihashi, Fumie ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
129-132
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
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4,8-Dimethylnonyl sulfate (1) and 3-methyl-4
E-decenyl sulfate (2) were isolated from
Daphnia pulex as the
Daphnia kairomones that induced morphological defense of a freshwater phytoplankton
Scenedesmus gutwinskii var.
heterospina (NIES-802). The absolute configuration at C4 of 1 was determined by Ohrui's method applied to alcohol 3. The absolute stereochemistry at C3 of 2 was determined by
1H-NMR analysis of the (
R)-1NMA ester of alcohol 11.
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Ko Yasumoto, Akinori Nishigami, Hiroaki Aoi, Chise Tsuchihashi, Fumie ...
Article type: Notes
2008 Volume 56 Issue 1 Pages
133-136
Published: January 01, 2008
Released on J-STAGE: January 01, 2008
JOURNAL
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New aliphatic sulfates and sulfamates were isolated from
Daphnia pulex as the
Daphnia kairomones that induced morphological defense of a freshwater phytoplankton
Scenedesmus gutwinskii var.
heterospina (NIES-802). Their structures were determined by spectroscopic and synthetic studies.
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