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Volume 56, Issue 3
Displaying 1-32 of 32 articles from this issue
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Regular Articles
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Masahiro Tada, Risa Ishiguro, Ryohei Izumi2008 Volume 56 Issue 3 Pages 239-242
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA stable symmetric diacyl peroxide, m-chlorobenzoyl peroxide (mCBPO), and an asymmetric diacyl peroxide, chloroacetyl m-chlorobenzoyl peroxide (CAMCBPO), were synthesized from m-chloroperbenzoic acid. Both peroxides oxidized phenols selectively at the ortho position predoninantly. CAMCBPO gave para-oxidized compounds as minor products from some phenols. The improvement of the yield of ortho-oxidation of phenols with mCBPO was also reported.View full abstractDownload PDF (146K) -
Yukako Ito, Yoshinori Ohashi, Atsushi Saeki, Nobuyuki Sugioka, Kanji T ...2008 Volume 56 Issue 3 Pages 243-246
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSAs a percutaneous delivery device, self-dissolving micropiles (SDMPs) composed of chondroitin sulfate and insulin were prepared under room temperature from highly concentrated solution, glue. The mean weight of SDMP was 1.03±0.04 mg. One insulin SDMP was percutaneously administered to the shaved abdominal skin of four beagle dogs at insulin dose level of 1.0 and 2.0 IU/dog. After administration, blood samples were collected for 6 h and plasma glucose levels were measured. The time when minimum plasma glucose level appeared, Tmin, was 1.38±0.2 h for 1.0 IU study and 1.38±0.1 h for 2.0 IU study and clear dose-dependent hypoglycemic effect of insulin was observed in the dose range. By comparing the area above the plasma glucose level vs. time curve (AAC) between insulin SDMP and subcutaneous (s.c.) injection solution, the relative pharmacological availabilities were 99% (1.0 IU) and 90% (2.0 IU), respectively. To ascertain the usefulness of insulin SDMP, oral glucose tolerance test (OGTT) was performed. When dogs were treated with insulin SDMPs, 2.0 IU, followed by an OGTT 30 min, glycemia did not appear for 5 h. On the other hand, when OGTT was performed at 1 h after insulin SDMP administration, hypoglycemia appeared as in the case of s.c. injection of insulin solution, 2.0 IU. Insulin SDMP improved the oral glucose challenge for 3 h, with a maximum effect at 30 min before the administration of glucose. Those results suggest the usefulness of a SDMP for the percutaneous delivery of peptide/protein drugs like insulin.View full abstractDownload PDF (98K) -
Kuniharu Utsuno2008 Volume 56 Issue 3 Pages 247-249
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSInteraction between Mn2+ ion and the two forms of DNA duplex (supercoiled and linearized pUC119 DNA) in solution has been examined by isothermal titration calorimetry. Although DNA condensation reaction heat was observed at 323 K, this was not the case at 298 K. DNA condensation was entropically driven and supercoiled DNA was found to be more susceptive. The enthalpy of DNA condensation is estimated 0.42 kJ/mol for both DNA forms. Conversely, the entropy of DNA condensation was 0.13 kJ/mol K for supercoiled DNA, and 0.12 kJ/mol K for linearized DNA. The difference of entropy is attributable to their DNA conformation.View full abstractDownload PDF (174K) -
Chun-Lan Zou, Xiao-Yu Liu, Feng-Peng Wang, Qiao-Hong Chen2008 Volume 56 Issue 3 Pages 250-253
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSTreatment of compounds 2 and 5, both from the C19-diterpenoid alkaloid deltaline 1, with 5% NaOH methanol (room temperature, 16 h) and NaOH-N,N-dimethylformamide (reflux, 10 h) led to the two novel skeletal rearrangement products 4 (90%) and 6 (62%), respectively, involving Wagner–Meerwein rearrangement and Grob fragmentation. Their structures were fully characteristized based on 2D NMR and HR-MS data.View full abstractDownload PDF (198K) -
Richer Chen, Hirokazu Okamoto, Kazumi Danjo2008 Volume 56 Issue 3 Pages 254-259
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA previous study on spray-drying demonstrated that it could promote the solubility of poorly water-soluble drugs using water-soluble polymers. Here, the preparation of composite particles of salbutamol sulfate (Sb) with water-insoluble polymers, such as Eudragit® RS (RS) or Eudragit® RL (RL) as a carrier, was examined. Despite the water insolubility of both polymers, the permeability of water was low in the former but high in the latter. We attempted to prepare controlled release composite particles by exploiting the characteristics of these carriers. The composite particles of the three components (Sb, RS, and RL) were prepared using a 4-fluid nozzle spray-dryer, and their physico-chemical and dissolution properties were compared with physical mixtures. Examination of particle morphology by scanning electron microscopy (SEM) revealed that the particles from the spray-drying process had atomized to several microns and were spherical. Analysis by X-ray diffraction and differential scanning calorimetry revealed that diffraction peaks and heat of fusion of Sb in the spray-dried samples decreased, indicating that the drug was amorphous and formed a solid dispersion. FT-IR analysis suggested that the amino group of Sb and a carbonyl group of the polymers formed a hydrogen bond. A dissolution test of Sb-RS-RL particles prepared using the 4-fluid nozzle spray-drying method showed that release rates were depressed significantly compared to the physical mixture at pH 1.2 and 6.8, and the depression was greater when RS was used instead of RL, presumably because of the permeability difference. The compression of these particles into tablets revealed that desirable controlled released dosage forms could be prepared. In addition, Sb was used to simulate an anti-asthmatic drug. For this an Andersen cascade impactor for dry powder inhalers was used to investigate delivery to the lungs.View full abstractDownload PDF (475K) -
Takahiro Mukai, Noriko Suganuma, Kenta Soejima, Junichi Sasaki, Fumihi ...2008 Volume 56 Issue 3 Pages 260-265
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSMatrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala-β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.View full abstractDownload PDF (179K) -
Rie Kusano, Hisashi Andou, Miho Fujieda, Takashi Tanaka, Yosuke Matsuo ...2008 Volume 56 Issue 3 Pages 266-272
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSLipase and amylase inhibitory activities of black tea were examined. After solvent partitioning of a black tea extract with the ethyl acetate and n-butanol, the two soluble fractions showed comparable inhibitory activities. Activity in the ethyl acetate fraction was mainly attributable to polyphenols with low-molecular weights, such as theaflavin gallates. On the other hand, the active substance in the n-butanol layer was ascertained to be a polymer-like substance. 1H- and 13C-NMR spectra showed signals arising from the flavan A-ring and galloyl groups, although signals due to flavan B-rings were not detected, suggesting that the polymer-like substances were generated by oxidative condensation of flavan B-rings, a result which was previously deduced from our results of in vitro catechin oxidation experiments. Enzymatic oxidation of epicatechin 3-O-gallate produced a similar polymer-like substance and suggested that condensation between a B-ring and galloyl groups was involved in the polymerization reaction.View full abstractDownload PDF (631K) -
Ayarivan Puratchikody, Govindasamy Nagalakshmi, Mukesh Doble2008 Volume 56 Issue 3 Pages 273-281
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSTwenty eight analogues of benzimidazoles had been synthesized and tested for their antimicrobial activity against four bacteria (Staphylococcus auerus, Escherichia coli, Bacillus pumilus and Proteus vulgaris) and two fungi (Aspergillus flavus and Aspergilus niger). Compounds with R as C6H4NO2 and R′ as SO2C6H4–CH3(p), with R as C6H4OCH3 and R′ as SO2C6H4–CH3(p), and with R as CH2C6H5 and R′ as CH2(CH2)9Cl exhibited comparable or higher antibacterial activity than Ciprofloxacin against S. auerus and E. coli and, higher activity than Nystatin against A. flavus. Several other compounds showed better activity than the standard antibiotic for E. coli. Compounds with R as CCl3 and R′ as SO2C6H4–CH3(p) or COC6H5 exhibited the lowest activity against all the organisms. Addition of methylene groups in the R′ position increased activity. Many of the compounds showed better activity than Ciprofloxacin for one or more organisms. Compound with R as CH2OC6H5 and R′ as CH2(CH2)9Cl exhibited higher activity against both the fungii than the control Nystatin. Quantitative structure activity relationships (QSARs) developed were good for all the organisms (R2=0.65 to 0.88; Radj2 = 0.63 to 0.86) and the predictive capability of the developed models was also reasonable (q2=0.52 to 0.83). The models had two to three independent variables. The data for the models which had three independent variables were divided into training and test/validation sets. The former set was used to develop the QSAR and these developed models were used to predict the activity of the test set data. In all the three cases the predictive capability of the models was good. The molecular descriptors identified were predominantly log P, electronic parameters, molecular size, shape and area. A positive correlation existed between the antibacterial activity and the first principal component.View full abstractDownload PDF (209K) -
Mehmet Aslanoglu, Aysegul Kutluay, Sultan Abbasoglu, Serpil Karabulut2008 Volume 56 Issue 3 Pages 282-286
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA reliable and reproducible method for the determination of uric acid in urine samples has been developed. The method is based on the modification of a glassy carbon electrode by 3-acetylthiophene using cyclic voltammetry. The poly(3-acetylthiophene) modified glassy carbon electrode showed an excellent electrocatalytic effect towards the oxidation of uric acid in 0.1 m phosphate buffer solution (PBS) at pH 7.2. Compared with a bare glassy carbon electrode (GCE), an obvious shift of the oxidation peak potential in the cathodic direction and a marked enhancement of the anodic current response for uric acid were observed. The poly(3-acetylthiophene)/GCE was used for the determination of uric acid using square wave voltammetry. The peak current increased linearly with the concentration of uric acid in the range of 1.25×10−5—1.75×10−4 M. The detection limit was 5.27×10−7 M by square wave voltammetry. The poly(3-acetylthiophene)/GCE was also effective to determine uric acid and ascorbic acid in a mixture and resolved the overlapping anodic peaks of these two species into two well-defined voltammetric peaks in cyclic voltammetry at 0.030 V and 0.320 V (vs. Ag/AgCl) for ascorbic acid and uric acid, respectively. The modified electrode exhibited stable and sensitive current responses toward uric acid and ascorbic acid. The method has successfully been applied for determination of uric acid in urine samples.View full abstractDownload PDF (157K) -
Masahiro Tada, Jun Kurabe, Hiroaki Yasue, Tomohisa Ikuta2008 Volume 56 Issue 3 Pages 287-291
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSThe syntheses of four totarane diterpenes—totarol, 8,11,13-totaratriene-12,13-diol, 6-deoxymaytenoquinone and maytenoquinone—are described. Totarol was synthesized via cyclization of a modified polyene. 8,11,13-Totaratriene-12,13-diol was prepared from natural totarol by ortho-oxidation with mCBPO (m-chlorobenzoyl peroxide). Maytenoquinone and 6-deoxymaytenoquinone were synthesized from 8,11,13-totaratriene-12,13-diol. 1H-NMR analysis showed that tautomeric isomerization between 6-deoxymaytenoquinone (2-hydroxy-4-quinone methide) and the ortho-quinone was very slow.View full abstractDownload PDF (166K) -
Sanae Matsuda, Hiroharu Shibayama, Masayoshi Hisama, Mamitaro Ohtsuki, ...2008 Volume 56 Issue 3 Pages 292-297
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSWe investigated the inhibitory effects of a novel amphiphilic ascorbic derivative, disodium isostearyl 2-O-L-ascorbyl phosphate (VCP-IS-2Na), synthesized from a hydrophilic ascorbic derivative, sodium-2-O-L-ascorbyl phosphate (VCP-Na), on melanogenesis in cultured human melanoma cells, normal human melanocytes, and three-dimensional cultured human skin models. Melanin synthesis in melanoma cells treated with VCP-IS-2Na at 300 μM and melanocytes treated with VCP-IS-2Na at 100 μM decreased to 23% and 52% of that in non-treated cells, respectively, and the cell viability was not affected. VCP-IS-2Na also significantly suppressed the cellular tyrosinase activity of melanoma cells and melanocytes. Melanin synthesis in human skin models was evaluated by macro- and microscopic observations of its pigmentation and quantitative measurements of melanin. Treatment of the human skin models with 1.0% VCP-IS-2Na did not inhibit cell viability, while melanin synthesis was decreased to 21% of that in the control. In contrast, L-ascorbic acid (VC) and VCP-Na did not seem to inhibit melanin synthesis and cellular tyrosinase activity. These results indicate that VCP-IS-2Na may be an effective whitening agent for the skin, and we expect the application of VCP-IS-2Na in the cosmetic industry.View full abstractDownload PDF (675K) -
Haruka Fujimoto, Hiroshi Aoyama, Tomomi Noguchi-Yachide, Yuichi Hashim ...2008 Volume 56 Issue 3 Pages 298-304
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSFusarielin A shows anti-angiogenic activity in the human umbilical vein endothelial cell (HUVEC) tube formation assay. Structural development studies indicated the importance of the hydroxyl groups in this molecule. A 3H-labeled derivative and a fluorescent affinity-labeling agent were prepared and used to examine the cellular distribution and biological behavior of fusarielin A.View full abstractDownload PDF (958K) -
Rika Nishikiori, Mariko Yamaguchi, Keisuke Takano, Tokujiro Enatsu, Ma ...2008 Volume 56 Issue 3 Pages 305-307
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSAbsorption spectra of polycrystalline L-, D-, and DL-tartaric acid have been measured by terahertz time domain spectroscopy (THz-TDS). Different absorption bands are observed for DL-tartaric acid and its enantiomers (L- and D-tartaric acid). This result shows that the THz-TDS can be used for distinguishing between DL-tartaric acid and enantiomers (L- and D-tartaric acid). Moreover, partial least square (PLS) can be found to improve the quantitation of L-tartaric acid in L- and DL-tartaric acid mixture by THz-TDS.View full abstractDownload PDF (101K) -
Mitsuyasu Ushijima, Noriko Komoto, Yoshimi Sugizono, Ikuko Mizuno, Mas ...2008 Volume 56 Issue 3 Pages 308-314
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSIn the course of the development of new designer foods using the roots of Codonopsis lanceolata, we found that hot-water extracts of C. lanceolata recovered decreased testosterone levels in the blood and accelerated the restoration of reproductive dysfunction induced by hyperthermic treatment in male mice. Thus we studied the constituents of the polar fraction of the roots of C. lanceolata and identified six new triterpene saponins, lancemasides B (2), C (3), D (4), E (5), F (6), and G (7), along with the known saponin lancemasaide A (1) and phenylpropanoid glycosides 8—10. The structures of the new compounds 2—7 were determined by means of spectral data including 2D-NMR studies and chemical reactions to be oleanan-type bisdesmoside with sugars at C-3 and C-28. Compounds 2—6 have echinocystic acid as an aglycone, and compound 7 has asterogenic acid as an aglycone. Identification of the sugars and determination of their D,L-chiralities were carried out by application of the exciton chirality method to the per-O-p-bromobenzoylmethyl sugar derived from saponins.View full abstractDownload PDF (157K) -
Tsutomu Warashina, Tadataka Noro2008 Volume 56 Issue 3 Pages 315-322
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSTwenty-six new acylated-oxypregnane glycosides were obtained along with three known cardenolide glycosides from the roots of Asclepias curassavica (Asclepiadaceae). The new compounds were confirmed to contain 12-O-benzoylsarcostin, 12-O-benzoyldeacylmetaplexigenin, kidjolanin, and 12-O-benzoyltayloron, and one new acylated-oxypregnane, 12-O-(E)-cinnamoyltayloron, as their aglycones, using both spectroscopic and chemical methods.View full abstractDownload PDF (261K) -
Hideko Kawaki2008 Volume 56 Issue 3 Pages 323-327
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSThe solute–stationary liquid interaction in gas liquid chromatography (GLC) was determined using Eyring's model. The interaction was determined to be the physical adsorption. The descriptor σM was derived and estimated by van der Waals interactions. The CH/π interaction energies were calculated by Tsuzuki et al. using the high-level ab initio calculations. The CH/π interaction energy was concluded to consist of the dispersion energy (Edis) rather than the electrostatic (Ees) and charge-transfer (Ect) energies. These energies were in good agreement with our descriptor σM. Furthermore, the macroscopic σM also had microscopic support through the weak CH/π interactions. In substituted benzenes, regression analyses were carried out using σM for the relative retention values, log γ, as a measure of the solute–stationary liquid interaction. The analyses revealed good results under non-polar conditions. The log γ values therefore consisted primarily of contributions from the dispersion interaction and the CH/π complex. Moreover, these values were useful when added to the electrostatic term (our descriptor σes) for polar solutes. That is, the log γ values were estimated by the regression analyses using both σM and σes, and were in good agreement with the predicted values.View full abstractDownload PDF (139K) -
Saori Nakagawa, Riho Suzuki, Reiko Yamazaki, Yoko Kusuhara, Shoko Mits ...2008 Volume 56 Issue 3 Pages 328-331
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA simple column-switching high performance liquid chromatographic (HPLC) method that does not require any complicated pretreatment has been developed to determine voriconazole in human plasma samples. An internal standard (IS) and borate buffer (pH 9.0) were added to plasma samples, which were then injected directly into the column-switching HPLC system using MAYI-ODS as a pre-column. The calibration curve for voriconazole showed good linearity in the range of 0.2—10 μg/ml in human plasma. The mean RSD (%) value of intra-day (n=6) and inter-day (n=5) precision were less than 5.4% and 8.2%, respectively. This system could make more than three hundred successive, accurate measurements when a washing step with ammonium acetate solution was added. This method was successfully applied to measure the therapeutic voriconazole level in patients' plasma, and was used in a study of voriconazole pharmacokinetics after oral administration.View full abstractDownload PDF (388K) -
Magie Melanie Kapojos, Remy Emile Petrus Mangindaan, Takahiro Nakazawa ...2008 Volume 56 Issue 3 Pages 332-334
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSThree new sesquiterpenes, 2-deoxy-7-O-methyllemnacarnol (1), 2-deoxy-12α-ethoxy-7-O-methyllemnacarnol (2), and 2-deoxy-12α-methoxy-7-O-methyllemnacarnol (3), were isolated from a soft coral Nephthea sp. collected in Indonesia, together with five known sesquiterpenes. The structures of the new compounds were assigned on the basis of their spectroscopic data.View full abstractDownload PDF (158K) -
Satoru Azukizawa, Masayasu Kasai, Kenji Takahashi, Tomohiro Miike, Kaz ...2008 Volume 56 Issue 3 Pages 335-345
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and biologically evaluated. (S)-2-Benzyl-7-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (10, KY-021) was identified as a novel peroxisome proliferators-activated receptor (PPAR)γ agonist, which showed potent activity in human PPARγ (EC50=11.8 nM). KY-021 reduced plasma glucose and triglyceride levels at 3 mg/kg/d for 7 d in male KK-Ay mice. KY-021 also decreased plasma triglyceride levels at 0.3—3 mg/kg/d for 6 d, and improved oral glucose tolerance at 1 and 3 mg/kg/d for 7 d in male Zucker fatty rats. Maximal plasma concentration of KY-021 after oral administration at 10 mg/kg was 6.6 μg/ml and 2.1 μg/ml in male ICR mice and male SD rats, respectively. Repeated oral administration of KY-021 at 30 mg/kg/d for 10 weeks had little toxicity in male SD rats. These results demonstrated that KY-021 has great potential as an efficacious and safe drug for diabetes.View full abstractDownload PDF (275K) -
Yoshifumi Ikee, Kana Hashimoto, Mai Kamino, Masaaki Nakashima, Kazuhik ...2008 Volume 56 Issue 3 Pages 346-356
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA series of 3-sulfenylazetidine derivatives 5a—f were synthesized via the ring-opening reactions of 1-azabicyclo[1.1.0]butane (ABB, 3) with thiols 4a—f in 50—92% yields. Treatment of ABB (3) with aromatic amines 9a—e and dibenzylamine (9f) in the presence of Mg(ClO4)2 afforded the corresponding 3-aminoazetidine derivatives 10a—f in 24—65% yields. N-Benzyl-3-bromoazetidine (13), which was obtained by the reaction of ABB (3) with benzyl bromide, gave 3-aliphatic amino-substituted azetidine derivatives 15a, b. Novel fluoroquinolones 7a—f, 11a—f, 16a, b and 25a—c were obtained by the introduction of these azetidine derivatives into the C7 position of a quinolone nucleus 6 and N1-heterocyclic quinolones 21a—c in 21—83% yields. Some of them exhibited a greater antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) in comparison with that of clinically used fluoroquinolone, levofloxacin (LVFX).View full abstractDownload PDF (374K)
Notes
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Ketan Pravinbhai Modi, Natvarlal Manilal Patel, Ramesh Kishorilal Goya ...Article type: Notes
2008 Volume 56 Issue 3 Pages 357-359
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA selective, precise, and accurate high-performance thin-layer chromatographic (HPTLC) method has been developed for the analysis of L-dopa in Mucuna pruriens seed extract and its formulations. The method involves densitometric evaluation of L-dopa after resolving it by HPTLC on silica gel plates with n-butanol–acetic acid–water (4.0+1.0+1.0, v/v) as the mobile phase. Densitometric analysis of L-dopa was carried out in the absorbance mode at 280 nm. The relationship between the concentration of L-dopa and corresponding peak areas was found to be linear in the range of 100 to 1200 ng/spot. The method was validated for precision (inter and intraday), repeatability, and accuracy. Mean recovery was 100.30%. The relative standard deviation (RSD) values of the precision were found to be in the range 0.64—1.52%. In conclusion, the proposed TLC method was found to be precise, specific and accurate and can be used for identification and quantitative determination of L-dopa in herbal extract and its formulations.View full abstractDownload PDF (109K) -
Dan Tang, Hui-Jun Li, Ping Li, Xiao-Dong Wen, Zheng-Ming QianArticle type: Notes
2008 Volume 56 Issue 3 Pages 360-365
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSFive caffeoylquinic acid derivatives (CQAs), including methyl 3,4-di-O-caffeoylquinate (3,4-diCQM), methyl 3,5-di-O-caffeoylquinate (3,5-diCQM), 3,4-di-O-caffeoylquinic acid (3,4-diCQA), 3,5-di-O-caffeoylquinic acid (3,5-diCQA) and chlorogenic acid (CA), were isolated from Lonicera fulvotomentosa HSU et S. C. CHENG to be used as model compounds. The binding of these bioactive components to bovine serum albumin (BSA) was investigated by fluorescence quenching method. The results showed that there were binding affinities for CQAs with BSA, and the binding constants ranked in the following order: 3,4-diCQM>3,5-diCQM<3,4-diCQA>3,5-diCQA>CA, under the physiological conditions, which suggested that the numbers and the substituted positions of caffeoyl group as well as the esterification of carboxyl group in the molecular structures appeared to contribute moderate effects to the interaction processes. Furthermore, the Stern–Volmer curves demonstrated that CQAs caused the fluorescence quenching through a static quenching procedure. Thermodynamic analysis indicated that both hydrophobic and electrostatic interactions played major roles in stabilizing the complex. The binding distance for each binding reaction was also calculated by the Föster theory.View full abstractDownload PDF (231K) -
Biswanath Das, Kanaparthy Suneel, Katta Venkateswarlu, Bommena Ravikan ...Article type: Notes
2008 Volume 56 Issue 3 Pages 366-368
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSSulfonic acid functionalized silica catalyzed the three-component reaction of aromatic amines, α,β-unsaturated aldehydes and β-keto esters forming the corresponding 1,4-dihydropyridines in short reaction times and in high yields.View full abstractDownload PDF (105K) -
Chih-Chia Chiang, Tsu-Chung Chang, Hou-Jen Tsai, Ling-Yih HsuArticle type: Notes
2008 Volume 56 Issue 3 Pages 369-373
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSUV irradiation induced formation of reactive oxygen radical species and matrix metalloproteinases (MMPs) are thought to be involved in photo-damage to the skin. MMP-1 is the major collagenolytic enzyme responsible for collagen destruction in skin tissue. To develop new anti-photoaging agents, a series of 2,2′-dithiocinnamate derivatives and 2,2′-dithio or 2-thiobenzoate derivatives were designed and synthesized. The biological activities of the synthesized compounds were assayed for ABTS [2,2′-azinobis-(3-ethyl-benzo-thiazoline-6-sulfonic acid)] radical scavenging activity, MMP-1 inhibitory activity, and cytotoxicity to human dermal fibroblast cells. Compounds with potential of resistance to UV irradiation were identified. These compounds are expected to be useful for preventing photo-damage to the skin.View full abstractDownload PDF (504K) -
Erasmienne Tambou Ngouamegne, René Soh Fongang, Silvère ...Article type: Notes
2008 Volume 56 Issue 3 Pages 374-377
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSFrom the ethyl acetate extract of the stem bark of Endodesmia calophylloides (Guttiferae), a novel friedelane triterpenoid named endodesmiadiol (1), as well as the known compounds friedelin (2), canophyllol (3), canophyllal (4), cerin (5), morelloflavone (6), volkensiflavone (7), 8-deoxygartanin (8), 3β-acetoxyoleanolic acid (9) and 1,8-dihydroxy-3-isoprenyloxy-6-methylxanthone (10) have been isolated. The structures of these compounds were established by spectroscopic analysis, and the relative configuration of endodesmiadiol (1) was confirmed by X-ray diffraction. The antiplasmodial activity of the isolated compounds was evaluated against the W2 strain of Plasmodium falciparum which is resistant to chloroquine and other antimalarial drugs. All the compounds were found to be active with IC50 values ranging from 7.2 to 23.6 μM. The IC50 of endodesmiadiol was found to be 11.8 μM.View full abstractDownload PDF (129K) -
Masashi Taniguchi, Yasuto Uchio, Ko Yasumoto, Takenori Kusumi, Takashi ...Article type: Notes
2008 Volume 56 Issue 3 Pages 378-382
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSNew brominated fatty acids (3, 5—8, 10) and new sterol esters (14—16) have been isolated from an unidentified marine sponge collected in Papua New Guinea. Their structures were determined on the basis of their spectroscopic data. A major component of the marine sponge (1) was tested for activities against Arutemia salina and some fungi.View full abstractDownload PDF (200K) -
Sankareswaran Srimurugan, Paulsamy Suresh, Balaji Babu, Salmara Ganesh ...Article type: Notes
2008 Volume 56 Issue 3 Pages 383-384
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSTritylated tetrazole of 2a underwent unusual detritylation under basic reaction condition during the synthesis of methyl ether of olmesartan medoxomil 1. The unusual detritylation was found to be a common feature in the case of all tetrazole containing Sartan molecules (3—7).View full abstractDownload PDF (106K) -
Chiy-Rong Chen, Hung-Wei Chen, Chi-I ChangArticle type: Notes
2008 Volume 56 Issue 3 Pages 385-388
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSFour new D:C-friedooleanane-type triterpenes, 3β-O-(E)-feruloyl-D:C-friedooleana-7,9(11)-dien-29-ol (1), 3β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-ol (2), 3β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (3), and methyl 2β,3β-dihydroxy-D:C-friedoolean-8-en-29-oate (6), together with five known triterpenes with the same skeleton, 3-epikarounidiol (4), 3-oxo-D:C-friedoolena-7,9(11)-dien-29-oic acid (5), bryonolol (7), bryononic acid (8), and 20-epibryonolic acid (9), were isolated from the methanol extract of the stems of Lagenaria siceraria. The structures of those compounds were elucidated using spectroscopic methods. Compounds 3 and 9 showed significant cytotoxic activity against the SK-Hep 1 cell line with IC50 values of 4.8 and 2.1 μg/ml, respectively. Based on these initially promising results, the two D:C-friedooleanane triterpenes merit further study as potential anticancer agents.View full abstractDownload PDF (86K) -
Fang Liu, Dequan Ren, De-an Guo, Yifeng Pan, Huzhe Zhang, Ping HuArticle type: Notes
2008 Volume 56 Issue 3 Pages 389-393
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSIn this paper, a new method for liquid chromatographic fingerprint of saponins in Gynostemma pentaphyllum (THUNB.) MAKINO was developed. The G. pentaphyllum powder was defatted by Soxhlet extraction with petroleum ether and then gypenosides were extracted from the residue with methanol by sonicating. Column chromatography with macro pore resin was then used to separate and enrich gypenosides. HPLC fingerprint analysis of gypenosides fraction was performed on a C18 column, with an isocratic elution of 34% acetonitrile for 60 min at 0.8 ml/min, sample injection volume was 20 μl and the wavelength was 203 nm. To cover the lack of standard compounds, the addition of an internal standard of ginsenoside Rb2 was employed in the gypenosides fingerprint profile. The relative retention time (RRT) and relative peak area (RPA) of the gypenosides peaks in the fingerprint were calculated by setting the ginsenoside Rb2 as the marker compound. The relative standard deviation (RSDs) of RRT of five common peaks vs. ginsenoside Rb2 in precision, repeatability and stability test were less than 1%, and the RSDs of RPA were less than 5%. The method validation data proved that the proposed method for the fingerprint with internal standard of G. pentaphyllum saponins is adequate, valid and applicable. Finally, three batches of crude drug samples collected from Shanxi province were tested by following the established method.View full abstractDownload PDF (466K) -
Ming-Jen Cheng, Ming-Der Wu, Ih-Sheng Chen, Gwo-Fang YuanArticle type: Notes
2008 Volume 56 Issue 3 Pages 394-397
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSThree new compounds, including two phenylacetic acid derivatives, monaspilosin (1) and monaspiloindole (2), and one pyranoindole alkaloid, monaspyranoindole (3), were isolated from the EtOAc-soluble fraction of the MeOH extract of the mycelia of Monascus pilosus BCRC 38072. Twelve known compounds were also obtained in this study. The structures were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. This is the first report of Monascus metabolites with an indole ring. All isolates were also evaluated for their scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) in TLC autographic and spectroscopic assays.View full abstractDownload PDF (119K) -
Takahiro Miyake, Keisuke Uda, Masako Kinoshita, Mikio Fujii, Hiroyuki ...Article type: Notes
2008 Volume 56 Issue 3 Pages 398-403
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSTotal syntheses of (+)-coronarin A (1), (+)-coronarin E (2), (+)-austrochaparol (3) and (+)-pacovatinin A (4) were achieved from the synthetic (+)-albicanyl acetate (6). Dess–Martin oxidation of (+)-albicanol (5) derived from the chemoenzymatic product (6) gave an aldehyde (7), which was subjected to Julia one-pot olefination using β-furylmethyl-heteroaromatic sulfones (8 or 9 ) gave (+)-trans coronarin E (2) and (+)-cis coronarin E (12) with high cis-selectivity. The synthesis of (+)-coronarin A (1) from (+)-trans coronarin E (2) was achiev-ed, while (+)-cis coronarin E (12) was converted to the natural products (+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene (13) and (+)-austrochaparol (3). By the asymmetric synthesis of (+)-3, the absolute structure of (+)-3 was determined to be 5S, 7R, 9R, 10S configurations. Homologation of (+)-albicanol (5) followed by allylic oxidation gave (7α)-hydroxy nitrile (17), which was finally converted to the natural (+)-pacovatinin A (4) in 8 steps from (+)-albicanol (5).View full abstractDownload PDF (206K) -
Motoko Oshida, Tomoaki Nakamura, Atsuo Nakazaki, Susumu KobayashiArticle type: Notes
2008 Volume 56 Issue 3 Pages 404-406
Published: March 01, 2008
Released on J-STAGE: March 01, 2008
JOURNAL FREE ACCESSA phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.View full abstractDownload PDF (138K)
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