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Volume 60, Issue 2
Displaying 1-20 of 20 articles from this issue
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Communication to the Editor
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Hiroaki Gouda, Yutaka Kobayashi, Takeshi Yamada, Tetsuya Ideguchi, Aki ...Article type: Communication to the Editor
2012 Volume 60 Issue 2 Pages 169-171
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESS
Supplementary materialThe three-dimensional (3D) structure of bottromycin A2, a natural anti-methicillin-resistant Staphylococcus aureus (MRSA) and anti-vancomycin-resistant Enterococci (VRE) agent consisting of seven amino acids, has been investigated through NMR spectroscopy. On the basis of 57 experimental constraints, a total of 34 converged structures were obtained. The average pairwise atomic root mean square difference is 0.74±0.59 Å for all heavy atoms. The resulting structure indicates an interesting feature in that the three C-terminal residues of bottromycin A2 fold back on the 12-membered cyclic skeleton made by the four N-terminal residues. Thus, MePro(2) and Thia-β-Ala-OMe(7), modification of which significantly affects the antibacterial activities of bottromycin A2, are located on one side of its 3D structure. These distinct structural features might be important for the binding of bottromycin A2 with the bacterial ribosome.View full abstractDownload PDF (1386K)
Regular Articles
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Naser Tavakoli, Jaleh Varshosaz, Farid Dorkoosh, Sedigheh Motaghi, Lan ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 172-177
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSAcyclovir (ACV), a model drug for this study, is one of the most effective drugs against viruses of the herpes group. Absorption of orally administered ACV is variable and incomplete, with a bioavailability of ca. 15—30%. The drug is absorbed in the duodenum after oral administration and hence, preparation of a floating drug delivery system (FDDS) for ACV may increase oral absorption of the drug. ACV matrix tablets (200 mg) containing an effervescent base (sodium bicarbonate and citric acid) and a binary combination of hydroxypropyl methylcellulose (HPMC) K4M with carbopol or sodium carboxymethyl cellulose (Na CMC) or polyvinylpyrrolidone (PVP) and/or sodium alginate were prepared by the direct compression method. The tablets were evaluated for physicochemical properties and in vitro floating ability (floating lag-time and duration), bioadhesiveness and drug release. The drug release studies were carried out in 0.1 N HCl (pH 1.2) at 37±0.5°C. At appropriate time intervals, samples were withdrawn and assayed spectrophotometrically at λmax=259 nm. The floating test showed tablets containing 15% effervescent base had a floating lag time of 10—30 s and a duration of floating time of 24 h. The formulations containing HPMC-PVP, HPMC-Na CMC, HPMC-carbopol, and HPMC-sodium alginate released about 60—90% of their drug content during a 12-h period. Increasing carbopol caused slower drug release. We concluded that the proposed tablets with 15% effervescent base, 20—30% HPMC, 30% Na CMC (and/or 20% PVP or 20% sodium alginate) showed good floating and drug release properties in vitro, and should be considered as FDDS for ACV.View full abstractDownload PDF (520K) -
Hai-Qiang Wu, Li Li, Jing Li, Zhen-Dan He, Zhi-Gang Liu, Qing-Qian Zen ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 178-182
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSThis study characterized the acaricidal activity of constituents of patchouli oil extracted from (Pogostemon cablin (Blanco) BENTH) against the house dust mite, Dermatophagoides farinae. A new compound, 2-(1,3-dihydroxy-but-2-enylidene)-6-methyl-3-oxo-heptanoic acid (DHEMH), was isolated from patchouli oil and characterized by 1H-NMR, 13C-NMR, LC-MS and elemental analysis (EA). This active component was identified as the hydrolysate of pogostone. Fifteen other constituents found in patchouli oil were also identified by GC-MS, including patchouli alcohol and pogostone. LD50 studies carried out over 24 h using contact toxicity tests identified DHEMH as the most toxic compound to D. farinae (2.04 μg/cm2), followed by patchouli oil (6.11 μg/cm2), benzyl benzoate (BP) (9.31 μg/cm2) and dibutyl phthalate (DBP) (58.52 μg/cm2). In vapor phase toxicity tests, all of these compounds were more effective in closed than open containers, indicating that the most efficient mode of delivery for these compounds is the vapor phase. These results indicate that DHEMH and patchouli oil merit further study as potential agents for the control of D. farinae.View full abstractDownload PDF (382K) -
Miho Y. Mizutani, Yoshihiro Takamatsu, Tazuko Ichinose, Akiko ItaiArticle type: Regular Article
2012 Volume 60 Issue 2 Pages 183-194
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSA fast method that can predict the binding affinities of chemicals to a target protein with a high degree of accuracy will be very useful in drug design and regulatory science. We have been developing a scoring function for affinity prediction, which can be applied to extensive protein systems, and also trying to generate a prediction scheme that specializes in each target protein, with as high a predictive power as possible. In this study, we have constructed a prediction scheme with target-specific scores for estimating ligand-binding affinities to human estrogen receptor α (ERα), considering the major conformational change between agonist- and antagonist-bound forms and the change in protonation states of histidine at the ligand-binding site. The generated scheme calibrated with fewer training compounds (23 for the agonist-bound form, 17 for the antagonist-bound form) demonstrated good predictive power (a predictive r2 of 0.83 for 154 validation compounds); this was also true for compounds with frameworks that were quite different from those of the training compounds. Our prediction scheme will be useful in drug development targeting ERα and in primary screening of endocrine disruptors, and provides a successful method of affinity prediction considering the major conformational changes in a protein.View full abstractDownload PDF (3432K) -
Jun Luo, Yi Li, Jun-Song Wang, Juan Lu, Xiao-Bing Wang, Jian-Guang Luo ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 195-204
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESS
Supplementary materialA series of novel and structurally related C-15-acyl 16-norphragmalin-type limonoids, chuktabrins C—J (1—8) and chuktabularins U-X (9—12), were isolated from the stem bark of Chukrasia tabularis var. velutina. Their structures were established on the basis of detailed spectroscopic analysis, and the absolute configuration of compound 1 was determined by a single-crystal X-ray study using a mirror CuKα radiation. Compounds 7 and 8 were unprecedent C-15-acyl 16-norphragmalins with ketonic alkyl appendage at C-15, and compounds 4 and 8 were first examples of limonoid with a characteristic carbonate moiety esterified at OH-9/OH-8 or OH-1/OH-8 respectively. A biosynthetic pathway of these limonoids was reasonably presumed based on the novel and diverse structures isolated, which provides a new insight into the plausible biosynthesis of C-15-acyl 16-norphragmalin-type limonoids. The anti-inflammatory activity of major isolates were evaluated for inhibitory activity against lipopolysaccharide (LPS) induced nitric oxide (NO) production in macrophage (RAW264.7) cell line, with IC50 value ranging from 2.40 to 16.90 μM.View full abstractDownload PDF (1060K) -
Tsutomu Warashina, Kaoru Umehara, Toshio MiyaseArticle type: Regular Article
2012 Volume 60 Issue 2 Pages 205-212
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSA MeOH extract from the roots of Taraxacum platycarpum has shown significant effects on the proliferation of normal human skin fibroblasts. Chemical analysis of the extract resulted in the isolation of 26 compounds, including eight new triterpenes, one new sesquiterpene glycoside, and seventeen known compounds. The structure of each new compound was established using NMR spectroscopy. Some triterpenes had a significant effect on the proliferation of normal human skin fibroblasts.View full abstractDownload PDF (1157K) -
Fei He, Alfarius Eko Nugroho, Chin Piow Wong, Yusuke Hirasawa, Osamu S ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 213-218
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSEight new guaipyridine sesquiterpene alkaloids, rupestines F—M (1—8) were isolated from the leaves of Artemisia rupestris and their structures were elucidated on the basis of 2D-NMR data. The absolute configurations of 1—8 have been assigned by comparison of their experimental and calculated circular dichroism (CD) spectra.View full abstractDownload PDF (788K) -
Jun Deguchi, Tomoe Hirahara, Yusuke Hirasawa, Wiwied Ekasari, Aty Widy ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 219-222
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSFour new alkaloids, cassiarins G, H, J, and K (1—4) which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from the leaves of Cassia siamea (Leguminosae) and the structures of 1—4 were elucidated by 1D- and 2D-NMR analysis and X-ray crystallographic analysis.View full abstractDownload PDF (580K) -
Susumu Watanuki, Keisuke Matsuura, Yuichi Tomura, Minoru Okada, Toshio ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 223-234
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSWe synthesized and evaluated the inhibitory activity of a series of 2-(1-alkylpiperidin-4-yl)-N-[(1R)-1-(4-fluorophenyl)-2-methylpropyl]acetamide derivatives against T-type Ca2+ channels. Structure–activity relationship studies revealed that the position of the amide structure was important for the potent inhibitory activity toward T-type Ca2+ channels. In addition, the introduction of an appropriate substituent on the pendant benzene ring played a crucial role for the selectivity towards T-type Ca2+ channels over L-type Ca2+ channels and the potent bradycardic activity of these derivatives. Oral administration of N-[(1R)-1-(4-fluorophenyl)-2-methylpropyl]-2-(1-{2-[2-(2-methoxyethoxy)phenyl]ethyl}piperidin-4-yl)acetamide (4f), which had superior selectivity for T-type Ca2+ channels over L-type Ca2+ channels, lowered blood pressure in spontaneously hypertensive rats without inducing reflex tachycardia, which is often caused by traditional L-type Ca2+ channel blockers.View full abstractDownload PDF (856K) -
Jintaek Kim, Tomohiro Kino, Hiroharu Kato, Fumihiko Yamamoto, Kohei Sa ...Article type: Regular Article
2012 Volume 60 Issue 2 Pages 235-240
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSAs a part of our efforts to develop potential imaging agents for ascorbate bioactivity, 5-O-(4-[125I]iodobenzyl)-L-ascorbic acid ([125I]1) was prepared through a two-step sequence which involved radioiodo-destannylation of a protected tributylstannyl precursor 6, followed by hydrolysis in acidic methanol of the protecting groups in 61% overall radiochemical yield, with a radiochemical purity of over 98% and a specific activity of more than 15.4 GBq/μmol. Tissue distribution of [125I]1 in tumor-bearing mice showed signs of distribution profiles similar to the reported results for 6-deoxy-6-[18F]fluoro-L-ascorbic (6-18FAsA) acid and 6-deoxy-6-[131I]iodo-L-ascorbic acid (6-131IAsA) but with notable differences in the adrenal glands, in which considerably lower uptake of radioactivity and rapid clearance with time were observed. Pretreatment of mice with a known inhibitor of ascorbate transport, sulfinpyrazone, did not produce any significant change in the adrenal uptake of radioactivity after injection of [125I]1 compared to the control, suggesting that uptake in the adrenal glands is independent of the sodium-dependent vitamin C transporter 2 transport mechanism. Introduction of a bulky substituent at C-5 on AsA, such as an iodobenzyloxy group, may not be suitable for the design of analogs that may still be able to maintain characteristic distribution properties in vivo seen with AsA itself.View full abstractDownload PDF (600K)
Notes
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Zhi-Wei Wang, Jun-Song Wang, Jun Luo, Dan-Dan Wei, Ling-Yi KongArticle type: Note
2012 Volume 60 Issue 2 Pages 241-245
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSA novel naphthalene glucoside, rheumone A (1), with an unprecedented skeleton containing a seven-membered lactone, and two new compounds, 1-O-phloroglucinyl-2-O-galloyl-6-O-cinnamoyl-β-D-glucoside (2) and chrysophanol 1-O-β-D-(6′-O-malonyl)glucoside (3), together with three known compounds (4—6) were isolated from the roots of Rheum palmatum. Their structures were elucidated mainly by spectroscopic analysis. These compounds were evaluated in vitro for their cytotoxicities towards human hepatocellular cancer cell lines Bel-7402 and Bel-7402/5Fu, and human gastric carcinoma cell line BGC-823. None of them showed cytotoxicity with IC50 far beyond 50 μM.View full abstractDownload PDF (617K) -
Phan Van Kiem, Hoang Le Tuan Anh, Nguyen Xuan Nhiem, Chau Van Minh, Ng ...Article type: Note
2012 Volume 60 Issue 2 Pages 246-250
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSThe rhizomes of Hedychium coronarium have been used for the treatment of inflammation, skin diseases, headache, and sharp pain due to rheumatism in traditional medicine. From this plant, two new labdanes, 15-methoxylabda-8(17),11E,13-trien-16,15-olide (1) and 16-methoxylabda-8(17),11E,13-trien-15,16-olide (3), named hedycoronens A and B, as well as four known, labda-8(17),11,13-trien-16,15-olide (2), 16-hydroxylabda-8(17),11,13-trien-15,16-olide (4), coronarin A (5), and corronarin E (6) were isolated. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. They were evaluated for inhibitory effects on the lipopolysaccharide (LPS)-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Among of them, compounds 1—3 were potent inhibitors of LPS-stimulated interleukin-6 (IL-6) and IL-12 p40, with IC50 ranging from 4.1±0.2 to 9.1±0.3 μM. Compounds 1 and 3 showed moderate inhibitory activity on the tumor necrosis factor-α (TNF-α) production with IC50 values of 46.0±1.3 and 12.7±0.3 μM. The remains of compounds showed inactivity. These results warrant further studies concerning the potential anti-inflammatory benefits of labdane-diterpenes from H. coronarium.View full abstractDownload PDF (571K) -
Syota Aoki, Yurika Honda, Tomoyuki Kikuchi, Takumi Miura, Ryo Sugawara ...Article type: Note
2012 Volume 60 Issue 2 Pages 251-256
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSSix new secoiridoid constituents, named isoligustrosidic acid (1), 6′-O-trans-cinnamoyl 8-epikingisidic acid (2), 6′-O-cis-cinnamoyl 8-epikingisidic acid (3), oleopolynuzhenide A (4), nuzhenals A (5) and B (6) were isolated from the dried fruits of Ligustrum lucidum AIT. Their structures were established on the basis of spectral and chemical data.View full abstractDownload PDF (701K) -
Ayano Matsushige, Yaichiro Kotake, Katsuyoshi Matsunami, Hideaki Otsuk ...Article type: Note
2012 Volume 60 Issue 2 Pages 257-259
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSAtypical Parkinsonism in the Caribbean Island Guadeloupe is thought to be associated with the consumption of plants of the Annonaceae family, especially Annona muricata (soursop). In this study, a new aporphine alkaloid named annonamine (1) was isolated from the leaves of A. muricata L. together with four known benzylisoquinoline alkaloids (2—5). The structures of the isolated compounds were elucidated by the spectroscopic method.View full abstractDownload PDF (394K) -
Tsuneyoshi Suzuki, Tomonobu Uchino, Yasunori Miyazaki, Yoshiyuki Kagaw ...Article type: Note
2012 Volume 60 Issue 2 Pages 260-266
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSCharacterization and release profiles of commercial dexamethasone dipropionate (DDP) from an innovator and 2 generic ointments (Methaderm (IM), Promethasone (GP), and Mainvate (GM)) and their admixtures with heparinoid ointment (Hirudoid Soft) were investigated. The admixtures were prepared using 2 mixing methods (slab or rotation/revolution mixer). Microscopic and FT-Raman spectrometric analyses revealed that the ointments, except for IM, contained DDP crystals. A silicone membrane was used for the evaluation of the DDP permeation. The permeated DDP amounts from GP and GM were lower than that from IM, indicating that DDP solubility in the ointment vehicle affected the release of DDP from the ointment. No significant differences were observed in DDP release between IM alone and its admixture prepared using a slab; however, DDP release from the admixture prepared using a rotation/revolution mixer was significantly lower than those from IM alone and its admixture by slab. In the GP system, DDP release from the admixtures by the 2 mixing methods was higher than that from GP alone, whereas no significant difference in DDP release between the 2 mixing methods was observed. No significant differences were observed between the GM and admixtures. The apparent solubility of DDP in the admixtures as determined by the ultracentrifugal separation method indicated that the DDP amount in the liquid phase of admixtures with GP was 6 times higher than that of admixtures with IM or GM. Therefore, the apparent solubility of DDP in the liquid phase in the GP system might influence the DDP release in admixtures.View full abstractDownload PDF (4631K) -
Koji Ochiai, Akihiko Kojima, Yasushi KohnoArticle type: Note
2012 Volume 60 Issue 2 Pages 267-269
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSAn improved method for 4,4-dimethylpyrazolone synthesis with t-butylcarbazate was described. The applicability of this method to dihydropyridazinone formation was demonstrated. This method is useful for suppressing the side reaction caused by the high nucleophilicity of hydrazine.View full abstractDownload PDF (506K) -
Ping Zhang, Yewei Yang, Xiaoliang Zheng, Wenhai Huang, Zhen Ma, Zhengr ...Article type: Note
2012 Volume 60 Issue 2 Pages 270-274
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESS
Supplementary materialAn improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a—g and the intermediate diols 4a—g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.View full abstractDownload PDF (923K) -
Akihito Yokosuka, Takeyuki Suzuki, Yoshihiro MimakiArticle type: Note
2012 Volume 60 Issue 2 Pages 275-279
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSFour new cholestane glycosides (1—4) were isolated from the leaves of Cordyline terminalis (Agavaceae). The structures of the new compounds were determined on the basis of spectroscopic analysis and a few chemical transformations followed by chromatographic and spectroscopic analyses.View full abstractDownload PDF (524K) -
Yu-Hsuan Lan, Yi-Ting Peng, Tran-Dinh Thang, Tsong-Long Hwang, Do-Ngoc ...Article type: Note
2012 Volume 60 Issue 2 Pages 280-282
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSFurther investigation of the methanolic extract of Fissistigma latifolium resulted in two new compounds whose structures were assigned as 2,5,6,7-tetramethoxyflavan (1) and 2′-hydroxy-4′,5′,6′-trimethoxybenzil (2). These two compounds were determined on the basis of chemical and spectroscopic evidences. Compound 2 is the first report of benzil from Fissistigma species. 2,5,6,7-Tetramethoxyflavan (1) showed a potent inhibitory effect on superoxide anion production in formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP)/cytochalasin B (CB)-activated human neutrophils.View full abstractDownload PDF (388K)
Errata
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Seif-Eldin Nasr Ayyad, Khalid Omar Al-Footy, Walied Mohamed Alarif, Ta ...Article type: Errata
2012 Volume 60 Issue 2 Pages 283
Published: February 01, 2012
Released on J-STAGE: February 01, 2012
JOURNAL FREE ACCESSDownload PDF (127K)
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