巻号一覧
60 巻, 8 号
選択された号の論文の23件中1～23を表示しています
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Review
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Atul Awasthi, Majid Razzak, Raida Al-Kassas, Joanne Harvey, Sanjay Gar ...原稿種別: Review
2012 年 60 巻 8 号 p. 931-944
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーNaturally occurring avermectins (AVMs) and its derivatives are potent endectocide compounds, well-known for their novel mode of action against a broad range of nematode and anthropod animal parasites. In this review, chemical and pharmaceutical aspects of AVM derivatives are described including stability, synthetic and purification processes, impurities and degradation pathways, and subsequent suggestions are made to improve the chemical stability. It has been found out that unique structure of AVM molecules and presence of labile groups facilitated the derivatization of AVM into various compounds showing strong anthelmintic activity. However, the same unique structure is also responsible for labile nature related to sensitive stability profile of molecules. AVMs are found to be unstable in acidic and alkaline conditions. In addition, these compounds are sensitive to strong light, and subsequently presence of photo-isomer in animals treated topically with AVM product is well known. The pharmacoepial recommendations for addition of antioxidant into drug substance, as well as its products, arises from the fact that AVM are very sensitive to oxidation. Formations of solvates, salts, epoxides, reduction of double bonds and developing liquid formulation around pH 6.2, were some chemical approaches used to retard the degradation in AVM. This coherent review will contribute towards the better understanding of the correlation of chemical processes, stability profile and biological activity; therefore, it will help to design the shelf-life stable formulations containing AVMs.抄録全体を表示PDF形式でダウンロード (1310K)
Communication to the Editor
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Hiroshi Nagase, Satomi Imaide, Takaaki Yamada, Shigeto Hirayama, Toru ...原稿種別: Communication to the Editor
2012 年 60 巻 8 号 p. 945-948
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーOn the basis of the three-dimensional pharmacophore model of opioid κ agonists, we simplified the structure of nalfurafine (selective κ agonist) to find the essential structural moieties for binding the opioid receptors, especially κ receptor type. As a result, we found that the trans-fused decahydroisoquinoline derivatives without a phenol ring bound the opioid receptor in micromolar order and that both the amide side chain and the nitrogen substituted by the cyclopropylmethyl group were indispensable moieties for eliciting the κ selectivity. The simple decahydroisoquinoline without amide side chain also bound the opioid receptor without receptor type selectivity, suggesting that the message-address concept would be applicable to even these simple derivatives. These findings that the simple decahydroisoquinoline derivatives showed the affinities for the opioid receptors, especially some of the compounds showed κ selectivity, are the first example in the opioid field.抄録全体を表示PDF形式でダウンロード (1397K)
Regular Articles
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Takahiro Uchida, Yuka Sugino, Mai Hazekawa, Miyako Yoshida, Tamami Har ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 949-954
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーThe bitterness of 10 different products with ambroxol as active ingredient, the original and nine generics, were evaluated by human gustatory sensation tests in which the tablets were kept in the mouth, with water, at 20 and 37°C. The products all showed different bitterness intensities. The original and some of the generic products had comparatively low bitterness intensities but some of the generic products had comparatively high bitterness intensities. The bitterness intensities of these 10 was found to be significantly correlated with both the disintegration time, as evaluated using the ODT-101 (a recently developed apparatus), and the drug concentration in dissolved medium, as measured in a conventional dissolution test. The bitterness threshold of ambroxol solution was found to increase when the temperature of the water with which the tablets were taken, was raised from 20 to 37°C. The equation was calculated to predict the bitterness intensity of ambroxol, a function based on temperature and the ambroxol concentration using data from a standard ambroxol solution at 4, 20 and 37°C. The bitterness intensities obtained for the 10 ambroxol formulations with water at 20 and 37°C, coincided with the bitterness values predicted by the equation.抄録全体を表示PDF形式でダウンロード (831K) -
Piseth Khiev, Ok-Kyoung Kwon, Hyuk-Hwan Song, Sei-Ryang Oh, Kyung-Seop ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 955-961
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリー
電子付録From the stems of Dipterocarpus obtusifolius, five new triterpenes, 3-oxo-20-hydroxy-30α-methyl,17(29)α-epoxy-28-norlupane (1), 3-oxo-20-hydroxy-30β-methyl-17(29)α-epoxy-28-norlupane (2), 3,20-dioxo-28,29-norlupan-17α-ol (3), 27-demethyl-20(S)-dammar-23-ene-20-ol-3,25-dione (4), and 3-epi-cecropic acid (5) together with 13 known compounds including diterpene, sesquiterpenes and triterpenes were isolated and characterized. All isolates were tested for their cytotoxicities against a small panel of human cancer cell lines. Of the tested compounds, compounds 4–11 were found to be cytotoxic against one or more human cancer cell lines.抄録全体を表示PDF形式でダウンロード (733K) -
Ning Tang, Yoshiko Yoda, Naruhito Otani, Takayuki Kameda, Akira Toriba ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 962-966
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーTwenty-one data sets composed of readings collected by atmospheric ozone monitors worn by individuals on their clothing and installed outside their home or office were collected using Ogawa passive ozone samplers in southeastern Hyogo prefecture, Japan from September 12 to 13, 2011. The concentrations of personal and outdoor ozone ranged from not detectable to 23.2 ppb and from 4.7 to 38.3 ppb, respectively. The mean concentration of personal exposure to ozone was 3.7 ppb and was significantly lower than that of outdoor ozone (18.5 ppb). This suggests that the concentrations of outdoor ozone affect personal ozone exposure. However, in this study, we found no correlation between the concentrations of personal ozone and the total time spent outdoors or the time of day the individual was outside. In contrast, the mean concentrations of outdoor ozone were similar to those of ozone measured at the 12 nearest Ambient Monitoring Stations (AMSs). However, when the AMS was situated near a main road, the regional ozone levels were underestimated.抄録全体を表示PDF形式でダウンロード (1192K) -
Hiroko Shibata, Haruna Saito, Toru Kawanishi, Haruhiro Okuda, Chikako ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 967-975
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーGeneric versions of Neoral, a microemulsion capsule formulation of cyclosporine, have been approved worldwide. However, there are concerns about the quality and efficacy of the generics due to the formulation specificity and differences in inactive ingredients among products. In this study, we measured the physicochemical properties of both the innovator and the generic formulations, and compared their bioavailability in rats. When the capsule contents were dispersed in water, the absorbance (600 nm wavelength) of generic products was higher than that of the innovator. Whereas the dispersion solution of the innovator in Fed State Simulated Intestinal Fluid was nearly clear, that of all the generics became white and turbid. The mean diameter of the microemulsion (or emulsion) formed in water by the generics was 39.7, 57.7, 64.5, and 74.8 nm, all of which were larger than that of the innovator (26.4 nm). Although the Tmax of the generics tended to be long relative to that of the innovator, there were no significant differences between the innovator and generics with regard to maximum blood concentration (Cmax) or area under the curve (AUC). These results suggest that the physicochemical differences between the innovator and the generics will not have a significant effect on Cmax or AUC, which is necessary to ensure bioequivalence.抄録全体を表示PDF形式でダウンロード (8062K) -
Tetsuo Ogata, Atsuo Koide, Masahiro Kinoshita, Tetsuya Ozeki原稿種別: Regular Article
2012 年 60 巻 8 号 p. 976-984
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーThe aim of the present study was to mask the bitterness of propiverine hydrochloride (P-4) by converting it to propiverine free base. Fine granules comprising the free base, which was converted from P-4 by desalination, were prepared. By using Fourier transform infrared spectroscopy, thermogravimetry-differential thermal analysis, and powder X-ray diffraction spectra, we confirmed that P-4 had been converted into propiverine free base by desalination during the manufacturing process. Furthermore, the conversion into free base appeared to result in decreased solubility, and both the taste testing sensor and tasting volunteers determined that it masked the bitterness of P-4. On using the gustatory sensation test, the bitterness of the P-4 fine granules was confirmed to be weakened. The dissolution rate and bioavailability of fine granules of the free base were compared with tablets of P-4. The dissolution rate and bioavailability of the fine granules and tablets were almost the same. We successfully masked the taste of P-4 by converting it into free base using a manufacturing process that was suitable for commercial manufacturing.抄録全体を表示PDF形式でダウンロード (1557K) -
Fumihiko Ogata, Hisato Tominaga, Moe Kangawa, Kenji Inoue, Naohito Kaw ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 985-988
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーIn this study, we investigated the surface properties of granulated boehmite with vinyl acetate (G-BE20) and measured the amount of phosphate it adsorbed and the effect of contact time and solution pH on the adsorption process. The specific surface area (144.9 m2/g) and the number of surface hydroxyl groups (0.88 mmol/g) of G-BE20 were smaller than those of virgin boehmite (BE), which gave a specific surface area and number of surface hydroxyl groups of 297.0 m2/g and 1.08 mmol/g, respectively. The amount of phosphate adsorbed increased with the temperature. The isotherm model of Langmuir was used to fit experimental adsorption equilibrium data for phosphate adsorption onto G-BE20. The calculated thermodynamic parameters show the spontaneous and endothermic nature of the adsorption process. The equilibrium adsorption onto G-BE20 was reached within 16 h and the amount of phosphate adsorbed was 8.4 mg/g. The kinetic mechanism of phosphate uptake was evaluated with two different models: the Largergren pseudo first- and pseudo second-order models. The data obtained showed a better fit to the pseudo second-order model (0.991) than to the pseudo first-order model (0.967), as indicated by the r values. The rate constants for the adsorption of phosphate onto G-BE20 were calculated as 0.481 1/h and 0.029 g/mg h. The adsorption of phosphate onto G-BE20 was the maximum in the pH range 3.0–4.0.抄録全体を表示PDF形式でダウンロード (862K) -
Reiko Yutani, Shin-ya Morita, Reiko Teraoka, Shuji Kitagawa原稿種別: Regular Article
2012 年 60 巻 8 号 p. 989-994
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーAs for most other polyphenols, intradermal delivery of curcumin and resveratrol is limited; however, it was significantly improved by a microemulsion using Aerosol OT (Aerosol OT microemulsion) and Tween 80 (Tween 80 microemulsion) as surfactants. Aerosol OT microemulsion was more effective and the incorporation ratio of these polyphenols into skin by Aerosol OT microemulsion was five-fold or ten-fold that by Tween 80 microemulsion. To clarify the mechanism of the enhancement we examined the distribution of these polyphenols and the surfactant component, Aerosol OT, using excised guinea pig skin and Yucatan micropig (YMP) skin. During permeation, polyphenols distributed deep in the skin. In particular, a small molecule, resveratrol, was mainly present in the dermis in YMP skin. Aerosol OT also distributed deep in the skin. These findings suggest the possible involvement of the interaction of surfactant molecules with skin components in the enhanced delivery process of polyphenols. The distribution ratio between the dermis and epidermis of the polyphenols, including quercetin, in the presence of Aerosol OT microemulsion decreased with the increase of molecular weight in YMP skin, suggesting the possibility that distribution to the dermis is regulated by the molecular size.抄録全体を表示PDF形式でダウンロード (685K) -
Dong Li, Min Wang, Caiqin Yang, Jing Wang, Guodong Ren原稿種別: Regular Article
2012 年 60 巻 8 号 p. 995-1002
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーAzelnidipine, a new dihydropyridine calcium ion antagonist, was protected by patent in Japan. In present study, identifications of the crystal phases, including two polymorphic and a pseudopolymorphic crystal forms of azelnidipine, were attempted using powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), IR-, Raman-, THz-, and ss-NMR-spectroscopy. PXRD identified three different crystal forms, while, spectroscopy analysis provided the information of crystal structure involving intermolecular interactions. The transition thermodynamics of the azelnidipine polymorphs were extensively investigated by solubility method. The solubility of the two polymorphs of α and β in 50% ethanol at 25, 31, 37, 42, and 49°C was investigated; the values obtained were used to calculate the thermodynamic parameters of the transition reaction. The temperature of polymorphic phase transition in 50% ethanol was 50.78°C, and the values of ΔGα,βθ, ΔHα,βθ, and ΔSα,βθ at 25°C were －1.18 kJ·mol－1, －14.81 kJ·mol－1, and －45.73 J·mol－1·K－1, respectively. Form β was proved to be thermodynamic stable form at room temperature and enantiotropically related with form α. The kinetics of the solid-state decomposition, studied using DSC analysis, showed that the activation energies of decomposition of the polymorphs α and β at high temperatures were 148.67 and 151.93 kJ·mol－1.抄録全体を表示PDF形式でダウンロード (1590K) -
Chao Guo, Jun-Song Wang, Yao Zhang, Lei Yang, Peng-Ran Wang, Ling-Yi K ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1003-1010
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーA series of tirucallane triterpenoids isolated from the stem barks of Aphanamixis grandifolia were assessed for their anti-inflammatory activity, exhibiting from weak to strong anti-inflammatory activity, by testing their inhibitory effects on nitric oxide (NO) production and tumor necrosis factor-α (TNF-α) level in lipopolysaccharide (LPS) induced RAW264.7 murine macrophages. To explore the relationship between the structures and anti-inflammatory activity, a vast pool of molecular descriptors for each isolate were calculated. Genetic algorithms (GA) or simulated annealing (SA) based partial least squares (GA-PLS and SA-PLS) algorithms identified some important descriptor combinations, which were correlated with both sets of the anti-inflammatory data by partial least squares 2 (PLS2) method. S-Plot was used to visualize the descriptor influence in the PLS2 model, disclosed five most important molecular descriptors, nOHt, RDF150m, lip_violation, Mor32m and JhetZ.抄録全体を表示PDF形式でダウンロード (1040K) -
Il Kyun Lee, Sang Un Choi, Kang Ro Lee原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1011-1018
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーEleven new triterpene saponins (1–11), together with fourteen known triterpene and triterpene saponins (12–25) were isolated from a MeOH extract of Pleurospermum kamtschaticum HOFFMANN (Umbelliferae). The chemical structures of the new compounds (1–11) were determined by means of MS, 1H-NMR, 13C-NMR, correlated spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), total correlated spectroscopy (TOCSY) and nuclear Overhauser effect spectroscopy (NOESY) to be pleurosaponin A (1)–K (11). The isolated compounds were tested for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, HCT15) in vitro using the sulforhodamine B bioassay (SRB) assay. All compounds showed little cytotoxicity against tested cell lines (IC50 >30 µM).抄録全体を表示PDF形式でダウンロード (670K) -
Mostafa Mohammed Ghorab, Mansour Sulaiman Al-Said, Yassin Mohammed Nis ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1019-1028
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーN,N′-(4,4′-Sulfonylbis(4,1-phenylene))bis(2-cyanoacetamid) 2 was utilized as a key intermediate for the synthesis of novel dihydropyridines 3, 4, 8, dihydroisoquinolines 5–7, dithiolan 10, dithian 11, acrylamide 12, benzochromenes 17 and 18 and chromenopyridones 19 and 20. Compound 2 was the starting material in the synthesis of the acrylamide derivative 14, the pyrazole derivative 15 and the pyrazolopyrimidine derivative 16. All the synthesized compounds were evaluated for their in vitro anticancer activity against human breast cancer cell line (MCF7). Compound 19 showed the best cytotoxic activity with IC50 value 19.36 µM. In addition, molecular docking study of the synthesized compounds on the active sites of farnesyltransferase and arginine methyltransferase was performed in order to give a suggestion about the mechanism of action of their cytotoxic activity.抄録全体を表示PDF形式でダウンロード (3969K) -
Guo-Yuan Zhu, Blenda Chi Kwan Wong, Aiping Lu, Zhao-Xiang Bian, Ge Zha ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1029-1036
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーFrom the roots of Ardisia brevicaulis DIELS, two new alkylphenol derivatives, named ardisiphenol E (2) and F (3), have been isolated together with a known alkylphenol, ardisiphenol D (1). The structures of 1–3 were elucidated by chemical and spectroscopic techniques. Compounds 1 and 2 exhibited strong cytotoxicities on two human non-small-cell lung cancer cell lines (H1299 and A549). We found that compounds 1 and 2 upregulated mRNA and protein expressions of endoplasmic reticulum (ER) stress markers including C/EBP homologous protein (CHOP), binding immunoglobulin protein (Bip) and inositol-requiring enzyme 1 (IRE1) indicating 1 and 2 are novel natural ER stress inducers. Treatments with 1 and 5 µM of 1 or 2 triggered G1 arrest in H1299 and A549 cells with concomitant downregulation of ubiquitin fusion degradation protein 1 (Ufd1) and S-phase kinase-associated protein 2 (Skp2) proteins and the accumulation of p27, the key axes of ER stress-mediated G1 arrest. Compounds 1 and 2 also induced apoptosis at high concentrations (10, 20 µM) which was shown to be coupled with the upregulation of CHOP and Bim, the activation of caspase-9, caspase-3 and poly(ADP-ribose) polymerase (PARP) cleavage. These results indicate that compounds 1 and 2 induce ER stress that subsequently causes G1 arrest and apoptosis in human non-small-cell lung cancer cells and they may have potential anticancer effects.抄録全体を表示PDF形式でダウンロード (2159K) -
Wufu Zhu, Xin Zhai, Qiangqiang Fu, Fei Guo, Mei Bai, Jianqiang Wang, H ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1037-1045
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリー
電子付録Three series of 4-morpholinothieno[3,2-d]pyrimidine derivatives containing arylmethylene hydrazine moiety (11a–f, 13a–k and 15a–h) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (H460, HT-29, MDA-MB-231). Most of them exhibited moderate to significant cytotoxicity and high-selectivity against one or more cell lines, especially compounds 11c, 13b, 15f and 15g possessing dramatically increased cytotoxicity as compared with the positive controls, which were further evaluated for six other cancer cell lines and one normal cell line. The most promising compound 11c, bearing 3,4-methylenedioxy phenyl group, showed remarkable cytotoxicity against H460, HT-29 and MDA-MB-231 cell lines with IC50 values of 0.003 µM, 0.42 µM and 0.74 µM, which was 1.6- to 290-fold more potent than GDC-0941.抄録全体を表示PDF形式でダウンロード (925K) -
Bei Zhang, Yanfang Zhao, Xin Zhai, Lihui Wang, Jingyu Yang, Zehui Tan, ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1046-1054
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーA new series of diaryl urea derivatives bearing N-acylhydrazone moiety were designed and synthesized. All the target compounds were evaluated for their cytotoxic activities in vitro against human lung adenocarcinoma epithelial cell line (A549), human breast cancer cell line (MDA-MB-231) and human leukemia cell line (HL-60) by standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Several compounds (1a, 1f and 1h) were further evaluated against human embryonic fibroblast, lung-derived cell line (WI38). The pharmacological results indicated that some compounds exhibited promising anticancer activities. In particular, compound 1f showed the most potent cytotoxicity against the tested three cell lines with IC50 values of 0.41 µM, 0.24 µM and 0.23 µM, respectively.抄録全体を表示PDF形式でダウンロード (960K) -
Kazuya Matsuo, Hidehiko Nakagawa, Yusuke Adachi, Eri Kameda, Kazuyuki ...原稿種別: Regular Article
2012 年 60 巻 8 号 p. 1055-1062
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリー
電子付録Nitroxyl (HNO), a one-electron-reduced form of nitric oxide, has various biological activities, including a cardioprotective effect. Here, we first synthesized another, more hydrophilic photocontrollable HNO donor (3), which can release HNO in a spatially and temporally controlled manner, and then examined the properties of our series of compounds as practical HNO donors in a cellular system under photocontrol. We selected compound 2 as the preferred donor, and used it to show that calcitonin gene-related peptide (CGRP) can be upregulated in A549 cells via photocontrolled HNO release. This result demonstrates the suitability of this photocontrollable HNO donor for biological investigations.抄録全体を表示PDF形式でダウンロード (3200K)
Notes
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Albert William Garofalo, Jacek Jerzy Jagodzinski, Andrei William Konra ...原稿種別: Note
2012 年 60 巻 8 号 p. 1063-1066
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーThe preparation of novel tetrahydro-1H-pyrazolo[4,3-c]pyridines is reported. Pivotal to the synthesis of these compounds was the development of mild reaction conditions to generate a highly functionalized nitrilimine capable of undergoing an intramolecular cycloaddition with a tethered alkyne. The desired cycloadduct was formed as an equal mixture of diastereomers.抄録全体を表示PDF形式でダウンロード (859K) -
Jing Zhou, Jun-Song Wang, Yao Zhang, Peng-Ran Wang, Chao Guo, Ling-Yi ...原稿種別: Note
2012 年 60 巻 8 号 p. 1067-1071
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーOne new disesquiterpenoid (1), two new sesquiterpenoids (2, 3), were isolated from the dry flos of Chrysanthemum indicum. The structures were elucidated by spectroscopic analysis, the absolute configurations of 1 and 3, were determined by single X-ray diffraction study.抄録全体を表示PDF形式でダウンロード (1032K) -
Marlise Diane Jiofack Dongfack, Marie-Christine Lallemand, Victor Kuet ...原稿種別: Note
2012 年 60 巻 8 号 p. 1072-1075
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーFrom the methanol extract of the stem bark of Ficus exasperata, a new sphingolipid named Ficusamide, (2S,3S,4R,11E)-2-[(2′,3′-dihydroxyhexacosanoylamino)]-11-octadecene-1,3,4-triol (1), along with three known furanocoumarins, (S)-(－) oxypeucedanin hydrate (2), (R)-(+) oxypeucedanin hydrate (3), bergapten (5-methoxypsoralen) and six other known compounds, were isolated. Their structures were characterized basing on spectroscopic methods and chemical evidence. Compounds (1–3) were analyzed for their antimicrobial activity. Ficusamide (1) showed wick activity (minimal inhibitory concentration (MIC)=312.5 µg/mL) against Escherichia coli, while the furanocoumarins (2) and (3) showed significant activity (MIC=9.76 µg/mL) against Bacillus cereus, Candida albicans and Microsporum audouinii.抄録全体を表示PDF形式でダウンロード (508K) -
Machiko Ono, Xi Ying Zhao, Keisuke Kato, Hiroyuki Akita原稿種別: Note
2012 年 60 巻 8 号 p. 1076-1082
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーThe addition of 4 eq of chloral to osmundalactone (4S,5R)-4 gave quantitative formation of the hemiacetal derivative (4S,5R)-8, which was treated with methane sulfonic acid to afford the intramolecular Micheal addition product (+)-(3S,4S,5R)-9 possessing a 3,4-cis-dihydroxy-δ-lactone in 78% overall yield from (4S,5R)-4. The obtained (+)-(3S,4S,5R)-9 was subsequently converted to methyl D-digitoxoside (pyranoside) (12) in 13% overall yield and methyl D-digitoxoside (furanoside) (12) in 20% overall yield. The reaction of benzyl-osmundalactone (4R,5S)-3 and MeOH in the presence of Amberlyst A-26 as a basic catalyst gave 3,4-trans-δ-lactone (－)-(3S,4R,5S)-20 in 28% yield and 3,4-cis-δ-lactone (－)-(3R,4R,5S)-21 in 45% yield. Dibal-H reduction of (－)-(3S,4R,5S)-20 followed by catalytic hydrogenation gave L-oleandrose (6) in 86% overall yield, while Dibal-H reduction of (－)-(3R,4R,5S)-21 followed by catalytic hydrogenation provided L-cymarose (7) in 85% overall yield.抄録全体を表示PDF形式でダウンロード (953K) -
Masateru Ono, Yoshinari Takaki, Masamitsu Takatsuji, Kousuke Akiyama, ...原稿種別: Note
2012 年 60 巻 8 号 p. 1083-1087
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーThree new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1–3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring.抄録全体を表示PDF形式でダウンロード (623K) -
Yasushi Igarashi, Katsuyuki Aoki, Hiroaki Nishimura, Isao Morishita, K ...原稿種別: Note
2012 年 60 巻 8 号 p. 1088-1091
発行日: 2012/08/01
公開日: 2012/08/01
ジャーナル フリーHere, we describe the first total synthesis of hydroxyl-α- and hydroxyl-β-sanshool, which involves Suzuki–Miyaura coupling (SMC). Hydroxy-α-sanshool (1) was synthesized by SMC of bromoalkyne 4 with boronate 3 followed by (Z)-selective reduction of the triple bond in the coupling product. Hydroxy-β-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.抄録全体を表示PDF形式でダウンロード (564K)
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