Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 58, Issue 10
Displaying 1-25 of 25 articles from this issue
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Review
  • Development of Responsive Lanthanide-Based Magnetic Resonance Imaging and Luminescent Probes for Biological Applications
    Kenjiro Hanaoka
    Article type: Review
    2010 Volume 58 Issue 10 Pages 1283-1294
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1283
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    Lanthanide complexes have unique chemical characteristics compared with typical organic complexes, and have recently attracted much interest because of the expanding need for new bioanalytical sensors. For example, magnetic resonance imaging (MRI) permits noninvasive three-dimensional imaging inside opaque organisms, and gadolinium ion (Gd3+) complexes have become important tools as MRI contrast agents. However, most of them are nonspecific, and report solely on anatomy. Therefore, responsive MRI contrast agents, so-called “smart” MRI contrast agents whose ability to relax water protons is greatly enhanced by recognition of a particular biomolecule, have great potential for elucidating biological phenomena. On the other hand, lanthanide complexes such as europium (Eu3+) and terbium (Tb3+) complexes have excellent luminescence properties for biological applications, i.e., long luminescence lifetime of the order of milliseconds and a large Stoke's shift of >200 nm. Their long-lived luminescence is especially suitable for time-resolved measurements, because the interference from short-lived background fluorescence and scattered light rapidly decays to a negligible level after a pulse of excitation light is applied, and the emitted light can be collected after an appropriate delay time. These luminescent lanthanide complexes have already found commercial use as highly sensitive luminescent probes in heterogeneous and homogeneous assays. This paper reviews our research on the design and synthesis of responsive lanthanide-based MRI and luminescent probes for advanced bioimaging.
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Regular Articles
  • The Relationship between the Drug Concentration Profiles in Plasma and the Drug Doses in the Colon
    Shinichiro Tajiri, Taro Kanamaru, Kazuhiro Yoshida, Yasue Hosoi, Tsuto ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1295-1300
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1295
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    After the dosing of an extended-release (ER) formulation, compounds may exist in solutions at various concentrations in the colon because the drugs are released at various speeds from the ER dosage form. The aim of this study was to investigate the relationship between the drug concentration profiles in plasma and the drug doses in the colon. Several drug solutions of different concentrations were directly administered into the ascending colon of dogs using a lubricated endoscope, and the effects of the drug dose on colonic absorption were estimated. As a result, dose-dependency of colonic absorption varied from compound to compound. Although the relative bioavailability of colonic administration of diclofenac, metformin and cevimeline compared to oral administration was similar regardless of the drug doses in the colon, colonic absorption of diltiazem varied according to the doses. From the results of the co-administration of verapamil and fexofenadine, it was clear that diltiazem underwent extensive hepatic and gastrointestinal first-pass metabolism, resulting in a low area under the curves (AUC) at a low drug dose. During the design of oral ER delivery systems, a colonic absorption study of candidate compounds should be carried out at several solutions of different drug concentrations and assessed carefully.
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  • Effects of Pathological Conditions on Ocular Pharmacokinetics of Antimicrobial Drugs
    Kayoko Ueda, Akira Ohtori, Kakuji Tojo
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1301-1305
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1301
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    A diffusion model of ocular pharmacokinetics was used to estimate the effects of pathological conditions on ocular pharmacokinetics. In vivo rabbit data after topical instillation of ciprofloxacin and ofloxacin were compared with the simulated concentrations in the aqueous and vitreous humors. The barrier capacity of the surrounding membranes such as the retina/choroid/sclera (RCS) membrane and the cornea was characterized by dimensionless Sherwood number derived by the pseudo-steady state approach (PSSA). We assumed the barrier capacity decreased by inflammation; when the barrier capacity of the RCS membrane and the cornea was assumed to be one-tenth for the RCS membrane and a half for the cornea respectively, the in vivo data agreed with the simulated profile without contradiction. The drug concentration gradient simulated in the vitreous body near the RCS membrane was more significant in the inflamed eyes than in the normal eyes, suggesting that the elimination of the drugs from the RCS membrane was enhanced by inflammation. The present diffusion model can better describe the ocular pharmacokinetics in both normal and diseased conditions.
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  • Synthesis, Characterization, Antioxidant Activities, and DNA-Binding Studies of (E)-N′-[1-(Pyridin-2-yl)ethylidene]isonicotinohydrazide and Its Pr(III) and Nd(III) Complexes
    Zhong-Yan Hao, Qi-Wan Liu, Jun Xu, Lei Jia, Shao-Bai Li
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1306-1312
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1306
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    A new ligand, (E)-N′-[1-(pyridin-2-yl)ethylidene]isonicotinohydrazide (HL), was prepared by condensation of 2-acetylpyridine and isonicotinohydrazide in ethanol. Its two lanthanide(III) complexes, [NdIII(L)2(NO3)(CH3OH)2]·CH3CH2OH (1), and [PrIII(L)2(NO3)(CH3OH)2]·CH3CH2OH (2), have been synthesized and characterized on the basis of element analyses, molar conductivities and IR spectra. The structure of complex 2 has been confirmed by X-ray diffraction. In addition, the DNA-binding properties of the two complexes have been investigated by electronic absorption spectroscopy, fluorescence spectroscopy, circular dichroic (CD) spectroscopy and viscosity measurements. The experimental results suggest that the two complexes bind to DNA via a groove binding mode, and the binding affinity of complex 2 is higher than that of complex 1. Furthermore, the antioxidant activities (superoxide and hydroxyl radical) of the ligand and its metal complexes were determined by spectrophotometry methods in vitro. These complexes were found to possess potent antioxidant activity and be superior to standard antioxidant like mannitol.
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  • Preparation and Characterization of Hydroxypropyl-β-Cyclodextrin Inclusion Complex of Eugenol: Differential Pulse Voltammetry and 1H-NMR
    Anuj Garg, Bhavna Gupta, Rajiv Prakash, Sanjay Singh
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1313-1319
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1313
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    The objective of present investigation was to improve the solubility of Eugenol by preparing the inclusion complex of Eugenol with hydroxypropyl-β-cyclodextrin (Hp-β-CD) and characterize the prepared complex by using NMR and differential pulse voltammetry (DPV). Phase solubility curve was plotted using Hp-β-CD in ranging from 0—40 mM of Hp-β-CD and found to be linear. Therefore, inclusion complex was prepared in equimolar ratio of Eugenol and Hp-β-CD by lyophilization method. Fourier transform infrared spectroscopy (FT-IR), 1H-NMR and DPV were performed for Eugenol, Hp-β-CD and prepared inclusion complex of Eugenol. 2D (two dimensional) NMR was also performed for prepared inclusion complex. The proton of phenol moiety of Eugenol experienced a pronounced chemical shift variation in 1H-NMR. The positive sign of the variation for proton in 1H-NMR indicated that the proton was located near to an oxygen atom in the Hp-β-CD cavity and its magnitude showed a strong interaction between –OH proton of Eugenol and Hp-β-CD. 2D NMR confirms the interaction between phenolic group and hydrogen atoms of Hp-β-CD. A well defined anodic peak current corresponding to oxidation of Eugenol in non-encapsulated and Hp-β-CD-Eugenol inclusion complex in phosphate buffer (pH 6.8) was obtained at about 0.35 V and 0.40 V, respectively. The positive shift in oxidation potential indicated the formation of complex via hydrophobic interactions. The oxidant power of Eugenol was retained in complex form as indicated by DPV results. Thus, its oxidation dependent pharmacological property such as antimicrobial activity is not affected after complexation with Hp-β-CD. Thus, 1H-NMR, 2D-NMR and DPV techniques can be used as valuable tools to determine the mechanism of complexation and state of electrochemical active drug in inclusion complex.
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  • Synthesis of 2-Oxo/Thioxooctahydroquinazolin-5-one Derivatives and Their Evaluation as Anticancer Agents
    Mazaahir Kidwai, Divya Bhatnagar, Rakesh Kumar, Pratibha Mehta Luthra
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1320-1323
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1320
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    An environment friendly method for the synthesis of 2-oxo/thioxooctahydroquinazolin-5-one derivatives has been devised using Ceric ammonium nitrate (CAN) as catalyst and polyethylene glycol (PEG) as solvent. The cytotoxic effect of these compounds was studied on U87 human glioma cells, compounds 4c, 4d and 4e are found to exhibit excellent activity at a concentration as low as 0.06 μg/ml.
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  • Synthesis, Cytotoxicity and Pro-apoptosis of Novel Benzoisoindolin Hydrazones as Anticancer Agents
    Yu Zhao, Jie Hui, Dan Wang, Li Zhu, Jing-Huai Fang, Xiao-Dong Zhao
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1324-1327
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1324
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    A series of benzoisoindolin hydrazones as analogues of natural lignan diphyllin were synthesized and the structures of these compounds were established by 1H-NMR, 13C-NMR, Mass and high resolution (HR)-MS. The compounds were evaluated for in vitro cytotoxicity against KB, A549 and HCT-116 cancer cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Compound 4 possessed the highest growth inhibitory effect. Significant apoptosis of HCT-116 cells treated with compound 4 was observed by Hoechst33342-propidium iodide (PI) and acridine orange (AO)-ethidium bromide (EB) staining assay. Western blot analysis disclosed that compound 4 induced apoptosis via the mitochondrial pathway accompanied by an increased expression of Bax and a decreased expression of Bcl-2.
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  • Synthesis of New 1,2,4-Triazole[3,4-b][1,3,4]thiadiazoles Bearing Pyrazole as Potent Antimicrobial Agents
    Cherkupally Sanjeeva Reddy, Lade Sanjeeva Rao, Gaddam Rajesh Kumar, Ad ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1328-1331
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1328
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    A new series of 6-(aryl/heteryl)-3-(5-methyl-1-phenyl-1H-4-pyrazolyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (7a—j) has been synthesized by the reaction of 4-amino-5-(5-methyl-1-phenyl-1H-4-pyrazolyl)-4H-1,2,4-triazol-3-yl-hydrosulfide (6) with POCl3 and the corresponding aryl/heteryl carboxylic acid, in ethanol at reflux temperature for 12 h. All the synthesized compounds were tested for in vitro activities against certain strains of bacteria such as Staphylococcus aureus, Bacillus subtilis, Escherichia coli and fungi such as Aspergillus niger, Aspergillus nodulans, Alternaria alternate. Compounds having 4-chlorophenyl (7d), 4-aminophenyl (7f), 4-nitrophenyl (7h) and 3-pyridyl (7i) substituents at 6-position of thiadiazole ring, showed marked inhibition of bacterial and fungal growth nearly equal to the standards. The other new compounds also showed appreciable activity against the test bacteria and fungi.
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  • Formulation and Physicochemical Characterization of Imwitor 308 Based Self Microemulsifying Drug Delivery Systems
    Sara Zargar-Shoshtari, Jingyuan Wen, Raid Ghassan Alany
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1332-1338
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1332
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    Self Microemulsifying Drug Delivery Systems (SMEDDS) are a novel alternative to the conventional transdermal delivery systems. SMEDDS are water-free systems, made up of oils and surfactants that can readily form a microemulsion upon dilution within an aqueous medium. Before SMEDDS can be used as a drug delivery system it is necessary to investigate the internal microstructure of the resulting microemulsion. Novel Imwitor 308 based SMEDDS were prepared and investigated. Phase behaviour of the comprising components was investigated through the construction of pseudoternary phase diagrams. The formed systems were characterized using visual inspection, measurement of electrical conductivity, viscosity and droplet size. Amongst the pseudoternary systems investigated, IPM/Cremophor EL (50% w/w)/Imwitor (50% w/w) and Myritol 318/Tween 85 (64% w/w)/ Transcutol P (20% w/w)/Imwitor (16% w/w) possessed the largest microemulsion area. Electrical conductivity and viscosity studies depict structural transitions from w/o microemulsion to bicontinuous or o/w microemulsion around 20—35% water. This was further supported by the droplet size and Fourier transform (FT)-IR measurements. The FT-IR data suggests that below the percolation threshold (φC) the water molecules are mainly bounded to the surfactant head group (bound water). Above this value, water molecule move to the outer phase of the microemulsion mainly interacting with each other though hydrogen bounding (free water). It was also found that pseudoternary systems with water content of less than 30% were stable at 32°C. Such systems may form stable microemulsion upon contact with the skin. Absorption of water may also result in a supersaturated solution with enhanced transdermal flux.
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  • Isolation of Four New Flavonoids from Melicope triphylla
    Matsutake Higa, Eisaku Nakadomari, Megumi Imamura, Kazuhito Ogihara, T ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1339-1342
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1339
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    Four new flavonoids, 3,5-dihydroxy-7,8-dimethoxy-3′,4′-methylenedioxyflavone (1), 3,5-dihydroxy-7-methoxy-3′,4′-methylenedioxyflavone (2), 3,5-dihydroxy-7-isopentenyloxy-8-methoxy-3′,4′-methylenedioxyflavone (3) and 5-hydroxy-3-isopentenyloxy-7-methoxy-3′,4′-methylenedioxyflavone (4), were isolated from the leaves of Melicope triphylla. In addition, two known flavonoids were detected including 5-hydroxy-3,7-dimethoxy-3′,4′-methylenedioxyflavone (5) and 5-hydroxy-7-isopentenyloxy-3,8-dimethoxy-3′,4′-methylenedioxyflavone (6). The structures of the new compounds were established by spectroscopic methods.
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  • Schefflerins A—G, New Triterpene Glucosides from the Leaves of Schefflera arboricola
    Zhimin Zhao, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1343-1348
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1343
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    From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Schefflera arboricola, collected in Okinawa, six new lupane glucosides, named schefflerins A—F (1—6) and one new dammarane glucoside, named schefflerin G (7), were isolated together with three known compounds, citroside A (8), and oleanane saponins, oleanolic acid (9) and echinocystic acid (10) 3-O-α-L-rhamnopyranosyl(1→4′)-O-β-D-glucuronopynosides. Their structures were elucidated through a combination of spectroscopic analyses and the structure of schefflerin F (6) was determined by X-ray crystallographic method using SPring-8 synchrotron radiation.
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  • Rhodium-Catalyzed Organothio Exchange Reaction of α-Organothioketones with Disulfides
    Mieko Arisawa, Fumihiko Toriyama, Masahiko Yamaguchi
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1349-1352
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1349
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    RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.
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  • Kojic Acid Derivatives as Histamine H3 Receptor Ligands
    Kerstin Sander, Tim Kottke, Lilia Weizel, Holger Stark
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1353-1361
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1353
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    The histamine H3 receptor (H3R) is a promising target in the development of new compounds for the treatment of mainly centrally occurring diseases. However, emerging novel therapeutic concepts have been introduced and some indications in the H3R field, e.g. migraine, pain or allergic rhinitis, might take advantage of peripherally acting ligands. In this work, kojic acid-derived structural elements were inserted into a well established H3R antagonist/inverse agonist scaffold to investigate the bioisosteric potential of γ-pyranones with respect to the different moieties of the H3R pharmacophore. The most affine compounds showed receptor binding in the low nanomolar concentration range. Evaluation and comparison of kojic acid-containing ligands and their corresponding phenyl analogues (3—7) revealed that the newly integrated scaffold greatly influences chemical properties (S Log P, topological polar surface area (tPSA)) and hence, potentially modifies the pharmacokinetic profile of the different derivatives. Benzyl-1-(4-(3-(piperidin-1-yl)propoxy)phenyl)methanamine ligands 3 and 4 belong to the centrally acting diamine-based class of H3R antagonist/inverse agonist, whereas kojic acid analogues 6 and 7 might act peripherally. The latter compounds state promising lead structures in the development of H3R ligands with a modified profile of action.
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  • Carotenoids and Related Polyenes, Part 12
    First Total Synthesis and Absolute Configuration of 3′-Deoxycapsanthin and 3,4-Didehydroxy-3′-deoxycapsanthin
    Yumiko Yamano, Mahankhali Venu Chary, Akimori Wada
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1362-1365
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1362
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    The synthesis of 3′-deoxycapsanthin (1) and 3,4-didehydroxy-3′-deoxycapsanthin (2), carotenoids of paprika, has been achieved by employing Lewis acid-promoted regio- and stereoselective rearrangement of the C15-epoxy dienal 5a. The absolute stereochemistry of the newly formed C-5 chiral center of rearrangement product 6a was determined to be (R) from its alternative synthesis derived from (+)-(R)-camphonanic acid (11).
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  • Calculating Critical Relative Humidity from Solubility According to Pitzer Ion Interaction Model
    Chaoqun Xiang, Yingli Wang, Xiancheng Zhan, Lin Luo, Linli Li, Chengro ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1366-1368
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1366
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    The solubility and the critical relative humidity (Hcr) of 14 drugs and inorganic salts were determined, the relationship between the Hcr and the solubility was explored theoretically, and the Hcr was calculated in the light of Raoult's law and Pitzer ion interaction model from their solubility. The results indicate that the Hcr values calculated by Raoult's law in high humidity (Hcr>80%) and by Pitzer ion interaction model in low humidity (Hcr<80%) are comparable to the measured ones.
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  • Chemical Constituents in the Leaves of Vateria indica
    Tetsuro Ito, Yuichi Masuda, Naohito Abe, Masayoshi Oyama, Ryuichi Sawa ...
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1369-1378
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1369
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    Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C2-symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolute structures were elucidated by spectroscopic analysis, including two dimensional NMR and circular dichroism (CD) spectra.
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  • Structures of Novel Norstilbene Dimer, Longusone A, and Three New Stilbene Dimers, Longusols A, B, and C, with Antiallergic and Radical Scavenging Activities from Egyptian Natural Medicine Cyperus longus
    Toshio Morikawa, Fengming Xu, Hisashi Matsuda, Masayuki Yoshikawa
    Article type: Regular Article
    2010 Volume 58 Issue 10 Pages 1379-1385
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1379
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    The methanolic extract of the whole plant of Cyperus longus originating in Egypt was found to show antiallergic effect on ear passive cutaneous anaphylaxis reactions in mice. By bioassay-guided separation, 11 stilbenes and stilbene dimers including a novel norstilbene dimer, longusone A, and three new stilbene dimers, longusols A, B, and C, were isolated. Their structures were elucidated on the basis of chemical and physicochemical evidence. Among the isolates, longusol B (IC50=96 μM), luteolin (3.0 μM), resveratrol (17 μM), piceatannol (24 μM), and cassigarols E (84 μM) and G (84 μM) were found to inhibit the release of β-hexosaminidase, as a marker of antigen-induced degranulations, in rat basophilic leukemia (RBL-2H3) cells. In addition, the methanolic extract and the constituents showed 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (SC50=22 μg/ml and 2.8—29 μM, respectively).
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Notes
  • Conformational Analysis of β-1,2-Linked Mannobiose to Mannoheptaose, Specific Antigen of Pathogenic Yeast Candida albicans
    Nobuyuki Shibata, Yoshio Okawa
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1386-1390
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1386
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    Candida albicans contains characteristic β-1,2-linked oligomannosyl moieties in the cell wall mannan. Reduction of the reducing termini of these oligosaccharides by NaBH4 causes a significant downfield shift in the NMR signals for the second and third mannose units and upfield shift of the fourth mannose unit. To show the correlation between the shift in the NMR signals and the conformations of the β-1,2-linked mannooligosaccharides, we performed molecular mechanics calculations. Six energy minima of the β-1,2-linked mannobiose were found in the relaxed map computed using the AMBER force field. Five of the six energy minima could also be generated by a simulated annealing from a 900 K molecular dynamics. Similarly, the solution conformation of the β-1,2-linked mannotriose to mannoheptaose was identified by the high temperature-simulated annealing. In the mannotetraose, the nonreducing terminal mannose unit was located near the reducing terminal one and formed a folded conformation. This result suggests that a mannose unit affects the H-1 chemical shifts of not only the second mannose unit, but also the third and fourth mannose units.
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  • A Novel Cyclopentene Derivative and a Polyhydroxylated Steroid from a South China Sea Gorgonian Menella sp.
    Xing-Yun Chai, Jian-Fan Sun, Li-Ying Tang, Xian-Wen Yang, Yun-Qiu Li, ...
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1391-1394
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1391
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    A chemical investigation on a South China Sea gorgonian, Menella sp. resulted in the isolation and elucidation of menellin A (1), a highly oxygenated racemate with C8 skeleton, and a polyhydroxylated steroid, menellsteroid C (2), along with eight known compounds (3—10). The structures of the new compounds were elucidated by means of MS, 1D and 2D NMR spectra, and the relative stereochemistry of 1 was determined by X-ray single-crystal diffraction analysis. In addition, compound 7 was isolated as a new natural product. Compounds 1—3 and 7 were selected to test the anti-inflammatory inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 1 and 3 exhibited modest inhibitory effects with IC50 of 71.3, 33.9 μM, respectively, compared to the positive control aminoguanidine (IC50 25.0 μM).
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  • Two New Flavan-Flavanones from Sarcandra hainanensis
    Cong-Mei Cao, Li-Jia Xu, Yong Peng, Qing-Wen Shi, Pei-Gen Xiao
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1395-1398
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1395
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    Chemical study of the whole plants of Sarcandra hainanensis yielded two new biflavonoids with a flavan-flavanone skeleton, sarcandrone C (1), D (2) and 6 known compounds (3—8). Structures were elucidated on the basis of NMR spectroscopic methods.
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  • Reinvestigation of the Absolute Stereochemistry of Megastigmane Glucoside, Icariside B5
    Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio Takeda, Toshio Miyase
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1399-1402
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1399
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    Icariside B5 is one of the widely distributed megastigmane glucosides among plant sources. The absolute structure of icariside B5 was reinvestigated by chemical conversion from the related compound and the application of the modified Mosher's method. As a result, the structure of icariside B5 was revised to be (6S,9S)-6,9-dihydroxymegastigman-4-en-3-one 9-O-β-D-glucopyranoside.
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  • Iridoid and Acyclic Monoterpene Glycosides, Kankanosides L, M, N, O, and P from Cistanche tubulosa
    Toshio Morikawa, Yingni Pan, Kiyofumi Ninomiya, Katsuya Imura, Dan Yua ...
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1403-1407
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1403
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    Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.
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  • A New Monoterpenoid Glycoside from Myrica esculenta and the Inhibition of Angiotensin I-Converting Enzyme
    Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Bui Huu Tai, Nguyen X ...
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1408-1410
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1408
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    One new monoterpenoid glycoside, myresculoside (1), and eleven known compounds, were isolated from methanol extract of Myrica esculenta leaves by repeated column chromatography. The effects of these compounds on angiotensin I-converting enzyme (ACE) inhibition were investigated. Compounds 3 and 4 showed the most potent ACE inhibition with rates of 29.97% and 25.63% at concentration of 100 μM, respectively. Compounds 5, 6, and 11 showed weak activity with inhibitory rates of 0.07—1.41% at concentration of 100 μM.
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  • Nucleophilic Addition to 2,3-Disubstituted Butanal Derivatives and Their Application to Natural Product Synthesis
    Hidekazu Horie, Hideaki Akaike, Keisuke Kato, Hiroyuki Akita
    Article type: Note
    2010 Volume 58 Issue 10 Pages 1411-1418
    Published: October 01, 2010
    Released on J-STAGE: October 01, 2010
    DOIhttps://doi.org/10.1248/cpb.58.1411
    JOURNAL FREE ACCESS
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    The reaction of 2,3-anti-2-tert-butyldimethylsiloxy-3-substituted butanal derivative [anti-B, (±)-10 and (±)-16] derived from trans-(2,3)-epoxy butanoate (1) with carbon nucleophiles [α-furyl anion, acetate anion, and indium (In)-assisted allyl anion] has been investigated to give selectively the anti-, anti-adduct D. This anti-stereoselection could be explained by the Felkin–Anh transition state model. Thus obtained anti-, anti-adducts (±)-17 and (±)-38 were formally converted to natural products, (±)-asperlin (2) and (±)-olivose (4), respectively. The major anti-, anti-adduct (±)-26 was converted to (±)-digitoxose (3), while the minor anti-, syn-adduct (±)-27 was also converted to (±)-olivose (4). The reaction of (±)-10 with tert-butyl acetate anion gave predominantly afforded the anti-, anti-adduct (±)-23, which was converted to (±)-1,5-dideoxyhexitol (25). Alternately, the reaction of 2,3-syn-2-tert-butyldimethylsiloxy-3-p-methoxyphenoxy butanal derivative [syn-B, (±)-14] derived from trans-(2,3)-epoxy butanoate (1) with carbon nucleophile (In-assisted allyl anion) afforded a ca. 1 : 1 mixture of the syn-, anti-adduct E [(±)-32 or (±)-34] and syn-, syn-adduct F [(±)-33 or (±)-35]. After separation of this mixture, (±)-34 and (±)-35 were separately converted to (±)-oliose (5) and (±)-boivinose (6), respectively.
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