Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 59, Issue 1
Displaying 1-25 of 25 articles from this issue
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Review
  • Development of Atom-Economical Catalytic Asymmetric Reactions under Proton Transfer Conditions: Construction of Tetrasubstituted Stereogenic Centers and Their Application to Therapeutics
    Naoya Kumagai
    Article type: Review
    2011 Volume 59 Issue 1 Pages 1-22
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.1
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    The development of atom-economical catalytic asymmetric reactions based on two distinct sets of catalyst, a rare earth metal/amide-based ligand catalyst and a soft Lewis acid/hard Brønsted base catalyst, is reviewed. These catalytic systems exhibit high catalytic activity and stereoselectivity by harnessing a cooperative catalysis through hydrogen bond/metal coordination and soft–soft interactions/hard–hard interactions, respectively. The effectiveness of these cooperative catalysts is clearly delineated by the high stereoselectivity in reactions with highly coordinative substrates, and the specific activation of otherwise low-reactive pronucleophiles under proton transfer conditions. The rare earth metal/amide-based ligand catalyst was successfully applied to catalytic asymmetric aminations, nitroaldol (Henry) reactions, Mannich-type reactions, and conjugate addition reactions, generating stereogenic tetrasubstituted centers. Catalytic asymmetric amination and anti-selective catalytic asymmetric nitroaldol reactions were successfully applied to the efficient enantioselective synthesis of therapeutic candidates, such as AS-3201 and the β3-adrenoreceptor agonist, showcasing the practical utility of the present protocols. The soft Lewis acid/hard Brønsted base cooperative catalyst was specifically developed for the chemoselective activation of soft Lewis basic allylic cyanides and thioamides, which are otherwise low-reactive pronucleophiles. The cooperative action of the catalyst allowed for efficient catalytic generation of active carbon nucleophiles in situ, which were integrated into subsequent enantioselective additions to carbonyl-type electrophiles.
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Regular Articles
  • The C-Glucosyl Bond of Puerarin Was Cleaved Hydrolytically by a Human Intestinal Bacterium Strain PUE to Yield Its Aglycone Daidzein and an Intact Glucose
    Kenichi Nakamura, Tomohiro Nishihata, Jong-Sik Jin, Chao-Mei Ma, Katsu ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 23-27
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.23
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    C-Glycosides are usually resistant against acidic hydrolysis and enzymatic treatments because C-1 of the sugar moiety is directly attached to the aglycone by C–C bonding. Nevertheless, a human intestinal bacterium, strain PUE, can cleave the C-glucosyl bond of puerarin to yield its aglycone daidzein. To clarify the mechanism of the cleaving reaction, we tried to identify the structure of the metabolite derived from the sugar moiety of puerarin. To detect it easily, deuterium labeled puerarin, [6″,6″-D2]puerarin, was prepared in 7 steps. Sugars contained in a metabolite mixture from [6″,6″-D2]puerarin was analyzed by an HPLC-electrospray ionization (ESI)-MS method after treatment of sugars with 1-phenyl-3-methyl-5-pyrazolone (PMP). Since deuterium labeled glucose was detected in the metabolite mixture of [6″,6″-D2]puerarin, we concluded that puerarin was metabolized to daidzein and an intact glucose by strain PUE. As C-1 of the sugar was hydroxylated instead of hydrogenating, C-glucosyl bond-cleaving reaction is not reduction but hydrolysis. This is the first report of revealing the reaction manner and the exact products of C-glucosyl bond-cleaving reaction.
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  • Analysis of the Essential Oils of Coriandrum sativum Using GC-MS Coupled with Chemometric Resolution Methods
    Zhi-Feng Zhou, Ling-Yun Chen, Mei Shen, An-De Ma, Xue-Mei Yang, Fei Zo ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 28-34
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.28
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    The essential oils extracted from Coriandrum sativum L. were analyzed by GC-MS coupled with chemometric resolution methods. Through the chemometric resolution methods, peak clusters were uniquely resolved into the pure chromatographic profiles and mass spectra of each component. Qualitative analysis was performed by comparing the pure mass spectra with those in the NIST 05 mass spectral library. Quantitative analysis was performed using the total volume integration method. A total of 118 constituents were detected, of which 104 were identified, accounting for 97.27% of the total content. The results indicate that GC-MS combined with chemometric resolution methods can greatly enhance the capability of separation and the reliability of qualitative and quantitative results. The combined method is an economical and accurate approach for the rapid analysis of the complex essential oil samples in Coriandrum sativum L.
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  • Artificial Neural Network Combined with Principal Component Analysis for Resolution of Complex Pharmaceutical Formulations
    Giuseppina Ioele, Michele De Luca, Erdal Dinç, Filomena Oliveri ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 35-40
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.35
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    A chemometric approach based on the combined use of the principal component analysis (PCA) and artificial neural network (ANN) was developed for the multicomponent determination of caffeine (CAF), mepyramine (MEP), phenylpropanolamine (PPA) and pheniramine (PNA) in their pharmaceutical preparations without any chemical separation. The predictive ability of the ANN method was compared with the classical linear regression method Partial Least Squares 2 (PLS2). The UV spectral data between 220 and 300 nm of a training set of sixteen quaternary mixtures were processed by PCA to reduce the dimensions of input data and eliminate the noise coming from instrumentation. Several spectral ranges and different numbers of principal components (PCs) were tested to find the PCA-ANN and PLS2 models reaching the best determination results. A two layer ANN, using the first four PCs, was used with log-sigmoid transfer function in first hidden layer and linear transfer function in output layer. Standard error of prediction (SEP) was adopted to assess the predictive accuracy of the models when subjected to external validation. PCA-ANN showed better prediction ability in the determination of PPA and PNA in synthetic samples with added excipients and pharmaceutical formulations. Since both components are characterized by low absorptivity, the better performance of PCA-ANN was ascribed to the ability in considering all non-linear information from noise or interfering excipients.
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  • Design and Characterization of Nanocrystal Formulations Containing Ezetimibe
    Tugba Gulsun, Reyhan Neslihan Gursoy, Levent Oner
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 41-45
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.41
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    Ezetimibe is a lipid-lowering compound that selectively inhibits the absorption of cholesterol and related phytosterols from the intestine. As ezetimibe is almost insoluble in water, its bioavailability is too low to be detected. Thus, the objective of this study was to improve the solubility and dissolution rate of ezetimibe by preparing drug nanocrystals utilizing ball milling, high speed homogenization techniques. Pluronic F127 was chosen as a surface modifier to stabilize the nanocrystal formulations. Nanocrystal formulations of ezetimibe were prepared by using ball milling and high speed homogenization techniques. Additionally, the physicochemical characteristics of ezetimibe and nanocrystal formulations were determined by Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), X-ray analysis and particle size analysis. Tablets were prepared containing ezetimibe nanocrystals formed by high speed homogenization (ultrasonic) and ball milling according to the results of particle size measurements and in vitro dissolution rates of the nanocrystal formulations. As a result of these experiments, it was found that the dissolution rate of the nanocrystal formulations increased and although tablet formulations which did not contain any solubilizing agent like sodium lauryl sulfate (SDS), the dissolution profile of these formulations were found similar to the commercial product.
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  • Identification of Cyclicsulfonamide Derivatives with an Acetamide Group as 11β-Hydroxysteroid Dehydrogenase 1 Inhibitors
    Se Hoan Kim, Sung Wook Kwon, So Young Chu, Jae Hong Lee, Banda Narsaia ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 46-52
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.46
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    In the continuation of our 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor research, cyclic sulfonamide derivatives with an acetamide group at the 2-position were synthesized and evaluated for their abilities to inhibit 11β-HSD1. Among this series, Compound 34 showed good in vitro activity toward human 11β-HSD1, selectivity against 11β-HSD2, microsomal stability, good pharmacokinetic and safety profiles human ether-a-go-go related gene (hERG and cytochrome P450 (CYP)). Also, a docking study explained the activity difference between human and mouse 11β-HSD1.
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  • Three Steroids with Unique Structural Feature of 5β-Spirostan-1β,3β,17α-trihydroxyl from Reineckia carnea
    Zhong-Quan Zhang, Jian-Chao Chen, Jian Yan, Ming-Hua Qiu
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 53-56
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.53
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    A new spirostanol sapogenin and two spirostanol saponins, tentatively named reineckiagenin A (1), reineckiagenoside A (2), and reineckiagenoside B (3), were isolated from the whole plant of Reineckia carnea. By detailed analysis of their 1D and 2D NMR spectra, chemical methods, and by comparison with spectra data of known compounds, the structures of the new steroids were determined to be 25(S)-5β-spirostan-1β,3β,17α-triol (1), 25(S)-5β-spirostan-1β,3β,17α-triol 1-O-β-D-xylopyranoside (2), 25(S)-5β-spirostan-1β,3β,17α-triol 1-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (3). Compounds 1, 2, and 3 are the first naturally occurring steroids with unique structural feature of 5β-spirostan-1β,3β,17α-trihydroxyl.
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  • Study of the Pseudo-Crystalline Transformation from Form I to Form II of Thiamine Hydrochloride (Vitamin B1)
    Katsuhiko Masuda, Takayuki Ishige, Hiroyuki Yamada, Kotaro Fujii, Hide ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 57-62
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.57
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    The purpose of the current study was to evaluate the rate of the pseudo-crystalline transformation of thiamine hydrochloride form I to form II depending on the temperature and humidity. Changes in the appearance and weight of form I crystals were observed under humidified conditions using a water vapor sorption system equipped with a CCD camera. The form I crystals and tablets were stored under various temperature and humidity conditions (the saturation salt desiccator method), and the pseudo-crystalline transformation was observed using X-ray powder diffractometry with our laboratory equipment for drug substances and using synchrotron X-ray powder diffractometry for tablets. It was confirmed that the activation energy in the pseudo-crystalline transformation rate from form I to form II was dependent on humidity, and the calculated values were 121—155 kJ/mol at 70—90% relative humidity. Moreover, when thiamine hydrochloride was formulated as tablets, it was confirmed that the transformation rate was slower compared with the drug substances alone. The pseudo-crystalline transformation rate therefore declined after formulation in tablet form, perhaps due to the shielding effects of thiamine hydrochloride crystal from contact with water molecules by excipients, compaction, etc.
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  • Drug pH-Sensitive Release in Vitro and Targeting Ability of Polyamidoamine Dendrimer Complexes for Tumor Cells
    Dan Liu, Haiyang Hu, Jie Zhang, Xiuli Zhao, Xing Tang, Dawei Chen
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 63-71
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.63
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    Recently, dendrimers have been widely used in medical applications such as drug delivery and gene transfection. In this study, a pH-sensitive diblock copolymer of poly(methacryloyl sulfadimethoxine) (PSD) and polyethylene glycol (PEG) modified by lactose (LA-PEG-b-PSD) was synthesized. The pKa value of the LA-PEG-b-PSD was also measured. Then, polyamidoamine (PAMAM) complexes were prepared with PAMAM (G4.0) and LA-PEG-b-PSD by electrostatic interaction. To investigate drug pH-sensitive release in vitro, doxorubicin (DOX) was loaded in PAMAM. A higher drug cumulative release from LA-PEG-b-PSD/PAMAM complexes in phosphate buffered saline (PBS) was found at pH 6.5 than at pH 7.4. The cytotoxicity and cellular uptake of PAMAM complexes were investigated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and confocal microscopy. LA-PEG-b-PSD/PAMAM/DOX complexes were able to enhance the cytotoxicity of DOX against HepG2 cells at pH 7.4. Confocal microscopy showed a higher cellular uptake of PEG-b-PSD/PAMAM complexes at pH 6.5. PAMAM complexes modified by lactose showed a higher affinity for hepatic cancer cells than those without lactose at pH 7.4. These results suggest that LA-PEG-b-PSD/PAMAM complexes exhibit selective targeting and cytotoxicity against HepG2 cells. In vivo antitumor studies showed that the LA-PEG-b-PSD/PAMAM/DOX complexes displayed higher antitumor efficacy compared with non-targeted PAMAM/DOX and DOX solution. These results indicate that this strategy should be applicable to the treatment of liver cancers.
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  • Tricalysionoside A, a Megastigmane Gentiobioside, Sulfatricalysines A—F, and Tricalysiosides X—Z, ent-Kaurane Glucosides, from the Leaves of Tricalysia dubia
    Junko Shitamoto, Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuk ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 72-77
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.72
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    Further isolation work on the water-soluble fraction of a MeOH extract of Tricalysia dubia afforded one new megastigmane gentiobioside, named tricalysionoside A (1), and three sulfates, named sulfatricalysines A—C (2—4). Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of T. dubia yielded sulfatricalysines D—F (5—7) and three new ent-kaurane glucosides, named tricalysiosides X—Z (8—10). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute stereochemistry of tricalysionoside A (1) was established by modified Mosher's method.
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  • Asterosaponins Isolated from the Starfish Asterias amurensis
    In Hyun Hwang, Dong Woo Kim, Su Jeong Kim, Byung Sun Min, Seung Ho Lee ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 78-83
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.78
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    Three new asterosaponins 1—3 and four known saponins 4—7 have been isolated from the starfish Asterias amurensis LÜTKEN. By means of high magnetic field 1D- and 2D-NMR (1H–1H correlation spectroscopy (COSY), total correlation spectroscopy (TOCSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser effect spectroscopy (NOESY)) and MS analyses, the chemical structures of new compounds were determined to be 6α-O-[β-D-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→3)-β-D-galactopyranosyl]-5α-chol-9(11)-en-23-one-3β-yl sodium sulfate (1), 6α-O-[β-D-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→3)-β-D-galactopyranosyl]-5α-cholesta-9(11),24-dien-23-one-3β-yl sodium sulfate (2), and 6α-O-[β-D-fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→3)-β-D-galactopyranosyl]-5α-cholest-9(11)-en-23-one-3β-yl sodium sulfate (3). In addition, the NMR data for known saponins 4—7 were completely assigned by extensive 2D-NMR analysis without chemical degradation.
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  • Development of Bioluminescent Enzyme Immunoassay for S-Equol Using Firefly Luciferase and Its Application to the Assessment of Equol-Producer Status
    Takayuki Minekawa, Akira Kambegawa, Kumiko Shindome, Hiroshi Ohkuma, K ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 84-87
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.84
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    In this study, we developed a specific bioluminescent enzyme immunoassay (BLEIA) for S-equol, employing firefly luciferase as a labeling enzyme, as an alternative to HPLC methods. Satisfactory correlation (r=0.992) was shown when this S-equol BLEIA was compared with HPLC. The cross-reactivity with R-equol as its diastereoisomer is <5%, and that with daidzein, which is the substrate of equol, is 0.02%. Frequencies of Japanese equol producers determined using two distinct approaches were compared: a threshold value for urinary S-equol concentration of 232 ng/ml gave frequencies of 32% of men and 19% of women. These values correspond to the results for log10-transformed urinary S-equol to daidzein ratio threshold of −1.75, namely, 34% of men and 19% of women. When the changes in concentration of urinary equol and daidzein were measured after ingestion of isoflavone, the maximum concentration (Cmax) of urinary equol appeared after 9.6 h of isoflavone consumption; this Cmax was 2 h later than that for daidzein. The S-equol BLEIA documented in this study is expected to be an important tool for the assessment of equol producer status and demonstration of the bioavailability of isoflavone.
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  • Hyaluronidase Inhibitory Rosmarinic Acid Derivatives from Meehania urticifolia
    Toshihiro Murata, Toshio Miyase, Fumihiko Yoshizaki
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 88-95
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.88
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    Nine new phenylpropanoids, rashomonic acids A—D (1—4) and meehaniosides A—E (5—9), along with four known compounds were isolated from Meehania urticifolia. The structure of each new compound was elucidated based on the results of spectroscopic analyses. Compounds 3—8 showed moderate hyaluronidase inhibitory activity with IC50 values of 183—1049 μM.
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  • Synthesis and Blocking Activities of Isoindolinone- and Isobenzofuranone-Containing Phenoxylalkylamines as Potent α1-Adrenoceptor Antagonists
    Shou-Hua Zhang, Chun-Ye Wang, Zhen-Zhou Jiang, Pei-Zhou Ni, Jin-Pei Zh ...
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 96-99
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.96
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    This paper describes the synthesis and blocking activities of twelve new isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α1-Adrenoceptor antagonists. These compounds were synthesized in moderate to good yields starting from 3,4-dimethylphenol, and characterized with 1H-NMR, MS, IR and elemental analysis. Their blocking activities toward α1-Adrenoceptors were evaluated on isolated rat anococcygeus muscles. The results indicated that these compounds were very strong in blocking α1-Adrenoceptors, and most of them exhibited activities that were comparable to that of known potent α1-Adrenoceptor antagonist 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH).
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  • Stereochemical Structure and Intermolecular Interaction of Complexes of (−)-Gallocatechin-3-O-gallate and Caffeine
    Hiroyuki Tsutsumi, Takashi Sato, Takashi Ishizu
    Article type: Regular Article
    2011 Volume 59 Issue 1 Pages 100-105
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.100
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    A suspension containing an equimolecular amount of (−)-gallocatechin-3-O-gallate (GCg) and caffeine in water was heated at 90 °C for 30 min to give a 1 : 2 complex of GCg and caffeine. X-Ray crystallographic analysis of crystal of the 1 : 2 complex showed that π–π interactions formed between the A, B′ rings of GCg and the two six-membered rings of caffeine. Whereas, the same suspension was heated at 90 °C for 30 s to give a sticky substance, which contained GCg, caffeine, and water at a molar ratio of 1 : 1 : 22 based on measurement of the integral volume of 1H-NMR signals. The sticky substance crystallized slowly to give a 2 : 2 complex of GCg and caffeine. X-Ray crystallographic analysis of crystal of the 2 : 2 complex showed that the A and C rings of GCg moieties faced each other, and face-to-face π–π interactions formed between the B ring of GCg and caffeine, the B′ ring of GCg and caffeine.
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Notes
  • New Diketopiperazine Derivatives Isolated from Sea Urchin-Derived Bacillus sp.
    Ken Yonezawa, Koji Yamada, Isao Kouno
    Article type: Note
    2011 Volume 59 Issue 1 Pages 106-108
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.106
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    Two new diketopiperazine derivatives, bacillusamides A (1) and B (2), have been isolated from the EtOAc extract of the sea urchin-derived Bacillus sp. along with the known cyclo(-L-pro-L-val-) (3), cyclo(-L-pro-L-tyr-) (4), cyclo(-L-pro-L-phe-) (5). These structures were elucidated by extensive spectroscopic methods. Furthermore, the absolute configurations of the amino acid residues were determined using Marfey's method. Compound 1 displayed weak antifungal activity against Aspergillus niger.
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  • Pep-1 Peptide-Modified Liposomal Carriers for Intracellular Delivery of Gold Nanoparticles
    Myung Joo Kang, Sangyeop Lee, Bo Kyun Kim, Jae Yoon Eum, Sang Han Park ...
    Article type: Note
    2011 Volume 59 Issue 1 Pages 109-112
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.109
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    A Pep-1 peptide-modified liposomal (Pep1-Lipo) carrier system was investigated to increase the intracellular delivery of gold nanoparticles (Au NPs). Au NPs with a mean diameter of 13 nm were successfully encapsulated into the inner aqueous compartment of the novel carrier using an ethanol injection technique, reserving the distinctive optical characteristics of the surface plasmon resonance peak around 530 nm. The Au NP-loaded liposomal carrier was physically characterized as 150—170 nm in size and 45 mV in zeta potential. Dark field microscopic observation demonstrated that in vitro cellular association and/or translocation of the nanoprobes into the cells was increased by Pep1-Lipo carriers compared to bare Au NPs. In conclusion, this novel liposomal formulation is a promising platform for the intracellular delivery of metallic nanoprobes including Au NPs.
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  • Ficusmicrochlorin A—C, Two New Methoxy Lactone Chlorins and an Anhydride Chlorin from the Leaves of Ficus microcarpa
    Huan-You Lin, Hsi-Lin Chiu, Te-Ling Lu, Chih-Ying Tzeng, Tzong-Huei Le ...
    Article type: Note
    2011 Volume 59 Issue 1 Pages 113-116
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.113
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    Two new methoxy lactone chlorins ficusmicrochlorin A (1) and ficusmicrochlorin B (2), and one new anhydride chlorin ficusmicrochlorin C (3), along with eight known pheophytins were isolated from the leaves of Ficus microcarpa. Their structures were determined by the extensive 1D- and 2D-NMR techniques. New pheophytin compound was rarely obtained from natural sources. In the past ten years, only three new natural pheophytins were characterized.
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  • Tigloylshikonin, a New Minor Shikonin Derivative, from the Roots and the Commercial Root Extract of Lithospermum erythrorhizon
    Yusai Ito, Kenichi Onobori, Takeshi Yamazaki, Yoko Kawamura
    Article type: Note
    2011 Volume 59 Issue 1 Pages 117-119
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.117
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    Tigloylshikonin, a new shikonin derivative esterified with tiglic acid ((E)-2-methylbut-2-enoic acid), was isolated as a minor pigment from a food colorant “Shikon color,” a commercial root extract from Lithospermum erythrorhizon SIEBOLD et ZUCCARINI. The structure of tigloylshikonin was elucidated using 1H, 13C, the difference nuclear Overhauser effect (NOE), and 2D NMR techniques. Its stereochemistry was determined by chiral-phase HPLC analysis. Tigloylshikonin was also found in the roots of L. erythrorhizon, which indicated that this new shikonin derivative is a typical component of naphthoquinone pigments in the roots of L. erythrorhizon.
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  • Oxygenated Hexylitaconates from a Marine Sponge-Derived Fungus Penicillium sp.
    Jian Lin Li, Ping Zhang, Yoon Mi Lee, Jongki Hong, Eun Sook Yoo, Kyung ...
    Article type: Note
    2011 Volume 59 Issue 1 Pages 120-123
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.120
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    In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1—4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1—4 were defined as α,β-dicarboxylic acid derivatives, such as hexylitaconic acid and tensyuic acids which were previously reported as metabolite of Aspergillus niger, Penicillium striatisporum, or Apiospora montagnei. The isolated compounds were evaluated for cytotoxicity against a panel of five human solid tumor cell lines, and for anti-inflammatory activity gauged by their inhibitory effects on the production of major pro-inflammatory mediators (nitric oxide (NO), interleukin (IL)-6, tumor necrosis factor (TNF)-α, and IL-1β) in murine macrophage cells. Compounds 1 and 4 showed weak inhibition of IL-1β production at the concentration of 200 μM.
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  • Glycosylated Constituents of Iris fulva and Iris brevicaulis
    Rui Fang, Nigel C. Veitch, Geoffrey C. Kite, Melanie-Jayne R. Howes, E ...
    Article type: Note
    2011 Volume 59 Issue 1 Pages 124-128
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.124
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    The major constituents of leaf extracts of Iris fulva KER GAWL. comprised a known flavone C-glycoside, 5,4′-dihydroxy-7-methoxyflavone-6-C-(6‴-O-(E)-p-coumaroyl-β-glucopyranosyl)(1‴→2″)-β-glucopyranoside (1) and the new monoterpene glycoside, linalyl-6′-O-(3″-hydroxy-3″-methylglutaroyl)-β-D-glucopyranoside (2), both of which were prominent components of Iris brevicaulis RAF. leaf extracts. The structure of a new polyacylated sucrose derivative (3a) obtained from the rhizomes of I. fulva was elucidated as 3-O-(E)-p-coumaroyl-β-D-fructofuranosyl-(2↔1′)-[2″,4″,6″-tri-O-acetyl-β-D-glucopyranosyl-(1″→3′)-(2′,6′-di-O-acetyl-4′-O-(E)-p-coumaroyl-α-D-glucopyranoside)]. Selective hydrolysis of the 4″-O-acetyl moiety of the terminal β-glucopyranosyl residue of 3a occurred after several hours in solution giving 3-O-(E)-p-coumaroyl-β-D-fructofuranosyl-(2↔1′)-[2″,6″-di-O-acetyl-β-D-glucopyranosyl-(1″→3′)-(2′,6′-di-O-acetyl-4′-O-(E)-p-coumaroyl-α-D-glucopyranoside)] (3b), which subsequently underwent further deacetylation.
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  • Flavonoid Glycosides from Chromolaena odorata Leaves and Their in Vitro Cytotoxic Activity
    Tran Manh Hung, To Dao Cuong, Nguyen Hai Dang, Shu Zhu, Pham Quoc Long ...
    Article type: Note
    2011 Volume 59 Issue 1 Pages 129-131
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.129
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    Two new flavonoid glycosides, (1, 2), and eleven known compounds, (3—13), were isolated from from a 70% EtOH extract of the leaves of Chromolaena odorata (Asteraceae). Their structures were elucidated by 1D and 2D NMR spectroscopic interpretation as well as by chemical studies. The newly isolated compounds were tested in vitro for their cytotoxic activities against the LLC and HL-60 cancer cell lines. Compound 1 showed cytotoxicity against LLC and HL-60 cancer cell lines with IC50 values of 28.2 and 11.6 μM, respectively. Compound 2 exhibited significant cytotoxic activity in the inhibition of HL-60 cancer cell lines with IC50 value of 10.8 μM.
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  • An Efficient Catalytic Oxidation of p-Alkoxypenols to p-Quinones Using Tetrabutylammonium Bromide and Oxone®
    Takayuki Yakura, Ayaka Ozono, Kohei Morimoto
    Article type: Note
    2011 Volume 59 Issue 1 Pages 132-134
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.132
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    A catalytic oxidation of p-alkoxyphenols was developed using tetrabutylammonium bromide (TBAB) and Oxone®. The reaction of p-alkoxyphenol (1) with a catalytic amount of TBAB in the presence of Oxone® as a co-oxidant in acetonitrile–water (2 : 1) gave the corresponding p-quinone (2) in excellent yield without special treatment.
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  • Flavonoid Constituents from the Roots of Acanthopanax brachypus
    Hao-bin Hu, Ji-hua Zhu
    Article type: Note
    2011 Volume 59 Issue 1 Pages 135-139
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.135
    JOURNAL FREE ACCESS
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    Two new natural products, (3R)-5,7-dihydroxy-8-(2″-O-veratroyl-β-D-glucopyranosyl)-3-(4′-hydroxyphenyl)-6-methylchroman-4-one (1) and 4′-hydroxyisoflavone-7-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside] (2), along with eleven other known flavonoids, were isolated from the roots of Acanthopanax brachypus. Their structures were elucidated on the basis of spectroscopic and chemical evidence.
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  • Structures of Minor Carotenoids from the Japanese Common Catfish, Silurus asotus
    Takashi Maoka, Naoshige Akimoto
    Article type: Note
    2011 Volume 59 Issue 1 Pages 140-145
    Published: January 01, 2011
    Released on J-STAGE: January 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.140
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    Three new carotenoids: 7′,8′,9′,10′-tetrahydro-β-cryptoxanthin, 7′,8′-dihydrodiatoxanthin, and (3S,6S,6′S)-ε-cryptoxanthin were isolated from the skin, fins, and gonads of the Japanese common catfish, Silurus asotus, as minor carotenoids. Their structures were determined based on chemical and spectroscopic data. Furthermore, 9Z and/or 9′Z geometrical isomers of parasiloxanthin, 7′,8′-dihydroparasiloxanthin, and 7′,8′-dihydro-β-cryptoxanthin were characterized by 1H-NMR.
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