Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 57, Issue 6
Displaying 1-24 of 24 articles from this issue
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Regular Articles
  • Preparation and Evaluation of Gastroretentive Floating Tablets of Silymarin
    Rajeev Garg, Ghanshyam Das Gupta
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 545-549
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.545
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    The present study performed by preparation and evaluation of floating tablets of Silymarin as model drug for prolongation of gastric residence time. Floating effervescent tablets were formulated by various materials like hydroxypropyl methylcellulose (HPMC) K 4M, K 15M, psyllium husk, swelling agent as crospovidone and microcrystalline cellulose and gas generating agent like sodium bicarbonate and citric acid and evaluated for floating properties, swelling characteristics and in vitro drug release studies. Floating noneffervescent tablets were prepared by polypropylene foam powder and different matrix forming polymers like HPMC K 4M, Carbopol 934P, xanthan gum and sodium alginate. In vitro drug release studies were performed and drug release kinetics evaluated using the linear regression method was found to follow both the Higuchi and the Korsemeyer and Peppas equation. The drug release mechanism was found fickian type in most of the formulations. The developed floating tablets of Silymarin may be used in clinic for prolonged drug release for at least 24 h, thereby improving the bioavailability and patient compliance.
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  • Synthesis and Structural Pattern Recognition of 5-(2′-Alkoxycarbonyl-substituted phenoxy)furfural Derivatives
    Chia-Lin Chang
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 550-556
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.550
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    The ethyl 5-(2′-alkoxycarbonyl-substituted phenoxy)furan-2-carboxylates (1C—13C) showed good anti-platelet aggregation,1) anti-allergic2) and anti-inflammatory activities.2) A series of 5-(2′-alkoxycarbonyl-substituted phenoxy)furfurals (1F—13F) were prepared for comparing the above activities. The objectives of this research are the synthesis and structural pattern recognition of compounds 1F—13F. The Silica Gel 60 column chromatography method was employed to separate and purify pure compounds 1F—13F by three solvent systems. For the structure elucidation of compounds 1F—13F, four spectroscopic methods were used: electron impact mass (EI-MS), UV–VIS, IR and NMR spectrometers. With the help of spectrometers, investigations can be performed on spectroscopic data. A simple methodology for recognizing structural patterns was carried out with the aid of statistical analysis designed to establish the classification model of the structural skeleton in this research. It was found that compounds 1C—13C and 1F—13F have similar chemical profiles and are clustered into one group. The pattern plots revealed valuable information and showed good correlation between compounds 1C—13C and 1F—13F. These findings correlate directly with the resulting spectroscopic data. These results with those obtained by EI-MS and NMR patterns give insight into a reliable pattern recognition for determining both 1C—13C and 1F—13F skeletons.
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  • Synthesis and Antimicrobial Activity of Some 5-Substituted-3-phenyl-Nβ-(Substituted-2-oxo-2H-pyrano[2,3-b]quinoline-3-carbonyl)-1H-indole-2-carboxyhydrazide
    Basavarajaiah Suliphal Devara Mathada, Mruthyunjayaswamy Bennikallu Hi ...
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 557-560
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.557
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    Ethyl 3-oxo-3-{2-[(5-substituted-3-phenyl-1H-indol-2-yl)carbonyl]hydrazinyl}propanoates 5a—b were synthesized according to the literature method. These on further reaction with substituted-2-hydroxy-3-formylquinolines 3a—e yielded 5-substituted-Nβ-(2-oxo-2H-pyrano[2,3-b]quinoline-3-carbonyl)-3-phenyl-1H-indole-2-carbohydrazides 6a—j. Structures of the all the newly synthesized compounds were confirmed by spectral data. All these compounds have been screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Bacillus subtilus, antifungal activity against Aspergillus niger and Candida albicans and antituberculosis activity against Mycobacterium tuberculosis (H37Rv).
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  • Synthesis and Bioassay of Oxazolyl/Thiazolyl Selenadiazoles, Thiadiazoles and Diazaphospholes
    Venkatapuram Padmavathi, Konda Mahesh, Annaji Venkata Nagendra Mohan, ...
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 561-566
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.561
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    A new class of bis heterocycles, oxazolyl/thiazolyl selenadiazoles, thiadiazoles and diazaphospholes were prepared from phenacylsulfonylacetic acid methyl ester and tested for their antimicrobial and antioxidant properties.
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  • Design, Synthesis and Evaluation of Tetrahydroisoquinolines as New Kinesin Spindle Protein Inhibitors
    Cheng Jiang, Qidong You, Fei Liu, Wutong Wu, Qinglong Guo, Jiwang Cher ...
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 567-571
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.567
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    In this study, a series of tetrahydroisoquinolines have been synthesized and identified as novel kinesine spindle protein (KSP) inhibitors based on the pharmacophore we have mapped and the crystal structure of monastrol bound to the target protein. The KSP inhibitory activities of all the designed compounds were tested using cloned Human KSP protein. All thirteen compounds were more potent than the control, monastrol, in Human KSP protein adenosine triphosphatase (ATPase) assays. Three compounds (1b, 1g, 1h) exhibited over 100 times higher potency than monastrol. Cytotoxic results in vitro by MTT method indicated that nine of these compounds (1a, 1b, 1c, 1d, 1e, 1g, 1h, 1j, 1k) were more active than monastrol. In particular, compounds 1b and 1g, each of which contains a hydrophilic group on the side chain at the 2-position, exhibited excellent cell-killing activities against HepG2 cells.
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  • Effect of an Experimental Design for Evaluating the Nonlinear Optimal Formulation of Theophylline Tablets Using a Bootstrap Resampling Technique
    Hiroaki Arai, Tatsuya Suzuki, Chosei Kaseda, Kozo Takayama
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 572-579
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.572
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    The optimal solutions of theophylline tablet formulations based on datasets from 4 experimental designs (Box and Behnken design, central composite design, D-optimal design, and full factorial design) were calculated by the response surface method incorporating multivariate spline interpolation (RSMS). Reliability of these solutions was evaluated by a bootstrap (BS) resampling technique. The optimal solutions derived from the Box and Behnken design, D-optimal design, and full factorial design dataset were similar. The distributions of the BS optimal solutions calculated for these datasets were symmetrical. Thus, the accuracy and the reproducibility of the optimal solutions enabled quantitative evaluation based on the deviations of these distributions. However, the distribution of the BS optimal solutions calculated for the central composite design dataset were almost unsymmetrical, and the basic statistic of these distributions could not be conducted. The reason for this problem was considered to be the mixing of the global and local optima. Therefore, self-organizing map (SOM) clustering was applied to identify the global optimal solutions. The BS optimal solutions were divided into 4 clusters by SOM clustering, the accuracy and reproducibility of the optimal solutions in each cluster were quantitatively evaluated, and the cluster containing the global optima was identified. Therefore, SOM clustering was considered to reinforce the BS resampling method for the evaluation of the reliability of optimal solutions irrespective of the dataset style.
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  • Synthesis of New 2-Thio-[1,2,4]triazolo[1,5-c]quinazoline Derivatives and Its Antimicrobial Activity
    Lyudmila Antipenko, Alexander Karpenko, Sergey Kovalenko, Andrew Katse ...
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 580-585
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.580
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    A series of novel ([1,2,4]triazolo[1,5-c]quinazolin-2-ylthio)carboxylic acids 2a—d and esters 3a—l were synthesized and evaluated for antimicrobial activity. Alkylation of potassium 2-thio-[1,2,4]triazolo[1,5-c]quinazoline 1 with halogenocarboxylic acids and its esters proceeded S-regioselectively. During acid catalyzed esterification of 2a—c, degradation of the pyrimidine ring was observed. The structures of the compounds were elucidated by FT-IR, 1H- and 13C-NMR, electron impact mass spectra (EI-MS) and LC-MS spectral data. Antimicrobial and antifungal activity of synthesized compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Aspergillus niger, Mycobacterium luteum, Candida albicans and Candida tenuis. Acids 2a and 2c exhibited significant activity against C. albicans, which was additionally confirmed by the bioluminescence inhibition test and interrelated with their lipophilicity.
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  • Potency Fingerprint of Herbal Products Danshen Injection for Their Quality Evaluation
    Yan-Xu Chang, Dong-Mei Yan, Lin-Lin Chen, Xiao-Ping Ding, Jin Qi, Li-Y ...
    Article type: Regular Article
    2009 Volume 57 Issue 6 Pages 586-590
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.586
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    The fingerprint technique has been studied frequently as a useful strategy for quality of traditional Chinese medicine. A novel potency fingerprint that can quantitatively analyze the antioxidant activity of individual constituent and provide the total antioxidant activities of the samples has been developed by high-performance liquid chromatography coupled with ultraviolet and pyrogallol–luminol chemiluminescence detection (HPLC-diode array detection (DAD)-PLD). Hierarchical clustering analysis has been used as a powerful pattern recognition tool to identify and classify Danshen injection from different factories. In addition, the combination use of the chromatographic fingerprint and potency fingerprint with principal component analysis was applied to quality control of Danshen injection. The results demonstrated that the proposed potency fingerprint was a useful means to control the quality and to clarify the possible mechanism of action of herbal products.
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Notes
  • Novel Furanylarylene Arylsulfonylindolesulfonamides: Synthesis and Their Antibacterial Evaluation
    Chennan Ramalingan, In-Sook Lee, Young-Woo Kwak
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 591-596
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.591
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    An array of furanylarylene arylsulfonylindolesulfonamides was synthesized through multi-step synthetic protocols involving bromination, stannylation, Stille cross coupling, reduction, arylsulfonylation, chlorosulfonylation, and condensation reactions. As a preliminary evaluation, these analogs were tested for antibacterial activity against a series of bacterial strains such as Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae using a two-fold serial dilution assay. Whereas analogs possessing unsubstitution, bromosubstitution, or methyl substitution on the benzene ring of benzenesulfonyl group were less active/inactive, the methoxy and chloro substituted counterparts were demonstrated to be comparatively more active. A few of them were found to exhibit better activity than the standard, streptomycin against selective organisms.
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  • Sesquiterpenes from Ainsliaea fragrans and Their Inhibitory Activities against Cyclooxygenases-1 and 2
    Hao Wang, Ting Wu, Ming Yan, Ge Liu, Ping Li, Xiao-Qi Zhang, Wen-Cai Y ...
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 597-599
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.597
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    One new guaiane-type sesquiterpene glycoside, 2′-O-E-caffeoyl-8α-hydroxy-11α,13-dihydro-3β-O-β-D-glucozaluzanin C (1), was isolated from the whole herb of Ainsliaea fragrans (Compositae), together with five known sesquiterpene lactones: 8α-hydroxy-11α,13-dihydro-3β-O-β-D-glucozaluzanin C (2), 8α-hydroxy-11α,13-dihydrozaluzanin C (3), 3α-hydroxy-11β,13-dihydro-8α-O-β-D-glucozaluzanin C (4), 3β-hydroxy-11β,13-dihydro-8α-O-β-D-glucozaluzanin C (5), 3β-O-β-D-glucozaluzanin C (6). The structures of isolated compounds were established by means of 1D and 2D NMR spectroscopy and chemical methods. All isolates obtained in the present study were evaluated for their inhibitory effects against cyclooxygenases-1 and 2 in vitro, and the structure–activity relationships were also discussed.
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  • Alkaloids from the Stem Bark of Micromelum falcatum
    Xiong Ming Luo, Shu Hua Qi, Hao Yin, Cheng Hai Gao, Si Zhang
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 600-602
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.600
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    Two new quinoldione alkaloids, methyl 2-(3-hydroxy-1-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate (1) and 3-hydroxy-1-methyl-3-(2-oxopropyl)quinoline-2,4(1H,3H)-dione (2), and two quinolinone alkaloids previously synthesized but first isolated as natural products, N-methylflindersine (3) and 4-hydroxy-3-methoxy-1-methyl-2(1H)-quinolinone (4), were isolated from the stem bark of Micromelum falcatum, together with the known N-methylswietenidine-B (5). Their structures were established mainly on the basis of 1D- and 2D-NMR techniques. All compounds were evaluated for toxicity towards brine shrimp larvae, and 3 showed strong toxicity with an LD50 value of 1.39 μg/ml.
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  • Synthesis, Spectroscopic, and Antimicrobial Studies of the Bivalent Nickel, and Copper Complexes of Thiosemicarbazide
    Shikha Parmar, Yatendra Kumar
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 603-606
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.603
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    A series of metal complexes of Ni(II), and Cu(II) having the general composition [M(L)2X2] with thiosemicarbazide have been prepared and characterized by elemental chemical analysis, molar conductance, magnetic susceptibility measurements, mass, IR, electron paramagnetic resonance, and electronic spectral studies. The IR spectral data suggest the involvement of sulfur and terminal amino nitrogen in coordination to the central metal ion. On the basis of spectral studies, an octahedral geometry has been assigned for the Ni(II) complexes whereas tetragonal geometry for Cu(II) complexes. Thiosemicarbazide and its metal complexes have been tested in vitro against a number of microorganisms in order to assess their antimicrobial properties.
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  • A Concise Synthesis of Licochalcone E and Its Regio-Isomer, Licochalcone F
    Younghwa Na, Jeong-Heon Cha, Ho-Geun Yoon, Youngjoo Kwon
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 607-609
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.607
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    Licochalone E is one of the retrochalcones isolated from Glycyrrhiza inflata which shows potent cytotoxicty against human tumor cell lines. Biological studies suggested that topoisomerase I inhibition correlates with cytotoxic properties. Other research revealed that licochalcone E modulats the nuclear factor (NF)-kB and Bcl-2 families to induce endothelial cell apoptosis. Since licochalcone E has been isolated recently, synthetic information on this compound has not been reported yet. Therefore we report the concise synthesis of licochalcone E and its regioisomer, tentatively called licochalcone F, by employing Claisen rearrangement for key intermediate synthesis.
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  • Two New Amaryllidaceae Alkaloids from the Bulbs of Lycoris radiata
    Lei Wang, Xiao-Qi Zhang, Zhi-Qi Yin, Ying Wang, Wen-Cai Ye
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 610-611
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.610
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    Two new Amaryllidaceae alkaloids, named lycoranines A (1) and B (2), were isolated from the bulbs of Lycoris radiata. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compound 2 was a new-type alkaloid, which provided a new insight into the biosynthesis of alkaloids in Amaryllidaceae plants.
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  • Two Sulfated Triterpenoidal Saponins from the Barks of Zygophyllum fabago L.
    Yu-Lin Feng, He-Ran Li, Yi Rao, Xiao-Jian Luo, Li-Zhen Xu, Yue-Sheng W ...
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 612-614
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.612
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    Two new sulfated triterpenoid saponins, zygophylosides Q (1) and R (2), have been isolated from the barks of Zygophyllum fabago L. Their structures were elucidated as 3β,24,28,30-tetrahydro-urs-20-ene-24-O-sulphonyl-3-O-[β-D-glucopyranosyl]-30-O-β-D-glucopyranoside and 3β,24,28,30-tetrahydro-urs-20-ene-24-O-sulphonyl-3-O-[β-D-xylopyranosyl]-30-O-β-D-glucopyranoside, respectively, by spectral and chemical evidence.
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  • Part 2: Influence of 2-Euryfuryl-1,4-naphthoquinone and Its peri-Hydroxy Derivatives on Both Cell Death and Metabolism of TLT Cells, a Murine Hepatoma Cell Line. Modulation of Cytotoxicity by Vitamin C
    Julio Benites, Jaime Adolfo Valderrama, Henryk Taper, Pedro Buc Calder ...
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 615-619
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.615
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    2-Euryfuryl-1,4-naphthoquinone C1 and its 5- and 5,8-hydroxy derivatives C2 and C3, were tested for their cytotoxicity towards transplantable liver tumor (TLT) cells (a murine hepatoma cell line) in the absence and in the presence of vitamin C. Cell death, caspase-3 activity and two metabolic end-points, namely the intracellular content of ATP and glutathione (GSH), were employed to evaluate their cytotoxicity. In a range of concentration from 0 to 10 μg/ml C1 and C3 were non toxic against TLT cells, while compound C2 killed about 50% of cells by necrosis. Interestingly, the presence of vitamin C did not enhance the cytolysis of C2, but its addition exacerbated the effects of the three compounds on both ATP and GSH contents, the two metabolic end points selected in our study. Our assumption is that the electron donor effect of the peri-hydroxyl substituents on euryfurylnaphthoquinones and the hydrogen bond between the peri-hydroxy and quinone carbonyl groups influence the electron-acceptor capability of the quinone nucleus and thus modifies the electron transfer from ascorbate to the electroactive quinone nucleus. The combination of euryfurylnaphthoquinones with vitamin C may be of potential clinical interest, because cancer cells accumulate vitamin C, they are sensitive to an oxidant insult and they depend on glycolysis (ATP formation) for their survival.
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  • Hepatoprotective Constituents from Cleome droserifolia
    Maged Saad Abdel-Kader, Saleh Ibrahim Alqasoumi, Areej Mohammad Al-Taw ...
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 620-624
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.620
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    The effect of ethanol extract from aerial parts of Cleome droserifolia was investigated against carbon tetrachloride induced liver injury. The hepatoprotective activity was evaluated through the quantification of biochemical parameters and confirmed using histopathology analysis. Efficient hepatoprotective effect was achieved by crude extract, fractions and some pure compounds. The phytochemical studies showed that the petroleum ether fraction afforded two known guaiane sesquiterpenes buchariol (1) and teucladiol (2) in addition to daucosterol (β-sitosterol glucoside) (3). The CHCl3 fraction afforded three known flavonoid derivatives; 5,3′-dihydroxy-3,6,7,4′,5′-pentamethoxyflavone (4), 5′-hydroxy-3,6,7,3′,4′,5′-hexamethoxyflavone (5) and luteolin (6) and a known dolabellane diterpene (1R,2R,3E,7E,11R,12S)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol (7). The active parts of the MeOH fraction afforded the previously unreported 3′-methoxy-3,5,4′-trihydroxy flavone-7-neohesperidoside (8) and a known megastigmane norterpene; (6S,9R)-roseoside (9).
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  • Two New Furanoid Norditerpenes from Dioscorea bulbifera
    Gang Wang, Jin-Song Liu, Bin-Bin Lin, Guo-Kai Wang, Ji-Kai Liu
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 625-627
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.625
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    Two new furanoid norditerpenes (1, 2) were isolated from the root tubers of Dioscorea bulbifera L. Their structures were established on the basis of extensive spectroscopic analysis.
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  • Flavonoids from Bauhinia glauca subsp. pernervosa
    Zeng-Bao Wu, Yu-Ying Zhao, Xiu-Wei Yang, Hong Liang
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 628-631
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.628
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    Seven flavonoids were isolated from Bauhinia glauca subsp. pernervosa, and their structures were elucidated as 6-methyl homoeriodictyol (1), bauhiniaside A (2), bauhiniasin (3), 2′,4′-dihydroxy-4-methoxydihydrochalcone-4′-O-β-D-glucopyranoside (4), farrerol (5), homoeriodictyol (6), and 2′,4′-dihydroxy-4-methoxydihydrochalcone (7) on the basis of spectroscopic analysis. Compounds 1, 2 and 3 are new flavonoids, compound 4 is a new natural product, its NMR data is reported for the first time. Compounds 5 and 7 were isolated from the genus Bauhinia for the first time, and compound 6 was isolated from the plant for the first time.
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  • Steroidal Glycosides from the Fruits of Solanum viarum
    Masateru Ono, Takamasa Kakiuchi, Hiroaki Ebisawa, Yuki Shiono, Takanor ...
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 632-635
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.632
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    Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.
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  • Two New C13 nor-Isoprenoids from the Leaves of Casearia sylvestris
    Wei Wang, Xing-Cong Li, Zulfiqar Ali, Ikhlas Ahmed Khan
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 636-638
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.636
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    Two new C13 nor-isoprene glycosides, (6S,9S)-6,9-dihydroxymegastiman-4-en-9-O-β-D-glucopyranoside (1) and (6S,9S)-6,9-dihydroxymegastiman-4-en-9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (2) were isolated from the leaves of Casearia sylvestris, along with icariside B5 (3), byzantionoside B (4), blumenol B (5), blumenol C (6) and loliolide (7). The structures of these compounds were determined on the basis of 1D and 2D NMR, MS and circular dichroism (CD) spectroscopic analyses, chemical methods and comparison with the literature data.
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  • Three New 7.3′,8.5′-Connected Bicyclo[3.2.1]octanoids and Other Neolignans from Leaves of Nectandra amazonum NEES. (Lauraceae)
    Ericsson David Coy Barrera, Luis Enrique Cuca Suárez
    Article type: Notes
    2009 Volume 57 Issue 6 Pages 639-642
    Published: June 01, 2009
    Released on J-STAGE: June 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.639
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    Three new 7.3′,8.5′-connected (macrophyllin-type) bicyclo[3.2.1]octanoid neolignans (nectamazins A—C, 1—3) were isolated from leaves of Nectandra amazonum NEES., along with seven known neolignans (4—10). The structures of 1—3 were characterized by spectroscopic methods (1D, 2D NMR) and the absolute configuration was assigned on the basis of circular dichroism (CD) spectra supported by nuclear Overhauser effect spectroscopy (NOESY) correlations. The new compounds showed inhibition activity against platelet activating factor (PAF)-induced aggregation of rabbit platelets.
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