Chemical and Pharmaceutical Bulletin
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ISSN-L : 0009-2363
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Volume 55, Issue 6
Displaying 1-27 of 27 articles from this issue
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Regular Articles
  • Study on the Cell Wall Skeleton Derived from Mycobacterium bovis BCG Tokyo 172 (SMP-105): Establishment of Preparation and Analytical Methods
    Yuko Uenishi, Takashi Okada, Seiji Okabe, Makoto Sunagawa
    2007 Volume 55 Issue 6 Pages 843-852
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.843
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    Mycobacterial cell walls have diverse adjuvant activities, and in particular, cell wall skeleton (CWS) of Mycobacterium bovis BCG has been expected as a drug for tumor immunotherapy. However, its molecular structure–biological activity relationship has not been fully elucidated despite more than 30 years of intensive research. Since it is important to secure purified CWS for such investigation, we established a preparation method of CWS from M. bovis BCG Tokyo 172 (SMP-105) and developed accurate, precise, and reliable analytical methods, based on previous reports. Furthermore, we confirmed that SMP-105 is composed of mycolic acids; arabinogalactan consisting of arabinose, galactose, and rhamnose; and peptidoglycan consisting of alanine, glutamic acid, diaminopimeric acid, muramic acid, glucosamine, and galactosamine. We also determined the levels of potential impurities that might be contaminated in the original bacterium or arise during the manufacturing process, such as glucose, mannose, non-constituted amino acids, as well as nucleic acid, trehaolse di-mycolate, and bacterial endotoxins. These results demonstrated that the prepared SMP-105 was of sufficient quality for research into the chemistry, bioactivity, and structure–activity relationship of CWS.
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  • Structures and DNA-Binding and Cleavage Properties of Ternary Copper(II) Complexes of Glycine with Phenanthroline, Bipyridine, and Bipyridylamine
    Masahiro Yodoshi, Mamiko Odoko, Nobuo Okabe
    2007 Volume 55 Issue 6 Pages 853-860
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.853
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    The crystal structures of the series of three complexes, [Cu(Gly)(bpy)Cl]·2H2O (1) (Gly=glycine; bpy=2,2′-bipyridine),1) [Cu(Gly)(phen)Cl]2·7H2O (2) (phen=1,10-phenanthroline), and [Cu(Gly)(bpa)(H2O)Cl] (3) (bpa=2,2′-bipyridylamine) were determined, and the coordination modes of Cu(II) ternary complexes were compared. The central Cu(II) atoms of complexes 1 and 3 have a similar distorted octahedral coordination geometry, while the Cu(II) atom of complex 2 has a distorted square pyramidal coordination. In all complexes, the aromatic heterocyclic compounds bpy, phen, and bpa, behave as a bidentate N,N′ ligand, and Gly behaves as a bidentate N,O ligand. DNA-binding properties of the complexes to calf thymus (CT) DNA were studied by using the fluorescence method. Each of the complexes showed binding propensity to CT DNA with the relative order 2>3≥1. DNA cleavage studies indicate that each of the complexes, especially 2, can cleave plasmid supercoiled pBR322 DNA in the presence of H2O2 and ascorbic acid with cleavage efficiency in the order 2>31. The degradation of the conformation of CT DNA by the complexes was also reflected in the decrease in the intensities of the characteristic CD bands with the relative order 2>31.
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  • Deprotection of a Silyl Group with Mesoporous Silica
    Akichika Itoh, Tomohiro Kodama, Yukio Masaki
    2007 Volume 55 Issue 6 Pages 861-864
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.861
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    The triethylsilyl (TES) group of silyl ethers of several types is selectively and easily removed in the presence of a t-butyldimethylsilyl (TBDMS) group with a mesoporous silica MCM-41/MeOH heterogeneous system. Comparison of the efficiency was carried out among several solvents, and among such promoters as common zeolites and ion-exchange resins. Furthermore, FSM-16, another mesoporous silica, was examined for the possibility of recycling by re-calcination at 400 °C after the reaction.
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  • Simultaneous Spectrophotometric Determination of Levodopa and Carbidopa in Pharmaceutical Formulations and Water Samples by Using Mean Centering of Ratio Spectra and H-Point Standard Addition Methods
    Tayyebeh Madrakian, Massoumeh Mohammadnejad
    2007 Volume 55 Issue 6 Pages 865-870
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.865
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    Two spectrophotometric methods are described for the simultaneous determination of binary mixtures of carbidopa and levodopa in pharmaceutical formulations, without prior separation steps, using the mean centering of ratio spectra and H-point standard addition methods (HPSAM). The methods are based on the difference in the absorption spectra for the products of the reaction of carbidopa and levodopa with 4-aminobenzoic acid in the presence of periodate ion at pH 4.0. The methods allow rapid and accurate determination of carbidopa and levodopa. The results showed that the methods were capable to simultaneous determination of 0.30—10.00 μg ml−1 and 0.50—10.00 μg ml−1 each of carbidopa and levodopa. The proposed methods were successfully applied to the simultaneous determination of carbidopa and levodopa in pharmaceutical samples.
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  • Studies on the Interaction of Cinnamic Acid with Bovine Serum Albumin
    Hedong Bian, Hairong Zhang, Qing Yu, Zhenfeng Chen, Hong Liang
    2007 Volume 55 Issue 6 Pages 871-875
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.871
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    The interaction between cinnamic acid and bovine serum albumin (BSA) have been studied at three temperatures, 296, 303 and 310 K. Fluorescence quenching spectra in combination with Fourier transform infrared (FT-IR) spectroscopy and circular dichroism (CD) spectroscopy was used to investigate the drug-binding mode, the binding constant and the protein structure changes in the presence of cinnamic acid in aqueous solution at pH 7.40. The fluorescence quenching constant Kq, Ksv and the binding constant K were calculated according to Stern–Volmer equation based on the quenching of the fluorescence of BSA in the presence of cinnamic acid. The thermodynamic parameters, the enthalpy (ΔH) and the entropy change (ΔS) were estimated to be −16.457 kJ mol−1 and 38.028 J mol−1 K−1 according to the van't Hoff equation. The displacement experiment shows that cinnamic acid can bind to the subdomain IIA (corresponding to Sudlow's drug binding site I). The distance between the tryptophan residues in BSA and cinnamic acid bound to site I was estimated to be 1.63 nm using Föster's equation on the basis of fluorescence energy transfer. The decreased binding constant in the presence of common ions indicates that common ions have effect on drug–BSA system.
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  • Neolemnane-Type Sesquiterpenoids from a Formosan Soft Coral Paralemnalia thyrsoides
    Ho-Cheng Huang, Chih-Hua Chao, Jui-Hsin Su, Chi-Hsin Hsu, Shin-Pin Che ...
    2007 Volume 55 Issue 6 Pages 876-880
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.876
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    Six new sesquiterpenoids, paralemnolins D—I (1—6), have been isolated from the EtOAc extract of the soft coral Paralemnalia thyrsoides. The structures of these metabolites were determined by extensive spectroscopic analysis and by comparison of their spectral data with those of related metabolites. The absolute stereochemistry of these metabolites was established by application of the Mosher's method on 1 and on the basis of the absolute structures of other related compounds previously isolated from the soft corals of the genera Paralemnalia and Lemnalia. Cytotoxicity of these metabolites toward a limited panel of cancer cell lines also is reported.
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  • Discovery of Novel 2-Anilinopyrazolo[1,5-a]pyrimidine Derivatives as c-Src Kinase Inhibitors for the Treatment of Acute Ischemic Stroke
    Harunobu Mukaiyama, Toshihiro Nishimura, Hiroaki Shiohara, Satoko Koba ...
    2007 Volume 55 Issue 6 Pages 881-889
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.881
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    We synthesized a series of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives and evaluated their ability to inhibit c-Src kinase; 7-(2-amino-2-methylpropylamino)-5-cyclopropyl-2-(3,5-dimethoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide 7o and 7-(2-amino-2-methylpropylamino)-2-(3,5-dimethoxyphenylamino)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide 7f showed potent inhibitory activity. Compound 7f inhibited c-Src selectively and exhibited satisfactory central nervous system (CNS) penetration. Furthermore, 7f·HCl reduced the infarct volume in vivo in a rat middle cerebral artery (MCA) occlusion model when administrated intraperitoneally.
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  • Prenylbicyclogermacrane Diterpenoids from the Formosan Soft Coral Nephthea elongata
    Ali Ali Hassan El-Gamal, Shang-Kwei Wang, Chang-Yih Duh
    2007 Volume 55 Issue 6 Pages 890-893
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.890
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    Seven new prenylbicyclogermacrane diterpenoids, pacificins K—Q (1—7), were isolated from the methylene chloride solubles of the Formosan soft coral Nephthea elongata. Their structures were elucidated by extensive spectroscopic analysis and their cytotoxicity against selected cancer cells was measured in vitro.
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  • Synthesis and Antibacterial Activity of New N-[2-(Thiophen-3-yl)ethyl] Piperazinyl Quinolones
    Bahram Letafat, Saeed Emami, Negar Mohammadhosseini, Mohammad Ali Fara ...
    2007 Volume 55 Issue 6 Pages 894-898
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.894
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    As a part of continuing search for potential antibacterial agents in the quinolones field, we have synthesized novel quinolone agents bearing N-[2-(thiophen-3-yl)ethyl] piperazinyl moiety in the 7-position of the quinolone ring. In vitro antibacterial evaluation of the target compounds showed that N-[2-(thiophen-3-yl)ethyl] group attached to piperazine ring served as promising C-7 substituent for piperazinyl quinolone antibacterials. Among these derivatives, ciprofloxacin analogues, containing N-[2-(thiophen-3-yl)-2-hydroxyiminoethyl] or N-[2-(thiophen-3-yl)-2-methoxyiminoethyl] residue provided a high inhibition against all the tested Gram-positive organisms including methicillin-resistant Staphylococcus aureus comparable or superior with respect to the reference drugs norfloxacin and ciprofloxacin.
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  • Facile Discrimination of Aldose Enantiomers by Reversed-Phase HPLC
    Takashi Tanaka, Tatsuya Nakashima, Toshihisa Ueda, Kenji Tomii, Isao K ...
    2007 Volume 55 Issue 6 Pages 899-901
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.899
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    One-pot reactions of aldoses with L-cysteine methyl ester and o-tolyl isothiocyanate yielded methyl 2-(polyhydroxyalkyl)-3-(o-tolylthiocarbamoyl)-thiazolidine-4(R)-carboxylates. Direct HPLC analysis of the reaction mixture and UV detection at 250 nm discriminated D- and L-enantiomers of aldoses. The reaction was applied to the determination of absolute configuration the sugar residues of an aroma precursor.
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Notes
  • Three New Limonoids from Cipadessa cinerascens
    Xiao-Hong Yuan, Bo-Gang Li, Chun-Xia Xu, Min Zhou, Hua-Yi Qi, Guo-Lin ...
    2007 Volume 55 Issue 6 Pages 902-904
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.902
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    Three new limonoids, cipadesins D—F (1—3), together with 8,15-dihydroxy-13E-labdane, β-sitosterol and β-daucosterol, were isolated from the leaves and bark of Cipadessa cinerascens. Their structures were elucidated by spectral evidence. X-Ray crystallographic analysis confirmed the structure of 1.
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  • Two New Sesquiterpenes from Alisma orientalis
    Zhi-Yong Jiang, Xue-Mei Zhang, Jun Zhou, Feng-Xue Zhang, Ji-Jun Chen, ...
    2007 Volume 55 Issue 6 Pages 905-907
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.905
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    Two new sesquiterpenoids named alismorientols A (1) and B (2) were isolated from the rhizomes of Alisma orientalis collected in Sichuan province, People's Republic of China. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR data including HSQC, HMBC, COSY, and ROESY) and X-ray crystallographic analysis. Anti-hepatitis B virus (HBV) bioassay revealed that compound 1 showed moderate anti-HBV activity in vitro with IC50 for HBsAg: 1.1 μM, for HBeAg: 14.7 μM.
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  • Lanostane-Type Triterpenoids from Diospyros discolor
    Chiy-Rong Chen, Chao-Wen Cheng, Min-Hsiung Pan, Yun-Wen Liao, Chih-Yin ...
    2007 Volume 55 Issue 6 Pages 908-911
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.908
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    Four new lanostane-type triterpenes, 24-ethyl-3β-methoxylanost-9(11)-en-25-ol (1), 3β-methoxy-24-methylenelanost-9(11)-en-25-ol (2), 3β-methoxy-25-methyl-24-methylenelanost-9(11)-en-21-ol (3) and 3β-methoxy-24-methyllanosta-9(11),25-dien-24-ol (4) together with three known triterpenes, betulinaldehyde, betulinic acid methyl ester, and ursaldehyde have been isolated from the methanol extract of the twigs of Diospyros discolor. The structures of those new compounds were elucidated by spectroscopic methods.
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  • Steroidal Alkaloids from Holarrhena antidysenterica (L.) WALL.
    Neeraj Kumar, Bikram Singh, Pamita Bhandari, Ajai Prakash Gupta, Vijay ...
    2007 Volume 55 Issue 6 Pages 912-914
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.912
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    Chemical investigations on the stem bark of Holarrhena antidysenterica resulted in the isolation of a new steroidal alkaloid designated as holadysenterine (1), together with three known steroidal alkaloids, conessine (2), isoconessimine (3) and kurchessine (4). Their structures were elucidated on the basis of 1D- and 2D-NMR techniques and high-resolution mass spectrometry.
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  • One-Pot Synthesis of Highly Conjugated Benzofuran Derivatives Based on Electrochemical Oxidation of Benzenediols in the Presence of Dibenzoylmethane
    Mohammad Rafiee, and Davood Nematollahi
    2007 Volume 55 Issue 6 Pages 915-917
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.915
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    Electrochemical oxidation of benzenediols (1—4) has been studied in the presence of dibenzoylmethane (5) as a nucleophile using cyclic voltammetry and controlled-potential coulometry. The results indicate that the electrochemically generated quinones participate in Michael addition reaction with 5 via various mechanisms to produce new benzofuran derivatives. We derived various products based on electrochemical oxidation in the controlled potential condition, at carbon electrode without toxic reagents in an undivided cell and ambient condition.
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  • New C18-Diterpenoid Alkaloids from Delphinium anthriscifolium var. savatieri
    Lei Song, Xiao-Xia Liang, Dong-Lin Chen, Xi-Xian Jian, Feng-Peng Wang
    2007 Volume 55 Issue 6 Pages 918-921
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.918
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    Five new C18-diterpenoid alkaloids, anthriscifolcines A (1), B (2), C (3), D (4), and E (5), together with a known C19-diterpenoid alkaloid delcorine (6), were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were established on the basis of spectral data (1D- and 2D-NMR, HR-ESI-MS).
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  • Convenient Synthetic Method for 3-(3-Substituted indol-2-yl)quinoxalin-2-ones as VEGF Inhibitor
    Katsuyuki Aoki, Jyun-ichi Koseki, Shuichi Takeda, Masaki Aburada, Ken- ...
    2007 Volume 55 Issue 6 Pages 922-925
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.922
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    It has already been reported that 3-(indol-2-yl)quinoxalin-2-ones1) have a potent inhibitory effect on the growth of tumor cells based on anti-angiogenesis activity. We have also carried out a structure–activity relationship (SAR) study of 3-(indol-2-yl)quinoxalin-2-ones, which showed a potent inhibitory activity toward the vascular endothelial growth factor (VEGF)-induced proliferation of human mesangial cells and the VEGF-induced auto-phosphorylation of human umbilical vein endothelial cells.2) Moreover, one of these compounds has a potent medicinal effect based on anti-angiogenic action, by oral administration2) (Chart 1, 9). However, since the existing synthetic methods1) for the preparation of 3-(indol-2-yl)quinoxalin-2-ones consist of multiple steps some of which require strict anhydrous conditions, a convenient and simple synthetic method in place of the existing method is desirable. As a result of the investigations into the synthetic procedures, 3-(3-substituted indol-2-yl)quinoxalin-2-ones can be easily prepared by the condensation of 3-substituted indoles with quinoxalin-2-ones in the presence of trifluoroacetic acid (TFA). Herein, we report the examination of these reaction conditions and the application of this new synthetic method to the synthesis of the derivatives as VEGF inhibitors.
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  • Chemical Constituents of Nepalese Propolis (II)
    Suraj Prakash Shrestha, Yuji Narukawa, Tadahiro Takeda
    2007 Volume 55 Issue 6 Pages 926-929
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.926
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    A novel flavanonol (1), three new isoflavones (2—4) and a new flavan-3-ol (5) were isolated along with ten other known flavonoids (6—15) from the methanolic extract of propolis collected from Chitwan, Nepal. Their structures were determined on the basis of spectral analysis.
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  • Synthesis of Bioreductive Esters from Fungal Compounds
    Natthida Weerapreeyakul, Rutchayaporn Anorach, Thidarut Khuansawad, Ch ...
    2007 Volume 55 Issue 6 Pages 930-935
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.930
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    Four new bioreductive esters (7—10) have been synthesized. Their structures composed of trimethyl lock containing quinone propionic acid with an ester linkage to the fungal cytotoxic compounds; preussomerin G (1), preussomerin I (2), phaseolinone (3) and phomenone (4). The synthesized esters are aimed to act via reductive activation specifically at the cancer cells, resulting from hypoxia and overexpression of reductases. Hence, the toxicity will be lessened during distribution across the normal cells. The anticancer activity was determined in cancer cell lines with reported reductase i.e., BC-1 cells and NCI-H187 as well as in non-reductase containing cancer cells; KB cells. When considering each cell lines, result showed that structure modification giving to 7—10 led to less cytotoxicity than their parent compounds (1—4). Both 7 and 8 were strongly cytotoxic (IC50≤5 μg/ml) to NCI-H187, whereas 9 and 10 were moderately cytotoxic (IC50=6—10 μg/ml) to BC-1 cells. Additional study of stability of represented phenolic ester (8) and an alcoholic ester (9) were performed. Result illustrated that both 8 and 9 were stable in the presence of esterase. Therefore, the cytotoxicity of the synthesized compounds (8—10) might be due to partial bioreductive activation in the cancer cells.
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  • Statistical Optimization of Tamsulosin Hydrochloride Controlled Release Pellets Coated with the Blend of HPMCP and HPMC
    Jeong-Soo Kim, Min-Soo Kim, Hee Jun Park, Sibeum Lee, Jeong-Sook Park, ...
    2007 Volume 55 Issue 6 Pages 936-939
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.936
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    The objective of the present study was to evaluate three coating parameters for the application of a blend of HPMCP and HPMC in ethylcellulose aqueous dispersions (Surelease®) in order to obtain controlled release of tamsulosin hydrochloride. The selected independent variables, HPMCP content (X1), HPMC content (X2) and coating level (X3), were optimized with a three-factor, three-level Box–Behnken design. The selected dependent variables were the cumulative percentage values of tamsulosin hydrochloride that had dissolved after 2, 3 and 5 h. Various dissolution profiles of the drug from controlled release pellets were obtained. Optimization was performed for X1, X2 and X3 using the following target ranges; 15%≤Y1≤30%; 50%≤Y2≤65%; 80%≤Y3≤95%. Results of the optimization procedure indicated that the optimized levels of HPMCP content (X1), HPMC content (X2) and coating level (X3) were 30%, 15% and 25%, respectively. Controlled release pellets coated with the optimized formulation provided a release profile that was close to predicted values. In addition, the dissolution profiles of the controlled release pellets coated with the optimized formulation were similar to those of the commercial product Harunal® capsule (f1=4.6, f2=78.7).
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  • New Sesquiterpenes and Calebin Derivatives from Curcuma longa
    YongChi Zeng, Feng Qiu, Kyoko Takahashi, JianMu Liang, GeXia Qu, XinSh ...
    2007 Volume 55 Issue 6 Pages 940-943
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.940
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    One novel sesquiterpene with new skeleton, (6S)-2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one (1), two new bisabolane sesquiterpenes, (6S)-2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one (2), (6S)-2-methyl-6-(4-formylphenyl)-2-hepten-4-one (3), and two calebin derivatives, 4″-(4′′′-hydroxyphenyl-3′′′-methoxy)-2″-oxo-3″-butenyl-3-(4′-hydroxyphenyl)-propenoate (4) and 4″-(4′′′-hydroxyphenyl)-2″-oxo-3″-butenyl-3-(4′-hydroxyphenyl-3′-methoxy)-propenoate (5) were isolated along with five known bisabolane sesquiterpenes from Curcuma longa. 1—4 were new compounds and 5 was a new natural product. Their structures were established by spectral methods.
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  • Development of Tubulin-Polymerization Inhibitors Based on the Thalidomide Skeleton
    Hiroshi Aoyama, Tomomi Noguchi, Takashi Misawa, Takanori Nakamura, Hir ...
    2007 Volume 55 Issue 6 Pages 944-949
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.944
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    We synthesized a series of compounds based on the potent tubulin-polymerization inhibitor 5-hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione [5HPP-33 (3)], which is structurally derived from thalidomide (1), and investigated their inhibitory effects on tubulin polymerization. Direct interaction between 5HPP-33 (3) and α,β-tubulin heterodimer protein was demonstrated by means of a surface plasmon resonance study.
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  • Two New Xanthones Isolated from the Stem Bark of Garcinia lancilimba
    Nian-Yun Yang, Quan-Bin Han, Xin-Wei Cao, Chun-Feng Qiao, Jing-Zheng S ...
    2007 Volume 55 Issue 6 Pages 950-952
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.950
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    Two new xanthones, 1,5,6-trihydroxy-6′,6′-dimethyl-2H-pyrano(2′,3′:3,4)-2-(3-methylbut-2-enyl)xanthone (1) and 1,6,7-trihydroxy-6′,6′-dimethyl-2H-pyrano(2′,3′:3,2)-4-(3-methylbut-2-enyl)xanthone (2), have been isolated from the stem bark of Garcinia lancilimba (Guttiferae), together with six known xanthones. Their structures were identified on the basis of extensive spectral evidence including detailed 2D NMR and HR-MS data. Two new compounds showed moderate inhibitory effect on human breast cancer MDA-MB-435S cell line.
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  • (3R,4aR,5S,6R)-6-Hydroxy-5-methylramulosin: a New Ramulosin Derivative from a Marine-Derived Sterile Mycelium
    Ahmed Atef El-Beih, Hikaru Kato, Tomihisa Ohta, Sachiko Tsukamoto
    2007 Volume 55 Issue 6 Pages 953-954
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.953
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    (3R,4aR,5S,6R)-6-Hydroxy-5-methylramulosin (1) was isolated from a culture of a sterile mycelium, which was derived from the green alga, Codium fragile, along with (−)-5-methylmellein (2), (−)-5-hydroxymethylmellein (3), and (−)-(3R,4R)-cis-4-hydroxy-5-methylmellein (4). The absolute configuration of 1 was determined by the NMR data along with the lactone sector rule by circular dichroism (CD). Compound 1 exhibited moderate cytotoxic activity against HeLa cells.
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  • Development of Novel Hemilabile Segphos P–P=O Ligands
    Yoshimasa Fukuda, Kazuhiro Kondo, Toyohiko Aoyama
    2007 Volume 55 Issue 6 Pages 955-956
    Published: 2007
    Released on J-STAGE: June 01, 2007
    DOIhttps://doi.org/10.1248/cpb.55.955
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    Development of novel chiral hemilabile Segphos P–P=O ligands is described. The ligands are examined for enantioselective Pd-catalyzed allylic alkylation of cyclic allylic acetates.
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