Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 56, Issue 2
Displaying 1-23 of 23 articles from this issue
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Regular Articles
  • Stability Indicating Methods for the Determination of some Anti-fungal Agents Using Densitometric and RP-HPLC Methods
    Bahia Abbas Mousa, Naglaa Mahmoud El-Kousy, Ramzia Ismail El-Bagary, N ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 143-149
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.143
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    Two chromatographic methods were developed for the determination of some anti-fungal drugs in the presence of either their degradation products or cortisone derivatives. The densitometric method determined mixtures of each of ketoconazole (KT), clotrimazole (CL), miconazole nitrate (MN) and econazole nitrate (EN) with the degradation products of each one. Mixtures of MN with hydrocortisone (HC) and of EN with triamcinolone acetonide (TA) were also successfully separated and determined by this technique. For KT and CL, a mixture of methanol : water : triethylamine (70 : 28 : 2 v/v) was used as a developing system and the spots were scanned at 243 nm and 220 nm for KT and CL, respectively. For MN and EN, a mixture of hexane : isopropyl alcohol : triethylamine (80 : 17 : 3 v/v) was used as a developing system and the spots were scanned at 225 nm for both drugs. The HPLC method determined mixtures of CL or EN with their degradation products which were separated and quantified on a Zorbax C8 column. Elution was carried out using methanol : phosphate buffer pH 2.5 (65 : 35 v/v) as a mobile phase at a flow rate of 1.5 ml/min and UV detection at 220 nm for CL. For EN, a mixture of methanol : water containing 0.06 ml triethylamine pH 10 (75 : 25 v/v) was used as a mobile phase at a flow rate of 1.5 ml/min and UV detection at 225 nm. The methods were also used to separate mixtures of CL with betamethasone dipropionate (BD) and EN with TA in a laboratory prepared mixture and in pharmaceutical preparations. The methods were sensitive, precise and applicable for determination of the drugs in pharmaceutical dosage forms.
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  • Optimization of Metformin HCl 500 mg Sustained Release Matrix Tablets Using Artificial Neural Network (ANN) Based on Multilayer Perceptrons (MLP) Model
    Uttam Mandal, Veeran Gowda, Animesh Ghosh, Anirbandeep Bose, Uttam Bha ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 150-155
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.150
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    The aim of the present study was to apply the simultaneous optimization method incorporating Artificial Neural Network (ANN) using Multi-layer Perceptron (MLP) model to the development of a metformin HCl 500 mg sustained release matrix tablets with an optimized in vitro release profile. The amounts of HPMC K15M and PVP K30 at three levels (−1, 0, +1) for each were selected as casual factors. In vitro dissolution time profiles at four different sampling times (1 h, 2 h, 4 h and 8 h) were chosen as output variables. 13 kinds of metformin matrix tablets were prepared according to a 23 factorial design (central composite) with five extra center points, and their dissolution tests were performed. Commercially available STATISTICA Neural Network software (Stat Soft, Inc., Tulsa, OK, U.S.A.) was used throughout the study. The training process of MLP was completed until a satisfactory value of root square mean (RSM) for the test data was obtained using feed forward back propagation method. The root mean square value for the trained network was 0.000097, which indicated that the optimal MLP model was reached. The optimal tablet formulation based on some predetermined release criteria predicted by MLP was 336 mg of HPMC K15M and 130 mg of PVP K30. Calculated difference (f1 2.19) and similarity (f2 89.79) factors indicated that there was no difference between predicted and experimentally observed drug release profiles for the optimal formulation. This work illustrates the potential for an artificial neural network with MLP, to assist in development of sustained release dosage forms.
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  • Preparation of Glucagon-Like Peptide-1 Loaded PLGA Microspheres: Characterizations, Release Studies and Bioactivities in Vitro/in Vivo
    Dongfeng Yin, Ying Lu, He Zhang, Guoqing Zhang, Hao Zou, Duxin Sun, Ya ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 156-161
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.156
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    The gut hormone glucagon-like peptide-1 (GLP-1) is proposed for treatment of Type II diabetes mellitus. However, the short half life of GLP-1 in vivo is a major limitation for its application due to the frequent invasive administrations. To provide a optimal formulation to overcome this limitation, we developed a GLP-1 entrapped microspheres to achieve sustained release GLP-1 for 4-week. GLP-1 was stabilized by GLP-1-zinc complexation with zinc carbonate and encapsulated in poly(D,L-lactic-co-glycolic acid) (PLGA) with S/O/O solvent extraction to obtain GLP-1 loaded PLGA microspheres (MS). The characteristics of MS were evaluated as follows: The surface morphyology was assessed by scanning electron microscopy (SEM); The drug encapsulation efficiency and GLP-1 controlled release profile was tested by HPLC; The sustained release of GLP-1 MS in vivo and pharmacological efficacy were studied in normal mice and streptozotocin (STZ)-induced diabetic mice model after subcutaneous administration of GLP-1 MS. GLP-1-zinc complexation significantly reduced initial burst release from 37.2 to 7.5%. The controlled release bioactive GLP-1 in vitro was achieved for 4-week period by zinc complexation and addition of ZnCO3. The optimal and complete cumulative release of GLP-1 from MS was increased from 23 to 63% in 28 d by using low MW PLGA (MW 14000). The in vivo testing in normal mice and diabetic mice suggest that this zinc-stabilized technique combined with S/O/O method in the presence of water insoluble antacid additive ZnCO3 preserve the biological activity of GLP-1. GLP-1 MS formulation achieved controlled released in vivo for 28 d and exhibit sustained long term pharmacological efficacy to decrease blood glucose level in diabetic mice. This GLP-1 MS formulation provides a practical formulation for long-term sustained delivery of GLP-1 to treat Type II diabetes.
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  • Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin
    Guang Liang, Shulin Yang, Lijuan Jiang, Yu Zhao, Lili Shao, Jian Xiao, ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 162-167
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.162
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    The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro anti-bacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.
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  • Synthesis, Characterization and Hypoglycemic Activity of Zn(II), Cd(II) and Hg(II) Complexes with Glibenclamide
    Khalid Rasheed, Muhammad Ilyas Tariq, Christy Munir, Ishtiaq Hussain, ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 168-172
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.168
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    A series of group 12 elements for Zn(II), Cd(II), Hg(II) complexes of glibenclamide were synthesized and characterized using various spectroscopic techniques and magnetic moments. The complexes exhibited significant activity against gram-negative and gram-positive bacteria species. Zn(II) complex showed remarkable hypoglycemic activity whereas Cd(II) and Hg(II) complexes exhibited antibacterial activity.
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  • Phellifuropyranone A: A New Furopyranone Compound Isolated from Fruit Bodies of Wild Phellinus linteus
    Kazuo Kojima, Takamasa Ohno, Makoto Inoue, Hajime Mizukami, Akito Naga ...
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 173-175
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.173
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    A new furopyranone, phellifuropyranone A, was isolated from fruit bodies of wild Phellinus linteus as well as phelligridin G, and their chemical structures were determined by various spectroscopic methods including measurement of NMR spectra. Phellifuropyranone A together with meshimakobnol A and meshimakobnol B showed antiproliferative activity against mouse melanoma cells and human lung cancer cells in vitro.
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  • Process Development and Large-Scale Synthesis of NK1 Antagonist
    Ichiro Araya, Shintaro Kanazawa, Hiroyuki Akita
    Article type: Regular Articles
    2008 Volume 56 Issue 2 Pages 176-180
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.176
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    A scaleable synthetic route is described to obtain 2-(4-acetylpiperadin-1-yl)-6-[3,5-bis(trifluoromethyl)phenylmethyl]-4-(2-methylphenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one (1, KRP-103) as a neurokinin (NK)1 antagonist. The key step in the synthesis is the intramolecular cyclization of N-[3,5-bis(trifluoromethyl)phenylmethyl]-N-(3-hydroxypropyl)-4-chloro-6-(2-methylphenyl)-2-methylthiopyrimidine-5-carboxamide (15) which was obtained by amide formation between 4-(2-methylphenyl)-2-methylthio-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid (8) and 3-[3,5-bis(trifluoromethyl)phenylmethylamino]-1-propanol (3). Treatment of 15 with 1,8-diazabicyclo[5,4,0]undec-7-ene provided 6-[3,5-bis(trifluoromethyl)phenylmethyl]-4-(2-methylphenyl)-2-methylthio-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one (6). This intermediate (6) is transformed into the candidate compound (1) by two steps; oxidation, and substitution reaction of the resultant sulfone (7) with 1-acetylpiperazine. This synthetic method is free of chromatographic purification and is amenable to large scale synthesis.
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Notes
  • Solution-Phase Parallel Synthesis of Novel 1,2,3,4-Tetrahydroisoquinolin-1-ones as Anticonvulsant Agents
    Rosaria Gitto, Eleonora Francica, Giovambattista De Sarro, Francesca S ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 181-184
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.181
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    Following our previous studies in the field of anticonvulsant agents, we planned a one-pot solution-phase parallel synthesis (SPPS) of a small library of new 1,2,3,4-tetrahydroisoquinoline derivatives. The activity against audiogenic seizures in DBA/2 mice of the newly synthesized compounds has also been evaluated.
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  • Simple and Rapid UV Spectrophotometry of Caffeine in Tea Coupled with Sample Pre-treatment Using a Cartridge Column Filled with Polyvinylpolypyrrolidone (PVPP)
    Yuji Yamauchi, Akiko Nakamura, Iho Kohno, Miki Kitai, Kirara Hatanaka, ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 185-188
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.185
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    We have applied a sample pre-treatment method with a cartridge column filled with polyvinylpolypyrrolidone (PVPP) to the effective removal of polyphenols and simple UV spectrophotometry of caffeine in tea. The absorption maximum length (λmax) for caffeine was close to those for tea catechins in aqueous 1% acetic acid; therefore, the UV spectrum of a non-treated green tea sample had a large absorption wave. In contrast, the absorbance of the green tea sample was gradually reduced by PVPP cartridge treatment using PVPP from 0 to 50 mg, and was nearly constant using a pre-treatment cartridge with more than 100 mg PVPP, because tea catechins were effectively removed and caffeine was mostly recovered from a green tea sample by means of PVPP cartridge treatment. The PVPP pre-treatment cartridge also removed polyphenols successfully from oolong and black tea samples. Comparison with conventional HPLC analysis indicated that the present pre-treatment method with a PVPP cartridge was useful for the simple and selective UV spectrophotometric determination of caffeine in green, oolong and black tea samples.
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  • Two New Alkaloids from Capparis himalayensis
    Yun-Qiu Li, Shi-Lin Yang, He-Ran Li, Li-Zhen Xu
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 189-191
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.189
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    Two new alkaloids, Capparin A (1) and B (2), along with seven known compounds 6-methoxyindoline-2,3-dione (3), wogonin (4), oroxylin A (5), kaempferol (6), apigenin (7), quercetin (8) and luteolin (9), were isolated from the whole plant of Capparis himalayensis. Their structures have been established on the basis of spectral methods and the structure of 1 was confirmed by X-ray crystallographic analysis.
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  • Two New Coumarins from Herpetospermum caudigerum
    Mei Zhang, Yun Deng, Hong-Bin Zhang, Xiao-Lin Su, Hu-Lan Chen, Tian Yu ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 192-193
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.192
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    The ethyl acetate extract from the seeds of Herpetospermum caudigerum was found to show protective effects on carbon tetrachloride (CCl4) and thioacetamide (TAA)-induced acute hepatic injuries in mice. From the ethyl acetate extract, two new coumarins, herpetolide A (1) and herpetolide B (2), along with four known compounds, herpetone (3), dehydrodiconiferyl alcohol (4), 2,4-dihydroxypyrimidine (5) and stigmasterol (6) were isolated. The structures of the new coumarins were elucidated on the basis of chemical and physicochemical evidences. Herpetone exhibited protective effects on CCl4-induced hepatocyte injury.
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  • Antimycobacterial Activity of Cinnamate-Based Esters of the Triterpenes Betulinic, Oleanolic and Ursolic Acids
    Tanud Tanachatchairatana, John Barnard Bremner, Ratchanaporn Chokchais ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 194-198
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.194
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    Betulinic acid, oleanolic acid and ursolic acid have been modified at the C-3 position to cinnamate-based esters and in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Ra has been determined. The results indicated that modification of the parent structures of betulinic acid, oleanolic acid and ursolic acid to the p-coumarate and, in the case of the latter two triterpenes, the ferulate ester analogues resulted in high antimycobacterial activity. Structure–activity relationships within the lupane, oleanane and ursane analogues and between these triterpenes are discussed.
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  • Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production
    Seong Su Hong, Seon A Lee, Xiang Hua Han, Min Hee Lee, Ji Sang Hwang, ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 199-202
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.199
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    Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.
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  • Triterpenoid Saponins from the Seeds of Pharbitis nil
    Da Young Jung, Hyekyung Ha, Ho Young Lee, Chungsook Kim, Je-Hyun Lee, ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 203-206
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.203
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    From the seeds of Pharbitis nil (Convolvulaceae), two new oleanene-type triterpene glycosides, pharbitosides A (1) and B (2), together with β-sitosterol, β-sitosterol glucoside (daucosterol), caffeic acid, and methyl caffeate were isolated. The structure of pharbitoside A (1) was elucidated to be queretaroic acid 3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (1). Pharbitoside B (2) is a 21α-hydroxyoleanolic acid saponin carrying the same sugar moiety as that of pharbitoside A (1).
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  • New neo-Clerodane Diterpenoid Alkaloids from Scutellaria barbata with Cytotoxic Activities
    Sheng-Jun Dai, Dong-Dong Liang, Yan Ren, Ke Liu, Li Shen
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 207-209
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.207
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    Four new neo-clerodane diterpenoid alkaloids, named scutebarbatines I—L (1—4), were isolated from the whole plant of Scutellaria barbata D. DON. Their structures were established on the basis of detailed spectral analyses. In vitro, the four new compounds showed significant cytotoxic activities against three human cancer lines (HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells), and gave IC50 values in the range 3.2—8.3 μM.
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  • Cytotoxicity of Labdane-Type Diterpenoids from Hedychium forrestii
    Qing Zhao, Chen Qing, Xiao Jiang Hao, Jun Han, Guo Ying Zuo, Cheng Zou ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 210-212
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.210
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    Two new labdane-type diterpenoids, hedyforrestin D (1) and 15-ethoxy-hedyforrestin D (2), and three known compounds, yunnancoronarin A (4), B (3) and C (5) were isolated from the rhizomes of Hedychium forrestii. The structure of the new diterpenoids was established as 6β,15ξ-dihydroxylabda-8(17),11,13-trien-15,16-olide (1), and 6β-hydroxy-15ξ-ethoxylabda-8(17),11,13-trien-15,16-olide (2) on the basis of spectroscopic analyses. In addition, the isolated compounds were evaluated for their cytotoxicity against the lung adenocarcinoma cells A549 and leukemia cells K562 through 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assays. Of these, compounds 3 and 4 exhibited the most activity with IC50 values of 0.92 and 2.20 μM, respectively, whereas 5 was inactive against A549 cells and 1 was inactive against both cell lines up to a concentration of 300.81 μM. This shows that both the hydroxy substitution and orientation of unsaturated lactone group in the five-membered ring of C-13 to C-16 seem to play an important role in the anti-tumor activities of human lung adenocarcinoma and leukemia.
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  • Anticancer Constituents from the Roots of Rubia cordifolia L.
    Jong Keun Son, Soon Ja Jung, Ji Hyun Jung, Zhe Fang, Chong Soon Lee, C ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 213-216
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.213
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    Activity-directed isolation of the methylene chloride fraction of the roots of Rubia cordifolia L. resulted in the identification of a new epoxymollugin (3) and eight known compounds (1, 2, 4—9). The structures of the compounds were elucidated from chemical and spectroscopic evidence. In addition, their topoisomerase I and II inhibitory activities and cytotoxicities were measured.
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  • Penicillenols from Penicillium sp. GQ-7, an Endophytic Fungus Associated with Aegiceras corniculatum
    Zhen-Jian Lin, Zhen-Yu Lu, Tian-Jiao Zhu, Yu-Chun Fang, Qian-Qun Gu, W ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 217-221
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.217
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    Six new tetramic acids derivatives, penicillenols A1, A2, B1, B2, C1, and C2 (1—6), together with citrinin, phenol A acid, phenol A, and dihydrocitrinin, were identified from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum. Their structures were elucidated on the basis of comprehensive spectral analysis. All the new compounds were evaluated for their cytotoxic effects on four cell lines by the MTT method. Penicillenols A1 and B1 showed cytotoxicities against HL-60 cell line with IC50 values of 0.76 μM and 3.20 μM, respectively.
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  • Anti-plasmodial and Cholinesterase Inhibiting Activities of some Constituents of Psorospermum glaberrimum
    Bruno Ndjakou Lenta, Krishna Prasad Devkota, Silvère Ngouela, F ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 222-226
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.222
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    Glaberianthrone (1), a new bianthrone was isolated from the hexane extract of the stem bark of Psorospermum glaberrimum together with thirteen known compounds: 3-geranyloxyemodin anthrone (2), friedelan-3-one (3), 3-prenyloxyemodin anthrone (4), 3-geranyloxyemodin (5), 3-prenyloxyemodin (6), friedelan-3-ol (7), acetylvismione D (8), betulinic acid (9), 2-geranylemodin (10), bianthrone A2b (11), bianthrone 1a (12), emodin (13) and 2-prenylemodin (14). The structures of the isolated compounds were established by means of spectroscopic methods. The extracts and the isolated compounds were tested in vitro for their anti-plasmodial activity against Plasmodium falciparum (chloroquine resistant strain W2) and for their acetyl- and butyrylcholinesterase inhibitory properties. The n-hexane extract showed good anti-plasmodial activity against P. falciparum W2 strain, with IC50 of 0.87 μg/ml. It also exhibited 65.5% and 98.2% of acetyl- and butyrylcholinesterase inhibition at 0.2 mg/ml, respectively. Compounds 2 and 8 showed the best potencies against P. falciparum W2 strain with IC50 of 1.68 μM and 0.12 μM, (0.66 μg/ml and 0.054 μg/ml) respectively. All tested compounds showed good butyrylcholinesterase inhibition activities with compound 12 displaying the best potency (IC50 9.25±0.25 μM). All the tested compounds showed weak inhibitory activity against acetylcholinesterase.
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  • Determination of (R)-Xanthoanthrafil, a Phosphodiesterase-5 Inhibitor, in a Dietary Supplement Promoted for Sexual Enhancement
    Kenichi Kumasaka, Nobuo Kawahara, Kayo Doi, Takashi Kojima, Yukihiro G ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 227-230
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.227
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    We describe here the first case of the finding of xanthoanthrafil, a phosphodiesterase-5 inhibitor, in a dietary supplement. A methanol extract of the supplement product was first analyzed by TLC and HPLC. The results indicated that the extract contained an unknown compound. The molecular weight of the compound was 389 and the accurate mass showed its elemental composition to be C19H23N3O6. Combined with this data, NMR analysis revealed the planar structure of the unknown compound to be N-(3,4-dimethoxybenzyl)-2-(1-hydroxypropan-2-ylamino)-5-nitrobenzamide. The R-configuration of this compound had been synthesized as a phosphodiesterase-5 inhibitor, formerly reported as FR226807 by Fujisawa Pharmaceutical Co., Ltd. The absolute configuration of the isolated compound was estimated to have R-configuration by its optical rotation. Considering its general properties, this compound is renamed as (R)-xanthoanthrafil with the agreement of Astellas Pharma Inc. which is the successor of Fujisawa Pharmaceutical Co., Ltd. Quantitative analysis revealed that the content of (R)-xanthoanthrafil in the product was about 31 mg/capsule.
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  • Further Cytotoxic Sesquiterpene Lactones from Elephantopus mollis KUNTH
    Turibio Kuiate Tabopda, Joseph Ngoupayo, Jiawei Liu, Muhammad Shaiq Al ...
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 231-233
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.231
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    Three new sesquiterpene lactones, (4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (1), (4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (2) and 2,5-epoxy-2β-hydroxy-4α-methoxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (3), have been isolated from roots and stems of Elephantopus mollis together with two known sesquiterpene lactones (4, 5). The identification of the isolates was accomplished by spectroscopic methods. Compounds (1—5) exhibited significant cytotoxic activities against mouse neuroblastoma B104 cells.
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  • Withangulatin I, a New Cytotoxic Withanolide from Physalis angulata
    Shwu-Woan Lee, Min-Hsiung Pan, Chiu-Ming Chen, Zong-Tsi Chen
    Article type: Notes
    2008 Volume 56 Issue 2 Pages 234-236
    Published: February 01, 2008
    Released on J-STAGE: February 01, 2008
    DOIhttps://doi.org/10.1248/cpb.56.234
    JOURNAL FREE ACCESS
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    A new withanolide, withangulatin I (2), was isolated from the whole plant of Physalis angulata. Its structure was established as (20S,22R)-15α-acetoxy-5β,6β-epoxy-14α-hydroxy-1,4-dioxo-witha-2,16,24-trienolide on the basis of chemical and spectroscopic methods including 2D-NMR and circular dichroism (CD) experiments. Withangulatin A (1) and withangulatin I (2) were tested for their cytotoxic activities against two human cancer cell lines, colorectal carcinoma COLO 205 and gastric carcinoma AGS, in vitro. Compounds 1 and 2 exhibited inhibitory activities against these two human cancer cells with IC50 values of 16.6 and 1.8 and 53.6 and 65.4 μM, respectively.
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