Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 54, Issue 10
Displaying 1-27 of 27 articles from this issue
Review
  • Yoshitaka Hamashima
    2006 Volume 54 Issue 10 Pages 1351-1364
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Using the unique character of the chiral Pd complexes 1 and 2, highly efficient catalytic asymmetric reactions have been developed. In contrast to conventional Pd(0)-catalyzed reactions, these complexes function as an acid-base catalyst. Thus active methine and methylene compounds were activated to form chiral palladium enolates, which underwent enantioselective carbon–carbon bond-forming reactions such as Michael reaction and Mannich-type reaction with up to 99% ee. Interestingly, these palladium enolates acted cooperatively with a strong protic acid, formed concomitantly during the formation of the enolates to activate electrophiles, thereby promoting the C–C bond-forming reaction. This palladium enolate chemistry was also applicable to electrophilic enantioselective fluorination reactions, and various carbonyl compounds including β-ketoesters, β-ketophosphonates, tert-butoxycarbonyl lactone/lactams, cyanoesters, and oxindole derivatives could be fluorinated in a highly enantioselective manner (up to 99% ee). Using this method, the catalytic enantioselective synthesis of BMS-204352, a promising anti-stroke agent, was achieved. In addition, the direct enantioselective conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compound was successfully demonstrated. In this reaction, combined use of the Pd complex 2 having basic character and the amine salt was the key to success, allowing controlled generation of the nucleophilic free amine. This aza-Michael reaction was successfully applied to asymmetric synthesis of the CETP inhibitor torcetrapib.
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Regular Articles
  • Jong-Hyun Lee, Naoko Kiyota, Tsuyoshi Ikeda, Toshihiro Nohara
    2006 Volume 54 Issue 10 Pages 1365-1369
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Paprika and Jalapeño are used as vegetables and spices. We have obtained six new acyclic diterpene glycosides, called capsianosides XIII (2), XV (3), IX (4), XVI (5), X (6) and VIII (7) together with known capsianoside II (1) from the fruits of the Paprika and Jalapeño. The structures of these compounds have been elucidated by the 1H- and 13C-NMR spectra and two-dimensional NMR methods.
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  • Yukinori Miyaichi, Akiko Segawa, Tsuyoshi Tomimori
    2006 Volume 54 Issue 10 Pages 1370-1379
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    From the whole herb of Leucas cephalotes SPRENG., new labdane-, norlabdane- and abietane-type diterpenes named leucasdins A (1), B (2) and C (3), respectively, and two protostane-type triterpenes named leucastrins A (4) and B (5) were isolated, together with a known triterpene, oleanolic acid, five sterols, 7-oxositosterol, 7-oxostigmasterol, 7α-hydroxysitosterol, 7α-hydroxystigmasterol and stigmasterol, and eight flavones, 5-hydroxy-7,4′-dimethoxyflavone, pillion, gonzalitosin I, tricin, cosmosin, apigenin 7-O-β-D-(6-O-p-coumaroyl)glucopyranoside, anisofolin A and luteolin 4′-O-β-D-glucuronopyranoside. The structures of 1—5 were determined as (3S,6R,8R,9R,13S,16S)-9,13,15,16-bisepoxy-3,16-diacetoxy-6-formyloxylabdane, (3S,6R)-3-acetoxy-6-formyloxy-iso-ambreinolide, (4R,9S,12R,13R)-12,13-dihydroxyabiet-7-en-18-oic acid, (3S,17S,20S,24S)-3,20-dihydroxy-24-methylprotost-25-en, and (3S,17S,20S,24S)-3,20,24-trihydroxyprotost-25-en respectively, based on spectral and chemical data.
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  • Bo Liang, Jing-Kui Tian, Li-Zhen Xu, Shi-Lin Yang
    2006 Volume 54 Issue 10 Pages 1380-1383
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Three new saponins were isolated from the whole plants of Lysimachia davurica. On the basis of 1D and 2D NMR (1H–1HCOSY, HMBC, HMQC, and TOCSY) techniques, MS, and hydrolysis, their structures were found to be 3-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl-13,28-epoxy-3β-hydroxy-16-oleanaone (1), 3-O-β-D-glucopyranosyloxyuronic acid-(1→2)-β-D-xylopyranosyl-cyclamiretin A (2), and 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-cyclamiretin A (3), respectively. Compounds 2 and 3 showed significant cytotoxicities against human A-2780 cells.
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  • Narayana Subbiah Hari Narayana Moorthy, Rahul Jitendra Singh, Hemendra ...
    2006 Volume 54 Issue 10 Pages 1384-1390
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized compounds. The results of the antibacterial studies shows that compounds 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compound (2h) has remarkable activity against all strains viz. 25 μg/ml inhibitory concentration against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compound 2f possess minimum inhibitory concentration of 200 μg/ml against E. coli and S. typhimurium and 25 μg/ml against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compounds were performed and the predicted result showed that the compound having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivatives undergo demethylation reaction. The biologically active compounds are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.
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  • Abdolmajid Bayandori Moghaddam, Mohammad Reza Ganjali, Parviz Norouzi, ...
    2006 Volume 54 Issue 10 Pages 1391-1396
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    This is an environmentally friendly method in the field of electroorganic reactions under controlled potential electrolysis, without toxic reagents at a carbon electrode in an undivided cell which involves the (EC) mechanism reaction and comprises two steps alternatively; (i) electrochemical oxidation and (ii) chemical reaction. In particular, the electrochemical oxidation of 4-tert-butylcatechol, 4-methylcatechol and 2,3-dihydroxybenzoic acid in the presence of 2-phenyl-1,3-indandione has been studied in a water–acetonitrile (90 : 10) mixture. The research includes the use of a variety of experimental techniques, such as cyclic voltammetry, controlled-potential electrolysis, and spectroscopic identification of products (FT-IR, 1H-NMR, and MS spectrometry).
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  • Hideko Inoue, Tomoyuki Yamada, Hirokazu Nakayama, Mitsutomo Tsuhako
    2006 Volume 54 Issue 10 Pages 1397-1402
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Phosphorylation of several D-glucose derivatives has been achieved using inorganic monoimido-cyclo-triphosphate (MCTP, Na3P3O8NH) in aqueous solution. In the phosphorylation of D-glucose, D-glucuronic acid, 2-deoxy-D-glucose and D-galactose, 1-O-diphosphoramidophosphono-β-D-glucose, 1-O-diphosphoramidophosphono-β-D-glucuronic acid, 1-O-diphosphoramidophosphono-2-deoxy-β-D-glucose, and 1-O-diphosphoramidophosphono-β-D-galactose were stereoselectively synthesized with yields of 54, 32, 37 and 46%, respectively. In the case of methyl α-D-glucoside, the phosphorylated products were methyl 3-O-diphosphoramidophosphono-α-D-glucoside and methyl 4-O-diphosphoramidophosphono-α-D-glucoside, and in the case of methyl β-D-glucoside the products were methyl 2-O-diphosphoramidophosphono-β-D-glucoside, methyl 3-O-diphosphoramidophosphono-β-D-glucoside, and methyl 4-O-diphosphoramidophosphono-β-D-glucoside. For D-mannose and D-allose, several phosphorylated products were obtained and the main products were 1-O-diphosphoramidophosphono-β-D-aldoses.
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  • Katsuyoshi Matsunami, Ichiko Takamori, Takakazu Shinzato, Mitsunori Ar ...
    2006 Volume 54 Issue 10 Pages 1403-1407
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Four new megastigmane glucosides, named macarangiosides A—D (2—5), together with mallophenol B, lauroside E, methyl brevifolin carboxylate, and hyperin and isoquercitrin as a mixture were isolated from the leaves of Macaranga tanarius (L.) MÜLL.-ARG. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. Macarangioside A—C (2—4) and mallophenol B were galloylated on glucose moiety and possessed the potent 2,2-diphenyl-picrylhydrazyl (DPPH) radical-scavenging activity.
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  • Takeshi Isoda, Itsuki Yamamura, Satoshi Tamai, Toshio Kumagai, Yoshimi ...
    2006 Volume 54 Issue 10 Pages 1408-1411
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    An orally active carbapenem L-084, which exhibits high bioavailability in humans, has a 1-(1,3-thiazolin-2-yl)azetidin-3-ylthio moiety at the C-2 position of the 1β-methylcarbapenem skeleton. We established a practical and cost-effective synthesis of 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine (1) for further scale-up production of L-084. This synthesis method entails an industry-oriented reaction of azetidine ring-closure to yield N-benzyl-3-hydroxyazetidine (16), which is eventually converted to 1 via key intermediates, Bunte salts 19 and 20.
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  • Masahiro Tada, Kosaku Ishimaru
    2006 Volume 54 Issue 10 Pages 1412-1417
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    A quinone methide diterpene: abietaquinone methide, which possesses potent anti-methicillin-resistant Staphylococcus aureus (MRSA) and anti-vancomycin-resistant Enterococcus (VRE) activities, was synthesized via efficiently ortho-oxidation of ferruginol derived from industrially available dehydroabietic acid. ortho-Oxidation of phenols was developed to give mono esters of catechols using a stable diacyl peroxide, bis(4-chlorobenzoyl) peroxide (m-chlorobenzoyl peroxide: mCBPO) which was synthesized from meta-chlorobenzoic acid. Efficient one pot ortho-oxidation reaction of phenol with an adduct of meta-chloroperbenzoic acid (mCPBA) with dicyclohexylcarbodiimide (DCC) was also reported.
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Notes
  • Pilar Canoa, María J. González-Moa, Marta Teijeira, Carm ...
    2006 Volume 54 Issue 10 Pages 1418-1420
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Novel nucleoside analogues of structure 3—5 were synthesized starting from (±)-cis-2-amino-3-cyclopentenylmethanol (1). The chlorine derivative 3 inhibited both HIV-1 and HIV-2 replication in MT-4 cells with IC50 values of 10.67 μM and of 13.79 μM, respectively.
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  • Masateru Ono, Kanna Oishi, Hiroaki Abe, Chikako Masuoka, Masafumi Okaw ...
    2006 Volume 54 Issue 10 Pages 1421-1424
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Two new iridoid glucosides, verbenabraside A (1) and verbenabraside B (2), were isolated from the aerial parts of Verbena brasiliensis VELL., along with six known iridoid glucosides, gelsemiol 3-O-β-D-glucoside (3), verbraside (4), 9-hydroxysemperoside (5), griselinoside (6), aralidioside (7), and 6α-hydroxyforsythide dimethyl ester (8), three known phenylethanoid glycosides, 2-phenylethyl O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside (9), acteoside (10), and leucosceptoside A (11), two known lignan glucosides, dihydroxymethyl-bis(3,5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9 (or 9′)-O-β-glucopyranoside (12) and (+)-lyoniresinol 3α-O-β-D-glucopyranoside (13), a known methyl salicylate glucoside, methyl 2-O-β-D-glucopyranosylbenzoate (14), and two known sterols, β-sitosterol 3-O-β-D-glucopyranoside (15) and β-sitosterol (16). Their chemical structures were determined on the basis of spectroscopic data. Compound 1 exhibited stronger scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl than that of α-tocopherol.
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  • Dianpeng Li, Tsuyoshi Ikeda, Nanae Matsuoka, Toshihiro Nohara, Hourui ...
    2006 Volume 54 Issue 10 Pages 1425-1428
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA1 (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA1 (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-α-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-α-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits.
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  • André Pichette, Serge Lavoie, Pierre Morin, Vakhtang Mshvildadz ...
    2006 Volume 54 Issue 10 Pages 1429-1432
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Two new labdane diterpenes, cis-19-hydroxyabienol (1) and 8α-hydroxy-12Z,14-labdadien-19-al (2), along with another labdane described for the first time in the genus Larix, 19-acetoxy-13S-hydroxy-8(17),14-labdadiene (3) and a stilbene, 3-methoxy-3,3′,5′-trihydroxystilbene (4), were isolated from the stem bark of Larch (Larix laricina). Their structures were established by standard chemical and spectroscopic methods. Compounds 2 and 3 were shown to be moderately cytotoxic against A-549, DLD-1 and normal skin fibroblast cell lines, WS1. Compound 1 was found to be selectively active against colon carcinoma cell lines, DLD-1.
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  • Umalee Namdaung, Nuntana Aroonrerk, Sunit Suksamrarn, Kannawat Danwise ...
    2006 Volume 54 Issue 10 Pages 1433-1436
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Investigation of the chemical constituents of the root bark of Artocarpus rigidus BLUME subsp. rigidus has led to the isolation of six, structurally diverse phenolic compounds. These included two new compounds with modified skeletons, the flavonoid 7-demethylartonol E (1) and the chromone artorigidusin (2), together with four known phenolic compounds, the xanthone artonol B (3), the flavonoid artonin F (4), the flavonoid cycloartobiloxanthone (5), and the xanthone artoindonesianin C (6). Compounds 1, 4, and 5 exhibited antiplasmodial activity against Plasmodium falciparum. All compounds showed antimycobacterial activity against Mycobacterium tuberculosis, with 4 being the most active compound (MIC 6.25 μg/ml). Compounds 5 and 6 were active against KB cells, whereas 2, 5, and 6 showed varying toxicity to BC cells. Compounds 1—3, 5, and 6 were active in the NCI-H187 cytotoxicity assay, with 3 being the most active compound (IC50 1.26 μg/ml).
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  • Aun Chea, Sotheara Hout, Christophe Long, Laurence Marcourt, Robert Fa ...
    2006 Volume 54 Issue 10 Pages 1437-1439
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Two new sesquiterpene lactones, vernolides C and D as well as six known ones were isolated from the dichloromethane fraction of an aqueous extract from Vernonia cinerea. Their structures were elucidated by spectroscopic methods. Among the known sesquiterpene lactones, three of them were described in this plant for the first time. In vitro antiplasmodial evaluation showed that the three major compounds 1, 7 and 8 were active against chloroquine resistant Plasmodium falciparum strain (W2) with IC50 3.9, 3.7 and 3.5 μM, respectively.
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  • Kun Zou, Junzhi Wang, Ming Du, Qing Li, Guangzhong Tu
    2006 Volume 54 Issue 10 Pages 1440-1442
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    A pair of diastereoisomeric steroidal saponins were obtained from the saponin fraction (SF) of methanol extracts from Tupistra chinensis rhizomes, collected in Shennongjia Forest District, China. Based on the chemical and spectroscopic evidences, their structures were determined as shown in Fig. 1. The sample SF displayed marked inhibitory action in vitro towards HeLa and HL-60 cancer cell lines at 10 μg/ml by MTT method.
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  • Wei Ni, Yan Hua, Hai-Yang Liu, Rong-Wei Teng, Yun-Cheung Kong, Xiu-Yin ...
    2006 Volume 54 Issue 10 Pages 1443-1446
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Six new tirucallane-type triterpenoid saponins, sapimukosides E—J (1—6) were isolated from the roots of Sapindus mukorossi GAERTN. Their structures were elucidated by a combination of spectral and chemical analysis.
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  • Samah Sayed Abbas, Yasmin Mohamed Fayez, Laila El-Sayed Abdel Fattah
    2006 Volume 54 Issue 10 Pages 1447-1450
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Stability indicating assays for determination of Donepezil Hydrochloride in presence of its oxidative degradate were developed and validated. The first three are spectrophotometric methods depending on using zero order (D0), first order (D1) and second order (D2) spectra. The absorbance was measured at 315 nm for (D0) while the amplitude was measured at 332.1nm for (D1) and 340 nm for (D2) using deionized water as a solvent. Donepezil Hydrochloride (I) can be determined in the presence of up to 70% of its oxidative degradate (II) using (D0), 80% using (D1) and 90% using (D2). The linearity range was found to be 8—56 μg ml−1 for (D0), (D1) and (D2). These methods were applied for the analysis of I in both powder and tablet form. Also, a spectrofluorimetric method depending on measuring the native fluorescence of I in deionized water using λ excitation 226 nm and λ emission 391 nm is suggested. The linearity range was found to be 0.32—3.20 μg ml−1 using this method, I was determined in the presence of up to 90% of II. The proposed method was applied for the analysis of I in tablet form as well as in human plasma. The last method depends on using TLC separation of I from its oxidative degradate II and I was then determined spectrodensitometrically. The mobile phase was methanol : chloroform : 25% ammonia (16 : 64 : 0.1 by volume). The linearity range was found to be 2—15 μg/spot. This method was applied to the analysis of I in both powder and tablet form using acetonitrile as a solvent.
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  • Jun Li, Xiaoli Bi, Guohua Zheng, Yoshimitsu Hitoshi, Tsuyoshi Ikeda, T ...
    2006 Volume 54 Issue 10 Pages 1451-1454
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Two new steroidal glycosides named riparosides A (1) and B (2), and two aromatic compounds (3, 4), together with four known flavonoid derivatives have been isolated from the EtOH extract of the rhizomes and roots of Smilax riparia A. DC. The structure of riparoside A (1) was determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl 3β,20α-dihydroxy-5α-furost-22(23)-ene 26-O-β-D-glucopyranoside. Riparoside B (2) was characterized as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl 3β,16β-dihydroxy-5α-pregnan-20-one 16-O-[5-O-β-D-glucopyranosyl 5-hydroxy-4-methyl-pentanoic acid]-ester 26-O-β-D-glucopyranoside. Compounds 3 and 4 were elucidated as a sucrosyl ferulic acid ester and 7-O-methyl-10-oxythymol gentiobioside, respectively.
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  • Yu-Zhi Zhou, Hong-Yu Ma, Huan Chen, Li Qiao, Yao Yao, Jia-Qing Cao, Yu ...
    2006 Volume 54 Issue 10 Pages 1455-1456
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Two new acetylenic glucosides, 4′,6′-acetonide-8Z-decaene-4,6-diyne-1-O-β-D-glucopyranoside named carthamoside A1 (1) and 4,6-decadiyne-1-O-β-D-glucopyranoside named carthamoside A2 (2), along with one known acetylenic glucoside, 8Z-decaene-4,6-diyne-1-O-β-D-glucopyranoside (3), have been isolated from the air-dried flower of Carthamus tinctorius, these structures have been identified on the basis of spectroscopic methods.
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  • Shin-ichi Hirashima, Akichika Itoh
    2006 Volume 54 Issue 10 Pages 1457-1458
    Published: 2006
    Released on J-STAGE: October 01, 2006
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    Aldehydes were found to be oxidized to the corresponding carboxylic acid in the presence of catalytic lithium bromide under photo-irradiation.
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  • Yi Zhang, An Liu, Zu Guang Ye, Jia Lin, Li Zhen Xu, Shi Lin Yang
    2006 Volume 54 Issue 10 Pages 1459-1461
    Published: 2006
    Released on J-STAGE: October 01, 2006
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    The natural antitumor product (−)-zeylenone was prepared for the first time in a stereoselective synthesis from shikimic acid.
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  • Takashi Maoka, Naoshige Akimoto
    2006 Volume 54 Issue 10 Pages 1462-1464
    Published: 2006
    Released on J-STAGE: October 01, 2006
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    A new carotenoid with a 2-hydroxy-4-oxo-β-end group was isolated from the hermit crab, Paralithodes brevipes, as a minor component. Its structure was determined to be 2,3′-dihydroxy-β,β-carotene-4,4′-dione (1) by spectral data and the compound was named 2,3′-dihydroxycanthaxanthin. Chiral resolution of 1 by HPLC using a chiral column provided two stereoisomers, 1a and 1b. The 3′R and 3′S chirality were determined for 1a and 1b, respectively, by CD spectra.
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  • Mamoru Fukuda, Emika Ohkoshi, Mitsuko Makino, Yasuo Fujimoto
    2006 Volume 54 Issue 10 Pages 1465-1468
    Published: 2006
    Released on J-STAGE: October 01, 2006
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    A new sesquiterpene, named baccharisketone (1), and a new monoterpene, p-methoxythymol acetate (2), were isolated from the leaves of Baccharis dracunculifolia along with seventeen known compounds (3—19). The structures of the new compounds were determined by spectroscopic means. The growth inhibitory activity of the isolated compounds against leukemia cells (L 1210) was tested and three terpene phenols (4, 6, 17) and five sesquiterpene alcohols (8, 10, 11, 13, 16) were found to exhibit strong cytotoxic activity.
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  • Naoto Fukutsu, Yuich Sakamaki, Takao Kawasaki, Koichi Saito, Hiroyuki ...
    2006 Volume 54 Issue 10 Pages 1469-1472
    Published: 2006
    Released on J-STAGE: October 01, 2006
    JOURNAL FREE ACCESS
    Cross-contamination is a critical issue for pharmaceutical manufacturing, especially for β-lactam antibiotics. Thus, an analytical method for the simultaneous determination of β-lactam antibiotics cefmetazole (CMZ) and cefpodoxime proxetil (CPDXPR) contaminants in non-β-lactam pharmaceuticals was developed using high-performance liquid chromatography-tandem mass spectrometry. The developed method was found to be sensitive at the detection limit of 0.002 ppm for both compounds. Mean recoveries of CMZ and CPDXPR from olmesartan medoxomil (OLM) tablets were 96.7 to 102.2% and 88.9 to 94.2%, respectively. The developed method was successfully applied for the verification of CMZ and CPDXPR contamination to actually manufactured OLM tablets.
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  • Shizue Echigo, Noriyuki Hara, Gladys Jeanette Carderon, Carmenza Duque ...
    2006 Volume 54 Issue 10 Pages 1473-1477
    Published: 2006
    Released on J-STAGE: October 01, 2006
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    The C-24 configuration of (22E,24ξ)-24-isopropenyl-22-dehydrocholesterol (1), which was recently isolated from the Colombian Caribbean sponge, Topsentia ophiraphidites, was investigated. Synthesis of the stereodefined (24R)- and (24S)-(22E)-24-isopropenyl-22-dehydrocholesterols (1a, 1b) followed by 1H- and 13C-NMR data comparison of these sterols established the (24R)-configuration of 1. In addition, (24R)- and (24S)-24-isopropenylcholesterols (2a and 2b) were also synthesized and their NMR data are provided. The C-24 configurations of the samples of 24-isopropenylcholesterol reported previously are discussed.
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