Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 49, Issue 5
Displaying 1-31 of 31 articles from this issue
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Reviews
  • Multifunctional Asymmetric Catalysis
    Masakatsu SHIBASAKI, Motomu KANAI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 511-524
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.511
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    Two types of general and practical enantioselective catalysts, namely, bimetallic complexes and Lewis acid-Lewis base bifunctional catalysts were developed based on the concept of multifunctional catalysis. In the first part of this review, the first example of a catalytic enatioselective nitro-Mannich reaction as well as a direct catalytic enantioselective aldol reaction of 2-hydroxyacetophenone using bimetallic complexes is discussed. The new complex, composed of ytterbium, potassium, and BINOL in a ratio of 1:1:3, promoted the nitro-Mannich reaction of nitromethane with up to 91% ee. On the other hand, second generation ALB catalyzed an enantioselective and diastereoselective nitro-Mannich reaction of nitroalkanes in up to 83% ee with a diastereomeric ratio up to 7:1. Moreover, the reaction of aldehydes with 2-hydroxyacetophenone in the presence of LLB, KHMDS, and H2O selectively gave the corresponding anti-α, β-dihydroxy ketones in up to 95% ee and, in the presence of the catalyst prepared from linked-BINOL and 2 eq of Et2Zn, selectively afforded the syn-α, β-dihydroxy ketones in up to 86% ee. In the second part, the development of new catalysts displaying a Lewis acidity and a Lewis basicity is described. The Lewis acid of the catalyst activates aldehydes, imines, acyl quinoliniums, and ketones. At the same time, the Lewis base activates the nucleophile (TMSCN). Catalysts of this type produced a highly enantioselective cyanation of these electrophiles. Application of the catalytic enantioselective cyanosilylation of aldehydes to a total synthesis of epothilones is also described.
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Regular Articles
  • Evaluation of New Pregnane Derivatives as 5α-Reductase Inhibitor
    Marisa CABEZA, Ivonne HEUZE, Eugene BRATOEFF, Elena RAMIREZ, Rosa MART ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 525-530
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.525
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    The objective of this study was to synthesize several new pregnane derivatives and evaluate them as antiandrogens. From the commercially available 16-dehydropregnenolone acetate (7), two new steroidal compounds were synthesized: 17α-hydroxy-17β-methyl-16β-phenyl-D-homoandrosta-1, 4.6-triene-3, 20-dione (18) and 17α-acetoxy-17β-methyl-16β-phenyl-D-homoandrosta-1, 4.6-triene-3, 20-dione (19). The 5α-reductase inhibitory effect of the new compounds 18 and 19 together with the previously synthesized intermediates 7, 8, 13, 16, and 17 was determined in three different models: gonadectomized hamster flank organs diameter size, incorporation of [1, 2-14C]sodium acetate into lipids in flank organs and conversion of [3H]testosterone (T) to [3H]dihydrotestosterone (DHT) by Penicillium crustosum. The evaluation of these steroids was carried out with three different controls: one group was treated with vehicle, the second with T and the third group with T plus finasteride. The pharmacological results from this work demonstrated that T significantly increases the diameter of the pigmented spot on the flank organs (p<0.05) as well as the incorporation of labeled sodium acetate into lipids in gonadectomized hamster flank organs (from 0.125 to 0.255 nmol per gland). In this study we also observed that broth of Penicillium crustosum converted [3H]T to [3H]DHT in a manner comparable to that of the flank organs. All experiments indicated that finasteride as well as steroids 7, 8, 13, 16-19 reduced significantly the conversion of T to DHT in P. crustosum. These compounds also decrease the size of the pigmented spot in the flank organs as well as reducing the incorporation of radiolabeled sodium acetate into lipids; T and the control sample (treated with vehicle only) were used for comparison. Apparently the presence of the 4, 6-diene-3, 20-dione moiety and also the C-17 ester group produce a higher inhibitory effect on the parameters used. PPThe data from this study indicated also that the three models used for the pharmacological evaluation exhibited comparable results.
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  • Chemical Conversion of Cyclic α-Amino Acids to Cyclic α-Aminophosphonic Acids
    Mamoru KANAME, Hironori MASHIGE, Shigeyuki YOSHIFUJI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 531-536
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.531
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    The oxidative decarboxylation of cyclic α-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb(OAc)4] gave 2-hydroxy derivatives, which were transformed into the corresponding α-aminophosphonic acid esters by treatment of trialkyl phosphites in the presence of Lewis acids. Deprotection and ester cleavage of the products in the usual manner afforded cyclic α-aminophosphonic acids. The convenient chemical conversion of five- and six-membered cyclic α-amino acids to the corresponding cyclic α-aminophosphonic acids has been accomplished.
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  • New Phenolic Constituents from the Fruit Juice of Phyllanthus emblica
    Ying-Jun ZHANG, Takashi TANAKA, Chong-Ren YANG, Isao KOUNO
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 537-540
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.537
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    Six new phenolic constituents, L-malic acid 2-O- (1), mucic acid 2-O- (5), mucic acid 1, 4-lactone 2-O- (6), 5-O- (8), 3-O- (10), and 3, 5-di-O- (11) gallates, were isolated from the fruit juice of Phyllanthus emblica together with their methyl esters (2-4, 7, 9), and their structures were determined by spectral and chemical methods. Compounds 5, 6, and 8, the major phenolic constituents of the juice, were present as an equilibrium mixture in aqueous solution.
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  • The Mechanism of Reaction of Ebselen with Superoxide in Aprotic Solvents as Examined by Cyclic Voltammetry and ESR
    Tetsuya ARAKI, Hiroaki KITAOKA
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 541-545
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.541
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    The mechanism of the redox reaction of ebselen with superoxide was investigated using both ESR and electrochemical techniques. The reaction with superoxide in aprotic solvents was followed by means of cyclic voltammetry and ESR spin-trapping. A decrease in the oxidation current due to superoxide as a result of the addition of ebselen was clearly observed in the cyclic voltammograms. Ebselen reduced the ESR signal intensity of 5, 5-dimethyl-1-pyrroline N-oxide (DMPO)-superoxide in a dose-dependent manner. The formation of an amidyl radical in this redox reaction was confirmed by rapid mixing continuous-flow ESR. The selenonate form and the seleninate form of ebselen were identified as the final products of the reaction of ebselen with superoxide. The following mechanism for this redox reaction can be proposed: First, ebselen reacts with superoxide and is converted to an ebselen anion radical; second, the ebselen anion radical reacts with superoxide and is converted to the amidyl radical. Hydrogen abstraction by the amidyl radical occurs and gives both a seleninate form and a selenonate form.
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  • Kaempferol Acetylrhamnosides from the Rhizome of Dryopteris crassirhizoma and Their Inhibitory Effects on Three Different Activities of Human Immunodeficiency Virus-1 Reverse Transcriptase
    Byung-Sun MIN, Miyuki TOMIYAMA, Chao-Mei MA, Norio NAKAMURA, Masao HAT ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 546-550
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.546
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    Three new kaempferol glycosides, called crassirhizomosides A (1), B (2) and C (3), were isolated from the rhizome of Dryopteris crassirhizoma (Aspidiaceae), together with the known kaempferol glycoside, sutchuenoside A (4). The structures of 1-3 were determined as kaempferol 3-α-L-(2, 4-di-O-acetyl)rhamnopyranoside-7-α-L-rhamnopyranoside, kaempferol 3-α-L-(3, 4-di-O-acetyl)rhamnopyranoside-7-α-L-rhamnopyranoside, and kaempferol 3-α-L-(2, 3-di-O-acetyl)rhamnopyranosside-7-α-L-rhamnopyranoside, respectively, by chemical and spectroscopic means. Inhibitory effects of 1-4 and kaempferol on human immunodeficiency virus reverse transcriptase-associated DNA polymerase (RNA-dependent DNA polymerase and DNA-dependent DNA polymerase) and RNase H activities were investigated.
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  • Studies on the Constituents of Bark of Parameria laevigata MOLDENKE1)
    Kohei KAMIYA, Chiharu WATANABE, Hanani ENDANG, Mansur UMAR, Toshiko SA ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 551-557
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.551
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    One new trimeric proanthocyanidin, epicatechin-(2β→O→7, 4β→6)-epicatechin-(2β→O→7, 4β→8)-epicatechin (5) and two new tetrameric proanthocyanidins, epicatechin-(2β→O→7, 4β→8)-[epicatechin-(4β→6)]-epicatechin-(4β→8)-epicatechin, named as parameritannin A-1 (6), and epicatechin-(2β→O→5, 4β→6)-[epicatechin-(2β→O→7, 4β→8)]-epicatechin-(4β→8)-epicatechin, named as parameritannin A-2 (7), have been isolated from the bark of Parameria laevigata Moldenke (Apocynaceae) along with the two known dimers, proanthocyanidin A-2 (1) and proanthocyanidin A-6 (2), and two trimers, cinnamtannin B-1 (3) and aesculitannin B (4). These structures were elucidated by spectral and chemical evidence.
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  • A New Synthesis of N-Alkyl 4-Methyl-1, 4-dihydropyridines Utilizing sec-Aminodienyl Esters with Crotonaldehyde
    Takeshi KOIKE
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 558-562
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.558
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    The reactions of sec-aminodienyl esters 3 with crotonaldehyde (4) afforded N-alkyl 3-[2-(methoxycarbonyl)ethenyl]-4-methyl-1, 4-dihydropyridines 5, providing a new azaelectrocyclization reaction.
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  • A Novel Series of Thromboxane A2 Synthetase Inhibitors with Free Radical Scavenging and Anti-peroxidative Activities
    Shoji KAMIYA, Hiroaki SHIRAHASE, Shohei NAKAMURA, Mamoru KANDA, Hirosh ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 563-571
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.563
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    A novel series of indoline derivatives with imidazole and carboxyl moieties were synthesized and evaluated for their thromboxane A2 (TXA2) synthetase inhibiting, radical scavenging and anti-peroxidative activities. Among the compounds synthesized, 3-{5-substituted-3-[2-(imidazol-1-yl)ethyl]indolin-1-yl}propionic acids showed free radical scavenging activity and inhibitory effects on lipid-peroxidation of rat brain homogenate and on arachidonate-induced TXA2-dependent aggregation of rabbit platelets. The anti-platelet and anti-peroxidative activities were related to the lipophilicity of the 5-substituent. The 5-hexyloxy derivative (13) showed about 35-fold higher inhibitory activity on TXA2 synthesis than that of ozagrel and about 100-fold higher activity on lipid peroxidation than that of α-tocopherol. Compound 13 showed in vivo anti-thrombotic effect in mice and ex vivo anti-peroxidative activity in rats.
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  • Antimalarial and Cytotoxic Activities of Bicyclo[6.4.0]dodecenones
    Hiroshi FUJISHIMA, Hiroshi TAKESHITA, Masahiro TOYOTA, Hye-Sook KIM, Y ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 572-575
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.572
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    Biological evaluations of bicyclo[6.4.0]dodecenone derivatives on antimalarial activity in vitro against Plasmodium falciparum and cytotoxicity against human KB cells were made. (±)-(1R*, 4S*, 7R*, 8S*)-4-tert-Butyldimethylsiloxy-5, 5-dimethyl-1-methyl-9-methylene-7-phenylsulfonylbicyclo[6.4.0]dodec-2, 11-dien-10-one (15) exhibited potent antimalarial activity, whereas (±)-(1R*, 7R*, 8S*)-1-methyl-9-methylene-7-phenylsulfonylbicyclo[6.4.0]dodec-2, 11-dien-10-one (14) showed significant cytotoxic activity in human KB cells. Both 14 and 15 possess, as a structural character, the exo-methylene moiety in their 6-membered ring of the 8-6 fused ring system.
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  • Electron Paramagnetic Resonance Study on Free Radical Scavenging and/or Generating Activity of Dopamine-4-O-sulfate
    Kazuyoshi KIRIMA, Koichiro TSUCHIYA, Masanori YOSHIZUMI, Taisuke KAMED ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 576-580
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.576
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    The free radical scavenging and/or generating activity of dopamine-4-O-sulfate was examined and compared with that of dopamine. In humans, dopamine mostly exists in two isomeric forms of sulfate ester conjugates as metabolites; i.e., dopamine-3-O-sulfate and dopamine-4-O-sulfate in the circulation. Dopamine is generally believed to be oxidized by molecular oxygen or another reactive oxygen species under physiological conditions, to form oxidized dopamine derivatives that are cytotoxic. However, it is not known whether dopamine conjugates are generated on interaction with reactive oxygen species or not. In the present study, we measured the susceptibility to oxidization of dopamine-4-O-sulfate by using electron paramagnetic resonance (EPR) spectroscopy and optical absorption spectrometry. Dopamine was easily oxidized and dopamine-derived radicals appeared, whereas dopamine-4-O-sulfate was not oxidized under physiological conditions. Furthermore, dopamine-4-O-sulfate did not react with a strong oxidizing agent, sodium periodate. These results suggest that dopamine-4-O-sulfate has resistance against autoxidation, and seems to be a stable metabolite of dopamine.
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  • New Cyclopropyl-Triterpenoids from the Aerial Roots of Ficus microcarpa
    Yi-Ming CHIANG, Jen-Kuan SU, Yi-Hung LIU, Yueh-Hsiung KUO
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 581-583
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.581
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    Four new cyclopropyl-triterpenes, 27-nor-3β-hydroxy-25-oxocycloartane (1), (22E)-25, 26, 27-trinor-3β-hydroxycycloart-22-en-24-al (2), 3β-acetoxy-15α-hydroxy-13, 27-cyclours-11-ene (3), 3β-acetoxy-12α-formyloxy-13, 27-cycloursan-11α-ol (4), together with (23E)-27-nor-3β-hydroxycycloart-23-en-25-one (5) were isolated from the aerial roots of Ficus microcarpa. Compounds 3 and 4 are rare 13, 27-cycloursane-type triterpenes. Their structures were elucidated by spectroscopic and chemical methods.
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  • Water-Soluble Constituents of Glehnia littoralis Fruit
    Toru ISHIKAWA, Yukiko SEGA, Junichi KITAJIMA
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 584-588
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.584
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    From the water-soluble portion of the methanol extract of the fruit of Glehnia littoralis Fr. SCHMIDT ex MIQ. (Umbelliferae; “hamabofu” in Japanese), thirty compounds, including three new monoterpenoids and a new monoterpenoid glucoside, a new benzofuran glucoside, a new alkyl glucoside, and a new glucide, were obtained. Their structures were clarified by spectral investigation.
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  • New Sterols and Triterpenoids from Four Edible Mushrooms1)
    Yasunori YAOITA, Kaori MATSUKI, Takeyoshi IIJIMA, Satomi NAKANO, Rie K ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 589-594
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.589
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    Four edible mushrooms, Panellus serotinus, Lepista nuda, Tricholoma matsutake and Naematoloma sublateritium, have been investigated chemically. Two new sterols, 5α, 9α-epidioxy-(22E)-ergosta-7, 22-diene-3β, 6α-diol (1) and 5α, 9α-epidioxy-(22E)-ergosta-7, 22-diene-3β, 6β-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lepista nuda. A new sterol, 3β, 5α, 9α, 14β-tetrahydroxy-(22E)-ergosta-7, 22-dien-6-one (3), and compound 2 have been isolated from Tricholoma matsutake. Three new triterpenoids, sublateriols A-C (4-6), have been isolated from Naematoloma sublateritium. The structures of the new compounds were elucidated on the basis of their spectral data.
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  • [title in Japanese]
    Wenzhe FAN, Yasuhiro TEZUKA, Shigetoshi KADOTA
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 595-600
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.595
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    [in Japanese]
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  • Diels-Alder Reactions of Nitro-2(1H)-pyridones with 2, 3-Dimethyl-1, 3-butadiene
    Reiko FUJITA, Kazuhiro WATANABE, Yasuhiro NISHIUCHI, Rumiko HONDA, His ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 601-605
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.601
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    Diels-Alder (DA) reactions of 3- or 5-nitro-2(1H)-pyridones and nitro-2(1H)-pyridones containing a methoxycarbonyl group with 2, 3-dimethyl-1, 3-butadiene were examined. The DA reactions of 3-nitro-2(1H)-pyridones in this paper represent, to the best of our knowledge, the first report of DA reactions of 3-substituted 2(1H)-pyridones and consequent production of isoquinolones. Performing the same reactions with 5-nitro-2(1H)-pyridones yielded quinolones. DA reactions of 2(1H)-pyridones with nitro and methoxycarbonyl groups produced isoquinolones, quinolones and phenanthridones (the double DA adducts), aromatized or hydrogenated. The substituent effect was evaluated by calculating the activation energy, using the ab initio MO method.
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  • Ethenesulfonamide Derivatives, a Novel Class of Orally Active Endothelin-A Receptor Antagonists
    Hironori HARADA, Jun-ichi KAZAMI, Susumu WATANUKI, Ryuji TSUZUKI, Kats ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 606-612
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.606
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    In the present article we wish to report the discovery of a novel class of ETA-selective endothelin (ET) receptor antagonists through the modification of the ETA/ETB non-selective antagonist, Ro47-0203 (Bosentan, 1). Replacement of the benzenesulfonamide group of 1 with a 2-phenylethenesulfonamide group gave compound 5a and resulted in improvement in ETA-selectivity. Optimization of the alkoxy side chain attached to the core pyrimidine ring yielded the 2-fluoroethoxy derivative (5n) with further improvement of ETA-selectivity. [IC50=2.1 nM for ETA receptor, ETB/ETA ratio=1200]. After oral administration, compound 5n inhibited the big ET-1 induced pressor response in pithed rats with a DR2 value of 2.6 mg/kg and also exhibited a potent antagonistic activity in conscious rats.
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  • Co2(CO)8-mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives
    Chisato MUKAI, Sumie YAMAGUCHI, In Jong KIM, Miyoji HANAOKA
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 613-618
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.613
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    Successive treatment of 4, 5-epoxy-5-methyl-7-trimethylsilyl-6-heptyne-1-ol with Co2(CO)8 at 0 °C and a catalytic amount of BF3·OEt2 at −78 °C gave the tetrahydropyran derivatives with the cobalt-complexed moiety. Similarly 4, 5-epoxy-4-methyl-7-trimethylsilyl-6-heptyne-1-ol underwent ring closure under the above conditions to provide the corresponding tetrahydropyran derivatives. The preferential endo mode cyclization over the exo one was observed in these experiments.
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Notes
  • A Prenyloxycoumarin from Psiadia dentata1)
    Hélène FORTIN, Sophie TOMASI, Philippe JACCARD, Val&eacu ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 619-621
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.619
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    A new coumarin identified as 5-hydroxy-6-methoxy-7-(3-methyl-but-2-enyloxy)-2H-1-benzopyran-2-one (isoobtusitin) was isolated from Psiadia dentata. This compound showed, in vitro, a moderate inhibitory activity against poliovirus and a very weak activity against (HIV), whereas it was inactive against (HSV1), (VSV), and murine tumoral cell lines (3LL, L1210).
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  • Resazurin as an Electron Acceptor in Glucose Oxidase-Catalyzed Oxidation of Glucose
    Hatsuo MAEDA, Shinya MATSU-URA, Yuji YAMAUCHI, Hidenobu OHMORI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 622-625
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.622
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    The behavior of resazurin (1) as an electron acceptor in glucose oxidase (GOD)-catalyzed oxidation of glucose under anaerobic conditions is described. When a mixture of 1, glucose, and GOD in phosphate buffer (pH 7.4, 0.1 M) was incubated at 25 °C, the resulting solution turned purple to fluorescent pink due to the deoxygenated product, resorufin (2). On incubation of 1 with GOD alone or with H2O2 under essentially the same conditions, no color change was seen, indicating that generation of 2 in the enzymatic reaction is brought about through reduction of 1 by the reduced form (GODred) of GOD, which was also supported by the voltammetric behavior of 1. However, it was found that the enzymatic transformation of 1 to 2 is of no practical use as an indicator reaction for glucose determination using only GOD due to a slow reaction of 1 with GODred. Based on a pingpong type mechanism with a steady-state approximation, KM and kcat for 1 as an electron acceptor from GODred were estimated to be 15±1.3 μM and (5.0±0.5)×10-2s-1, respectively.
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  • Three New Triterpene Saponins from the Seeds of Aesculus chinensis
    Jing ZHAO, Xiu-Wei YANG, Masao HATTORI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 626-628
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.626
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    Three new triterpenoid saponins were isolated from the seeds of Aesculus chinensis, and characterized as 22-tigloylprotoaescigenin 3-O-[β-D-glucopyranosyl (1→2)] [β-D-glucopyranosyl (1→4)]-β-D-glucopyranosiduronic acid (escin IVg, 1), 22-angeloylprotoaescigenin 3-O-[β-D-glucopyranosyl (1→2)] [β-D-glucopyranosyl (1→4)]-β-D-glucopyranosiduronic acid (escin IVh, 2) and 16-angeloyl-21-acetylprotoaescigenin 3-O-[β-D-glucopyranosyl (1→2)] [β-D-glucopyranosyl (1→4)]-β-D-glucopyranosiduronic acid (escin VIb, 3), together with two known compounds, escin IIIa (4) and desacylescin I (5). Their structures were established on the basis of spectroscopic and chemical evidence.
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  • Amino Acid Derivatives with Anticonvulsant Activity
    Ryszard PARUSZEWSKI, Marzanna STRUPINSKA, James P. STABLES, Mariusz &S ...
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 629-631
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.629
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    A series of benzylamides of N-alkylated, N-acylated or free nine cyclic and one linear amino acids as potential anticonvulsants have been synthesized. The structures of the obtained compounds were designed on the basis of the previously determined structure and physicochemical properties/anticvonvulsant activity relationship of the formerly synthesized compounds of this type. The obtained compounds were evaluated in mice after intraperitoneal (ip) administration, by maximal electroshock seizure test (MES test), subcutaneous (sc) pentylenetetrazol test (sc PTZ test) and by the rotarod neurotoxicity test (Tox test). The results were the basis for their classification into one of three classes of the Anticonvulsant Screening Project (ASP) of the Antiepileptic Drug Development Program (ADDP) of the NIH. Three selected compounds were tested quantitatively in rats after oral administration. The MES ED50, sc PTZ ED50, Tox TD50 were determined and their protective index (PI) values were calculated. Anticonvulsant activity of the most promising compound (15) was examined in different seizure models. The respective ED50 and PI values of this compound were as follows: against bicuculline, 73 and 1.4; against PTZ, 47 and 2.2; against strychnine, 73 and 1.4; against pilocarpine 156, and 0.7; against kainic acid (2-carboxy-4-isopropenyl-3-pyrrolidineacetic acid), 39 and 2.6; against AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid), 10 and 10.3 and against NMDA (N-methyl-D-Aspartic acid), 114 and 0.9.
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  • Four New Oleanane Saponins from Anemone anhuiensis
    Wen-Cai YE, Qing-Wen ZHANG, Shou-Xun ZHAO, Chun-Tao CHE
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 632-634
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.632
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    Four new oleanane triterpene saponins, anhuienosides C-F, together with three known saponins, were isolated from the rhizomes of Anemone anhuiensis (Ranunculaceae). The structures of anhuienosides C-F were elucidated as 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-β-D-xylopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively.
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  • Studies on the Constituents of Clematis Species. VIII.1) Triterpenoid Saponins from the Aerial Part of Clematis tibetana Kuntz2)
    Yukio KAWATA, Haruhisa KIZU, Yukinori MIYAICHI, Tsuyoshi TOMIMORI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 635-638
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.635
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    From the aerial part of Clematis tibetana, two new hederagenin 3, 28-O-bisdesmosides called clematibetosides A and C, and a new gypsogenin 3, 28-O-bisdesmoside called clematibetoside B, have been isolated together with ten known saponins. The structures of the new saponins have been elucidated based on chemical and spectral evidence as follows: clematibetoside A, 3-O-(2-O-caffeoyl)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside; clematibetoside B, 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl gypsogenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside; clematibetoside C, 3-O-β-D-ribopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside.
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  • Synthesis of Styrenes through the Biocatalytic Decarboxylation of trans-Cinnamic Acids by Plant Cell Cultures
    Masumi TAKEMOTO, Kazuo ACHIWA
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 639-641
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.639
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    A novel method for producing styrenes from trans-cinnamic acids was developed. When trans-cinnamic acid was incubated with plant cell cultures at room temperature, styrene was obtained. 4-Hydroxy-3-methoxystyrene (2a), 3-nitrostyrene (2f) and furan (2g) were synthesized quantitatively.
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  • Radical Scavenging Activity against 1, 1-Diphenyl-2-picrylhydrazyl of Ascorbic Acid 2-Glucoside (AA-2G) and 6-Acyl-AA-2G
    Yoshihito FUJINAMI, Akihiro TAI, Itaru YAMAMOTO
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 642-644
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.642
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    The radical scavenging activity of the stable derivatives, which are O-substituted at the C-2 position of ascorbic acid (AA), against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) was evaluated in buffer under diffrent pH conditions, and compared with those of AA and α-tocopherol. AA was shown to have 50% radical scavenging ability (EC50) at a concentration of 2.2×10-5 M against 0.1 mM DPPH in 60% ethanol. Ascorbyl 6-palmitate, a lipophilic AA derivative which has a free endiol group and is therefore unstable, also showed potent radical scavenging activity with EC50 of 2.9×10-5 M. A typical lipophilic antioxidant, α-tocopherol gave a similar EC50 value as that of AA. In contrast, ascorbyl 2, 6-dipalmitate, AA 2-phosphate and AA 2-sulfate exhibited negligible scavenging activity. On the other hand, 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G) and a series of 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) themselves exhibited the radical scavenging activity of EC50: 6.1×10-5 M and 4.4×10-5-5.9×10-5 M, respectively, although their activities were lower than that of AA. Among 6-Acyl-AA-2G derivatives, the EC50 values tended to decrease with increasing length of their acyl carbon group. Increasing pH of the buffer resulted in decrease in the scavenging activity of all compounds tested as expected. We speculate that the difference in the radical scavenging activity of derivatives O-substituted at the C-2 position of AA may be ascribed to the linkage type of the substituent group to the endiol-lactone resonance system and the degree of dissociation of the C-3 proton.
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  • Structures of New Sesquiterpenoids from Farfarae Flos1)
    Yasunori YAOITA, Noriko SUZUKI, Masao KIKUCHI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 645-648
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.645
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    Two new bisabolane-type sesquiterpenoids, (3R, 4R, 6S)-3, 4-epoxybisabola-7(14), 10-dien-2-one and (1R, 3R, 4R, 5S, 6S)-1-acetoxy-8-angeloyloxy-3, 4-epoxy-5-hydroxybisabola-7(14), 10-dien-2-one, and a new oplopane-type sesquiterpenoid, 14(R)-hydroxy-7β-isovaleroyloxyoplop-8(10)-en-2-one, were isolated from Farfarae Flos along with three known compounds. The structures of these compounds were elucidated on the basis of spectroscopic evidence.
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  • Limonoids from Citrus sudachi
    Hiroyuki NAKAGAWA, Hongquan DUAN, Yoshihisa TAKAISHI
    Article type: scientific monograph
    2001 Volume 49 Issue 5 Pages 649-651
    Published: 2001
    Released on J-STAGE: April 26, 2002
    DOIhttps://doi.org/10.1248/cpb.49.649
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    Four new limonoid derivatives, 1-O-methylichangensin (1), sudachinoid A (2), B (3), and C (4) were isolated from the seeds of Citrus sudachi, together with the known compounds ichangensin, obacunone, obacunoic acid and limonin, and the structures of the new compounds were elucidated based on spectroscopic and chemical evidence.
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