Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 45, Issue 6
Displaying 1-23 of 23 articles from this issue
  • Hideo KANEKO, Naokazu MURAHASHI, Atsushi SASAKI, Harutami YAMADA, Masa ...
    1997 Volume 45 Issue 6 Pages 951-956
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    With the intention of obtaining a novel liposome as a drug carrier able to avoid clearance by the reticuloendothelial system (RES), the authors synthesized two sialoglycolipids, i.e., 2-O-(8-hexadecanoylamino-3, 6-dioxaoctyl)-β-N-acetylneuraminic acid sodium salt (Sia-t-pa) and 2-O-[8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl]-β-N-acetylneuraminic acid sodium salt (Sia-t-psa) and modified the surface of their liposomal membrane.Sia-t-pa was found to be eluted from the liposomal membrane by serum albumin, whereas Sia-t-psa was not, using the gel filtration method. In order to clarify the reason why there was such a difference between Sia-t-pa and Sia-t-psa, we investigated the properties of the phospholipid bilayer-incorporated sialoglycolipids physicochemically.The effect of the anchor structure of the sialoglycolipids, i.e., single acyl chain (Sia-t-pa) or double acyl chain (Sia-t-psa), on the fluidity and calorimetric properties was noticeably different. It was inferred that the effect was attributable to a difference in the position of the sialoglycolipid incorporated in the bilayer membrane.
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  • Ruben Alfredo TOSCANO, Maria del Carmen HERNANDEZ-GALINDO, Raul ROSAS, ...
    1997 Volume 45 Issue 6 Pages 957-961
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    The reaction products of 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (TPT) with secondary amines have been thoroughly examined by spectroscopic and X-ray diffraction methods. The products include the normal ones expected for a ring-opening reaction (1-azahexatriene and cyanine) in addition to the "unexpected"formation of a 4-substituted 1, 4-dihydropyridine. Tandem reactions -ring-opening, nucleophilic addition- on the pyridinium ring seems to be the most probable pathway to the 1, 4-dihydropyridine compounds. Preliminary tests on the compounds revealed significant anti-microbial activity against Gram-positive bacteria, with moderate specificity towards Enterococcus faecalis.
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  • Mikiko MAEDA, Fumiaki OKAZAKI, Mayumi MURAYAMA, Yohko TACHIBANA, Yutak ...
    1997 Volume 45 Issue 6 Pages 962-965
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    A short synthetic route to (-)-bulgecinine (1), the amino acid moiety of bulgecins, was established by using 1, 3-dipolar cycloaddition of N-benzyl-α-methoxycarbonylmethanimine N-oxide (6) to a chiral allylic alcohol (5) with moderate threo selectivity as the key reaction.
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  • Akito NAGATSU, Yuichiro TABUNOKI, Shin-ichi NAGAI, Taisei UEDA, Jinsak ...
    1997 Volume 45 Issue 6 Pages 966-970
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    7-Carboxymethylmonensin (3), 7-aminomonensin (4), and 7-oxomonensin (5) were synthesized via protected 7-oxomonensin (2), which is expected to be a useful intermediate for the preparation of various monensin derivatives.Compounds 3-5 exhibited smaller ion transport activity than monensin (1).
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  • Yoshisuke TSUDA, Shinsuke NOGUCHI, Kimihiro KANEMITSU, Yoshiyuki SATO, ...
    1997 Volume 45 Issue 6 Pages 971-980
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Pyranoside 3, 4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3, 4-thiolcarbonates of cis-stereochemistry, in accepTable yields.2, 3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides(peracetate forms) by conventional means.
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  • Eiichi KOTANI, Tetsuta TAKEYA, Motohide YOSHIIKE, Atsuko WATANABE, Sei ...
    1997 Volume 45 Issue 6 Pages 981-986
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Non-enzymic oxygenation reaction of methyl valproate (2) utilizing a simple model system for mono-oxygenases, Fe(MeCN)2+6-H2O2-Ac2O in MeCN, was investigated in connection with stereochemical analyses of the mammalian metabolites of 1. This oxygenation reaction of methyl valproate (2) gave a 92 : 8 mixture of the anti-isomer 4a and the syn-isomer 4b, together with 5a, and 5b corresponding to the mammalian metabolites of 1. The stereochemistry of 4a, 5a, and 5b was elucidated by spectral analyses of the corresponding β-lactone 6a, γ-lectone 7a and 7b prepared from the oxygenation products. The asymmetric synthesis of (+)-7a was also achieved.
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  • Kiyoshi TSUJI, Katsuya NAKAMURA, Nobukiyo KONISHI, Takashi TOJO, Takeh ...
    1997 Volume 45 Issue 6 Pages 987-995
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    A series of novel 1, 5-diarylpyrazole derivatives was synthesized and tested for anti-inflammatory and analgesic activities to develop anti-inflammatory agents with fewer side effects than existing nonsteroidal anti-inflammatory drugs. The structure-activity relationships in this series were extensively studied. Electron-withdrawing substituents such as NC and CF3 were optimal at the 3-position of the pyrazole ring. Replacement of these substituents with bulky ones gave less active compounds. The 4-(methylsulfonyl)phenyl group seemed to be the optimal group at the 5-position of the pyrazole ring. The most potent compound was 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-pyrazole-3-carbonitrile (19a), with oral ED50 values of 0.030 and 0.47mg/kg on adjuvant-induced arthritis and collagen-induced arthritis, respectively, and an ED30 value of 7.4mg/kg in the yeast-induced hyperalgesia (Randall-Selitto) assay. Compound 19a also showed potent inducible cyclooxygenase (COX-2)-inhibitory activity (IC50=0.24μM) with no COX-1 inhibition even at 100μM.
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  • Toshihiro WATANABE, Isao KINOYAMA, Akio KAKEFUDA, Toshio OKAZAKI, Kenj ...
    1997 Volume 45 Issue 6 Pages 996-1007
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    A series of 5, 11-dihydro-6H-pyrido[2, 3-b][1, 4]benzodiazepin-6-one derivatives containing the succinamide skeleton has been synthesized and evaluated for M1, M2 and M3 muscarinic receptor binding affinities (in vitro) and M2 and M3 muscarinic receptor antagonistic activities (in vivo). Some of them showed higher and more selective binding affinities for M2 muscarinic receptors than that of AFDX 116. Among them, 11-[3-[N-[2-(N-benzyl-N-methylamino)ethyl]-N-ethylcarbamoyl]propiony]-5, 11-dihydro-6H-pyrido[2, 3-b][1, 4]benzodiazepin-6-one (68) was found to be the most potent and selective M2 muscarinic receptor antagonist in vitro. This compound also strongly inhibited the oxotremorine-induced bradycardia after intravenous administration and showed 130-fold selectivity for M2 muscarinic receptors over M3 muscarinic receptors in vivo.
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  • Hirozumi INOUE, Mikihiko KONDA, Tomiki HASHIYAMA, Hisao OTSUKA, AKishi ...
    1997 Volume 45 Issue 6 Pages 1008-1026
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    2, 3-Dihydro-1, 5-benzothiazepin-4(5H)-ones substituted with an alkyl, alkoxy, alkylthio, hydroxy, or amino group on the fused benzene ring of the 1, 5-benzothiazepine skeleton were synthesized and their vasodilating, antihypertensive, and platelet aggregation-inhibitory activities were investigated. (-)-cis-3-Acetoxy-5-[2-(dimethylamino)ethyl]-2, 3-dihydro-8-methyl-2-(4-methylphenyl)-1, 5-benzothiazepin-4(5H)-one ((-)-13e) was selected for further studies as a potent inhibitor of platelet aggregation.
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  • Hideo TERAUCHI, Akihiko TANITAME, Keiko TADA, Keiji NAKAMURA, Yasuhiro ...
    1997 Volume 45 Issue 6 Pages 1027-1038
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    Members of a new series of 2-[(2, 4-dimethoxybenzyl)sulfinyl]-N-(4-pyridinyl)pyridine-3-carboxamides were synthesized and evaluated for their gastric antisecretory activity and the ability to inhibit cytochrome P450-dependent O-dealkylation of 7-ethoxycoumarin (7-EC) in rat liver microsomes. Several of the compounds synthesized exhibited potent inhibitory activities against both [14C]aminopyrine accumulation stimulated by dibutyryl cyclic AMP in isolated rabbit parietal cells and histamine-induced gastric acid secretion in pylorus-ligated rats when administered intraduodenally; their inhibitory activities were equivalent to or superior to those of the parent compound [2-[(2, 4-dimethoxybenzyl)sulfinyl]-N-(4-pyridinyl)pyridine-3-carboxamide] and omeprazole. Among the compounds having potent antisecretory activity in vitro and in vivo, 2-[(2, 4-dimethoxybenzyl)sulfinyl]-N-(2, 5-dimethyl-4-pyridinyl)pyridine-3-carboxamide and 2-[(2, 4-dimethoxybenzyl)sulfinyl]-N-(2, 6-dimethyl-4-pyridinyl)pyridine-3-carboxamide in particular showed lower inhibitory activity against the 7-EC deethylase than omeprazole. It seems probable that, unlike omeprazole, these compounds do not interact with a metabolism of other drugs in vivo. These compounds, therefore, are considered to be more promising candidate agents for treating acid-releated gastrointestinal disorders than the parent compound reported previously.
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  • Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Takahiro UENO, Kenichi YASHIRO ...
    1997 Volume 45 Issue 6 Pages 1039-1045
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    The glycosidic fraction from the dried roots of Panax notoginseng (BURK.) F. H. CHEN was found to show protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid β-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C, and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb1 using photosensitized oxygenation, as follows : notoginsenoside A; 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] 3β, 12β, 20(S), 25-tetrahydroxy-dammar-23-ene, B; 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] 3β, 12β, 20(S)-trihydroxy-25-en-24-one, C; 3-O-[β-D-xylopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] 3β, 12β, 20(S)-trihydroxydammar-24ξ-hydroperoxydammar-25-ene, and D; 3-O-[β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl]-20-O-[β-D-xylopyranosyl (1→6)-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl] 20(S)-protopanaxadiol, respectively.
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  • Tsutomu KANAZAWA, Yuki OHKAWA, TAKASHI KUDA, Yasushi MINOBE, Tadato TA ...
    1997 Volume 45 Issue 6 Pages 1046-1051
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    New γ-pyrones, 9'-oxopodopyrone (3) and 8-methyl-9'-oxopodopyrone (4) were isolated from the leaves of Gonystylus keithii, along with known γ-pyrones, 10'-oxopodopyrone (1) and 8-methyl-10'-oxopodopyrone (2). These γ-pyrones markedly inhibited the bovine parathyroid hormone (PTH)-induced Ca release from neonatal mouse calvaria in vitro. It is the first time that γ-pyrones showed inhibitory effects on bone resorption, and these compounds may be seed compounds of new drugs for osteoporosis.
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  • Masayuki YOSHIKAWA, Yue DAI, Hiromi SHIMADA, Toshio MORIKAWA, Narumi M ...
    1997 Volume 45 Issue 6 Pages 1052-1055
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Four new saponins called kochianosides I, II, III, and IV were isolated from the glycosidic fraction of the fruit of Chinese Kochia scoparia, which has exhibited an antipruritogenic effect, together with eight known saponins. The structures of kochianosides I, II, III, and IV were characterized on the basis of physicochemical evidence as 22α-hydroxyoleanolic acid 3-O-β-D-glucopyranosiduronic acid, morolic acid 3-O-[β-D-glucopyrabnosyl(1→2)][β-D-xylopyranosyl(1→3) -β-D-glucopyranosiduronic acid, 3β, 12α-dihydroxyolean-28, 13β-olide 3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosiduronic acid, and betulinic acid 3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosiduronic acid, respectively.
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  • Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Takahiro UENO, Nobuko HIROKAWA ...
    1997 Volume 45 Issue 6 Pages 1056-1062
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
    JOURNAL FREE ACCESS
    Following the characterization of notoginsenosides-A, -B, -C, and -D, new dammarane-type triterpene oligoglycosides, notoginsenosides-E, -G, -H, -I, and -J, and a novel acetylenic fatty acid glycoside, notoginsenic acid β-sophoroside, were isolated from the glycoside fraction with hepatoprotecting activity obtained from the dried roots of Panax notoginseng (BURK.) F. H. CHEN. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : notoginsenoside E; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 12β, 20(S)-trihydroxy-25-hydroperoxydammar-23-ene, G; 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 7β, 20(S)-trihydroxydammar-5, 24-diene, H; 6-O-[β-D-xylopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 25-pentahydroxydammar-23-ene, I; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl]-3β, 20(S)-dihydroxydammar-24-ene, J; 6-O-(β-D-glucopyranosyl)-20-O-(β-D-glucopyranosyl)-3β, 6α, 12β, 20(S), 24ζ, 25-hexahydroxydammarane, and notoginsenic acid β-sophoroside; 10-hydroxydaca-4, 6-diynoic acid 10-O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside, respectively.
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  • Kaoru KANEKO, Ken KANADA, Tatsuhiko YAMADA, Masaharu MIYAGI, Noriyasu ...
    1997 Volume 45 Issue 6 Pages 1063-1068
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Masking of the bitter taste from tablets by a water-insoluble gel formed by sodium alginate and bivalent metal was studied. Amiprilose hydrochloride was selected as the model drug with a bitter taste, and its core tablet was prepared. The core tablet was under-coated with sodium alginate and over-coated with calcium gluconate as a bivalent metal, or it was under-coated with calcium gluconate and over-coated with sodium alginate in order to form a gel on the surface of the tablet in the mouth at oral administration. The taste masking was evaluated by the amount of amiprilose hydrochloride released from the tablet. In addition, cross sections of the tablets subjected to a dissolution test were observed by scanning electron microscopy and energy dispersive X-ray microanalysis to evaluate the component distribution of the coated layers and behavior of the durg.Water-insoluble gel on the surface of the tablet was minimally formed by under-coating with sodium alginate and over-coating with calcium gluconate, and its masking time was 1min. On the other hand, water-insoluble gel was formed by under-coating with calcium gluconate and over-coating with sodium alginate, and its masking time was relatively long. These results suggest that the gel formation on the surface of tablets by under-coating with calcium gluconate and over-coating with sodium alginate is useful or taste masking of tablets in the mouth at the time of oral administration.
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  • Hiroyasu KOKUBO, Hisakazu SUNADA
    1997 Volume 45 Issue 6 Pages 1069-1072
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    A lactose-cornstarch model system with hydroxypropyl methylcellulose 2910 (HPMC 3cP) as a binder was used to evaluate the effects of several process variables (moisture level, spray feed rate and drying air flow rate) on the particle size distribution of granules prepared in a fluidized bed using a dry mixing method of binder addition. Moisture levels were controlled via an infrared moisture sensor. The distribtuion of binder in different sized fractions of granules was also determined by measuring the contents of the methoxyl group. Moisture level was the most important factor for granule growth, and higher moisture levels increased the granule size. The time for which a given moisture level was maintained and the fluidizing air flow rate had little effect on granule size, size distribution, binder distribution or apparent density. This implies that mixing is efficient during fluidized bed granulation by the dry mixing method and that binder behavior is mainly determined by the moisture level of the wet mass. It was concluded that if a fixed moisture level is maintained during fluidized bed granulation with the dry mixing method of binder addition, variation of the other operational conditions should have little effect on the consistency of the product.
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  • Iwao SUZUKI, Maki ITO, Tetsuo OSA
    1997 Volume 45 Issue 6 Pages 1073-1079
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    The β-cyclodextrin derivative (DN-β-CyD) having a branched arm derived from L-ornitine and two molecules of 2-naphthoic acid was synthesized for exploring the conformational change associated with guest binding. When DN-β-CyD was alone in a 10% ethylene glycol aqueous solution, one of the naphthoyl residues in the branched arm was accommodated in the DN-β-CyD cavity. This intramolecular self complex was stabilized by the other naphthoyl moiety located ouside of the cavity on the basis of a hydrophobic capping effect. Upon guest binding, the naphthoyl residue residing in the cavity was expelled from the cavity, forming an excimer with the other naphthoyl residue outside of the cavity. DN-β-CyD was not able to bind the guests strongly, owing to the stability of the intramolecular complexation form. Although DN-β-CyD was proven to be a poor host in guest binding, the guest recognition ability of DN-β-CyD could be estimated by the use of guest-induced fluorescence variations. DN-β-CyD could bind both monoterpenes and cholic acid derivatives to nearly the same extent. However, variations in fluorescence intensity induced by guest binding indicated, as a fluproscent sensing system, that DN-β-CyD was able to detect cholic acid derivatives with higher sensitivity than terpenoids.
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  • Thomas ROSENAU, Wolf Dieter HABICHER
    1997 Volume 45 Issue 6 Pages 1080-1084
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Reaction of 5a-bromo-α-tocopherol with ascorbic acid produces 5a-tocopheryl ascorbate which is designated "vitamin CE." This novel tocopherol derivative represents an interesting prodrug form of α-tocopherol (vitamin E) that is stable under acidic conditions, but regenerates finely dispersed vitamin E in basic media. The reaction mechanism of the base-induced decomposition of vitamin CE involves elimination of ascorbate and production of an ortho-quinone methide intermediate that oxidizes ascorbate, and is reduced to vitamin E. Kinetic experiments showed the reaction to proceed in the pH range of 8 to 11 under physiological conditions. Tissue culture measurements demonstrated that vitamin E generated from the novel derivative is absorbed at much higher rates than conventional preparations and can even be absorbed under simulated conditions of malabsorption where there is no uptake of conventional vitamin E medications.
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  • Yoshio TAKEUCHI, Akira SATOH, Takanori SUZUKI, Ayako KAMEDA, Masahiro ...
    1997 Volume 45 Issue 6 Pages 1085-1088
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    In order to develop novel methods for electrophilic and enantioselective fluorination of active methine compounds, preliminary experiments were carried out. The N-tosyl derivative 5 obtained from D-phenylglycine was fluorinated with FClO3 or diluted F2 gas to give the N-fluoro-N-tosyl derivative 6. N-Tosyl- or N-mesyl-(S)-α-phenethylamine 7 or 8 was sujected to FClO3 fluorination to produce the corresponding N-fluoro derivative, 10 or 11, respectively.Enantioselective flurination of some methine compounds was attempted employing the above N-fluoro agents. Best result was obtained when 2-benzyl-1-tetralone/KHMDS was treated with 10 to produce the fluorinated tetralone 17 in 53% yield with enantiomeric excess (ee) of 48%.
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  • Keisuke MIYAJIMA, Noriaki GOMI, Kiyoshi IKEDA, Kazuo ACHIWA
    1997 Volume 45 Issue 6 Pages 1089-1093
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Four novel N-acylated L-serine or L-threonine-containing non-phosphorylated D-glucosamine derivatives structurally corresponding to the lipid A disaccharide backbone were synthesized. Compounds 2, 3 and 4 exhibited potent mitogenic activity. Among the threonine-linked lipid A analogs (1-3), serine-lipid A analogs (4-6) and homoserine-linked lipid A analogs (7-9), the serine compounds (4, 6) showed the most potent mitogenic activity.
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  • Masateru ONO, Yasyuki ITO, Satoko KUBO, Toshihiro NOHARA
    1997 Volume 45 Issue 6 Pages 1094-1096
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Two new iridoids, called viteoids I and II, were isolated from Viticis trifoliae Fructus (fruit of Vitex rotundifolia L. fil.) along with six known iridoids, eucommiol, iridolactone, pedicularis-lactone, agnuside, VR-I and 1-oxo-eucommiol. The chemical structures of viteoids I and II were determined on the bases of spectroscopic data.
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  • Akiko OHNO, Haruhisa KIZU, Tsuyoshi TOMIMORI
    1997 Volume 45 Issue 6 Pages 1097-1100
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    From the aerial parts of Scutellaria grossa, a new neoclerodane diterpene named scutegrossin A has been isolated together with five known neoclerodane diterpenes, jodrellin B, scutecolumnin A, scutalsin, scutecyprol B and scutalbin B.The strucure of a new compound has been determined by spectroscopic and chemical methods as (11S, 13S, 16S, 19R)-6α-O-acetyl-19-O-[(E)-2-methyl-2-butenoyl]-2α, 19;4α, 18;11, 16;15, 16-tetraepoxy-14-neoclerodene-6, 19-diol.In addition, the absolute stereochemistry of 2-methylbutanoyl group of scutecolumnin A and scutalbin B has been ascertained to be the S form.
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  • Hiroyuki FUCHINO, Hisanori NAKAMURA, Hiroshi WADA, Takashi HAKAMATSUKA ...
    1997 Volume 45 Issue 6 Pages 1101-1102
    Published: June 15, 1997
    Released on J-STAGE: March 31, 2008
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    Two new acyl-phloroglucinols, called atrata-phloroglucinols A and B, were isolated from the fronds of Dryopteris atrata. Their structures were elucidated by two dimensional NMR spectral data to be flavaspidic acids AA and AB of which the methyl group at C-5' is replaced with 8-aristol-9-enyl group.
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