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Volume 39, Issue 9
Displaying 1-50 of 59 articles from this issue
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Saburo SHIMABAYASHI, Yoshio TANIZAWA, Katsuhiro ISHIDA1991 Volume 39 Issue 9 Pages 2183-2188
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe amount of adsorption of bovine serum albumin (BSA) by hydroxyapatite (HAP) increased with a concentration of CaCl2 due to the bridging effect of Ca2+ between adsorbate BSA and adsorbent HAP. On the other hand, it decreased remarkably with a concentration of K2HPO4. This was explained in terms of the effects of ionic strength and competitive adsorption between inorganic phosphate anion (Pi) and BSA, because BSA is in negatively charged over the examined pHs. A similar effect was observed in the presence of phosphorylated compounds such as phosphoserine, phytate, and phosphorylated polyvinylalcohol. The inhibiting effect of these compounds was stronger than that of their mother compounds (serine, inositol, and polyvinylalcohol). This result shows that phosphate groups bound to the mother compounds interfere with the adsorption of BSA by HAP in the same manner that Pi does. Although the adsorption of BSA was almost irreversible with respect to dilution with water, desorption was performed when these organic phosphorylated compounds were added after the accomplishment of the adsorption of BSA. However, the effective concentration of the phosphorylated compounds for the desorption of BSA was fairly higher than that for the competitive inhibition against the BSA adsorption.View full abstractDownload PDF (918K) -
Yasuoki MURAKAMI, Yuusaku YOKOYAMA, Chiyoko AOKI(nee ISHIYAMA), Hideha ...1991 Volume 39 Issue 9 Pages 2189-2195
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCrenatine (1a), which is a member of a new class of β-carboline alkaloids having an oxygen functionality at the 4-position, was synthesized starting from ethyl 1-benzylindole-2-carboxylate (12a) via cyclization of an elaborated C2-subsitituent to the 3-position of the indole nucleus and aluminum chloride-catalyzed debenzylation of the protected indolic nitrogen. 1-Ethyl-4-hydroxy-9-methyl-β-carboline (26b), a positional isomer of crenatine with regard to the methyl group, was also synthesized through the same methodology.View full abstractDownload PDF (1132K) -
Yueh-Hsiung KUO, Lien-Huei CHEN, Li-Ming WANG1991 Volume 39 Issue 9 Pages 2196-2200
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSensitized photooxygenation of isoeugenol gave seven products in methanol, seven products in ethanol, six products in acetone, and five products in acetonitrile. One of the products is a 7, 7'-linked lignan of a type which has not yet been observed in nature. The structures of these products were elucidated and the mechanisms of their formation are discussed.View full abstractDownload PDF (788K) -
Nobuo IKOTA, Osamu YOSHINO, Kenji KOGA1991 Volume 39 Issue 9 Pages 2201-2206
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.View full abstractDownload PDF (1002K) -
Toshio SHIDA, Kohji YOKOYAMA, Satoshi TAMAI, Junichi SEKIGUCHI1991 Volume 39 Issue 9 Pages 2207-2211
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOligonucleotides containing a dG cluster, d(TmGnTm), are models of single-stranded parts of telomeric deoxyribonucleic acid and substitutes for poly(dG). Electrophoretic and spectroscopic analyses of the oligomers indicate that the oligomers can form two alternative structures, single- and quadruple-stranded helices, in solution at room temperature. The transformation of the single-stranded form into the quadruple-stranded form or vice versa is undetectable in 0.1 M NaCl at 4.3×10-5 M strand concentration at room temperature. However, at a 50-fold higher strand concentration, the single-stranded oligomer is gradually converted into the quadruplex. An increase in ionic strength stabilizes the single-stranded structure, so it seems to inhibit the formation of the quadruplex. The quadruplex, [d(TTGGGGTT)]4, is resistant to denaturation in 7 M urea, in which the Watson-Crick type d(TTGGGGTT)·d(AACCCCAA) duplex dissociates. An increase in the number of T residues facilitates the dissociation of the quadruplex by heating. Thus the number of T residues surrounding the dG cluster might control the rigidity of the quadruplex structure.View full abstractDownload PDF (1093K) -
Toshiyuki KONOSU, Sadao OIDA1991 Volume 39 Issue 9 Pages 2212-2215
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antifungal β-lactam (2R, 5S)-2-(hydroxymethyl)clavam was synthesized in a convergent and stereocontrolled manner from methyl 6-phthalimidopenicillanate and 2, 3-O-isopropylidene-(R)-glyceraldehyde. Convenient methods of acetonide cleavage and phthalimide deblocking are also described.View full abstractDownload PDF (734K) -
Takeaki NAITO, Etsuko KURODA(nee DOI), Okiko MIYATA, Ichiya NINOMIYA1991 Volume 39 Issue 9 Pages 2216-2218
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal synthesis of naucleficine (3a) was accomplished for the first time via an alkaloid, oxogambirtannine (3b), which was efficiently prepared by photocyclization of the o-methoxy-enamide 2b. The method is a practical one, suitable for large-scale preparation.View full abstractDownload PDF (566K) -
Yasushi ARAKAWA, Shigeyuki YOSHIFUJI1991 Volume 39 Issue 9 Pages 2219-2224
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNatural (2S, 3S, 4S)-3, 4-dihydroxyproline (1) and the new (2R, 3S, 4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.View full abstractDownload PDF (876K) -
Yasuyuki KITA, Norio SHIBATA, Osamu TAMURA, Takashi MIKI1991 Volume 39 Issue 9 Pages 2225-2232
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Amido sulfoxides (1) reacted with O-silylated ketene acetal (16) in dry acetonitrile in the presence of a catalytic amount of zinc iodide to give the 4-phenylthioazetidin-2-ones (17). Oxidation of 17 with m-chloroperbenzoic acid gave the corresponding sulfoxides (18), which were treated with 16 to give the azetidin-2-one esters (20), known precursors of PS-5-type carbapenem antibiotics.View full abstractDownload PDF (1329K) -
Takashi YOSHIDA, Hideyuki OHBAYASHI, Kohkichi ISHIHARA, Wakayo OHWASHI ...1991 Volume 39 Issue 9 Pages 2233-2240
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new hydrolyzable tannins, methylvescalagin and nobotanins, A, D and F, along with eleven known polyphenolics, have been isolated from the leaves of Tibouchina semidecandra COGN. Based on spectral and chemical evidence, nobotanin D was characterized as 1, 6-di-O-galloyl-2, 3-O-(S)-hexahydroxydiphenoyl-β-D-glucose (16), and the structures of nobotanins A (17) and F (18) were established as dimeric hydrolyzable tannins possessing a valoneoyl group as a linking unit between the monomers.View full abstractDownload PDF (1113K) -
Toshiyuki KONOSU, Takeo MIYAOKA, Yawara TAJIMA, Sadao OIDA1991 Volume 39 Issue 9 Pages 2241-2246
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereocontrolled syntheses of an optically active triazolymethyloxirane 2, an important intermediate for the preparation of anifungal oxazolidine compounds 1, was achieved by two methods using L-lactic acid as a starting material. The key intermediate ketone 6 used in the procedures also served for the synthesis of the enantiomer of 2 and the corresponding diastereomeric epoxide.View full abstractDownload PDF (986K) -
Takashi YOSHIDA, Tong CHOU, Aya NITTA, Takuo OKUDA1991 Volume 39 Issue 9 Pages 2247-2251
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new hydrolyzable tannins, schimawalins A (10) and B (17), have been isolated from the dried flowers of Schima wallichii (DC) KORTH. (Theaceae), and their structures, having a dilactonized valoneoyl group in the molecule, were established based on spectral and chemical evidence. Eight known hydrolyzable tannins, including camelliin B (8), the main constitvent of the flower, with a macrocyclic dimer structure, were also isolated. The orientation of the valoneoyl groups in camelliin B was completely determined.View full abstractDownload PDF (702K) -
Motoharu JU-ICHI, Yuko TAKEMURA, Miki AZUMA, Kiyoko TANAKA, Masayoshi ...1991 Volume 39 Issue 9 Pages 2252-2255
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new coumarins named nordenletin (1), oxanordentatin (3), oxaclausarin (4), seselino (6), and seselinol isovalerate (8) were isolated from the roots of Citrus hassaku (Rutasceae) and their structures were elucidated on the basis of spectrometric analyses.View full abstractDownload PDF (638K) -
Yoshiyasu KITAHARA, Tatsuya NAKAI, Shinsuke NAKAHARA, Manabu AKAZAWA, ...1991 Volume 39 Issue 9 Pages 2256-2263
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5, 8-Isopuinolinediones (12, 18, 25), 7, 8-isoquinolinediones (14, 19) and 5, 6-isoquinolinediones (26) were synthesized by oxidative demethylation of the corresponding dimethoxyisoquinolines with cerium(IV) ammonium nitrate or silver(II) oxide. 8-Dialkylamino-5, 6-isoquinolinediones (31) and 3, 5-bis(dialkylamino)-7, 8-isoquinolinediones (33) were prepared by copper(II)-catalyzed oxidation of the corresponding isoquinolinols with secondary amines. 5, 8-Isoquinolinediones (29, 34, 40) were also prepared.View full abstractDownload PDF (1201K) -
Takashi YOSHIDA, Wakayo OHWASHI, Kumiko HABA, Hideyuki OHBAYASHI, Kohk ...1991 Volume 39 Issue 9 Pages 2264-2270
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of three new hydrolyzable tannin oligomers, nobotanins B (7), C (20) and E (21), which were isolated from the leaves of Tibouchina semidecandra COGN. (Melastomataceae), have been elucidated on the basis of spectral and chemical evidence. Nobotanin B is an isomer of a co-existing dimer, nobotanin F, and nobotanins C and E are trimers possessing the nobotanin B moiety as a partial structure.View full abstractDownload PDF (915K) -
Hongxiang LOU, Xian LI, Masayuki ONDA, Yaeko KONDA, Mieko URANO, Yoshi ...1991 Volume 39 Issue 9 Pages 2271-2276
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absolute stereochemistry of hancokinol, hancolupenone, hancolupenol, hancolupenol hexacosanoate, which are novel triterpenes, from Cynanchum hancokianum, has been elucidated by means of spectroscopic [nuclear magnetic resonance (NMR), circular dichroism (CD)] analyses.View full abstractDownload PDF (825K) -
Nobutoshi MURAKAMI, Takashi MORIMOTO, Hideaki IMAMURA, Taisei UEDA, Sh ...1991 Volume 39 Issue 9 Pages 2277-2281
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven new monogalactosyl diacylglycerols (1-7) and six new digalactosyl diacylglycerols (11-16) were isolated from an axenically cultured cyanobacterium, P. tenue. Their structures were elucidated on the basis of physicochemical evidence and the results of enzymatic hydrolysis using a lipase (from Rhizopus arrhizus). Comparison of antialgal activity for P. tenue between monogalactosyl diacylglycerols (1-8) and digalactosyl diacylglycerols (11-19) revealed that the former showed more potent activity than the latter.View full abstractDownload PDF (917K) -
Motomasa KOBAYASHI, Manabu HORI, Kumiko KAN, Tohru YASUZAWA, Matsutaro ...1991 Volume 39 Issue 9 Pages 2282-2287
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTriterpene-oligoglycoside constituents in ten sea cucumber species inhabiting Okinawan coral reefs were investigated. Several antifungal oligoglycosides were isolated from six species [stichlorosides A1 (15), A2 (16), B1 (17), B2 (18), C1 (19), and C2 (20) from Thelonota ananas (baika-namako in Japanese) and Stichopus hermanni; 15, 17, and 19 from Thelonota anax; bivittosides C (13) and D (14) from Bohadschia argus (janome-namako); holothurin A (6) from Holothuria edulis (akamishikiri); and 6 and echinoside A (10) from Bohadschia graeffei (kurote-namako)]. Furthermore, several oligoglycosides were isolated in their desulfated forms from four species [6 and 10 from Holothuria axiologa; holothurin B (4), 6, echinoside B (8), and 10 from Holothuria atra (kuro-namako); 6, 10, and 24-dehydroechinoside A (24) from Holothuria scabra (haneji-namako); and 8, 10, 24-dehydroechinoside B (22), and 24 from Actinopyga mauritiana (kuriiro-namako)]. 24-Dehydroechinoside B (22) is a new lanostane-type triterpene oligoglycoside.View full abstractDownload PDF (1041K) -
Kikuo ISHIZUMI, Atsuyuki KOJIMA, Fujio ANTOKU1991 Volume 39 Issue 9 Pages 2288-2300
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of cyclic imides bearing a ω-(4-aryl and 4-heteroaryl-1-piperazinyl)alkyl moieties was synthesized and tested in vivo for anxiolytic activity. The in vitro binding affinities of these compounds were also examined for 5-HT1A receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, (1R*, 2S*, 3R*, 4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2, 3-bicyclo[2.2.1]heptanedicarboximide (1 : tandospirone), was found to be equipotent with buspirone in its anxiolytic activity and more anxio-selective than buspirone and diazepam. Tandospirone (1) is currently undergoing clinical evaluation as a selective anxiolytic agent.View full abstractDownload PDF (1676K) -
Msaki OGAWA, Hideaki MATSUDA, Hiromichi ETO, Takemitsu ASAOKA, Tadayuk ...1991 Volume 39 Issue 9 Pages 2301-2307
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of vinylimidazoles containing a hetero atom such as sulfur or oxygen at a β-position of the vinyl group was prepared and the antifungal activities were tested. It was found that sulfur-substituted derivatives such as (E)-1-[2-(methylthio)-1-[2-(pentyloxy)phenyl]ethenyl]-1H-imidazole (5a-5) and (E)-1-[1-[2-(hexyloxy)phenyl]-2-(methylthio)ethenyl]-1H-imidazole (5a-6) showed exvellent antifungal activities against dermatophytes and yeast cells. The stereochemistry of the hydrochloride salt of 5a-5 was determined by X-ray crystallography. The structure-activity relationships were discussed.View full abstractDownload PDF (907K) -
Hiroshi OKADA, Tohru KOYANAGI, Nobutoshi YAMDA, Takahiro HAGA1991 Volume 39 Issue 9 Pages 2308-2315
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeventy novel benzoylphenylurea compounds were synthesized and their antitumor activities were examined in vivo against P388 leukemia. N-(2-Nitrobenzoyl)-N'-[4-(2-pyrimidinyloxy)phenyl]ureas showed the highest antitumor activities when dosed intraperitoneally or orally. Their structure-activity relationships were examined with particular focus on the position and the variety of subsitituent on each aryl ring.View full abstractDownload PDF (964K) -
Yusuke SASAKI, Akihiro AMBO, Kenji SUZUKI1991 Volume 39 Issue 9 Pages 2316-2318
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTyr-D-Arg-Phe-βAla-NH2 (I) and its six fluorinated analogs were synthesized. Their opioid receptor binding properties were examined in vitro and their analgesic activity in vivo using the mouse writhing test. It was found that I was one of the most selective and potent μ-receptor agonists reported to date. [Tyr(2F)1](VI) and [Tyr(3F)1](V) derivatives of I showed similar biological properties to those of I. Since these peptides resist enzymatic degradation, it is expected that they are excellent reagents for the studies of function of μ-receptor-mediated biological properties in vivo and in vitro.View full abstractDownload PDF (543K) -
Tadashi HASHIMOTO, Hiroko MASUI, Yoshiki UCHIDA, Naoki SAKURA, Keiko O ...1991 Volume 39 Issue 9 Pages 2319-2322
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo study the structure-actibity relationships of neuromedin U-8 (NMU-8) (H-Tyr-Phe-Leu-Phe-Arg-Pro-Arg-Asn-NH2) and to develop a NMU-8 antagonist, twenty-three NMU-8 analogs substituted with Gly or the corresponding D-amino acid(s) at positions 1-8 were synthesized by solid-phase techniques. On isolated chicken crop preparations, the contractile activity of the synthetic NMU-8 analogs was compared with that of NMU-8 and their antagonistic activity was assayed against NMU-8. The replacement of Phe2, Phe4, Arg5, Pro6, Arg7 or Asn8 with Gly brought about a drastic decrease of the agonistic activities. Substitution of the corresponding D-amino acid residue for Phe2, Phe4, Arg5, Pro6 or Asn8 caused a marked decrease of the agonistic activites, while the replacement of Tyr1 with D-form enhanced the activity. It was further revealed that [D-Pro6]-HMU-8 and [D-Leu3, D-Pro6]-MNU-8 exerted a non-competitive antagonistic activity against NMU-8 with x values of 5.22±0.12 and 5.34±0.09, respectively. [D-Phe2, D-Pro6]-NMU-8, [D-Arg5, D-Pro6]-NMU-8 and [D-Pro6, D-Asn8]-NMU-8 showed a very weak antagonism. The results indicated that 1) the side chain of each amino acid at positions 2, 4, 5, 6, 7 and 8 of NMU-8 is of relative importance for the expression of the contractile activity, and 2) [D-Pro6]-NMU-8 and its four analogs acted as an antagonist against NMU-8.View full abstractDownload PDF (706K) -
Youichiro NAITO, Tomokazu GOTO, Fumihiko AKAHOSHI, Shiniciro ONO, Haru ...1991 Volume 39 Issue 9 Pages 2323-2332
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-[4-(thiazol-2-yl)phenyl]propionic acids substituted at various positions were propared by the reaction of diethyl 2-methyl-2-(4-thiocarbamoylphenyl)malonates with α-bromoaldehyde diethyl acetals or α-haloketones followed by hydrolysis of esters. The inhibition of prostaglandin H synthetase (cyclooxygenase) was assayed by use of an enzyme preparation from guinea pig polymorphonuclear leukocytes. Examination of the structure-activity relationship of these compounds indicated that the subsititution pattern with halogens at position 3 (R1) of the benzene ring and a methyl group in position 4 (R2) and/or 5 (R3) of the thiazole ring were favorable for inhibitory activity. The compounds bearing bulky alkyl or polar functional groups at the R2 position were weak inhibitors. The potent inhibitors of cyclooxygenase were tested for their ability to reduce carrageenin-induced inflammation of rat paws. These derivatives had strong anti-inflammatory activity based on their strong inhibition of cyclooxygenase, with some exceptions, including those with a thiomethyl group at R1.View full abstractDownload PDF (1335K) -
Setsuo SAITO, Kaoru KURODA, Yasunobu HAYASHI, Yuka SASAKI, Yoichi NAGA ...1991 Volume 39 Issue 9 Pages 2333-2339
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGlycyrrhetic acid glycosides (1-7) having β(1→2)-linked disaccharides such as 2-O-β-D-glucopyranosyl-β-D-galactopyranose, 2-O-β-D-galactopyranosyl-β-D-galactopyranose, 2-O-β-D-glucuronopyranosyl-β-D-galactopyranose, 2-O-β-D-glucopyranosyl-β-D-glucuronopyranose, 2-O-β-D-galactopyranosyl-β-D-glucuronopyranose, 2-O-β-D-galactopyranosyl-β-D-glucopyranose, 2-O-β-D-glucuronopyranosyl-β-D-glucopyranose, respectively, were synthesized by stepwise construction; from glucyrrhetic acid monoglycosides to the diglycosides. The cytoprotective activities of the glycosides 1-7 and 2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl-11-oxoolean-12-en-30-oate (8) were compared with natural occurring glycyrrhizin (9). Among these glycosides 1-8, glycosides 3 and 7 having β-D-glucuronopyranose (glcUA) as the only terminal sugar component were more effective materials against hepatic injury than glycyrrhizin 9.View full abstractDownload PDF (1021K) -
Naoki TENO, Keiko WANAKA, Yoshio OKADA, Yuko TSUDA, Utako OKAMOTO, Aki ...1991 Volume 39 Issue 9 Pages 2340-2346
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSActive center-directed inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and then synthesized. Their effects on plasmin were examined and the structure-inhibitory activity relationship was studied. Nα-trans-4-Aminomethylcyclohexanecarbonyllysine 4-benzoylanilide (Tra-Lys-BZA) inhibited plasmin activities toward S-2251 and fibrin with IC50 values of 15 and 6.1 μM, respectively and Nα-trans-4-aminomethylcyclohexanecarbonyllysine 4-benzylpiperidine amide (Tra-Lys-BPP) did not show any detectable inhibitory activity. Moreover, it was revealed that Tra-Lys-4-methoxycarbonylanilide inhibited plasma kallikrein more potently than plasmin.View full abstractDownload PDF (945K) -
Yan-Nong SONG, Masaaki SHIBUYA, Yutaka EBIZUKA, Ushio SANKAWA1991 Volume 39 Issue 9 Pages 2347-2350
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the natural gene-transfer system of Agrobacterium tumefaciens, the expression of virulence (vir) gene of Ti (tumor inducing) plasmid is essential for the subsequent transferred deoxyribonucleic acid (T-DNA) transfer from bacterium to plant cells. vir gene expression is induced by signal compounds from pants such as acetosyringone and α-hydroxyacetosyringone which were isolated from hairy root cultures of Nicotiana tabacum. In a search for intrinsic signal compounds in plants, acetosyringone and α-hydroxyacetosyringone were identified as the vir-inducing compounds of the hairy root cultures of Atropa belladonna. The signal compounds of seedlings of Pisum sativum were identified as sinapyl and coniferyl alcohols. The quantities of these vir-inducing compounds were significantly increased when plant tissues were wounded, though the degree of increase was markedly different in each plant.View full abstractDownload PDF (765K) -
Yoshitaka IKEDA, Naomichi ISHIDA, Chikara FUKAYA, Kazumasa YOKOYAMA, M ...1991 Volume 39 Issue 9 Pages 2351-2352
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe optical isomers, shikonin and alkannin, can be separated by chiral phase high performance liquid chromatography. The results of analysis have shown that the commercial standards of "shikonin" or "alkannin" as well as the red pigments extracted from the roots of some Boraginaceous plants contain both optical isomers in various proportions.View full abstractDownload PDF (388K) -
Yukihiro OZAKI, Nobuo KAWAHARA, Masatoshi HARADA1991 Volume 39 Issue 9 Pages 2353-2356
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present study was carried out to elucidate the anti-inflammatory effect of the mathanol extract obtained from the rhizomes of Zingiber cassumunar ROXB. and its active principles. The methanol extract was partitioned between ether and water, and then the ether-soluble fraction was extracted with n-hexane. The n-hexane-soluble fraction was chromatographed and part of the fraction was rechromatographed by silica gel column. Three compounds were isolated from the n-hexane-soluble fraction and the chemical structures of these compounds were identified as (E)-1-(3, 4-dimethoxyphenyl)but-1-ene, (E)-1-(3, 4-dimethoxyphenyl)butadiene and zerumbone. The anti-inflammatory activity of these fractions was investigated on carrageenin-induced edema in rats, as well as on acetic acid-induced vascular permeability and writhing symptoms in mice. The methanol extract (p.o.) showed both anti-inflammatory activity and analgesic activity. These activities shifted successively to ether-soluble and n-hexane-soluble fractions and to (E)-1-(3, 4-dimethoxyphenyl)but-1-ene. These results suggest that the anti-inflammatory action and analgesic action of Zingiber cassumunar is the result of the (E)-1-(3, 4-dimethoxyphenyl)but-1-ene that it contains.View full abstractDownload PDF (680K) -
Masami KARIKURA, Toshio MIYASE, Hisayuki TANIZAWA, Toshio TANIYAMA, Yo ...1991 Volume 39 Issue 9 Pages 2357-2361
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify some similarities and differences of decomposition modes between 20(S)-protopanaxadiol (20(S)-ppd) saponins, represented by ginsenoside Rb1 (Rb1) and ginsenoside Rb2 (Rb2), the devompositions of Rb1 and Rb2 in the rat gastrointestinal tract, 0.1 N NCl and crude hesperidinase were investigated in detail. As in the case of Rb2 reported previously, Rb1 was hydrolyzed to 20(R, S)-ginsenoside Rg3 in 0.1 N HCl. On the other hand, hydroperoxidation of Rb1 occurred in rat stomach; the major hydroperoxide was separated and identifed as the 25-hydroperoxy-23-ene derivative of Rb1 (VIII) by 1H- and 13C-nuclear magnetic resonance and fast atom bombardment mass spectrometry. The decomposition modes of 20(S)-ppd saponins (Rb1 and Rb2) differed from that of 20(S)-protopanaxatriol saponin (Rg1) in rat stomach. In rat large intestine, five decomposition products of Rb1 were observed by thin-layer chromatography, and these were identified as gypenoside XVII (G-XVII), ginesenoside Rd (Rd), ginsenoside F2 (F2), compound K (C-K) and VIII. The decomposition modes of Rb1 and Rb2, both 20(S)-ppd saponins, are considered to be different because of the hydrolysis rate in the terminal sugar moiety at the C-20 hydroxyl group in the rat large intestine. Using crude hesperidinase, Rb1 was decomposed to G-XVII, F2 and C-K, and Rb2 was decomposed to 3-O-β-D-glucopyranosyl-20-O-[α-L-arabinopyranosyl(1→6)-β-D-glucopyranosyl]-20(S)-ppd, F2 and C-K. Consequently, it appears that hydrolysis by β-glucosidase, which is present in the rat large intestine, is distinct from that by crude hesperidinase. Tetracycline-resistant bacteria decomposed both Rb1 and Rb2 to their respective prosapogenins, except for Rd, and their respective hydroperoxides, while Rd and hydroperoxides of Rb1 and Rb2 were produced by enteric enzymes.View full abstractDownload PDF (722K) -
Yutaka SASHIDA, Kazutomo ORI, Yoshihiro MIMAKI1991 Volume 39 Issue 9 Pages 2362-2368
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical study on the bulbs of Lilium (L.) mackliniae has led to the isolation of a total of 27 compounds, including nine new phenolics. The structures of the new compounds have been shown by spectral analysis and chemical degradation to be 4, 4'-di-O-acetyl-3, 6'-di-O-feruloylsucrose, 3, 4'-di-O-p-coumaroylsucrose, 3, 6'-di-O-p-coumaroylsucrose, 2'-O-acetyl-3, 4'-di-O-p-coumaroylsucrose, 3'-O-acetyl-3, 4'-di-O-p-coumaroylsucrose, (2S)-1-O-p-methoxycinnamoyl-2-O-β-D-glucopyranosylglycerol (methylregaloside D), (2S)-1-O-cinnamoyl-2-O-β-D-glucopyranosyl (regaloside J), (2S)-l-O-caffeoyl-2-Oβ-D-glucopyranosylglycerol (regaloside K) and (2R)-1-O-β-D-glucopyranosyl-2-O-caffeoylgly-cerol (regaloside L). In addition, several previously reported phenolic glycosides, steroidal saponins and steroidal alkaloid have been isolated and identified. The presence of the steroidal alkaloid supported the idea that L. mackliniae is taxonomically related to the genus Fritillaria.View full abstractDownload PDF (973K) -
Guo-Qing ZHANG, Masaaki KAI, Yosuke OHKURA1991 Volume 39 Issue 9 Pages 2369-2372
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-performance liquid chromatographic method involving postcolumn fluorescence derivatization is described for the quantification of five fragment peptides (methionine-enkephalin-Thr-Ser-Glu-Lys, methionine-enkephalin-Lys, methionine-enkephalin-Arg, leucine-enkephalin-Lys and leucine-enkephalin-Arg) released by tryptic digestion from the opioid peptide precursors (proopiomeranocortin and proenkephalins A and B) in rat brain tissues. The tissue proteins containing the precursors are hydrolyzed with trypsin to the fragment peptides. The peptides are separated on an Asahipak ODP-50 column and on-line detected fluorometrically by using hydroxylamine, cobalt(II) and borate buffer reagents. The detection limits (S/N=3) for the peptides are 0.7-2.8 pmol per 100 μl injected. The distribution of the precursors in the brain tissues was also discussed on the basis of the determined values of the fragment peptides.View full abstractDownload PDF (627K) -
Hiroshi HOSODA, Katsuyuki FUKUDA, Yohko GOTOH1991 Volume 39 Issue 9 Pages 2373-2377
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnzyme labeling of steroids by the p-nitrophenyl ester method was investigated in comparison with the N-succinimidyl ester method. The active ester of a testosterone or 11-deoxycortisol derivative was treated with β-galactosidase and horseradish peroxidase to give labeled antigens. Various molar ratios of steroid to enzyme and pH conditions were tested. Satisfactory immunoreactivities with an anti-steroid antibody in each enzyme immunoassay system were obtained with the labeled antigens prepared at pH 8.5 by the use of molar ratios higher than 30. The enzyme labeling method should be useful in the case of polar steroids or drugs, since the p-nitrophenyl ester is relatively stable when compared with the N-succinimidyl ester.View full abstractDownload PDF (752K) -
Yoshihiko INAMORI, Kazuki NISHIGUCHI, Natsuko MATSUO, Hiroshi TSUJIBO, ...1991 Volume 39 Issue 9 Pages 2378-2381
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTropolone (I) and hinokitiol (II) at concentrations of 50 ppm showed strong inhibitory activity on the growth of all plants examined. Compounds I and II completely inhibited the germination of the seeds of some plants at the same concentration. The phytogrowth-inhibitory activities of both compounds were higher than that of sodium 2, 4-dichlorophenoxyacetate (2, 4-D), which was used as a standard. Both compounds inhibited the growth of some plants even at a concentration as low as 10 ppm. On the other hand, unlike 2.4-D, I and II stimulated the growth of all plants at the low concentration of 1 ppm. At 7d after treatment with I and II, the amount of chlorophyll in leaves of Brassica camperstris L. subsp. rapa. HOOK. f. et ANDERS treated with both compounds was greatly decreased as compared with the control group.View full abstractDownload PDF (1636K) -
Mikio NISHIDA, Toru SASAKI, Hiroshi TERADA, Jun KAWADA1991 Volume 39 Issue 9 Pages 2382-2386
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe purpose of the present study was to locate a controversial site and to make generalizations about the effects of thyroidectomy (Tx) and streptozocin (STZ) on the distribution pattern of an individual fatty acid in microsomal fractions of the animals thus treated. The results obtained were compared with the reported data. The effects of Tx on C18 : 1, C<18 : 2>, and all detectable C20 and C22 species harmonized well within each species; however the effects of Tx on C16 species and C18 : 0 varied within each species. Meanwhile, all the effects of STZ were identical within the species, but were often in opposite directions between two adjacent species; e.g. C18 : 0 and C18 : 1. These findings strongly indicate that desaturation and elongation sites were independently affected by either Tx of STZ. The comparison suggested that controversial effects appeared in the distribution proper to species C18. Therefore, delta 9-desaturase activity in the microsomal fractions was measured, using stearoyl coenzyme A (CoA) as substrate, resulting in some partial reduction in Tx, but complete suppression in STZ-treated animals. The total contents of phospholipid and cholesterol in the microsomes were also measured. Results showed a significant increase in microsomes within the STZ-group, but almost no change in the Tx-group, indicating that the changes in an individual fatty acid component and in the total fatty acids do not always take place in parallel.View full abstractDownload PDF (813K) -
Tomoko TAKAHASHI, Naka MUROI, Masachika IRIE, Yoshio IKEGAMI1991 Volume 39 Issue 9 Pages 2387-2390
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMultiple forms of glucoamylases [EC 3.2.1.3] from Aspergillus saitoi and Rhizopus sp. were studied for their chitin binding. Two forms of Aspergillus enzyme, Gluc M1 and Glu M2, were bindable to chitin, whereas three forms of Rhizopus enzyme, Gluc1, Gluc2 and Gluc3, exhibited no significant binding; of these enzyme forms, only Gluc M1 and Gluc1 are bindable to raw starch. Both Gluc M1 and Gluc M2, lacking the C-terminal portion of Gluc M1, bound to chitin most favorably at pH 6.5 but with considerable different strength. The binding constants K of Gluc M1 and Gluc M2 to chitin at pH 6.5 and 4°C were 1.8×106 and 0.33×106M-1, respectively. Soluble starch necessitated a high concentration of 1.2% for 50% inhibition of chitin binding of Gluc M1, as compared with 0.069% for 50% inhibition of raw starch binding (J. Biochem. (Tokyo), 98, 663 (1985)). Chitin-bound Gluc M1 retained almost the same soluble starch-hydrolyzing activity as and about 3 times higher maltose-hydrolyzing and 3 times lower raw starch-digesting activities than free Gluc M1. Thus, a chitin-binding site is not always identical with a raw starch-binding site, and in Gluc M1 the former is located farther from the active site than the latter.View full abstractDownload PDF (686K) -
Yoshiteru WATANABE, Motoshi SUDA, Yoshiaki MATSUMOTO, Kazuo TAKAYAMA, ...1991 Volume 39 Issue 9 Pages 2391-2394
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dissolution behavior of the aspirin enteric granule prepared using acylglycerols, glyceryl monostearate (GMS) and glyceryl trilaurate (GTL), was investigated in vitro and in human subjects in a fasting or non-fasting state. Aspirin was slowly released from the granule in vitro at pH 1.2. No acceleration of the aspirin dissolution rate in the medium without lipase and cholic acid was observed when the pH level of the medium increased to a neutral region (pH 6.4). However, the dissolution of aspirin was significantly increased by increasing the concentrations of lipase and cholic acid in the medium. Lipase appears to play an essential role in the dissolution process of aspirin granules. In human subjects, the average levels of the cumulative amount of total salicylate excreted in a urine-time curve, and the mean residence time (MRT) obtained after oral administration of a granule in the fasting state were markedly delayed in comparison with the results observed using and aqueous solution and a crystalline form of aspirin. In comparing the fasting condition with the non-fasting condtion (after food ingestion), no significant difference was recognized in the total amount of salicylate excreted in urine to an infinite time (Ae(∞)), whether the MRT was obtained by granule, crystalline form or aqueous solution. It can be concluded that aspirin granule prepared by GMS and GTL has a property of pancreatic lipase-sensitive dissolution, and its bioavailability is unaffected by food intake.View full abstractDownload PDF (683K) -
Isao ADACHI, Akio MURASE, Masaharu UENO, Isamu HORIKOSHI1991 Volume 39 Issue 9 Pages 2395-2399
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSaponin-permeabilized polymorphonuclear leukocytes (PMNs) released β-glucuronidase, a lysosomal enzyme, dose-dependently in response to cupric phenanthroline (CuPh), a mild oxidant, which catalyzes the formation of disulfide bridges. The β-glucuronidase release induced by CuPh was inhibited by ehylene glycol bis(β-aminoehylether)-N, N, -N', N'-tetraacetic acid (EGTA). Both dithiothreitol (DTT) and N-(6-aminohexyl)-5-chloro-naphthlelne sulfonamide (W-7) also inhibited the β-glucuronidase release induced by CuPh. CuPh elicited a decrease in protein-bound free sulfhydryls simultaneously, and this decrease was not restored by EGTA treatment. CuPh inhibited Ca2+ uptake into Ca2+ store sites, and promoted a Ca2+ efflux from Ca2+ store sites. It also inhibited Ca2+-adenosine triphosphatase (ATPase) activity in permeable PMNs. DTT, a sulfhydryl reducing agent, suppressed both the β-glucuronidase release and the Ca2+ uptake in CuPh-treated permeable PMNs. On the other hand, chloromercuriphenylsulfonic acid (CMPS), a sulfhydryl modifier, decreased the amount of free sulfhydryls in protein and released β-glucuronidase in permeable PMNs dose-dependently, but EGTA did not inhibit either reaction. Neither CuPh nor CMPS released β-glucuronidase from intact PMNs. These results indicate that both CuPh and CMPS act on intra-PMN target molecules to exert their influence, but the involved mechanisms are different in nature. Alteration in calcium movement is responsible for the β-glucuronidase release in the CuPh-treated permeable PMNs.View full abstractDownload PDF (865K) -
Masayuki KITAGAWA, Tetsuya MIMURA, Makoto TANAKA1991 Volume 39 Issue 9 Pages 2400-2407
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain lead compounds for uricosuric diuretics, various polycyclic aryloxy acetic acids [isoindole derivative (7), quinazoline derivative (15), benzopyran derivative (20), xanthone derivative (24), benzofuran derivative (30) and indene derivative (36)] were prepared. These compounds were evaluated for diuretic activity in rats, uricosuric activity in rats and antihypertensive activity in 11-deoxycorticosterone acetate (DOCA)/salt hypertensive rats. Among the compounds, 20 showed potent diuretic, uricosuric and moderate antihypertensive activities. Therefore, we selected 20 as a lead compound for development of new uricosuric diuretics.View full abstractDownload PDF (1123K) -
Mikio NISHIKAWA, Kiichiro FUJII1991 Volume 39 Issue 9 Pages 2408-2411
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen 30 mg/ml aqueous hydrogenated castor oil consisting of 60 oxyethylene group (HCO-60) solutions were shaken under fluorescent light of about 500 lux in a water bath at 30°C or 60°C, hydroperoxide, formaldehyde, and formic acid were formed. An aqueous solution containing 10 mg/ml miconazole (MCZ), 100 mg/ml HCO-60, and 1 mg/ml lactic acid was sealed in ampoules and stored at various temperatures for 8d. At 40°C or above, the concentration of MCZ decreased accompanied by a decrease in pH and formaldehyde formation. However, in the presence of nitrogen, no degradation was observed. The degradation of MCZ was also observed in the presence of iron(II) ion and hydrogen peroxide. Degradation of MCZ and HCO-60 was prevented by the addition of hydroxy radical scavengers, especially potassium iodide and thiourea. These results indicate that hydroxy radicals generated by autoxidation of HCO-60 degraded MCZ.View full abstractDownload PDF (710K) -
Yasunori MORIMOTO, Sachihiko NUMAJIRI, Kenji SUGIBAYASHI1991 Volume 39 Issue 9 Pages 2412-2416
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of ion species and their concentration on the iontophoretic transport of benzoic acid through an artificial membrane [poly(vinyl acetate)] were investigated using a 2-chamber diffusion cell equipped with platinum electorodes and a constant current power source. The cathode side of the cell was filled with sodium benzoate solution, and the anode side with pottassium chloride, lithium chloride or teraethylammonium bromide solution. When the molar concentration of sodium benzoate in the cathode side (0.21 M) was the same as the potassium chloride in the anode side, the amounts of benzoate anion and potassium cation permeated through the membrane were greater with increasing current. With an increase in the concentration of benzoate anion in the cathode side and a constant concentration of potassium cation in the anode side, the amount of the former that permeated was proportional to the concentration applied, while permeation of potassium cation remained almost constant at a constant current of 0.2mA. Conversely, an increase in the concentration of potassium cation in the anode side with a constant concentration of benzoate anion in the cathode side resulted in an increase of the permeation of potassium cation and a decrease of that of benzoate anion, respectively, at the same constant current. When potassium chloride in the anode side was replaced by tetraethylammonium bromide, the amount of benzoate anion permeated was increased at a constant current of 0.2mA. These results may be explained by the following theory on the transport number of each ion through the artificial membrane : Current density calculated from ion flux throutgh the membrane was almost the same as that measured by observed current density. The results appeared to indicate that not only an ion species and its concentration in the donor solution but also ion species in the receiver solution should be considered when evaluating the iontophoretic transport phenomena.View full abstractDownload PDF (804K) -
Hiroaki NAKAGAMI1991 Volume 39 Issue 9 Pages 2417-2421
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method of increasing the dissolution rates of glass-forming, poorly water-soluble drugs was investigated. It is based on the concept of preparing the powder form of a glassy drug dispersed in an inert carrier by melting. Indomethacin (IMC) and griseofulvin were used as model drugs, and fumed silicon dioxide was used as the carrier. The drug-silica (1 : 2) mixture was heated until the drug melted. The properties of the solid dispersion thus obtained were examined using powder X-ray diffractometry (XRD), differential scanning calorimetry (DSC), infrared (IR) spectroscopy, and scanning electron microscopy (SEM). XRD showed that the drugs were converted from a crystalline state to an amorphous state in the solid dispersions. On DSC thermograms, a pure IMC glass showed an endothermic peak corresponding to glass transition, then an exothermic peak corresponding to transformation to a metastable crystal and an endothermic peak corresponding to melting of the metastable form. The IMC-silica solid dispersion, however, shows no transition peak in its thermogram, indicating that a solid dispersion is more stable to heat than pure glass. The drug-silica solid dispersions showed IR spectra characteristic of pure amorphous drugs but somewhat different from those of crystalline drugs. SEM revealed that the drug-silica solid dispersions had none of the characteristics observed in crystalline drugs. The dissolution rates of drugs from the solid dispersions were much higher than those from physical mixtures and from pure crystalline drugs.View full abstractDownload PDF (2072K) -
Masatake NIWA, Hidetoshi SUGINO, Shigeki TAKASHIMA, Tatsuko SAKAI, Yan ...1991 Volume 39 Issue 9 Pages 2422-2424
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new coumarin glucoside named daphneside was isolated along with two known coumarin glucosides, daphnin and daphnetin-8-glucoside, and two known phenylpropanoid glucosides, syringin and syringinoside, from a water-soluble fraction of Daphne arisanensis HAYATA (Thymelaeaceae) collected in Taiwan. The structure of daphneside was elucidated by spectroscopic and chemical methods.View full abstractDownload PDF (547K) -
Yoshiji TAKEMOTO, Teruyo MATSUMOTO, Yoshio ITO, Shiro TERASHIMA1991 Volume 39 Issue 9 Pages 2425-2428
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compounds, which are synthetic intermediates of renin inhibitors, could be prepared from (S)-leucine and (S)-phenylalanine, respectively, by employing highly stereoselective aldol reactions of O-methyl-O-trimethylsilyl ketene acetal with an (S)-α-amino aldehyde in the presence of titanium(IV) chloride as a key step. Maximum diastereoselectivity of the aldol reaction was found to be more than 95 : 5.View full abstractDownload PDF (824K) -
Takashi YANAGISAWA, Kazuhiro KOSAKAI, Chikako IZAWA, Tsuyoshi TOMIYAMA ...1991 Volume 39 Issue 9 Pages 2429-2432
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites of sodium 3-ethyl-7-isopropyl-1-azulenesulfonate (KT1-32, 1), a candidate as an anti-ulcer drug, and related compounds were synthesized. The effects of the compounds on anti-peptic activity were determined as compared to that of 1.View full abstractDownload PDF (578K) -
Kenji SAKAGAMI, Kunio ATSUMI, Yuichi YAMAMOTO, Atushi TAMURA, Takashi ...1991 Volume 39 Issue 9 Pages 2433-2436
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-[2-(2-Aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid (11, ME1206) and its 3-trans isomer (13) were prepared to test antibacterial activity. These compounds exhibited excellent antibacterial activity against both gram-positive and gram-negative bacteria, including β-lactamase producing strains. The pivaloyloxymethyl esters (12 and 14) of the compounds (11 and 13) were prepared by esterification with pivaloyloxymethyl iodide. Among them, pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate (12, ME1207) showed good urinary recovery after oral administration in mice.View full abstractDownload PDF (646K) -
Akira INADA, Yachiyo NAKAMURA, Mari KONISHI, Hiroko MURATA, Fusako KIT ...1991 Volume 39 Issue 9 Pages 2437-2439
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new ionone glucoside and a new phenylpropanoid rhamnoside, termed ampelopsisionoside (1) and ampelopsisrhamnoside (2), respectively, have been isolated from stems of Ampelopsis brevipedunculata (MAXIM.) TRAUTV. (Vitaceae) and their structures have been established based on lines of chemical and spectral evidence. Four known glycosides, tachioside (3), isotachioside (4), lyoniside (5), and 2-phenylethyl D-rutinoside (6), were also isolated.View full abstractDownload PDF (603K) -
Hai-Xue KUANG, Chun-Jie SHAO, Ryoji KASAI, Kazuhiro OHTANI, Zhen-Kun T ...1991 Volume 39 Issue 9 Pages 2440-2442
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdenophora tetraphylla (=A. triphylla, Campanulaceae) is a source of the traditional Chinese medicine "Shashen". From the roots of this plant, three new phenolic glycosides, called shashenosides I, II and III (2-4) were isolated together with siringinoside (1), β-sitosteryl-β-D-glucoside, linoleic acid and methyl stearate. The common aglycone of 2, 3 and 4 was identified as 3-methoxy-5-(2'-propenyl)-1, 2-benzenediol [=1-O-methyl-5-(2'-propenyl)-pyrogallol=6-hydroxyeugenol, 6], and the structures of 2 and 3 were elucidated as 2, 3-di-O-β-glucopyranoside and 3-O-α-arabinopyranosyl-(1→6)-β-glucopyranoside of 6, respectively. Shashenoside III (4) was formulated as 2-O-β-glucopyranoside of 3. No saponin was found in the roots.View full abstractDownload PDF (547K) -
Kazuhiro OHTANI, Chong-Ren YANG, Chikako MIYAJIMA, Jun ZHOU, Osamu TAN ...1991 Volume 39 Issue 9 Pages 2443-2445
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom fruits of Rubus foliolosus (Rosaceae), a traditional medicine used in Yunnan, China, seven labdane-type diterpene glycosides were isolated. Of these glycosides, five were identified as goshonosides-F1-5 (1-5) which have been isolated from leaves of R. chingii. Structures of two new glycosides, goshonosides-F6 (6) and -F7 (8), were elucidated as α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside of 13(E)-ent-labda-8(17), 13-diene-3β, 15, 18-triol and 3β, 15-di-O-β-D-glucopyranoside of 13(E)-ent-labda-8(17), 13-diene-3β, 15-diol. Goshonosides-F6 (6) and -F7 (8) were also isolated from the leaves of R. chingii.View full abstractDownload PDF (474K) -
Chieko MATSUBARA, Masahiro KAJIWARA, Hidemichi AKASAKA, Shinichiro HAZ ...1991 Volume 39 Issue 9 Pages 2446-2448
Published: September 25, 1991
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe carbon-13 nuclear magnetic resonance (13C-NMR) spectrum of 13C-labeled hyaluronic acid (HA, 1a) was measured to clarify the origin of the carbon atoms of HA. 13C-Labeled HA (1a) was obtained from the cell surface of Streptococcus zooepidemicus #104 after administration of [1-13C]-D-glucose (2). The isolated HA, which had a molecular weight of more than one million, showed three signals in the 13C-NMR spectrum with no chemical degradation. The results revealed that [1-13C]-D-glucose (2) was incorporated into the [1-13C]-D-dlucuronic acid units and [1-13C]-N-[13CH3]acetamido-glucosamine units of HA (1a). The predicted biosynthetic pathway of HA was confirmed by this experiment.View full abstractDownload PDF (475K)