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Volume 33, Issue 3
Displaying 1-50 of 64 articles from this issue
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HIDEYUKI HARUYAMA, HIDESHI KURIHARA, MICHIO KONDO1985 Volume 33 Issue 3 Pages 905-915
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProton nuclear magnetic resonance (1H-NMR) relaxation of saframycin A in C6D6 has been studied. Quantitative analysis of spin-lattice relaxation times and nuclear Overhauser effect (NOE) factors allowed the determination of the α-axial orientation of the nitrile group at C21, (previously unknown). The conformation of saframycin A in C6D6, which was deduced from the relaxation data, was compared with that of saframycin C in the crystal state.View full abstractDownload PDF (939K) -
YOSHIHIRO MORI, FUMIKO AKAGI, AKIRA YAJIMA, TAIJI KITAGAWA1985 Volume 33 Issue 3 Pages 916-926
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solid phase thermal decompositions of L-cystine and its three stereoisomers have been investigated in vacuo between 150 and 230°C. The decomposition processes have been examined by measuring the total pressure and the partial pressures of the four gaseous products, NH3, H2O, H2S, and CO2, as well as by the semiquantitative determination of sulfur polymers. The rate equation for the thermal decomposition of L-cystine can be approximated as zeroth order, with an induction period at the initial stage of the decomposition. A remarkable change in the reaction rate was found at around 170-180°C, above which evaporated sulfur polymers can be detected. At lower temperature the dehydration reaction is predominant, while the rates of formation of NH3, H2S, and CO2 become much larger than that of H2O as the temperature increases. The observed induction periods at T<200°C are different for each of the product gases, and depend strongly on the decomposition temperature and the history of the starting materials. The reactions that occur during this period are discussed. The different behavior observed in the thermal reactions of other sulfur-containing amino acids, L-cysteine and L-methionine, and some non sulfur-containing ones are discussed in relation to the different strengths of the hydrogen bond networks in the crystalline states.View full abstractDownload PDF (1021K) -
MASAFUMI GOTO, MASAO KOYAMA, HISAO USUI, MASAYOSHI MOURI, KOUJI MORI, ...1985 Volume 33 Issue 3 Pages 927-936
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix derivatives of N, N'-ethylenebis (3-tert-butylsalicylideneaminato) cobalt (II), abbreviated as Co (Busalen), were prepared by varying the diamine moiety with ethylenediamine, (R)-1, 2-propanediamine, (2S, 3S)-2, 3-butanediamine, meso-2, 3-butanediamine, (1R, 2R)-1, 2-cyclohexanediamine, and cis-1, 2-cyclohexanediamine. The spectral and electrochemical properties of the complexes are reported. These complexes and four derivatives of N, N'-ethylenebis (salicylideneaminato) cobalt (II), Co (salen), were used as catalysts for the oxygenation of 3-methylindole. With increasing steric hindrance of the metal complex catalyst, the rate of the steady-state consumption of the substrate increased, and the induction period increased with increasing steric hindrance at the apical region of Co (Busalen) derivatives. A linear relationship was found between the logarithm of the rate constants and the half-wave potentials for CoII/III couples : log (102k/mol-1dm-3s-1)=a (E1/2/V)+b, where a and b are 5.2 and -0.56 for the Co (Busalen) series, and 5.5 and -1.25 for the Co (salen) series, respectively. Based on these observations, it is concluded that the catalysis is controlled by the redox potential and tert-butyl groups of the Co (Busalen) derivatives, and the activation of the substrate, not dioxygen, is the critical step of this reaction.View full abstractDownload PDF (925K) -
TAKUMI MATSUDA, KENJI YAMAGATA, YUKIHIKO TOMIOKA, MOTOYOSHI YAMAZAKI1985 Volume 33 Issue 3 Pages 937-943
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMalononitrile reacts with 2-chloroethanol and 1-chloro-2-propanol (or 2-methyloxirane) in the presence of sodium ethoxide to give 2-amino-3-cyano-4, 5-dihydrofuran (Ia) and 2-amino-3-cyano-5-methyl-4, 5-dihydrofuran (Ib), respectively. The reaction of malononitrile with 2-phenyl-oxirane or 2-chloro-1-phenylethanol gave 2-amino-3-cyano-4 (and 5)-phenyl-4, 5-dihydrofurans (Ic and Id). The 2-benzamido derivatives (IIb-d) of Ib-d were aromatized by treatment with N-bromosuccinimide to give the corresponding furans (IIIb-d).View full abstractDownload PDF (756K) -
CHUZO IWATA, TOSHIYA MORIE, TETSUAKI TANAKA1985 Volume 33 Issue 3 Pages 944-949
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compound (8), a possible intermediate for the synthesis of aphidicolane and stemodane diterpenes, was synthesized by the decomposition of the phenolic α-diazoketone (9) in the presence of copper (II) chloride.View full abstractDownload PDF (674K) -
TAKEO HIGASHINO, HIROYASU KOKUBO, EISAKU HAYASHI1985 Volume 33 Issue 3 Pages 950-961
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N, N-dimethylformamide were investigated. The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively. The reaction with π-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c). Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3, 4-dihydro-4-quinazolinecarbonitriles (24a-c). The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrrolo [1, 2-c] quinazoline-1, 2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1, 2, 3, 4-tetrahydro-2, 4-ethenoquinazoline-9, 10-dicarboxylate (28). The reaction with 2-alkenonitriles (29a, b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl) alkanonitriles (32a, b).View full abstractDownload PDF (987K) -
YOSHINORI TOMINAGA, SHUICHIRO SAKAI, SHINYA KOHRA, JUNKO TSUKA, YOSHIR ...1985 Volume 33 Issue 3 Pages 962-970
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 3-amino-s-triazole (1) with ketene dithioacetals (2) gave 5-methylthio-s-triazolo [1, 5-a] pyrimidine derivatives in satisfactory yields. The synthesis of 7-amino-s-triazolo-[1, 5-a] pyrimidine derivatives is also described.View full abstractDownload PDF (702K) -
SUSUMU KITANAKA, HIROYOSHI IGARASHI, MICHIO TAKIDO1985 Volume 33 Issue 3 Pages 971-974
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the callus of Cassia occidentalis LINN., six anthraquinones [islandicin, chrysophanol, physcion, emodin, questin, and 7-methylphyscion (1)], a bianthrone (chrysophanol-10, 10'-bianthrone), three tetrahydroanthracenes [germichrysone, methylgermitorosone, and 7-methyltorosachrysone (2)], and a xanthone (pinselin) were isolated. The structures of the two new compounds, 1 and 2, were established on the basis of spectral and chemical evidence.View full abstractDownload PDF (508K) -
YUTAKA YAMAMOTO, YASUO MORITA1985 Volume 33 Issue 3 Pages 975-981
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRing transformations of 2-aryl-6-methyl-4H-1, 3-oxazin-4-ones (1-3) with carbanions derived from various ketones, esters, lactones, and nitriles to give 3-acetyl-4, 5, 6-trisubstituted-2-pyridone derivatives 12 were explored. 1, 3-Oxazin-4-ones (1-3) underwent initial attack of the carbanions at the 2-position of the ring to give the 2-substituted-2-aryl-3, 4-dihydro-2H-1, 3-oxazin-4-ones (9a-o). The dihydrooxazines (9a-g) bearing a quarternary-carbon substituent at the 2-position of the 1, 3-oxazine ring were stable. In contrast, the dihydrooxazines (9h-o) which possess a tertiarycarbon substituent at the 2-position were converted into the ring-opened acetoacetamide derivatives (11) and subsequently recyclized to the corresponding 3-acetyl-2-pyridone derivatives (12).View full abstractDownload PDF (672K) -
KENJI KAJI, HIROMU NAGASHIMA, YOSHIHIKO HIROSE, HIROHISA ODA1985 Volume 33 Issue 3 Pages 982-988
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 2-substituted 5-(1-methylhydrazino)-3 (2H)-pyridazinones (2a-d) with dimethyl-formamide-phosphorus oxychloride afforded 5-substituted 1, 5-dihydro-1-methyl-4H-pyrazolo [3, 4-d] pyridazin-4-ones (3a-d) in good yields. However, concurrent formation of 5-substituted 2, 5-dihydro-2-(2-substituted 1-chlorovinyl)-4H-pyrazolo [3, 4-d] pyridazin-4-ones (6a-c, 12, 13) (minor products) and the 1-methyl-4H-derivatives (3a-c) (major ones) was observed, when starting with the corresponding 2-substituted 5-(2-acetyl-1-methylhydrazino)-3 (2H)-pyridazinones (5a-c, 9, 10) under similar reaction conditions. A plausible mechanism for the reaction is proposed.View full abstractDownload PDF (744K) -
MASAHITO OCHIAI, EIICHI FUJITA, MASAO ARIMOTO, HIDEO YAMAGUCHI1985 Volume 33 Issue 3 Pages 989-997
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidative cyclization of hydroxy allylsilanes utilizing the combination of a hypervalent organoiodine compound and a Lewis acid was studied. The allylsilanes 4, prepared from the γ-lactones 1 via conversion to the bis (trimethylsilylmethyl) carbinols 3, on treatment with iodosyl-benzene in the presence of boron trifluoride-etherate in an ethereal solution, afforded the 6-membered β-methylene cyclic ethers 13a and 13b in good yields. Similar treatment of the allylsilanes 8a and 8b gave the 5-membered cyclic ethers 13a and 13b. On the other hand, oxidative cyclization of the carboxylic acid 12 gave a poor yield of the lactone 21 and the major product was found to be the rearranged γ-keto acid 22. Regioselectivity in the iodine (III)-mediated cyclization of 8a is discussed.View full abstractDownload PDF (919K) -
KINUKO IWASA, MAKIKO SUGIURA, NARAO TAKAO1985 Volume 33 Issue 3 Pages 998-1008
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrolysis and photolysis of the N-oxides of the protopines 9 and 16 produces the ring-enlarged compounds 10 and 17, whose reduction with zinc in acetic acid leads to the secoberbines (±)-corydalisol (11) and (±)-hypecorine (12) from 9, and the corresponding analogs (18 and 19) from 16. Pyrolysis of (+)-chelidonine N-oxide (24) generates dihydrosanguinarine (22).View full abstractDownload PDF (1154K) -
MASANAO TERASHIMA, KOHICHI SEKI, CHIHIRO YOSHIDA, KAZUE OHKURA, YUICHI ...1985 Volume 33 Issue 3 Pages 1009-1015
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of a mixture of 2-iodopyridine and a variety of substituted benzenes in dichloromethane afforded the corresponding 2-arylpyridines as isomeric mixtures. Based on the isomer distributions of the products and the formation of 2-chloropyridine as a by-product, the reactivity of 2-iodopyridine in the present reaction was suggested to be electrophilic in character.View full abstractDownload PDF (690K) -
AKIMORI WADA, SHOICHI KANATOMO, SOTOO NAGAI1985 Volume 33 Issue 3 Pages 1016-1022
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSortho-Directed lithiation of a number of (2-methoxy) ethoxy- and (2-dimethylamino) ethoxyarenes has been investigated. Lithiation of these compounds followed by treatment with various electrophiles afforded ortho-substituted products in moderate to excellent yields.View full abstractDownload PDF (756K) -
TOZO FUJII, MASASHI OHBA, HITOSHI SUZUKI1985 Volume 33 Issue 3 Pages 1023-1028
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of securing a key intermediate for chiral syntheses of the 10-hydroxy-9-methoxybenzo [a] quinolizidine-type Alangium alkaloids (type 4), the tricyclic ester (-)-15 has been synthesized from ethyl cincholoiponate [(+)-6] and 4-benzyloxy-3-methoxyphenacyl bromide by the "cincholoipon-incorporating method"through the intermediates (+)-7, 10, 8, (-)-11, (-)-12, (+)-13, (+)-14, (+)-17, and 16.View full abstractDownload PDF (668K) -
MANABU NODE, NOZOMU ITO, ITSUO UCHIDA, EIICHI FUJITA, KAORU FUJI1985 Volume 33 Issue 3 Pages 1029-1033
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new kaurene-type diterpenoids, shikoccin (1), O-methylshikoccin (2), epoxyshikoccin (3), O-methylepoxyshikoccin (4) and shikoccidin (5) were isolated from Rabdosia shikokiana var. occidentalis. All these compounds except for 5 possess a hitherto unknown 8, 9-seco-ent-kaurene skeleton.View full abstractDownload PDF (546K) -
KAORU FUJI, NOZOMU ITO, ITSUO UCHIDA, EIICHI FUJITA1985 Volume 33 Issue 3 Pages 1034-1037
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Jones oxidation of shikoccin (1), the major diterpenoid of Rabdosia shikokiana var. occidentalis, unexpectedly provided products 3 and 4. Tetrahydroshikoccin (6) afforded the abietane-type compound 11 upon Jones oxidation.View full abstractDownload PDF (453K) -
KAORU FUJI, MANABU NODE, NOZOMU ITO, EIICHI FUJITA, SETSUO TAKEDA, NOR ...1985 Volume 33 Issue 3 Pages 1038-1042
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn vitro antitumor activity of diterpenoids isolated from Rabdosia shikokiana var. occidentalis was determined against HeLa cells. Some of these compounds possess considerable activity against Ehrlich ascites carcinoma inoculated into mice. In particular, the epoxyketone 7 derived from shikoccin (1) showed potent activity. The in vivo activity of shikoccin (1) against six tumor lines was evaluated.View full abstractDownload PDF (496K) -
YINGJIE CHEN, TADAHIRO TAKEDA, YUKIO OGIHARA1985 Volume 33 Issue 3 Pages 1043-1048
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe prosapogenins from the partial hydrolysate of fruit saponin of Xanthoceras sorbifolia BUNGE (Sapindaceae) were examined. On the basis of chemical and spectral analyses, compound G was identified as protoaescigenin (1). Two new prosapogenins were characterized as 16-O-acetyl-21-O-(3', 4'-di-O-angeloyl)-β-D-fucopyranosylprotoaescigenin (5) and 22-O-acetyl-21-O-(3', 4'-di-O-angeloyl)-β-D-fucopyranosylprotoaescigenin 3-O-β-D-glucuronopyranoside (7).View full abstractDownload PDF (631K) -
HIROSHI HOSODA, HIROMITSU YOKOHAMA, HIROAKI SHIOYA, TOSHIO NAMBARA1985 Volume 33 Issue 3 Pages 1049-1054
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of the 3-glucuronides of 11-deoxycortisol metabolites is described. 3α, 17α, 20α-Trihydroxy-5β-pregnan-21-oic acid 3-glucuronide (13) and its 20β-epimer (14) were prepared starting from 5β-dihydro-11-deoxycortisol (1). The 20-acetoxy-21-oic acid methyl esters (7, 8) were the key intermediates. Oxidation of 1 with cupric acetate followed by the intramolecular Cannizzaro reaction gave the 20-epimeric 20-hydroxy-21-acids (5, 6), which, on methylation with diazomethane followed by acetylation, were converted into the acetate-methyl esters (3, 4). Reduction of the carbonyl group at C-3 in 3 and 4 with sodium borohydride gave the desired intermediates. Introduction of the glucuronyl residue at the C-3 position was carried out by means of the Koenigs-Knorr reaction. 20-Epimeric 5β-pregnane-3α, 17α, 20, 21-tetrol 3-glucuronides (26, 27) were also prepared.View full abstractDownload PDF (789K) -
HIROSHI SUEMUNE, AIRI AKASHI, KIYOSHI SAKAI1985 Volume 33 Issue 3 Pages 1055-1061
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical synthesis of platelet-activating factor (PAF, 1) and its enantiomer was studied. Several alkoxymethyl alkenyl ketones (5a-c, n=14 or 16) were synthesized from Wittig-Horner reagents (4, n=14 or 16) with cyclohexanecarboxaldehyde, octylaldehyde, and benzaldehyde, and subjected to asymmetric reduction with BINAL-H1) which is known to show high enantioselectivity in the reduction of enones. Optical purities of the reduction products (6) were determined from the 400 MHz proton nuclear magnetic resonance spectra after conversion of 6 to the esters (9) of optically active α-methoxy-α-trifluoromethyl-phenylacetic acid (MTPA). The MTPA ester of (+)-6b showed high optical purity (80%ee). Upon oxidative cleavage of the double bond with ozone followed by reduction with NaBH4, the acetate of (+)-6b afforded two known compounds (11 and 12), which have previously been transformed into natural PAF (1).View full abstractDownload PDF (745K) -
TOZO FUJII, MASASHI OHBA, SHIGEYUKI YOSHIFUJI, SHIGEAKI AKIYAMA1985 Volume 33 Issue 3 Pages 1062-1068
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the effect of an N-substituent on thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system, the N-alkyl analogs (±)-1b, c and (±)-2b, c and the N-(2-arylethyl) analogs (-)-1f, g, i and (+)-2f, g, i were separately heated neat at 180°C, and the propress of their cis-trans isomerization reactions was followed by determining the isomer ratios in the reaction mixtures according to the previously reported C-13 nuclear magnetic resonance spectroscopic method. It has been found that in all cases the reaction comes to equilibrium within 28-130 min, when the cis and trans isomers exist in a ration of 1 : 2. These results together with those obtained previously with the analogs (±)-1a, d, e, (-)-1h, (±)-2a, d, e, and (+)-2h indicate that a higher and/or bulkier N-substituent tends to decrease the rate of cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system, which is a useful synthon for the synthesis of benzo-[a] quinolizidine-type Alangium alkaloids. Among the substrates used in the present equilibration study, (±)-1b, c and (±)-2b, c were prepared from the corresponding N-unsubstituted lactam esters (±)-3 and (±)-7 by the"lactim ether method."View full abstractDownload PDF (777K) -
ISAO KITAGAWA, MASAYUKI SAITO, TOSHIO TANIYAMA, MASAYUKI YOSHIKAWA1985 Volume 33 Issue 3 Pages 1069-1076
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive bioactive triterpene-oligoglycosides, named soyasaponins I, II, III, A1 (3), and A2 (2), were isolated from soybean, the seeds of Glycine max MERRILL (Leguminosae). By employing a photochemical degradation method and a lead tetraacetate degradation method, which are two of four selective cleavage methods available for the glucuronide linkage in oligoglycosides, the structure of soyasaponin A1 was elucidated to be 3-O [β-D-glucopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl]-soyasapogenol A (3).View full abstractDownload PDF (905K) -
TAIKO ODA, YOSHIHIRO SATO1985 Volume 33 Issue 3 Pages 1077-1082
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo elucidate the stereochemistry of the hydrogenation of (-)-dehydrogriseofulvin (1a) to (+)-griseofulvin (3a) by Streptomyces cinereocrocatus, we have prepared from the microorganism a cell-free system which can transform 1a to 3a. The hydrogenation activity of the cell-free system increased in the presence of added reduced nicotinamide adenine dinucleotide phosphate (NADPH). The stereochemistry of hydrogenation was determined by 400 MHz proton nuclear magnetic resonance (1H-NMR) analysis of the products obtained by the enzymatic conversion of (-)-[5'-2H]-dehydrogriseofulvin (1b) and also by the enzymatic conversion of 1a in medium containing deuterium oxide.View full abstractDownload PDF (683K) -
YAEKO KONDA, HIROSHI TAKAHASHI, MASAYUKI ONDA1985 Volume 33 Issue 3 Pages 1083-1087
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPantherine is identified as 5-aminomethyl-3-hydroxyisoxazole by means of spectroscopic experiments and chemical correlation with synthetic compounds.View full abstractDownload PDF (594K) -
KAZUHIRO HIRAKURA, YOSHIO HANO, TOSHIO FUKAI, TARO NOMURA, JUN UZAWA, ...1985 Volume 33 Issue 3 Pages 1088-1096
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new stilbene derivatives, named kuwanons P and X, as well as a new 2-arylbenzofuran derivative, named mulberrofuran J, were isolated from the acetone extract of the root bark of cultivated mulberry tree (Japanese name"Roso, "a variety of Morus lhou KOIDZ.) together with a known 2-arylbenzofuran derivative, albafuran C. The structures of the new compounds were elucidated on the basis of the spectral evidence, and the compounds can be regarded biogenetically as Diels-Alder type adducts of chalcone derivatives and dehydroprenylphenols. In view of the biogenetic route to 2-arylbenzofuran derivatives, involving oxidative cyclization of hydroxystilbenes, it is noteworthy that two stilbene derivatives, kuwanons P (1) and X (2), coexist with two 2-arylbenzofuran derivatives, albafuran C (4) and mulberrofuran J (3), in the mulberry root bark.View full abstractDownload PDF (931K) -
YASUMITSU TAMURA, TAKAYUKI YAKURA, YOSHIAKI SHIROUCHI, JUNICHI HARUTA1985 Volume 33 Issue 3 Pages 1097-1103
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidative 1, 2-aryl migration of alky aryl ketones (2, 5, and 8) to 2-arylalkanoates (3, 6, and 9) was effected by using diacetoxyphenyliodine (1). The migration was successfully applied to the preparation of the antiinflammatory agents ibuprofen (15) and clidanac (17).View full abstractDownload PDF (677K) -
HARUKI TAKAI, HIROYUKI OBASE, NOBUHIRO NAKAMIZO, MASAYUKI TERANISHI, K ...1985 Volume 33 Issue 3 Pages 1104-1115
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of piperidine derivatives with various heterocyclic rings at the 4-position was prepared and tested for antihypertensive activity and other biological activities. The antihypertensive effects of the present compounds in the spontaneous hypertensive rat were less potent than those of previously reported compounds. However, among the compounds tested for antiulcer activity and antiinflammatory activity, some exhibited interesting properties.View full abstractDownload PDF (1213K) -
HARUKI TAKAI, HIROYUKI OBASE, NOBUHIRO NAKAMIZO, MASAYUKI TERANISHI, K ...1985 Volume 33 Issue 3 Pages 1116-1128
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 1-and 3-(1-substituted 4-piperidinyl)-1, 2, 3, 4-tetrahydro-2-oxoquinazolines were synthesized and tested for antihypertensive activity. Among the compounds tested, 1-(2-hydroxy-2-phenethyl)-4-(1, 2, 3, 4-tetrahydro-2-oxo-3-quinazolinyl) piperidine derivatives were generally the most effective in lowering blood pressure in the spontaneous hypertensive rat model. Of these, 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-4-(1, 2, 3, 4-tetrahydro-2-oxo-3-quinazolinyl) piperidine (26) (KF5908) seemed the most promising.View full abstractDownload PDF (1148K) -
HARUKI TAKAI, HIROYUKI OBASE, MASAYUKI TERANISHI, AKIRA KARASAWA, KAZU ...1985 Volume 33 Issue 3 Pages 1129-1139
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGeneral synthetic methods for the preparation of 4-(2-aminophenyl)-4-hydroxypiperidine derivatives have been developed. The application use of these derivatives in the synthesis of 1'-substituted spiro [4H-3, 1-benzoxazine-4, 4'-piperidin]-2 (1H)-one derivatives is described, and the antihypertensive activity of the products is also reported.View full abstractDownload PDF (1117K) -
TAKAO NISHI, FUJIO TABUSA, TATSUYOSHI TANAKA, TAKEFUMI SHIMIZU, KAZUYU ...1985 Volume 33 Issue 3 Pages 1140-1147
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites of 6-[4-(1-cyclohexyl-1H-5-tetrazolyl) butoxy]-2-oxo-1, 2, 3, 4-tetrahydroquinoline (OPC-13013) (1), which has a potent inhibitory activity toward blood platelet aggregation and a cerebral vasodilating activity, were synthesized to confirm their structures and to examine their inhibitory activity. The structures of four major metabolites (2a-c and 3) and a specific metabolite (4) found only in man were identified unequivocally by means of comparisons with the synthetic compounds. The inhibitory activity of 3, 4-dehydro-OPC-13013 (3) was about three times higher than that of 1, whereas two metabolites (2a and 2c) had activity almost equal to that of 1.View full abstractDownload PDF (744K) -
HIDEJI ITOKAWA, HIROSHI MORITA, KINZO WATANABE, SUSUMU MIHASHI, YOICHI ...1985 Volume 33 Issue 3 Pages 1148-1153
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new sesquiterpenoids, 3α, 4α-oxidoagarofuran, 3β, 4β-oxidoagarofuran, 3β, 4β-oxidoagarofuran and Δ9 (10)-eremophilen-11-ol, as well as 10-epi-γ-eudesmol, 4α-hydroxydihydroagarofuran, α-agarofuran, dihydroagarofuran and β-eudesmol were isolated from the rhizome of Alpinia japonica. Their structures were determined by chemical and spectroscopic methods. It is interesting from a biogenetic point of view that Δ9 (10)-eremophilen-11-ol, β-eudesmol and agarofurans which possess the 10-epimeric eudesmane carbon skeleton were all contained in the same plant.View full abstractDownload PDF (610K) -
SHIGEO IKEGAWA, UTAKO NIITSU, TAKAO KUROSAWA, MASAHIKO TOHMA1985 Volume 33 Issue 3 Pages 1154-1158
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe preparation and antigenic properties of estradiol-bovine serum albumin conjugates in which the haptens are linked to the carrier protein through a glycine amide linkage at the 12α and the 12β positions on the steroid molecule are described. The antigens raised high-titer and reasonably specific antisera in rabbits, exhibiting little or no cross-reactivities with related steroids, with the exceptions of estrone (8.33%, 38.2%) and 16-oxoestradiol (7.90%, 5.65%).View full abstractDownload PDF (602K) -
KIYOSHI ZAITSU, HIROYUKI HOSOYA, YOHJI HAYASHI, HIDENORI YAMADA, YOSUK ...1985 Volume 33 Issue 3 Pages 1159-1163
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method for the mutual separation of six citraconylated porcine insulins and intact insulin from the reaction mixture of insulin with citraconic anhydride is described, based upon anionexchange high-performance liquid chromatography on a TSK IEX-540 DEAE column. The method permits the preparative isolation of citraconylinsulins. The optimal reaction conditions for the preparation of GlyAlPheBl-dicitraconylinsulin, a useful starting material for the preparation of Lys-B29 modified insulin derivatives, were also investigated.View full abstractDownload PDF (639K) -
AKIRA TAKADATE, MITSURU IRIKURA, TSUTOMU SUEHIRO, HIROYUKI FUJINO, SHU ...1985 Volume 33 Issue 3 Pages 1164-1169
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-Methoxycoumarin-3 (and 4)-carbonyl azides (I and II) were synthesized as highly sensitive fluorescent labeling reagents for use in high-performance liquid chromatography (HPLC). Treatment of 7-methoxycoumarin-3 (and 4)-carbonyl chlorides with a suspension of activated sodium azide in dry acetone gave I and II in 56% and 54% yields, respectively. Compounds I and II reacted with alcohols in dichloromethane to give the corresponding highly fluorescent 7-methoxycoumarin-3 (and 4)-carbamic acid esters (IIIa-e and IVa-g). 4-Amino-7-methoxycoumarin (V), isolated as a by-product on labeling with II, was also obtained by heating II in tetrahydrofuran. Mixtures of primary and secondary alcohols were labeled with I or II and chromatographed on a reversed-phase HPLC column (mobile phase : methanol-water and methanol-chloroform) with a fluorescence detector. The detection limits of a test sample, cholesterol, were 50fg and 10ng/100μl on labeling with I and II, respectively.View full abstractDownload PDF (657K) -
HIDEKI KAWASAKI, SAYOSHI NINOMIYA, HIDETAKA YUKI1985 Volume 33 Issue 3 Pages 1170-1174
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-performance liquid chromatographic method is described for the determination of 3-methylcytosine (m3Cyt) in deoxyribonucleic acid (DNA). Calf thymus DNA was methylated with N-methyl-N-nitrosourea or N-methyl-N'-nitro-N-nitrosoguanidine in vitro. Methylated rat liver DNA was obtained by administration of dimethylnitrosamine to rats. The DNA samples were hydrolyzed with perchloric acid at 100°C for 1 h, and after the removal of perchloric acid by the use of anion exchange resin, the filtrate was concentrated and loaded on a Dowex 1×2 anion exchanger. The eluted cytosine derivatives were collected and injected into a liquid chromatograph. The content of m3Cyt in methylated DNA was successfully determined by this method. The amount of m3Cyt increased with the dosage of methylating agent in vitro, but showed no significant dose-dependent increase in vivo.View full abstractDownload PDF (516K) -
MACHIKO MATSUBARA, HISATORA KURODA1985 Volume 33 Issue 3 Pages 1175-1180
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure and composition of conidial cell walls of Cochliobolus miyabeanus were studied. Analyses by means of gas liquid chromatography, high performance liquid chromatography, enzymatic digestion and nuclear magnetic resonance and infrared absorption spectroscopy revealed that the acid-soluble neutral polysaccharide was composed of β-1, 6-and β-1, 3-linked glucosyl residues in the ratio of 2 : 3, that the branched units connected through C6 or C3 of the main-chain glucan, and that nonreducing termini existed in the ratio of one residue to five glycosyl residues. Amino acid analysis indicated the presence of glycine, alanine, aspartic acid, serine, leucine, glutamic acid, proline and threonine in decreasing order of contents. The acid-alkaliinsoluble polysaccharide was identified as chitin by enzymatic digestion, X-ray diffraction and infrared spectral analyses.View full abstractDownload PDF (596K) -
NAOHITO OHNO, KAZUYOSHI IINO, IWAO SUZUKI, SHOZO OIKAWA, KICHIRO SATO, ...1985 Volume 33 Issue 3 Pages 1181-1186
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWater-soluble glucan fractions extracted from the cultured fruit bodies of Grifola frondosa with hot water, and with cold and hot sodium hydroxide containing urea showed potent antitumor activity in mice (Ohno et al., Chem. Pharm. Bull., 32, 1142 (1984)). Each fraction was separated into neutral and acidic glucan fractions on a DEAE-Sephadex A-25 (HCO3-) column. Both neutral and acidic fractions showed potent antitumor activity against Sarcoma 180 solid tumor in ICR mice. From the results of methylation analysis and carbon-13 nuclear magnetic resonance spectroscopy, the neutral fractions contained mainly α-1, 4 and 6-branched β-1, 3 linkages, and the acidic fractions contained mainly β-1, 6-and 6-branched β-1, 3 linkages. The branching ratio was similar in both glucans. By colorimetric analysis, each acidic fraction was found to contain about 2-5% uronic acid. These findings indicated that the cultured fruit bodies of Grifola frondosa contain neutral and acidic antitumor glucans.View full abstractDownload PDF (629K) -
JUN WATANABE, YAYOI HAYASHI, KIKUO IWAMOTO, SHOJI OZEKI1985 Volume 33 Issue 3 Pages 1187-1194
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSalivary excretion of 5-fluorouracil (5-FU) was investigated following bolus intravenous administration (20mg/kg) in four beagle dogs. Parotid (Pr) and mandibular-sublingual saliva (MS) were collected separately by stimulating salivation with 10% citric acid. Significant correlations were observed between 5-FU concentrations in plasma and in each saliva (p<0.01). However, the saliva/plasma drug concentration ratios (S/P ratios) showed fairly large fluctuations (0.472±0.303 for Pr, 0.200±0.196 for MS) and were not influenced by protein concentration in saliva or salivary flow rate. The observed S/P ratios were significantly different from the S/P ratios calculated by the use of Matin's equation which employed the observed salivary pH values and free fraction of 5-FU in plasma and saliva (p<0.001). Therefore, it was concluded that the salivary excretion of 5-FU cannot be explained by pH-partition theory. Total salivary clearance of 5-FU (0.123±0.093ml/min/kg) was less than 0.5% of total body clearance. In each saliva, salivary clearance of 5-FU was almost independent of salivary flow rate. The relationship between salivary clearance and plasma 5-FU concentration is discussed.View full abstractDownload PDF (880K) -
KIMIKO MAKINO, MASAYUKI ARAKAWA, TAMOTSU KONDO1985 Volume 33 Issue 3 Pages 1195-1201
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolylactide (PLA) microcapsules with an average diameter of 1.5μm were prepared by an interfacial deposition technique. The degree of degradation of PLA microcapsules was estimated by determination of the amount of lactic acid as a final product in bulk solution and from the molecular weight distribution of PLA of the microcapsules remaining undegraded by means of gel permeation chromatography using chloroform as the eluent. The rate of hydrolytic degradation of PLA microcapsules prepared by using poly (D, L-lactide) or poly (L-lactide) was extremely pH-dependent ; it was slowest at pH around 5.0 and it increased in both strongly acidic and strongly alkaline solutions. The activation energy of deesterification at pH 7.4 and ionic strength 0.15 was calculated to be 19.9kcal/mol for poly (D, L-lactide) microcapsules and 20.0 kcal/mol for poly (L-lactide) microcapsules, when the initial weight-average molecular weight was about 100000 for both polymers. These values are comparable to those found for the hydrolysis of alkyl acetates.1) In buffer solution (pH 9.6), the hydrolytic degradation was enhanced when the ionic strength of the medium was increased. Chromatographic analysis of the products of hydrolytic degradation suggested that OH- or H3O+ attacks the ester bonds located in the crystalline zone, followed by further cleavage of the initial products into fractions with lower molecular weights. Carboxylic esterase promoted the degradation by cleaving the ester bonds located in the crystalline zone directly. Urea and NaSCN accelerated the degradation effectively, while AlCl3, CaCl2, and KCl had no or little effect on the degradation rate. Poly (L-lactide) microcapsules were degraded less rapidly than poly (D, L-lactide) microcapsules.View full abstractDownload PDF (714K) -
HIROSHI FUJIWARA, SUSUMU KAWASHIMA1985 Volume 33 Issue 3 Pages 1202-1213
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was proved that bacampicillin hydrochloride (BAPC) is degraded according to a parallelconsecutive reaction scheme consisting of the direct deactivation reaction of β-lactam cleavage and the process through ampicillin (ABPC) in aqueous solution. In particular, the degradation of the 3-carboxylate of BAPC was faster than that of the β-lactam, and BAPC was transformed quite easily to ABPC in the alkaline region (pH 7.00-9.00). However, the degradation of the β-lactam and that of the ester moiety of BAPC were inhibited due to adduct formation upon addition of benzaldehyde at this pH region. On the other hand, such a stabilization was not observed in the acidic region (pH<6.00) because no adduct formation developed. The formation constant of the adduct increased with increase of pH. On the basis of the above results and infrared and mass spectra of the freeze-dried product prepared from an alkaline solution containing BAPC and benzaldehyde, the adduct was concluded to be the Schiff's base formed between the α-amino group of BAPC and benzaldehyde ; a similar adduct is formed by ABPC.View full abstractDownload PDF (935K) -
KOJI YAMADA, HIDEKI NIINO, TAMOTSU HASHIMOTO, KATSUICHI SHUTO, NOBUHIR ...1985 Volume 33 Issue 3 Pages 1214-1220
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew and known analogues of 2, 2'-dithiodibenzamide were synthesized and tested for various pharmacological actions. This series of compounds was found to inhibit collagen-and adenosine 5'-diphosphate-induced aggregations of blood platelets. 2, 2'-Dithiobis (N-(2-hydroxypropyl) benzamide) (3, KF4939) was one of the most potent compounds in in vitro aggregometry studies. Compound 3 after oral administration also potently inhibited pulmonary thrombosis induced by arachidonic acid injection in mice and platelet aggregation ex vivo in rats. This compound may have clinical value as a new orally active inhibitor of platelet aggregation.View full abstractDownload PDF (711K) -
KOUICHI YAMANOUCHI, MIKIO TANAKA, YOSHIO TSUDA, KAZUMASA YOKOYAMA, SHO ...1985 Volume 33 Issue 3 Pages 1221-1231
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuantitative structure-activity relationships of a series of perfluorochemicals (PFCs) for use as oxygen transporters were investigated in terms of their in vivo half-lives (t1/2). The logt1/2 values can be correlated by a linear combination of lipophilic (e.g., critical solution temperature (CST)), physicochemical (e.g., molecular weight and vapor pressure (Pv)) and topological (e.g., number of fluorines (NOF)) parameters on regression analyses. The most important excretion-rate-determining factor was the CST. The Pv alone of PFCs did not correlate well with logt1/2. However, a combination of CST and Pv produced the most meaningful and important correlation, indicating that Pv plays a pivotal role in the excretion and can be considered a kind of correction factor to the CST. The t1/2 can thus be predicted from the combination of CST and Pv. It can also be predicted from structural information : the smaller the NOF, the shorter the t1/2. The incorporation of hetero atom (s) such as nitrogen and oxygen in the PFC molecule, which has been considered to produce better emulsion stability but results in persistence in the body, had relatively little effect in terms of t1/2. These results suggested that, taking the emulsifiability of hetero atom-containing PFCs into consideration, a cyclic F-ether and F-tertiary amine with fused ring (s), containing fewer fluorines than acyclic analogues, might be a good candidate compound as an oxygen transporter.View full abstractDownload PDF (949K) -
HIROKI TSUKAMOTO, SUEO HISADA, SANSEI NISHIBE1985 Volume 33 Issue 3 Pages 1232-1241
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new lignans, (+)-1-acetoxypinoresinol-4'-β-D-glucoside (1), (+)-1-acetoxypinoresinol-4'-β-D-glucoside 4"-O-methyl ether (2), (+)-1-hydroxypinoresinol-1-β-D-glucoside (4) and (+)-fraxiresinol-1-β-D-glucoside (5), and a known lignan, (+)-1-hydroxypinoresinol-4'-β-D-glucoside (3), were isolated from the bark of Olea europaea L. and the bark of Olea africana MILL. (Olea europaea L. subsp. africana (MILL.) GREEN) (Oleaceae). Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. The bark of Olea capensis L. did not yield any lignan glucosides.View full abstractDownload PDF (1001K) -
WEIMIN HOU, SHOZO MIYAZAKI, MASAHIKO TAKADA1985 Volume 33 Issue 3 Pages 1242-1248
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn ethylene-vinyl alcohol (EVAl) copolymer was evaluated as a new carrier for a long-acting delivery system of pilocarpine-HCI. The release characteristics of pilocarpine-EVAl copolymer matrix (film or beads) systems were investigated in in vitro and in vivo test models. The results of the in vitro study suggested that the drug release rate could be easily controlled by modifying the proportions of ethylene and vinyl alcohol in the copolymer. Sustained release can be obtained by using EVAl copolymer containing more ethylene. The results of the in vivo study indicated that the use of the pilocarpine-EVAl copolymer bead system is more effective than that of the conventional liquid dosage form for prolonging the duration of a desired pupillary response. Its biocompatibility, flexibility, and heat processability suggest the EVAl copolymer to be a good candidate for pilocarpine delivery into the eye.View full abstractDownload PDF (786K) -
YOSHIHISA KURASAWA, YOSHIHISA OKAMOTO, ATSUSHI TAKADA1985 Volume 33 Issue 3 Pages 1249-1255
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe proton nuclear magnetic resonance (1H-NMR) spectra of some 3-(1, 3, 4-oxadiazol-5-ylmethylene)-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines and 3-(1, 2, 4-triazol-5-ylmethylene)-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines were measured in dimethylsulfoxide-d6 (DMSO-d6), trifluoroacetic acid (TFA), and TFA-d1. The spectra in DMSO-d6 indicated that 2, 3, 4, and 5 existed as the two tautomers A and B, and 6, 7, and 8 as a single tautomer. From the spectra of 2, 3, 4, and 5 in DMSO-d6, it was elucidated that tautomer A was predominant over tautomer B at low temperature, while the ratio of the tautomer B gradually increased with increase of the temperature. The spectra in TFA indicated that 2 occurred as the three tautomers C, D, and E, while 3, 4, and 5 existed as a single tautomer, D. Compounds 6 and 7 also appeared to isomerize in TFA, that is, 6 existed as the two tautomers C and E, while 7 existed as two of the three tautomers C, E, and G. Compound 8 was predominantly present in the form of tautomer C or E.View full abstractDownload PDF (574K) -
TOMIKI HASHIYAMA, HIROZUMI INOUE, MIKIHIKO KONDA, MIKIO TAKEDA1985 Volume 33 Issue 3 Pages 1256-1259
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of the cis-3-arylglycidic esters 2 and 10 with thiophenols (3) has been investigated. The reactivity and stereoselectivity of the oxirane ring-opening of these cis-glycidic esters were lower than those of the trans-analogues (1 and 9). These tendencies were more apparent in the 4-MeO derivative (2). On the other hand, the tin-catalyzed reaction of 2 with 3a was highly stereospecific and afforded the cis-opening product (5a).View full abstractDownload PDF (494K) -
MASARU KIHARA, YOSHIYUKI MIYAKE, MORIO IITOMI, SHIGERU KOBAYASHI1985 Volume 33 Issue 3 Pages 1260-1265
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe apogalanthamine analogs 4- and 9-bromo-5, 6, 7, 8-tetrahydrodibenz [c, e] azocines (5a and 6a) and their methylenedioxy derivatives (5b and 6b) were prepared by photolysis of the hydrochlorides of the respective N-benzyl-β-phenethylamines (8a, b and 9a, b) substituted with both iodine and bromine atoms. The dibenz [c, e] azocines 6a and 6b were also obtained by thermal syntheses from the biphenyl compounds 17a and 17b, respectively.View full abstractDownload PDF (682K) -
SHIRO URANO, SHUNICHIRO NAKANO, MITSUYOSHI MATSUO1985 Volume 33 Issue 3 Pages 1266-1269
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS[12'a, 13'-13C] all-rac-α-Tocopherol (1) was synthesized from [1, 3-13C] acetone. The condensation of 6-methoxymethoxy-2, 5, 7, 8-tetramethyl-2-[(E)-4-methyl-5-(thiazolin-2-yl) thio-3-penten-1-yl] chroman (8) with [7a, 8-13C] geranyl bromide (7), which was prepared by the coupling of (E)-(6-benzoyloxy-4-methyl-4-hexen-1-yl) triphenylphosphonium bromide (5) with [1, 3-13C] acetone, followed by bromination, afforded 6-methoxymethoxy-2, 5, 7, 8-tetramethyl-2-[12a, 13-13C] (3E, 7E, 11E) 4, 8, 12-trimethyl-5-(thiazolin-2-yl) thio-3, 7, 11-tridecatrien-1-yl] chroman (9). After desulfurization and reduction of 9, the reaction product was converted to [12'a, 13'-13C] all-rac-α-tocopherol (1) by the use of methanolic hydrogen chloride. The overall yield of 1 was 33% on the basis of [1, 3-13C] acetone.View full abstractDownload PDF (489K) -
SHIZUO TODA, TOSHIO MIYASE, HIDEKO ARICHI, HISAYUKI TANIZAWA, YOSHIO T ...1985 Volume 33 Issue 3 Pages 1270-1273
Published: March 25, 1985
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntioxidative components in the methanol extract of seeds of Plantago asiatica L. were investigated by using our test method based on the air oxidation of linoleic acid. Geniposidic acid, an iridoid glucoside, was found to be the most potent antioxidative component. The 50% inhibitory concentration (IC50) of geniposidic acid was 1.56×10-2% (thiobarbituric acid value), and this value was superior to that of dl-α-tocopherol (IC50 : 1.95×10-1%). The antioxidative effects of other related iridoid glucosides (aucubin, geniposide, gardenoside) were also tested, but their activities were clearly weaker than that of geniposidic acid.View full abstractDownload PDF (474K)