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HIROSHI NAKAGAWA, TATSUHIKO MIYATA, ISAO SUGIMOTO
1978 Volume 98 Issue 10 Pages
1305-1310
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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The disintegration and dissolution behavior of tablets containing berberine chloride dihydrate or tetrahydrate were investigated. The disintegration time of the dihydrate tablet and tetrahydrate tablet was 30 and 4 min, respectively, and the dissolution rate of berberine chloride from the former was much slower than that from the latter. The reason for this difference was considered and the following conclusion was obtained. When dihydrate was transformed to tetrahydrate in water, the fine crystals of tetrahydrate grew on the crystal surface and network structure was formed between crystals, resulting in the decreased the penetration rate of water into the tablet and inhibition of the release of particles from the tablet into water. Consequently, disintegration time of the tablet increased and dissolution rate of berberine chloride decreased. Under storage at 20°and relative humidity of 75%, dihydrate in the tablet was transformed to tetrahydrate, and the disintegration time of the tablet decreased. At 50°, tetrahydrate in the tablet was transformed to dihydrate, and the disintegration time of the tablet increased.
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MASAYUKI NAKAGAKI, SATOSHI OKADA
1978 Volume 98 Issue 10 Pages
1311-1318
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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The concentration dependence of pH of each of six phenothiazine hydrochlorides (PTZ·HCl) in aqueous solution was measured at 25°. Below the critical micelle concentration (cmc), the pH decreased slowly with increasing concentration. Just above the cmc, the pH decreased rapidly, and then decreased gradually with further increase of the concentration. Below the cmc, the pH change was mainly due to the acid dissociation of monomer PTZH
+, but slightly affected by dissolved carbon dioxide. On the other hand, above the cmc, not only the monomer but aggregated PTZH
+ also dissociates, and the acid dissociation constant of the latter was greater than that of the former. Proton balance equation was derived on the system, where two independent weak acids coexist. According to this equation, the concentration dependence of pH was culculated for the coexistence of the monomer and carbon dioxide below the cmc and for the coexistence of the monomer and micelle above the cmc. Measured pH change with the concentration was consistent with the calculated one at two separate regions, below and above the cmc. The difference in pK
a between the monomer and aggregated PTZH
+ (ΔpK
a) was obtained on each PTZH
+, which was related to the electrostatic work of micelle formation, and to the surface potential of PTZH
+ micelle.
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TSUGUCHIKA YOSHIDA, NOBUO YUNOKI, YUKI NAKAZIMA, TSUNETOSHI KAITO, TOS ...
1978 Volume 98 Issue 10 Pages
1319-1326
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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A simultaneous determination of vitamin B
6 group in blood was developed using a high-performance liquid chromatograph (HPLC) equipped with a fluorescence detector. Pyridoxamine, pyridoxal, pyridoxine, deoxypyridoxine (internal standard), and pyridoxic acid were separated on Toyo Soda Gel LS-160 column (8×500mm) using 0.0045 M NaClO
4-0.04 M KH
2PO
4-2 M NaCl (pH 5.5) as an eluent. The blood sample added with citrate buffer and internal standard was deprotenized with trichloroacetic acid (TCA) and shaken with ether and hexane to remove excess TCA. A 100-μl portion of the remaining aqueous solution was injected into HPLC column and the effluent was monitored by fluorescence detector (Ex 325 nm, Em 385 nm). Since B
6 5'-phosphates were not separated on this column, they were determined as a free form of B
6 after hydrolysis by acid phophatase. The detection limits were 0.1 nmol/ml blood for pyridoxal 0.2 nmol/ml for pyridoxamine and pyridoxine, and 0.3 nmol/ml for pyridoxic acid. The concentration of B
6 group in the blood after oral administration of pyridoxal, 5'-phosphate to rabbits and dogs was determined by this method. It was found that pyridoxic acid and pyridoxal were the major metabolites present in rabbit blood, whereas no metabolites other than pyridoxal were detected in dog blood.
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SEIJI NAGUMO, KAZUO IZAWA, MASAHIRO NAGAI
1978 Volume 98 Issue 10 Pages
1327-1332
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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From the underground parts of Pertya robusta (Compositae) were isolated O-methyl pertyol (I) and a new tetracylic triterpene methyl ether (III), C
32H
54O, mp 162-162.5°, [α] D+84°, in addition to bauerenyl acetate (X), friedelin (XI), and friedelan-3β-ol (XII). The structure of III was established to be (24S) 3β-methoxy-24-methyllanosta-9 (11), 25-diene by synthesis of the dihydro derivative of III from 24-methylenecycloartanol. Distribution of triterpene components (I, III, X, XI, XII and taraxeryl acetate (XIII)) was investigated from the chemotaxonomic standpoint of Pertya spp.
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MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, KAZUHIRO ONOGI
1978 Volume 98 Issue 10 Pages
1333-1340
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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In order to examine the utility of triphenylmethyl hexachloroantimonate (1) for organic synthesis, various kinds of hexachloroantimonates of carbonium ion were prepared by the reaction of 1 with equimolar amount of various kinds of appropriate cyclic compounds. These products were obtained in a simple and stable manner compared to the synthesis of corresponding perchlorates. Experimental studies were also made on the limitation of 1 as an anion (H
-, OH
-, Cl
-, etc.) abstraction reagent, using various kinds of 6, 11-dihydrodibenzo [b, e] thiepin derivatives.
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MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, KAZUHIRO ONOGI
1978 Volume 98 Issue 10 Pages
1341-1348
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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In order to examine the reaction of 6, 11-dihydrodibenzo [b, e] thiepin-11-ones (21) and antimony pentachloride, reaction of various ketones with SbCl
5 or HCl-SbCl
5 was carried out. Tricyclic ketones (1a-d) gave the corresponding protonation products (9a-d) but monocyclic ketones, such as diphenylcyclopropenone (13) and γ-pyrone (19) only formed ketone-SbCl
5 adducts (1 : 1) (12, 18) with SbCl
5 and protonation products (14, 20) with HCl-SbCl
5. Stereochemical considerations were made on the formation mechanism of these products. Reaction of 6, 11-dihydrodibenzo [b, e] thiepin-11-one (21) with SbCl
5 gave the anticipated protonation product (22) but that of 6-chloro-6, 11-dihydrodibenzo [b, e] thiepin-11-one (5) and SbCl
5 resulted in cleavage of the thiepin ring, contrary to expectations, and a compound (23) of undetermined structure was obtained. This compound (23) transited to bis [2-(2-formylbenzoyl) phenyl] disulfide (24) by hydrolysis.
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MITSUTOMO TSUHAKO, CHINUYO OYAMA, TSUNEO MATSUO, ITARU MOTOOKA, MASAMI ...
1978 Volume 98 Issue 10 Pages
1349-1355
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Oligo and polyphosphoric acids contained in metaphosphoric acid solution were analysed by ion-exchange chromatography (exponential gradient elution) as well as by paper chromatography. Hydrolytic degradation of metaphosphoric acid and the stability of ascorbic acid in the presence of metaphosphoric acid were also studied. Metaphosphoric acid was proved to be a mixture of various phosphoric acids, from orthophosphoric acid (P
1) to octaphosphoric acid (P
3) and long chain phosphoric acid (coiled chain phosphoric acid) above pentadecaphosphoric acid (P
15) as well as trimetaphosphoric acid (P
3m), one of ring phosphoric acids. When an aqueous solution of metaphosphoric acid was allowed to stand for many hours, chain phosphoric acids above triphosphoric acid (P
3) and P
3m were degradated hydrolytically to form P
1 and pyrophosphoric acid (P
2), and finally to form only orthophosphoric acid. However, even after standing for 120 days, a slight amount of coiled chain phosphoric acid still remained. Hydrolytic degradation of metaphosphoric acid in an ascorbic acid solution proceeded almost similarly to that of metaphosphoric acid alone, but the rate of degradation of metaphosphoric acid in a mixed solution of ascorbic acid, a metallic ion, and metaphosphoric acid, was considerably faster than that of metaphosphoric acid alone. On the other hand, oxidation of ascorbic acid was remarkably depressed by the presence of metaphosphoric acid. Metaphosphoric acid was proved to be effective in preventing oxidation of ascorbic acid in the presence of any metallic ion. Oxidation of ascorbic acid is accelerated by metallicions, in the order of Cu
2+>Fe
3+>Sn
2+.
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MASAYUKI NAKAGAKI, MIEKO TAGAWA
1978 Volume 98 Issue 10 Pages
1356-1360
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Preparation of ferric hydroxide sol by using L-alanine was investigated in order to find a condition for obtaining a concentrated and stabilized sol in the near neutral pH range for manufacture of an iron-containing medicine. Ferric hydroxide was peptized by addition of its precipitate into L-alanine solution containing hydrochloric acid and boiling for 8 hr. The degree of peptization was evaluated by the concentration of ferric hydroxide in the sol thus formed. The concentration was determined by chelatomery after dissolving the colloidal particles into ferric ions. Although no peptization took place in the concentration range of 0.001-0.1 N of L-alanine, addition of a small amount of hydrochloric acid to it induced peptization. The degree of peptization depends on the concentration of L-alanine and hydrochloric acid. It was found that the prefered pH was 4-6 for the molar ratio between the precipitate and L-alanine of 0.1-0.2. Thus, the effect of L-alanine to peptize ferric hydroxide was recognized in the near neutral pH range. The mechanism of peptization was discussed from these results.
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YOSHIKI HAMADA, MICHIHARU SUGIURA, MINORU HIROTA
1978 Volume 98 Issue 10 Pages
1361-1369
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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1, 3-Dialkoxy-4-bromo-2-cyano-1, 2, 3, 4-tetrahydroisoquinolines (2ab, 8ab to 11ab) are obtained quantitatively by the addition of cyanogen bromide to isoquinoline (1) dissolved in the corresponding alcohol, followed by application of bromine and saturated sodium carbonate solution. These products are a mixture of stereoisomers with the hydrogen atoms in 3- and 4-positions in cis (main) and trans configuration. Dehydrobromination of the cis-type compounds with potassium cyanide easily gives 3-alkoxyisoquinolines (7, 12-15). Hydrolysis of with conc. hydrochloric acid affords 4-bromoisoquinoline (5a) from cis-type compounds and 4-chloroisoquinoline (5b) from trans-type compounds. It had been difficult to obtain compounds 7 and 12 to 15. 4-Bromo-5-nitroisoquinoline (21) was obtained from 5-nitroisoquinoline (18) by the application of the above reaction but 3-methoxy-5-nitroisoquinoline (22) could not be obtained. Application of this reaction to 1, 6-naphthyridine easily gave 8-bromo-1, 6-naphthyridine (27) and 7-methoxy-1, 6-naphthyridine (28), compounds in which a substituent had been introduced into the 7- and 8-positions that had never been attempted so far.
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TAKUO KOSUGE, MASAMI YOKOTA, MICHIO NAGASAWA
1978 Volume 98 Issue 10 Pages
1370-1375
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Aconite root (Bushi in Japanese) from Aconitum japonicum THUMB. has long been used as one of the most important herbs as a heart stimulant, diuretic agent ; and anodyne in Chinese medichine. Isolation and identification of the cardiac principle predicted by Yakazu are described. In the isolation process, the Yagi-Hartung method using frog heart was found to be useful for pharmacological measurement of cardiac activity of the material. The material was water soluble and was fairly unstable, especilly in a basic medium, and was tightly adsorbed on charcoal, alumina, silica gel, and cellulose powder, indicating that these agents are not useful for the separation. Isolation of the material was finally achieved by the limited combination of gel filtration through Sephadex LH-20 and counter current distribution, and colorless plates, mp 260°, were obtained as HCl salt. This principle stimulates frog heart even 1 : 10
-9 dilution, and it was designated as Higenamine. Higenamine was identified as dl-demethylcoclaurine (II) from the spectral data and by comparison with synthesized authentic sample.
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SHINICHIRO SAKAI, NOBUO SHINMA, SUGIO HASEGAWA, TOSHIHIKO OKAMOTO
1978 Volume 98 Issue 10 Pages
1376-1384
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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The alkaloids of Aconitum gigas LEV. et VAN. which was collected in Hokkaido, were reexamined. In addition to the reported lycaconitine, two known compounds, lycoctonine and atisine hydrochloride, and a new base, named gigactonine, were isolated. The structure of gigactonine was deduced from a few chemical reactions and its
13C-nuclear magnetic resonance spectrum, and it was established that 18-O-methylgigactonine was identical with the known diterpenoid alkaloid, delsoline. From oxidation reactions and the above-emntioned correlation, the structure of gigactonine was established. Furthermore, bases I and V were also isolated from the same plant as the artifacts of lycaconitine.
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JUTARO OKADA, YOSHIKO HIRAI
1978 Volume 98 Issue 10 Pages
1385-1390
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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During a direct-compression, the effect of magnesium stearate as a lubricant was examined. Potassium chloride, lactose, sodium bicarbonate powder, and their lubricated powder were filled and compressed by the upper punch, measuring the upper punch pressure, lower punch pressure, and thickness of the powder bed. In the case of lubricated powders, three patterns for the three unlubricated powders in changes of pressuretransmission ratio with the increase of upper punch pressure changed to the type of monotonous increase, and the pressure-transmission ratio increased. remarkedly. On the other hand, the lubricated powders showed a lower porosity than the unlubricated powders, but they remained in the same patterns of the porosity-upper punch pressure curve for each of unlubricated powders. Photomicrographs of the replicated surface of lubricated and unlubricated tablets were compared. The lubricated tablets showed equalization of density by distribution.
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JUTARO OKADA, SHUSHI MORITA, YOSHIHISA MIWA, TOSHIO TASHIMA
1978 Volume 98 Issue 10 Pages
1391-1394
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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The vapor-phase ammoxidation of 2, 5-lutidine was studied in a flow reactor system at atmospheric pressure. This reaction was carried out over several catalysts, V
2O
5-Al
2O
3, V
2O
5-K
2O-Al
2O
3, V
2O
5-pumice stone, V
2O
5-MoO
3-pumice stone, and V
2O
5-Cr
2O
5-pumice stone, The activity and selectivity of these catalysts were compared for the synthesis of dicyanopyridine. The best catalyst among them was 1% Cr
2O
3-10% V
2O
5-pumice stone. Over this catalyst, 2, 5-dicyanopyridine was produced with 60% yield at a temperature of 410° and the side reaction to 3-cyanopyridine was negligible. The effect of temperature, contact time, partial pressure of ammonia, and partial pressure of oxygen were also studied. It was found that this reaction is a consecutive reaction in which the methyl group at 2-position is oxidized at first and 2, 5-lutidine was converted to 2-cyano-5-methyl-pyridine, which was then oxidized to 2, 5-dicyanopyridine.
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AKIYO SAKUSHIMA, SANSEI NISHIBE, SUEO HISADA
1978 Volume 98 Issue 10 Pages
1395-1397
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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From the methanolic extract of leaves of Apocynum venetum L. var. basikurumon HARA, eight constituents were isolated and identified with respective authentic samples as succinic acid, chlorogenic acid, isoquercitrin, hyperoside, D-(-)-bornesitol, sucrose, β-sitosterol, and β-amyrin.
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HISASHI ICHIBAGASE, YORISHIGE IMAMURA, AYAKA SUENAGA, HIROHUMI KAWABAT ...
1978 Volume 98 Issue 10 Pages
1398-1402
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Effect of the continuous administration of pyridinolcarbamate (Pc) on the renal excretion of sulfonamides was investigated in rabbits. The continuous Pc administration significantly decreased the renal excretion of N
4-acetylsulfanilamide and N
4-acetyl-sulfadimethoxine, which are major metabolites of sulfanilamide and sulfadimethoxine. On the other hand, continuous Pc administration did not affect the renal excretion of unchanged sulfanilamide and unchanged sulfadimethoxine. It has been known that N
4-acetylsulfanilamide and N
4-acetylsulfadimethoxine are excreted by both the glomerular filtration and tubular secretion, but unchanged sulfanilamide and unchanged sulfadimethoxine are excreted by only the glomerular filtration. Therefore, the present experimental results suggest that the continuous Pc administration inhibits the tubular secretion of N
4-acetylsulfanilamide and N
4-acetylsulfadimethoxine.
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HISASHI ICHIBAGASE, YORISHIGE IMAMURA, AYAKA SUENAGA, EMI UENO
1978 Volume 98 Issue 10 Pages
1402-1405
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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HISASHI ICHIBAGASE, YORISHIGE IMAMURA, AYAKA SUENAGA, KOJI YOSHIDA, TA ...
1978 Volume 98 Issue 10 Pages
1406-1409
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Continuous administration of pyridinolcarbamate (Pc) significantly decreased the renal excretion of phenolsulfonphthalein and p-aminohippuric acid, which are excreted exclusively by the tubular secretion. On the other hand, continuous Pc administration had little effect on the renal excretion of mannitol and inulin, which are excreted exclusively by the glomerular filtration. These results suggest that the continuous Pc administration competitively inhibits the tubular secretion of some drugs.
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SHIZUO FUKUDA, RYOZO KOSHIURA, KENICHI MIYAMOTO
1978 Volume 98 Issue 10 Pages
1409-1412
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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In order to elucidate the mechanism of action of new antitumor agents like bis-(haloalkyl) piperidine derivatives, sensitivity of various deoxyribonucleic acid (DNA) repair-deficient mutants of Eschericha coli B to these derivatives was examined. When bacteria were treated with 1-(β-chloroethyl)-2-chloromethylpiperidine hydrobromide (CAP-1), ultraviolet-sensitive (uvrA
-) mutant and recombination-deficient (recA
-) mutant were killed and DNA polymerase I-minus (pol I
-) mutant was moderately killed. The killing kinetics of CAP-1 on bacteria was very similar to those of ultraviolet ray. These reapir-deficient mutants were remarkably sensitive to 1-(γ-chloropropyl)-2-chloromethyl-piperidine hydrobromide (CAP-2), and its killing kinetics was similar to those of mitomycin-C. Moreover, in the case of 2, 6-bis (iodomethyl) piperidine hydrochloride (CAP-12), pol I
- mutant was very rapidly killed and recA
- and uvrA
- mutants were moderately killed, though the viability of wild type strain was hardly affected. These results indicate that the higher sensitivity of repair-deficient E. coli mutants to bis (haloalkyl) piperidine derivatives is mainly due to their impaired repair ability for DNA damage caused by these derivatives. Therefore, it is concluded that these derivatives act on bacterial DNA and produce DNA lesions repairable by the repair systems of the wild type strain.
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HIROSHI FUJITO, YOSHINORI TOMINAGA, HIROSHI AWAYA, KEIJI KURATA, YOSHI ...
1978 Volume 98 Issue 10 Pages
1412-1416
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Desulfurization of pyridinium and isoquinolinium 3-cyano-2-methylthioallylides (I, II) with Raney-nickel gave the corresponding desulfurized pyridinium and isoquinolinium allylides. Treatment of I and II with 10% sodium hydroxide solution afforded the indolizine and pyrrolo [2, 1-a] isoquinoline derivatives, respectively. The reaction of I with hydrazine hydrate gave pyrazole derivatives in a good yield.
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KENJI SHIMADA, MITSUO IKEDA, YUZO NAGASE
1978 Volume 98 Issue 10 Pages
1417-1421
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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As reported previously p-dimethylaminocinnamaldehyde reacts with 4-aminoantipyrine to produce an intense color, which can be used as an analytical reagent. A similar color reaction and colorimetric determination were examined with other aminopyrinerelated compounds, 4-formylaminoantipyrine (I), 4-monomethylaminoantipyrine (II), and 4-acetylaminoantipyrine (III), and optimum reaction conditions for color development were examined. The relationship between absorbance and concentration of I, II, and III showed linear plots in the range of 0.6-2.5 μg/ml of I and II, and 6.25-25.0 μg/ml of III. Interference of water decreases the absorbance of aminopyrine-related compounds and indicated the necessity for removal of water. Thin-layer chromatography was applied for the detection of various aminopyrine-related compounds, using p-dimethylamino-cinnamaldehyde, and it was found possible to detect these compounds distinctly.
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MASAHIRO TAKAYA, TOSHIHIRO YAMADA, HIROSHI SHIMAMURA
1978 Volume 98 Issue 10 Pages
1421-1427
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Among seven metabolites which were isolated from the urine of man administered with 4-ethoxy-2-methyl-5-morpholino-3 (2H)-pyridazinone (M-73101), six metabolites were synthesized. Chemical structure of the synthesized samples was confirmed by instrumental analysis and direct comparison with the metabolites.
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MISAO KOJIMA, YOSHIAKI NAKANO
1978 Volume 98 Issue 10 Pages
1427-1431
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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A simple quantitative determination of ethanol content in 57 toiletries was attempted using gas chromatography in combination with head-space technique. The apparatus used was a gas chromatography equipped with hydrogen flame ionization detector (FID), and the column packing was PEG 20M/Chamelite CS. Samples used were eau de cologne, hair tonics, hair liquids, aftershave lotions, Iotions for women, milk lotions, and dentifrices. When propanol was used as an internal standard, ethanol content in both liquified and solidified samples was also capable of being calculated by the same equation. Results obtained by the head-space technique were close to the values determined by the use of a distillate in the dichromate oxidation method.
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YUKIO KAMEDA, SHOICHI KANATOMO, KATSUHIKO MATSUI, TOSHIKATSU NAKABAYAS ...
1978 Volume 98 Issue 10 Pages
1432-1435
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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For the test of cytolytic activity on Ehrlich ascites carcinoma cells, a new method, named the sheet method, was employed. By means of the sheet method, it was proved that the culture filtrate of Bacillus natto KMD 1126 had a cytolytic activity on Ehrlich ascites carcinoma cells. As a result of the analysis of the cytolytic activity, surfactin (I), protease (II), and an acidic substance (III) were separated from the culture filtrate. I, II, and III had no cytolytic activity but a mixture of I, II, and III showed a cytolytic activity, same as that of the culture filtrate.
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MADOKA SHIBATA, KYOKO KUBO, MAKOTO ONODA
1978 Volume 98 Issue 10 Pages
1436-1440
Published: October 25, 1978
Released on J-STAGE: May 30, 2008
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Pharmacological effect of water-soluble fraction (crude Folin) extracted from Sasa albomarginata MAKINO et SHIBATA (Bambusaceae) was examined in small animals. Crude Folin showed a prolonged hypotension and a decrease in heart rate in anesthetized rats. In the isolated frog heart and the isolated rat atrium, a negative inotropic effect was exhibited, and in the isolated rat aortic strip, a slight relaxation was observed by the crude fraction. Antagonistic effect was also observed against contraction induced by acetylcholine in the isolated rat fundus strip and against contraction induced by nicotine in the isolated guinea-pigileum. Further, crude Folin showed a slight depression of the pepsin activity in the rat gastric content.
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