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Volume 37, Issue 6
Displaying 1-50 of 63 articles from this issue
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Saburo SHIMABAYASHI, Kyouko ITOI1989 Volume 37 Issue 6 Pages 1437-1440
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe suspension pH at a given concentration of hydroxyapatite (HPA) decreased with the concentration of calcium chondroitin-6-sulfate (CaChs), whereas it increased with the concentration of sodium chondroitin-6-sulfate (Na2Chs). The former effect is due to the increase in the concentration of H+ by ion exchange between H+ on the surface of HAP and Ca2+ of CaChs, and the latter is due to the protonation of phoshate ion (Pi) released from the surface of HAP. The adsorbed amount of chondroitin-6-sulfate anion (Chs) by HAP was higher with CaChs than with Na2Chs over the concentration range examined. The equilibrium concentration of Pi decreased with increasing concentration of added CaChs because the concentration of free Ca2+, which dissociates from CaChs, regulated the free concentration of Pi through the restriction of the solubility product of HAP(Ksp). In contrast, than in the presence of Na2Chs increased with increasing concentration of added Na2Chs owing to the anion exchange between Chs and Pi of the HAP surface. The total concentration of Ca2+, which was released from HAP into the solution phase, increased after passing through a minimum with increasing concentration of added Na2Chs. That is, the concentration of Ca2+ free from Chs decreased with an increase in the concentration of released Pi owing to the restriction of the solubility product, whereas that of Ca2+ bound by Chs increased with increasing concentration of added Na2Chs through the ion exchange of Na+ with Ca2+. It was confirmed by the dialysis method that the value of Ksp was almost constant around 10-115, although HAP dissolves incongruently in the presence of Na2Chs.View full abstractDownload PDF (699K) -
Hitoshi TANAKA, Masaru HIROO, Kazuhiko ICHINO, Kazuo ITO1989 Volume 37 Issue 6 Pages 1441-1445
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe total synthesis of silychristin, an antihepatotoxic flavonolignan, is described. The key intermediate, the transdihydrobenzofuran (15) was synthesized as follows. Treatment of the chalcone epoxide (9) with boron trifluoride etherate and subsequent reduction with sodium borohydride gave exclusively the erythro-1, 2-diaryl-1, 3-propanediol (10). Hydrogenolysis of 10 with hydrogen over a palladium catalyst followed by cyclization of the debenzylation product (13) with boron trifluoride etherate in acetic acid afforded 15 as a single product.View full abstractDownload PDF (968K) -
Yasuyuki KITA, Fumio ITOH, Osamu TAMURA, Ya Yuan KE, Takashi MIKI, Yas ...1989 Volume 37 Issue 6 Pages 1446-1451
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Benzoyl-L-daunosamine was synthesized with high stereoselectivity utilizing a 1, 3-addition of ketene silyl acetal to the chiral nitrone, (Z)-[(4S, 5S)-2, 2, 5-trimethyl-1, 3-dixolan-4-yl]methylene[(1S)-1-phenylethyl]amine N-oxide, followed by a silyl group-transfer reaction in acetonitrile under mild conditions.View full abstractDownload PDF (1017K) -
Yasuhiro FUJIWARA, Motoshige SUMINO, Akira NOZAKI, Masao OKAMOTO1989 Volume 37 Issue 6 Pages 1452-1457
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photoreactions of 5H-dibenzo[a, d]cyclohepten-5-one (la) and its 5-substituted derivatives (lz and ly) with olefins such as maleates, acrylates and crotonate gave the cycloaddition products (3a-e) in yields of 4-82%. Inversion reactions of the adducts (3b and 3c) with bases were carried out for the purpose of investigating the thermodynamic stability of the cycloadducts and the corresponding isomeric products (3b-t and 3c-f) were obtained. The stereostructures of the cycloaddition products and the isomeric products were determined by means of nuclear magnetic resonance (NMR) spectroscopy.View full abstractDownload PDF (909K) -
Yasuhiro FUJIWARA, Masao OKAMOTO1989 Volume 37 Issue 6 Pages 1458-1464
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour stereoisomers of 3-methyloctahydroisocoumarins (4a-d)and two 1-methyloctahydro-3H-2-benzopyran-3-ones (10a, b) were synthesized. The stereochemical correlations including the configurations of the ring juncture and the methyl group and also the ring conformations of these six lactones were investigated by chemical means and by nuclear magnetic resonance (NMR) spectrometry, such as two-dimensional(2D) NMR and steady-state 1H-1H nuclear Overhauser effect experiments. It was concluded that the lactone ring of 4b, c, and 10a adopts a boat or a slightly distorted boat conformation in solution.View full abstractDownload PDF (1120K) -
Kaoru FUJI, Manabu NODE, Midori SAI, Eiichi FUJITA, Tetsuro SHINGU, Wi ...1989 Volume 37 Issue 6 Pages 1465-1469
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of five B-seco-kaurene type diterpenoids, trichorabdals A-E, isolated from Rabdosia trichocarpa were determined by chemical and physical means.View full abstractDownload PDF (870K) -
Manabu NODE, Midori SAI, Eiichi FUJITA, Kaoru FUJI1989 Volume 37 Issue 6 Pages 1470-1471
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of trichorabdals F and H, and trichorabdal G acetate isolated from Rabdosia trichocapa were determined. It is proposed from the results of structure elucidation of trichorabdal F that the structure of shikodonin should be revised.View full abstractDownload PDF (455K) -
Kaoru FUJI, Manabu NODE, Midori SAI, Eiichi FUJITA, Setsuo TAKEDA, Nor ...1989 Volume 37 Issue 6 Pages 1472-1476
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAmong the three types, enmein-, oridonin-, and trichorabdal-type, of diterpenoids from Rabdosia trichocarpa, the latter showed the highest antitumor activity against Ehrlich ascites carcinoma in mice. Their potent activities were attributed to synergistic increase arising from the presence of two active sites in one molecule. In vitro activity against HeLa cells and in vivo activity against P 388 lymphocytic leukemia of diterpenoids and related compounds were also determined, but no synergistic increase in activity due to plural active sites was observed in those cases.View full abstractDownload PDF (734K) -
Yasuo AKITA, Yohko ITAGAKI, Sayuri TAKIZAWA, Akihiro OHTA1989 Volume 37 Issue 6 Pages 1477-1480
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPalladium-catalyzed coupling reactions of 2-chloro-3, 6-dialkylpyrazines with 1-tosylindole gave 1-tosyl-3-(3, 6-dialkylpyrazin-2-yl)indoles as the main product in each case. The subsequent hydrolysis of the products yielded the corresponding 3(3, 6-dialkylpyrazin-2-yl)indoles under alkaline conditions. Coupling reactions of 2-chloro-3, 6-dialkyl-pyrazines with 1-methyl- or 1-benzylindole occurred at the 2-position of the indoles, but 2-chloro-3, 5-diphenylpyrazine (1e) failed to react with 1-methylindole.View full abstractDownload PDF (609K) -
Yusuke AMINO, Hirozumi ETO, Chikahiko EGUCHI1989 Volume 37 Issue 6 Pages 1481-1487
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(6-Carboxyhexyl)-5-[(E)-3-hydroxy-1-octenyl]midazole, an imidazole analogue of prostaglandin, was synthesized from 4(5)-hydroxymethylimidazole hydrochloride. The key step involves regioselective alkylation of 4(5)-tertbutyldimethylsilyloxymethylimidazole to give predominantly 1, 5-disubstituted imidazole.View full abstractDownload PDF (1098K) -
Hiromichi FUJIOKA, Hiroshi KONDO, Hirokazu ANNOURA, Hirofumi YAMAMOTO, ...1989 Volume 37 Issue 6 Pages 1488-1492
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNucleophilic addition of organometallic reagents (Grignard reagents and organolithium reagents) to two chiral 1-oxo-β-tetralone 1-acetals (1a, b) was studied. Extremely high stereoselectivity was achieved in the reactions of 1a and 1b with Grignard reagents leading to the α-hydroxy acetals (6) bearing a chiral tertiary alcohol moiety at the homobenzylic position. The stereochemistry of the products derived from 1a was determined by correlation with compound 9 and that of the products derived from 1b was determined by consideration of the citcular dichroism spectrum of the benzoate (11) prepared from 6bC.View full abstractDownload PDF (874K) -
Naoki SAITO, Nanko KAWAKAMI, Eri YAMADA, Akinori KUBO1989 Volume 37 Issue 6 Pages 1493-1499
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA mild and effecient method for the synthesis of 1, 2, 3, 4-tetrahydroisoquinolines 3a-c and 9 by a modified Pictet-Spengler reaction involving Lewis acid-mediated cyclization of the O, N-acetals 2a-c and 8 is described. The synthetic urility of this reaction is demonstrated with a preparation of two isoquinolinequinone antibiotics, renierone (11) and mimocin (12), from the ester 3c.View full abstractDownload PDF (1203K) -
Jean-Marie GAZENGEL, Jean-Charles LANCELOT, Sylvain RAULT, Max ROBBA1989 Volume 37 Issue 6 Pages 1500-1503
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of 6, 11-dihydro-5H-pyrimidino[4, 5-a]carbazoles (10) was achieved by cyclization of 1, 2, 3, 4-tetrahydrocarbazol-1-ones with triformamidomethene. The oxidation with potassium permenganate or mangenese bioxide of 6, 11-dihydro-5H-pyrimidino[4, 5-a]carbazoles gave the 11 H-pyrimidino[4, 5-a]carbazoles (11). The reactions of the pyrimidinocarbazole (11a) with organolithium compounds afforded 4-substituted derivatives (20, 21). The structure of the derivatives was determined by proton nuclear magnetic resonance.View full abstractDownload PDF (675K) -
Tozo FUJII, Taisuke ITAYA, Tohru SAITO, Kazuyo MOHRI, Mitsuru KAWANISH ...1989 Volume 37 Issue 6 Pages 1504-1513
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA detailed account is given of the general synthetic route to 3, 9-dialkyladenine salts (3d-I·HX) from N'-alkoxy-1-alkly-5-formamidoimidazole-4-carboxamidines (type 8 or 9), obtainable by ring opening of 1-alkoxy-9-alkyladenines (type 6 or 7). Alkylations of 8a and 9b, c with alkyl halides in HCONMe2 in the presence of NaH or anhydrous K2CO3 produced N'-alkoxy-1-alkyl-5-(N-alkylformamido)imidazole-4-carboxamidines (10d-f and 1lg-l) in good yields. Hydrogenolyses of 10d-f and 11g-l using hydrogen and Raney Ni catalyst in the presence of one molar eq of HCl afforded 1-alkyl-5-(N-alkylformamido)imidazole-4-carboxamidines (12d-l·HCl). On treatment with HCl, HClO4, or Et3N in boiling MeOH or EtOH, the amidines 12d-l·HCl cyclized to give 3, 9-dialkyladenines (3d-l), which were isolated as the HCl or HClO4 salts. 9-Alkyl-3-methyladenine salts (3d, g, j·HX) were alternatively synthesized from 8a and from 9b, c through a 3-step route, which consisted of LiAlH4 reduction of the formamido group, cyclizations of the resulting 5-(methylamino)imidazoles (15a and 16b, c) with CH(OEt)3 to give N6-alkoxy-9-alkyl-3-methyladenines (17a and 18b, c), and dealkoxylation of 17a and 18b, c by catalytic hydrogenolysis. 3, 9-Dialkyladenine salts (3d-l·HX) thusprepared were found to be unstable in alkaline aqueous solution. In 0.1 M aqueous NaHCO3, 3d·HCl and 3f·HClO4 were equilibrated with their ring-opened derivatives, 12d and 12f, respectively, and their equilibrium constants and rates of ring opening and cyclization at 25°C were determined.View full abstractDownload PDF (1836K) -
Yukie KITAMURA, Koh KANEKO, Motoo SHIRO, Yuh-Pan CHEN, Hong-yen HSU, P ...1989 Volume 37 Issue 6 Pages 1514-1516
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new D/E cis (20S, 22R, 25S)-20-deoxy-5α-cevanine alkaloid, tortifoline (1), was isolated from the Chinese herbal drug, "rakuri baimo"(dried bulbs of Fritillaria tortifolia). The structure of 1 was deduced from spectral data and its absolute configuration was confirmed by X-ray crystallographic analysis.View full abstractDownload PDF (548K) -
Minoru UCHIDA, Seiji MORITA, Masatoshi CHIHIRO, Toshimi KANBE, Katsuya ...1989 Volume 37 Issue 6 Pages 1517-1523
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMany 8-[(2-benzimidazolyl)sulfinyl]-5, 6, 7, 8-tetrahydroquinolines were synthesized and examined for their (H+ + K+) adenosine triphoshatase ATPase-inhibitory and antisecretory activities. These sulfinyl compounds could be considered to be rigid analogues of the 2-[(2-pyridyl)methylsulfinyl]benzimidazole class of antisecretoey agents. All the compounds tested were potent inhibitors of (H+ + K+)ATPase. Most of the compounds also inhibited histamine-induced gastric acid secretion in rats. Among them, 8-[(5-fluoro-2-benzimidazoly)sulfinyl]-3-methyl-5, 6, 7, 8-tetrahydroquinoline (XIVm) was found to have the most potent activity. The structure-activity relationships are discussed.View full abstractDownload PDF (980K) -
Kaoru SENO, Sanji HAGISHITA1989 Volume 37 Issue 6 Pages 1524-1533
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour stereoisomers of the title compounds based on side chain ring junctions, (+)-7a, (+)-7b, (-)-7c and (-)-24, were synthesized from (-)-myrtenol and (+)-nopinone. The (1R, 2R, 3S, 5S)-isomer (+)-7b had the most potent inhibitory activity against platelet aggregation and did not show partial agonist activity (shape change of platelets). We also synthesized the antipode, (-)-7b, and derivatives of (+)-7b with various kinds of substituents at the sulfonylamino group, 34a-n and p. The one-carbon homologated compound, (+)-58, was also prepared. The inhibitory activities of these compounds against platelet aggregation were measured.View full abstractDownload PDF (1634K) -
Morihiro MITSUKUCHI, Jozi NAKAGAMI, Tomoyuki IKEMOTO, Shohei HIGUCHI, ...1989 Volume 37 Issue 6 Pages 1534-1539
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 17-succinyl derivatives of four corticosteroids was prepared. They were tested for vasoconstrictive activity in humans, using 9α-fluoro-11β, 21-dihydroxy-16β-methyl-17α-valeryloxy-1, 4-pregnediene-3, 20-dione (betamethasone 17-valerate, BV) as a standard. The activities of the 21-chloro 17-methylsuccinate compounds (6A, 6C and 6D) were greater than that of BV. A structure-activity relationship study showed that the activities of the 21-chloro 17-methylsuccinates were more potent than those of the corresponding 21-esters.View full abstractDownload PDF (937K) -
Yuko NAGATSU, Makoto INOUE, Yukio OGIHARA1989 Volume 37 Issue 6 Pages 1540-1542
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of Shosaikoto, one of the Kampo medicines, on macrophage functions were studied in mice. Oral administration of Shosaikoto (1.2 g/kg of body weight) increased the change of the membrane fluidity of macrophages and diminished prostaglandin E2 production. Moreover, macrophages from mice orally given Shosaikoto phagocytized antigen more efficiently than control macrophages, resulting in presentation of much more antigen to lymphocytes. These results suggest that Shosaikoto enhances the immune response through at least two different routes, that is, through eliminating the inhibition of lymphocyte functions by prostaglandin E2 and through presenting antigen more efficiently.View full abstractDownload PDF (585K) -
Takehiko FUKUNAGA, Koichi NISHIYA, Ikuko KAJIKAWA, Koichi TAKEYA, Hide ...1989 Volume 37 Issue 6 Pages 1543-1546
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical constituents of Japanese mistletoes, Taxillus yadoriki DANSER, Taxillus kaempferi DANSER, and Korthalsella japonica ENGLER, epiphyting to different host trees were compared, and the antimicrobial and hypotensive properties of some isolated flavonoids were examined. Two known flavonoid glycosides, hyperin and quercitrin, were isolated from Taxillus yadoriki DANSER, together with fatty acids, phytosterol, and phytosterol-glucoside. There was remarkable variation of contents of quercitrin among the plants on different host trees. From Taxillus kaempferi DANSER, fatty acids, phytosterol, phytosterol-glucoside, quercetin, avicularin, and taxillusin were isolated, and quercitrin and hyperin were also identified. These was no remarkable variation of compositions of flavonoid glycosides among the plants on different host trees. A known flavone glycoside, chrysoeriol-4'-O-glucoside, was isolated from Korthalsella japonica ENGLER, together with fatty acids, phytosterol, oleanolic acid, and phytosterol-glucoside. Chrysoeriol-4'-O-glucoside is contained in this plant irrespective of the host trees.View full abstractDownload PDF (729K) -
Mohan B. GEWALI, Masao HATTORI, Yasuhiro TEZUKA, Tohru KIKUCHI, Tsuneo ...1989 Volume 37 Issue 6 Pages 1547-1549
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the latex of Euphorbia antiquorum L. (Euphorbiaceae), four macrocyclic diterpenes, 3, 12-di-O-acetyl-8-O-benzoylingol (1), 3, 12-di-O-acetly-8-O-tigloylingol (2), 12-O-acetyl-8-O-tigloylingol (3) and 8-O-tigloylingol (4), were isolated and characterized. Compound 1 was previously reported as a component of a mixture, but was obtained in pure form in this experiment. Compounds 3 and 4 were isolated for the first time from a natural source.View full abstractDownload PDF (505K) -
Takao KONOSHIMA, Mutsuo KOZUKA, Mitsumasa HARUNA, Kazuo ITO, Takeatsu ...1989 Volume 37 Issue 6 Pages 1550-1553
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new triterpenoids (wistariasapogenols A and B) were obrained from the knots of Wistaria brachybotrys (Leguminosae), and characterized as 22-oxo-3β, 24, 30-trihydroxyolean-12-ene (1) and 3β, 22β, 24, 30-tetrahydroxyolean-12-ene (8) by analysis of the two-dimensional nuclear magnetic resonance spectra (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and 1H-13C long-range COSY) and the difference nuclear Overhauser effect spectra.View full abstractDownload PDF (697K) -
Yoshio SASAKI, Shiho FUJII, Tatsuya TAKAGI, Hideko KAWAKI1989 Volume 37 Issue 6 Pages 1554-1555
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe separation coefficients (log γ) of halogenobenzene derivatives obtained by means of gas-liquid chromatography have been subjected to the regression analysis, using the novel quantitative structure-activity relationship (QSAR) descriptor σS°, together with the sum of Swain-Lupton's resonance parameter ΣR. The result indicated that the former is the major determinant, whereas the latter is minor. From the above result, the successful estimation of unknown values of σS° has been achieved for polyhalogenobenzene derivatives. Furthermore, the values of S°298(g) agree well with observed values determined by statistical thermodynamics.View full abstractDownload PDF (421K) -
Tatsuya TAKAGI, Yoko SHINDO, Hideaki FUJIWARA, Yoshio SASAKI1989 Volume 37 Issue 6 Pages 1556-1560
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFactor analyses have been carried out for the gas-chromatographic retention data on 21 stationary phases and 190 solutes using the techniques of the principal factor analysis and the oblique procrastes transformations. The eigenvalues showed the necessity of three factors to explain fully the variations of the retention volumes. Further analyses by using the factor scores after the oblique procrastes transformations have disclosed the meanings of the three factors. Namely, the first factor reflects the dispersion interactions and the formation of cavities in the stationary phase, the second one reflects the polar interactions, and the third one reflects the hydrogen-bonding interactions.View full abstractDownload PDF (773K) -
Mitsuteru NUMAZAWA, Katsuhiko KIMURA, Masao NAGAOKA, Akira KAMBEGAWA1989 Volume 37 Issue 6 Pages 1561-1563
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntigenic complexes of 2-hydroxyestrone (2-OHE1) were obtained by Mannich reaction of 2-OHE1 and bovine serum albumin (BSA) and by coupling of 2-OHE1 1-glutathione thioether to BSA using glutaraldehyde. Antiserum raised against the antigen obtained by the Mannich reaction had high affinity (Kd=3.8×109M-1) and relatively high specificity; cross reactivities for estrone, 4-hydroxyestrone and 2-methoxyestrone were 2.1%, 10% and 1.5%, respectively. The other antiserum also had high affinity (4.5×109M-1) but its cross reactivities for the above three steroids were more than 100%. Concentrations of 2-hydroxyestrone in human plasma were determined by radioimmunoassay with the more specific antiserum and Sephadex LH-20 chromatography to be lless than a minimum detectable amount (<10 pg/ml) (men), 20.9 pg/ml (women, proliferation) and 26.0 pg/ml (women, periovulation).View full abstractDownload PDF (523K) -
Kazuo ISHII, Haruo OKAJIMA, Youji OKADA, Hirokazu KONISHI, Hiroshi WAT ...1989 Volume 37 Issue 6 Pages 1564-1567
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe lipids of the crayfish muscle, composed simply of phospholipids (78%) and free sterols (20%), were analyzed precisely, since furan fatty acids (F acids) had previously been found in the neutral lipids from hepatopancreas of the animal. The analysis yielded the following findings. (i) The main phospholipids were choline phosphoglycerides (CPG, 40.3%) and ethanolamine phosphoglycerides (EPG, 16.6%). (ii) The fatty acid analysis of EPG and CPG (mixtures of diacyl and ether-containing phosphoglycerides) showed that the predominant acyl chains at the sn-1 position were 18 : 1 in EPG and 16 : 0 in CPG, and that acyl chains at the sn-2 position were rich in polyunsaturated fatty chains. (iii) F acids were detected at the sn-2 position of EPG. The profile of F acids in the total phospolipid fraction was the same as that in the case of the hepatopancreas. (iv) EPG and CPG contained significant amounts of ether-containing phosphoglycerides (40% and 45%, respectively). (v) In the ether-containing phosphoglycerides, 1-O-alkenyl and 1-O-alkyl chains were composed of saturated, monounsaturated, and branched chains. Acyl chains at the sn-2 position consisted of polyunsaturated chains for the most part and of phytanic chains in a small amount.View full abstractDownload PDF (597K) -
Takako YOKOZAWA, Hae Young CHUNG, Tae Woong LEE, Hikokichi OURA, Takas ...1989 Volume 37 Issue 6 Pages 1568-1571
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe involvement of prostanoids in the improvement of adenine-induced renal failure in rats by magnesium lithospermate B was studied. After intraperitoneal administration of magnesium lithospermate B to renal failure rats, the levels of glomerular filtration rate, renal plasma flow and renal blood flow were increased. Urinary excretions of prostaglandin E2 (PGE2) and 6-keto-prostaglandin F1α (6-keto-PGF1α) in renal failure rats were increased by the administration of magnesium lithospermate B, while that of thromboxane B2 had no effect. Pretreatment with indomethacin abolished the improving effect of magnesium lithospermate B on renal function concomitantly with markedly suppressed urinary excretion of prostanoids. These results suggest that the increased formation of PGE2 and 6-keto-PGF1α might contribute to the improvement of adenine-induced renal failure in rats by magnesium lithospermate B.View full abstractDownload PDF (697K) -
Shiro WATANABE, Erika SUZUKI, Noriyuki KOJIMA, Ryoji KOJIMA, Yoshio SU ...1989 Volume 37 Issue 6 Pages 1572-1575
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMale Sprague-Dawley rats at 3 weeks of age were weaned to a diet supplemented either with perilla seed oil [α-linolenic acid (α-LnA)/linoleic acid (LA)=3.66] or with safflower seed oil (α-LnA/LA<0.01) for 5-6 weeks. The eicosapentaenoic acid (EPA)/arachidonic acid (AA) ratio in platelet phospholipids was much higher in the perilla oil group than in the safflower oil group. Platelet aggregability determined turbidometrically varied greatly among individual animals, and the difference in platelet aggregability between the two dietary groups was relatively small when higher concentrations (15 and 20 μg/ml) of collagen were used. However, when platelet aggregability was determined as an all-or-none phenomenon at lower concentrations (7.5 and 10 μg/ml) of collagen, a very distinct difference was observed between the two dietary groups; aggregability was much lower in the perilla oil group than in the safflower oil group. Collagen-induced serotonin release from platelets was significantly reduced in the perilla oil group as compared with the safflower oil group. These results emphasize the importance of estimating aggregability at threshold concentrations of collagen and confirm that dietary manipulation of the essential fatty acid balance could be useful in reducing the thrombotic tendency.View full abstractDownload PDF (719K) -
Takashi TOBE, Kaori MURAKAMI, Motowo TOMITA, Ryushi NOZAWA1989 Volume 37 Issue 6 Pages 1576-1580
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA differentiation antigen 60B8 appeared in human promyelocytic leukemia HL-60 cells which had been induced to differentiate into macrophage-like cells by treatment with 1, 25-dihydroxyvitamin D3. The antigen was purified by immunoaffinity chromatography and separated into two proteins, 60B8-A and -B antigens, by reverse-phase high performance liquid chromatography (HPLC). Both proteins were digested with proteases, and the resulting peptides were subjected to amino acid sequence analysis after purification by reverse-phase HPLC. The amino acid sequences of 60B8-A and -B antigens were identical with those of the proteins MRP-14 and -8, respectively, which were recently predicted from the nucleotide sequences of their complementary deoxyribonucleic acid (cDNA) clones by Odink et al. (Nature (London), 330, 80 (1987)). Although they did not characterize the chemical properties of the two proteins, our results clearly indicate that macrophage-related protein (MRP)-14 and -8 are expressed without post-translational modification, except that the amino-terminus of MRP-14 is blocked, in differentiated HL-60 cells.View full abstractDownload PDF (748K) -
Ichitomo MIWA, Motoya KANBARA, Jun OKUDA1989 Volume 37 Issue 6 Pages 1581-1582
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sciatic motor nerve conduction velocity of mutant diabetic C57BL/Ks mice was significantly improved from 30.0±1.4 to 38.0±4.6m/s by treatment with the aldose reductase inhibitor 1-[(β-naphthyl)sulfonyl]hydantoin (30 mg/kg/d) for 2 weeks. The treatment, however, did not cause any significant change in myo-inositol concentration in the sciatic nerve. The results indicate that the ameliorating effect of the aldose reductase inhibitor no nerve conduction velocity in mutant diabetic mice is not due to alteration of myo-inositol content in the nerve.View full abstractDownload PDF (483K) -
Hironori TAKANASHI, Hiroshi HOMMA, Michio MATSUI1989 Volume 37 Issue 6 Pages 1583-1586
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA rapid method for the separation and purification of uridine diphosphate-glucuronosyltransferases (GT) was developed with the use of chromatofocusing on a high-performance liquid chromatograph. GT isoenzymes solubilized from hepatic microsomes of Wistar rats were separated on a Mono P column, a pre-packed column for chromatofocusing. Using 4-nitrophenol, testosterone and androsterone as substrates, four fractions with different GT activities were separated in a pH gradient from 9.5 to 7.0. Two isoenzymes, testosterone GT and androsterone GT were purified to apparent homogeneity. They were eluted at pH 8.9 and 8.0 and had subunit molecular weight values of 50000 and 52000, respectively. Approximately 10 mg of solubilized microsomal proteins was applied and the elution was completed within 2h. Addition of N-nitrodiethylamine, an in vitro activator of GT activity, enhanced the GT activity toward 4-nitrophenol in the three fractions. This chromatographic analysis confirmed the absence of androsterone GT isoenzyme in LA Wistar rats, a mutant strain in terms of androsterone glucuronidation.View full abstractDownload PDF (723K) -
Pimolpan PITHAYANUKUL, Hiraku ONISHI, Tsuneji NAGAI1989 Volume 37 Issue 6 Pages 1587-1590
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN4-(4-Carboxybutyryl)-1-β-D-arabinofuranosylcytosine (glu-ara-C), the conjugate of glu-ara-C and poly-L-lysine (PLL), (PLL-glu-ara-C), and the conjugate of glu-ara-C and decylenediamine-dextran T70 (T70-C10), (T70-C10-glu-ara-C), were prepared. Drug regeneration from glu-ara-C and the conjugates was investigated in buffered solutions of pH 4, 5, 7, 7.4 and 8. The character of the drug release from the conjugates was different from that from glu-ara-C. Namely, the release of 1-β-D-arabinofuranosylcytosine (ara-C) from glu-ara-C was accelerated under both weakly acidic and weakly basic conditions, while it was acclerated only under weakly basic conditions from the conjugates. Overall, the drug release profiles from the conjugates showed similar patterns. However, under neutral and weakly basic conditions, ara-C was regenerated more rapidly from PLL-glu-ara-C than from T70-C10-glu-ara-C. During the incubation of glu-ara-C and the conjugates under weakly acidic conditions, 1-β-D-arabinofuranosyluracil (ara-U) was detected and its amount increased with time to similar extents.View full abstractDownload PDF (624K) -
Daisuke TESHIMA, Kenji OTSUBO, Shun HIGUCHI, Fumitoshi HIRAYAMA, Kanet ...1989 Volume 37 Issue 6 Pages 1591-1594
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stabilizing effects of β-, γ- and 2, 6-dimethyl-β-cyclodextrins (β-, γ- and DM-β-CyDs) against photodegradation and thermal degradation of emetine (EM) and cephaeline (CP) in aqueous solution were examined. The degradation rates of EM and CP increased with decreasing pH below about 3 and with increasing pH above about 5, showing V-shaped pH-profiles, and the photodegradation of EM and CP was significantly faster than the thermal degradation. The photostability of EM and CP was improved by the complexation with γ- and DM-β-CyDs, while it was reduced slightly by β-CyD. The emetic syrup was prepared with γ-CyD or DM-β-CyD in pH 4 phosphate buffer colution, and its photostability was investigated. The results suggested that γ- and DM-β-CyD complexations are useful for the stabilization of EM and CP in the syrup preparation.View full abstractDownload PDF (574K) -
Keiichi ASAHARA, Hitoshi YAMADA, Shigeru YOSHIDA, Shingo HIROSE1989 Volume 37 Issue 6 Pages 1595-1599
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrolysis of gabexate mesilate (GM) in aqueous solution was found to be accelerated by sodium bisulfite (SBS). The hydrolysis in the presence of SBS was pseudo-first-order and the action of SBS was found to be catalytic. In the pH range of 5.0-7.5, the dominant degration process was considered to be a reaction between gabexate cation (G+) and sulfite ion. The rate constant for the catalytic hydrolysis of G+ with sulfite ion was 502.6 M-1 h-1 at 25°C and μ=0.5. The effects of temperature and concentration of SBS on the hydrolysis were evaluated. From these findings, we produced a nomograph to predict the stability of GM in the parenteral admixture containing SBS as an antioxidant.View full abstractDownload PDF (690K) -
Kiyomi KIKUGAWA, Teshuta KATO, Yasushi TAKEDA1989 Volume 37 Issue 6 Pages 1600-1603
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of an antihypotensive drug, etilefrin [α-{(ethylamino)methyl}-m-hydroxybenzyl alcohol], with nitrite under mildly acidic conditions produced N-nitrosoetilefrin [α-{(N-nitrosoethylamino)methyl}-m-hydroxybenzyl alcohol] (a mixture of syn and anti forms) (Iab) and diazo-N-nitrosoetilefrin [1-(4-diazo-3-oxo-1, 5-cyclohexadienyl-2-(N-nitrosoethylamino)ethanol] (a mixture of syn and anti forms) (IIab). Treatment of etilefrin with an equivalent amount of nitrite at pH 3 and 37°C for 4 h gave lab (yield, 30%) and IIab (yield, 5%). Treatment of eilefrin with 4 eq of nitrite under the same conditions gave Iab (23%) and IIab (53%). Compounds Iab IIab were each composed of two isomers due to the configuration of the N-nitroso group. While compound Iab was not mutagenic, compound IIab showed mutagenicity to Salmonella typhimurium TA98 and TA100 strains without metabolic activation. Specific mutagenic activity of IIab was 300 his+ revertant colonies for both TA98 and TA100 strains with a dose of 0.1μmol. Addition of a microsomal activation system little affected the activity. It is noteworthy that this orally administered drug can produce a direct-acting mutagen by reaction with nitrite, which is present in the digestive tract.View full abstractDownload PDF (708K) -
Yoshiko SATO, Tokumi MARUYAMA, Mikio HONJO1989 Volume 37 Issue 6 Pages 1604-1608
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTriflation of the N5-benzylidene-3', 5'-O-silyl protected 5-amino-4-cyano-1-(β-D-ribofuranosyl)imidazole (AICN-riboside) (IIb), followed by nucleophilic displacement with OAc- and N3-provided the corresponding 2'(S)-substituted derivatives (VIIa, VIIb). Deprotection of the silyl and benzylidene groups of VIIa, followed by hydrolysis of the acetyl group gave AICN-arabinoside (IXc). Reaction of IXc with alkyl, aryl and aralkyl nitriles afforded the corresponding 2-substituted adenine-arabinosides (XIa-e). The 2'-azido (Xa) and 2'-amino (Xb) analogs of XIa were similarly prepared.View full abstractDownload PDF (689K) -
Toshihisa OGAWA, Kazuyuki TOMISAWA, Kaoru SOTA1989 Volume 37 Issue 6 Pages 1609-1611
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe preparation of D-penicillamine (5) was achieved by a single-step reaction of benzylpenicillin potassium salt (1) with arylamines (2, 7, and 13). The intermediates in these reactions should be the penicilloic acid α-amides. The structures of by-products formed in these reactions were also determined.View full abstractDownload PDF (513K) -
Kenichi AKAJI, Yoshio HAYASHI, Nobutaka FUJII, Teh-yung LIU, Ira BERKO ...1989 Volume 37 Issue 6 Pages 1612-1615
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA glycine-linked tetramer of Asn-Ala-Asn-Pro, a tandem repeated sequence of malaria circumsporozoite (CS) protein, was synthesized by the Boc-based solid phase method, followed by deprotection with 1 M trimethylsilyl trifluotomethanesulfonate-thioanisole in trifluoroacetic acid. In addition, three tetramer-related peptides were similarly synthesized, i. e., a 34-residue peptide [linked with TH, a proposed T-cell epitope of CS, at the C-terminus of the tetramer], a 46-residue peptide and a 59-residue peptide [linked with HA or HA', two preposed T-cell epitopes of influenza hemagglutinin protein, at the N-terminus of the above 34-residue peptide]. Their immunological properties were examined by enzyme-linked immunosorbent assay, for which three different congenic strains of mouse were used to raise the specific antibodies. Despite conjugation of T-cell epitopes to the tetramer, the mice of low-responder strains to the tetramer failed to produce any antibody specific to the tetramer. However, with the aid of recombinant interleukin 2 as an adjuvant, the low-responder mice produced antibody with relatively high titers.View full abstractDownload PDF (638K) -
Hitoshi ISHIDA, Takayuki UMINO, Kuniro TSUJI, Takuo KOSUGE1989 Volume 37 Issue 6 Pages 1616-1618
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy following the antihemostatic activity of the material according to Tajima's method, the antihemostatic principle was isolated from dried buds of Sophora japonica L., and identified as isorhamnetin [2-(3-methoxy-4-hydroxyphenyl)-3, 5, 7-trihydroxy-4H-1-benzopyran-4-one]. The antihemostatic specificity of isorhametin toward antihemorrhagic compounds isolated previously from hemostatic herbs used in traditional Chinese medicine was examined.View full abstractDownload PDF (536K) -
Hideji ITOKAWA, Nobuo TOTSUKA, Keisuke NAKAHARA, Manaby MAEZURU, Koich ...1989 Volume 37 Issue 6 Pages 1619-1621
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of obtaining compounds with strong antitumor activity, a quantitative structure-activity relationship (QSAR) of antitumor phenolic compounds (long-chain phenols) was derived using the Hansch-Fujita equation. The ED50 values against Chinese hamster V-79 cells were analyzed in terms of log P as the hydrophobic parameter and the energy of the lowest unoccupied molecular orbital (ELUMO) calculated by using the modified neglect of differential overlap (MNDO) method as the electronic parameter, by means of multiple regression analysis. It was found that the activities mainly depended on log P (an optimum log P of 8.3) and a low-lying ELUMO value. 4-Undecylcatechol, selected on the basis of the above results, exhibited strong antitumor activity against Sarcoma 180 ascites and P-388 lymphocytic leukemia.View full abstractDownload PDF (547K) -
Fathalla BELAL, Mitsuaki SANO, Isao TOMITA1989 Volume 37 Issue 6 Pages 1622-1623
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn ion-pairing high-performance liquid chromatographic method was developed for the determination of yohimibine and strychnine in dosage forms. The mobile phase consists of methanol-water-acetic acid-triethylamine (50 : 50 : 1 : 0.3) with 1 mM sodium hexanesulfonate as the counter-ion. The analysis was carried out using an octadecyl silica (5 μm, 100 mm × 6 mm i.d.) column. Detection was done spectrophotometrically at 254 nm. Calibration graphs were rectilinear over the concentration ranges of 2-20 μg/ml for strychine sulfate and 5-50 μg/ml for yohimbine HCl, with minimum detection limits of 0.1 and 0.4 μg/ml, respectively. For the determination of yohimbine alone, high performance liquid chromatography/fluorometric analysis (Ex270, Em<360>nm) was carried out with the same mobile phase. THe calibration graph was rectilinear over the concentration range of 5-40 ng/ml with a minimum detection limit of 2 ng/ml. The proposed methods were applied to dosage forms containing yohimibine and/or a mixture of yohimbine and strychine. The results obtained compared favorably with those found with alternative methods.View full abstractDownload PDF (434K) -
Naoki MITSUO, Nobuko NAKAYAMA, Hitoshi MATSUMOTO, Toshio SATOH1989 Volume 37 Issue 6 Pages 1624-1626
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSimple and rapid identification of monosaccharids by gas chromatography was achieved by the application of Curie-point pyrolysis. Almost all monosaccharides were distinguishable under pyrolysis conditions of 358°C for 3s. Each suger group, e.g. aldohexoses, aldopentoses, deoxysugars, uronic acids, sugar alcohols, and aminosugars, showed a characteristic pyrogram.View full abstractDownload PDF (461K) -
Hidenao TOYODA, SHigeyuki YAMANASHI, Yoshimi HAKAMADA, Kazufusa SHINOM ...1989 Volume 37 Issue 6 Pages 1627-1628
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA highly sensitive high-performance liquid chromatographic method wiht fluorometric postcolumn labeling using 2-cyanoacetamide was developed for the profile analysis of chondroitin sulfates (ChS) in normal human urine and serum. Over-sulfated disaccharide units such as di- or trisulfated unsaturated disaccharides in urine were estimated and unsaturated 6-sulfated disaccharide (ΔDi-6S) was found as a major component from ChS in urine, although only small amounts of ΔDi-6S from ChS were present in serum.View full abstractDownload PDF (467K) -
Tohru NAKAMURA, Shoichiro HOSHINO, Norio HAZEMOTO, Makoto HAGA, Yuriko ...1989 Volume 37 Issue 6 Pages 1629-1631
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new, sensitive immunoassay involving the combination of a liposome immunoassay with chemilluminescence detection is reported. Lysis of the liposomes with cytolysin-hapten conjugates released entrapped glucose oxidase. Chemiluminescence produced by reaction of the enzymatically formed hydrogen peroxide and isoluminol was monitored via an optical fiber and photomultiplier. Without a bound/free separation procedure, this chemical amplification of the immune reaction by liposome lysis and enzymatic reaction allowed detection of 1.7 ng/assay tube of digoxin, the model analyte. When liposome-coated microplates were used to separate intact liposomes from released enzyme, the sensitivity of detection was improved to 165 pg/assay tube.View full abstractDownload PDF (626K) -
Yoshihisa IWAMOTO, Chikayo TOMINAGA, Yasutake YANAGIHARA1989 Volume 37 Issue 6 Pages 1632-1634
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotodynamic cell-inactivating activities of food additive dyes on the yeast Saccharomyces cerevisiae were investigated. Activities of dyes not permitted as fod additives were also examined. Red No.105 (rose bengal), Red No.3 (erythrosine) and Red No.104 (phloxine), which are permitted as food additives, markedly inactivated yeast cells by photodynamic action Eosine, matius yellow and guinia green B, which are not permitted, also exhibited moderate cell-inactivating activity by photodynamic action. None of the dyes used in this experiment exhibited petite induction by photodynamic action.View full abstractDownload PDF (488K) -
Fumiaki ISHIDA, Akiko SATO, Yuri IIZUKA, Toshio KAMEI1989 Volume 37 Issue 6 Pages 1635-1636
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRelatively high concentrations of MK-733 (simvastatin) and MK-803 (lovastatin, mevinolin), which are 3-hydroxy-3-methylglutary coenzyme A (HMG-CoA) reductase inhibitors, were found to inhibit acyl coenyme A : cholesterol acyltransferase (ACAT) of rabbit intestial microsomes with IC50's of 2.0 × 10-5 and 3.6 ×10-5M, respectively. Dihydroxy acid forms of both MK-733 and MK-803 did not inhibit ACAT activity. A kinetic analysis using a Lineweaver-Burk plot indicated that MK-733 is a competitive inhibitor of ACAT, with a Ki value of 1.2 ×10-5M.View full abstractDownload PDF (430K) -
Yoko MATSUKI, Yoshimitsu KATAKUSE, Masataka KATASHIMA, Hiroshi MATSUUR ...1989 Volume 37 Issue 6 Pages 1637-1638
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method was established for preparation of deuterated isoniazid(2H-INAH). In this method isonicotinic acid N-oxide was deuterated by base-catalyzed exchange reaction and converted to 2H-INAH. The deuterium content of the 2H-INAH obtained by this method was 95.2 atom%D. This 2H-INAH is suitable for use as an internal standard in gas chromatography-mass spectrometry.View full abstractDownload PDF (402K) -
Yasuo UEDA, Koji MUNECHIKA, Akihito KIKUKAWA, Yoshiaki KANOH, Kouichi ...1989 Volume 37 Issue 6 Pages 1639-1641
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdriamycin linked to oxidized dextran (ADM-OXD) via Schiff's base formation was compared wiht free adriamycin with regard to antiumor activity, acute toxicity and plasma pharmacokinetics in rats following i.v. administration. ADM-OXD showed higher activity against Walker carcinosarcoma 256 than free adriamycin. On the other hand, the acute toxicity of ADM-OXD was about three times less than that of free adriamycin. In contrast to free adriamycin, a very high plasma level of adriamycin was found after i.v. administration of ADM-OXD. The area under the plasma concentration curve with ADM-OXD was about 160-fold higher than with free adriamycin. Thus, the improvement fo the therapeutic index in the case of ADM-OXD might be due to the difference in the disposition of ADM-OXD and free adriamycin in rats.View full abstractDownload PDF (506K) -
Kimiko SATOH, Kozo TAKAYAMA, Yoshiharu MACHIDA, Yoshiki SUZUKI, Tsunej ...1989 Volume 37 Issue 6 Pages 1642-1644
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe disintegration and dissolution characteristics of tablets consisting of hydroxypropyl cellulose (HPC) and carboxyvinyl polymer (CP), were studied, considering the interpolymer complex formation between HPC and CP in the tablet. Brilliant blue FCF (BBL) was used as a model compound of a water-soluble drug. A rapid disintegration was observed when the tablet was prepared with the HPC-CP solid complex. In the case of hte physical mixture of HPC and CP, the tablet maintained its original shape during the disintegration test (0-24h). The slowest dissolution of BBL was ovserved in water when the tablet was prepared with the sphysical imxture, and approximately 30% of BBL remained in the solid form in the tablet at 24 h. Althrough the dissolution of BBL from the tablet prepared with the physical mixture was affected by the pH value of the dissolution medium, other factors, such as the stirring rate of the dissolution medium and hte compression pressure of tablet, did not affect the dissolution of BBL from the tablet.View full abstractDownload PDF (1008K) -
Takefumi MOMOSE, Osamu MURAOKA, Kikuo MASUDA1989 Volume 37 Issue 6 Pages 1645-1646
Published: June 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe diazomethane-conducted ring expansion of bicyclo[3.3.1]nonane-2, 6-dione (1) was re-examined, and the main product, identified previously as 9-hydroxytricyclo[4.4.0.02, 9]decan-5-one (2), was shown to be 7-hydroxyisotwistan-2-one (6). The ring expansion of bicyclo[3.3.1]nonan-2-one (4) was also re-examined and the ratio of the resulting homologous ketones 10 and 11 was revised to ca. 5 : 1.View full abstractDownload PDF (508K)