Sanae Iwana, Tomoya Kawazoe, Hwan Ki Park, Koichiro Tsuchiya, Koji Ono, Kazuko YORITA, Takashi Sakai, Takenori Kusumi and Kiyoshi Fukui : Chlorpromazine oligomer is a potentially active substance that inhibits human D-amino acid oxidase, product of a susceptibility gene for schizophrenia, Journal of Enzyme Inhibition and Medicinal Chemistry, Vol.23, No.6, 901-911, 2008.
(Summary)
D-amino acid oxidase (DAO), a potential risk factor for schizophrenia, has been proposed to be involved in the decreased glutamatergic neurotransmission in schizophrenia. Here we show the inhibitory effect of an antipsychotic drug, chlorpromazine, on human DAO, which is consistent with previous reports using porcine DAO, although human DAO was inhibited to a lesser degree (K(i) = 0.7 mM) than porcine DAO. Since chlorpromazine is known to induce phototoxic or photoallergic reactions and also to be transformed into various metabolites, we examined the effects of white light-irradiated chlorpromazine on the enzymatic activity. Analytical methods including high-resolution mass spectrometry revealed that irradiation triggered the oligomerization of chlorpromazine molecules. The oligomerized chlorpromazine showed a mixed type inhibition with inhibition constants of low micromolar range, indicative of enhanced inhibition. Taken together, these results suggest that oligomerized chlorpromazine could act as an active substance that might contribute to the therapeutic effects of this drug.
Ko Yasumoto, Akinori Nishigami, Fumie Kasai, Takenori Kusumi and Takashi Ooi : Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton, Chemical & Pharmaceutical Bulletin, Vol.54, No.2, 271-274, 2006.
(Summary)
2,6-Dimethylheptyl sulfate (1) and 6-methyloctyl sulfate (3) were isolated from Daphnia pulex as the Daphnia kairomones that induced morphological defense of a freshwater phytoplankton Scenedesmus gutwinskii var. heterospina (NIES-802). The absolute stereochemistry at C2 of 1 was determined by (1)H-NMR analysis of the (R)-MTPA ester of alcohol 2. The absolute configuration at C6 of 3 was determined by Ohrui's method applied to alcohol 4.
(Keyword)
Alkanesulfonic Acids / Animals / Daphnia / Heptanes / Indicators and Reagents / Magnetic Resonance Spectroscopy / Molecular Conformation / Scenedesmus / Spectrometry, Mass, Fast Atom Bombardment / Stereoisomerism / Sulfates / Sulfuric Acid Esters
Ko Yasumoto, Akinori Nishigami, Mina Yasumoto, Fumie Kasai, Yasuhiro Okada, Takenori Kusumi and Takashi Ooi : Aliphatic sulfates released from Daphnia induce morphological defense of phytoplankton: isolation and synthesis of kairomones, Tetrahedron Letters, Vol.46, No.28, 4765-4767, 2005.
Toshimasa Ochi, Hirofumi Shibata, Tomihiko Higuti, Ko-hei Kodama, Takenori Kusumi and Yoshihisa Takaishi : Anti-Helicobacter pylori Compounds from Santalum album, Journal of Natural Products, Vol.68, No.6, 819-824, 2005.
(Summary)
Six new sesquiterpenes, (Z)-2beta-hydroxy-14-hydro-beta-santalol (1), (Z)-2alpha-hydroxy-albumol (2), 2R-(Z)-campherene-2,13-diol (3), (Z)-campherene-2beta,13-diol (4), (Z)-7-hydroxynuciferol (5), and (Z)-1beta-hydroxy-2-hydrolanceol (6), together with five known compounds, (Z)-alpha-santalol (7), (Z)-beta-santalol (8), (Z)-lanceol (9), alpha-santaldiol (10), and beta-santaldiol (11), were isolated from Santalum album, by using bioassay-guided fractionation for Helicobacter pylori. The structures were determined by extensive NMR studies. The absolute configuration of compound 3 was determined by a modified Mosher method. The crude extracts as well as the isolated compounds showed antibacterial activity against H. pylori. Especially, compounds 7 and 8 have strong anti-H. pylori activities against a clarithromycin-resistant strain (TS281) as well as other strains.
Kaori Iba, Shu-ichi Fukuyoshi and Takenori Kusumi : 9.4 T and 7.05 T Magnetic Fields Accelerate a Radical Oxidation Reaction with a Hypervalent (tert-Butylperoxy)iodane, Chemistry Letters, Vol.33, No.6, 716-717, 2004.
Takahiro Kawai, Ko-hei Kodama, Takashi Ooi and Takenori Kusumi : 1,3-Dipolar addition of nitrones to symmetrically substituted allenes: for the determination of absolute configuration of chiral allenes by NMR spectroscopy, Tetrahedron Letters, Vol.45, No.21, 4097-4099, 2004.
Kanami Mori, Takashi Ooi, Masanori Hiraoka, Naohiro Oka, Hideyuki Hamada, Mitsumasa Tamura and Takenori Kusumi : Fucoxanthin and Its Metavolites in Edible Brown Algae Cultivated in Deep Seawater., Marine Drugs, Vol.2, No.2, 63-72, 2004.
8.
Kanami Mori, Takashi Ooi, Masanori Hiraoka, Naohiro Oka, Hideyuki Hamada, Mitsumasa Tamura and Takenori Kusumi : Fucoxanthin and Its Metabolites in Edible Brown Algae Cultivated in Deep Seawater, Marine Drugs, Vol.2, 63-72, 2004.
(Keyword)
fucoxanthin / deep seawater / brown algae / Scytosiphon lomentaria / Undaria pinnatifida / Petalonia binghamiae / Laminaria religiosa
9.
Kanami Mori, Takashi Ooi, Masanori Hiraoka, Naohiro Oka, Hideyuki Hamada, Mitsumasa Tamura and Takenori Kusumi : Fucoxanthin and Its Metabolites in Edible Brown Algae Cultivated in Deep Seawater, Marine Drugs, Vol.2, 63-72, 2004.
(Keyword)
fucoxanthin / deep seawater / brown algae / Scytosiphon lomentaria / Undaria pinnatifida / Petalonia binghamiae / Laminaria religiosa
10.
Mami Azuma, Hitoshi Houchi, Hirotaka Nishisako, Keisuke Ishizawa, Koichiro Tsuchiya, Kazuhiko Teraoka, Toshitaka Ikehara, Takenori Kusumi and Kazuo Minakuchi : Inhibitory action of novel arginine derivative on catecholamine secretion evoked by acetylcholine from cultured bovine adrenal chromaffin cells, Journal of Cardiovascular Pharmacology, Vol.42, No.Suppl. 1, S15-S18, 2003.
(Summary)
A novel product, 4-amino-5-guanidinopentanoic acid 15-[(4-aminobutyl)-3-aminopropylcarbamoyl] pentadecyl ester (Arg-HSA-Spm), was synthesized based on ptilomycalin A, which is one of the extracts from marine sponge. Arg-HSA-Spm contains arginine in its chemical structure. The pharmacological action of Arg-HSA-Spm on catecholamine secretion from cultured bovine adrenal chromaffin cells was examined. Arg-HSA-Spm inhibited catecholamine secretion stimulated by the physiological secretagog acetylcholine. This inhibitory action of Arg-HSA-Spm on catecholamine secretion induced by 10(-4) M acetylcholine was dose-dependent from 10(-8) M to 10(-5) M. In the presence of 3 x 10(-7) M Arg-HSA-Spm, the stimulation of catecholamine secretion observed by increasing acetylcholine up to 10(-3) M did not reach the maximal level observed without Arg-HSA-Spm. Arg-HSA-Spm at 10(-5) M suppressed both the increase in intracellular free Ca2+ level and the influx of 45Ca2+ induced by 10(-4) M acetylcholine. The Arg-HSA-Spm-induced suppression of intracellular free Ca2+ level, the influx of 45Ca2+ and catecholamine secretion were not observed in the presence of extracellular K+ at 56 mM. The results presented in this study suggested that Arg-HSA-Spm may inhibit the influx of extracellular Ca2+ into the cells, probably through its blocking action related to acetylcholine receptors, resulting in the inhibition of catecholamine secretion in adrenal chromaffin cells.
Shoko Arita, Tetsuya Yabuuchi and Takenori Kusumi : Resolution of 1- and 2-naphthylmethoxyacetic acids, NMR reagents for absolute configuration determination, by use of L-phenylalaninol, Chirality, Vol.15, No.7, 609-614, 2003.
(Summary)
Racemic 1- and 2-naphthylmethoxyacetic acids (1NMA and 2NMA), the chiral anisotropic reagents used for absolute configuration determination of chiral secondary alcohols and primary amines, were conveniently resolved to enantiomers (>99% ee) by condensation with L-phenylalaninol (2-amino-3-phenylpropanol), chromatographic separation of the diastereomers, and hydrolysis. This method enables large-scale preparation of enantiomeric 1NMA and 2NMA.
Kentaro Kogure, Satoru GOTO, Miki Nishimura, Mina Yasumoto, Kazutoyo Abe, Chie Ohiwa, Hironori Sassa, Takenori Kusumi and Hiroshi Terada : Mechanism of potent antiperoxidative effect of capsaicin, Biochimica et Biophysica Acta (BBA) - General Subjects, Vol.1573, No.1, 84-92, 2002.
(Summary)
The effect of a pungent ingredient of red pepper, capsaicin, on lipid peroxidation of rat liver mitochondria (RLM) induced by ADP/Fe(2+) was studied. Capsaicin inhibited the lipid peroxidation significantly, being more effective than the well-known antioxidant alpha-tocopherol. Capsaicin was also found to scavenge 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radicals both in solution and in membranes, especially the latter. Capsaicin was found to scavenge radicals both at/near the membrane surface and in the interior of the membrane. The phenolic OH-group of capsaicin remained intact after reaction with DPPH radicals, indicating that the hydroxyl group is not associated with the radical scavenging reaction. From the results of quantum chemical calculations of various radical intermediates derived from the model compound N-vanillylacetamide, and the findings that vanillin and 8-methyl-6-noneamide were major reaction products of capsaicin with DPPH radicals, it was concluded that the radical scavenging site of capsaicin is the C7-benzyl carbon.
Masahiro Inotani, Shuichi Fukuyoshi and Takenori Kusumi : Autoxidation of linoleic acid in a strong magnetic field (9.4 T), Tetrahedron Letters, Vol.42, No.42, 7451-7452, 2001.
(Keyword)
autoxidation / linoleic acid / unsaturated fatty acid / magnetic field autoxidation / linoleic acid / unsaturated fatty acid / magnetic field
Bao-Ning Su, Yoshihisa Takaishi, Tetsuya Yabuuchi, Takenori Kusumi, Motoo Tori, Shigeru Takaoka, Gisho Honda, Michiho Ito, Yoshio Takeda, Olimjon K. Kodzhimatov and Ozodbek Ashurmetov : Sesquiterpenes and Monoterpenes from the Bark of Inula macrophylla, Journal of Natural Products, Vol.64, No.4, 466-471, 2001.
(Summary)
Eleven new sesquiterpenes (1--11) and two thymol derivatives (12, 13), along with 12 known sesquiterpenes and monoterpenes, were isolated from the bark of Inula macrophylla. Their structures were determined on the basis of spectral evidence (especially by HREIMS and 2D NMR) as well as chemical transformations. The structure of macrophyllic acid A (1) was confirmed by X-ray analysis, and the absolute configuration of 1 was determined on the basis of the appropriate chemical conversions and the application of a modified Mosher's method.
Shu-ichi Fukuyoshi and Takenori Kusumi : Acceleration of Tributyltin Hydride Reduction of Phenethyl Iodide and m-Methoxybenzyl Bromide by a Strong Magnetic Field, Chemistry Letters, Vol.3, No.3, 230-231, 2001.
N Hanari, H Yamamoto, Takashi Ooi, Takenori Kusumi and K Kuroda : A New Diterpene Dimer from the Bark of Chamaecyparis obtusa, Journal of Wood Science, Vol.47, No.1, 36-40, 2001.
K Mada, Takashi Ooi and Takenori Kusumi : NMR Study of Acutanol, a New Cembrene Alcohol, and Sarcophytol A Isolated from the Soft coral Sarcophyton acutangulum, Spectroscopy: An International Journal, Vol.15, No.1, 177-182, 2001.
Mina Yasumoto, Keiko Mada, Takashi Ooi and Takenori Kusumi : New Terpenoid Components from the Volatile Oils of the Soft Corals Clavularia viridis and Sarcophyton acutangulum, Journal of Natural Products, Vol.63, No.11, 1534-1536, 2000.
(Summary)
A new tetracyclic terpenoid hydrocarbon, cyclosinularane (1), and (+)-alloaromadendrene (2), the enantiomer of terrestrial (-)-alloaromadendrene, have been isolated from the volatile oil of the soft corals Clavularia viridis and Sarcophyton acutangulum, respectively. Their structures have been determined on the basis of NMR spectral analysis and their chiroptical properties.
Shu-ichi Fukuyoshi, Takashi Ooi and Takenori Kusumi : Influence of the Conformation of Methoxy-(2-naphthyl)acetates (2NMA Esters) on Their Chemical Reactions, Chemical & Pharmaceutical Bulletin, Vol.48, No.8, 1208-1210, 2000.
(Summary)
An SN2 reaction (NaI) of 1,7-di(methanesulfoxyl)heptadien-4-yl methoxy-(2-naphthyl)acetate and a tributyltin hydride reduction of 1,7-diiodo-4-yl methoxy-(2-naphthyl)acetate (2NMA) is crucial for determination of the absolute configuration of secondary alcohols.
Bao-Ning Su, Yoshihisa Takaishi, Tetsuya Yabuuchi, Takenori Kusumi, Motoo Tori and Shigeru Takaoka : The structures and absolute configurations of macrophyllic acids A E, five new rearranged eudesmane sesquiterpene acids from the bark of Inula macrophylla, Tetrahedron Letters, Vol.41, No.14, 2395-2400, 2000.
(Keyword)
Inula macrophylla / compositae / macrophyllic acids A E / sesquiterpene acid / new carbon skeleton / NMR data / chemical transformation / X-ray analysis / absolute configuration / biosynthetic pathway
Tetsuya Yabuuchi and Takenori Kusumi : Phenylglycine Methyl Ester, a Useful Tool for Absolute Configuration Determination of Various Chiral Carboxylic Acids, The Journal of Organic Chemistry, Vol.65, No.2, 397-404, 2000.
(Summary)
A new chiral anisotropic reagent, phenylglycine methyl ester (PGME), developed for the elucidation of the absolute configuration of chiral alpha,alpha-disubstituted acetic acids, has turned out to be applicable to other substituted carboxylic acids, such as chiral alpha-hydroxy-, alpha-alkoxy-, and alpha-acyloxy-alpha, alpha-disubstituted acetic acids, as well as to chiral beta, beta-disubstituted propionic acids. Because a carboxylic moiety is convertible from other functional groups, e.g., ozonolysis of an olefin and oxidative cleavage of a glycol, the present findings can expand the utility of the PGME method to the absolute configuration determination of various types of organic compounds, even those which initially lack oxygen functions. Several examples of the combination of chemical reactions and the PGME method are described.
Bao-Ning Su, Yoshihisa Takaishi and Takenori Kusumi : Morinols A-L, twelve novel sesquineolignans and neolignans with a new carbon skeleton from morina chinensis, Tetrahedron, Vol.55, No.51, 14571-14586, 1999.
Tetsuya Yabuuchi and Takenori Kusumi : NMR Spectroscopic Determination of the Absolute Configuration of Chiral Sulfoxides via N-(Methoxyphenylacetyl)sulfoximines, Journal of the American Chemical Society, Vol.121, No.45, 10646-10647, 1999.
Masahiko Toki, Takashi Ooi and Takenori Kusumi : Sesterterpenoids and Diterpenoids of the Wax Excreted by a Scale Insect, Ceroplastes pseudoceriferus, Journal of Natural Products, Vol.62, No.11, 1504-1509, 1999.
(Summary)
A new sesterterpene, (2Z,6Z,10E)-cericerene-15,24-diol (1), and its 30-hydroxytriacontanoate (2) were isolated from the wax exuded by the scale insect Ceroplastes pseudoceriferus, together with the acetates and 30-hydroxytriacontanoates of 3,15-dihydroxy- and 15, 20-dihydroxylabda-7,13-diene (3-6). The absolute configurations of the labdadiene alcohols were antipodal to the ordinary labdanes isolated from terrestrial plants.
Masayori Ninomiya, Hideo Hirohara, Jun-ichi Onishi and Takenori Kusumi : Chemical Study and Absolute Configuration of a New Marine Secospatane from the Brown Alga Dilophus okamurae, The Journal of Organic Chemistry, Vol.64, No.15, 5436-5440, 1999.
(Summary)
A new diterpene, dilkamural (1), of the secospatane class has been isolated from the brown alga Dilophus okamurae Dawson, and its structure, including absolute stereochemistry, has been determined by NMR spectroscopic and chemical means.
Kyoji Kouda, Takashi Ooi and Takenori Kusumi : Application of the modified Mosher's method to linear 1,3-diols, Tetrahedron Letters, Vol.40, No.15, 3005-3008, 1999.
H Yamase, K Umemoto, Takashi Ooi and Takenori Kusumi : Structure and Absolute Stereochemistry of Five New Secospatanes and a Spatane Isolated from the Brown Alga Dilophus okamurai Dawson, Chemical & Pharmaceutical Bulletin, Vol.47, No.6, 813-818, 1999.
31.
T Yabuuchi and Takenori Kusumi : A Convenient One-pot Synthesis of Quaternary a-Methoxy-& a-Hydroxycarboxylic Acids, Chemical & Pharmaceutical Bulletin, Vol.47, No.5, 684-686, 1999.
32.
Hiroshi Yamase, Takashi Ooi and Takenori Kusumi : Determination of the absolute configuration of linear secondary alcohols adopting one enantiomer of the chiral anisotropic reagents, methoxy-(1-and 2-naphthyl)acetic acids, Tetrahedron Letters, Vol.39, No.44, 8113-8116, 1998.
M Ninomiya, J Onishi and Takenori Kusumi : 12-Lipoxygenase Inhibitory Activity of Japanese Seaweeds and Isolation of a Caulerpyne Derivative from the Green Alga Caulerpa taxifolia as an Inhibitor, Fisheries Science, Vol.64, No.2, 346-347, 1998.
34.
M Takikawa, K Uno, Takashi Ooi, Takenori Kusumi, S Akera, M Muramatsu, H Mega and C Horita : Crenulacetal C, a Marine Diterpene, and Its Synthetic Mimics Inhibiting Polydora websterii, a Harmful Lugworm Damaging Peral Cultivation, Chemical & Pharmaceutical Bulletin, Vol.46, No.3, 462-466, 1998.
35.
Tatsuo Munakata, Takashi Ooi and Takenori Kusumi : A simple preparation of 17(R)-hydroxyeicosatetraenoic and eicosapentaenoic acids from the eicosanoylphloroglucinols, components of the brown alga, Zonaria diesingiana, Tetrahedron Letters, Vol.38, No.2, 249-250, 1997.
Y Inoue, T Yabuuchi and Takenori Kusumi : Conformation of (S,S)-Methyl (2-Methyl-4-phenylbutanamido)(phenyl)acetate, Acta Crystallographica Section C, Vol.C53, IUC970017, 1997.
37.
Tetsuya Yabuuchi, Takashi Ooi and Takenori Kusumi : Application of phenylglycine methyl ester (PGME) to determination of the absolute configuration of carboxylic acids having phenylalkyl group, Chirality, Vol.9, No.5-6, 550-555, 1997.
Akio Ichikawa, Haruko Takahashi, Takashi Ooi and Takenori Kusumi : Absolute Configurations of Some Hydroxy-fatty Acids Produced by the Insect Genus Laccifer, Bioscience, Biotechnology, and Biochemistry, Vol.61, No.5, 881-883, 1997.
39.
Haruko Takahashi, Takenori Kusumi, Yukiko Kan, Masayuki Satake and Takeshi Yasumoto : Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid, Tetrahedron Letters, Vol.37, No.39, 7087-7090, 1996.
Kyoji Kouda, Takashi Ooi, Kunimitsu Kaya and Takenori Kusumi : Absolute stereostructure of a 2,3,7,13-tetrahydroxyoctadecanoic acid, the framework of taurolipid B produced by a fresh-water protozoan, Tetrahymena thermophila, Tetrahedron Letters, Vol.37, No.35, 6347-6350, 1996.
Yasushi Ohizumi, Susumu Sasaki, Takenori Kusumi and Ikuko I. Ohtani : Ptilomycalin A, a novel Na+,K+- or Ca2+-ATPase inhibitor, competitively interacts with ATP at its binding site, European Journal of Pharmacology, Vol.310, No.1, 95-98, 1996.
Kyoji Kouda, Takenori Kusumi, Xu Ping, Yukiko Kan, Toshihiro Hashimoto and Yoshinori Asakawa : 2-Anthrylmethoxyacetic acid, a new chiral anisotropic reagent for elucidating the absolute configuration of acyclic alcohols, Tetrahedron Letters, Vol.37, No.26, 4541-4544, 1996.
43.
Takenori Kusumi and S Matsuka : Antioxidant Activities of Macroalgal Components, Fragrance Journal, Vol.27, No.4, 36-41, 1996.
44.
Isao Kubo, V Jamalamadaka, T Kamikawa, K Takahashi, K Tabata and Takenori Kusumi : Absolute Stereochemistry of Tanabalin an Insect Antifeedant Clerodane from Tanacetum balsamita, Chemistry Letters, No.6, 441-442, 1996.
45.
F Nakanishi, Takenori Kusumi and Y Inouye : Dhydrokaempferol Glucoside from Cotyledons Promotes Flowering in Pharbitis nil, Plant & Cell Physiology, Vol.7, 1303-1309, 1996.
46.
Yuriko Nagai and Takenori Kusumi : New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids, Tetrahedron Letters, Vol.36, No.11, 1853-1856, 1995.
Fumika Asari, Takenori Kusumi, Guo-Zhi Zheng, Ying-Zhou Cen and Hiroshi Kakisawa : Cryptoacetalide and Epicryptoacetalide, Novel Spirolactone Diterpenoids from Salvia miltiorrhiza, Chemistry Letters, Vol.19, No.10, 1885-1888, 1990.
48.
Fumika Asari, Takenori Kusumi and Hiroshi Kakisawa : Turbinaric Acid, a Cytotoxic Secosqualene Carboxylic Acid from the Brown Alga Turbinaria ornata, Journal of Natural Products, Vol.52, No.5, 1167-1169, 1989.
(Summary)
A moderately cytotoxic secosqualene carboxylic acid designated turbinaric acid [1] has been isolated from the brown alga Turbinaria ornata, and it has been identified to be 4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoic acid by means of spectral analysis and synthesis.