論文 - 末永　聖武

Isolation and structures of hedathiosulfonic acids A and B, novel thiosulfonic acids from the deep-sea urchin Echinocardium cordatum

Takada Noboru, Watanabe Masami, Suenaga Kiyotake, Yamada Kaoru, Kita Masaki, Uemura Daisuke

Tetrahedron Letters 42 （ 37 ） 6557 - 6560 2001年09月

査読有り,  ISSN  0040-4039

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<p>Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum, and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. Hedathiosulfonic acids exhibited acute toxicity.</p>

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Haterumaimides F-I, four new cytotoxic diterpene alkaloids from an ascidian Lissoclinum species

Uddin M. J., Kokubo S., Ueda K., Suenaga K., Uemura D.

Journal of Natural Products 64 （ 9 ） 1169 - 1173 2001年09月

査読有り,  ISSN  0163-3864

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<p>Four new monochlorinated diterpene alkaloids, haterumaimides F-I (1-4), and two known ones, dichlorolissoclimide and chlorolissoclimide, were isolated from an ascidian Lissoclinum sp. Their structures with absolute stereochemistries were elucidated by chemical and spectral analyses. Haterumaimides F-I (1-4) inhibited the first cleavage of fertilized sea urchin eggs and exhibited potent to weak cytotoxicities against P388 cells.</p>

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Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea

Takada Noboru, Watanabe Reiko, Suenaga Kiyotake, Yamada Kaoru, Ueda Katsuhiro, Kita Masaki, Uemura Daisuke

Tetrahedron Letters 42 （ 31 ） 5265 - 5267 2001年07月

査読有り,  ISSN  0040-4039

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<p>Zamamistatin was isolated from the Okinawan sponge Pseudoceratina purpurea. It was determined to be a novel bromotyrosine derivative by careful analysis of 2D NMR spectra and comparison of its ¹H NMR spectrum with those of structurally related compounds. The absolute stereostructure of zamamistatin was determined by the modified Mosher's method. Zamamistatin exhibited significant antibacterial activity against Rhodospirillum salexigens, which has adhering properties.</p>

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Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin

Takada Noboru, Umemura Naoyashi, Suenaga Kiyotake, Uemura Daisuke

Tetrahedron Letters 42 （ 20 ） 3495 - 3497 2001年05月

査読有り,  ISSN  0040-4039

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<p>Pteriatoxins A, B and C, extremely potent toxins, were isolated from the Okinawan bivalve Pteria penguin. Their structures were determined based on NMR and MS/MS spectral analyses. Pteriatoxins have polyether macrocycles composed of 6,7-spiro, 5,6-bicyclo and 6,5,6-trispiro ketal rings, the same as in pinnatoxins.</p>

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Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata

Takada Noboru, Umemura Naoyoshi, Suenaga Kiyotake, Chou Tong, Nagatsu Akito, Haino Takeharu, Yamada Kaoru, Uemura Daisuke

Tetrahedron Letters 42 （ 20 ） 3491 - 3494 2001年05月

査読有り,  ISSN  0040-4039

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<p>Pinnatoxins B and C, the most toxic components in the pinnatoxin series, were successfully purified from the Okinawan bivalve Pinna muricata. Their gross structures were determined based on NMR and MS/MS spectral analyses. Their stereostructures were mainly determined by transformation reactions. Pinnatoxins B and C, C-34 epimers of each other, have an amphoteric macrocycle composed of 6,7-spiro, 5,6-bicyclo and 6,5,6-trispiro ketal rings, the same as in pinnatoxins A and D.</p>

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Isolation and structures of hedaols A, B, and C, new bisnorditerpenes from a Japanese brown alga

Takada Noboru, Watanabe Reiko, Suenaga Kiyotake, Yamada Kaoru, Uemura Daisuke

Journal of Natural Products 64 （ 5 ） 653 - 655 2001年05月

査読有り,  ISSN  0163-3864

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<p>New bisnorditerpenes, hedaols A (1), B (2), and C (3), were isolated from the Japanese brown alga Sargassum sp. Their structures were determined by spectroscopic analysis. The absolute stereocenter of 1 was determined by the modified Mosher's method. Hedaols showed low cytotoxicity against P388 cells.</p>

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Isolation and structures of haterumadioxins A and B, cytotoxic endoperoxides from the Okinawan sponge Plakortis lita

Takada N., Watanabe M., Yamada A., Suenaga K., Yamada K., Ueda K., Uemura D.

Journal of Natural Products 64 （ 3 ） 356 - 359 2001年03月

査読有り,  ISSN  0163-3864

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<p>Cytotoxic endoperoxides, haterumadioxins A (1) and B (2), were isolated from the Okinawan sponge Plakortis lita. Their structures were determined by spectroscopic analysis. The absolute stereostructure of 1 was determined by degradation reactions and the modified Mosher's method. Haterumadioxins showed significant cytotoxicity against 38 human cancer cell lines.</p>

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Enantioselective synthesis of attenols A and B

Suenaga Kiyotake, Araki Keisuke, Sengoku Tetsuya, Uemura Daisuke

Organic Letters 3 （ 4 ） 527 - 529 2001年02月

査読有り,  ISSN  1523-7060

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<p>(Matrix presented) Enantioselective synthesis of attenols A and B was accomplished by using diastereoselective hydroboration, Lindlar reduction, and acid-catalyzed acetal formation.</p>

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Haterumaimides A-E, five new dichlorolissoclimide-type diterpenoids from an ascidian, Lissoclinum sp.

Uddin Md Jasim, Kokubo Susumu, Suenaga Kiyotake, Ueda Katsuhiro, Uemura Daisuke

Heterocycles 54 （ 2 ） 1039 - 1047 2001年02月

査読有り,  ISSN  0385-5414

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<p>Five new dichlorolissoclimide-type diterpenoids, haterumaimides A-E, were isolated from an ascidian, Lissoclinum sp., and the absolute stereostructures of haterumaimides A-D and the relative stereostructure of haterumaimide E were determined by spectroscopic and chemical analyses. Haterumaimides A-E inhibited the first cleavage of fertilized sea urchin eggs and exhibited cytotoxicity against P388 cells.</p>

Kohamaic acids A and B, novel cytotoxic sesterterpenic acids, from the marine sponge Ircinia sp

Kokubo Susumu, Yogi Kentaro, Uddin Md Jasim, Inuzuka Toshiyasu, Suenaga Kiyotake, Ueda Katsuhiro, Uemura Daisuke

Chemistry Letters  （ 2 ） 176 - 177 2001年02月

査読有り,  ISSN  0366-7022

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<p>Two new sesterterpenic acids, which exhibited moderate cytotoxicity, were isolated from the marine sponge Ircinia sp. Their absolute stereochemistries were determined by spectroscopic and chemical analyses. Their configurations at C15 were different from those of previously isolated sesterterpenes. This result suggests the existence of a (14Z)-geranylfarnesyl pyrophosphate, which is yet unknown in nature.</p>

Structures of amamistatins A and B, novel growth inhibitors of human tumor cell lines from Nocardia asteroides

Kokubo S., Suenaga K., Shinohara C., Tsuji T., Uemura D.

Tetrahedron 56 （ 35 ） 6435 - 6440 2000年08月

査読有り,  ISSN  0040-4020

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<p>Two new lipopeptides, amamistatins A and B, were isolated from Nocardia asteroides SCRC-A2359, and their absolute stereostructures were determined by spectroscopic and chemical analyses. Amamistatin A inhibited the growth of human rumor cell lines. (C) 2000 Elsevier Science Ltd.</p>

Pinnamine, an alkaloidal marine toxin, isolated from Pinna muricata

Takada N., Iwatsuki M., Suenaga K., Uemura D.

Tetrahedron Letters 41 （ 33 ） 6425 - 6428 2000年08月

査読有り,  ISSN  0040-4039

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<p>Pinnamine, a novel marine alkaloid, was isolated from the Okinawan bivalve Pinna muricata. Pinnamine was determined to be an alkaloid containing a dihydropyrone ring by spectroscopic analysis. The relative stereostructure of pinnamine was determined by an analysis of coupling constants and NOE experiments; the absolute stereostructure was determined by an analysis of the circular dichroism spectrum. Pinnamine exhibited significant acute toxicity against mice. (C) 2000 Elsevier Science Ltd.</p>

Isolation and structure of kasarin, a novel azetinone compound, isolated from a marine microorganism

Suenaga Kiyotake, Aoyama Sachiko, Xi Wang, Arimoto Hirokazu, Yamaguchi Kohji, Yamada Kaoru, Tsuji Tomoko, Yamada Akihiro, Uemura Daisuke

Heterocycles 52 （ 3 ） 1033 - 1036 2000年03月

査読有り,  ISSN  0385-5414

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<p>Kasarin (1), a novel azetinone compound, was isolated from a marine microorganism. The gross structure of kasarin was elucidated by spectroscopic analyses. Kasarin exhibited antibacterial activity and weak cytotoxicity.</p>

Isolation and structures of haterumalides NA, NB, NC, ND, and NE, novel macrolides from an Okinawan sponge Ircinia sp.

Takada Noboru, Sato Hiroko, Suenaga Kiyotake, Arimoto Hirokazu, Yamada Kaoru, Ueda Katsuhiro, Uemura Daisuke

Tetrahedron Letters 40 （ 34 ） 6309 - 6312 1999年08月

査読有り,  ISSN  0040-4039

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<p>Novel macrolides, haterumalides NA (1), NB (2), NC (3), ND (4), and NE (5), were isolated from an Okinawan sponge Ircinia sp. The absolute stereostructure of 1 was determined by spectroscopic analysis and modified Mosher's method. Haterumalide NA (1) showed cytotoxicity against P388 cells and acute toxicity against mice.</p>

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Structures of amamistatins A and B, novel growth inhibitors of human tumor cell lines from an actinomycete

Suenaga K., Kokubo S., Shinohara C., Tsuji T., Uemura D.

Tetrahedron Letters 40 （ 10 ） 1945 - 1948 1999年03月

査読有り,  ISSN  0040-4039

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<p>Two new lipopeptides, amamistatins A (1) and B, were isolated from an actinomycete. The absolute stereostructure of 1 was determined by spectroscopic and chemical analyses. Amamistatins A (1) and B showed growth inhibition for human tumor cell lines.</p>

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Isolation and structures of attenols A and B. novel bicyclic triols from the Chinese bivalve Pinna attenuata

Takada Noboru, Suenaga Kiyotake, Yamada Kaoru, Zheng Shu Zhen, Chen Hai Sheng, Uemura Daisuke

Chemistry Letters  （ 10 ） 1025 - 1026 1999年

査読有り,  ISSN  0366-7022

　概要を見る

<p>Novel bicyclic triols, attenols A (1) and B (2), were isolated from the Chinese bivaive Pinna attenuata. The absolute stereostructures of 1 and 2 were determined by spectroscopic analysis and the modified Mosher's method. These attenols exhibited moderate cytotoxicity against P388 cells.</p>

Aurilol, a cytotoxic bromotriterpene isolated from the sea hare Dolabella auricularia

Suenaga K., Shibata T., Takada N., Kigoshi H., Yamada K.

Journal of Natural Products 61 （ 4 ） 515 - 518 1998年04月

査読有り,  ISSN  0163-3864

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<p>Aurilol (1), a novel cytotoxic bromotriterpene, was isolated from the sea hare Dolabella auricularia. The structure of 1, including the absolute stereochemistry of the five stereocenters, was determined by spectroscopic and chemical analyses. Aurilol (1) exhibited cytotoxicity against HeLa S₃ cells with an IC₅₀ of 4.3 μg/mL.</p>

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Synthesis of the aglycon of aurisides A and B, cytotoxic macrolide glycosides of marine origin

Sone Hiroki, Suenaga Kiyotake, Bessho Yuhki, Kondo Takashi, Kigoshi Hideo, Yamada Kiyoyuki

Chemistry Letters  （ 1 ） 85 - 86 1998年01月

査読有り,  ISSN  0366-7022

　概要を見る

<p>The synthesis of the aglycon of aurisides A and B was achieved from (R)-pantolactone in 29 steps using the Nozaki reaction and the Yamaguchi macrolactonization as key steps.</p>

Cytotoxicity and actin depolymerizing activity of aplyronine A, a potent antitumor macrolide of marine origin, and the natural and artificial analogs

Suenaga Kiyotake, Kamei Noriyuki, Okugawa Youko, Takagi Masaki, Akao Atsushi, Kigoshi Hideo, Yamada Kiyoyuki

Bioorganic and Medicinal Chemistry Letters 7 （ 3 ） 269 - 274 1997年02月

査読有り,  ISSN  0960-894X

　概要を見る

<p>The artificial analogs of aplyronine A (1), a potent cytotoxic and antitumor macrolide, were synthesized and the structure-activity (cytotoxicity and actin depolymerizing activity) studies were performed; the side chain portion in 1 was found to play a key role in both biological activities.</p>

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Enantioselective Synthesis of Aurilide, a Cytotoxic 26-Membered Cyclodepsipeptide of Marine Origin

Mutou Tsuyoshi, Suenaga Kiyotake, Fujita Tatsuya, Itoh Takashi, Takada Noboru, Hayamizu Kozue, Kigoshi Hideo, Yamada Kiyoyuki

Synlett 1997 （ 2 ） 199 - 201 1997年02月

ISSN  0936-5214

　概要を見る

<p>Aurilide (1), a novel cyclodepsipeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, and the present result unambiguously confirmed its stereostructure. In addition, the cytotoxicity of 1 was evaluated by employing synthetic 1.</p>