論文 - 末永　聖武

Allelopathy and the allelopathic activity of a phenylpropanol from cucumber plants

Le Thi Ho, Teruya Toshiaki, Suenaga Kiyotake, Van Chin Duong, Kato-Noguchi Hisashi

Plant Growth Regulation 56 （ 1 ） 1 - 5 2008年05月

査読有り,  ISSN  0167-6903

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An unusual iodinated 5′-deoxyxylofuranosyl nucleoside from an Okinawan Ascidian, Diplosoma sp.

Margiastuti Pulpi, Ogi Takayuki, Teruya Toshiaki, Taira Junsei, Suenaga Kiyotake, Ueda Katsuhiro

Chemistry Letters 37 （ 4 ） 448 - 449 2008年04月

査読有り,  ISSN  0366-7022

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<p>An unusual nucleoside, 4-amino-7-(5′-deoxy-β-D-xylofuranosyl)-5- iodopyrrolo[2,3-d]pyrimidine (1), was isolated from an ascidian, Diplosoma sp., and its structure was successfully determined by spectroscopic and chemical analysis. The known didemnenones 2-5 were also isolated. Compound 1 was found to inhibit the division of fertilized sea urchin eggs.</p>

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Synthetic studies on mycalolide B

Kimura Tomoyuki, Kuribayashi Satomi, Sengoku Tetsuya, Matsui Keita, Ueda Shoko, Hayakawa Ichiro, Suenaga Kiyotake, Kigoshi Hideo

Chemistry Letters 36 （ 12 ） 1490 - 1491 2007年12月

査読有り,  ISSN  0366-7022

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<p>Mycalolide B, a cytotoxic macrolide isolated from a marine sponge of the genus Mycale, has an actin depolymerizing activity. This paper reports the synthesis of C7-C35 fragment of mycalolides via cross olefin metathesis reaction between trisoxazole fragment and side-chain fragment.</p>

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Isolation and structure elucidation of a potent growth inhibitor, helian, from blue light-illuminated sunflower (Helianthus annuus) hypocotyls

Hasegawa Tsuyoshi, Togo Shigenori, Hisamatsu Yosuke, Yamada Kosumi, Suenaga Kiyotake, Sekiguchi Mitsuhiro, Shigemori Hideyuki, Hasegawa Koji

Heterocycles 71 （ 3 ） 609 - 617 2007年03月

査読有り,  ISSN  0385-5414

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<p>A potent growth inhibitor was isolated from blue light-illuminated sunflower (Helianthus annuus) hypocotyls and identified as 8-(β-D-glucopyranosyloxy)-3-hydroxy-1,9,14-pentadecatriene-4,6-diyne (1, designated "helian") from analysis of its ¹H and ¹³C NMR spectra, and HRFABMS. Helian 1 showed plant growth-inhibitory activity at concentrations higher than 2.6 × 10^-6 mol/L for the cress root growth test. The amount of helian was higher in the illuminated halves than in the shaded ones in phototropically stimulated sunflower hypocotyls. These results suggest that this new potent growth inhibitor, helian, may play an important role on phototropism of sunflower hypocotyls.</p>

Synthesis and biological activity of actin-depolymerizing substances

Suenaga Kiyotake, Kigoshi Hideo

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 64 （ 12 ） 1273 - 1281 2006年12月

査読有り,  ISSN  0037-9980

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<p>Aplyronine A 1 is a potent antitumor macrolide isolated from the sea hare Aplysia kurodai. Aplyronine A interacts with actin, one of the major proteins in cytoskeleton. We achieved total synthesis of aplyronine A and its 18 analogs and investigated structure-activity relationships. Analysis of the interaction of aplyronine analogs with actin by a photoaffinity labeling method and X-ray crystal structure analysis of actin complex with aplyronine A have been carried out. These results revealed that aplyronine A binds to actin at the hydrophobic cleft between subdomains 1 and 3 of actin. The binding mode of the macrolactone part of aplyronine A was different from previously reported macrolides. In addition, the trimethylserine moiety of aplyronine A, the essential functional group for cytotoxicity against HeLa S₃ cells, was sticking out from a surface of actin-aplyronine A complex.</p>

Synthesis and biological activity of mycalolide analogs

Suenaga Kiyotake, Kimura Tomoyuki, Kuroda Takeshi, Matsui Keita, Miya Saori, Kuribayashi Satomi, Sakakura Akira, Kigoshi Hideo

Tetrahedron 62 （ 35 ） 8278 - 8290 2006年08月

査読有り,  ISSN  0040-4020

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<p>Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity.</p>

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Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin

Suenaga Kiyotake, Hoshino Hiroshi, Yoshii Takanori, Mori Kazunori, Sone Hiroki, Bessho Yuhki, Sakakura Akira, Hayakawa Ichiro, Yamada Kiyoyuki, Kigoshi Hideo

Tetrahedron 62 （ 33 ） 7687 - 7698 2006年08月

査読有り,  ISSN  0040-4020

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<p>The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1-C9 segment 4 was prepared from (R)-pantolactone, and the C10-C17 segment 14 was synthesized from (R)-glycidyl trityl ether. The Nozaki-Hiyama-Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon (3) of aurisides by construction of the 14-membered lactone and bromine-substituted conjugated diene. The glycosylation reaction of the aglycon provided aurisides A and B.</p>

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Isotheasaponins B₁-B₃ from Camellia sinensis var. sinensis tea leaves

Kobayashi Keiko, Teruya Toshiaki, Suenaga Kiyotake, Matsui Yoko, Masuda Hideki, Kigoshi Hideo

Phytochemistry 67 （ 13 ） 1385 - 1389 2006年07月

査読有り,  ISSN  0031-9422

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<p>Three saponins, isotheasaponins B₁-B₃, were isolated from the leaves of the tea plant Camellia sinensis var. sinensis, and their structures were determined to be theasapogenol B [β-d-galactopyranosyl(1 → 2)][β-d-xylopyranosyl(1 → 2)-α-l-arabinopyranosyl(1 → 3)]-β-d-gulcopyranosiduronic acid with two acyl groups by spectroscopic analysis.</p>

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Structure basis for antitumor effect of aplyronine A

Hirata Kunio, Muraoka Shin, Suenaga Kiyotake, Kuroda Takeshi, Kato Kenichi, Tanaka Hiroshi, Yamamoto Masaki, Takata Masaki, Yamada Kiyoyuki, Kigoshi Hideo

Journal of Molecular Biology 356 （ 4 ） 945 - 954 2006年03月

査読有り,  ISSN  0022-2836

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<p>Aplyronine A, isolated from the sea hare Aplysia kurodai, possesses an exceedingly potent antitumor effect in vivo and it is one of the promising candidates as an anticancer drug. This macrolide is known to depolymerize F-actin and inhibit the polymerization of actin by forming a 1:1 complex with monomeric actin. The first complex structure of actin-aplyronine A was determined via a synchrotron X-ray analysis at a 1.45 Å resolution. As expected, aplyronine A binds to a hydrophobic cleft composed of subdomains 1 and 3 of actin by intercalating its aliphatic tail part into the actin molecule as do the other reported F-actin depolymerizing agents. Unexpectedly, this complex structure shows the specific structural features around the trimethylserine moiety, revealed as an important moiety of aplyronine A for cytotoxicity against HeLa cells. Combining this result and our previous one, the moiety should strongly relate to the specific biological activity of aplyronine A; i.e. a potent antitumor effect.</p>

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Study of the interaction between actin and antitumor substance aplyronine A with a novel fluorescent photoaffinity probe

Kuroda Takeshi, Suenaga Kiyotake, Sakakura Akira, Handa Tomohisa, Okamoto Kazuhito, Kigoshi Hideo

Bioconjugate Chemistry 17 （ 2 ） 524 - 529 2006年03月

査読有り,  ISSN  1043-1802

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<p>The interaction between actin and aplyronine A, a potent antitumor and actin-depolymerizing substance of marine origin, was investigated by photoaffinity labeling experiments. Photoaffinity probes consisting of a side-chain portion of aplyronine A as a ligand, a diazirine moiety as a photoaffinity group, and a fluorophore as a detecting group were synthesized. Photolabeling experiments between actin and the probe were carried out. Actin was successfully photolabeled by the fluorescent probe and visualized clearly. The present results provide the first chemical evidence for the direct interaction between actin and the side-chain portion of aplyronine A.</p>

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Cinachyramine, the novel alkaloid possessing a hydrazone and two aminals from Cinachyrella sp.

Shimogawa Hiroki, Kuribayashi Satomi, Teruya Toshiaki, Suenaga Kiyotake, Kigoshi Hideo

Tetrahedron Letters 47 （ 9 ） 1409 - 1411 2006年02月

査読有り,  ISSN  0040-4039

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<p>The trifluoroacetate salt of cinachyramine (1) was isolated from the Okinawan sponge Cinachyrella sp. This structure was determined by the spectroscopic analysis and the degradation under acidic conditions. Cinachyramine (1) is a novel alkaloid with an unprecedented cage system possessing a hydrazone and two aminals.</p>

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Growth inhibitory polyacetylenes from galls of Hedera rhombea Bean

Yamazoe Sayumi, Hasegawa Koji, Suenaga Kiyotake, Shigemori Hideyuki

Natural Product Communications 1 （ 2 ） 87 - 94 2006年02月

査読有り,  ISSN  1934-578X

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<p>Plant growth inhibitory polyacetylenes have been isolated from the insect galls on flower buds of Hedera rhombea Bean (Araliaceae) formed by the ivy flower bud gall midge, Asphondylia sp. (Cecidomyiidae), and their structures elucidated by spectroscopic and chemical means. The EC₅₀ values for roots/hypocotyls growth of cress (Lepidium sativum L.) seedlings were 7.0×10^-5/8.0×10^-5 M for (Z)-8-acetoxy-1,2- epoxy-3-oxoheptadeca-9-ene-4,6-diyne, 9.5×10-5/9.0×10^-5 M for (Z)-8-acetoxy-3-oxoheptadeca-1,9-diene-4,6-diyne, 2.5×10-5/5. 5×10-6 M for (Z)-8-acetoxy-1-methoxy-3-oxoheptadeca-9-ene-4,6-diyne, and 7.5×10^-5/2.0×10^-6 M for falcarindiol, respectively. On the other hand, 8-acetoxyfalcarinol exhibited lower inhibition on roots and hypocotyls growth. Among these compounds, (Z)-8-acetoxy-1-methoxy- 3-oxoheptadeca-9-ene-4,6-diyne exhibited the strongest inhibitiory effect on root growth of cress seedlings, whereas against hypocotyl growth of cress seedlings, falcarindiol showed the strongest inhibition.</p>

Cyclohaliclonamines A-E

Teruya Toshiaki, Kobayashi Keiko, Suenaga Kiyotake, Kigoshi Hideo

Journal of Natural Products 69 （ 1 ） 135 - 137 2006年01月

査読有り,  ISSN  0163-3864

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<p>A mixture of cyclohaliclonamines A-E (1-5), novel dimeric, trimeric, tetrameric, pentameric, and hexameric 3-alkylpyridinium alkaloids, was obtained from an Okinawan sponge Haliclona sp. Cyclohaliclonamines C-E are the first tetrameric, pentameric, and hexameric 3-alkylpyridinium alkaloids from natural sources. The structure determination of cyclohaliclonamines is discussed in detail.</p>

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Isolation of two 13-epi-neoverrucosane-type diterpenoids from a marine sponge Axinyssa tethyoides

Shimogawa Hiroki, Teruya Toshiaki, Suenaga Kiyotake, Kigoshi Hideo

Bulletin of the Chemical Society of Japan 78 （ 7 ） 1345 - 1347 2005年07月

査読有り,  ISSN  0009-2673

　概要を見る

<p>New 13-epi-neoverrucosane-type diterpenes 1 and 2 were isolated from the marine sponge Axinyssa tethyoides. Their structures were elucidated by 2D-NMR spectroscopy, the modified Mosher's method, and fluorescent X-ray analysis. 1 and 2 are the first 13-epi-neoverrucosane-type diterpenes that possess a sulfate group.</p>

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Synthetic studies of norzoanthamine. Preparation of the diene-yne-diene precursor of an ABC-ring fragment

Irifune Taiji, Ohashi Tomohiro, Ichino Takao, Sakai Emi, Suenaga Kiyotake, Uemura Daisuke

Chemistry Letters 34 （ 7 ） 1058 - 1059 2005年07月

査読有り,  ISSN  0366-7022

　概要を見る

<p>The diene-yne-diene precursor of the ABC-ring fragment of norzoanthamine, a bioactive alkaloid from the colonial zoanthid Zoanthus sp., was prepared.</p>

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Biselides A-E: novel polyketides from the Okinawan ascidian Didemnidae sp.

Teruya Toshiaki, Suenaga Kiyotake, Maruyama Sakiko, Kurotaki Mineko, Kigoshi Hideo

Tetrahedron 61 （ 27 ） 6561 - 6567 2005年07月

査読有り,  ISSN  0040-4020

　概要を見る

<p>Five new polyketides, biselides A (1), B (2), C (3), D (4), and E (5), were isolated from the Okinawan ascidian Didemnidae sp. Their structures were determined by spectroscopic analysis. Biselides A (1), B (2), and C (3) showed cytotoxicity against human cancer cells NCI-H460 and MDA-MB-231.</p>

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Phormidinines A and B, novel 2-alkylpyridine alkaloids from the cyanobacterium Phormidium sp.

Teruya Toshiaki, Kobayashi Keiko, Suenaga Kiyotake, Kigoshi Hideo

Tetrahedron Letters 46 （ 23 ） 4001 - 4003 2005年06月

査読有り,  ISSN  0040-4039

　概要を見る

<p>Novel 2-alkylpyridine alkaloids, phormidinines A (1) and B (2), were isolated from cyanobacterium Phormidium sp. Their structures were determined by spectroscopic analysis. The absolute stereochemistry of 1 was established by the modified Mosher's method.</p>

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Formal synthesis of optically active ingenol via ring-closing olefin metathesis

Watanabe Kazushi, Suzuki Yuto, Aoki Kenta, Sakakura Akira, Suenaga Kiyotake, Kigoshi Hideo

Journal of Organic Chemistry 69 （ 23 ） 7802 - 7808 2004年11月

査読有り,  ISSN  0022-3263

　概要を見る

<p>The construction of strained carbon skeletons by ring-closing olefin metathesis (RCM) was investigated. With well-designed diene 4, RCM was found to be applicable to the formation of a highly strained inside-outside bicyclo[4.4.1]undecane skeleton of ingenol, a bioactive diterpenoid, and formal total synthesis of optically active ingenol (1) was achieved. The key features of this synthesis are construction of an A-ring by spirocyclization of the ketone with an allylic chloride unit, 26, and ring closure of a B-ring by olefin metathesis. Starting from Funk's keto ester 6, the key intermediate aldehyde 9 in Winkler's total synthesis was synthesized in eight steps in 12.5% overall yield. This strategy of direct cyclization of a strained inside-outside skeleton provided the first easy access to optically active ingenol.</p>

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Spongiacysteine, a novel cysteine derivative from marine sponge Spongia sp.

Kobayashi Keiko, Shimogawa Hiroki, Sakakura Akira, Teruya Toshiaki, Suenaga Kiyotake, Kigoshi Hideo

Chemistry Letters 33 （ 10 ） 1262 - 1263 2004年10月

査読有り,  ISSN  0366-7022

　概要を見る

<p>A novel cysteine derivative, spongiacysteine (1), was isolated from marine sponge Spongia sp. The gross structure was elucidated by detailed spectroscopic analysis, and the absolute stereostructure was established by its total synthesis. This compound showed moderate antimicrobial activity against rice blast fungus Pyricularia oryzae.</p>

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Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: isolation, structure determination, synthesis, and biological activity

Suenaga Kiyotake, Mutou Tsuyoshi, Shibata Takunobu, Itoh Takashi, Fujita Tatsuya, Takada Noboru, Hayamizu Kozue, Takagi Masaki, Irifune Taiji, Kigoshi Hideo, Yamada Kiyoyuki

Tetrahedron 60 （ 38 ） 8509 - 8527 2004年09月

査読有り,  ISSN  0040-4020

　概要を見る

<p>The bioassay-guided fractionation of the cytotoxic constituents of the Japanese sea hare Dollabella auricularia led to the isolation of aurilide (1), a 26-membered cyclodepsipeptide. The gross structure of 1 was established by spectroscopic analysis including 2D NMR techniques. The absolute stereostructure was determined by chiral HPLC analysis of acid hydrolysates of 1 and by the enantioselective synthesis of a degradation product arising from a dihydroxylated fatty acid portion. The enantioselective synthesis of 1 was achieved in 12% overall yield (16 steps) and confirmed the absolute stereostructure of 1. The cytotoxicity of 1 was evaluated using a synthetic sample, which was found to exhibit potent cytotoxicity against HeLa S ₃ cells with an IC₅₀ of 0.011 μg/mL. Further biological and pharmacological studies of 1 have been carried out by using synthetic 1. Graphical abstract.</p>

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