Faculty Profiles - KUBOTA Takaaki

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スギカズラ(Lycoposiumannotinum)より単離した新規アルカロイドの構造

石内勘一郎, 児玉志保美, 久保田高明, 小林淳一, 林茂樹, 柴田敏郎

日本生薬学会年会講演要旨集 56th 141 2009.9

エゾオトギリHypericum yezoenseより単離したyezo’otogirin A‐Cの構造

田中直伸, 格口ゆか, 石山玄明, 久保田高明, 小林淳一

日本生薬学会年会講演要旨集 56th 256 2009.9

海綿由来の新規マンザミンアルカロイドzamamidine A〜Cの構造と生物活性

高橋洋平, 山田美香, 久保田高明, 石山亜紀, 乙黒一彦, 山田陽城, 大村智, 小林淳一

天然有機化合物討論会講演要旨集 51st ( 51 ) 581-586 - 586 2009.9

Language：Japanese Publisher：Symposium on the chemistry of natural products

Manzamine alkdloids are well known to be a group of marine natural products, which have a β-carboline moiety and a unique heterocyclic ring system. Since manzamine A had been isolated from a marine sponge Haliclona sp. in 1986, approximately 100 manzamine alkdloids containing biogenetic precursors have been idolated so far. A great number of studies on them, such as isolation and structural analysis, biosynthesis, and total synthesis, have been actively performed due to their intriguing structures and intersting biological activities. We have also isolated s seris of manzamine alkaloids from several genera and their structures have been elucidated by means of NMR spectra, chemical correlations, X-ray crystallography, and CD spectra. During our continuous search for structurally interesting metabolites from marine sponges, new manzamine alkdloids, zamamidines A-C (1-3), have been isolated, and their structures were elucidated by spectroscopic data. 1-3 are new manzamine alkdloids possessing a second β-carboline ring via an ethylene chain at N-2 of manzamine H, 1,2,3,4-tetrahydromanzamine B, and manzamine D, respectively. Since no manzamine alkdloids possessing any side chain at N-2 other than a methyl group have been reported to date, 1〜3 are the first examples of it. Zamamidines A-C (1-3) showed inhibitory activities against Plasmodium falciparum (Kl strain) and Tripanosoma brucei brucei (GUTat 3.1) in vitro.

DOI： 10.24496/tennenyuki.51.0_581

アスヒカズラ(Lycopodium complanatum)由来新規アルカロイドの構造

石内勘一郎, 久保田高明, 林茂樹, 柴田敏郎, 小林淳一

天然有機化合物討論会講演要旨集 51st ( 51 ) 19-24 - 24 2009.9

Language：Japanese Publisher：Symposium on the chemistry of natural products

Club moss (Lycopodiaceae) is known to be a rich source of Lycopodium alkaloids possessing unique heterocyclic ring systems such as C_<16>N, C_<16>N_2, and C_<27>N_3, which have attracted great interest from biogenetic, synthetic, and biological points of view. In our continuing efforts to find new Lycopodium alkaloids, lycopladine H (1), lyconadins C-E (2-4), lycoplaidines F-G (5-6), and complanadine E (7) were isolated from Lycopodium domplanatum. The structures for 1-7 were elucidated on the basis of spectral data. Lycopladine H (1) is an unprecedented C_<16>N-type Lycopodium alkaloid possessing a novel fused-tetracyclic ring system consisting of an azocane ring fused to a [2,2,2,]-bicyclooctane ring and 3-piperidinone ring, Lyconadin C (2) is a new tetracyclic Lycopodium alkaloid consisting of cyclohexane, cycloheptane, pyperidine, and pyridone rings. Lyconadin C (2) might be a biosynthetic precursor of lyconadin A. Lyconadins D (3) and E (4) are the first fastigiatine-type alkaloids isolated from Lycopodium complanatum. Lycopladine F (5) is a rare C_<16>N_2-type Lycopodium alkaloid possessing an amino acid residue (C_4N), while lycopladine G (6) is a 17-keto and 20-methylester form of lycopladine F (5). Complanadine E (7) is a new dimeric Lycopodium alkaloid consisting of two C_<16>N_2-type skeletons, which corresponds to 1,2,3,4,5,N-1-hexahydro complanadine A.

DOI： 10.24496/tennenyuki.51.0_19

Corrigendum to "Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp." [Tetrahedron 65 (2009) 2313-2317] (DOI:10.1016/j.tet.2009.01.032)

Mika Yamada, Yohei Takahashi, Takaaki Kubota, Jane Fromont, Aki Ishiyama, Kazuhiko Otoguro, Haruki Yamada, Satoshi Omura, Jun'ichi Kobayashi

Tetrahedron 65 ( 31 ) 6263 - 6263 2009.8

渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成による立体化学の解明

萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

次世代を担う有機化学シンポジウム講演要旨集 7th 38-39 2009.5

沖縄産海綿由来の新規ブロモチロシンアルカロイドTyrokeradine AおよびBの構造

久保田高明, 向井裕也, 小林淳一

日本薬学会年会要旨集 129th ( 2 ) 179 2009.3

渦鞭毛藻由来マクロリド・Amphidinolactone Aの全合成と立体化学の解明

萩行正博, 石山玄明, 高橋洋平, 久保田高明, 小林淳一

日本薬学会年会要旨集 129th ( 2 ) 95 2009.3

アスヒカズラより単離した新規リコポジウムアルカロイドの構造

石内勘一郎, 久保田高明, 柴田敏郎, 小林淳一

日本薬学会年会要旨集 129th ( 2 ) 97 2009.3

ビヨウヤナキより単離した新規xanthone誘導体の構造

田中直伸, 大豆村拓自, 久保田高明, 今林潔, 柏田良樹, 高石喜久, 小林淳一

日本薬学会年会要旨集 129th ( 2 ) 172 2009.3

アカネ科植物由来の新規モノテルペンインドールアルカロイド・Naucleamide Fの構造

石山玄明, 格口ゆか, 高橋洋平, 久保田高明, 小林淳一

日本薬学会年会要旨集 129th ( 2 ) 179 2009.3

沖縄産Agelas属海綿より単離した新規ブロモピロールアルカロイドの構造

荒木敦, 久保田高明, 三上襄, 小林淳一

天然薬物の開発と応用シンポジウム講演要旨集 17th 79-80 2008.11

沖縄産海綿より単離したnakijiquinone/metachromin類の構造と生物活性

高橋洋平, 久保田高明, 三上襄, 小林淳一

天然有機化合物討論会講演要旨集 50th 59-64 2008.9

6 Nakijiquinones and Metachromins, New Sesquiterpenoid Quinones from Okinawan Marine Sponges : Isolation, Structure Elucidation, and Biological Activities(Oral Presentation)

Takahashi Yohei, Kubota Takaaki, Mikami Yuzuru, Kobayashi Jun'ichi

Symposium on the Chemistry of Natural Products, symposium papers 0 ( 50 ) 59 - 64 2008.9

Language：Japanese Publisher：Symposium on the chemistry of natural products

Sesquiterpenoid quinines and hydroquinones are representative marine natural products with unique structures and interesting biological activities. In our continuous search for bioactive compounds having unique structures from Okinawan marine sponges, we have isolated new sesquiterpenoid quinones, nakijiquinones E〜I (1〜5) and metachromins L-Q (6〜11), from three collections of Okinawan marine sponges. The structures of 1〜5 were elucidated on the basis of 2D NMR data, while those of 6〜11 were established by chemical correlations. Furthermore, biological activities for 1〜11 and synthetic metac...

DOI： 10.24496/tennenyuki.50.0_59

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P-33 Nagelamides K, M, and N, Novel Bromopyrrole Alkaloids from Okinawan Marine Sponge Agelas sp(Poster Presentation)

Araki Atsushi, Yasuda Tetsuro, Kubota Takaaki, Mikami Yuzuru, Kobayashi Jun'ichi

Symposium on the Chemistry of Natural Products, symposium papers 0 ( 50 ) 361 - 366 2008.9

Language：Japanese Publisher：Symposium on the chemistry of natural products

DOI： 10.24496/tennenyuki.50.0_361

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ナガサキオトギリ由来の新規フロログルシノール誘導体petiolin Dの構造

田中直伸, 久保田高明, 石山玄明, 小林淳一, 柏田良樹, 高石喜久, 伊藤淳二, 三上襄, 城始勇

日本生薬学会年会講演要旨集 55th 188 2008.9

沖縄産海綿由来の新規ブロモピロールアルカロイドの構造

荒木敦, 安田鉄郎, 久保田高明, 三上襄, 小林淳一

天然有機化合物討論会講演要旨集 50th ( 50 ) 361-366 - 366 2008.9

Language：Japanese Publisher：Symposium on the chemistry of natural products

Bromopyrrole alkaloids are known to be one of the most common metabolites contained in marine sponges. During our search for bioactive substances from marine organisms, we have isolated bromopyrrole alkaloids with unique cyclic skeletons from sponges of the genus Agelas or Hymeniacidon. Recently, three new bromopyrrole alkaloids, nagelamides K, M, and N (1-3), have been isolated from an Okinawan marine sponge Agelas sp. (SS-1134). The structures and relative stereochemistry of 1〜3 were elucidated on the basis of spectroscopic data. Nagelamide K (1) is a new dimeric bromopyrrole alkaloid possessing a rare piperidinoiminoimidazolone ring with an aminoimidazole ring and a taurine unit. Nagelamide M (2) is a novel bromopyrrole alkaloid possessing an 2-amino-octahydropyrrolo[2,3-d]imidazol ring with a taurine unit, while nagelamide N (3) is a new bromopyrrole alkaloid consisting of an 2-amino-tetrahydroimidazol-4-one ring with a taurine unit and 3-(dibromopyrrole-2-carboxamido)propanoic acid moiety. Nagelamides K, M, and N (1-3) showed modest antimicrobial activity.

DOI： 10.24496/tennenyuki.50.0_361

シマサルスベリより単離した新規Lythraceaeアルカロイドの構造

久保田高明, 渡辺梢, 小林淳一, 新里孝和, 伊藤淳二, 三上襄

日本生薬学会年会講演要旨集 55th 219 2008.9

ナガサキオトギリより単離した新規フロログルシノール誘導体petiolin A‐Cの構造

田中直伸, 久保田高明, 荒木敦, 柏田良樹, 高石喜久, 三上襄, 小林淳一

日本薬学会年会要旨集 128th ( 2 ) 11 2008.3

沖縄産海綿Spongia sp.由来の新規テルペノイドMetachromin R〜Tの構造

山田美香, 高橋洋平, 久保田高明, 小林淳一

日本薬学会年会要旨集 128th ( 2 ) 11 2008.3

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