P-56 カワラタケ由来の脂肪蓄積阻害物質ternatinの単離と構造(ポスター発表の部)
スポンサーリンク
概要
- 論文の詳細を見る
Mushrooms have been widely used as health food and medicine, from which many kinds of bioactive compounds have been isolated. Recently, we found that the aqueous ethanol extract of bracket fungus Coriolus versicolor suppressed fat accumulation against 3T3-L1 murine adipocytes. Guided by this bioassay, a highly N-methylated cyclic heptapeptide (-)-ternatin (1) has been isolated. This compound showed significant inhibitory effect of fat accumulation (EC_<50>=0.14μg/mL). The planar structure of 1 was determined to be cyclo [-Ile^1-(NMe)Ala^2-(NMe)Leu^3-Leu^4-(NMe)Ala^5-(NMe)Ala^6-β-OH-Leu^7-] by the analysis of 2D-NMR (COSY and HMBC) spectra. ROESY spectrum analysis of 1 and HPLC analysis of its hydrolyzed products confirmed the absolute stereochemistry of amino acids composed of 1 except for (NMe)Ala^5-(NMe)Ala^6 and Ile^1 moieties. ROESY spectrum and HPLC analysis suggested that L-(NMe)Ala^5-D-(NMe)Ala^6 or D-(NMe)Ala^5-L-(NMe)Ala^6 and D-Ile^1 or D-allo-Ile^1 can be considered as possible stereoisomers, respectively. To confirm their stereochemistry, synthetic studies of (-)-ternatin (1) were carried out. Fmoc-β-OBn-D-Leu was prepared from isobutyraldehyde in 8 steps, followed by solid-phase peptide synthesis (SPPS) and cleavage of resin afforded linear heptapeptide. Cyclization and removement of Bn group gave cyclic heptapeptide 1a-1c. Comparison of ^1H NMR data between natural ternatin (1) and synthetic stereoisomers 1a-1c confirmed that the absolute stereochemistry of natural 1 was identical to that of 1c. Bisabolol oxide-A glucoside (2), isolated from a chamomile Matricaria chamomilla, also showed inhibitory effect of fat accumulation (EC_<50>=16.5μg/mL). The strucutre of 2 was determined by detailed analysis of 2D-NMR (COSY, HMBC and NOESY) spectra. Futher studies on the biological activities of 1 and 2 are in progress.
- 天然有機化合物討論会の論文
- 2005-09-15
著者
-
北 将樹
名大物質国際研
-
上村 大輔
名大院理
-
山田 薫
慶応大院理工
-
山田 薫
名大院理
-
北 将樹
名大院理
-
大野 智弘
(株)ファンケル中央研究所
-
下川 賢一郎
名大院理
-
Kita Masaki
Research Center for Materials Science
-
間島 いつか
名大院理
-
浅井 章子
名大院理
-
大野 美季
名大院理
-
大野 智弘
ファンケル中央研究所
-
Kita Masaki
Research Center For Materials Science Nagoya University
-
Uemura Daisuke
Department Of Chemistry Graduate School Of Science
-
Uemura Daisuke
Graduate School Of Science And Institute For Advanced Research Nagoya University
-
Uemura Daisuke
Faculty Of Liberal Arts Shizuoka University
-
上村 大輔
名古屋大学大学院理学研究科
-
Uemura Daisuke
Fancl Res. Inst. Fancl Corp.
-
Kitamura Makoto
Department Of Chemistry Graduate School Of Science Nagoya University
関連論文
- 31 食虫動物トガリネズミの麻酔物質(口頭発表の部)
- 99(P46) パリトキシンNMRスペクトルの完全帰属(ポスター発表の部)
- 70(P49) 沖縄産ヤコウガイ内臓の有毒成分(ポスター発表の部)
- 104(P51) 骨粗鬆症抑制作用物質Norzoanthamineの構造活性相関(ポスター発表の部)
- 14 生物活性海洋アルカロイド,ハリクロリン,ピンナ酸,およびノルゾアンタミン類の構造(口頭発表の部)
- 2 オニヒトデの摂餌刺激物質(口頭発表の部)
- 座談会 30年後に花開く新しい化学の姿を考える 化学の枠を越える新しい化学
- 2 海洋渦鞭毛藻由来の生物活性ポリオール類の単離および新分解反応を用いた構造決定法(口頭発表の部)
- 2 海洋共生藻由来の超炭素鎖有機分子の構造と機能(口頭発表の部)
- 10 サンゴ幼生に作用する無節サンゴモの他感作用物質(口頭発表の部)
- 25 新β-ラクトン抗生物質オキサゾロマイシンの構造
- P-75 (-)-テルナチンの脂肪蓄積阻害作用機序解明に向けた生物有機化学的研究(ポスター発表の部)
- 36 サンゴの生態に関与する生物活性物質(口頭発表の部)
- 64(P-21) 沖縄産二枚貝の超微量毒性物質pinnatoxin類とpteriatoxin類のナノモル構造決定(ポスター発表の部)
- 64(P-45) 沖縄産海洋生物の成分研究 : ウニ受精卵の第一卵割を阻害する物質を中心に(ポスター発表の部)
- 未解明生物現象の化学 (特集 これからの化学技術を読む)
- 64(P31) 放線菌由来の生物活性リポペプチド、アマミスタチンA、Bの構造(ポスター発表の部)
- 21 チロシンホスファターゼ阻害剤開発を志向したテトロン酸ライブラリーの構築 : RK-682の汎用合成法の開発とその構造活性相関(口頭発表の部)
- 52 クロイソカイメンの抗腫瘍性物質ハリコンドリン類の構造
- 89 オカダ酸の構造活性相関(ポスター発表の部)
- 27 イワタイゲキのジテルペン類の構造
- 84(P16) バンコマイシン耐性菌(VRE)に有効なマルチバレントポリマーの合成(ポスター発表の部)
- 12 パリトキシン分子形状の直接観察 : 放射光X線小角散乱測定による水溶液中配座の研究(口頭発表の部)
- Interaction of Starfish Embryonic Cells with the Complex of Okadaic Acid and Monoclonal Antibody Specific to Okadaic Acid
- Effects of Okadaic Acid on Embryonic Development of the Starfish Asterina pectinifera
- P-45 カリウドバチ毒液の化学成分と生物活性(ポスター発表の部)
- P-2 STUDY OF THE LETHAL VENOM FROM THE SHORT-TAILED SHREW Blarina brevicauda
- Purification and characterisation of blarinasin, a new tissue kallikrein-like protease from the short-tailed shrew Blarina brevicauda: comparative studies with blarina toxin
- Blarina toxin, a mammalian lethal venom from the short-tailed shrew Blarina brevicauda : Isolation and characterization
- P-56 カワラタケ由来の脂肪蓄積阻害物質ternatinの単離と構造(ポスター発表の部)
- 12(B-8) 共生微細藻類の産生する超炭素鎖有機分子に関する研究(口頭発表の部)
- 生物活性海洋アルカロイドの構造と機能
- 76 ケールの肥満細胞脱顆粒抑制作用について(肥満細胞, 好塩基球(2), 第55回日本アレルギー学会秋季学術大会)
- 未解明生物現象の化学 (特集/期待される化学研究の話題)
- Development of Chemical Substances Regulating Biofilm Formation
- Tanzawaic Acids A, B, C, and D : Inhibitors of Superoxide Anion Production from Penicillium citrinum
- Homocereulide, an Extremely Potent Cytotoxic Depsipeptide from the Marine Bacterium Bacillus cereus
- Preparation of Quinoline Hexose Analogs as Novel Chloroquine-Resistant Malaria Treatments (1). Synthesis of 4-Hydroxyquinoline-β-glucosides
- P-144 BIOORGANIC CHEMICAL STUDIES ON KARATUNGIOLS A-D, NOVEL SUPER-CARBON-CHAIN COMPOUNDS FROM THE SYMBIOTIC MARINE DINOFLAGELLATE AMPHIDINIUM SP.
- P-142 Structure of Symbiodinolide, a Super-carbon-chain Compound Isolated from the Symbiotic Dinoflagellate Symbiodinium sp.
- Synthetic Studies of Norzoanthamine. Preparation of the Diene-yne-diene Precursor of an ABC-ring Fragment
- Isolation of Tribromoacetamide from an Okinawan Alga and Biological Activities of Its Analogs
- Haterumaimides J and K, Potent Cytotoxic Diterpene Alkaloids from the Ascidian Lissoclinum Species
- Kohamaic Acids A and B, Novel Cytotoxic Sesterterpenic Acids, from the Marine Sponge Ircinia sp.
- Isolation and Structures of Attenols A and B. Novel Bicyclic Trials from the Chinese Bivalve Pinna attenuate
- ロゴマークと国際会議
- P-578 CHARACTERIZATION OF PARALYTIC SUBSTANCE FROM THE VENOM OF SPIDER WASP : Cyphononyx dorsalis
- 座談会 有機化学のブレークスルー--この10年の進歩を振り返り,その未来を語る
- 時を超える「ひと」, 「もの」, 「こころ」
- 海洋共生藻由来の超炭素鎖有機分子
- 海洋由来の生物活性物質の探索
- 生物現象に学ぶ天然物化学--生態系ダイナミズムに着目した物質検索 (〔現代化学〕創刊400号記念特集 世界をリードする日本の化学)
- P-246 SYNTHETIC STUDY OF TERPIODIENE
- Durinskiol B : A New Durinskiol Congener from the Symbiotic Marine Dinoflagellate Durinskia sp.
- Haterumadienone : A New Puupehenone Congener from an Okinawan Marine Sponge, Dysidea sp.
- Dinohydrazides A and B, Novel Hydrazides from a Symbiotic Marine Dinoflagellate
- Papillamide, a Novel Fatty Acid Amide from the Red Alga Laurencia papillosa
- Application of FITC-labeled Ternatin on Its Cellular Localization in 3T3-L1 Murine Preadipocytes
- P-412 CHEMICAL INVESTIGATION ON BIOLOGICAL ACTIVE COMPOUNDS FROM DINOFLAGELLATES
- P-397 Characterization of a Natural Inducer of Coral Larval Metamorphosis
- P-269 (-)-Ternatin, which inhibits fat accumulation against 3T3-L1 adipocytes, from the mushroom Coriolus versicolor
- P-249 FEEDING ATTRACTANTS FOR THE NECKLACE SHELL Neverita dydima, A CLAM PREDATOR
- P-224 STUDIES ON CYTOTOXIC COMPOUNDS FROM RED ALGAE WHICH OVERGROW CORALS
- Studies in Bioactive Marine Alkaloids
- Synthesis of (±)-Pinnaic Acid
- 未解明生物現象の化学(最近の天然物化学の進歩)
- Stereostructure and Bioactivities of Jolkinolide D
- Suppressive Effect of Norzoanthamine Hydrochloride on Experimental Osteroporosis in Ovariectomized Mice
- Structure-Activity Relationship of Norzoanthamine Exhibiting Significant Inhibition of Osteoporosis
- P-221 Unified Total Synthesis and Stereochemistry of Pteriatoxins A-C and Pinnatoxins B/C
- P-192 THE EFFECT OF ACCETYLATION ON THE SHAPE OF PALYTOXIN IN SOLUTION ASSESSED BY SYNCHROTRON SMALL ANGLE X-RAY SCATTERING TECHNIQUE
- 未解明生命現象 (ケミカルバイオロジー) -- (生理活性物質のケミカルバイオロジー 生物現象の不思議に迫るケミカルバイオロジー)
- Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated from Piper longum on Melanin Production in B16 Mouse Melanoma Cells
- Melanin Biosynthesis Inhibitors from Tarragon Artemisia dracunculus
- Iminium Alkaloids from Marine Invertebrates : Structure, Biological Activity, and Biogenesis
- Melanin Biosynthesis Inhibitors from Tarragon Artemisia dracunculus
- 海洋生物は生命の謎をひもとく切れもの分子の宝庫です(最先端の化学,化学だいすきクラブニュースレター)
- 30 有毒哺乳動物カモノハシ由来の神経毒に関する生物有機化学的研究(口頭発表の部)