126(P-68) 抗発ガンプロモーション活性を有するクリプトポール酸の化学(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
Cryptoporic acids A〜G have been isolated from fungi Cryptoporus volvatus, and their structures have been established by high resolution 2D-NMR techniques, X-ray analysis, and chemical degradations to have very unusual structure, albicanol bonded to isocitric acid moiety by an ether linkage. Moreover their biological activities are highly interesting, for example, superoxide anion release inhibition and anti-tumor promotion activities. A simple Williamson ether synthesis could not be applied due to instability of albicanyl bromide. Etherification using Olah and Nishizawa method could not be applied according to the presence of ester functions. Therefore, we have developed the 1,4-addition of the enolate of 20 derived from albicanol (18) to maleate and fumarate residues. We have succeeded in the first synthesis of cryptoporic acid A methyl ester (8). We have been interested in their biological activities and planned to prepare synthetic substitutes to the natural products. We first intended to prepare isocitric acid with the same stereochemistry as natural products. Then, fatty acids were attached to isocitric acid and biological activities of these esters have been evaluated. Because the natural products exhibit strong superoxide release inhibition activities, these compounds were similarly subjected to the same tests. Among those tested, compound 34 was the most effective (IC_<50>: 0.39μM). The malic acid derivatives are 10 times more effective than isocitric acid derivatives. The linoleic acid derivatives were more than twice as strong as linolenic acid derivatives. Compounds 27 and 28 were further subjected to inhibition tests of TNFα's release with okadaic acid by anti-tumor promoters on BALB/3T3 cells. Both compounds are as strong as sarcophytol A (36) and cryptoporic acid E (4). Therefore, it is very interesting to note that the relative positions of hydrophilic and lipophilic parts are very important, and that the lipophilic part can be substituted by fatty acids to show anti-tumor promoter activity.
- 天然有機化合物討論会の論文
- 2000-10-01
著者
-
通 元夫
徳島文理大薬
-
橋本 敏弘
徳島文理大・薬
-
浅川 義範
徳島文理大・薬
-
Hashimoto T
Faculty Of Pharmaceutical Sciences Hokuriku University
-
橋本 忠
北陸大・薬
-
浅川 義範
徳島文理大学薬学部
-
中島 勝幸
徳島文理大薬
-
宗野 真和
徳島文理大薬
-
宗野 陽子
徳島文理大薬
-
濱田 典子
徳島文理大薬
-
宗野 真和
徳島文理大学薬学部
-
Hashimoto T
Hokuriku Univ. Kanazawa Jpn
-
Hashimoto Toshihiro
Fac. Of Pharmaceutical Sciences Tokushima Bunri Univ.
-
浅川 義範
徳島文理大 薬
-
通 元夫
徳島文理大学薬学部
-
通 元夫
徳島文理大・薬
関連論文
- Synthesis of Thyrotropin-Releasing Hormone-Related Peptides Using N^α-tert-Bytyloxycarbonyl-ω-(N-tert-butyloxycarbonylcarbamoyl)-α-amino Acids
- P-7 フラノエレモフィラン化合物を生産しないLigularia数種の中国横断山脈地域における多様性(ポスター発表の部)
- エゾシロアミタケHaploporus odorusからの新規hoploporic acid類 : 有機化学・天然物化学
- Structure-Activity Relationships of Neuromedin U. V. Study on the Stability of Porcine Neuromedin U-8 at the C-Terminal Asparagine Amide under Mild Alkaline and Acidic Conditions
- A3 トロンビンレセプターが介在する血管内皮細胞プロテオグリカン合成の調節
- β-アミロイドペプチド(β25-35)のダンシルラベル体による凝集と蛍光特性変化の解析
- Hydrolytic Cleavage of Pyroglutamyl-Peptide Bond. I. The Susceptibility of Pyroglutamyl-Peptide Bond to Dilute Hydrochloric Acid
- Structure-Activity Relationships of Neuromedin U. II. Highly Potent Analogs Substituted or Modified at the N-Terminus of Neuromedin U-8
- Structure-Activity Relationships of Neuromedin U. I. Contractile Activity of Dog Neuromedin U-Related Peptides on Isolated Chicken Crop Smooth Muscle
- Contractile Activity of Porcine Neuromedin U-25 and Various Neuromedin U-Related Peptide Fragments on Isolated Chicken Crop Smooth Muscle
- Agonistic and Antagonistic Activities of Neuromedin U-8 Analogs Substituted with Glycine or D-Amino Acid on Contractile Activity of Chicken Crop Smooth Muscle Preparations
- Structure-Activity Relationships of Rat Neuromedin U for Smooth Muscle Contraction
- Synthesis of Head Activator (HA)-Related Peptides and Development of HA-Radioimmunoassay(Organic,Chemical)
- PROPERTIES OF N^α, N^-DI- TERT-BUTYLOXYCARBONYL-ω-CARBAMOYL-α-AMINO ACIDS AND DIRECT SYNTHESIS OF PROTECTED HOMOGLUTAMIC ACID DERIVATIVES
- URETHANE TYPE PROTECTING GROUPS FOR CARBOXAMIDE IN PEPTIDE CHEMISTRY
- Active Peptides on Smooth Muscle in the Skin of Bombina orientalis BOULENGER and Characterization of a New Bradykinin Analogue
- Hydrolytic Cleavage of Pyroglutamyl-peptide Bond. V. Selective Removal of Pyroglutamic Acid from Biologically Active Pyroglutamylpeptides in High Concentrations of Aqueous Methanesulfonic Acid
- Regioselective Hydrolytic Cleavage of N-Terminal Myristoyl-peptide
- Regioselective Hydrolysis of Formyl-peptide in Aqueous Methanesulfonic Acid
- 27-04-08 Kaurene diterpene の dual specific 型抗癌剤としての有用性
- HDL産生を促進するLXRαパーシャルアゴニスト/ LXRβアンタゴニスト riccardin C の発見
- 20-P3-532 徳島文理大学における早期体験学習の現状と評価 : 1年次生・施設指導者のアンケート調査を基に(薬学教育(その他),来るべき時代への道を拓く)
- コケ類の環状ビスビベンジル類の構造と生理活性および全合成
- THE ABSOLUTE STRUCTURES OF NEW 1β-HYDROXY-SACCULATANE-TYPE DITERPENOIDS WITH PISCICIDAL ACTIVITY FROM THE LIVERWORT PELLIA ENDIVIIFOLIA
- Nitric Oxide Synthesis in Murine Peritoneal Macrophages by Fungal β-Glucans
- P-21 数種の中国産キク科Cremanthodium属植物の成分と塩基配列(ポスター発表の部)
- P-3 中国産キク科Ligularia kanaitzensis,Ligularia vellerea,Ligularia subspicataおよびLigularia lamarumの化学成分と遺伝子の多様性(ポスター発表の部)
- キク科リグラリア属植物の多様性
- P-7 中国横断山脈地域における4種のLigularia属植物の種内多様性(ポスター発表の部)
- 45 苔類の生理活性環状ビスビベンジルおよびテルペノイド
- Application of LC-NMR for Characterization of Rat Urinary Metabolites of Zonampanel Monohydrate (YM872)
- 100(P-57) スフェノロバン型ジテルペン三種の全合成と絶対配置 : オレフィンメタセシス反応を用いる三置換二重結合を含む七員環の効率的合成(ポスター発表の部)
- 126(P-68) 抗発ガンプロモーション活性を有するクリプトポール酸の化学(ポスター発表の部)
- FUSICORRUGATOL FROM THE VENEZUELAN LIVERWORT PLAGIOCHILA CORRUGATA
- LTQ FT MS Accurate Mass and SRM Data Dependent Exclusion MSn Measurements for Structure Determination of FK228 and Its Metabolites (BMS特集号)
- Effect of Nilvadipine, a Dihydropyridine Calcium Antagonist, on Cytochrome P450 Activities in Human Hepatic Microsomes (Biochemistry/Molecular Biology)
- Effect of Cefixime and Cefdinir, Oral Cephalosporins, on Cytochrome P450 Activities in Human Hepatic Microsomes(Biochemistry/Molecular Biology)
- Inhibitory activity of nitric oxide production in RAW 264.7 cells of daldinals A-C from the fungus Daldinia childiae and other metabolites isolated from inedible mushrooms
- Hydnellins A and B, Nitrogen-Containing Terphenyls from the Mushrooms Hydnellum suaveolens and Hydnellum geogerirum
- Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi(Molecular and Cell Biology)
- Pregnane-Type Steroids from the Inedible Mushroom Thelephora terrestris
- Tyromycic Acids F and G: Two New Triterpenoids from the Mushroom Tyromyces fissilis
- Curtisians M-Q: Five Novel p-Terphenyl Derivatives from the Mushroom Paxillus curtisii
- A Novel ent-Kaurane Diterpenoid from the Croton tonkinensis GAGNEP
- Two Novel Ravenelones from the Edible Mushroom Pulveroboletus ravenelii
- 49 トリテルペンの骨格転位反応に関する研究
- P-5 フェネチルアミンを用いる数種の苔類セスキテルペンのキラル合成 : キラル反応生成物の絶対配置とCDスペクトル(ポスター発表の部)
- STRUCTURES OF DALDINING A〜C, THREE NOVEL AZAPHILONE DERIVATIVES FROM ASCOMYCETOUS FUNGUS KALKINIA CONCENTRICA
- THREE NOVEL POLYACETYLENE TRIGLYCERIDES, LYCOGARIDES A-C, FROM THE MYXOMYCETES LYCOGALA EPIDENDRUM
- STRUCTURES OF A NOVEL BINAPHTHYL AND THREE NOVEL BENZOPHENONE DERIVATIVES WITH PLANT-GROWTH INHIBITORY ACTIVITY FROM THE FUNGUS DALDINIA CONCENTRICA
- STRUCTURES AND TOTAL SYNTHESIS OF TWO NOVEL BIS(BIBENZYLS), PALEATINS A AND B, FROM THE LIVERWORT MARCHANTIA PALEACEA VAR. DIPTERA
- 46 苔類ウスバゼニゴケおよびトサハネゴケより単離された新規大環状ビスビベンジル化合物の構造(口頭発表の部)
- 61 真性粘菌マメホコリの新規ポリアセチレントリグリセリドおよびインドロカルバゾール系化合物の構造(ポスター発表の部)
- 11 変形菌類マメホコリの新規ポリアセチレントリグリセライドおよびジベンゾカルバゾール誘導体の構造(口頭発表の部)
- THE STEREOCHEMISTRY OF REDUCTIVE CARBOXYLATION PRODUCTS OF (1S, 8R)-1-METHYL-5,6,7,8-TETRAHYDROINDAN-5-ONE
- サルノコシカケ科ヒトクチタケの苦味セスキテルペノイド
- Eremopetasitenin A3 and 8-Oxoeremophil-6-en-12-oic Acid from Petasites japonicus ssp. giganteus
- Development of Neuromedin U Agonist with Specifically Potent Contractile Activity on Rat Uterus Smooth Muscle
- 68(P-55) アブラムシに含まれる色素の研究(ポスター発表の部)
- Isolation, Synthesis and Biological Activity of Grifolic Acid Derivatives from the Inedible Mushroom Albatrellus dispansus
- [1-^C]Octanoate as a PET Tracer for Studying Ischemic Stroke : Evaluation in a Canine Model of Thromboembolic Stroke with Positron Emission Tomography
- 蘚苔類の辛味, 苦味および甘味物質
- 蘚苔類の香気物質
- 蘚苔類及び非食菌類の生理活性成分
- 67(P43) ウスバゼニゴケ科苔類から得られるフェノール性化合物(ポスター発表の部)
- P-24 5種の子嚢菌類に含まれる新規Cytochalasin類、Azaphilone類および芳香族化合物の構造(ポスター発表の部)
- Studies on Cardiac Ingredients of Plants. XIII : Chemical Modification of Gitoxin to Cardiotonic Compounds without Vascular Contractile Effect
- Determination of D- and L-enantiomers of methionine and [^2H_3]methionine in plasma by gas chromatography-mass spectrometry
- Simultaneous determination of methionine and total homocysteine in human plasma by gas chromatography-mass spectrometry
- Kinetics of Intramolecular Acyl Migration of 1β-O-Acyl Glucuronides of(R)-and(S)-2-Phenylpropionic Acids
- Gas chromatographic-mass spectrometric determination of α-ketoisocaproic acid and [^2H_7] α-ketoisocaproic acid in plasma after derivatization with N-phenyl-1, 2-phenylenediamine
- Stereoselective Internal Acyl Migration of 1β-O-Acyl Glucuronides of Enantiomeric 2-Phenylpropionic Acids
- Preliminary evaluation of [1-^C]octanoate as a PET tracer for studying cerebral ischemia: A PET study in rat and canine models of focal cerebral ischemia
- Biotransformation of hinesol Isolated from the Crude Drug Atractylodes Iancea by Aspergillus niger and Aspergillus cellulosae
- 2 苔類の産する大環状ビスビベンジル類の構造とNMR
- 3,4-縮合5,6-Dihydro-2H-pyran誘導体に関する研究(第1報)Dihydrofuropyran誘導体および1位置換Isochroman誘導体の新合成法
- 3,4-縮合5,6-Dihydro-2H-pyran誘導体の新合成法
- 66 苔類コハネゴケに含まれる新規フシコカン型ジテルペノイドの単離と構造
- 17 キラル異方性試薬による直鎖状アルコールおよびカルボン酸の絶対配置およびコンホメーション解析(口頭発表の部)
- Isolation and Structures of New Cyclomyltaylane and ent-Chamigrane-Type Sesquiterpenoids from the Liverwort Reboulia hemishaerica and Their Biotransformation by the Fungus Aspergillus niger
- Biotransformation of Aristolane- and 2,3-Secoaromadendrane-Type Sesquiterpenoids Having a 1,1-Dimethylcyclopropane Ring by Chlorella fusca var. vacuolata, Mucor Species, and Aspergillus niger
- Highly Efficient Production of Nootkatone, the Grapefruit Aroma from Valencene, by Biotransformation(Communications to the Editor)
- Biotransformation of Citrus Aromatics Nootkatone and Valencene by Microorganisms
- Investigations into Biochemical Changes of Genetic Hypertensive Rats Using ^1H Nuclear Magnetic Resonance-Based Metabonomics
- Hydrolytic Cleavage of Pyroglutamyl-Peptide Bond. IV. Highly Selective Cleavage of Thyrotropin Releasing Hormone (TRH) in Aqueous Methanesulfonic Acid
- Structure-Activity Relationships of Neuromedin U.IV. Absolute Requirement of the Arginine Residue at Position 7 of Dog Neuromedin U-8 for Contractile Activity
- Sesquiterpenoids Isolated from Eupatorium glehnii. Isolation of Guaiaglehnin A, Structure Revision of Hiyodorilactone B, and Genetic Comparison
- Total Synthesis and Cytotoxicity of (+)- and (-)-Goniodiol and 6-epi-Goniodiol. Construction of α,β-Unsaturated Lactones by Ring-Closing Metathesis
- Preparation of Seven-Membered Carbocycles Using Ring-Closing Metathesis Reaction and Application to Syntheses of Tormesol and Cyathane Skeleton
- Seven Germacranolides, Eupaglehnins A, B, C, D, E, and F, and 2 α-Acetoxyepitulipinolide from Eupatorium glehni
- Analysis of [^2H_7]methionine, [^2H_4]methionine, methionine, [^2H_4]homocysteine and homocysteine in plasma by gas chromatography-mass spectrometry to follow the fate of administered [^2H_7]methionine
- Two New Chlorine-containing Germacranolides,Eupaglehnins E and F from Eupatorium glehni
- Biotransformation of Terpenoids from the Crude Drugs and Animal Origin by Microorganisms
- Tissue Selective Contractile Activity of Neuromedin U Analogs on Isolated Smooth Muscles
- 86(PA3-6) 苔類コハネゴケの新規大環状ビスビベンジルの構造(ポスター発表の部)
- FIVE NEW DIARYLHEPTANOIDS FROM THE MALE FLOWERS OF ALNUS SIEBOLDIANA
- キク科リグラリア属植物の多様性(レーダー)
- 中国横断山脈でオーミックスペースを齧る
- A metabonomic study of biochemical changes characteristic of genetically hypertensive rats based on ^1H NMR spectroscopic urinalysis
- 化学成分からみたヌエゴケMizutania riccardioidesの系統学的位置(シンポジウム:ヌエゴケに迫る,第30回日本蘚苔類学会大分大会)