Identification and specific makers of abnormal bile acids excreted in inborn errors of bile acid biosynthesis

• Project/Area Number: 21550091
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Analytical chemistry
• Research Institution: Nihon University
• Principal Investigator: IIDA Takashi 日本大学, 文理学部, 教授 (60060125)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 生体分子 / 異常胆汁酸代謝産物 / LC/ESI-MS/MS / 先天性胆汁酸代謝異常症 / Δ^4-3-オキソ-ステロイド-5β-レダクターゼ欠損症 / 二次異常代謝産物 / ステロイド多重抱合体 / LC-MS / 3β-HSD/HIS欠損症 / ニーマン-ピック病C型 / LC/MS / NPC_1 / LC / MS

Research Abstract

The synthesis of bile salts from cholesterol is a complex biochemical pathway involving at least 16 enzymes. Most inborn errors of bile acid biosynthesis result in excessive formation of intermediates and/or their metabolites that accumulate in blood and are excreted in part in urine. Early detection is important as oral therapy with bile acids results in improvement. In the past, these intermediates in bile acid biosynthesis have been detected in neonatal blood or urine by screening with FAB-MS followed by detailed characterization using GC-MS. Both methods have proved difficult to automate, and currently most laboratories screen candidate samples using LC-MS/MS. Here, we describe a new, simple and sensitive analytical method for the identification and characterization of 39 conjugated and unconjugated bile acids, including Δ^-3-oxo- and Δ^<4, 6>-3-oxo-bile acids(markers for Δ^4-3-oxo-steroid 5β-reductase deficiency), using liquid chromatography-electrospray ionization tandem mass spectrometry(LC/ESI-MS/MS). In this procedure, a concentrated, desalted urinary sample(diluted with ethanol) is injected directly into the LC-ESI-MS/MS, operated with ESI and in the negative ion mode ; quantification is obtained by selected reaction monitoring(SRM). To evaluate the performance of our new method, we compared it to a validated method using GC-MS, in the analysis of urine from two patients with genetically confirmed Δ^4-3-oxo-steroid-5β-reductase deficiency as well as a third patient with an elevated concentration of abnormal conjugated and unconjugated Δ^4-3-oxo-bile acids. The Δ^4-3-oxo-bile acids concentration recovered in three patients with 5β-reductase deficiency were 48.8, 58.9, and 49.4μmol/mmol Creatinine, respectively by LC/ESI-MS/MS.

Research Products

• [Journal Article] Detection ofΔ^4-3-oxo-steroid 5β-reductase deficiency by LC-ESI-MS/MS measurement of urinary bile acids (2012)
  • Author(s): A. Muto, T. Iida, A. F. Hofmann, H. Nittono
  • Journal Title: J. Chromatogr. B Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] Comparative Cytotoxic Activities of the Propanamide and Spiro-γ-lactone Derivatives ofΔ^<14>-17α-and 17β-Estradiol Stereoisomers Against Human Cell Lines (2012)
  • Author(s): H. Tamegai, S. Ogawa, H. Konishi, A. Takagi, T. Matsuzaki, T. Iida
  • Journal Title: Proc. Instit. Nat. Sci. Nihon Univ Volume: No.47 Pages: 497-501
  • Peer Reviewed
• [Journal Article] Monoterpene Glucosides from Ziziphora clinopodioides(Labiatae) (2012)
  • Author(s): M. Furukawa, N. Oikawa, T. Imohata, M. Makino, S. Ogawa, T. Iida, Y. Fujimoto, S. Kitanaka
  • Journal Title: Chem. Pharm. Bull Volume: Vol.60, No.3 Pages: 397-401
  • NAID: 130001852428
  • Peer Reviewed
• [Journal Article] Synthesis of 3-Sulfates of S-Acyl Glutathione Conjugated Bile Acids and their Biotransformation by a Rat Liver Cytosolic Fraction (2012)
  • Author(s): K. Mitamura, N. Hori, S. Mino, T. Iida, A. F. Hofmann, S. Ikegawa
  • Journal Title: Chem. Phys. Lipids Volume: Vol.165, No.1 Pages: 261-269
  • Peer Reviewed
• [Journal Article] Identification of S-Acyl Glutathione Conjugates of Bile Acids in Human Bile by means of LC/ESI-MS (2011)
  • Author(s): K. Mitamura, N. Hori, T. Iida, M. Suzuki, T. Shimizu, H. Nittono, K. Takaori, H. Takikawa, A. F. Hofmann, S. Ikegawa
  • Journal Title: Steroids Volume: Vol.76, No.12 Pages: 1609-1614
  • Peer Reviewed
• [Journal Article] Studies on the Constituents of Lagochilus leiacanthus(Labiate) (2011)
  • Author(s): M. Furukawa, H. Suzuki, M. Makino, S. Ogawa, T. Iida, Y. Fujimoto
  • Journal Title: Chem. Pharm. Bull Volume: Vol.59, No.12 Pages: 1535-1540
  • Peer Reviewed
• [Journal Article] Synthesis of 3-and 21-Monosulfates of [2, 2, 3β, 4, 4-^2H_5]-Tetrahydrocorticosteroiuds in the 5β-Series as Internal Standards for Mass Spectrometry (2011)
  • Author(s): S. Ikegawa, K. Nagase, T. Mabuchi, R. Okihara, M. Hasegawa, T. Minematsu, T. Iida, K. Mitamura
  • Journal Title: Steroids Volume: Vol.76 Pages: 1232-1240
  • Peer Reviewed
• [Journal Article] Biliary Bile Acids in Birds of the Cotingidae Family : Taurine-Conjugated(24R, 25R)-3α, 7α, 25-Trihydroxy-5β-cholestan-27-oic Acid and Two epimers(25R and 25S) of 3α, 7α-Dihydroxy-5β-cholestan-27-oic Acid (2011)
  • Author(s): L. R. Hagey, T. Iida, S. Ogawa, Y. Adachi, M. Une, K. Mushiake, M. Maekawa, M. Shimada, N. Mano, and A. F. Hofmann
  • Journal Title: Steroids Volume: Vol.76 Pages: 1126-1135
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of the(25R)-and(25S)-Epimers of 3α, 7α, 12α-Trihydroxy-5α-cholestan-27-oic Acid as well as Their Corresponding Glycine and Taurine Conjugates (2011)
  • Author(s): S. Ogawa, K. Mitamura, S. Ikegawa, M. D. Krasowski, L. R. Hagey, A. F. Hofmann, T. Iida
  • Journal Title: Chem. Phys. Lipids Volume: Vol.164 Pages: 368-377
  • Peer Reviewed
• [Journal Article] 液体クロマトグラフィー/質量分析法によるヒト胆汁中グルタチオン抱合型胆汁酸の同定 (2011)
  • Author(s): 池川繁男、堀直宏、三田村邦子、飯田隆、鈴木光幸、清水俊明、入戸野博、高折恭一
  • Journal Title: 胆膵の病態生理 Volume: Vol.27, No.1 Pages: 23-27
  • Peer Reviewed
• [Journal Article] PFIC 1型および2型における肝機能検査値と尿中胆汁酸分析 (2011)
  • Author(s): 入戸野博、武藤晃奈、武井一、清水俊明、木村昭彦、窪田満、虹川大樹、依藤亨、清水泰岳、有馬透、村井毅、黒澤隆夫、藤間貞彦、飯田隆
  • Journal Title: 日本小児栄養消化器肝臓学会誌 Volume: vol.25, No.1 Pages: 6-12
  • NAID: 10029384315
  • Peer Reviewed
• [Journal Article] Characterization of Non-Enzymatic Acylation of Amino or Thiol Groups of Binucleophiles by the Acyl-Adenylate or Acyl-CoA Thioester of Cholic Acid (2011)
  • Author(s): K. Mitamura, E. Aoyama, T. Sakai, T. Iida, A. F. Hofmann, S. Ikegawa
  • Journal Title: Anal. Bioanal. Chem Volume: Vol.400 Pages: 2253-2259
  • Peer Reviewed
• [Journal Article] Synthesis of the 3-Sulfates of-N-acetylcysteine Conjugated Bile Acids(BA-NACs) and their Transient Formation from BA-NACs and Subsequent Hydrolysisby a Rat Liver Cytosolic Fraction as Shown by Liquid Chromatiography/Electrospray Ionization-Mass Spectrometry (2011)
  • Author(s): K. Mitamura, T. Sakai, R. Nakai, T. Wakamiya, T. Iida, A. F. Hofmann, S. Ikegawa
  • Journal Title: Anal. Bioanal. Chem Volume: Vol.400 Pages: 1061-2072
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of the 17-Propanamide Derivatives of StereoisomericΔ^<14>-17α-and 17β-Estradiols : Potential 17β-Hydroxysteroid Dehydrogenase Inhibitors (2011)
  • Author(s): T. Iida, S. Ogawa, H. Tamegai, Y. Adachi, H. Saito, S. Ikegawa, H. Konishi, A. Takagi, T. Matsuzaki
  • Journal Title: Chem. Phys. Lipids Volume: Vol.164, No.2 Pages: 106-112
  • Peer Reviewed
• [Journal Article] Identification of Bile Acid S-Acyl Glutathione Conjugates in Rat Bile by Liquid Chromatography/Electrosperay Ionization-Linear Ion Trap Mass Spectrometry (2011)
  • Author(s): K. Mitamura, N. Hori, T. Iida, A. F. Hofmann, S. Ikegawa
  • Journal Title: Steroids Volume: Vol.76, No.1 Pages: 68-68
  • Peer Reviewed
• [Journal Article] ROMP Polymer-Based Antimicrobial Films Repeatedly Chargeable with Silver Ions (2011)
  • Author(s): S. Takano, H. Tamegai, T. Itoh, S. Ogata, H. Fujimori, S. Ogawa, T. Iida, Y. Wakatsuki
  • Journal Title: Reactive & Functional Polymers Volume: Vol.71 Pages: 195-203
  • Peer Reviewed
• [Journal Article] Synthesis of 3-and 21-monosulfates of [2,2,3β,4,4-^2H_5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry (2011)
  • Author(s): S.Ikegawa, K.Nagae, T.Mabuchi, R.Okihara, M.Hasegawa, T.Minematsu, T.Iida, K.Mitamura
  • Journal Title: Steroids Volume: 76巻 Pages: 1232-1240
  • Peer Reviewed
• [Journal Article] Studies on the Constituents of Lagochilus leiacanthus (Labiatae) (2011)
  • Author(s): M.Furukawa, H.Suzuki, M.Makino, S.Ogawa, T.Iida, Y.Fujimoto
  • Journal Title: Chem.Pharm Bull. Volume: 59巻 Pages: 1535-1540
  • NAID: 130001852128
  • Peer Reviewed
• [Journal Article] Identification of S-acyl glutathione conjugates of bile acids in human bile by means of LC/ESI-MS (2011)
  • Author(s): K.Mitamura, N.Hori, T.Iida, M.Suzuki, T.Shimizu, H.Nittono, K.Takaori, H.Takikawa, A.F.Hofmann, S.Ikegawa
  • Journal Title: Steroids Volume: 76巻 Pages: 1609-1614
  • Peer Reviewed
• [Journal Article] Identification of glutathione conjugates of bile acids in human bile by liquid chromatography/mass spectrometry (2011)
  • Author(s): S.Ikegawa, N.Hori, K.Mitamura, T.Iida, M.Suzuki, T.Shimizu, H.Nittono, K.Takaori
  • Journal Title: 胆膵の病態生理 Volume: 27巻 Pages: 23-27
  • Peer Reviewed
• [Journal Article] Biliary bile acids in birds of the Cotingidae family : taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy-5β-cholestan-27-oic acid (2011)
  • Author(s): L.R.Hagey, T.Iida, S.Ogawa, Y.Adachi, M.Une, K.Mushiake, M.Maekawa, M.Shimada, N.Mano, A.F.Hofmann
  • Journal Title: Steroids Volume: 76巻 Pages: 1126-1135
  • Peer Reviewed
• [Journal Article] Characterization of non-enzymatic acylation of amino or thiol groups of bionucleophiles by the acyl-adenylate or acyl-CoA thioester or cholic acid (2011)
  • Author(s): K.Mitamura, E.Aoyama, T.Sakai, T.Iida, A.F.Hofmann, S.Ikegawa
  • Journal Title: Anal.Bioanal.Chem. Volume: 400巻 Pages: 2253-2259
  • Peer Reviewed
• [Journal Article] PFIC1型および2型における肝機能検査値と尿中胆汁酸分析 (2011)
  • Author(s): 入戸野博・飯田隆, 他13名
  • Journal Title: 日本小児栄養消化器肝臓学会誌 Volume: 25巻 Pages: 6-12
  • NAID: 10029384315
  • Peer Reviewed
• [Journal Article] Chemical synthesis of the (25R)-and (25S)-epimers of 3αa,7α,12α-trihydroxy-5α-cholestan-27-oic acid as well as their corresponding glycine and taurine conjugates (2011)
  • Author(s): S.Ogawa, K.Mitamura, S.Ikegawa, M.D.Krasowski, L.R.Hagey, A.F.Hofmann, T.Iida
  • Journal Title: Chemistry & Physics of Lipids Volume: 164巻 Pages: 368-377
  • Peer Reviewed
• [Journal Article] Synthesis of the 3-sulfates of N-acetylcysteine conjugated bile acids (BA-NACs) and their transient formation from BA-NACs and subsequent hydrolysis by a rat liver cytosolic fraction as shown by liquid chromatography/electrospray ionization-mass spectrometry (2011)
  • Author(s): K.Mitamura, T.Sakai, R.Nakai, T.Wakamiya, T.Iida, A.F.Hofmann, S.Ikegawa
  • Journal Title: Anal.Bioanal.Chem. Volume: 400巻 Pages: 2061-2072
  • Peer Reviewed
• [Journal Article] ROMP polymer-based antimicrobial films repeatedly chargeable with silver ions (2011)
  • Author(s): S.Takano, H.Tamegai, T.Itoh, S.Ogata, H.Fujimori, S.Ogawa, T.Iida, Y.Wakatsuki
  • Journal Title: Reactive & Functional Polymers Volume: 71巻 Pages: 195-203
  • Peer Reviewed
• [Journal Article] Chemical synthesis of the 17-propanamide derivatives of stereoisomeric Δ^<14>-17α-and 17β-estradiols : potential 17β-hydroxysteroid dehydrogenase inhibitors (2011)
  • Author(s): T.Iida, S.Ogawa, H.Tamegai, Y.Adachi, H.Saito, S.Ikegawa, H.Konishi, A.Takagi, T.Matsuzaki
  • Journal Title: Chemistry & Physics of Lipids Volume: 164巻 Pages: 106-112
  • Peer Reviewed
• [Journal Article] Identification of bile acid S-acyl glutathione conjugates in rat bile by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry (2011)
  • Author(s): K.Mitamura, N.Hori, T.Iida, A.F.Hofmann, S.Ikegawa
  • Journal Title: Steroids Volume: 76巻 Pages: 68-77
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of the 17-Propanamide Derivatives of Stereoisomeric △^<14>-17α-and 17β-Estradiols : Potential 17β-Hydroxysteroid Dehydrogenase Inhibitors (2011)
  • Author(s): T.Iida, S.Ogawa, H.Tamegai, Y.Adachi, H.Saito, S.Ikegawa, H.Konishi, A.Takagi, T.Matsuzaki
  • Journal Title: Chem.Phys.Lipids Volume: 164巻 Pages: 106-112
  • Peer Reviewed
• [Journal Article] Identification of Bile Acid S-Acyl Glutathione Conjugates in Rat Bile by Liquid Chromatography/Electrosperay Ionization-Linear Ion Trap Mass Spectrometry (2011)
  • Author(s): K.Mitamura, N.Hori, T.Iida, A.F.Hofmann, S.Ikegawa
  • Journal Title: Steroids Volume: 76巻 Pages: 68-77
  • Peer Reviewed
• [Journal Article] ROMP Polymer-Based Antimicrobial Films Repeatedly Chargeable with Silver Ions (2011)
  • Author(s): S.Takano, H.Tamegai, T.Itoh, S.Ogata, H.Fujimori, S.Ogawa, T.Iida, Y.Wakatsuki
  • Journal Title: React.Funct.Polymers Volume: 71巻 Pages: 195-203
  • Peer Reviewed
• [Journal Article] Hepatobiliary Disposition of 3α, 6α, 7α, 12α-Tetrahydroxy-cholanoyl Taurine : A Substrate for Multiple Canalicular Transporters (2010)
  • Author(s): V. Megaraj, T. Iida, P. Jungsuwadee, A. F. Hofmann, M. Vore
  • Journal Title: Drug Metab. & Disposit Volume: Vol.38, No.10 Pages: 1723-173
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of(22E)-3α, 6α, 7α, 12α-Tetrahydroxy-5β-chol-22-en-24-oic Acid and its N-Acylamidated Conjugates with Glycine or Taurine : Presursors of the [22, 23-^3H] Labelled Tracers (2010)
  • Author(s): S. Ogawa, Y. Adachi, G. Kakiyama, M. Shimada, N. Mano, J. Goto, T. Iida
  • Journal Title: Chem. Pharm. Bull Volume: Vol.58, No.8 Pages: 1103-1106
  • Peer Reviewed
• [Journal Article] MassBank : A Public Repository for Sharing Mass Spectral Data for Life Sciences (2010)
  • Author(s): H. Horai, M. Arita, S. Kanaya, Y. Nihei, T. Ikeda, K. Suwa, Y. Ojima, K. Tanaka, S. Tanaka, K. Aoshima, Y. Oda, Y. Kakazu, M. Kusano, T. Tohge, F. Matsuda, Y. Sawada, H. Nakanishi, K. Ikeda, N. Akimoto, T. Maoka, H. Takahashi, T. Ara, H. Suzuki, D. Shibata, S. Neumann, T. Iida, K. Tanaka, K. Funatsu, F. Matsuura, T. Soga, R. Taguchi, K. Saito, T. Nishioka
  • Journal Title: J. Mass Spectrom Volume: Vol.45 Pages: 703-714
  • Peer Reviewed
• [Journal Article] Ring-Opening Metathesis Polymerization of Steroid-Conjugated Norbornenes and Gradual Release of Estrone from a Polymer Film (2010)
  • Author(s): S. Ogawa, S. Takano, H. Fujimori, T. Itoh, S. Kaita, T. Iida, Y. Wakatsuki
  • Journal Title: Reactive & Functional Polymers Volume: Vol.70 Pages: 563-571
  • Peer Reviewed
• [Journal Article] Major Biliary Bile Acids of the Medaka(Oryzias latipes): 24R-and 24S-Epimers of 3α, 7α, 12α-Trihydroxy-5β-cholestanoic Acid (2010)
  • Author(s): L. R. Hagey, T. Iida, H. Tamegai, S. Ogawa, M. Une, K. Asahina, K. Mushiake, T. Goto, N. Mano, J. Goto, M. D. Krasowski, A. F. Hofmann
  • Journal Title: Zool. Sci Volume: Vol.27, No.7 Pages: 565-573
  • Peer Reviewed
• [Journal Article] Potential Corticoid Metabolites : Chemical Synthesis of 3-and 21-Monosulfates and their Double-Conjugates of Tetrahydrocorticosteroids in the 5α-and 5β-Series (2010)
  • Author(s): R. Okihara, K. Mitamura, M. Hasegawa, M. Mori, A. Muto, G. Kakiyama, S. Ogawa, T. Iida, M. Shimada, N. Mano, S. Ikegawa
  • Journal Title: Chem. Pharm. Bull Volume: Vol.58, No.3 Pages: 344-353
  • Peer Reviewed
• [Journal Article] Oxyfunctionalization of Unactivated C-H Bonds in Triterpenoids with tert-Butylhydroperoxide Catalyzed by Meso-5, 10, 15, 20-tetramesitylporphyrinate Osmium(II) Carbonyl Complex (2010)
  • Author(s): S. Ogawa, Y. Wakatsuki, M. Makino, Y. Fujimoto, K. Yasukawa, T. Kikuchi, M. Ukiya, T. Akihisa, T. Iida
  • Journal Title: Chem. Phys. Lipids Volume: Vol.163 Pages: 165-171
  • Peer Reviewed
• [Journal Article] Hepatobiliary Disposition of 3α,6α,7α,12α-Tetrahydroxy-cholanoyl Taurine : A Substrate for Multiple Canalicular Transporters (2010)
  • Author(s): V.Megaraj, T.Iida, P.Jungsuwadee, A.F. Hofmann, M.Vore
  • Journal Title: Drug Metab.Disposi. Volume: 38巻 Pages: 1723-1730
  • Peer Reviewed
• [Journal Article] Ring-Opening Metathesis Polymerization of Steroid-Conjugated Norbornenes and Gradual Release of Estrone from a Polymer Film. (2010)
  • Author(s): S.Ogawa, S.Takano, H.Fujimori, T.Itoh, S.Kaita, T.Iida, Y.Wakatsuki
  • Journal Title: React.Funct.Polymers Volume: 70巻 Pages: 563-571
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of (22E)-3α, 6α, 7α, 12α-Tetrahydroxy-5β-chol-22-en-24-oic Acid and its N-Acylamidated Conjugates with Glycine or Taurine : Presursors of the [22, 23-^3H] Labelled Tracers (2010)
  • Author(s): S.Ogawa, Y.Adachi, G.Kakiyama, M.Shimada, N.Mano, J.Goto, T.Iida
  • Journal Title: Chem.Pharm Bull. Volume: 58巻 Pages: 1103-1106
  • Peer Reviewed
• [Journal Article] Major Biliary Bile Acids of the Medaka (Oryzias latipes) : 24R-and 24S-Epimers of 3α, 7α, 12α-Trihydroxy-5β-cholestanoic Acid (2010)
  • Author(s): L.R.Hagey, T.Iida, H.Tamegai, S.Ogawa, M.Une, K.Asahina, K.Mushiake, T.Goto, N.Mano, J.Goto, M.D.Krasowski, A.F.Hofmann
  • Journal Title: Zool.Sci. Volume: 27巻 Pages: 565-573
  • Peer Reviewed
• [Journal Article] Potential Corticoid Metabolites : Chemical Synthesis of 3-and 21-Monosulfates and their Double-Conjugates of Tetrahydrocorticosteroids in the 5α- and 5β-Series (2010)
  • Author(s): R.Okihara, K.Mitamura, M.Hasegawa, M.Mori, A.Muto, G.Kakiyama, S.Ogawa, T.Iida, M.Shimada, N.Mano, S.Ikegawa
  • Journal Title: Chem.Pharm.Bull 58巻 Pages: 344-353
  • Peer Reviewed
• [Journal Article] Oxyfunctionalization of Unactivated C-H Bonds in Triterpenoids with tert-Butylhydroperoxide Catalyzed by meso-5, 10, 15, 20-Tetramesityl porphyrinate Osmium(II)Carbonyl Complex (2010)
  • Author(s): S.Ogawa, Y.Wakatsuki, M.Makino, Y.Fujimoto, K.Yasukawa, T.Kikuchi, M.Ukiya, T.Akihisa, T.Iida
  • Journal Title: Chem.Phys.Lipids 163巻 Pages: 165-171
  • Peer Reviewed
• [Journal Article] Simultaneous Determination of Twelve Tetrahydroxycorticosteroid Glucuronides in Human Urine by Liquid Chromatograhy/Electrospray Ionization-Liner Ion Trap Mass Spectrometry (2009)
  • Author(s): S. Ikegawa, M. Hasegawa, R. Okihara, C. Shimizu, H. Chiba, T. Iida, K. Mitamura
  • Journal Title: Anal. Chem Volume: Vol.81, No.24 Pages: 10124-10135
  • Peer Reviewed
• [Journal Article] Relative Inhibitory Activity of Bile Acids Against 12-O-Tetradecanolyphorbol-13-acetate-Induced Inflammation, and Chenodeoxycholic Acid Inhibition of Tumour Promotion in Mouse Skin Two-Stage Carcinogenesis (2009)
  • Author(s): K. Yasukawa, T. Iida, Y. Fujimoto
  • Journal Title: J. Pharm. Pharmacol Volume: Vol.61 Pages: 1051-1056
  • Peer Reviewed
• [Journal Article] Chemical Synthesis 3β-Sulfooxy-7β-hydroxy-24-nor-5-cholenic Acid : an Internal Standard for Mass Spectrometric Analysis of the AbnormalΔ^5-Bile Acids in Niemann-Pick Disease (2009)
  • Author(s): G. Kakiyama, A. Muto, M. Shimada, N. Mano, J. Goto, A. F. Hofmann, T. Iida
  • Journal Title: Steroids Volume: Vol.74 Pages: 766-772
  • Peer Reviewed
• [Journal Article] A New, Major C_<27> Biliary Bile Acid in the Red-Winged Tinamou(Rhynchotus rufescens :(24R)-1β, 3α, 7α-Trihydroxy-5β-cholestan-27-oic Acid (2009)
  • Author(s): L. R. Hagey, G. Kakiyama, A. Muto, T. Iida, K. Mushiake, T. Goto, N. Mano, J. Goto, G. A. Oliveira, A. F. Hofmann
  • Journal Title: J. Lipid Res Volume: Vol.50 Pages: 651-657
  • Peer Reviewed
• [Journal Article] A Facile Synthesis of C-24 and C-25 Oxysterols by in situ Generated Ethyl(trifluromethyl) dioxirane (2009)
  • Author(s): S. Ogawa, G. Kakiyama, A. Muto, A. Hosoda, K. Mitamura, S. Ikegawa, A. F. Hofmann, T. Iida
  • Journal Title: Steroids Volume: Vol.74、No.1 Pages: 81-87
  • Peer Reviewed
• [Journal Article] Potential Corticoid Metabolites : Chemical Synthesis of 3-and 21-Monosulfates and their Double-Conjugates of Tetrahydrocorticosteroids in the 5α- and 5β-Series (2009)
  • Author(s): S.Ikegawa, M.Hasegawa, R.Okihara, C.Shimidzu, H.Chiba, T.Iida, K.Mitamura
  • Journal Title: Anal.Chem. 81巻 Pages: 10124-10135
  • Peer Reviewed
• [Journal Article] Relative inhibitory activity of bile acids against 12-O-tetradecanolyphorbol-13-acetate-induced inflammation, and chenodeoxycholic acid inhibition of tumour promotion in mouse skin two-stage carcinogenesis (2009)
  • Author(s): K.Yasukawa, T.Iida, Y.Fujimoto
  • Journal Title: J.Pharm.Pharmacol. 61巻 Pages: 1051-1056
  • Peer Reviewed
• [Journal Article] Chemical Synthesis 3β-Sulfooxy-7β-hydroxy-24-nor-5-cholenic Acid : An Internal Standard for Mass Spectrometric Analysis of the Abnormal delta-5-Bile Acids In Niemann-Pick Diesesse (2009)
  • Author(s): G.Kakiyama, A.Muto, M.Shimada, N.Mano, J.Goto, A.F.Hofmann, T.Iida
  • Journal Title: Steroids 74巻 Pages: 766-772
  • Peer Reviewed
• [Journal Article] A new, major C_<27> biliary bile acid in the Red-winged tinamou(Rhynchotus rufescens): (25R)-1β, 3α, 7α-trihydroxy-5β-cholestan-27-oic acid (2009)
  • Author(s): L.R.Hagey, G.Kakiyama, A.Muto, T.Iida, K.Mushiake, T.Goto, N.Mano, J.Goto, C.A.Oliveira, A.F.Hofmann
  • Journal Title: J.Lipid Res. 50巻 Pages: 651-657
  • Peer Reviewed
• [Presentation] 同位体希釈LC/ESI-MSに用いる多重重水素標識allo-tetrahydrocorticosteroid 3-及び21-monosulfateの合成 (2012)
  • Author(s): 池川繁男, 中島理陽, 小川祥二郎, 飯田隆, 三田村邦子
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
• [Presentation] オオトカゲ胆嚢胆汁成分から新規胆汁酸の単離・同定: Tauro-(24R, 25S)-3α, 7α, 12α, 24-tetrahydroxy-5β-cholestan-27-oic acid (2012)
  • Author(s): 小川祥二郎, 飯田隆, 三田村邦子, 池川繁男, 宇根瑞穂, L. R. Hagey, A. F. Hofmann
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
• [Presentation] 同位体希釈LC/ESI-MSに用いる多重重水素標識allo-tetrahydrocorticosteroid3-及び21-monosulfateの合成 (2012)
  • Author(s): 池川繁男, 中島理陽, 小川祥二郎, 飯田隆, 三田村邦子
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
• [Presentation] オオトカゲ胆嚢胆汁成分から新規胆汁酸の単離・同定:Tauro-(24R,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (2012)
  • Author(s): 小川祥二郎, 飯田隆, 三田村邦子, 池川繁男, 宇根瑞穂, Lee R.Hagey, Alan F.Hofmann
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
• [Presentation] Δ^4-3-Oxo-steroid 5β-reductase欠損症の新生児スクリーニングの検討 (2011)
  • Author(s): 武井一, 入戸野博, 飯田隆, 他10名
  • Organizer: 第33回胆汁酸研究会
  • Place of Presentation: 大阪ガーデンパレス
  • Year and Date: 2011-11-19
• [Presentation] 脂肪肝予防・治療薬としてのFXRリガンドの可能性について (2011)
  • Author(s): 宮崎照雄, 本多彰, 池上正, 飯田隆, 松崎靖司
  • Organizer: 第33回胆汁酸研究会
  • Place of Presentation: 大阪ガーデンパレス
  • Year and Date: 2011-11-19
• [Presentation] トカゲ亜目から新規胆汁酸の単離・構造決定: Tauro-(24R, 25S)-3α, 7α, 12α, 24-tetrahydroxy-5β-cholestan-27-oic acid (2011)
  • Author(s): 小川祥二郎, 飯田隆, 加藤也実, 宇根瑞穂, L. R. Hagey, A. F. Hofmann
  • Organizer: 第33回胆汁酸研究会
  • Place of Presentation: 大阪ガーデンパレス
  • Year and Date: 2011-11-19
• [Presentation] トカゲ亜目から新規胆汁酸の単離・構造決定:Tauro-(24R,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (2011)
  • Author(s): 小川祥二郎, 飯田隆, 加藤也実, 宇根瑞穂, L.R.Hagey, A.F.Hofmann
  • Organizer: 第33回胆汁酸研究会
  • Place of Presentation: 大阪ガーデンパレス
  • Year and Date: 2011-11-19
• [Presentation] 新規遠隔含酸素官能基化剤(メタロポルフィリン/酵素ドナー系)の開発と生理活性物質合成への高度利用 (2011)
  • Author(s): 飯田隆, 小川祥二郎
  • Organizer: 私学研究基盤形成支援事業「構造制御および電子状態制御に基づく新物質の開発」
  • Place of Presentation: 日本大学文理学部広領域情報科学センター
  • Year and Date: 2011-08-10
• [Presentation] 胆道閉鎖症における肝機能検査値と尿中胆汁酸分画の日齢変化 (2011)
  • Author(s): 入戸野博, 飯田隆, 他8名
  • Organizer: 第20回小児胆汁酸研究会
  • Place of Presentation: 山の上ホテル(東京)
  • Year and Date: 2011-02-12
• [Presentation] 新生児の胆嚢および腸管内胎便中の胆汁酸分析 (2011)
  • Author(s): 武藤晃奈, 武井一, 吽野篤, 入戸野博, 佐藤洋明, 村井毅, 黒澤隆夫, 藤間貞彦, 飯田隆
  • Organizer: 第20回小児胆汁酸研究会
  • Place of Presentation: 山の上ホテル(東京)
  • Year and Date: 2011-02-12
• [Presentation] タンデムマスによる先天性胆汁酸代謝異常症スクリーニングの試み (2011)
  • Author(s): 無井一, 武藤晃奈, 入戸野博, 吽野篤, 清水俊明, 飯田隆, 村井毅, 黒澤隆夫, 藤間貞彦
  • Organizer: 第20回小児胆汁酸研究会
  • Place of Presentation: 山の上ホテル(東京)
  • Year and Date: 2011-02-12
• [Presentation] ハゲガオカザリドリ(Perissocephalus tricolor)とハゲノドスズドリ(Procnias nudicollis)の胆汁成分に関する研究 (2011)
  • Author(s): 足立祐樹、小川祥二郎、飯田隆、宇根瑞穂、眞野成康、後藤順一、L. R. Hagey、A. F. Hofmann
  • Organizer: 第20回小児胆汁酸研究会
  • Place of Presentation: 山の上ホテル(東京)
  • Year and Date: 2011-02-12
• [Presentation] ハゲガオカザリドリ(Perissocephalus tricolor)とハゲノドスズドリ(Procnias nudicollis)の胆汁成分に関する研究 (2011)
  • Author(s): 足立祐樹、小川祥二郎、飯田隆、宇根瑞穂、眞野成康、後藤順一、Lee R.Hagey、Alan F.Hofmann
  • Organizer: 第20回小児胆汁酸研究会
  • Place of Presentation: 山の上ホテル
  • Year and Date: 2011-02-12
• [Presentation] タンデム質量分析法を利用した抱合型胆汁酸メタボローム解析法の検討 (2011)
  • Author(s): 前川正充, 入戸野博, 飯田隆, 他8名
  • Organizer: 第24回バイオメディカル分析科学シンポジウム
  • Place of Presentation: 大山ロイヤルホテルA会場
• [Presentation] LC/ESI/-MS/MS method for focusing metabolome of bile acid conjugates (2011)
  • Author(s): M. Maekawa, M. Mori, H. Suzuki, T. Iida, M. Shimada, N. Mano
  • Organizer: 59^<th> Conference on Mass Spectrometry and Allied Topics
  • Place of Presentation: USA
• [Presentation] Liquid chromatography/mass spectrometric characterization of non-enzymatic acylation of amino or thiol groups of bionucleophiles by the cholyl-adenylate or cholyl-CoA thioester (2011)
  • Author(s): K. Mitamura, E. Aoyama, T. Sakai, T. Iida, A. F. Hofmann, S. Ikegawa
  • Organizer: 59^<th> Conference on Mass Spectrometry and Allied Topics
  • Place of Presentation: USA
• [Presentation] Liquid chromatography-mass spectrometric characterization of sulfation of N-acetylcysteine conjugated bile acids by a rat liver cytosolic fraction (2011)
  • Author(s): S. Ikegawa, T. Sakai, R. Nakai, T. Wakamiya, T. Iida, A. F. Hofmann, K. Mitamura
  • Organizer: 59^<th> Conference on Mass Spectrometry and Allied Topics
  • Place of Presentation: USA
• [Presentation] ハゲガオカザリドリ(Perissocephalus tricolor)とハゲノドスズドリ(Procnias nudicollis)の胆汁成分に関する研究 (2011)
  • Author(s): 小川祥二郎, 足立祐樹, 眞野成康, 後藤順一, 宇根瑞穂, L. R. Hagey, A. F. Hofmann, 飯田隆
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: グランシップ、ツインメッセ静岡
• [Presentation] LC/ESI/-MS/MS method for focusing metabolome of bile acid conjugates (2011)
  • Author(s): M.Maekawa, M.Mori, H.Suzuki, T.Iida, M.Shimada, N.Mano
  • Organizer: 59th Conference on Mass Spectrometry and Allied Topics
  • Place of Presentation: USA
• [Presentation] Liquid chromatography-mass spectrometric characterization of sulfation of N-acetyl cysteine conjugated bile acids by a rat liver cytosolic fraction (2011)
  • Author(s): S.Ikegawa, T.Sakai, R.Nakai, T.Wakamiya, T.Iida, A.F.Hofmann, K.Mitamura
  • Organizer: 59^<th> Conference on Mass Spectrometry and Allied Topics
  • Place of Presentation: USA
• [Presentation] 潜在的胆汁酸3α,7α,12α-Trihydroxy-5α-cholestan-26-oic acidエピマー体とその抱合体の化学合成 (2010)
  • Author(s): 小川祥二郎、飯田隆、岡田浩章、池川繁男、三田村邦子、Alan F Hofinann
  • Organizer: 第32回胆汁酸研究会
  • Place of Presentation: 東北大学
  • Year and Date: 2010-11-06
• [Presentation] Isolation, identification and comparative study of bile acids in the capuchinbird (Perissocephalus tricol) and bare-throated bellbird (Procnias nndicollis) (2010)
  • Author(s): S.Ogawa, Y.Adachi, T.Iida, M.Une, N.Mane, J.Goto, M.D.Krasowski, L.R.Hagey, A.F.Hofmann
  • Organizer: Falk Symposium 175 : XXI International Bile Acid Meeting
  • Place of Presentation: Konzerthaus, Freiburg (Germany)
• [Presentation] Chemical synthesis of the (25R)-and (25S)-epimers of 3α, 7α, 12α-trihydroxy-5α-cholestan-27-oic acid and their glycine and taurine conjugates (2010)
  • Author(s): T.Iida, S.Ogawa, K.Mitamura, S.Ikegawa, M.D.Krasowski, L.R.Hagey, A.F.Hofmann
  • Organizer: Falk Symposium 175 : XXI International Bile Acid Meeting
  • Place of Presentation: Konzerthaus, Freiburg (Germany)
• [Presentation] (2010)
  • Author(s): 小方聖太郎, 伊藤敏宏, 為我井秀行, 小川祥二郎, 飯田隆, 若槻康雄
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 近畿大学
• [Presentation] メダカ(Oryzias latipes)の胆汁成分に関する研究 (2009)
  • Author(s): 小川祥二郎, 飯田隆, 眞野成康, 後藤順一, Lee R.Hagey, Alan F.Hofmann
  • Organizer: 第31回胆汁酸研究会
  • Place of Presentation: 東京大学
  • Year and Date: 2009-11-07