Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine Sponge Geodia exigua and Related Compounds
スポンサーリンク
概要
- 論文の詳細を見る
(−)-10-epi-Axisonitrile-3, a spirocyclic sesquiterpene isocyanide obtained from the marine sponge Geodia exigua, immobilized sperm of sea urchin and starfish to block fertilization at the minimum effective concentration of 0.4 μg/ml. On the other hand, fertilized eggs developed normally to the gastrula stage in the presence of a 250-times higher concentration of the isocyanide. Analysis by 31P NMR revealed an accumulation of phosphocreatine and a depletion of inorganic phosphate in the isocyanide-treated sperm, suggesting that (−)-10-epi-axisonitrile-3 inhibited the phosphocreatine shuttle participating in the high-energy phosphate metabolism, thereby immobilizing sperm to block fertilization. No analogs of (−)-10-epi-axisonitrile-3 containing different functionalities or isocyanides with different carbon skeleton exhibited such activity.
- 社団法人 日本農芸化学会の論文
著者
-
HIRATA Toshifumi
Department of Chemistry, Faculty of Science, Hiroshima University
-
OHTA Emi
Nagahama Institute of Bio-Science and Technology
-
UY Mylene
Department of Mathematical and Life Sciences, Graduate School of Science, Hiroshima University
-
OHTA Shinji
Nagahama Institute of Bio-Science and Technology
-
YANAI Mihoko
Natural Science Center for Basic Research and Development, Hiroshima University
-
IKEGAMI Susumu
Nagahama Institute of Bio-Science and Technology
関連論文
- Secretion of 112 kDa Phosphatase from the Cultured Suspension Cells of Liverworts
- Secretion of Alleochemicals from the Cultured Suspension Cells of Marchantia polymorpha
- High Molecular Weight Corticotropin Measured with Immunoradiometric Assay in a Patient with Asymptomatic Pituitary Corticotropinoma
- LOCALIZATION OF NAAP PROTEIN IN THE NUCLEOLUS OF THE STARFISH EMBRYONIC CELL(Developmental Biology)(Proceeding of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- DETERMINATION OF NUCLEOLAR TARGETING SIGNALS IN NAAP, A NUCLEOLAR PROTEIN OF THE STARFISH OOCYTE(Developmental Biology)Proceedings of the Seventy-First Annual Meeting of the Zoological Society of Japan
- NUCLEAR TRANSGLUTAMINASE IN STARFISH EMBRYOS(Developmental Biology)(Proceedings of the Seventieth Annual Meeting of the Zoological Society of Japan)
- cDNA CLONING OF TRANSGLUTAMINASE GENES OF STARFISH EARLY EMBRYOS(Developmental Biology)(Proceedings of the Sixty-Ninth Annual Meeting of the Zoological Society of Japan)
- TOPOGENESIS OF NAAP, A NUCLEOLAR PROTEIN IN THE STARFISH OOCYTE(Developmental Biology)(Proceedings of the Sixty-Ninth Annual Meeting of the Zoological Society of Japan)
- Inhibition of Chromosome Separation in Fertilized Starfish Eggs by Kalihinol F, a Topoisomerase I Inhibitor Obtained from a Marine Sponge(Biochemistry & Molecular Biology)
- Adrenal Insufficiency after Incomplete Resection of Pituitary Macrocorticotropinoma of Cushing's Disease: Role of High Molecular Weight ACTH
- Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine Sponge Geodia exigua and Related Compounds
- A MARINE-SPONGE-DERIVED SUBSTANCE THAT INHIBITS CELL FATE SPECIFICATION DURING SEA URCHIN EMBRYOGENESIS(Developmental Biology,Abstracts of papers presented at the 75^ Annual Meeting of the Zoological Society of Japan)
- SELECTIVE DESTRUCTION OF ACTIN-BASED CYTOSKELETON NETWORKS IN THE IMMATURE STARFISH OOCYTE BY THEONELLAPEPTOLIDE IE, A PEPTIDE FROM A MARINE SPONGE(Developmental Biology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society
- Malformation of Immature Starfish Oocytes by Theonellapeptolide Ie, a Tridecapeptide Lactone from a Marine Sponge Petrosia Species, through Disturbance of Cortical F-Actin Distribution(Biochemistry & Molecular Biology)
- EFFECT OF PACHASTRELLOSIDE A, A STEROID GLYCOSIDE FROM A SPONGE PACHASTRELLA SP., ON CYTOKINESIS OF STARFISH (ASTERINA PECTINIFERA) EMBRYOS(Developmental Biology)(Proceedings of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- Asymmetric Transformation of Enones with Synechococcus sp. PCC 7942
- A novel hydroxylase from Catharanthus roseus participating in the hydroxylation of 2-hydroxybenzoic acid
- DIMERIZATION OF CORE HISTONES CATALYZED BY TRANSGLUTAMINASE IN STARFISH SPERM NUCLEI(Developmental Biology)(Proceeding of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- NUCLEAR TRANSGLUTAMINASE OF STARFISH GASTRULAE INTERACTS WITH CHROMATIN(Developmental Biology)(Proceeding of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- The appearance and structure of a starfish histone H2B-H4 dimer(Developmental Biology)Proceedings of the Seventy-First Annual Meeting of the Zoological Society of Japan
- CELLULAR LOCALIZATION OF THE STARFISH EMBRYO NUCLEAR TRANSGLUTAMINASE EXPRESSED IN MAMMALIAN CELLS(Developmental Biology)Proceedings of the Seventy-First Annual Meeting of the Zoological Society of Japan
- LOCALIZATION OF P28, A HISTONE HETERODIMER IN STARFISH SPERM NUCLEI(Developmental Biology)(Proceedings of the Seventieth Annual Meeting of the Zoological Society of Japan)
- CHANGES OF SUBCELLULAR LOCALIZATION OF TRANSGLUTAMINASE DURING STARFISH EMBRYONIC DEVELOPMENT(Developmental Biology)(Proceedings of the Sixty-Ninth Annual Meeting of the Zoological Society of Japan)
- FORMATION OF HISTONE HETERODIMERS IN STARFISH SPERM NUCLEI AND THEIR DISAPPEARANCE FROM THE MALE PRONUCLEUS(Developmental Biology)(Proceedings of the Sixty-Ninth Annual Meeting of the Zoological Society of Japan)
- Characterization of Recombinant p20 Trypsin Inhibitor, a New Protein from Glycine max
- Molecular Cloning and mRNA Expression of Geraniol-inducible Genes in Cultured Shoot Primordia of Matricaria chamomilla(Biochemistry & Molecular Biology)
- Geraniol-inducible Glutathione S-Transferase in Cultured Soybean Cells(Biochemistry & Molecular Biology)
- Isolation and structure determination of a cDNA encoding for a thiol protease from the cultured shoot primordia of Matricaria chamomilla
- Isolation of a cDNA Encoding for a Carboxypeptidase, having Leucine Zipper Structure at the N-terminal Region, from the Cultured Shoot Primordia of Matricaria chamomilla
- A 20-kDa Protein with the GTP-Binding and Trypsin Inhibitory Activities from Glycine max
- Enantioselectivity in the Hydrolysis by Lipase: A Study of MALDI TOF-MS Analysis
- Monoterpenoids, Potent Inducers of Apoptosis in the Cells of Marchantia polymorpha
- Enantioselective Glucosylation of(R, S)-1-Phenylethanol by the Cultured Suspension Cells of Higher Plants
- Asymmetric Hydrolyses of 1,2-Diacetoxycyclohexanes by the Cultured Suspension Cells of Marchantia polymorpha
- Distereoselective Formation of Disaccharides from(RS)-1- Phenylethanol by Cultured Cells of Catharanthus roseus
- Intraoperative Radiation Therapy for Malignant Glioma
- Tumors at the Trigone of the Lateral Ventricle : Clinical Analysis of Eight Cases
- Isolation and Sequencing of a cDNA Clone Encoding a 20-kDa Protein with Trypsin Inhibitory Activity
- Asymmetric Hydrogenation of the C-C Double Bond of Enones with the Reductases from Nicotiana tabacum
- Signal Transduction against the Terpenoid-Stimulation in the Liverwort Cells
- A Novel Reductase Participating in the Hydrogenation of an Exocyclic C-C Double Bond of Enones from Nicotiana tabacum
- Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine Sponge Geodia exigua and Related Compounds
- Characterization of nuclear transglutaminase in starfish, Asterina pectinifera(Developmental Biology)(Proceeding of the Seventy-Third Annual Meeting of the Zoological Society of Japan)
- Jaspisin, a Novel Styryl Sulfate from the Marine Sponge, Jaspis Species
- JBIR-14, a highly oxygenated ergostane, from Isaria sp. NBRC 104353