title: A new alpha,beta,gamma,delta-unsaturated carboxylic acid and three new cyclic peroxides from the marine sponge, Monotria japonica, which selectively lyse starfish oocytes without affecting nuclear morphology.
abstract: The marine sponge Monotria japonica contains cytolytic constituents, which have been fractionated to a new alpha,beta,gamma,delta-unsaturated carboxylic acid designated monotriajaponide A (1) and three new cyclic peroxides designated monotriajaponides B (2), C (3), and D (4), in addition to a known peroxide (5) and a known alpha,beta-unsaturated ester (6). The structures were determined on the basis of spectroscopic data. Compounds 1-5 lysed immature starfish (Asterina pectinifera) oocytes without affecting nuclear morphology at the minimum effective concentrations of 50, 6.3, 6.3, 6.3, and 13 microg/mL, respectively. On the other hand, compound 6, at the minimum effective concentration of 25 microg/mL, lysed both oocyte's plasma membrane and the nuclear envelope.
authors.affiliation: Instrument Center for Chemical Analysis, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan.
authors.forename: Mihoko
authors.initials: M
authors.lastname: Yanai
authors.forename: Shinji
authors.initials: S
authors.lastname: Ohta
authors.forename: Emi
authors.initials: E
authors.lastname: Ohta
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Hirata
authors.forename: Susumu
authors.initials: S
authors.lastname: Ikegami
mesh_terms: D000818:Animals; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002467:Cell Nucleus / Q000187:drug effects* / Q000648:ultrastructure; D004146:Dioxanes / Q000737:chemistry; D008856:Microscopy, Fluorescence; D019906:Nuclear Magnetic Resonance, Biomolecular; D009865:Oocytes / Q000166:cytology / Q000187:drug effects* / Q000648:ultrastructure; D010545:Peroxides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011161:Porifera / Q000737:chemistry*; D013215:Starfish; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D004146:Dioxanes; D010545:Peroxides