title: Trichocyalides A and B, new inhibitors of alkaline phosphatase activity in bone morphogenetic protein-stimulated myoblasts, produced by Trichoderma sp. FKI-5513.
abstract: Two new butenolides, designated trichocyalides A and B, were isolated along with the known compound harzianolide, from the culture broth of Trichoderma sp. FKI-5513 by solvent extraction, ODS column chromatography and HPLC. Their structures were elucidated by several spectral analyses, showing that they have the common skeleton of butenofuranone. Trichocyalides A and B inhibited alkaline phosphatase (ALP) activity, a typical marker enzyme of osteoblastic differentiation (IC(50): 83.0 and 187 μM, respectively), in bone morphogenetic protein (BMP)-stimulated C2C12 myoblasts mutant cells, which stably express BMP receptor activity, whereas harzianolide showed no inhibitory activity against ALP even at 500 μM.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Fukuda
authors.forename: Ryuji
authors.initials: R
authors.lastname: Uchida
authors.forename: Satoshi
authors.initials: S
authors.lastname: Ohte
authors.forename: Hiroyo
authors.initials: H
authors.lastname: Inoue
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamazaki
authors.forename: Daisuke
authors.initials: D
authors.lastname: Matsuda
authors.forename: Kenichi
authors.initials: K
authors.lastname: Nonaka
authors.forename: Rokurou
authors.initials: R
authors.lastname: Masuma
authors.forename: Takenobu
authors.initials: T
authors.lastname: Katagiri
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tomoda
mesh_terms: D030201:Activin Receptors, Type I / Q000037:antagonists & inhibitors / Q000235:genetics; D000469:Alkaline Phosphatase / Q000037:antagonists & inhibitors*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019485:Bone Morphogenetic Proteins / Q000378:metabolism / Q000494:pharmacology; D002073:Butanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002460:Cell Line; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017930:Genes, Reporter; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D051379:Mice; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D015394:Molecular Structure; D032446:Myoblasts / Q000187:drug effects* / Q000201:enzymology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D015398:Signal Transduction / Q000187:drug effects; D014242:Trichoderma / Q000737:chemistry* / Q000145:classification / Q000235:genetics
chemical_list: D000900:Anti-Bacterial Agents; D019485:Bone Morphogenetic Proteins; D002073:Butanes; D004791:Enzyme Inhibitors; D007783:Lactones; C577797:harzianolide; C577795:trichocyalide A; C577796:trichocyalide B; D030201:Activin Receptors, Type I; C498943:Acvr1 protein, mouse; D000469:Alkaline Phosphatase