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.
MeSH terms
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Activin Receptors, Type I / antagonists & inhibitors
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Activin Receptors, Type I / genetics
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Alkaline Phosphatase / antagonists & inhibitors*
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Animals
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology
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Bone Morphogenetic Proteins / metabolism
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Bone Morphogenetic Proteins / pharmacology
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Butanes / chemistry
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Butanes / isolation & purification*
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Butanes / pharmacology*
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Cell Line
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / isolation & purification*
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Enzyme Inhibitors / pharmacology*
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Genes, Reporter
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology*
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Mice
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Microbial Sensitivity Tests
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Molecular Sequence Data
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Molecular Structure
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Myoblasts / drug effects*
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Myoblasts / enzymology*
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Nuclear Magnetic Resonance, Biomolecular
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Signal Transduction / drug effects
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Trichoderma / chemistry*
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Trichoderma / classification
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Trichoderma / genetics
Substances
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Anti-Bacterial Agents
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Bone Morphogenetic Proteins
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Butanes
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Enzyme Inhibitors
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Lactones
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harzianolide
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trichocyalide A
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trichocyalide B
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Activin Receptors, Type I
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Acvr1 protein, mouse
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Alkaline Phosphatase