Total Synthesis of (+)-Scyphostatin, a Neutral Sphingomyelinase Inhibitor
نویسندگان
چکیده
منابع مشابه
Neutral sphingomyelinase inhibitor scyphostatin prevents and ceramide mimics mechanotransduction in vascular endothelium.
Recently, we showed that neutral sphingomyelinase (N-SMase) is concentrated at the endothelial cell surface in caveolae and is activated to produce ceramide in an acute and transient manner by increase in flow rate and pressure in rat lung vasculature (Czarny M, Liu J, Oh P, and Schnitzer JE, J Biol Chem 278: 4424-4430, 2003). Here, we report further on our investigations of this new acute mech...
متن کاملSynthesis and evaluation of three novel scyphostatin analogues as neutral sphingomyelinase inhibitors.
Low-molecular-weight inhibitors of sphingomyelinases have attracted considerable attention as molecular tools for the investigation of the enzymatic mechanism of the various isoforms of these enzymes and for clarification of their biological role, as well as the role of the product of their action on sphingomyelin (ceramide), in apoptosis and signal-transduction processes. In addition, such mol...
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We performed experiments to screen for neutral sphingomyelinase inhibitors using rat brain microsomes as an enzyme source. Among more than 10,000 microbial extracts tested, a mycelial extract of Trichopeziza mollissima SANK 13892 exhibited potent inhibitory activity. The active compound, scyphostatin, was purified by a series of chromatographies. Scyphostatin inhibited the enzyme with an IC50 v...
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Chlorogentisylquinone, a new inhibitor of neutral sphingomyelinase activity, was purified from the culture broth of a fungal strain FOM-8108 isolated from a marine environment by solvent extraction, silica gel chromatography and Sephadex LH-20 chromatography. Its chemical structure was elucidated by spectroscopic studies including 1H, 13C, DEPT, HMQC and HMBC NMR experiments. Chlorogentisylquin...
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Ceramide is a bioactive lipid that plays an important role in stress responses leading to apoptosis, cell growth arrest and differentiation. Ceramide production is due in part to sphingomyelin hydrolysis by sphingomyelinases. In brain, neutral sphingomyelinase 2 (nSMase2) is expressed in neurons and increases in its activity and expression have been associated with pro-inflammatory conditions o...
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 2007
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.65.358