Filipin III

Thursday, June 1, 2017

Filipin III is the major component of Filipin complex, which includes also: Filipin I, Filipin II and Filipin IV. Filipin complex was first isolated from culture of Streptomyces Filipinensis by Whitfield et al in 1955. Recently Filipin III was identified also in a culture of S. miharaensis (Kim at el, 2012).

 

Biological Activity and Applications

Filipin III is a polyene macrolide antibiotic which exhibits antifungal activity (Whitfield at el, 1955; Ceder and Ryhage, 1964). Filipin binds membrane sterols and alters the membrane structure. Unlike most polyene macrolides, Filipin has a high affinity for cholesterol containing membranes, and therefore has toxic implications for mammalian cells and cannot be used as a therapeutic agent (Payero et al, 2014). However, Filipin is widely used as a marker for detection and quantification of cholesterol in cellular membranes. The diagnosis of Neimann-Pick C disease, a cellular cholesterol trafficking defect, required staining of living skin fibroblasts with Filipin (Vanier and Latour, 2015). Filipin III was found to trigger signaling responses in tobacco cells, including a NADPH oxidase-dependent production (Bonneau et al, 2010). These findings suggest using Filipin III as a tool in research of signaling processes at plant cells.

 

 

 Filipin III molecule

 

 

References: 
  1. Plasma membrane sterol complexation, generated by filipin, triggers signaling responses in tobacco cells. Bonneau L, Gerbeau-Pissot P, Thomas D, Der C, Lherminier J, Bourque S, Roche Y, Simon-Plas F.,Biochim. Biophys. Acta. (2010) 1798:2150.
  2. The structure of filipin., Ceder O, Ryhage R,  Acta Chem. Scand. (1964) 18:558
  3. Identification and biocontrol efficacy of Streptomyces miharaensis producing filipin III against Fusarium wilt., Kim JD, Han JW, Hwang IC, Lee D, Kim BS., J. Basic Microbiol. (2012) 52:150
  4. Functional analysis of filipin tailoring genes from Streptomyces filipinensis reveals alternative routes in filipin III biosynthesis and yields bioactive derivatives., Payero TD, Vicente CM, Rumbero Á, Barreales EG, Santos-Aberturas J, de Pedro A, Aparicio JF., Microb. Cell Fact. (2015) 14:114
  5. Laboratory diagnosis of Niemann-Pick disease type C: the filipin staining test., Vanier MT, Latour P., Methods Cell Biol. (2015) 126:357.
  6. Filipin, an Antifungal Antibiotic: Isolation and Properties., Whitfield GB, Brock TD, Ammann A., Gottlieb D., Carter H. E., J. Am. Chem. Soc., (1955) 77: 4799