Formation of Natamycin:Cyclodextrin Inclusion Complexes and Their Characterization

Abstract

Natamycin is a broad spectrum antimycotic with very low water solubility, which is used to extend the shelf life of shredded cheese products. beta-Cyclodextrin (beta-CD), hydroxypropyl beta-cyclodextrin (HP beta-CD), and gamma-cyclodextrin (gamma-CD) were found to form inclusion complexes with natamycin in aqueous solution. The increase in solubility of natamycin with added beta-CD was observed to be linear (type A(L) phase solubility diagram). The 1:1 stability constant of natamycin:beta-CD complex was estimated from its phase solubility diagram to be 1010 M(-1). The phase solubility diagrams of both gamma-CD and HP beta-CD exhibited negative deviation from linearity (type A(N) diagram) and, therefore, did not allow the estimation of binding constants. The water solubility of natamycin was increased 16-fold, 73-fold, and 152-fold with beta-CD, gamma-CD, and HP beta-CD, respectively. The natamycin:CD inclusion complexes resulted in in vitro antifungal activity nearly equivalent to that of natamycin in its free state.

Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes

“…It has been reported that the inclusion complexes of guest compounds with CDs can enhance guest stability, improve the aqueous solubility, protect against oxidation, light-induced decomposition, and heat-induced changes, and mask or reduce unwanted physiological effects, and reduce volatility (Hedges, 1998). For example, the natamycin/CDs complexes have allowed a homogeneous delivery system of natamycin to the shredded cheese surface without the clogging of spray nozzles during cheese production (Koontz & Marcy, 2003).…”

Does use of the polyene natamycin as a food preservative jeopardise the clinical efficacy of amphotericin B? A word of concern

“…The cyclodextrin molecule can at least partially shield the guest molecule from degradation caused by light, oxidation, heat, and acidic or alkaline conditions [9]. Cyclodextrins not only insulate labile compounds from a potentially corrosive environment, they also increase solubility of poorly soluble agents [8,10]. Inclusion of natamycin into cyclodextrin permits the preparation of a complex containing 500 mg/L of solubilised natamycin and protects natamycin from inactivation in an acidic environment as prevailing in beverages.…”

The inhibitory effect of Natamycin and Potassium Sorbate on mold growth in Egyptian Fresh soft cheese (Tallaga Cheese)

“…Natamycin, as a natural preservative, is used in dairy products and other foods in over sixty countries (Delves-Broughton et al, 2005). Natamycin is identified by the European Union as a natural preservative (EFSA, 2009) and it has been described as generally recognized as safe (GRAS) product for human by FDA (Koontz and Marcy 2003).…”