Application of newly synthesized detergents in the side chain degradation of plant sterols by Mycobacterium fortuitum

Abstract

Newly synthesized detergents of polyoxyethylene polyoxypropylene co-polymers (Co-EOPO), polyoxyethylene polyoxypropylene adducts of the diethylene triamine (DETA-EOPO), and steroidal detergents (SDD) stimulate significantly side chain degradation of plant sterols referring to both the sterol degradation and the formation of the product, 9 alpha-hydroxy-androsta-4-ene-3,17-dione (9 OH-AD), by Mycobacterium fortuitum NRRL-B-8119. Highest stimulative effects were observed with derivatives of the DETA-EOPO group. Using compounds of the Co-EOPO group optimal sterol transformation rates were found for polymers with a polyoxypropylene domain of 1400-2000 in molecular weight and with a polyoxyethylene content of 20-50%. Mostly efficient steroidal detergents tested were the 4-cholesten-3-(O-carboxymethyl)-oxime and the amino acid adducts of sterol-3 beta-chlorocarbonates. Detergents were favourably applied as pre-formed sterol-detergent complexes (9:1/w:w) in submers fermentation procedures. By treating harvested resting cells of M. fortuitum with derivatives of Co-EOPO or DETA-EOPO a considerable activation of the cells takes place concerning the sterol degradation and the formation of 9 OH-AD at a high yield in subsequent transformation process on buffer. In solubilization experiments we revealed that there is no correlation between the detergent mediated solubilization of the hydrophobic sterol substrate in the aqueous medium and the transformation activity of the bacterial cells. The detergents are assumed to interact with a multicomponent mesophase (FMCM) which is placed between cells and sterol surface and mediates the transport.

Degradation of polycyclic aromatic hydrocarbons in the presence of synthetic surfactants

“…Triton X-100 decreased the phenanthrene degradation by a mixed culture (19) and completely inhibited the sterol transformation by Mycobacterium fortuitum (3). Thus, the more hydrophobic surfactants that seem to exhibit better solubilizing properties (3,17) are tolerated by only a few bacteria.…”

“…The potential of surfactants to increase the concentration of hydrophobic compounds in the water phase suggested that the degradation of hydrocarbons might be accelerated by the addition of surfactant. Attempts to enhance the metabolization rates of nonpolar substrates by the use of surfactants gave contradictory results (3,6,8,14,15). Although surfactants have been studied in complex watersoil systems (2,19,23), the effects are not well understood.…”

Fate of Triton X‐100 Applications on Water and Soil Environments: A Review

“…The mixed culture of soil microorganisms [11] is also tolerant to 2,650 mg/l of Triton X-100 in the hydrophobic substrate (Table 2), as well as the PAH-degrading bacteria of contaminated waste soil [8,27,36]. The single organisms: Pseudomonas species, Sphingomonas yanoikuyae [30,31,39], Bacillus subtilis [3], Escherichia coli [27], and Mycobacterium species [31,40] ( Table 3) are more tolerant to Triton X-100 in hydrophilic substrates than in hydrophobic substrates. Furthermore, the types of hydrophobic substrates affect the tolerance of microorganism to Triton X-100.…”

Green Manufacturing of Steroids via Mycolicbacteria: Current Status and Development Trends

“…[52,53]. For instance, cholesterol degradation entails distinct processes, including nucleus cleavage and β-oxidation of the C17 side chain [54][55][56][57]. These pathways operate independently for efficient degradation.…”