Combined structural and biological activities for new polyunsaturated fatty derivatives obtained by biotechnological process

Abstract

The objective of this study is to demonstrate the use of new polyunsaturated fatty derivatives for cutaneous applications. These new compounds present an analogue structure of cutaneous lipid, stabilize the polyunsaturated fatty acids (face to oxidation) and demonstrate specific biological activities. Three molecules described are Omega 6 fatty acid stabilized compound (O6FASC), the O3FASC and the O9FASC. The derivatives are synthesized via the same biotechnological process. This work describes the choice of final structure, the design of the biotechnological process and the free solvent enzymatic synthesis used for the synthesis of these three cutaneous lipid analogues. The restructuring effect of such analogues has been demonstrated with an in vivo study on volunteers. The stabilization of the O3FASC and O6FASC, and the biological activities of these three compounds are presented. The O6FASC shows very good results in anti-inflammatory effects; the O3FASC has anti-stress activities, whereas the O9FASC presents interesting results in improving elasticity and firmness. All these activity tests are presented in this work.

Homogeneous distribution of fatty ester‐based active cosmetic ingredients in hydrophilic thin films by means of nanodispersion

“…Punicic acid, as every PUFA, can be easily oxidized in presence of water. Despite it was shown that the esterification of PUFAs could slow their oxidation [1], in aqueous nanodispersion, the risk of oxidation is high, because the surface of PHE contact with water is large. In order to reduce the risk of PHE oxidation, a-tocopherol (Vit E), a widely used lipophilic antioxidant, was added in DMC prior to nanoemulsification for an intimate mix with PHE.…”

“…Fatty acids (FAs) are well known in the cosmetic industry as emollients or functional ingredients used to texturize products. Lately, covalently bonding active cosmetic ingredients (ACI) to FAs represents a more and more developed way to enhance skin penetration of small hydrophilic active cosmetic ingredients and increase their activity [1,2]. Moreover, intrinsic properties of some FA, in particular that of polyunsaturated fatty acids (PUFAs), confer to cosmetic products antimicrobial [3], antioxidant [4] or anti-ageing [5] activity.…”

“…The resulting cosmetic active ingredient is prone to oxidation in the presence of light, water and oxygen mainly because of the reactivity of the three conjugated double bonds of the punicic chain ( Fig. 1) [1].…”

Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor

“…Starting from this overview, the aim of our work was to develop for the first time a continuous process for the efficient enzymatic production of 1-O,3-N-diacyl 3-amino-1,2propanediol-type pseudo-ceramides. These diacylated derivatives of 3-amino-1,2-propanediol have been considered in various studies as pseudo-ceramides for two reasons: i) their structure includes a polar head, two lipophilic carbon chains and an amide bond, and is thus very close to natural ceramide structure; ii) they have been demonstrated to have restructuring effects very similar to those of natural ceramides at the level of the uppermost skin layer, the socalled stratum corneum [12,26,32].…”

TEM Assessments of the Restructuring Effects of an Emollient Cream on the <i>stratum corneum</i>

“…Mixtures of ceramides, cholesterol and fatty acids allow the barrier function to repair [6]. Couturier and Yvergnaux (2009) showed that the supply of missing ceramides by topical administration results in relipidization of the stratum corneum and leads to the regeneration of physiological processes [7]. On this matter, Fartasch (1997) pointed out that the lipid-rich intercellular structures of the stratum corneum might influence the desquamation process [8].…”