Bioconjugation of Vegetable Oils with UV Absorbers: New Approach in Skin Photoprotection

Andrei Iulian Slabu; Laura Miu; Emilian Ghibu; Cristina Elena Stavarache; Raluca Stan; Florina Teodorescu

doi:10.3390/molecules28227550

Bioconjugation of Vegetable Oils with UV Absorbers: New Approach in Skin Photoprotection

Molecules. 2023 Nov 12;28(22):7550. doi: 10.3390/molecules28227550.

Authors

Andrei Iulian Slabu^{1

2}, Laura Miu^{1

2}, Emilian Ghibu^{1

2}, Cristina Elena Stavarache^{1

3}, Raluca Stan², Florina Teodorescu¹

Affiliations

¹ "C. D. Nenitzescu" Institute of Organic and Supramolecular Chemistry of the Romanian Academy, 202 B Spl. Independenței, S6, 060023 Bucharest, Romania.
² Faculty of Chemical Engineering and Biotechnologies, National University of Science and Technology Politehnica of Bucharest, 1-7 Gh. Polizu Street, 011061 Bucharest, Romania.
³ Advanced Polymer Materials Group, National University of Science and Technology Politehnica of Bucharest, 1-7 Gh. Polizu Street, 011061 Bucharest, Romania.

Abstract

We reported the tunable synthesis of new vegetable oil-UV filter bioconjugates using sea buckthorn oil (SBO) and p-methoxycinnamic acid (p-MCA) as an alternative to the common UV filter, ethylhexyl-p-methoxycinnamate (octinoxate). The synthetic strategy is based on the sustainable ring-opening reaction of epoxidized SBO with p-MCA in heterogenous catalysis in eco-friendly solvents. The amount of UV-absorptive moieties grafted on the triglyceride backbone is controlled by different epoxidation degrees as determined by NMR spectroscopy. The performance of the new UV-absorber bioconjugates was assessed by in vitro sun protection factor (SPF) measurements after inclusion in SBO-ethylcellulose (EC) oleogels and comparison with the SPF value of the SBO-EC-octinoxate oleogel with equivalent p-MCA acid moieties (10% wt/wt). The concentration obtained for the SBO-EC oleogel formulated with the bioconjugate with the lowest degree of functionalization, namely 55%, represents 45% of the SPF determined for the SBO-EC-octinoxate oleogel, regardless of the concentration of measured solutions. The new concept of vegetable oil-UV-absorber bioconjugates has potential UV-B photoprotective properties when included in oleogel formulations and deserves further investigation of their properties and stability including association with UV-A absorbers, respectively.

Keywords: bioconjugation; oleogel; p-methoxycinnamic acid; sea buckthorn oil; sun protection factor.

MeSH terms

Plant Oils* / chemistry
Skin
Sunscreening Agents* / chemistry
Sunscreening Agents* / pharmacology
Ultraviolet Rays

Substances

Plant Oils
octylmethoxycinnamate
Sunscreening Agents

Grants and funding

This work has been funded by the European Social Fund from the Sectoral Operational Programme Human Capital 2014–2020, through the financial agreement with the title “Training of Ph.D. students and postdoctoral researchers in order to acquire applied research skills—SMART”, Contract no. 13530/16 June 2022—SMIS code: 153734. Publishing costs are supported by the National University of Science and Technology POLITEHNICA of Bucharest, PubArt program.