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Review
. 2022 Jul 5:10:886367.
doi: 10.3389/fchem.2022.886367. eCollection 2022.

From Biomass-Derived p-Hydroxycinnamic Acids to Novel Sustainable and Non-Toxic Phenolics-Based UV-Filters: A Multidisciplinary Journey

Benjamin Rioux  1 , Jeanne Combes  1 , Jack M Woolley  2 , Natércia D N Rodrigues  2   3 , Matthieu M Mention  1 , Vasilios G Stavros  2 , Florent Allais  1
Affiliations
Review

From Biomass-Derived p-Hydroxycinnamic Acids to Novel Sustainable and Non-Toxic Phenolics-Based UV-Filters: A Multidisciplinary Journey

Benjamin Rioux et al. Front Chem. .

Abstract

Although organic UV-filters are extensively used in cosmetics to protect consumers from the deleterious effects of solar UV radiation-exposure, they suffer from some major drawbacks such as their fossil origin and their toxicity to both humans and the environment. Thus, finding sustainable and non-toxic UV-filters is becoming a topic of great interest for the cosmetic industry. A few years ago, sinapoyl malate was shown to be a powerful naturally occurring UV-filter. Building on these findings, we decided to design and optimize an entire value chain that goes from biomass to innovative biobased and non-toxic lignin-derived UV-filters. This multidisciplinary approach relies on: 1) The production of phenolic synthons using either metabolite extraction from biomass or their bioproduction through synthetic biology/fermentation/in stream product recovery; 2) their functionalization using green chemistry to access sinapoyl malate and analogues; 3) the study of their UV-filtering activity, their photostability, their biological properties; and 4) their photodynamics. This mini-review aims at demonstrating that combining biotechnology, green chemistry, downstream process and photochemistry is a powerful approach to transform biomass and, in particular lignins, into high value-added innovative UV-filters.

Keywords: Knoevenagel; UV-filter; biotechnology; green chemistry; in stream product recovery; p-hydroxycinnamic acids; photodynamics; synthetic biology.

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Conflict of interest statement

Author NR is employed by Lipotec. The remaining authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
p-Hydroxycinnamic acids biosynthesis pathway. (PAL: phenylalanine ammonia-lyase, TAL: tyrosine ammonia-lyase, C4H: cinnamate-4-hydroxylase, C3H: p-coumarate-3-hydroxylase, COMT: caffeic acid O-methyl transferase, F5H: ferulic-5-hydroxylase).
FIGURE 2
FIGURE 2
Continous recovery through liquid-liquid extraction (from Combes et al., 2021).
SCHEME 1
SCHEME 1
Synthesis of p-hydroxycinnamic acids (1) and their derivatives: p-hydroxycinnamic diacids (2), p-hydroxycinnamic esters (3), β-β dimers (4), p-hydroxycinnamyl barbiturics (5), and p-hydroxycinnamyl Meldrum’s (6) (R1 and R2 = H, OH or OMe).
FIGURE 3
FIGURE 3
UV-Vis spectra in EtOH (C = 10 µM) of each series of p-hydroxycinnamic derivatives with octinoxate as reference and their respective loss of absorbance upon 1 h of UV radiation (λ = 300 nm, p = 8.32 W/m2, stirring, T = 35°C).
FIGURE 4
FIGURE 4
Examples of EC50 for each series of p-hydroxycinnamic acids derivatives relating to free radical inhibition in ethanol, compared to antioxidants conventionally used: BHA and BHT.
FIGURE 5
FIGURE 5
Examples of EC50 for the p-hydroxycinnamyl Meldrum’s series compared to Kojic acid for mushroom tyrosinase inhibition.
FIGURE 6
FIGURE 6
Receptor activity (%) of estrogen receptor α (ERα), androgen receptor (AR) and pregnane X receptor (PXR) concerning agonist (A) and antagonist (B) interactions of p-hydroxycinnamic esters at 10 μM.
FIGURE 7
FIGURE 7
Molecular structures of the compounds studied in the case studies presented in this section, namely (A) (i) Z-Ethyl Sinapate and (A) (ii) E-Ethyl Sinapate, (B) Diethyl Sinapate, (C) (i) Coumaryl Meldrum and (C) (ii) Sinapoyl Meldrum.
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