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Valorisation De L'écorce De Picea Mariana Par La Valorisation de l’écorce de Picea mariana par la production d’extraits naturels : les extraits aqueux et l’huile essentielle Thèse Nellie Francezon Doctorat en Sciences du Bois Philosophiæ Doctor (Ph. D.) Québec, Canada © Nellie Francezon, 2018 Valorisation de l’écorce de Picea mariana par la production d’extraits naturels : les extraits aqueux et l’huile essentielle Thèse Nellie Francezon Sous la direction de : Tatjana Stevanovic, directrice de recherche Résumé L’épinette noire Picea mariana est une essence abondamment exploitée au Québec pour la qualité de son bois de charpente. Sa transformation par les scieries génère, en conséquence, d’énormes volumes d’écorces résiduelles. Dans un objectif de transformation de la ressource et de conception de produits et systèmes innovants, ce projet de doctorat a permis de développer un procédé de conversion de la biomasse forestière pour la valorisation complète de l’écorce de l’épinette noire, en utilisant des solvants respectueux de l’environnement. Ce procédé intègre deux types d’extractions différentes : l’hydrodistillation et l’extraction à l’eau chaude. Ainsi il produit simultanément trois extraits naturels, l’huile essentielle et l’hydrolat capturant la fragrance de l’épinette et l’extrait aqueux brut riche en polyphénols antioxydants. L’élucidation de la composition chimique de l’huile essentielle et de l’hydrolat d’écorce de l’épinette noire a mis en évidence plus de cinquante composés volatils et aromatiques appartenant à la famille des terpénoïdes. De plus, la fragrance de l’huile essentielle est très différente de celle produite industriellement à partir des aiguilles. Elle pourrait ainsi constituer un nouveau produit pour les secteurs de la parfumerie et des arômes. L’extrait brut aqueux, quant à lui, est riche en polyphénols antioxydants, en tanins et en sucres. Les composés phénoliques de faibles masses moléculaires appartiennent majoritairement à la famille des stilbènes dont les trans-isorhapontine, trans-resvératrol, trans-picéide et trans- astringine. Deux nouvelles molécules ont également été découvertes dans cet extrait : deux stéréoisomères de stilbènes, appelés picéasides O et P. Dans le but de récupérer ces molécules d’intérêt en plus grande quantité, une optimisation de l’extraction aqueuse a été réalisée pour établir les meilleurs paramètres d’extraction. La température 80 °C et le ratio écorce/eau 50 mg/mL ont été déterminés comme étant les paramètres les plus efficaces pour enrichir l’extrait aqueux en polyphénols d’intérêt, grâce à une approche statistique impliquant la chimiométrie. Ainsi, trois produits à haute valeur ajoutée sont disponibles à partir de l’écorce de l’épinette noire. Mais le plus pertinent au niveau industriel, c’est qu’ils peuvent être extraits simultanément via le procédé intégré dont le développement a permis de valider les iii rendements et les compositions chimiques tout en garantissant la disponibilité des écorces résiduelles pour la combustion. Ce projet de doctorat permet d’offrir une solution de gestion efficace des coproduits de transformation du bois par le biais d’un procédé vert produisant trois produits naturels à haute valeur ajoutée. Les extraits riches en polyphénols constitueraient de nouveaux ingrédients naturels potentiels pour les secteurs cosmétiques et de santé nutrition, en tant qu’actifs pour la peau ou compléments alimentaires antioxydants. De plus, les molécules d’intérêt thérapeutique comme le resvératrol et ses dérivés identifiés dans l’extrait aqueux seraient de bons candidats pour l’industrie pharmaceutique. Enfin, l’huile essentielle et l’hydrolat pourraient enrichir la palette du parfumeur ou être employés en tant qu’arômes. iv Abstract The transformation of black spruce Picea mariana, abundantly operated for the quality of its lumber in Quebec, generates huge volumes of residual bark in sawmills. With the objective of transforming the resource and designing innovative products and systems, this doctoral project has developed a process for converting forest biomass through the complete conversion of black spruce bark, using eco-friendly solvents. This process incorporating two different types of extractions (hydrodistillation and hot water extraction) simultaneously produces three natural extracts, the essential oil and hydrosol capturing the fragrance of black spruce and the hot water extract enriched with antioxidant polyphenols. The elucidation of the chemical composition of black spruce bark essential oil and hydrosol has revealed more than fifty volatile and aromatic compounds belonging to the terpenoid family. In addition, the fragrance of the essential oil is very different from the one produced industrially from the needles. It could thus constitute a new product for the perfume and aroma sectors. The aqueous crude extract, on the other hand, is rich in antioxidant polyphenols, tannins and sugars. Phenolic compounds of low molecular weight mainly belong to the stilbene family, including trans-isorhapontin, trans-resveratrol, trans-piceide and trans-astringin. Two new molecules have also been discovered in this extract: two stereoisomers of stilbene, called piceasides O and P. In order to optimally recover these molecules of interest, an optimization of the hot water extraction has made it possible to highlight the best extraction parameters. Thanks to a statistical approach involving chemometrics, the temperature 80 °C and the bark/water ratio 50 mg/mL were determined to be the most effective parameters for enriching the aqueous extract with polyphenols of interest. Thus, three high value-added products are extractable from the bark of black spruce. But the most interesting at an industrial level is that they can be extracted simultaneously via the integrated process whose development has validated the yields and chemical compositions while ensuring the availability of residual bark for combustion. This doctoral project offers a solution for an efficient management of co-products of wood processing through a green process, producing three natural products with high added value. v The cosmetic and health nutrition sectors, constantly in search of new natural ingredients, may be interested in marketing these extracts as skin actives or as antioxidant dietary supplements. Molecules of therapeutic interest such as resveratrol and its derivatives identified in the aqueous extract could also be used by the pharmaceutical industry. Essential oil and hydrosol could enrich the perfumer's palette or be used as aromas. vi Table des matières Résumé .................................................................................................................................. iii Abstract ................................................................................................................................... v Table des matières ................................................................................................................ vii Liste des figures ..................................................................................................................... xi Liste des tableaux ................................................................................................................ xiii Liste des abréviations .......................................................................................................... xiv Remerciements .................................................................................................................. xviii Avant-propos ....................................................................................................................... xix Introduction ............................................................................................................................ 1 Chapitre 1 Revue de littérature ............................................................................................... 3 1.1. Les écorces ....................................................................................................................... 3 1.2. Les extractibles forestiers ................................................................................................ 3 1.3. Les terpénoïdes ................................................................................................................ 4 1.3.1. L’oléorésine, la source des terpénoïdes ................................................................. 5 1.3.2. Voie de biosynthèse ............................................................................................... 6 1.3.3. Les monoterpénoïdes ............................................................................................. 7 1.3.4. Les sesquiterpénoïdes .......................................................................................... 10 1.3.5. Les diterpénoïdes ................................................................................................. 11 1.3.6. Les triterpénoïdes et tétraterpénoïdes .................................................................. 13 1.4. Les composés phénoliques ............................................................................................ 14 1.4.1. Voies de biosynthèse ........................................................................................... 14 1.4.2. Les phénols et acides phénols ............................................................................. 16 1.4.3. Les stilbènes ........................................................................................................ 17 1.4.4. Les lignanes
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