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DOCTORAL THESIS Taofiq Ayodele Oludemi

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DOCTORAL THESIS Taofiq Ayodele Oludemi FACULTAD DE FARMACIA DEPARTAMENTO DE QUÍMICA ANALÍTICA, NUTRICIÓN Y BROMATOLOGÍA Development of cosmeceutical formulations based on mushroom extracts and their individual compounds DOCTORAL THESIS Taofiq Ayodele Oludemi Supervisors Dr. Isabel Cristina Fernandes Rodrigues Ferreira Dr. Maria Filomena Barreiro Dr. Ana María González Paramás Salamanca, 2019 Aknowledgements ACKNOWLEDGEMENTS First and foremost, I would like to extend my heartfelt gratitude to my supervisor Prof. Isabel C.F.R Ferreira for giving me the opportunity to be part of this amazing team. You have been very influential in my development as a researcher and as an individual. It is an honour to have the opportunity to learn from you and I will be forever grateful for all your efforts, unending support and continuous encouragement throughout my years of study. Your passion and enthusiasm towards science has been an inspiration to me. My sincere gratitude also goes to my co-supervisor Prof. Maria Filomena Barreiro for your advices and encouragement. I greatly benefited from your keen scientific insight, vast knowledge and scientific curiosity. You have been helpful and gave all necessary information towards the successful completion of this project. My profound gratitude also goes out to my co-supervisor Prof. Ana Maria González- Paramás for your guidance and support all through these years. Thank you so much for always finding the time to provide valuable comments and contributions towards the successful completion of this project. My gratitude also goes out to Dr. Lillian Barros for your continuous support, motivation and patience. Your work ethics have been a continuous source of inspiration to me and I am sincerely thankful for all your time and advices over the years. My sincere appreciation also goes out to Prof. Celestino Santos-Buelga, from Unidad de Nutrición y Bromatología, Faculty of Pharmacy, University of Salamanca, I want to thank you for your advices and continuous support. I would also like to appreciate the effort of Dr. Sandrina Heleno and Dr. Ricardo Calhelha. You both have contributed immensely towards achieving this goal. You have been patient and continue to offer advices whenever the need arises. Thank you so much for everything. My profound gratitude also goes out to all members of Biochemcore research group. Thank you so much for your friendship, assistance and scientific discussions. You have provided a wonderful environment for me to learn and this has really helped me. My gratitude also goes out to members of the Laboratory of Separation and Reaction Engineering (LSRE) especially Dr. Isabel Fernandes. You have been very helpful towards the course of this project. My gratitude also goes out to members of the REQUIMTE/LAQV, iii Aknowledgements Department of Chemical Sciences, Faculty of Pharmacy, University of Porto especially Prof. Beatriz P.P. Oliveira and Dr. Francisca Rodrigues, for welcoming me so well during my research stay at the University of Porto. To the Instituto Politécnico de Bragança especially Dr. Luis Pais and Dr. Anabela Martins, I want to say a big thank you for supporting me all through my time in Braganca. Thank you so much for been there for me and I am glad to be part of this great Institute. My appreciation also goes out to the Foundation for Science and Technology (FCT) for financial support to the Centro de Investigação de Montanha (CIMO) and making it a wonderful and well-equipped environment to develop my work. I would like to offer special thanks to Babatunde Ayodele Osinowo, who, although is no longer with us, has supported me greatly over the years. Thank you so much for everything and I pray you continue to rest in peace. I have met wonderful friends over the years, and I want to say a big thank you to them all, especially Sankara Unisa-Kamara and Karl Mokake Njomo, I really appreciate you guys for the love, friendship and support. My gratitude also goes to my mum Alhaja Ramat Oludemi for your continuous encouragement, prayers and support over the years. Thank you so much for everything you have done in my life, you are my champion and I owe so much to you. To my siblings and my family, I am sincerely grateful for your encouragement and moral support. To my beloved wife, Simbiat Olaide Jimoh, you have been my support system over the years. Even when times looked gloomy, your continuous optimism, understanding and encouragement have been my pillar and I want to sincerely thank you for being a part of my life. Finally, my greatest appreciation goes to Almighty Allah (S.W.T) for sparing my life and for taking complete control over my family, my health, my education, my career and every aspect of my life. All praise is due to you, the Lord of the world, the most Beneficent and the most Merciful. iv Abstract ABSTRACT The cosmetic industry is constantly in search of ingredients from natural sources because of their multifunctional properties, competitive effectiveness, and lower toxicity effects. Otherwise, mushrooms have been an important part of our diet for years due to their rich nutritional and abundant content in biomolecules; however, their cosmeceutical and nutricosmetic potential have not been fully exploited. This study aimed at optimizing the extraction of bioactive compounds from Ganoderma lucidum and Agaricus blazei by Response Surface Methodology (RSM) and comparing conventional extraction techniques with more sustainable methods. Further studies regarding their nutritional and chemical composition (e.g., sugars, organic acids, tocopherols, and fatty acids), were conducted. Also, extracts obtained from those mushrooms, but also from Agaricus bisporus, Pleurotus ostreatus and Lentinula edodes extracts, using the Soxhlet extraction system, were analysed in terms of anti- inflammatory, anti-tyrosinase, antioxidant, and antimicrobial activities followed by their characterization in terms of phenolic acids and related compounds, ergosterol, and triterpenoids. Furthermore, the obtained extracts were incorporated in a base cosmetic cream to ascertain bioactive properties sustainment. Moreover, to evaluate the individual cosmeceutical contribution of p-hydroxybenzoic acid, p-coumaric acid, protocatechuic acid, cinnamic acid and ergosterol, their anti-inflammatory, anti-tyrosinase, and antimicrobial activities were studied, followed by incorporation of these compounds in a base cosmetic cream. Because of the possibility of the extracts and the individual compounds to lose their potency over time either due to oxidation or degradation, microparticles were prepared using the atomization/coagulation technique. The microparticles were characterized in terms of morphology, particle size distribution, and encapsulation efficiency. This is followed by incorporation of the produced microparticles into a base cosmetic cream and comparison of their performance with the free forms (formulations containing free extracts/individual compounds). The most promising extracts and their corresponding formulations were submitted to in vitro safety evaluation using the MTT and LDH assays in keratinocyte (HaCaT) and fibroblast (HFF-1) cell lines. Moreover, they were submitted to ex vivo skin permeation studies using a Franz diffusion apparatus with pig ear skin as permeation membrane to determine topical bioavailability of the bioactive compounds present in the extracts. The optimization study on bioactive compounds recovery from G. lucidum and A. blazei using RSM showed that the values predicted by the models were in close agreement with vi Abstract experimental observations. Furthermore, it was concluded that the extraction yield of bioactive compounds from the studied mushrooms was highly dependent on the extraction variables (time, temperature, solvent proportion, solid-liquid ratio, and power). A. blazei and G. ludidum also showed high nutritional contribution. α-Tocopherol, oxalic acid and twenty-one fatty acids (mainly PUFA) were quantified in A. blazei. G. lucidum showed a similar fatty acids’ profile (PUFA˃SFA˃MUFA) and with the presence of α-tocopherol and δ-tocopherol. Comparatively, A. blazei revealed lower fat content, but higher energy contribution. The cell viability effect of the extract prepared from A. blazei on Caco-2 and HT29-MTX cells was found to be maintained in a concentration-dependent manner. The ethanolic extracts obtained from the studied mushrooms showed antioxidant, anti- inflammatory, anti-tyrosinase and antimicrobial activities, and after incorporation into the base cosmetic cream, the final cosmeceutical formulations preserved some of these bioactivities. G. lucidum extract was found to be a rich source of triterpenoids mainly due to the high contribution of ganoderic acid A, C2, and H, while phenolic acids (p-hydroxybenzoic acid, p- coumaric acid and protocatechuic acid), the related compound cinnamic acid, and ergosterol were identified in A. bisporus, P. ostreatus, L. edodes and A. blazei extracts. Each one of these compounds also showed anti-inflammatory, anti-tyrosinase and antimicrobial activities. Furthermore, microparticles were successfully used to encapsulate extract/individual compounds with high encapsulation efficiency and yield. After incorporation of the free extracts/individual compounds and the produced microparticles into the base cosmetic cream, the encapsulated forms allowed for a controlled release leading to bioactivity preservation when compared with the free forms. Because they presented the most interesting cosmeceutical potential, P. ostreatus and G. lucidum extracts
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