Access to Oxygenated Monoterpenes via the Biotransformation of ( R )-Limonene by Trichoderma harzianum and Saccharamyces
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ORIGINAL ARTICLE
Access to Oxygenated Monoterpenes via the Biotransformation of (R)‑Limonene by Trichoderma harzianum and Saccharamyces cerevisiae Enis Ben Bnina1 · Majda Daami‑Remadi2 · Hichem Ben Jannet1 Received: 27 April 2020 / Accepted: 9 June 2020 © The Tunisian Chemical Society and Springer Nature Switzerland AG 2020
Abstract Microbial biotransformation is a pertinent strategy to overcome difficulties and problems arising from the chemical synthesis, in order to have access to regiospecific and stereospecific compounds and also explain the inactivity of essential oils or chemicals against some microorganisms. We evaluate in this research work, the bioconversion of (R)-limonene dominating the chemical composition of peels essential oil of the Tunisian Citrus aurantium by Trichoderma harzianum and Saccharomyces cerevisiae. In order to understand the exact and specific effects of these two yeasts on (R)-limonene, a negative control in the presence of air oxygen was carried out. Six oxygenated monoterpenes were produced and identified by GC–MS. Following the same protocol in the presence of these two yeasts, eight and seven secondary metabolites were formed, respectively. The results showed specific bioconversions and the fungi used involved to complete the full conversion of limonene and catalyze certain successive reactions in a specific way. Keywords Bioconversion · Oxygenated monoterpenes · (R)-limonene · Saccharomyces cerevisiae · Trichoderma harzianum
1 Introduction Limonene (4-isopropenyl-1-methylcyclohexene) is a natural monocyclic monoterpene very attractive, renewable resource [1] and the most abundant structure and it is widely available as a hydrocarbon monoterpene in the world belonging to the family of terpenoids which represent the largest class of secondary plant metabolites. Its derivatives are numerous and widely studied [1–3]. In recent years, much research has been carried out on the metabolism of terpenoids; mainly limonene which is known by its various biological activities such as cytotoxicity [4], * Hichem Ben Jannet [email protected] 1
Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia
UR13AGR09-Intergrated Horticultural Production in the Tunisian Centre-East, Regional Research Centre on Horticulture and Organic Agriculture, Chott‑Mariem, 4042 Sousse, Tunisia
2
hypoglycemic [5], anti-inflammatory [5, 6], antioxidant [6, 7] antitumoral [8], antifungal [9], antibacterial [10] and an effect protective against oxidative stress [11]. Chemically, it was used as a precursor in many reactions affording new molecules used in several application fields [12, 13], as flavors and fragrances for perfume and cosmetic products [1], as drugs in the pharmaceutical industry [14] and in the petrochemical industry [15]. For biotransformation, it was studied with various microorganisms (bacteria, yeasts and fung
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