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Synthesis of the Prospective Anticancer Molecule perillic Acid from Orange Essential Oil by the Yeast <i>Yarrowia lipolytica</i>

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Green and Sustainable Chemistry 2017年第2期7卷 172-184页

作者： Marcelo R. R. Tappin Felipe M. Knopp Igor C. Cardoso Roberta T. Santos Bruna S. Drummond Antonio C. Siani Elba P. S. Bon Maria Antonieta Ferrara Institute of Drug Technology Oswaldo Cruz Foundation Rio de Janeiro Brazil Chemistry Institute Federal University of Rio de Janeiro Rio de Janeiro Brazil

The bioconversion of the hydrophobic and volatile limonene to perillic acid, a potential anticancer agent, by the yeast Yarrowia lipolytica was studied in two steps. Firstly, experimental design was used for process optimization using high-purity limonene as substrate and secondly orange essential oil containing 89.1% limonene was used as substrate under the previously optimized conditions. Limonene concentration and pH were identified by fractional factorial design as significant factors and were optimized by central composite design. Under optimized process conditions (0.16% (v/v) limonene;pH 6.9), the 24 h biotransformation process resulted in the accumulation of 0.368 g·L-1 of perillic acid corresponding to a molar yield of 23.1%. A subsequent substrate addition under the same reaction conditions doubled perillic acid concentration to 0.793 g·L-1 and a molar yield of 24.2%. The use of orange essential oil under the optimized reaction conditions increased both perillic acid accumulation and yield to 0.872 g·L-1 and 29.7%, respectively. The robustness of Y. lipolytica allowed the efficient biotransformation of a crude by-product of the citrus industry into a valuable fine chemical.

关键词： Yarrowia lipolytica Bioconversion perillic Acid Limonene Orange Essential Oil

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Determination of perillic Acid in Bioconversion Supernatants by Gas Chromatography

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American Journal of Analytical Chemistry 2017年第10期8卷 636-644页

作者： Eliane G. Carvalho Antonio C. Siani Igor C. Cardoso Virginia Garcia Correia Maria A. Ferrara Elba P. S. Bon Marcelo R. Romero Tappin Medicine and Drug Technology Institute Oswaldo Cruz Foundation Rio de Janeiro Brazil Chemistry Institute Federal University of Rio de Janeiro Rio de Janeiro Brazil

perillic acid can be obtained from microbial oxidation of the exocyclic methyl group of limonene. Due to the pharmacological potential of such a metabolite, the biotransformation processes leading to its synthesis have been approached in recent studies. A robust analytical method is needed to assess the performance of such studies. An analytical method was developed and validated to determine perillic acid in the supernatants of a yeast-induced bioconversion of limonene, involving gas chromatography (GC) and an acid-induced precipitation during the sample preparation. GC analysis was performed using a column with polyethylene glycol as stationary phase (HP-Innowax) which resulted in higher loads and better peak shape. The sample preparation involved the supernatant initial filtration and precipitation with 0.6 M HCl followed by centrifugation and dissolution in ethyl acetate. GC analysis conditions were oven from 50°C to 250°C at 20°C·min-1, and then held 5 min (total runtime 15 min). Injector was set at 280°C, and detector at 300°C. Helium was the carrier gas at 1 ml·min-1. Injections of 1.0 μl were at the split ratio 25:1. The method was validated: Linearity with R2 of 0.9992, Accuracy of 98.3% in the range 190 - 950 μg·ml-1;Limit of detection of 10.4 μg·ml-1;Repeatability of 2.1% RSD. Thus, a complete methodology to determine perillic acid in a bioconversion supernatant was developed and validated. This overall approach may be useful for bioconversions of monoterpenes by other microorganisms that metabolize limonene.

关键词： Limonene perillic Acid Sample Preparation Gas Chromatography

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