Production of aromas and fragrances through microbial oxidation of monoterpenes

• Main Authors: H. F. Rozenbaum, M. L. Patitucci, O. A. C. Antunes, N. Pereira Jr
• Format: Article
• Language: English
• Published: Brazilian Society of Chemical Engineering 2006-09-01
• Series: Brazilian Journal of Chemical Engineering
• Subjects: Bayer-Villiger; Cytochrome P450; Oxidation; Verbenone; Alpha-terpineol
• Online Access: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0104-66322006000300001

Aromas and fragrances can be obtained through the microbial oxidation of monoterpenes. Many microorganisms can be used to carry out extremely specific conversions using substrates of low commercial value. However, for many species, these substrates are highly toxic, consequently inhibiting their metabolism. In this work, the conversion ability of Aspergillus niger IOC-3913 for terpenic compounds was examined. This species was preselected because of its high resistance to toxic monoterpenic substrates. Though it has been grown in media containing R-limonene (one of the cheapest monoterpenic hydrocarbons, which is widely available on the market), the species has not shown the ability to metabolize it, since biotransformation products were not detected in high resolution gas chromatography analyses. For this reason, other monoterpenes (alpha-pinene, beta-pinene and camphor) were used as substrates. These compounds were shown to be metabolized by the selected strain, producing oxidized compounds. Four reaction systems were used: a) biotransformation in a liquid medium with cells in growth b) with pre-grown cultures c) with cells immobilized in a synthetic polymer network and d) in a solid medium to which the substrate was added via the gas phase. The main biotransformation products were found in all the reaction systems, although the adoption of previously cultivated cells seemed to favor biotransformation. Cell immobilization seemed to be a feasible strategy for alleviating the toxic effect of the substrate. Through mass spectrometry it was possible to identify verbenone and alpha-terpineol as the biotransformation products of alpha-pinene and beta-pinene, respectively. The structures of the other oxidation products are described.