Biotransformation of limonene by bacteria, fungi, yeasts, and plants

Abstract

The past 5 years have seen significant progress in the field of limonene biotransformation, especially with regard to the regiospecificity of microbial biocatalysts. Whereas earlier only regiospecific biocatalysts for the 1,2 position (limonene-1,2-diol) and the 8-position (a-terpineol) were available, recent reports describe microbial biocatalysts specifically hydroxylating the 3-position (isopiperitenol), 6-position (carveol and carvone), and 7-position (perillyl alcohol, perillylaaldehyde, and perillic acid). The present review also includes the considerable progress made in the characterization of plant P-450 limonene hydroxylases and the cloning of the encoding genes.

Isolation and screening of d-limonene-resistant microorganisms

“…In this context, biotransformation process emerges as an attractive alternative for the d-limonene transformation since, comparing to the traditional chemical methods, they proceed under mild conditions, have an elevated regio and enantioselectivety, do not generate toxic wastes and the products obtained might be labeled as "natural" (13,17). In the scientific literature, the biotransformation of limonene by microorganisms has been well documented (12). However, a commercial process, which could be applicable and possess high productivity, is yet to be developed.…”

Formation of harmful compounds in biotransformation of lilial by microorganisms isolated from human skin

“…In a previous study carried out on the biotransformation of terpenoids by Bacillus stearothermophilus, the materials produced were perillyl alcohol, perillaldehyde, and a-terpineol (Duetz et al, 2003). Biotransformation of plasmid-controlled mercury by the bacteria Clostridium cochlearium (Pan-Hou et al, 1980) and of 2,4-dinitrotoluene and 2,6-dinitrotoluene by C. acetobutylicum (Hughes et al, 1999) has also been studied.…”

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

“…Studies on this theme included the use of a tubular segmented-flow biofilm reactor in a multistep process with high productivity [19]. Investigations have also been carried out with the bacteria Escherichia and Mycobacterium [16]. The fungus Aspergillus cellulosae [16] and the non-conventional yeasts Arxula adeninivorans and Yarrowia lipolytica [20] have also been approached to converting limonene to perillic derivatives.…”

“…Investigations have also been carried out with the bacteria Escherichia and Mycobacterium [16]. The fungus Aspergillus cellulosae [16] and the non-conventional yeasts Arxula adeninivorans and Yarrowia lipolytica [20] have also been approached to converting limonene to perillic derivatives. Recently, our research group successfully studied the bio-oxidation of R-(+)-limonene into R-(+)-perillic acid by Y. lipolytica ATCC 18942 [21], which is recognized as safe and suitable yeast to be used in processes aiming at products for human consumption [22] [23].…”

“…Nevertheless, several studies on the microbial or enzymatic bio-oxidation of limonene have shown effectiveness to oxyfunctionalize exclusively the exocyclic methyl group for the production of perillic acid [15] [16]. Biotransformation processes using wild type or genetically modified Pseudomonas putida cells have shown to be quite promising for the production of perillic acid as a molecule of industrial interest for natural preservation and pharmaceutical application [17] [18] [19].…”