Biotransformation of limonene and related compounds by Aspergillus cellulosae

Noma, Yoshiaki; Yamasaki, Sumika; Asakawa, Yoshinori

doi:10.1016/0031-9422(92)83619-a

Cited by 65 publications

(34 citation statements)

References 5 publications

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“…Furthermore, monoterpene toxicity might depend on their droplet size in suspension, as observed for Saccharomyces cerevisae (28). In biotransformation processes, the usual limonene concentration applied vary from 0.2 to 1% (3,10,11,22,24,27,29), although 0.2% limonene is the optimum concentration for its biotransformation to perillyl alcohol and p-ment-1-ene-6,8-diol using Pseudomonas putida (7) and is toxic to Bacillus stearothermophilus (4).…”

Section: Limonene Resistant Microorganismsmentioning

confidence: 99%

Isolation and screening of d-limonene-resistant microorganisms

Bicas

Pastore

2007

Braz. J. Microbiol.

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This study reports the isolation of microorganisms that are resistant to environment containing limonene, the most important residue in the citrus industry. For the isolation, samples collected from strategic places of a citrus processing plant (yellow water, entrance and exit of the bagasse tank, effluent and deteriorated fruits found in bins, machine straps, fruit washers and plant floor), some citrus fruit and mint from local market were used. The samples were incubated in rotary shaker at 30ºC/150rpm for 48h or 7 days in YM medium containing 0.1% limonene. Great part of the 112 strains recovered after 48h and the 126 strains recovered after 7 days were identified as Gram positive bacilli, followed by Gram negative bacilli, yeasts and Gram positive cocci, besides five fungi. About half of the Gram positive and Gram negative bacilli and yeasts and some Gram positive Cocci were resistant to limonene concentrations up to 2% in the medium broth. Amongst them seventy were able to grow in mineral medium containing limonene as sole carbon source. The research described in this paper is the initial step for the exploration of flavor compounds production via biotransformation of limonene, a nonexpensive by-product of citrus industry.

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Section: Limonene Resistant Microorganismsmentioning

confidence: 99%

Isolation and screening of d-limonene-resistant microorganisms

Bicas

Pastore

2007

Braz. J. Microbiol.

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“…The carveol formed was partially oxidized further to carvone (Onken and Berger 1999). The P-450 systems from Aspergillus cellulosae M-77 did not display a high degree of regiospecificity and resulted in the formation of a mixture of isopiperitenone, limonene-1,2 trans diol, cis-carveol, perillyl alcohol, isopiperitenol, and a-terpineol (Noma et al 1992) A Penicillium digitatum strain isolated from overripe oranges converted limonene to cis-and trans-carveol, carvone, limonene-4-ol, and cis-and trans-mentha-2,8-dien-1-ol as major products (Bowen 1975). Finally, the honey fungus Armillareira mellae was reported to transform d-limonene to a-terpineol and limonene-1,2-diol (Draczynska 1987).…”

Section: Bioconversions By Fungi and Yeastsmentioning

confidence: 99%

“…Although there are some examples of micro-organisms that carry out such oxidations with rather high specificity (Table 1), many other micro-organisms oxidize limonene with a low specificity, leading to a large number of unwanted side products (Chang and Oriel 1994;Kieslich et al 1986;Noma et al 1992).…”

Section: Plant Enzymesmentioning

confidence: 99%

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

Duetz

Bouwmeester²,

Beilen

et al. 2003

Appl Microbiol Biotechnol

231

147

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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.

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“…Microbial strains found so far to be capable of bioconversion of D-limonene generally yielded a mixture of oxidation products (reviewed in reference 23). Recent examples are the conversion of D-limonene to ␣-terpineol and 6-hydroxycarveol by the honey fungus Armillareira mellae (9); to isopiperitenone, limonene-1,2 trans-diol, cis-carveol, perillyl alcohol, isopiperitenol, and ␣-terpineol by Aspergillus cellulosae (24); to carveol, ␣-terpineol, perillyl alcohol, and perillyl aldehyde by Bacillus stearothermophilus BR388 (4); and the same conversions by an Escherichia coli construct containing a plasmid with chromosomal inserts from this strain (3,5). The most regiospecific microbial biocatalysts described so far are the basidiomycete Pleurotus sapidus, which converts D-limonene to cis-and trans-carveol and carvone at a low rate (25), and the black yeast Hormonema sp.…”

Section: U (G Of Cells [Dry Weight])mentioning

confidence: 99%

Biotransformation of d -Limonene to (+) trans -Carveol by Toluene-Grown Rhodococcus opacus PWD4 Cells

Duetz

Fjällman

Ren

et al. 2001

Appl Environ Microbiol

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The toluene-degrading strain Rhodococcus opacus PWD4 was found to hydroxylate D-limonene exclusively in the 6-position, yielding enantiomerically pure (؉) trans-carveol and traces of (؉) carvone. This biotransformation was studied using cells cultivated in chemostat culture with toluene as a carbon and energy source. The maximal specific activity of (؉) trans-carveol formation was 14. U (g of cells [dry weight])؊1 , and the final yield was 94 to 97%. Toluene was found to be a strong competitive inhibitor of the D-limonene conversion. Glucose-grown cells did not form any trans-carveol from D-limonene. These results suggest that one of the enzymes involved in toluene degradation is responsible for this allylic monohydroxylation. Another toluene degrader (Rhodococcus globerulus PWD8) had a lower specific activity but was found to oxidize most of the formed trans-carveol to (؉) carvone, allowing for the biocatalytic production of this flavor compound.D-Limonene is the main constituent of orange and lemon peel oil (92 to 96% [26]), which is a by-product of the fruit juice industry produced in quantities of approximately 50,000 tons per year (25). Due to its low price, which varied between $0.66 and $1.45 per kg in the first half of 2000 (22), D-limonene is an attractive starting compound for industrially relevant fine chemicals and flavor compounds with identical carbon skeletons, such as carveol, carvone, and perillyl alcohol (Fig. 1). The regiospecific introduction of carbonyl or hydroxy groups by chemical catalysis, however, is difficult because the electronic properties of the allylic methylene groups (carbons 3 and 6) and the allylic methyl groups (carbons 7 and 10) are rather similar. For this reason, enzymatic oxidation was considered as early as the 1960s (7, 8), and numerous D-limonene-transforming microbial and plant cells have been described since. To date, the enzymes with the best regiospecificity have been derived from plants. The P450 enzymes limonene-3-hydroxylase and limonene-6-hydroxylase (isolated from peppermint and spearmint microsomes) convert their natural substrate Llimonene and-at lower rates-D-limonene to isopiperitenol and carveol, respectively (6,17,19). Another example is the oxidation of D-limonene in the 6 position to cis-and transcarveol and carvone by Solanum aviculare and Dioscorea deltoidea (29). The specific activities of these plant enzymes, however, are insufficient for industrial applications. Microbial strains found so far to be capable of bioconversion of D-limonene generally yielded a mixture of oxidation products (reviewed in reference 23). Recent examples are the conversion of D-limonene to ␣-terpineol and 6-hydroxycarveol by the honey fungus Armillareira mellae (9); to isopiperitenone, limonene-1,2 trans-diol, cis-carveol, perillyl alcohol, isopiperitenol, and ␣-terpineol by Aspergillus cellulosae (24); to carveol, ␣-terpineol, perillyl alcohol, and perillyl aldehyde by Bacillus stearothermophilus BR388 (4); and the same conversions by an Escherichia coli construct contain...

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Biotransformation of limonene and related compounds by Aspergillus cellulosae

Cited by 65 publications

References 5 publications

Isolation and screening of d-limonene-resistant microorganisms

Isolation and screening of d-limonene-resistant microorganisms

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

Biotransformation of d -Limonene to (+) trans -Carveol by Toluene-Grown Rhodococcus opacus PWD4 Cells

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