Pseudomonas carvone

As mentioned before, a Pseudomonas incognita was isolated by enrichment technique on the monoterpene alcohol linalool that was also able to grow on geraniol, nerol and limonene [36]. The metabolism of limonene by this bacterium was also investigated [37]. After fermentation the medium yielded as main product a crystallic acid, perillic acid, together with unmetabolised limonene, and some oxygenated compounds dihydrocarvone, carvone, carveol, p-menth-8-en-1 -ol-2-one, p-menth-8-ene-1,2-diol or p-menth-1 -ene-6,9-diol (structure not fully elucidated) and finally / -isopropenyl pimelic acid. 

A Pseudomonas strain hydroxylates p-menthane to cis-p-menthan-l-ol,84 and microbiological reduction of carvotanacetone with Pseudomonas ovalis gives similar results85 to those obtained with carvone (Vol. 5, p. 24, incorrectly reports inversion at C-4). (—)-Carvotanacetone (30) gives (+)-carvomenthone (31), (—)-... 

Both naturally occurring enantiomers of carvone were selectively reduced by B. sulfurescens (Scheme 71). (-)-Carvone was reduced to (-h)-dihydrocarvone (trans) and further to (-H)-neodihydrocarveol, whereas (-i-)-carvone was reduced to (-)-isodihydrocarvone (cis), which was then converted to (-)-neo-isodihydrocarveol. Similar reductions with identical stereoselectivities were observed earlier with Pseudomonas ovalis (strain 6-1) and with a strain of Aspergillus niger. ... 

FIGURE 19.108 Metabolic pathways of (+)-carvone (93) by Pseudomonas ovalis strain 6-1 and other many microorganisms. (Modi ed from Noma. Y. et al., Agric. Biol. Chem., 38, 735,1974b.)... 

However, P. fragi IFO 3458, Pseudomonas fluorescens IFO 3081, and Aerobacter aerogenes IFO 3319 and IFO 12059 formed (-)-dihydrocarvone (101a) predominantly from (+) carvone (93). In the time course study of the biotransformation of (+)-carvone (93), it appeared that predominant formation of (-)-dihydrocarvone is due to the epimerization of (-)-isodihydrocarvone (101b ) by epimerase of P. fragi IFO 3458 (Noma et al., 1975). 

Noma, Y., 1977. Conversion of the analogues of carvone and dihydrocarvone by Pseudomonas ovalis, strain 6-1, Biochemical reduction of terpenes, part VII. 463-470. 

Noma, Y., S. Nonomura, H. Ueda, and C. Tatsumi, 1974c. Conversion of (+)-carvone by Pseudomonas ovalis, strain 6-1(1).38 735-740. 

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