Biotransformation of monoterpenoid ketones by yeasts and yeast-like fungi

Dyk, M. S. Van; Rensburg, Eugéne van; Rensburg, I.P.B.; Moleleki, Ntsane

doi:10.1016/s1381-1177(98)00024-1

Cited by 50 publications

(31 citation statements)

References 9 publications

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“…7-Hydroxypiperitone (2) was also obtained in the biotransformation of (2)-piperitone ( (2)-1) by yeasts and yeast-like fungi. 22,23 Yeast strains (Arxula spp., Yarrowia spp., Candida spp., and Debaryomyces spp.) gave 7-hydroxypiperitone (2) as the only product.…”

Section: Spectral Data Of Biotransformation Productsmentioning

confidence: 99%

“…The hydroxylation of (2)-piperitone ((2)-1) in the cis C-6 position by suspension cultured cells of Catharanthus roseus was reported by Hamada et al 12 The bioconversion of this substrate ((2)-1) into only one product-cis-6-hydroxypiperitone (4) by Hormonema sp., was also described. 22,23 The preparative biotransformation of piperitone ((6)-1) (120 mg) by A. coerulea AM93 after 9 days gave: 23 mg (17% isolated yield) of racemic (6)-7-hydroxypiperitone ((6)-2), 37 mg (28% isolated yield) of (2) A. coerulea AM93 showed lower activity for the hydroxylation of the studied substrate than A. cylindrospora AM336. The biotransformation of (6)-1 by this microorganism proceeded very slowly, and (R) isomer of substrate was transformed as the first one.…”

Section: Spectral Data Of Biotransformation Productsmentioning

confidence: 99%

“…2,3,[5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] The substrates and products of these transformations are components of many essential oils of plants, and they are also important for flavor and fragrance industry. 2,3,19,24 Hydroxylation at allylic position of a,b-unsaturated monoterpene ketones by microorganisms 15,16,20,22,23 and plant cell cultures [12][13][14]18 has been well documented. Piperitone, a monoterpene ketone, is the major constituent of essential oils from some Eucalyptus, Mentha, and Cymbopogon species.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselectivity of hydroxylation of racemic piperitone by fungi

2010

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The biotransformation of racemic piperitone ((±)-1) was investigated using four strains of fungi selected in the screening procedure. The substrate was transformed by Botrytis cinerea AM235, Absidia cylindrospora AM336, Absidia coerulea AM93, and Absidia glauca AM177 into more polar metabolites. The transformation of racemic piperitone ((±)-1) catalyzed by B. cinerea AM235 gave 7-hydroxypiperitone (2) as the only product. The biotransformation of (±)-1 by A. cylindrospora AM336 afforded mixture of three products: (-)-(R)-7-hydroxypiperitone ((-)-2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), and (+)-(4R,6R)-cis-6-hydroxypiperitone ((+)-4). The transformation of this substrate ((±)-1) by A. coerulea AM93 gave (±)-7-hydroxypiperitone ((±)-2), (-)-(4R,6S)-trans-6-hydroxypiperitone (-)-3), and (-)-(4S,6S)-cis-6-hydroxypiperitone ((-)-4). The last strain studied, A. glauca AM177, converted racemic piperitone ((±)-1) to four products: (+)-(S)-7-hydroxypiperitone (2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), (±)-cis-6-hydroxypiperitone ((±)-4), and 8-hydroxypiperitone (5).

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Section: Spectral Data Of Biotransformation Productsmentioning

confidence: 99%

Section: Spectral Data Of Biotransformation Productsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioselectivity of hydroxylation of racemic piperitone by fungi

2010

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“…In fungi, enoate reductases are responsible for the reduction of activated C=C bonds. The enzymes responsible for the reduction of carvone are apparently present in many yeasts, fungi, plants, and algae [10]. Methylethenyl group reduction and hydroxylated derivatives were not found in the metabolism of carvone by Chlorella vulgaris.…”

mentioning

confidence: 94%

“…It is interesting to note that Chlorella vulgaris reduced the carbonyl group and the exocyclic C=C bond of the 1-methylethenyl group in (+)-pulegone to give menthol. Van Dykcs group [10] showed that the black yeast Hormonema sp. could transform (+)-pulegone to neomenthol.…”

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confidence: 99%

Biotransformation of some monoterpenoid ketones by Chlorella vulgaris MCCS 012

et al. 2010

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Biotransformation of several monoterpene ketones, including carvone, pulegone, piperitone, menthone, and fenchone, was carried out by the locally isolated unicellular microalgae Chlorella vulgaris. The microalgal strain was isolated during a screening program from soil samples collected from paddy-fields of Fars Province, in the south of Iran. Chlorella vulgaris was cultured in 250 mL conical flasks, each containing 50 mL of BG-11 liquid medium and 20 PL levels of terpene substrates, incubated at a temperature of 28r2qC and illuminated continuously with fluorescent lamps with shaking at 80 rpm. The metabolites were identified by thin-layer chromatography and GC-MS. Chlorella vulgaris has the ability to reduce the C=C double bond of carvone to yield trans-dihydrocarvone and cis-dihydrocarvone. The cell line reduced menthone and pulegone to the same product and gave menthol. Study of Chlorella vulgaris with substrates of piperitone and fenchone showed no reaction in these substrates. Chlorella vulgaris MCCS 012 was assigned according to the 18S rRNA gene sequence. The DNA sequence of the 18S rRNA gene of Chlorella vulgaris MCCS 012 was recorded in the NCBI under the accession number EU374170.

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Biocatalysis in Water

Nakamura¹,

Matsuda²

2007

Organic Reactions in Water

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Biotransformation of monoterpenoid ketones by yeasts and yeast-like fungi

Cited by 50 publications

References 9 publications

Enantioselectivity of hydroxylation of racemic piperitone by fungi

Enantioselectivity of hydroxylation of racemic piperitone by fungi

Biotransformation of some monoterpenoid ketones by Chlorella vulgaris MCCS 012

Biocatalysis in Water

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