Extractives of fungi. V. Microbial transformation products of piperitone

Abstract

The products obtained from the transformation of (�)-piperitone (1) by Pro-actinomyces roseus, a species of Fusarium, and Aspergillus niger have been examined. Major transformation products include (�)-trans-6- hydroxy-p-menth-1-en-3-one (2) and (�)-7-hydroxy-p-menth-1-en-3-one (3); a minor transformation product has been tentatively identified as (�)-8-hydroxy-p-menth-1-en-3-one (4).

Enantioselectivity of hydroxylation of racemic piperitone by fungi

“…Lassak et al obtained 7-hydroxypiperitone (2) in the result of biotransformation of racemic piperitone ( (6)-1) by three, other than Absidia and Botrytis, fungi species (Aspergillus niger, Proactinomyces roseus, and Fusarium sp.). 15 They did not observe any enantioselectivity of these processes. 7-Hydroxypiperitone (2) was also obtained in the biotransformation of (2)-piperitone ( (2)-1) by yeasts and yeast-like fungi.…”

“…Piperitone, a monoterpene ketone, is the major constituent of essential oils from some Eucalyptus, Mentha, and Cymbopogon species. 25,26 According to the literature data, the hydroxylation of piperitone by fungi, 15 plants, 12 yeasts, and yeast-like fungi 22,23 was observed. However, the enantioselectivity of these processes was not investigated.…”

“…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.…”

“…[1][2][3][4] A variety of biocatalysts (enzymes, fungi, plants, bacteria, cyanobacteria, microalgae, and yeasts) were used for the transformation of exogenous substrates by regioand stereoselectively introduction of hydroxy group at various positions in the molecules of many monoterpenes. 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.…”

Acyloin condensation of acyclic unsaturated aldehydes byMucor species

“…(Ohloff et al 1964); 3 mg 3-oxo-l-menthen-7-ol (22) (0.2% th.) (Lassak et al 1973);134mg (2S,3R)-5,9-dimethyl-deca-4E,8E-dien-2,3-diol (23) 589nm 578nm 546nm _11.3 ° _11.9 ° _13.5 ° (c= 7.68, CHCI3); (2S,3R)-5,9-dimethyl-deca-4E,8E-diene-2,3-diol-acetonide (23a).…”