Formation of 2S-hydroxy-.BETA.-ionone and 4.XI.-hydroxy-.BETA.-ionone by microbial hydroxylation of .BETA.-ionone.

Mikami, Yoichi; Watanabe, Eriko; Fukunaga, Yumiko; Kisaki, Takuro

doi:10.1271/bbb1961.42.1075

Cited by 14 publications

(3 citation statements)

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“…Microbial transformation of ␣-and/or ␤-ionone to a number of hydroxy and oxo derivatives has been reported for several fungal strains (2,4,8,9,18), mainly of the genus Aspergillus, but not for bacterial strains. 3-Hydroxy-␣-ionone was observed, among other metabolites, when Cunninghamella blakesleeana ATCC 8688 (2) or Aspergillus niger JTS 191 (18) was used.…”

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confidence: 99%

Stereo- and Regioselective Hydroxylation of α-Ionone by Streptomyces Strains

Lutz-Wahl¹,

Fischer

Schmidt‐Dannert³

et al. 1998

Appl Environ Microbiol

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A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate β- and/or α-ionone to the respective 3-hydroxy derivatives. With β-ionone as the substrate, 15 strains showed little conversion to 4-hydroxy- and none showed conversion to the 3-hydroxy product as desired. Among these 15 Streptomyces strains, S. fradiae Tü27, S. arenae Tü 495, S. griseus ATCC 13273, S. violaceoniger Tü 38, and S. antibioticus Tü 4 and Tü 46 converted α-ionone to 3-hydroxy-α-ionone with significantly higher hydroxylation activity compared to that of β-ionone. Hydroxylation of racemic α-ionone [(6R)-(−)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S,6S)-hydroxy-α-ionone. Thus, the enzymatic hydroxylation of α-ionone by theStreptomyces strains tested proceeds with both high regio- and stereoselectivity.

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confidence: 99%

Stereo- and Regioselective Hydroxylation of α-Ionone by Streptomyces Strains

Lutz-Wahl¹,

Fischer

Schmidt‐Dannert³

et al. 1998

Appl Environ Microbiol

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“…They found that the biotransformation of -ionone by Aspergillus niger JTS191 gave a mixture of more than 13 derivatives. This complex was very effective for tobacco flavoring at the parts-permillion level (1-5 ppm) (6,7). The recovering yield of -ionone after this reaction time was close to 70%.…”

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confidence: 82%

Determination of the Reaction Yield during Biotransformation of the Volatile and Chemically Unstable Compound β-Ionone by Aspergillus niger

1999

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Biotransformation of beta-ionone by Aspergillus niger IFO 8541 was a complex system, due to the low precursor solubility in water (0.88 mol/m(3)) which gave a two-phase liquid system, its high volatility (vapor pressure 7.2 Pa), and its poor chemical stability. A dynamic model, considering transfers between organic, aqueous, and gas layers, was established. It also took into account the decrease in organic layer area exchange during a process, due to progressive precursor disappearance. Its solving needed separate determination of two parameters. The first-order kinetic constant for chemical degradation, K(1), was estimated from side experiments involving a model system at thermodynamic equilibrium; its value was found to be close to 4.17 x 10(-)(6) s(-)(1). The volumetric transfer coefficient between gas and aqueous phase was estimated by analogy with results obtained for oxygen transfer. Results obtained demonstrated high liquid-gas transfer rates, while liquid-liquid transfers were severely limited. These data were then used to estimate the true yield of a biotransformation experiment, which was found to be close to unity.

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“…1) Many reports have so far been published on the biotransformation of ionone analogues. [2][3][4][5][6][7][8] For example, Mikami et al have reported the microbial transformation of -ionone, 5,6) (AE)--ionone and unnatural (AE)--isomethylionone 7) by Aspergillus niger into the corresponding oxidative hydroxylation products without any degradation. The fermentation of -ionone with Lasiodiplodia theobromae has also been described by Krasnobajew et al 8) to givecyclohomogeraniol as the main degradation product.…”

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confidence: 99%