Formation of 2S-Hydroxy-β-ionone and 4ξ-Hydroxy-β-ionone by Microbial Hydroxylation of β-Ionone

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

doi:10.1080/00021369.1978.10863113

Cited by 7 publications

(7 citation statements)

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“…2), was based on several pieces of evidence, all of which are consistent. The absolute configuration at 2-C, depicted in 12 a, was based on the circular dichromatic spectra of 2-acetoxy-,8-ionone derived from 12a as described previously (17). The application of the Horeau method (10) to 12a confirmed the earlier result.…”

Section: Resultssupporting

confidence: 52%

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Microbial Transformation of β -Ionone and β -Methylionone

Mikami

Fukunaga

Arita

et al. 1981

Appl Environ Microbiol

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Aspergillus niger JTS 191 was selected from many microorganisms tested as capable of converting ionones to other compounds having aromas. The individual transformation products from ,B-ionone were isolated and identifled by comparison with synthetically derived compounds. The major products were (R)-4hydroxy-f8-ionone and (S)-2-hydroxy-fl-ionone. 2-Oxo-, 4-oxo-, 3,4-dehydro-, 2,3dehydro-4-oxo-, 3,4-dehydro-2-oxo-, (S)-2-acetoxy-, (R)-4-acetoxy-, and 5,6epoxy-,8-ionone and 4-(2,3,6-trimethylphenyl)-but-3-en-2-one were also identified. Analogous transformation products of ,B-methylionone also were identified. Based on gas-liquid chromatographic analysis during the fermentation, we propose two main oxidative pathways of/3-ionone. The results of this study suggest that these transformations of,B-ionones may be useful as tobacco-flavoring compounds.

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Section: Resultssupporting

confidence: 52%

“…This paper deals mainly with the screening of microorganisms and with the chemical aspects of the transformation of f8-ionone and ,B-methylionone by the selected strain of A. niger. A preliminary report of this study has appeared elsewhere (17).…”

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confidence: 97%

Microbial Transformation of β -Ionone and β -Methylionone

Mikami

Fukunaga

Arita

et al. 1981

Appl Environ Microbiol

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“…In previous reports (9, 10), we demonstrated the usefulness of microbial conversions for the preparation of these aroma compounds. P-Ionone was converted to more than 13 compounds, including (S)-2-hydroxy-,3-ionone and (R)-4hydroxy-p-ionone, by a selected strain of Aspergillus niger, ITS 191; the resulting aroma complex was very effective for tobacco flavoring at the parts per million (micrograms per milligram) level (9,10). A similar result has been reported by Krasnobajew and Helminger with Lasiodiplodia theobromae ATCC 28570 (8).…”

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confidence: 71%

Microbial Conversion of α-Ionone, α-Methylionone, and α-Isomethylionone

Yamazaki

Hayashi

Arita

et al. 1988

Appl Environ Microbiol

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a-Ionone, a-methylionone, and a-isomethylionone were converted by Aspergillus niger JTS 191. The individual bioconversion products from a-ionone were isolated and identified by spectrometry and organic synthesis. The major products were cis-3-hydroxy-a-ionone, trans-3-hydroxy-a-ionone, and 3-oxo-a-ionone. 2,3-Dehydro-a-ionone, 3,4-dehydro-o-ionone, and 1-(6,6-dimethyl-2-methylene-3-cyclohexenyl)-buten-3-one were also identified. Analogous bioconversion products from a-methylionone and a-isomethylionone were also identified. From results of gas-liquid chromatographic analysis during the fermentation, we propose a metabolic pathway for a-ionones and elucidation of stereochemical features of the bioconversion. lonones and their derivatives are widely distributed in nature. They are important constituents of many kinds of essential oils and are presumably generated from carot-* Corresponding author.

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“…These researches were based mainly on the fungi and bacteria-mediated chemical transformations whereas the exploitation of some specific oxido-reductases were described only recently. In particular, Aspergillus niger [13,14], Lasiodiplodia theobromae [15], Cunninghamella blakesleeana [16], Botrytis cinerea [17], Aspergillus awamori [18], Pleurotus sapidus [19], Mortierella isabellina [20] and different Streptomyces strains [21] have proved to be active biocatalysts for the transformation of these kind of compounds. Concerning the use of isolated enzymes or the exploitation of a specific enzymatic activities, both cytochrome P450 monooxygenases [22,23] and engineered whole cell biocatalysts expressing mutant P450 monooxygenases [24], were used for the oxidation of different ionone isomers.…”

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confidence: 99%

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Serra

Simeis

2018

Molecules

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In this work, we describe a study on the biotransformation of seven natural occurring apocarotenoids by means of eleven selected fungal species. The substrates, namely ionone (α-, β- and γ-isomers), 3,4-dehydroionone, damascone (α- and β-isomers) and theaspirane are relevant flavour and fragrances components. We found that most of the investigated biotransformation reactions afforded oxidized products such as hydroxy- keto- or epoxy-derivatives. On the contrary, the reduction of the keto groups or the reduction of the double bond functional groups were observed only for few substrates, where the reduced products are however formed in minor amount. When starting apocarotenoids are isomers of the same chemical compound (e.g., ionone isomers) their biotransformation can give products very different from each other, depending both on the starting substrate and on the fungal species used. Since the majority of the starting apocarotenoids are often available in natural form and the described products are natural compounds, identified in flavours or fragrances, our biotransformation procedures can be regarded as prospective processes for the preparation of high value olfactory active compounds.

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Formation of 2S-Hydroxy-β-ionone and 4ξ-Hydroxy-β-ionone by Microbial Hydroxylation of β-Ionone

Cited by 7 publications

References 0 publications

Microbial Transformation of β -Ionone and β -Methylionone

Microbial Transformation of β -Ionone and β -Methylionone

Microbial Conversion of α-Ionone, α-Methylionone, and α-Isomethylionone

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

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