Microbial Conversion of Terpenoids

Mikami, Yoichi

doi:10.1080/02648725.1988.10647850

Cited by 26 publications

(19 citation statements)

References 89 publications

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“…Previous reviews dedicated to limonene biotransformation include Braddock and Cadwallader (1995) and Gabrielyan et al (1992). Valuable reviews on bioconversions of terpenoid compounds including limonene were written by Kak (1992), Kieslich et al (1986), Mikami (1988), Trudgill (1990), and Van der Werf et al (1997).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of limonene by bacteria, fungi, yeasts, and plants

Duetz

Bouwmeester²,

Beilen

et al. 2003

Appl Microbiol Biotechnol

226

147

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The past 5 years have seen significant progress in the field of limonene biotransformation, especially with regard to the regiospecificity of microbial biocatalysts. Whereas earlier only regiospecific biocatalysts for the 1,2 position (limonene-1,2-diol) and the 8-position (a-terpineol) were available, recent reports describe microbial biocatalysts specifically hydroxylating the 3-position (isopiperitenol), 6-position (carveol and carvone), and 7-position (perillyl alcohol, perillylaaldehyde, and perillic acid). The present review also includes the considerable progress made in the characterization of plant P-450 limonene hydroxylases and the cloning of the encoding genes.

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Section: Introductionmentioning

confidence: 99%

Biotransformation of limonene by bacteria, fungi, yeasts, and plants

Duetz

Bouwmeester²,

Beilen

et al. 2003

Appl Microbiol Biotechnol

226

147

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“…(E)-4-Methyl-3-hexenoic acid is formed from myrcene (Narushima, Omori, & Minoda, 1982;Mikami, 1988) or linalool (Mizutani, Hayashi, Ueda, & Tatsumi, 1971) via enzyme-catalyzed oxidative degradation. In yuzu (Miyazato et al, 2013), the (E)-isomer is predominant and, in contrast, the (Z)-isomer was not detected.…”

Section: Resultsmentioning

confidence: 99%

Identification of the Compounds Responsible for the Sweat-Like Odor in Hop (Humulus lupulus L.) Volatile Oil

Miyazato¹

2013

JFR

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The aroma of hop volatile oil contains a sweat-like odor. We studied the odorous volatile compounds responsible for the sweat-like odor in the volatile oil extracted from Hallertau Perle hop (Humulus lupulus L.) pellets. The combined use of gas chromatography-mass spectrometry/olfactometry (GC-MS/O), aroma extract dilution analysis (AEDA) by GC-MS/O (an odor dilution technique), and heart-cut multidimensional GC-MS (heart-cut MDGC-MS) equipped with the polar (1D) and apolar (2D) capillary columns revealed seven sweat-like odor producing compounds: methyl-branched saturated and unsaturated aliphatic acids, such as 3-methylbutanoic acid (sweaty/rancid/cheese-like), 2-methylbutanoic acid (sweaty/rancid/cheese-like), 4-methyl-3-pentenoic acid (sweaty/urine-like/malodor in laundry), and (E)-4-methyl-3-hexenoic acid (sweaty/urine-like/malodor in laundry), as well as others, such as an unknown compound (sweaty), methyl (E)-4-methyl-3-hexenoate (sweaty/malodor in laundry/fruity), and S-methyl (E)-4-methyl-3-hexenethioate (sweaty/rubber). The reference substances were synthesized stereoselectively using for the identification procedures. In this study, (E)-4-methyl-3-hexenoic acid, methyl (E)-4-methyl-3-hexenoate, and S-methyl (E)-4-methyl-3-hexenethioate were identified for the first time in hop volatile oil.

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“…49 -Ionone (214a) was bioconverted to 5S-(214e) and 3R-hydroxy--ionone (214g) and the corresponding ketones (214f, 214h) by A. niger. 50 Compound 214a was incubated with Gongronella butleri to afford 214g predominantly, 51 whereas Lasiodiplodia theobromae reduced the C 7 -C 8 double bond of 214a to give dihydro (214c) and oxidative products (214m) 52 (Scheme 43).…”

Section: Biotransformation Of Ionones Damascones and Adamantanesmentioning

confidence: 99%

“…elegans (Scheme 7). The former microbe converted 44 to 19-hydroxystemodin (49), 45 to 19-hydroxystemodinone (50), and 46 to 1-hydroxystemarin (51) and 19-carboxystemarin (52). The latter organism converted 44 to 7-(53), 7-(54), 11-(55), and 3-hydroxystemodin (56) (Scheme 8).…”

mentioning

confidence: 99%